KR102602194B1 - Condensed-cyclic compound and organic light-emitting device comprising the same - Google Patents

Abstract

Condensed cyclic compounds and organic light-emitting devices containing the same are disclosed.

Description

Condensed-cyclic compound and organic light-emitting device comprising the same}

It relates to condensed cyclic compounds and organic light-emitting devices containing them.

Organic light-emitting devices are self-emitting devices that not only have a wide viewing angle and excellent contrast, but also have a fast response time, excellent brightness, driving voltage, and response speed characteristics, and have the advantage of being multicolorable. .

The organic light-emitting device has a first electrode disposed on an upper part of a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. It can have a structure. Holes injected from the first electrode move to the light-emitting layer via the hole transport region, and electrons injected from the second electrode move to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. Light is generated as this exciton changes from the excited state to the ground state.

The aim is to provide novel condensed cyclic compounds and organic light-emitting devices containing them.

According to one aspect,

A condensed ring compound represented by the following formula 1-1 or 1-2 is provided:

<Formula 1-1>

<Formula 1-2>

In formulas 1-1 and 1-2,

A ₁ ring is benzene,

A ₂ ring is a C ₇ -C ₆₀ aromatic ring or a C ₁ -C ₆₀ heteroaromatic ring,

X ₁ is selected from C(R ₁ )(R ₂ ), O and S,

X ₂ is selected from C(R ₆ )(R ₇ ), O and S,

R ₁ to R _3, R ₆ and R ₇ are independently of each other hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, Hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ - C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, - Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S( =O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

R ₄ and R ₅ are independently of each other, a group represented by the following formula 2, hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or Unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalke Nyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group , -Si(Q ₄ )(Q ₅ )(Q ₆ ), -N(Q ₄ )(Q ₅ ), -B(Q ₄ )(Q ₅ ), -C(=O)(Q ₄ ), - selected from S(=O) ₂ (Q ₄ ) and -P(=O)(Q ₄ )(Q ₅ ), where at least one of R ₄ and R ₅ is a group represented by the following formula (2),

<Formula 2>

In Formula 2 above,

L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted Among the substituted or unsubstituted divalent non-aromatic condensed polycyclic group and the substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group selected,

a1 and a2 are independently selected from 0, 1, 2, and 3,

Ar ₁ is hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalke Nyl group, substituted or unsubstituted C ₆ -C ₆₀ Aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₇ )(Q ₈ )(Q ₉ ) , -N(Q ₇ )(Q ₈ ), -B(Q ₇ )(Q ₈ ), -C(=O)(Q ₇ ), -S(=O) ₂ (Q ₇ ) and -P(= O) is selected from (Q ₇ ) (Q ₈ ),

c1 is selected from integers from 1 to 9,

* is the binding site with the neighboring atom,

b3 is selected from an integer of 1 to 10, b4 is 1 or 2, b5 is selected from an integer of 1 to 4,

The substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C At least one of the substituents of _{the 6} -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ - C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group substituted with at least one selected from among;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic group -aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O) (Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C substituted with at least one selected from ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from,

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group , a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, and a terphenyl group.

Organic light-emitting devices containing the condensed cyclic compound can have high efficiency and long lifespan.

1 to 4 are diagrams schematically showing the structure of an organic light-emitting device according to an embodiment.

The condensed ring compound is represented by the following formula 1-1 or 1-2:

<Formula 1-1>

<Formula 1-2>

In formulas 1-1 and 1-2,

The A ₁ ring may be benzene.

In Formulas 1-1 and 1-2, the A ₂ ring may be a C ₇ -C ₆₀ aromatic ring or a C ₁ -C ₆₀ heteroaromatic ring.

For example, in Formulas 1-1 and 1-2, the A ₂ ring may be selected from naphthalene, anthracene, phenanthrene, and triphenylene.

According to another embodiment, the A ₂ ring in Formulas 1-1 and 1-2 may be naphthalene.

In Formulas 1-1 and 1-2, X ₁ is selected from C(R ₁ )(R ₂ ), O and S, and X ₂ is selected from C(R ₆ )(R ₇ ), O and S. You can. R ₁ , R ₂ , R ₆ and R ₇ refer to what will be described later.

For example, in Formulas 1-1 and 1-2,

X ₁ and X ₂ are S;

X ₁ is C(R ₁ )(R ₂ ) and X ₂ is S;

X ₁ is S and X ₂ is C(R ₆ )(R ₇ );

X ₁ is O and X ₂ is S;

X ₁ and X ₂ are O;

X ₁ is C(R ₁ )(R ₂ ) and X ₂ is O;

X ₁ is O and X ₂ is C(R ₆ )(R ₇ ); or

X ₁ may be S, and X ₂ may be O;

In formulas 1-1 and 1-2,

R ₁ to R _3, R ₆ and R ₇ are independently of each other hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, Hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ - C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, - Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S( =O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

R ₄ and R ₅ are independently of each other, a group represented by the following formula 2, hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or Unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalke Nyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group , -Si(Q ₄ )(Q ₅ )(Q ₆ ), -N(Q ₄ )(Q ₅ ), -B(Q ₄ )(Q ₅ ), -C(=O)(Q ₄ ), - It can be selected from S(=O) ₂ (Q ₄ ) and -P(=O)(Q ₄ )(Q ₅ ).

For example, in Formulas 1-1 and 1-2, R ₁ to R _3, R ₆ and R ₇ are independently of each other,

Hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

-Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S (=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ );

Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, Indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl. (phenanthrenyl), anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl ( ovalenyl, thiophenyl, furanyl, carbazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl ), benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilolyl group; and

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ - C ₂₀ Alkoxy group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group , benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, Perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, A phenyl group, a biphenyl group, a terphenyl group, and a phenyl group substituted with at least one selected from a dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ). Talenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalene Nyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group , rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole dibenzosilolyl and dibenzosilolyl; is selected from,

R ₄ and R ₅ are independently of each other,

A group represented by Formula 2 below;

Hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

-Si(Q ₄ )(Q ₅ )(Q ₆ ), -N(Q ₄ )(Q ₅ ), -B(Q ₄ )(Q ₅ ), -C(=O)(Q ₄ ), -S (=O) ₂ (Q ₄ ) and -P(=O)(Q ₄ )(Q ₅ );

Phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilolyl group; and

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ - C ₂₀ Alkoxy group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group , benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, Perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, Substituted with at least one selected from dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilolyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Talenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group , triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thio phenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilolyl group; is selected from,

Q ₁ to Q ₆ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group. , hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluore. It may be selected from a nyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, and carbazolyl group.

According to another embodiment, in Formulas 1-1 and 1-2,

R ₁ to R _3, R ₆ and R ₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ Alkoxy group;

-Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ) and -B(Q ₁ )(Q ₂ );

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group , benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazole Substituted with at least one selected from diary group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), phenyl group, biphenyl group, ter Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, dibenzofuranyl group, Dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; is selected from,

R ₄ and R ₅ are independently of each other,

A group represented by Formula 2 below;

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ Alkoxy group;

-Si(Q ₄ )(Q ₅ )(Q ₆ ), -N(Q ₄ )(Q ₅ ) and -B(Q ₄ )(Q ₅ );

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group , benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazole phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl substituted with at least one selected from the group consisting of dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group. group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group. ; is selected from,

Q ₁ to Q ₆ and Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to another embodiment, in Formulas 1-1 and 1-2,

R ₄ is a group represented by the following formula 2, and R ₅ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydra selected from a zono group, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group; or

R ₄ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ It is selected from -C ₂₀ alkoxy groups, and R ₅ may be a group represented by the following formula (2), but is not limited thereto.

However, in Formulas 1-1 and 1-2, at least one of R ₄ and R ₅ may be a group represented by Formula 2 below:

<Formula 2>

In Formula 2 above,

L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted Among the substituted or unsubstituted divalent non-aromatic condensed polycyclic group and the substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group can be selected

For example, in Formula 2 above,

The L ₁ and L ₂ are each independently selected from a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, and a hepthalenylene group ( heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenyl Phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, Naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, Coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, carbazolylene, benzofuranylene (benzofuranylene), benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group and dibenzocarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylgyrenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylgyrenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group. , a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, substituted with at least one of a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, and an azulenylene group. , hepthalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, Anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenylene group , coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanylene group, carbazonylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzo Carbazolylene group and dibenzocarbazolylene group; can be selected from among.

According to another embodiment, in Formula 2, L ₁ and L ₂ may be independently selected from the group represented by the following Formulas 3-1 to 3-22, but are not limited thereto:

In Formulas 3-1 to 3-22,

Y ₁ is selected from O, S, C(Z ₃ )(Z ₄ ), N(Z ₅ ) and Si(Z ₆ )(Z ₇ ),

Z ₁ to Z ₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, selected from anthracenyl group, pyrenyl group, chrysenyl group, carbazolyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),

Q ₃₁ to Q ₃₃ are independently selected from C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group,

d1 is selected from an integer of 1 to 4, d2 is selected from an integer of 1 to 3, d3 is selected from an integer of 1 to 6, d4 is selected from an integer of 1 to 8, and d5 is selected from an integer of 1 to 5. is selected from among integers, and * and *' are bonding sites with neighboring atoms.

According to another embodiment, in Formula 2, L ₁ and L ₂ may be independently selected from the group represented by the following Formulas 4-1 to 4-35:

In Formulas 4-1 and 4-35, * and *' are bonding sites with neighboring atoms.

In Formula 2, a1 represents the number of L ₁ and is selected from 0, 1, 2, and 3. For example, a1 in Formula 2 may be 0 or 1, but is not limited thereto. When a1 is 0, *-(L ₁ ) _a1 -*' is a single bond. When a1 is 2 or more, 2 or more L _1s are the same or different from each other.

In Formula 2, a2 represents the number of L ₂ and is selected from 0, 1, 2, and 3. For example, a2 in Formula 2 may be 0 or 1, but is not limited thereto. When a2 is 0, *-(L ₂ ) _a2 -*' is a single bond. When a2 is 2 or more, 2 or more L _2s are the same or different from each other.

As another example, in Formula 2 above,

a1 is 0 and a2 is 1; or

a1 may be 1 and a2 may be 0, but are not limited thereto.

In Formula 2, Ar ₁ is hydrogen, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, Substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ - C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or Unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₇ )(Q ₈ )(Q ₉ ), -N(Q ₇ )(Q ₈ ), -B(Q ₇ )(Q ₈ ), -C(=O)(Q ₇ ), -S(=O) ₂ (Q ₇ ) and -P(=O)(Q ₇ )(Q ₈ ).

For example, Ar ₁ in Formula 2 is,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ Alkoxy group;

Phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group , hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzoyl group. Carbazolyl group, dibenzocarbazolyl group and dibenzosilolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group. , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, substituted with at least one selected from benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ). Nyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group , anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, Coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilol. diary; is selected from,

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group.

According to another embodiment, Ar ₁ in Formula 2 is,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ Alkoxy group; and

Condensed ring compounds selected from the group represented by the following formulas 5-1 to 5-16:

In formulas 5-1 to 5-16,

Y ₃₁ is selected from O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) and Si(Z ₃₆ )(Z ₃₇ ),

Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group , chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrethyl group. Phenyl group, biphenyl group, terphenyl group, naphthyl group substituted with at least one selected from the group consisting of nyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group. , fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group. , carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; is selected from,

e3 is selected from integers 1 to 3, e4 is selected from integers 1 to 4, e5 is selected from integers 1 to 5, e6 is selected from integers 1 to 6, and e7 is selected from integers 1 to 7. is selected from an integer, and e9 is selected from an integer of 1 to 9.

According to another embodiment, Ar ₁ in Formula 2 is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazo No group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group;

It may be selected from the group represented by the following formulas 5-1 to 5-16, but is not limited thereto:

In formulas 5-1 to 5-16,

Y ₃₁ is selected from O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) and Si(Z ₃₆ )(Z ₃₇ ),

Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group , chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrethyl group. Phenyl group, biphenyl group, terphenyl group, naphthyl group substituted with at least one selected from the group consisting of nyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group. , fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group. , carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; is selected from,

e3 is selected from integers 1 to 3, e4 is selected from integers 1 to 4, e5 is selected from integers 1 to 5, e6 is selected from integers 1 to 6, and e7 is selected from integers 1 to 7. selected from integers, and e9 may be selected from integers 1 to 9.

According to another embodiment, Ar ₁ in Formula 2 is,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ Alkoxy group;

It may be selected from the group represented by the following formulas 6-1 to 6-44, but is not limited thereto:

In Formulas 6-1 to 6-44, * is a bonding site with a neighboring atom.

According to another embodiment, in Formula 2,

Ar ₁ is phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, dibenzofuranyl group and dibenzoyl group. Thiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazole, substituted with at least one selected from phenyl group and naphthyl group. diyl group, dibenzofuranyl group and dibenzothiophenyl group; can be selected from among.

In Formula 2, c1 may be selected from an integer of 1 to 9.

In Formula 2, c1 represents the number of -[(L ₁ ) _a1 -Ar ₁ ], and when c1 is 2 or more, 2 or more -[(L ₁ ) _a1 -Ar ₁ ] are the same or different from each other. For example, c1 may be selected from an integer of 1 to 4. As another example, c1 in Formula 2 may be 1 or 2.

In Formulas 1-1 and 1-2, b3 may be selected from an integer of 1 to 10, b4 may be 1 or 2, and b5 may be selected from an integer of 1 to 4.

In Formulas 1-1 and 1-2, b3 represents the number of R ₁ , and when b3 is 2 or more, 2 or more R ₁ are the same or different from each other. The description of b4 and b5 can be understood by referring to the description of b3 and the structures of Formulas 1-1 and 1-2.

According to one embodiment, in Formulas 1-1 and 1-2, at least one of R ₄ and R ₅ may be represented by the following Formula 2A:

<Formula 2A>

In Formula 2A, L ₁ , L ₂ , a1 and a2 refer to what is described in this specification, Ar _1a to Ar _1i refer to Ar ₁ described in this specification, and * is a bonding site with a neighboring atom.

For example, in Formula 2A, Ar _1a to Ar _1i are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ Alkoxy group; and

It may be selected from the groups represented by Formulas 6-1 to 6-44.

According to another embodiment, in Formulas 1-1 and 1-2, at least one of R ₄ and R ₅ may be represented by the following Formula 2A(1):

<Formula 2A(1)>

In the above formula 2A(1), L ₁ , L ₂ , a1 and a2 refer to what is described in this specification, Ar _1e refers to Ar ₁ described in this specification, and * is a bonding site with a neighboring atom.

For example, in Formula 2A(1), Ar _1e may be selected from the groups represented by Formulas 6-1 to 6-44.

As another example, in Formula 2A(1), Ar _1e is phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, and chrysenyl group. , carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazole, substituted with at least one selected from phenyl group and naphthyl group. diyl group, dibenzofuranyl group and dibenzothiophenyl group; can be selected from among.

According to one embodiment, the condensed ring compound may be represented by one of the following formulas 1(1) to 1(10):

<Formula 1(1)>

<Formula 1(2)>

<Formula 1(3)>

<Formula 1(4)>

<Formula 1(5)>

<Formula 1(6)>

<Formula 1(7)>

<Formula 1(8)>

<Formula 1(9)>

<Formula 1(10)>

In Formulas 1 ₍ 1 ₎ to 1 (10 _{) ,} A ₁ , _{A 2} , X ₁ , to R _5c refer to R ₅ described herein, and Ar _1a to Ar _1i refer to Ar ₁ described herein.

For example, in Formulas 1(1) to 1(10), A ₂ may be naphthalene.

According to another embodiment, the condensed ring compound may be represented by one of the following formulas 1(1)-1 to 1(10)-1, but is not limited thereto:

<Formula 1(1)-1>

<Formula 1(2)-1>

<Formula 1(3)-1>

<Formula 1(4)-1>

<Formula 1(5)-1>

<Formula 1(6)-1>

<Formula 1(7)-1>

<Formula 1(8)-1>

<Formula 1(9)-1>

<Formula 1(10)-1>

In the above formulas ₁ (1) _-1 to 1 ₍ 10 ₎ -1 _{, A 1 ,} A ₂ , See Ar ₁ described herein.

For example, in Formulas 1(1)-1 to 1(10)-1, A ₂ may be naphthalene.

According to one embodiment, the condensed ring compound may be selected from the following compounds, but is not limited thereto:

Or, for example, the condensed ring compound may be one of the following compounds H1 to H9:

The condensed ring compound represented by Formula 1-1 or 1-2 can be synthesized using known organic synthesis methods. The method for synthesizing the condensed ring compound can be recognized by those skilled in the art by referring to the examples described below.

[Description of Figure 1]

Figure 1 schematically shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to an embodiment of the present invention will be described with reference to FIG. 1.

[First electrode (110)]

A substrate may be additionally disposed below the first electrode 110 or above the second electrode 190 in FIG. 1 . As the substrate, a glass substrate or a plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 110 may be formed, for example, by providing a first electrode material on the upper part of the substrate using a deposition method or sputtering method. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials with a high work function to facilitate hole injection.

The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode 110, which is a transmissive electrode, the first electrode material is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and any of them. It may be selected from a combination of, but is not limited to this. Alternatively, to form the first electrode 110, which is a transflective electrode or a reflective electrode, the first electrode material is magnesium (Mg), silver (Ag), aluminum (Al), or aluminum-lithium (Al-Li). ), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but is not limited thereto.

The first electrode 110 may have a single-layer structure or a multi-layer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but is not limited to this.

[Organic layer (150)]

An organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light emitting layer.

The organic layer 150 may include a condensed ring compound represented by Formula 1-1 or 1-2.

The organic layer 150 includes a hole transport region between the first electrode 110 and the light-emitting layer and an electron transport region between the light-emitting layer and the second electrode 190. region) may be further included.

[Hole transport area in organic layer 150]

The hole transport region may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of a plurality of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials. It can have a structure.

The hole transport region may include a condensed ring compound represented by Formula 1-1 or 1-2.

The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, and an electron blocking layer (EBL).

For example, the hole transport region has a single-layer structure consisting of a single layer made of a plurality of different materials, or a hole injection layer/hole transport layer or a hole injection layer/hole transport layer sequentially stacked from the first electrode 110. /It may have a multi-layer structure of a light-emitting auxiliary layer, a hole injection layer/light-emitting auxiliary layer, a hole transport layer/light-emitting auxiliary layer, or a hole injection layer/hole transport layer/electron blocking layer, but is not limited thereto.

The hole transport region is m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA(4,4' ,4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid)) , PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/ Camphor sulfonic acid (polyaniline/camphorsulfonic acid)), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate)), a compound represented by Formula 201 below, and a compound represented by Formula 202 below It may include at least one compound selected from:

<Formula 201>

<Formula 202>

In formulas 201 and 202,

L ₂₀₁ to L ₂₀₄ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted selected from a substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group,

L ₂₀₅ is, *-O-*', *-S-*', *-N(Q ₂₀₁ )-*', substituted or unsubstituted C ₁ -C ₂₀ alkylene group, substituted or unsubstituted C ₂ - C ₂₀ alkenylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent selected from non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed polycyclic groups,

xa1 to xa4 are independently selected from integers from 0 to 3,

xa5 is selected from an integer from 1 to 10,

R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic heterocondensed group. It may be selected from polycyclic groups.

For example, in Formula 202, R ₂₀₁ and R ₂₀₂ may be optionally connected to each other through a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R ₂₀₃ and R ₂₀₄ may be optionally connected to each other, They may be linked to each other through a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

According to one embodiment, in Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are independently of each other,

Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluore Nylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, pe Relenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubcenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group , benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group and pyridinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, pentale Nyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group , phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, Rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole Phenyl substituted with at least one selected from the group consisting of dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) Len group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenyl Len group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perile Nylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubisenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazonylene group, indolelylene group, isoindolylene group, Benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group and pyridinylene group;

is selected from,

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to another embodiment, xa1 to xa4 may be independently 0, 1, or 2.

According to another embodiment, xa5 may be 1, 2, 3, or 4.

According to another embodiment, R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a hepthalenyl group, an indacenyl group, Acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazole diyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, pentale Nyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group , phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, Rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole A phenyl group substituted with at least one selected from the group consisting of dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) , biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group , hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group. , dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group;

can be selected from,

For a description of Q ₃₁ to Q ₃₃ , refer to what is described in the present specification.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₃ in Formula 201 is independently of each other,

fluorenyl group, spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, naphthyl group. , fluorenyl group, spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group, substituted with at least one selected from fluorenyl group, spiro-bifluorenyl group, carbazolyl group, di benzofuranyl group and dibenzothiophenyl group;

It may be selected from among, but is not limited to.

According to another embodiment, in Formula 202, i) R ₂₀₁ and R ₂₀₂ may be connected to each other through a single bond, and/or ii) R ₂₀₃ and R ₂₀₄ may be connected to each other through a single bond.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₄ in Formula 202 is,

Carbazole diary; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, naphthyl group. , a carbazolyl group substituted with at least one selected from a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

It may be selected from among, but is not limited to.

The compound represented by Formula 201 may be represented by the following Formula 201A:

<Formula 201A>

For example, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but is not limited thereto:

<Formula 201A(1)>

As another example, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but is not limited thereto:

<Formula 201A-1>

Meanwhile, the compound represented by Formula 202 may be represented by the following Formula 202A:

<Formula 202A>

According to another embodiment, the compound represented by Formula 202 may be represented by the following Formula 202A-1:

<Formula 202A-1>

Among the formulas 201A, 201A(1), 201A-1, 202A and 202A-1,

For descriptions of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ , refer to what is described herein,

For descriptions of R ₂₁₁ and R ₂₁₂ , refer to the description of R ₂₀₃ in this specification,

R ₂₁₃ to R ₂₁₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ substituted with alkyl group. phenyl group, phenyl group substituted with -F, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflu Orenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group , pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, di It may be selected from benzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and pyridinyl group.

The hole transport region may include at least one compound selected from the following compounds HT1 to HT39, but is not limited thereto:

The thickness of the hole transport region may be about 100Å to about 10000Å, for example, about 100Å to about 1000Å. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 9000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å. It may be from about 2000 Å, for example from about 100 Å to about 1500 Å. When the thickness of the hole transport region, hole injection layer, and hole transport layer satisfies the above-mentioned ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

The light emitting auxiliary layer is a layer that serves to increase light emission efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light emitting layer, and the electron blocking layer is a layer that serves to prevent electron injection from the electron transport region. am. The light emitting auxiliary layer and the electron blocking layer may include materials as described above.

[p-dopant]

In addition to the materials described above, the hole transport region may further include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-generating material may be, for example, a p-dopant.

According to one embodiment, the LUMO of the p-dopant may be -3.5 eV or less.

The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto.

For example, the p-dopant is,

Quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane);

metal oxides such as tungsten oxide and molybdenum oxide;

HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile); and

A compound represented by the following formula 221;

It may include, but is not limited to, at least one selected from:

<HAT-CN> <F4-TCNQ>

<Formula 221>

In Formula 221,

R ₂₂₁ to R ₂₂₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group. , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, wherein at least one of R ₂₂₁ to R ₂₂₃ is a cyano group, -F, -Cl, -Br, -I, At least one selected from a C ₁ -C ₂₀ alkyl group substituted with -F, a C ₁ -C ₂₀ alkyl group substituted with -Cl, a C ₁ -C ₂₀ alkyl group substituted with -Br, and a C ₁ -C ₂₀ alkyl group substituted with -I It has one substituent.

[Emitting layer of organic layer (150)]

When the organic light emitting device 10 is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each subpixel. Alternatively, the light-emitting layer may have a structure in which two or more layers selected from a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are stacked in contact or spaced apart, or two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material may be layered. It has a mixed structure and can emit white light.

The light emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

The light-emitting layer may include a condensed ring compound represented by Formula 1-1 or 1-2.

The host may include a condensed ring compound represented by Formula 1-1 or 1-2.

The light-emitting layer may further include a fluorescent dopant in addition to the condensed ring compound represented by Formula 1-1 or 1-2.

The content of the dopant in the light-emitting layer can typically be selected in the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100Å to about 1000Å, for example, about 200Å to about 600Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[Phosphorescent dopant included in the light-emitting layer of the organic layer 150]

The phosphorescent dopant may include an organometallic complex represented by the following chemical formula 401:

<Formula 401>

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

In formulas 401 and 402,

M is iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) ) and thulium (Tm),

L ₄₀₁ is selected from the ligands represented by formula 402, xc1 is 1, 2, or 3, and when xc1 is 2 or more, 2 or more L ₄₀₁ are the same or different from each other,

L ₄₀₂ is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, 2 or more L ₄₀₂ are the same or different from each other,

X ₄₀₁ to X ₄₀₄ are each independently nitrogen or carbon,

X ₄₀₁ and X ₄₀₃ are connected through a single bond or double bond, X ₄₀₂ and X ₄₀₄ are connected through a single bond or double bond,

A ₄₀₁ and A ₄₀₂ are, independently of each other, a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,

X ₄₀₅ is a single binding, *-o- *', *-S- *', *-c (= o)- *', *-n (Q ₄₁₁ )- *', *-c (Q ₄₁₁ ) Q ₄₁₂ )-*', *-C(Q ₄₁₁ )=C(Q ₄₁₂ )-*', *-C(Q ₄₁₁ )=*' or *=C(Q ₄₁₁ )=*', and the Q ₄₁₁ and Q ₄₁₂ is hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group,

X ₄₀₆ is a single bond, O or S,

R ₄₀₁ and R ₄₀₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or Unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ - C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or Unsubstituted monovalent non-aromatic heterocondensed polycyclic group -Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), -N(Q ₄₀₁ )(Q ₄₀₂ ), -B(Q ₄₀₁ )(Q ₄₀₂ ), - C(=O)(Q ₄₀₁ ), -S(=O) ₂ (Q ₄₀₁ ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ ), wherein Q ₄₀₁ to Q ₄₀₃ are independently of each other. , C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₁ -C ₂₀ heteroaryl group,

xc11 and xc12 are independently selected from integers from 0 to 10,

* and *' in Formula 402 are binding sites with M in Formula 401.

According to one embodiment, in Formula 402, A ₄₀₁ and A ₄₀₂ are each independently selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, and a furan ( furan) group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, quinoline group, iso Quinoline group, benzoquinoline group, quinoxaline group, quinazoline group, carbazole group, benzoimidazole group, benzofuran group, benzothiophene group, isobenzothiophene group, benzoxazole group, isobenzooxa It may be selected from the sol group, triazole group, tetrazole group, oxadiazole group, triazine group, dibenzofuran group and dibenzothiophene group.

According to another embodiment, in Formula 402, i) X ₄₀₁ may be nitrogen and X ₄₀₂ may be carbon, or ii) both X ₄₀₁ and X ₄₀₂ may be nitrogen.

According to another embodiment, in Formula 402, R ₄₀₁ and R ₄₀₂ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ Alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, phenyl group, naphthyl group, cyclopentyl group, cyclohexyl group, ada C ₁ -C 20 _alkyl group and C 1 _{-C 20} alkoxy group substituted with at least one selected from mantanyl group, _norbonanyl group and norbornenyl group;

Cyclopentyl group, cyclohexyl group, adamantanyl group, norbonanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, adamantanyl group, norbonanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyrida Cyclopentyl group, cyclohexyl group substituted with at least one selected from zinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group. Syl group, adamantanyl group, norbonanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinium Nolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; and

-Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), -N(Q ₄₀₁ )(Q ₄₀₂ ), -B(Q ₄₀₁ )(Q ₄₀₂ ), -C(=O)(Q ₄₀₁ ), -S (=O) ₂ (Q ₄₀₁ ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ );

is selected from,

Q ₄₀₁ to Q ₄₀₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but are not limited thereto.

According to another embodiment, when xc1 in Formula 401 is 2 or more, two A _{401 out of two or more L 401 are} optionally connected to each other through X ₄₀₇ , which is a linking group, or two A ₄₀₂ are optionally connected to each other. , can be connected to each other through the linking group X ₄₀₈ (see compounds PD1 to PD4 and PD7 below). Wherein _{X 407 and} *-C(Q ₄₁₃ )(Q ₄₁₄ )-*' or *-C(Q ₄₁₃ )=C(Q ₄₁₄ )-*' (where Q ₄₁₃ and Q ₄₁₄ are independently of each other, hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group), but is not limited thereto.

In Formula 401, L ₄₀₂ may be any monovalent, divalent, or trivalent organic ligand. For example, the L ₄₀₂ is halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), -C(=O), isonitrile, -CN, and phosphorus. (For example, phosphine, phosphite), but is not limited thereto.

Alternatively, the phosphorescent dopant may be selected from, for example, the following compounds PD1 to PD25, but is not limited thereto:

[Fluorescent dopant in the emitting layer]

The fluorescent dopant may include an arylamine compound or a styrylamine compound.

The fluorescent dopant may include a compound represented by the following formula 501:

<Formula 501>

In formula 501,

Ar ₅₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

L ₅₀₁ to L ₅₀₃ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group. Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted selected from a substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group,

xd1 to xd3 are independently selected from integers from 0 to 3,

R ₅₀₁ and R ₅₀₂ are independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group. , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. selected,

Xd4 may be selected from an integer of 1 to 6.

According to one embodiment, Ar ₅₀₁ in Formula 501 is,

Naphthalene group, hepthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group , pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group and indenophenanthrene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , naphthalene group, hepthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene, substituted with at least one selected from phenyl group, biphenyl group, terphenyl group and naphthyl group. group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group and indenophenan. Tren Group;

can be selected from among.

According to another embodiment, in Formula 501, L ₅₀₁ to L ₅₀₃ are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Lenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group, benzoyl group furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group. , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group, substituted with at least one selected from phenylene group, naphthylene group, fluorenylene group, spy Rho-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perile Nylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazoylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranyl Len group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group;

can be selected from among.

According to another embodiment, in Formula 501, R ₅₀₁ and R ₅₀₂ are independently of each other,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group. , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ). phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, tri Phenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothio phenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group;

is selected from,

Q ₃₁ to Q ₃₃ may be selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to another embodiment, xd4 in Formula 501 may be 2, but is not limited thereto.

For example, the fluorescent dopant may be selected from the following compounds FD1 to FD22:

Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto.

[Electron transport area in organic layer 150]

The electron transport region has i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of a plurality of different materials, or iii) a multi-layer structure having a plurality of layers made of a plurality of different materials. You can have

The electron transport region may include a condensed ring compound represented by Formula 1-1 or 1-2.

The electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transport region may be an electron transport layer/electron injection layer, a hole blocking layer/electron transport layer/electron injection layer, an electron control layer/electron transport layer/electron injection layer, or a buffer layer/electron transport layer/ It may have a structure such as an electron injection layer, but is not limited thereto.

The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing ring. .

The "π electron-deficient nitrogen ring" refers to a C ₁ -C ₆₀ heterocyclic group having at least one *-N=*' moiety as a ring-forming moiety.

For example, the "π electron deficient nitrogen ring" is i) a 5-7 membered heteromonocyclic group with at least one *-N=*' moiety, or ii) at least one *- a heteropolycyclic group in which two or more of the 5- to 7-membered heteromonocyclic groups having an N=*' moiety are condensed with each other, or iii) a 5-membered group having at least one *-N=*' moiety. It may be a heteropolycyclic group in which at least one of the to 7-membered heteromonocyclic group and at least one C ₅ -C ₆₀ carbocyclic group are condensed with each other.

Specific examples of the π electron-deficient nitrogen-containing ring include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, and purine. , quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzoimidazole, isobenzothiazole, benzoline. Examples include oxazole, isobenzooxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but are not limited thereto.

For example, the electron transport region may include a compound represented by Chemical Formula 601 below.

<Formula 601>

[Ar ₆₀₁ ] _xe11 -[(L ₆₀₁ ) _xe1 -R ₆₀₁ ] _xe21

In the above formula 601,

Ar ₆₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

xe11 is 1, 2, or 3,

L ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non- selected from aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups,

xe1 is selected from integers from 0 to 5,

R ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₆₀₁ ) (Q ₆₀₂ )(Q ₆₀₃ ), -C(=O)(Q ₆₀₁ ), -S(=O) ₂ (Q ₆₀₁ ) and -P(=O)(Q ₆₀₁ )(Q ₆₀₂ ) and ,

Q ₆₀₁ to Q ₆₀₃ are each independently a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

xe21 is selected from an integer from 1 to 5.

According to one embodiment, at least one of the xe11 Ar _601s and the xe21 R _601s may include a π electron-deficient nitrogen-containing ring as described above.

According to one embodiment, ring Ar ₆₀₁ in Formula 601 is,

Benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, Pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group , thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, Phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group , benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group. ; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )( Q ₃₂ ) substituted with at least one selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, Fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carba Sol group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, Benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyridine group, polyzopyrimidine group and azacarbazole group;

can be selected from,

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In Formula 601, when xe11 is 2 or more, 2 or more Ar ₆₀₁ may be connected to each other through a single bond.

According to another embodiment, Ar ₆₀₁ in Formula 601 may be an anthracene group.

According to another embodiment, the compound represented by 601 may be represented by the following formula 601-1:

<Formula 601-1>

In the above formula 601-1,

X ₆₁₄ is N or C(R ₆₁₄ ), X ₆₁₅ is N _{or C(R 615), X 616 is N or C(R 616 ) , and at} least one of

L ₆₁₁ to L ₆₁₃ are independent of each other, refer to the description of L ₆₀₁ above,

xe611 to xe613 are independent of each other, refer to the description of xe1 above,

R ₆₁₁ to R ₆₁₃ are independent of each other, refer to the description of R ₆₀₁ above,

R ₆₁₄ to R ₆₁₆ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ It may be selected from -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, and naphthyl group.

According to one embodiment, in Formulas 601 and 601-1, L ₆₀₁ and L ₆₁₁ to L ₆₁₃ are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Lenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group, benzoyl group Furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group, imidazolylene group, pyrazonylene group , thiazonylene group, isothiazolylene group, oxazonylene group, isoxazonylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Len group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinilene group, quinazolinylene group, cynolinylene group, phenanthridinylene group, acridinylene group, phenane Trolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazolylene group, triazonylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidi nylene group and azacarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group. , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group, substituted with at least one selected from phenylene group, naphthylene group, fluorenylene group, Spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, pe Relenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazoylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofu Lanylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group, imidazolylene group, pyrazoylene group, thiazonylene group, isothiazolylene group, oxazolyl Len group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinyl Len group, phthalazinylene group, naphthyridinylene group, quinoxalinilene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazynylene group, benzoimidazolyl Len group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazonylene group, triazonylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group;

It may be selected from among, but is not limited to.

According to another embodiment, xe1 and xe611 to xe613 in Formulas 601 and 601-1 may be independently 0, 1, or 2.

According to another embodiment, in Formulas 601 and 601-1, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ are independently of each other,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group , isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group. , naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group. , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group, substituted with at least one selected from phenyl group, biphenyl group, terphenyl group, naphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perile Nyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Zolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadia Zolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group , cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diary group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; and

-S(=O) ₂ (Q ₆₀₁ ) and -P(=O)(Q ₆₀₁ )(Q ₆₀₂ );

is selected from,

For descriptions of Q ₆₀₁ and Q ₆₀₂ , refer to what is described herein.

The electron transport region may include at least one compound selected from the following compounds ET1 to ET36, but is not limited thereto:

Alternatively, the electron transport region is BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), Alq ₃ , Balq, TAZ(3-(Biphenyl-4-yl)-5-(4- tert -butylphenyl)-4-phenyl-4 H -1 , 2,4-triazole) and NTAZ.

The thickness of the buffer layer, hole blocking layer, or electron control layer may independently range from about 20 Å to about 1000 Å, for example, from about 30 Å to about 300 Å. When the thickness of the buffer layer, hole blocking layer, or electron control layer satisfies the range described above, excellent hole blocking characteristics or electron control characteristics can be obtained without a substantial increase in driving voltage.

The thickness of the electron transport layer may be about 100Å to about 1000Å, for example, about 150Å to about 500Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.

The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkaline metal complex may be selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, and Ba ions may be selected. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, and hydroxyphenyl. Oxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but is not limited thereto.

For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

The electron injection layer has i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of a plurality of different materials, or iii) a multi-layer structure having a plurality of layers made of a plurality of different materials. You can have

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. According to one embodiment, the alkali metal may be Li, Na, or Cs. According to another embodiment, the alkali metal may be Li or Cs, but is not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, Gd, and Tb.

The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be selected from oxides and halides (e.g., fluoride, chloride, bromide, iodide, etc.) of the alkali metal, alkaline earth metal, and rare earth metal. there is.

The alkali metal compound may be selected from alkali metal oxides such as Li ₂ O, Cs ₂ O, K ₂ O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc. According to one embodiment, the alkali metal compound may be selected from LiF, Li ₂ O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.

The alkaline earth metal compound may be selected from alkaline earth metal compounds such as BaO, SrO, CaO, Ba _x Sr _1-x O (0<x<1), Ba _x Ca _1-x O (0<x<1), etc. there is. According to one embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but is not limited thereto.

The rare earth metal compound may be selected from YbF ₃ , ScF ₃ , ScO ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ , and TbF ₃ . According to one embodiment, the rare earth metal compound may be selected from YbF ₃ , ScF ₃ , TbF ₃ , YbI ₃ , ScI ₃ , and TbI ₃ , but is not limited thereto.

The alkali metal complex, alkaline earth metal complex, and rare earth metal complex include ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and are coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, and rare earth metal complex. The ligands are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, and hydroxydiphenyloxa. It may be selected from diazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but is limited thereto. That is not the case.

The electron injection layer may be composed of only the reducing dopant as described above, or may further include an organic material in addition to the reducing dopant. When the electron injection layer includes the reducing dopant and an organic material, the reducing dopant may be uniformly or non-uniformly dispersed in the matrix made of the organic material.

The thickness of the electron injection layer may be about 1Å to about 100Å, or about 3Å to about 90Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[Second electrode (190)]

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. In this case, materials for the second electrode 190 include metals, alloys, electrically conductive compounds, and mixtures thereof having a low work function. can be used.

The second electrode 190 includes lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), and magnesium-indium (Mg-In). ), magnesium-silver (Mg-Ag), ITO, and IZO, but is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layer structure or a multi-layer structure having a plurality of layers.

[Description of Figures 2 to 4]

Meanwhile, the organic light emitting device 20 of FIG. 2 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are sequentially stacked, and the organic light emitting device 20 of FIG. 3 The light emitting device 30 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are sequentially stacked, and the organic light emitting device 40 of FIG. 4 is It has a structure in which the first capping layer 210, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 are sequentially stacked.

For descriptions of the first electrode 110, the organic layer 150, and the second electrode 190 in FIGS. 2 to 4, refer to the description of FIG. 1.

The light generated in the light-emitting layer of the organic layer 150 of the organic light-emitting device 20 and 40 may pass through the first electrode 110 and the first capping layer 210, which are semi-transmissive electrodes or transmissive electrodes, and be extracted to the outside. Light generated in the light-emitting layer of the organic layer 150 of the organic light-emitting devices 30 and 40 may be extracted to the outside through the second electrode 190 and the second capping layer 220, which are semi-transmissive or transmissive electrodes.

The first capping layer 210 and the second capping layer 220 may serve to improve external light emission efficiency based on the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may independently be an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one of the first capping layer 210 and the second capping layer 220 is, independently of each other, a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphine derivative, a phthalocyanine derivative ( It may include at least one material selected from phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds and amine compounds may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br and I. . According to one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include an amine-based compound.

For example, at least one of the first capping layer 210 and the second capping layer 220 may include a condensed ring compound represented by Formula 1-1 or 1-2.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include a compound represented by Formula 201 or a compound represented by Formula 202. there is.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include a compound selected from the compounds HT28 to HT33 and the following compounds CP1 to CP5. However, it is not limited to this.

Above, the organic light emitting device has been described with reference to FIGS. 1 to 4, but is not limited thereto.

Each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are, respectively, vacuum deposition method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, and laser method. It can be formed in a predetermined area using various methods such as thermal transfer (Laser Induced Thermal Imaging, LITI).

When forming each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., about 10 A vacuum degree of ^-8 to about 10 ^-3 torr and a deposition rate of about 0.01 to about 100 Å/sec may be selected in consideration of the compound to be included in the layer to be formed and the structure of the layer to be formed.

When forming each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region by spin coating, the coating conditions include, for example, a coating speed of about 2000 rpm to about 5000 rpm and a coating speed of about 80 rpm. The heat treatment temperature within the range of ℃ to 200℃ may be selected in consideration of the compound to be included in the layer to be formed and the structure of the layer to be formed.

[General definition of substituent]

As used herein, C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl group, ethyl group, propyl group, isobutyl group, and sec-butyl group. group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, etc. As used herein, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

As used herein, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group containing at least one carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group, propenyl group, and butenyl group. etc. are included. As used herein, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

As used herein, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group containing one or more carbon triple bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group, propynyl group, etc. Included. As used herein, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

As used herein, C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group and ethoxy group. , isopropyloxy group, etc.

As used herein, C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cyclo Heptyl group, etc. are included. As used herein, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom. , Specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, etc. As used herein, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, C ₃ -C ₁₀ cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring but does not have aromaticity, and its specific details Examples include cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, etc. As used herein, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

As used herein, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, forming a ring. It has at least one double bond within it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-hydrofuranyl group, and 2,3-hydrothiophenyl group. etc. are included. As used herein, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

As used herein, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic system having 6 to 60 carbon atoms. It means a divalent group with . Specific examples of the C ₆ -C ₆₀ aryl group include phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, etc. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be condensed with each other.

As used herein, the C ₁ -C ₆₀ heteroaryl group is a monovalent group containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms. means, and the C ₁ -C ₆₀ heteroarylene group is 2 which contains at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and has a heterocyclic aromatic system having 1 to 60 carbon atoms. means group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, etc. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be condensed with each other.

As used herein, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (where A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group refers to -SA ₁₀₃ (where A 102 is the C 6 -C 60 aryl group). , A ₁₀₃ refers to the C ₆ -C ₆₀ aryl group).

As used herein, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring forming atom, and the entire molecule is non-aromatic. It means a monovalent group having (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. As used herein, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclic group (non-aromatic condensed heteropolycyclic group) has two or more rings condensed with each other, and at least one selected from N, O, Si, P and S in addition to carbon as a ring forming atom. It refers to a monovalent group (for example, having 1 to 60 carbon atoms) that contains a heteroatom and the entire molecule is non-aromatic. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include carbazolyl group and the like. As used herein, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

As used herein, the C ₅ -C ₆₀ carbocyclic group refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms containing only carbon as a ring-forming atom. The C ₅ -C ₆₀ carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C ₅ -C ₆₀ carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, depending on the number of substituents connected to the C ₅ -C ₆₀ carbocyclic group, various modifications are possible, such as the C ₅ -C ₆₀ carbocyclic group being a trivalent group or a tetravalent group.

As used herein, the C ₁ -C ₆₀ heterocyclic group has the same structure as the C ₅ -C ₆₀ carbocyclic group, but as ring-forming atoms, in addition to carbon (carbon number may be 1 to 60), N , refers to a group containing at least one hetero atom selected from O, Si, P and S.

As used herein, the substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₁ -C ₆₀ heterocyclic group, substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkyl Len group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted Divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, Substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ hetero Cycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted 1 At least one of the substituents of the divalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ - C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group substituted with at least one selected from among;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic group -aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O) (Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C substituted with at least one selected from ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from,

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amine Dino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C 2 -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C _{3 -C 10} cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic It may be selected from a condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, and a terphenyl group.

In this specification, “Ph” refers to a phenyl group, “Me” refers to a methyl group, “Et” refers to an ethyl group, “ter-Bu” or “Bu ^t ” refers to a tert-butyl group, and “OMe " means a methoxy group.

As used herein, “biphenyl group” means “a phenyl group substituted with a phenyl group.” The “biphenyl group” belongs to the “substituted phenyl group” in which the substituent is a “C ₆ -C ₆₀ aryl group”.

As used herein, “terphenyl group” means “a phenyl group substituted with a biphenyl group.” The “terphenyl group” belongs to the “substituted phenyl group” in which the substituent is a “C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group.”

In this specification, * and *' refer to bonding sites with neighboring atoms in the corresponding chemical formula, unless otherwise defined.

Hereinafter, a compound and an organic light-emitting device according to an embodiment of the present invention will be described in more detail through synthesis examples and examples. In the following synthesis example, in the expression "B was used instead of A," the molar equivalent of A and the molar equivalent of B are the same.

[Example]

Synthesis Example 1: Synthesis of Compound H1

Synthesis of intermediate (A-1)

Under argon atmosphere, 22.0 g of 2,3-dimethoxyphenyl boronic acid, 17.5 g of 1-bromo-2-fluoronaphthalene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane. and 150 mL of 2M sodium carbonate aqueous solution were added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 23.9 g of intermediate (A-1) (yield: 84.8%).

Synthesis of intermediate (A-2)

Under an argon atmosphere, 23.9 g of intermediate (A-1) and 500 mL of anhydrous THF were added to the flask, 60 mL of a hexane solution of 1.6 M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. This was cooled to -78°C, and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 18.0 g of intermediate (A-2) (yield: 65.1 %).

Synthesis of intermediate (A-3)

Under argon atmosphere, 18.0 g of intermediate (A-2), 16.6 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of tetrakis(triphenylphosphine)palladium (0), 180 mL of toluene and 2M 90 mL of sodium carbonate aqueous solution was added to the flask and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain Intermediate (A-3) 19.2g (yield: 76.8%).

Synthesis of intermediate (A-4)

19.2 g of intermediate (A-3) and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of boron tribromide (BBr ₃ ) was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and quenched with methanol and water. The solution was transferred to a separating funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short column of silica gel, the solution was concentrated, and the resulting sample was vacuum-dried, yielding 17.9 g of intermediate (A-4). (yield: 99.5%) was obtained.

Synthesis of intermediate (A)

17.9 g of intermediate (A-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated), and 24.5 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. The mixed solution was dried with MgSO ₄ and impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.8 g of intermediate (A) (yield: 66.3%).

Synthesis of intermediate (H1-1)

38.7 g of intermediate (A) and 500 mL of tetrahydrofuran (dehydrated) were added to the flask and cooled to -78°C. Here, 66 mL of n-BuLi (1.6M in hexane) was added and the temperature was raised to 0°C and stirred for 2 hours. Then, it was cooled again to -78°C, 27.5 g of B(OMe) ₃ was added, and the mixture was stirred at -78°C for 10 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, 200 mL of 1N HCl aqueous solution was added and stirred at room temperature for 1 hour. Then, it was transferred to a separatory funnel and extracted with ethyl acetate. The solution was dried with MgSO ₄ and washed with concentrated n-hexane to obtain 22.9 g of intermediate (H1-1) (yield: 64.9%).

Synthesis of intermediate (H1-2)

Under an argon atmosphere, 22.9 g of intermediate (H1-1), 19.8 g of 1-bromo-4-iodobenzene, 1.52 g of tetrakis (triphenylphosphine) palladium (0), 200 mL of toluene, and 100 mL of 2M sodium carbonate aqueous solution were added. It was placed in a flask and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 24.0 g of intermediate (H1-2) (yield: 72.4%).

Synthesis of Compound H1

Under argon atmosphere, 24.0 g of intermediate (H1-2), 16.4 g of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid, 1.28 g of tetrakis(triphenylphosphine)palladium (0), 180 mL of 1,2-dimethoxyethane and 90 mL of 2M sodium carbonate aqueous solution were added to the flask and stirred under reflux for 8 hours. After cooling to room temperature, the precipitated solid was separated by filtration. The obtained solid was washed with water and methanol and recrystallized with toluene to obtain 21.2 g of compound H1 (yield: 65.8%). Molecular weight = 686.81, m/e = 686.22

Synthesis Example 2: Synthesis of Compound H2

Synthesis of intermediate (B-1)

Under argon atmosphere, 20.3 g of 2,3-bis(methylthio)phenyl boronic acid, 22.5 g of 1-bromo-2-fluoronaphthalene, 2.34 g of tetrakistriphenylphosphine palladium (0), 1,2-dimeth 300 mL of oxyethane and 150 mL of 2M sodium carbonate aqueous solution were added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 26.8 g of intermediate (B-1) (yield: 85.2%).

Synthesis of intermediate (B-2)

Under an argon atmosphere, 26.8 g of intermediate (B-1) and 500 mL of anhydrous THF were placed in a flask, 55 mL of a 1.6 M hexane solution of n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The reaction solution was cooled to -78°C, and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added thereto. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether to remove the aqueous layer, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 19.7 g of intermediate (B-2) (yield: 64.5 %).

Synthesis of intermediate (B-3)

Under argon atmosphere, 19.7 g of intermediate (B-2), 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of tetrakis(triphenylphosphine) palladium (0), 180 mL of toluene and 2M 95 mL of sodium carbonate aqueous solution was added to the flask and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 20.3 g of intermediate (B-3) (yield: 75.9%).

Synthesis of intermediate (B-4)

20.3 g of intermediate (B-3) and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. Here, 27.5 g of BBr ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and quenched with methanol and water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short column of silica gel, the solution was concentrated, and the obtained sample was dried under vacuum, resulting in 19.0 g of intermediate (B-4) (yield: 99.5%). got it

Synthesis of intermediate (B)

19.0 g of intermediate (B-4), 300 mL of N-methyl-2-pyrrolidone, and 24.5 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, transferred to a separatory funnel, and washed with water. The mixed solution was dried with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 11.4 g of intermediate (B) (yield: 65.8%).

Synthesis of intermediate (H2-1)

24.5 g (yield: 63.8%) of intermediate (H2-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (B) was used instead of intermediate (A). .

Synthesis of intermediate (H2-2)

24.9 g of intermediate (H2-2) was produced using the same method as the synthesis method of intermediate (H1-2), except that intermediate (H2-1) was used instead of intermediate (H1-1) (yield: 71.9). %) was obtained.

Synthesis of compound H2

21.1 g (yield: 64.1%) of compound H2 was obtained using the same method as the synthesis method for compound H1, except that intermediate (H2-2) was used instead of intermediate (H1-2). Molecular weight = 718.93, m/e = 718.18

Synthesis Example 3: Synthesis of Compound H3

Synthesis of intermediate (C-1)

Under argon atmosphere, 10.3 g of 9-iodonaphtho[1,2-b]benzofuran, 8.2 g of 2-(ethoxycarbonyl)-5-bromophenylboronic acid, tetrakis(triphenylphosphite) palladium ( 0) A mixture of 0.4g, 30mL of 2M sodium carbonate aqueous solution and 60mL of toluene was heated and refluxed for 8 hours. The resulting mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 8.9g of intermediate (C-1) (yield: 66.8%).

Synthesis of intermediate (C-2)

Under an argon atmosphere, 30 mL of a 1 M tetrahydrofuran solution of methyl magnesium bromide was added to a 90 mL solution of 8.9 g of intermediate (C-1) in tetrahydrofuran under ice-cooling, and stirred at room temperature for 5 hours. Ice water was added to the reaction solution, extracted with toluene, and the organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 6.5 g of intermediate (C-2) (yield: 75.4%).

Synthesis of intermediate (C)

0.7 mL of sulfuric acid was added to a solution of 6.5 g of intermediate (C-2) in 70 mL of acetic acid and stirred at 50°C for 8 hours. The resulting mixture was cooled to room temperature, toluene and water were added to separate the layers, the toluene layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by chromatography to obtain 2.2 g of intermediate (C) (yield: 35.6%).

Synthesis of compound H3

4.5 g of compound H3 (yield: 63.8%) was obtained using the same method as the synthesis method for compound H1, except that intermediate (C) was used instead of intermediate (H1-2). Molecular weight = 636.79, m/e = 636.25

Synthesis Example 4: Synthesis of Compound H4

Synthesis of intermediate (D-1)

Under argon atmosphere, 17.3 g of 2,3-dimethoxyphenyl boronic acid, 22.5 g of 2-bromo-3-fluoronaphthalene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane. and 150 mL of 2M sodium carbonate aqueous solution were added to the flask, heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 22.3 g of intermediate (D-1) (yield: 83.4%).

Synthesis of intermediate (D-2)

Under an argon atmosphere, 22.3 g of intermediate (D-1) and 500 mL of anhydrous THF were placed in a flask, 55 mL of a 1.6 M hexane solution of n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. This was cooled to -78°C, and a solution of 28.2 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 16.8 g of intermediate (D-2) (yield: 65.2%).

Synthesis of intermediate (D-3)

Under argon atmosphere, 16.8 g of intermediate (D-2), 16.8 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of tetrakis(triphenylphosphine)palladium (0), 180 mL of toluene and 2M 90 mL of sodium carbonate aqueous solution was added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 18.4 g of intermediate (D-3) (yield: 78.5 %).

Synthesis of intermediate (D-4)

18.4 g of intermediate (D-3) and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.8 g of BBr ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78°C and quenched with methanol and water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short column of silica gel, the solution was concentrated, and the obtained sample was dried under vacuum, yielding 17.2 g of intermediate (D-4) (yield: 99.7%). ) was obtained.

Synthesis of intermediate (D)

17.2 g of intermediate (D-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated), and 24.5 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. The mixed solution was dried with MgSO ₄ and impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.4 g of intermediate (D) (yield 66.6%).

Synthesis of intermediate (H4-1)

Intermediate (H4-1) was prepared using the same method as the synthesis method for intermediate (H1-1), except that intermediate (D) was used instead of intermediate (A).

intermediate ( H4 -2) Synthesis of

Intermediate (H4-1) was used instead of intermediate (H1-1), and 1-bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene ( Intermediate (H4-2) was prepared using the same method as the synthesis method for H1-2).

Synthesis of compound H4

Intermediate (H4-2) was used instead of intermediate (H1-2), and 9-phenylanthracen-10-yl-10-boronic acid was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 5.8 g (yield: 65.2%) of compound H4 was obtained using the same method as the synthesis method for compound H1, except that . Molecular weight = 636.75, m/e = 636.21

Synthesis Example 5: Synthesis of Compound H5

Intermediate (A) was used instead of intermediate (H1-2), and 9-(3-(naphthalen-1-yl)phenyl)anthracene was used instead of 9-(naphthalen-3-yl)anthracene-10-yl-10-boronic acid. 4.8 g (yield: 63.6%) of compound H5 was obtained using the same method as the synthesis method for compound H1, except that -10-yl-10-boronic acid was used. Molecular weight = 686.81, m/e = 686.22

Synthesis Example 6: Synthesis of Compound H6

Synthesis of intermediate (E-1)

Under argon atmosphere, 17.3 g of 2,4-dimethoxyphenyl boronic acid, 22.5 g of 1-bromo-2-fluoronaphthalene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane. and 150 mL of 2M sodium carbonate aqueous solution were added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 22.5 g of intermediate (E-1) (yield: 84.1%).

Synthesis of intermediate (E-2)

Under an argon atmosphere, 22.5 g of intermediate (E-1) and 500 mL of anhydrous THF were added to a flask, 55 mL of a hexane solution of 1.6 M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. This was cooled to -78°C, and a solution of 27.9 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while warming to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted using ether to remove the aqueous layer, and then the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 17.1 g of intermediate (E-2) (yield: 65.6%).

Synthesis of intermediate (E-3)

Under argon atmosphere, 17.1 g of intermediate (E-2), 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of tetrakis(triphenylphosphine)palladium (0), 180 mL of toluene and 2M 90 mL of sodium carbonate aqueous solution was added to the flask and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 18.4 g of intermediate (E-3) (yield 77.2%).

Synthesis of intermediate (E-4)

18.4 g of intermediate (E-3) and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of BBr ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78°C and quenched with methanol and water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short column of silica gel, the solution was concentrated, and the resulting sample was vacuum dried, resulting in 17.2 g of intermediate (E-4) (yield 99.8%). got it

Synthesis of intermediate (E)

17.2 g of intermediate (E-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated), and 24.2 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. The mixed solution was dried with MgSO ₄ and impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.3 g of intermediate (E) (yield 66.2%).

Synthesis of intermediate (H6-1)

5.7 g (yield: 64.3%) of intermediate (H6-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (E) was used instead of intermediate (A). .

Synthesis of intermediate (H6-2)

The intermediate (H6-1) was used instead of intermediate (H1-1), and 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene. 6.5 g (yield: 72.3%) of intermediate (H6-2) was obtained using the same method as the synthesis method for H1-2).

Synthesis of compound H6

Intermediate (H6-2) was used instead of intermediate (H1-2), and 9-phenylanthracen-10-yl-10-boronic acid was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 5.3 g (yield: 65.8%) of compound H6 was obtained using the same method as the synthesis method for compound H1, except that . Molecular weight = 686.81, m/e = 686.22

Synthesis Example 7: Synthesis of Compound H7

Synthesis of intermediate (F-1)

Under argon atmosphere, 20.3 g of 2,4-bis(methylthio)phenyl) boronic acid, 22.5 g of 1-bromo-2-fluoronaphthalene, 2.32 g of tetrakistriphenylphosphine palladium(0), 1,2- 300 mL of dimethoxyethane and 150 mL of 2M sodium carbonate aqueous solution were added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 25.7 g of intermediate (F-1) (yield: 86.2%).

Synthesis of intermediate (F-2)

Under an argon atmosphere, 25.7 g of intermediate (F-1) and 500 mL of anhydrous THF were placed in a flask, 55 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. This was cooled to -78°C and a solution of 28.2 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 19.0 g of intermediate (F-2) (yield: 64.8%).

Synthesis of intermediate (F-3)

Under argon atmosphere, 19.0 g of intermediate (F-2), 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of tetrakis(triphenylphosphine)palladium (0), 180 mL of toluene and 2M 90 mL of sodium carbonate aqueous solution was added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 19.6 g of intermediate (F-3) (yield 76.1%).

Synthesis of intermediate (F-4)

19.6 g of intermediate (F-3) and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of BBr ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78°C and quenched with methanol and water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and the resulting sample was vacuum dried to obtain 18.4 g of intermediate (F-4) (yield: 99.4%). got it

Synthesis of intermediate (F)

18.4 g of intermediate (F-4), 300 mL of N N-methyl-2-pyrrolidone (dehydrated), and 24.2 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. The mixed solution was dried with MgSO ₄ and impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 2g of Intermediate (F) 11. (yield 66.9%).

Synthesis of intermediate (H7-1)

6.1 g (yield: 63.6%) of intermediate (H7-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (F) was used instead of intermediate (A). .

Synthesis of intermediate (H7-2)

The intermediate (H7-1) was used instead of intermediate (H1-1), and 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene. Using the same method as the synthesis method for H1-2), 6.8 g (yield: 71.8%) of intermediate (H7-2) was obtained.

Synthesis of compound H7

Intermediate (H7-2) was used instead of intermediate (H1-2), and 9-phenylanthracen-10-yl-10-boronic acid was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 5.2 g (yield: 63.5%) of compound H7 was obtained using the same method as the synthesis method for compound H1, except that . Molecular weight = 718.93, m/e 718.18

Synthesis Example 8: Synthesis of Compound H8

Synthesis of intermediate (G-1)

Under argon atmosphere, 10.8 g of 9-iodobenzo[b]naphtho[1,2-d]thiophene, 8.2 g of 2-(ethoxycarbonyl)-5-bromophenylboronic acid, tetrakis(triphenyl A mixture of 0.4 g of phosphite) palladium (0), 30 mL of 2M aqueous sodium carbonate solution, and 60 mL of toluene was heated and refluxed for 8 hours. The resulting mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 9.1 g of intermediate (G-1) (yield: 65.7%).

Synthesis of intermediate (G-2)

Under an argon atmosphere, 30 mL of a 1 M tetrahydrofuran solution of methyl magnesium bromide was added to a 90 mL solution of 9.1 g of intermediate (G-1) in tetrahydrofuran under ice cooling, and stirred at room temperature for 5 hours. Ice water was added to the reaction solution, extracted with toluene, and the organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 6.6 g of intermediate (G-2) (yield: 75.2%).

Synthesis of intermediate (G)

0.7 mL of sulfuric acid was added to a solution of 6.6 g of intermediate (G-2) in 70 mL of acetic acid and stirred at 50°C for 8 hours. The resulting mixture was cooled to room temperature, toluene and water were added to separate the layers, the toluene layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by chromatography to obtain 2.2 g of intermediate (G) (yield 35.2%).

Synthesis of intermediate (H8-1)

1.2 g (yield: 63.6%) of intermediate (H8-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (G) was used instead of intermediate (A). .

Synthesis of intermediate (H8-2)

The intermediate (H8-1) was used instead of intermediate (H1-1), and 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene. 1.4 g (yield: 72.0%) of intermediate (H8-2) was obtained using the same method as the synthesis method for H1-2).

Synthesis of compound H8

Intermediate (H8-2) was used instead of intermediate (H1-2), and 9-phenylanthracen-10-yl-10-boronic acid was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 1.1 g of compound H8 (yield: 63.3%) was obtained using the same method as the synthesis method for compound H1, except that . Molecular weight = 728.95, m/e 728.25

Synthesis example 9: Compound H9 synthesis of

Synthesis of intermediate (H-1)

Under argon atmosphere, 20.3 g of 2,4-bis(methylthio)phenyl boronic acid, 22.5 g of 2-bromo-3-fluoronaphthalene, 2.34 g of tetrakistriphenylphosphine palladium (0), 1,2-dimeth 300 mL of oxyethane and 150 mL of 2M sodium carbonate aqueous solution were added to the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 26.6 g of intermediate (H-1) (yield: 84.6%).

Synthesis of intermediate (H-2)

Under an argon atmosphere, 26.6 g of intermediate (H-1) and 500 mL of anhydrous THF were placed in a flask, 55 mL of a 1.6M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. The reaction solution was cooled to -78°C, and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added thereto. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether to remove the aqueous layer, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 19.2 g of intermediate (H-2) (yield: 63.2%).

Synthesis of intermediate (H-3)

Under argon atmosphere, 19.2 g of intermediate (H-2), 16.5 g of 4-bromo-2-fluoro-1-iodobenzene, 1.28 g of tetrakis(triphenylphosphine)palladium (0), 180 mL of toluene, and 95 mL of 2M sodium carbonate aqueous solution was added to the flask and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 20.0 g of intermediate (H-3) (yield: 74.8%).

Synthesis of intermediate (H-4)

20.0 g of intermediate (H-3) and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. Here, 27.5 g of BBr ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and quenched with methanol and water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short column of silica gel, the solution was concentrated, and the obtained sample was dried under vacuum, resulting in 18.7 g of intermediate (H-4) (yield: 99.5%). got it

Synthesis of intermediate (H)

18.7 g of intermediate (H-4), 300 mL of N-methyl-2-pyrrolidone, and 24.5 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, transferred to a separatory funnel, and washed with water. The mixed solution was dried with MgSO ₄ and impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 11.3 g of intermediate (H) (yield: 65.8%).

Synthesis of compound H9

Intermediate (H) was used instead of intermediate (H1-2), and 9-(9,9-dimethyl-9H-fluorene-3 was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 12.3 g of compound H9 was obtained using the same method as the synthesis method for compound H1, except that -yl)anthracen-10-yl-10-boronic acid was used. Molecular weight = 708.94, m/e = 708.19

Example 1

As the substrate and anode, a corning 15Ω/cm2 (1200Å) ITO glass substrate was cut into 50mm Then, the glass substrate was exposed to ozone, cleaned, and installed in a vacuum deposition device.

Compound HT13 was vacuum deposited on top of the ITO anode to form a hole injection layer with a thickness of 500 Å, and compound HT3 was vacuum deposited on top of the hole injection layer to form a hole transport layer with a thickness of 450 Å.

Compound H1 (host) and FD1 (dopant) were co-deposited on the top of the hole transport layer at a weight ratio of 95:5 to form a light emitting layer with a thickness of 300 Å.

Compound ET1 was deposited on top of the light emitting layer to form an electron transport layer with a thickness of 250 Å, LiF was deposited on top of the electron transport layer to form an electron injection layer with a thickness of 50 Å, and Al was vacuum deposited on top of the electron injection layer to form a 1,500 Å thick layer. An organic light-emitting device was manufactured by forming a cathode.

Examples 2 to 9 and Comparative Examples 1 to 4

An organic light-emitting device was manufactured using the same method as Example 1, except that the compounds listed in Table 1 were used to form the light-emitting layer.

Evaluation example 1

Efficiency and lifespan (T ₈₀ ) data of the organic light emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 to 4 were measured using Kethley SMU 236 and a luminance meter PR650, and the results are shown in Table 1. Lifespan (T ₈₀ ) is a measure of the time it takes for the luminance to become 80% of the initial luminance (100%) after driving the device at a current density of 50 mA/cm ² .

host material efficiency
(cd/A) Lifespan (T ₈₀ )
(hr@50mA/cm ² ) Example 1 H1 5.2 100 Example 2 H2 5.1 90 Example 3 H3 5.3 80 Example 4 H4 5.1 100 Example 5 H5 5.1 100 Example 6 H6 5.0 110 Example 7 H7 5.0 90 Example 8 H8 5.2 90 Example 9 H9 5.1 100 Comparative Example 1 Compound A 4.5 50 Comparative Example 2 Compound B 4.7 80 Comparative Example 3 Compound C 4.9 70 Comparative Example 4 Compound D 5.0 90

From Table 1, it can be seen that the efficiency and lifespan of the organic light-emitting devices of Examples 1 to 9 are superior to those of the organic light-emitting devices of Comparative Examples 1 to 4.

10, 20, 30, 40: Organic light emitting device
110: first electrode
150: Organic layer
190: second electrode
210: first capping layer
220: second capping layer

Claims (20)

Condensed ring compound represented by the following formula 1-1 or 1-2:
<Formula 1-1>

<Formula 1-2>

In formulas 1-1 and 1-2,
A ₁ ring is benzene,
A ₂ ring is naphthalene,
X ₁ and X ₂ are independently selected from O and S,
R ₃ is independently hydrogen or deuterium (-D),
R ₄ is independently hydrogen or deuterium (-D),
One of R ₅ is a group represented by the following formula 2A(1), and the other is hydrogen or deuterium (-D),
<Formula 2A(1)>

In Formula 2A(1),
L ₁ and L ₂ are independently selected from substituted or unsubstituted C ₆ -C ₆₀ arylene groups,
a1 and a2 are independently selected from 0, 1, 2, and 3,
Ar _1e is selected from a substituted or unsubstituted C ₆ -C ₆₀ aryl group,
* is a binding site with a neighboring atom,
b3 is selected from an integer of 1 to 10, b4 is 1 or 2, b5 is selected from an integer of 1 to 4,
At least one of the substituents of the substituted C ₆ -C ₆₀ arylene group and the substituted C ₆ -C ₆₀ aryl group is,
Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ - C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group substituted with at least one selected from among;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic group -aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O) (Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C substituted with at least one selected from ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );
is selected from,
Q ₁ to Q ₉ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group , a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, and a terphenyl group,
* is a bonding site with a neighboring atom. delete delete According to paragraph 1,
In formulas 1-1 and 1-2,
X ₁ and X ₂ are S;
X ₁ is O and X ₂ is S;
X ₁ and X ₂ are O; or
A condensed ring compound in which X ₁ is S and X ₂ is O; delete delete According to paragraph 1,
In Formula 2A(1),
The L ₁ and L ₂ are each independently selected from a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, and a hepthalenylene group ( heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenyl Phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, Naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, and ovalenylene; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylgyrenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylgyrenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group. , a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, substituted with at least one of a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, and an azulenylene group. , hepthalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, Anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenylene group , coronenylene group, and ovalenylene group; Condensed ring compounds selected from among. According to paragraph 1,
In Formula 2A(1), L ₁ and L ₂ are each independently selected from the group represented by Formulas 3-1 to 3-12 and Formulas 3-15 to 3-22:

Among Formulas 3-1 to 3-12 and Formulas 3-15 to 3-22,
Y ₁ is C(Z ₃ )(Z ₄ ),
Z ₁ to Z ₄ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, selected from anthracenyl group, pyrenyl group, chrysenyl group, carbazolyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),
Q ₃₁ to Q ₃₃ are independently selected from C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group,
d1 is selected from an integer of 1 to 4, d2 is selected from an integer of 1 to 3, d3 is selected from an integer of 1 to 6, d4 is selected from an integer of 1 to 8, and d5 is selected from an integer of 1 to 5. is selected from among integers, and * and *' are bonding sites with neighboring atoms. According to paragraph 1,
In Formula 2A(1), L ₁ and L ₂ are independently selected from the group represented by Formulas 4-1 to 4-19, Formulas 4-23, Formulas 4-27, and Formulas 4-33, Condensed ring compounds:

In Formulas 4-1 to 4-19, Formulas 4-23, Formulas 4-27, and Formulas 4-33, * and *' are bonding sites with neighboring atoms. According to paragraph 1,
In Formula 2A(1), a1 and a2 are independently 0 or 1, a condensed ring compound. According to paragraph 1,
In Formula 2A(1), Ar _1e is,
Phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group , hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group and ovalenyl group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group. , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, substituted with at least one selected from benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ). Nyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group , anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group and ovalenyl group; is selected from,
Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group. According to paragraph 1,
In Formula 2A(1), Ar _1e is,
Condensed ring compounds selected from the group represented by the following formulas 5-1 to 5-16:

In formulas 5-1 to 5-16,
Y ₃₁ is selected from O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) and Si(Z ₃₆ )(Z ₃₇ ),
Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group , chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrethyl group. Phenyl group, biphenyl group, terphenyl group, naphthyl group substituted with at least one selected from the group consisting of nyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group. , fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group. , carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; is selected from,
e3 is selected from integers 1 to 3, e4 is selected from integers 1 to 4, e5 is selected from integers 1 to 5, e6 is selected from integers 1 to 6, and e7 is selected from integers 1 to 7. is selected from an integer, and e9 is selected from an integer of 1 to 9. According to paragraph 1,
In Formula 2A(1), Ar _1e is,
Condensed ring compounds selected from the group represented by the following formulas 6-1 to 6-44:

In Formulas 6-1 to 6-44, * is a bonding site with a neighboring atom. delete delete According to paragraph 1,
A condensed ring compound represented by one of the following formulas 1 (1) to 1 (8):
<Formula 1(1)>

<Formula 1(2)>

<Formula 1(3)>

<Formula 1(4)>

<Formula 1(5)>

<Formula 1(6)>

<Formula 1(7)>

<Formula 1(8)>

In the formulas 1 (1) to 1 ( _{8 ) ,} A _{1 ,} A _{2 ,} X ₁ , And R _5a to R _5c are independently hydrogen or deuterium (-D), and Ar _1a to Ar _1d and Ar _1f to Ar _1i are hydrogen. According to paragraph 1,
A condensed ring compound represented by one of the following formulas 1(1)-1 to 1(7)-1:
<Formula 1(1)-1>

<Formula 1(2)-1>

<Formula 1(3)-1>

<Formula 1(4)-1>

<Formula 1(5)-1>

<Formula 1(6)-1>

<Formula 1(7)-1>

In the above formulas 1(1)-1 to 1(7)-1, A ₁ , A ₂ , X ₁ , X ₂ , L ₁ , L ₂ , a1 and a2 are the same as described in claim 1. first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer includes one or more of the condensed ring compounds of claim 1. According to clause 18,
The light-emitting layer is an organic light-emitting device comprising the condensed cyclic compound. According to clause 19,
An organic light-emitting device wherein the light-emitting layer further includes a fluorescent dopant.