KR102057585B1 - Organic light-emitting device - Google Patents

Abstract

<화학식 2>

<화학식 3>

A first electrode; A second electrode opposed to the first electrode; A light emitting layer interposed between the first electrode and the second electrode; An electron transport region interposed between the light emitting layer and the second electrode; A hole transport region interposed between the first electrode and the light emitting layer; The electron transport region includes at least one selected from an electron transport material represented by Formula 1 below; Disclosed is an organic light-emitting device comprising at least one member selected from among a hole transport material represented by Formula 2 or 3 below:
<Formula 1>

<Formula 2>

<Formula 3>

Description

Organic light-emitting device

Embodiments of the present invention relate to an organic light emitting device.

The organic light-emitting device is a self-luminous device, which has a wide viewing angle and excellent contrast, fast response time, excellent luminance, driving voltage and response speed, and multicolorization. .

In the organic light emitting diode, a first electrode is disposed on a substrate, and a hole transport region, an emission 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 emission layer to generate excitons. The excitons change from excited state to ground state and light is generated.

Embodiments of the present invention provide an organic light emitting device.

One embodiment of the invention the first electrode; A second electrode opposed to the first electrode; A light emitting layer interposed between the first electrode and the second electrode;

An electron transport region interposed between the light emitting layer and the second electrode;

A hole transport region interposed between the first electrode and the light emitting layer;

The electron transport region includes at least one selected from an electron transport material represented by Formula 1 below;

The hole transport region discloses an organic light emitting device including at least one selected from a hole transport material represented by Formula 2 or 3 below:

<Formula 1>

<Formula 2>

<Formula 3>

In Formulas 1 to 3,

X ₁₁ , X ₁₂ and X ₁₃ are, independently from each other, CH or N;

At least one of X ₁₁ , X ₁₂ and X ₁₃ is N;

L ₁₁ , L ₁₂ and L ₂₁ to L ₂₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₂ -C ₆₀ hetero Arylene groups, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups (substituted or unsubstituted divalent non-aromatic condensed polycyclic groups) and substituted or unsubstituted divalent non-aromatic condensed polycyclic groups (substituted or unsubstituted divalent non- aromatic hetero-condensed polycyclic group);

n11, n12 and n21 to n23 are each independently selected from an integer of 0 to 3;

the sum of n11 and n12 is at least 1;

R ₁₁ to R ₁₃ , R ₂₁ to R ₂₄ and R ₃₁ to R ₃₅ are each independently,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof , Phosphoric acid group or salt thereof, 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or Unsubstituted C ₂ -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, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group, a substituted or unsubstituted 1 is a non-aromatic heterocyclic is selected from condensed polycyclic group;

a13 is an integer of 1 to 3;

R ₂₅ to R ₂₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group Or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -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, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and -B (Q ₆ (Q ₇ );

a25 and a27 are each independently selected from an integer of 1 to 3;

a26 and a28 are each independently selected from an integer of 1 to 4;

The substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloalkenylene group, substitution C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C ₃ -C ₁₀ Cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C _6- C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₂ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic heterocondensation At least _{one of the} substituents of the polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group and substituted C ₁ -C ₆₀ alkoxy group,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) And C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocyclo substituted with at least one of —B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Teroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed polycyclic groups; And

-N (Q ₃₁ ) (Q ₃₂ ), -Si (Q ₃₄ ) (Q ₃₅ ) (Q ₃₆ ) and -B (Q ₃₇ ) (Q ₃₈ ); Is selected from;

Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ , Q ₃₁ , Q ₃₂ and Q ₃₃ to Q ₃₇ are each independently hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group , C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group.

The organic light emitting diode according to the embodiments of the present invention may have a low driving voltage, high brightness and high efficiency.

1 is a schematic cross-sectional view of a structure of an organic light emitting diode according to an exemplary embodiment.

As the invention allows for various changes and numerous embodiments, particular embodiments will be illustrated in the drawings and described in detail in the written description. Effects and features of the present invention, and methods of achieving them will be apparent with reference to the embodiments described below in detail together with the drawings. However, the present invention is not limited to the embodiments disclosed below but may be implemented in various forms.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings, and the same or corresponding components will be denoted by the same reference numerals, and redundant description thereof will be omitted. .

In the following examples, the terms including or having have meant that there is a feature or component described in the specification and does not preclude the possibility of adding one or more other features or components.

In the following embodiments, when a part such as a film, a region, a component, or the like is on or on another part, not only is it directly above the other part, but also another film, a region, a component, etc. is interposed therebetween. This includes any case.

In the drawings, components may be exaggerated or reduced in size for convenience of description. For example, the size and thickness of each component shown in the drawings are arbitrarily shown for convenience of description, and thus the present invention is not necessarily limited to the illustrated.

In the present specification, "(organic layer) includes at least one compound represented by formula (1)" means "(organic layer) one compound belonging to the category of formula (1) or two different from the category of formula (1) May include more than one compound ".

As used herein, the term "organic layer" refers to all layers of a single and / or a plurality of organic light emitting devices interposed between the first electrode and the second electrode. The material included in the layer of the "organic layer" is not limited to the organic material.

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

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

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

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

The first electrode 110 may be formed by, for example, providing a material for the first electrode on the substrate by using a deposition method or a sputtering method. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used as the material for the first electrode. Alternatively, in order to form the first electrode 110, which is a semi-transmissive electrode or a reflective electrode, as a material for the first electrode, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca) ), Magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) may be selected.

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

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

The organic layer 150 may further include a hole transport region interposed between the first electrode and the light emitting layer. The organic layer 150 may further include an electron transport region interposed between the emission layer and the second electrode.

The hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer and an electron blocking layer (EBL), and the electron transport region may be a hole blocking layer (HBL) or an electron transport layer. At least one of an ETL and an electron injection layer EIL may be included, but is not limited thereto.

The hole transport region may have a multilayer structure having a single layer made of a single material, a single layer made of a plurality of different materials, or a plurality of layers made of a plurality of different materials.

For example, the hole transport region may have a single layer structure composed of a plurality of different materials, or may be sequentially stacked from the first electrode 110, and may be a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / buffer layer. It may have a structure of a hole injection layer / buffer layer, a hole transport layer / buffer layer or a hole injection layer / hole transport layer / electron blocking layer, but is not limited thereto.

When the hole transport region includes a hole injection layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI) The hole injection layer may be formed on the first electrode 110 using various methods such as the above.

When the hole injection layer is formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500 ° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and about 0.01 to about 100 Pa / sec. Within the deposition rate range of, it may be selected in consideration of the compound for the hole injection layer to be deposited and the hole injection layer structure to be formed.

When the hole injection layer is formed by spin coating, the coating conditions are within the coating rate of about 2000 rpm to about 5000 rpm and the heat treatment temperature range of about 80 ° C. to 200 ° C., the compound for the hole injection layer to be deposited and the hole to be formed. It may be selected in consideration of the injection layer structure.

The hole injection layer is m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB, TAPC, HMTPD, TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine))

When the hole transport region includes a hole transport layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc. Using the same various methods, the hole transport layer may be formed on the first electrode 110 or on the hole injection layer. When the hole transport layer is formed by vacuum deposition or spin coating, deposition and coating conditions for the hole transport layer may be similar to the deposition and coating conditions for the hole injection layer.

The hole transport region may include at least one selected from a hole transport material represented by the following Chemical Formula 2 or 3. For example, a hole transport material represented by Formula 2 or 3 can be included in the hole transport layer:

<Formula 2>

<Formula 3>

In Formulas 2 and 3,

L ₂₁ to L ₂₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group, substituted or unsubstituted Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and Substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group );

n21 to n23 are each independently selected from an integer of 0 to 3;

R ₂₁ to R ₂₄ and R ₃₁ to R ₃₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group or hydrazine group , Hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C _6- C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1 is a non-condensed polycyclic aromatic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from the condensed polycyclic group;

R ₂₅ to R ₂₈ independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -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, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and -B (Q ₆ (Q ₇ );

a25 and a27 are each independently selected from an integer of 1 to 3;

a26 and a28 are each independently selected from an integer of 1 to 4;

The substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloalkenylene group, substitution C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C ₃ -C ₁₀ Cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C _6- C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₂ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic heterocondensation At least _{one of the} substituents of the polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group and substituted C ₁ -C ₆₀ alkoxy group,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) And C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocyclo substituted with at least one of —B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Teroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed polycyclic groups; And

-N (Q ₃₁ ) (Q ₃₂ ), -Si (Q ₃₄ ) (Q ₃₅ ) (Q ₃₆ ) and -B (Q ₃₇ ) (Q ₃₈ ); Is selected from;

Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ , Q ₃₁ , Q ₃₂ and Q ₃₃ to Q ₃₇ are each independently hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group , C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group.

For example, in Formula 2, L ₂₁ to L ₂₃ may be each independently,

Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene ( acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, naphthacenylene, pisenylene picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, rubicenylene, coronenylene, ovalenylene ovalenylene, pyrrolylene, thienylen e), furanylene, silolylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene , Isoxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, Indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene , Quinoxalinylene, quinazolinylene, quinazolinylene, carnozylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene , Phenazinylene, ben Imidazolylene, benzofuranylene, benzothienylene, benzosilolylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene (isobenzooxazolylene), triazolylene, tetrazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, Benzocarbazolyene, dibenzocarbazolyene and dibenzosilolylene; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, Heptalenyl, indasenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, naphthacenyl, fisenyl, peryllenyl, pentaphenyl, hexasenyl, pentansenyl, rubisenyl, coronyl, ovalenyl, pyrroyl, thienyl, furanyl, silolyl, imida Zolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, py Lidazinyl, isoindoleyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, sinolinyl, Carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, tria Phenylene, pentalenylene, indenylene, substituted with at least one of zolyl, tetrazole, oxdiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl and dibenzosilolyl , Naphthylene, azulenylene, heptalenylene, indasenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenenylene, phenanthrenylene, Anthracenylene, fluoranthhenylene, triphenylenylene, pyrenylene, Chrysenylene, naphthasenylene, fisenylene, peryleneylene, pentaphenylene, hexasenylene, pentansenylene, rubisenylene, coronylene, ovalenylene, pyrroylene, thienylene, furanylene, silol Irene, imidazole ylene, pyrazol ylene, thiazol ylene, isothiazo ylene, oxazol ylene, isoxazol ylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindoleylene, indole ylene , Indazole ylene, furinylene, quinolinilene, isoquinolinyl, benzoquinolinyl, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cynolinylene, carbazoylene, phenantridi Nylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothienylene, benzosilolylene, isobenzothiazoleylene, benzoxazolylene, isobenzooxazolylene, triazole Ylene, tetrazoleylene, oxadiazole ylene, triazinylene, di Division furanoid alkenylene, dibenzo-thio-phenylene, benzo-carbazol-ylene, dibenzo-carbazol-ylene and dibenzo silole ylene; It may be selected from, but is not limited thereto.

As another example, in Formula 2, L ₂₁ to L ₂₃ may be each independently,

Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysenylene, pyridinylene, pyrazinyl Enes, pyrimidinylene, pyridazinylene, quinolinilene, isoquinolinylene, quinoxalinylene, quinazolinylene, carbazolylene and triazinylene; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthra At least one substituted with at least one selected from senyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl , Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysenylene, pyridinylene, pyra Genylene, pyrimidinylene, pyridazinylene, quinolinylene, isoquinolinylene, quinone Salicylate alkenylene, quinazolinyl alkenylene, carbazol-ylene and triazinyl alkylene; It may be selected from, but is not limited thereto.

As another example, in Formula 2, L ₂₁ to L ₂₃ may be each independently selected from Formulas 6-1 to 6-7, but are not limited thereto.

In Chemical Formulas 6-1 to 6-7,

Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, Among phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Selected,

d1 is selected from an integer of 1 to 4;

d3 is selected from an integer of 1 to 6;

d4 is selected from an integer of 1 to 8;

* And ** are binding sites with neighboring atoms.

For example, in Formula 2, n21 to n23 may be each independently an integer of 0 or 1, but are not limited thereto.

As another example, in Formula 2, n21 may be 1, and n22 and n23 may be 0, but embodiments of the present invention are not limited thereto.

For example, in Formula 2, R ₂₃ and R ₂₄ may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, but is not limited thereto.

For example, in Formulas 2 and 3, R ₂₁ and R ₃₁ to R ₃₅ are each independently of each other, phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl , Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; And

Deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, phenanthrenyl, fluorenyl, spiro- Fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl , Phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluore substituted with at least one substituent selected from quinoxalinyl, quinazolinyl, carbazolyl, triazinyl and -N (Q ₃₁ ) (Q ₃₂ ) Nil, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; Is selected from;

Q ₃₁ and Q ₃₂ may be each independently selected from a phenyl group and a naphthyl group, but are not limited thereto.

As another example, in Formulas 2 and 3, R ₂₁ , and R ₃₁ to R ₃₅ may be each independently,

Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; And

Deuterium, halogen atom, cyano, nitro, methyl and at least one substituent selected from methoxy, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and -N (Ph) ₂ Substituted phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; It may be selected from, but is not limited thereto.

For example, in Formula 2, R ₂₂ to R ₂₄ are independently of each other,

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Phenyl, naphthyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, tria Genyl, dibenzofuranyl and dibenzothienyl; And

Deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, Benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl , Phenyl, naphthyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidyl substituted with at least one substituent selected from quinazolinyl, carbazolyl and triazinyl Nil, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; It may be selected from, but is not limited thereto.

As another example, in Formula 2, R ₂₂ to R ₂₄ may be each independently,

Methyl and methoxy;

Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; And

At least one selected from deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, methyl, methoxy, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl substituted with substituents of; It may be selected from, but is not limited thereto.

For example, in Formula 2, R ₂₅ to R ₂₈ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₆₀ alkyl group, and C ₁ -C ₆₀ alkoxy group; It may be selected from, but is not limited thereto.

As another example, in Formula 2, R ₂₅ to R ₂₈ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, cyano group, nitro group, methyl, and methoxy; It may be selected from, but is not limited thereto.

In an embodiment, the hole transport material represented by Chemical Formula 2 may be represented by Chemical Formula 2A, but is not limited thereto.

<Formula 2A>

In Formula 2A,

R ₂₁ to R ₂₈ and a25 to a28 are as described above.

In another embodiment, the hole transport material represented by Formula 2 or 3 may be selected from Compounds 301 to 326, but is not limited thereto.

Since the hole transport material represented by Formula 2 or 3 has excellent hole transport ability, the organic light emitting device including the same has excellent efficiency and lifespan.

The hole transport region may have a thickness of about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa. If the hole transport region includes both a hole injection layer and a hole transport layer, the hole injection layer has a thickness of about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa, and the thickness of the hole transport layer is about 50 kPa to about 1000 kPa. 2000 kV, for example from about 100 kV to about 1500 kV. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

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 heterogeneously dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethe. Quinone derivatives such as phosphorus (F4-TCNQ) and the like; Metal oxides such as tungsten oxide and molybdenum oxide; And the following compound HT-D1, but are not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transport region may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injection layer and the hole transport layer as described above. The buffer layer may serve to increase light emission efficiency by compensating an optical resonance distance according to a wavelength of light emitted from the light emitting layer. As the material included in the buffer layer, a material that may be included in the hole transport region may be used. The electron blocking layer is a layer that serves to prevent electron injection from the electron transport region.

Vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI) on the first electrode 110 or the hole transport region The light emitting layer is formed using various methods such as). When the light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions and the coating conditions of the light emitting layer refer to the deposition conditions and the coating conditions of the hole injection layer.

When the organic light emitting device 10 is a full color organic light emitting device, the organic light emitting device 10 may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each light emitting layer and individual subpixels. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and a blue light emitting layer are stacked, or a red light emitting material, a green light emitting material, and a blue light emitting material are mixed without layer division to emit white light. Alternatively, the light emitting layer may be a white light emitting layer, and may further include a color converting layer for converting the white light into light of a desired color, or a color filter.

The light emitting layer may include a host and a dopant.

The host may comprise at least one of the following TPBi, TBADN, ADN, CBP, CDBP and TCP:

Alternatively, the host may include a compound represented by the following Formula 301.

<Formula 301>

Ar ₃₀₁ -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb2

In Formula 301,

Ar ₃₀₁ silver

Naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorine Lananthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indeno Anthracene (indenoanthracene);

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, non-aromatic condensed polycyclic groups and -Si (Q ₃₀₁ ) ( Q ₃₀₂ ) (Q ₃₀₃ ) (The above Q ₃₀₁ to Q ₃₀₃ are independently of each other hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl Naphthalene, heptylene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, penalene, phenanthrene, anthracene, fluoranthene, triphenylene, pi Ren, Chryssen, I Tasen, pisen, perylene, penta pen and indeno anthracene; Is selected from;

L ₃₀₁ is substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene, substituted or unsubstituted C ₃ -C ₁₀ heterocycloalkylene, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene, substituted or unsubstituted C ₃ -C ₁₀ heterocycloalkenylene, substituted or unsubstituted C ₆ -C ₆₀ arylene, substituted or unsubstituted C ₂ -C ₆₀ heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic ring Group and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group,

Substituted C ₃ -C ₁₀ cycloalkylene, substituted C ₃ -C ₁₀ heterocycloalkylene, substituted C ₃ -C ₁₀ cycloalkenylene, substituted C ₃ -C ₁₀ heterocycloalkenylene, substituted C _{At least one} substituent of _6- C ₆₀ arylene, substituted C ₂ -C ₆₀ heteroarylene, substituted divalent non-aromatic condensed polycyclic group, and substituted divalent non-aromatic condensed polycyclic group,

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C _3- C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₂₀₁ ) (Q ₂₀₂ ), -Si (Q ₂₀₃ ) (Q ₂₀₄ ) (Q ₂₀₅ ) And C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy, substituted with at least one of —B (Q ₂₀₆ ) (Q ₂₀₇ );

C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group;

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic C ₃ −, substituted with at least one of a heterofused polycyclic group, —N (Q ₂₁₁ ) (Q ₂₁₂ ), —Si (Q ₂₁₃ ) (Q ₂₁₄ ) (Q ₂₁₅ ) and —B (Q ₂₁₆ ) (Q ₂₁₇ ) C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic condensed Ring group; And

-N (Q ₂₂₁ ) (Q ₂₂₂ ), -Si (Q ₂₂₃ ) (Q ₂₂₄ ) (Q ₂₂₅ ) and -B (Q ₂₂₆ ) (Q ₂₂₇ ); Is selected from;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, phenyl, naphthyl, fluorenyl, spiro -Fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolin C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy, substituted with at least one selected from nil, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole and triazinyl; And

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ Alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyri Phenyl, naphthyl, fluorenyl, spiro-fluore, substituted with at least one selected from midinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Neyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxyl Salinyl, quinazolinyl, carbazolyl and triazinyl; Is selected from;

xb1 is selected from 0, 1, 2 and 3;

xb2 is selected from 1, 2, 3 and 4.

For example, in Formula 301,

L ₃₀₁ is

Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene and chrysenylene; And

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ phenyl substituted with at least one selected from alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and chrysenyl Ethylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene and chrysenylene; Is selected from;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, phenyl, naphthyl, fluorenyl, spiro C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy substituted with at least one selected from -fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and chrysenyl;

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and chrysenyl; And

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ phenyl substituted with at least one selected from alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and chrysenyl , Naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and chrysenyl; It may be selected from, but is not limited thereto.

For example, the host may include a compound represented by Formula 301A:

<Formula 301A>

For a description of the substituents in the formula 301A refer to the bar described herein.

The compound represented by Formula 301 may include at least one of the following compounds H1 to H42, but is not limited thereto.

Alternatively, the host may include at least one of the following compounds H43 to H49, but is not limited thereto:

The emission layer of the organic light emitting device may further include at least one of a fluorescent dopant and a phosphorescent dopant.

The phosphorescent dopant may include an organometallic complex represented by Formula 401:

<Formula 401>

In Formula 401,

M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and tolium (TM);

X ₄₀₁ to X ₄₀₄ are, independently from each other, a nitrogen atom or a carbon atom;

A ₄₀₁ and A ₄₀₂ ring are independently of each other, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene Substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted furan, substituted or unsubstituted imidazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, Substituted or unsubstituted isothiazole, substituted or unsubstituted oxazole, substituted or unsubstituted isoxazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, Substituted or unsubstituted pyridazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or Unsubstituted carbazole, substituted or unsubstituted benzoimidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted isobenzothiophene, substituted or unsubstituted Benzoxazole, substituted or unsubstituted isobenzooxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran And substituted or unsubstituted dibenzothiophene;

Substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, substituted Substituted thiazole, substituted isothiazole, substituted oxazole, substituted isoxazole, substituted pyridine, substituted pyrazine, substituted pyrimidine, substituted pyridazine, substituted quinoline, substituted isoquinoline, substituted benzo Quinoline, substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzooxazole, substituted iso At least one substituent of benzoxazole, substituted triazole, substituted oxadiazole, substituted triazine, substituted dibenzofuran and substituted dibenzothiophene,

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C _3- C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio (arylthio), C ₂ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₄₀₁ ) (Q ₄₀₂ ), -Si (Q ₄₀₃ ) (Q ₄₀₄ ) (Q ₄₀₅ ) and -B (Q ₄₀₆ ) (Q ₄₀₇ ) substituted with at least one of C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl and non-aromatic condensed polycyclic groups;

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic C ₃ -substituted with at least one of a heterofused polycyclic group, -N (Q ₄₁₁ ) (Q ₄₁₂ ), -Si (Q ₄₁₃ ) (Q ₄₁₄ ) (Q ₄₁₅ ) and -B (Q ₄₁₆ ) (Q ₄₁₇ ) C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic condensed Ring group; And

-N (Q ₄₂₁ ) (Q ₄₂₂ ), -Si (Q ₄₂₃ ) (Q ₄₂₄ ) (Q ₄₂₅ ) and -B (Q ₄₂₆ ) (Q ₄₂₇ ); Is selected from;

L ₄₀₁ is an organic ligand;

xc1 is 1, 2 or 3;

xc2 is 0, 1, 2 or 3.

L ₄₀₁ may be any monovalent, divalent or trivalent organic ligand. For example, L ₄₀₁ is a halogen ligand (e.g. Cl, F), a diketone ligand (e.g. acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g. picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon Monooxide ligands, isonitrile ligands, cyano ligands and phosphorus ligands (eg, phosphine, phosphite) may be selected from, but are not limited thereto.

If the formula of A 401 ₄₀₁ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₁ can form a saturated or unsaturated ring.

If the formula of A 401 ₄₀₂ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₂ can form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A₄₀₁ 및 A₄₀₂는 각각 이웃하는 다른 리간드의 A₄₀₁ 및 A₄₀₂와 각각 직접(directly) 또는 연결기(예를 들면, C₁-C₅알킬렌, -N(R')-(여기서, R'은 C₁-C₁₀알킬기 또는 C₆-C₂₀아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands in Formula 401

May be the same or different from each other. When xc1 in Formula 401 is 2 or more, A ₄₀₁ and A ₄₀₂ may be directly or a linking group (for example, C ₁ -C ₅ alkylene, -N) with A ₄₀₁ and A ₄₀₂ of neighboring other ligands, respectively. And (R ')-, wherein R' is a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₂₀ aryl group or -C (= 0)-).

The phosphorescent dopant may include at least one of the following compounds PD1 to PD75, but is not limited thereto:

The fluorescent dopant may include at least one of the following DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6 and C545T.

Alternatively, the fluorescent dopant may include a compound represented by the following Chemical Formula 501:

<Formula 501>

In Formula 501,

Ar ₅₀₁ silver

Naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorine Lananthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indeno Anthracene (indenoanthracene);

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic Heterocondensed polycyclic group and -Si (Q ₅₀₁ ) (Q ₅₀₂ ) (Q ₅₀₃ ) (The above Q ₅₀₁ to Q ₅₀₃ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl group selected from a) in at least one substitution selected, naphthalene, heptyl talren, fluorene, a spy-fluorene, benzo fluorene, dibenzo fluorene, page nalren, phenanthrene , Anthracene, fluorine Lanten, triphenylene, pyrene, chrysene, naphthacene, pisene, perylene, pentaphene and indenoanthracene; Is selected from;

The descriptions of L ₅₀₁ through L ₅₀₃ refer to the description of L ₃₀₁ , respectively, herein;

R ₅₀₁ and R ₅₀₂ are independently of each other,

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyl and dibenzothiophenyl; And

Deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ Alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyri Phenyl, naphthyl, substituted with at least one selected from midinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl , Fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, Quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, t Azinyl and dibenzo-furanyl and dibenzo-thiophenyl; Is selected from;

xd1 to xd3 are each independently selected from 0, 1, 2, and 3;

xb4 is selected from 1, 2, 3 and 4.

The fluorescent host may comprise at least one of the following compounds FD1 to FD8:

FD9

The content of the dopant in the light emitting layer may be generally selected from 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 light emitting layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 200 kPa to about 600 kPa. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics without a substantial increase in driving voltage.

Next, an electron transport region may be disposed on the emission layer.

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

For example, the electron transport region may have a structure of an electron transport layer / electron injection layer or a hole blocking layer / electron transport layer / electron injection layer sequentially stacked from the light emitting layer, but is not limited thereto.

The electron transport region may include a hole blocking layer. The hole blocking layer may be formed to prevent a triplet exciton or hole from diffusing into the electron transport layer when the light emitting layer uses a phosphorescent dopant.

When the electron transport region includes a hole blocking layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI) The hole blocking layer may be formed on the emission layer by using various methods such as the above. When the hole blocking layer is formed by vacuum deposition or spin coating, deposition and coating conditions for the hole blocking layer may be similar to the deposition and coating conditions for the hole injection layer.

The hole blocking layer may include, for example, at least one of BCP and Bphen, but is not limited thereto.

The hole blocking layer may have a thickness of about 20 kPa to about 1000 kPa, for example, about 30 kPa to about 300 kPa. When the thickness of the hole blocking layer satisfies the aforementioned range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport region may include an electron transport layer. The electron transport layer, using a vacuum deposition method, spin coating method, cast method, LB (Langmuir-Blodgett), inkjet printing method, laser printing method, Laser Induced Thermal Imaging (LITI) and the like, The light emitting layer may be formed on or above the hole blocking layer. When the electron transport layer is formed by vacuum deposition and spin coating, deposition and coating conditions for the electron transport layer may be similar to the deposition and coating conditions for the hole injection layer.

The electron transport layer may include one or more selected from electron transport materials represented by Formula 1 below:

<Formula 1>

In Formula 1,

X ₁₁ , X ₁₂ and X ₁₃ are, independently from each other, CH or N;

At least one of X ₁₁ , X ₁₂ and X ₁₃ is N;

L ₁₁ and L ₁₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group, substituted or unsubstituted Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and Substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group );

n11, n12 and n21 to n23 are each independently selected from an integer of 0 to 3;

the sum of n11 and n12 is at least 1;

R ₁₁ to R ₁₃ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -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, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from the condensed polycyclic group;

a13 is an integer of 1 to 3;

The substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloalkenylene group, substitution C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C ₃ -C ₁₀ Cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C _6- C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₂ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic heterocondensation At least _{one of the} substituents of the polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group and substituted C ₁ -C ₆₀ alkoxy group,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) And C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocyclo substituted with at least one of —B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Teroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed polycyclic groups; And

-N (Q ₃₁ ) (Q ₃₂ ), -Si (Q ₃₄ ) (Q ₃₅ ) (Q ₃₆ ) and -B (Q ₃₇ ) (Q ₃₈ ); Is selected from;

Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ , Q ₃₁ , Q ₃₂ and Q ₃₃ to Q ₃₇ are each independently hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed polycyclic groups.

For example, in Formula 1, X ₁₁ and X ₁₃ may be N, and X ₁₂ may be CH, but is not limited thereto.

As another example, in Formula 1, X ₁₂ and X ₁₃ may be N, and X ₁₁ may be CH, but is not limited thereto.

As another example, in Formula 1, X ₁₂ may be N, and X ₁₁ and X ₁₃ may be CH, but are not limited thereto.

For example, in Formula 1, L ₁₁ and L ₁₂ are independently of each other,

Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene ( acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, phenylene picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene ovalenylene, pyrrolylene, thienylen e), furanylene, silolylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene , Isoxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, Indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene , Quinoxalinylene, quinazolinylene, quinazolinylene, carnozylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene , Phenazinylene, ben Imidazolylene, benzofuranylene, benzothienylene, benzosilolylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene (isobenzooxazolylene), triazolylene, tetrazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, Benzocarbazolyene, dibenzocarbazolyene and dibenzosilolylene; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, Heptalenyl, indasenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, naphthacenyl, fisenyl, peryllenyl, pentaphenyl, hexasenyl, pentansenyl, rubisenyl, coronyl, ovalenyl, pyrroyl, thienyl, furanyl, silolyl, imida Zolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, py Lidazinyl, isoindoleyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, sinolinyl, Carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, tria Phenylene, pentalenylene, indenylene, substituted with at least one of zolyl, tetrazole, oxdiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl and dibenzosilolyl , Naphthylene, azulenylene, heptalenylene, indasenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenenylene, phenanthrenylene, Anthracenylene, fluoranthhenylene, triphenylenylene, pyrenylene, Chrysenylene, naphthasenylene, fisenylene, peryleneylene, pentaphenylene, hexasenylene, pentansenylene, rubisenylene, coronylene, ovalenylene, pyrroylene, thienylene, furanylene, silol Irene, imidazole ylene, pyrazol ylene, thiazol ylene, isothiazo ylene, oxazol ylene, isoxazol ylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindoleylene, indole ylene , Indazole ylene, furinylene, quinolinilene, isoquinolinyl, benzoquinolinyl, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cynolinylene, carbazoylene, phenantridi Nylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothienylene, benzosilolylene, isobenzothiazoleylene, benzoxazolylene, isobenzooxazolylene, triazole Ylene, tetrazoleylene, oxadiazole ylene, triazinylene, di Division furanoid alkenylene, dibenzo-thio-phenylene, benzo-carbazol-ylene, dibenzo-carbazol-ylene and dibenzo silole ylene; It may be selected from, but is not limited thereto.

As another example, in Formula 1, L ₁₁ is

Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, penalenylene, phenanthrenylene, anthracenylene, fluoranthhenylene, triphenylenylene, Pyrenylene and chrysenylene; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthra At least one substituted with at least one selected from senyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl , Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, penalenylene, phenanthrenylene, anthracenylene, fluoranthhenylene, triphenylenylene , Pyrenylene and chrysenylene; It may be selected from, but is not limited thereto.

As another example, in Formula 1, L ₁₁ may be selected from Formulas 4-1 to 4-3, but is not limited thereto.

In Formulas 4-1 to 4-3,

Z ₁ and Z ₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl , Dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl , Carbazolyl and triazinyl,

d1 is selected from an integer of 1 to 8;

d2 is selected from an integer of 1 to 4;

* And ** are binding sites with neighboring atoms.

As another example, L ₁₂ is phenylene, naphthylene, anthracenylene and triphenylenylene; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthra At least one substituted with at least one selected from senyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl , Phenylene, naphthylene, anthracenylene and triphenylenylene; It may be selected from, but is not limited thereto.

As another example, in Formula 1, L ₁₂ may be selected from Formula 5-1, but is not limited thereto:

In Formula 5-1,

Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, Among phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Selected;

d1 is selected from an integer of 1 to 4;

* And ** are binding sites with neighboring atoms.

For example, in Formula 1, n11 and n12 are each independently an integer of 0 or 1; The sum of n11 and n12 may be 1 or more, but is not limited thereto.

As another example, in Formula 1, n11 and n12 may be integers of 1, but are not limited thereto.

For example, in Formula 1, R ₁₁ to R ₁₃ are independently of each other,

Phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, Carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; And

Deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, phenanthrenyl, fluorenyl, spiro- Fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl , Phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluore substituted with at least one substituent selected from quinoxalinyl, quinazolinyl, carbazolyl, triazinyl and -N (Q ₃₁ ) (Q ₃₂ ) Nil, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; Is selected from;

Q ₃₁ and Q ₃₂ may be each independently selected from a phenyl group and a naphthyl group, but are not limited thereto.

As another example, in Formula 1, R ₁₁ to R ₁₃ may be selected independently from each other, and the following Formula 7-1 to 7-18, but is not limited thereto:

In Formulas 7-1 to 7-18,

* Is a bonding site with a neighboring atom.

For example, in Formula 1, a13 may be an integer of 1, but is not limited thereto.

In an embodiment, the electron transporting material represented by Chemical Formula 1 may be represented by Chemical Formula 1A, but is not limited thereto.

<Formula 1A>

In Formula 1A,

X ₁₁ to X ₁₃ , L ₁₁ , n 11, R ₁₁ to R _13, and a13 are as described above.

In another embodiment, the electron transport material represented by Formula 1 may be selected from Compounds 1 to 267, but is not limited thereto.

The electron transporting material represented by Chemical Formula 1 may provide an organic light emitting device having excellent efficiency because of its excellent electron transporting ability.

The electron transport material represented by Chemical Formula 1 may provide an organic light emitting device having excellent heat resistance and excellent heat resistance.

Since the electron transport material represented by Formula 1 has a small change in electron transport ability due to temperature, it is possible to provide an organic light emitting device having a small change in device characteristics with temperature.

The electron transport layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 150 kPa to about 500 kPa. When the thickness of the electron transporting layer satisfies the aforementioned range, a satisfactory electron transporting characteristic can be obtained without a substantial increase in driving voltage.

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

The metal-containing material may comprise 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 be formed using various methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It may be formed on the electron transport layer. When the electron injection layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron injection layer refer to the deposition conditions and the coating conditions of the hole injection layer.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O, BaO, and LiQ.

The electron injection layer may have a thickness of about 1 kPa to about 100 kPa and about 3 kPa to about 90 kPa. When the thickness of the electron injection layer satisfies the aforementioned range, a satisfactory electron injection characteristic may be obtained without a substantial increase in driving voltage.

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, wherein the material for the second electrode 190 is a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof. Can be used. Specific examples of the material for the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In). , Magnesium-silver (Mg-Ag) and the like. Alternatively, ITO or IZO may be used as the material for the second electrode 190. The second electrode 190 may be a reflective electrode, a transflective electrode, or a transmissive electrode.

In general, an organic light emitting device including a material having a high electron transporting property tends to have a high efficiency but a reduced lifetime.

The organic light emitting device including the electron transporting material represented by Chemical Formula 1 and the hole transporting material represented by Chemical Formula 2 or 3 has a high electron transporting ability of the electron transporting material represented by Chemical Formula 1, and thus the efficiency of the organic light emitting device Properties can be improved.

The organic light emitting device including the electron transporting material represented by Chemical Formula 1 and the hole transporting material represented by Chemical Formula 2 or 3 may include the electron transporting material represented by Chemical Formula 1 and the hole transporting material represented by Chemical Formula 2 or 3 By including together, it is possible to improve the carrier balance of electrons and holes, so that the life characteristics of the organic light emitting device can be improved.

The organic light emitting device has been described above with reference to FIG. 1, but is not limited thereto.

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

In the present specification, a C ₁ -C ₆₀ alkoxy group refers to a monovalent group having a chemical formula of —OA ₁₀₁ (wherein A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, Isopropyloxy group etc. are contained.

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure including at least one carbon double bond in the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, propenyl group, butenyl group, and the like. do. As used herein, a C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, the C ₂ -C ₆₀ alkynyl group has a structure including at least one carbon triple bond in the middle or the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group and a propynyl group. , And the like. As used herein, a 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, a 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 a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclohep And a tilt group. As used herein, a 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, a C ₂ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P, and S as a ring-forming atom, and a sphere thereof Examples include tetrahydrofuranyl group, tetrahydrothiophenyl group and the like. As used herein, a C ₂ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkyl group.

As used herein, a C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in a ring, but having no aromacity. Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. As used herein, a 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, a C ₂ -C ₁₀ heterocycloalkenyl group is a C _{2 to} C ₁₀ monovalent monocyclic group including at least one hetero atom selected from N, O, P, and S as a ring-forming atom, and at least in a ring It has one double bond. Specific examples of the C ₂ -C ₁₀ heterocycloalkenyl group include 2,3-hydrofuranyl group, 2,3-hydrothiophenyl group, and the like. As used herein, a C ₂ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkenyl group.

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

As used herein, a C ₂ -C ₆₀ heteroaryl group means a monovalent group containing at least one hetero atom selected from N, O, P, and S as a ring-forming atom and having a carbocyclic aromatic system having 2 to 60 carbon atoms. And a C ₂ -C ₆₀ heteroarylene group means a divalent group containing at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 2 to 60 carbon atoms do. Specific examples of the C ₂ -C ₆₀ heteroaryl group include a pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group and the like. When the C ₂ -C ₆₀ heteroaryl group and the C ₂ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused to each other.

In the specification C ₆ -C ₆₀ aryloxy group -OA, point ₁₀₂ (where, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio group (arylthio) is -SA ₁₀₃ (where , A ₁₀₃ represents the C ₆ -C ₆₀ aryl group.

As used herein, a monovalent non-aromatic condensed polycyclic group includes two or more rings condensed with each other and includes only carbon as a ring forming atom (for example, carbon number may be 8 to 60). And a monovalent group in which the whole molecule has non-aromacity. Specific examples of the non-aromatic condensed polycyclic group include fluorenyl groups and the like. As used herein, the 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 includes two or more rings condensed with each other, and in addition to carbon (for example, carbon number may be 2 to 60) as a ring forming atom. It means a monovalent group containing a hetero atom selected from N, O, P and S, and the whole molecule has a non-aromacity. The monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group and the like. As used herein, the divalent non-aromatic heterocondensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, the substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloalkenyl Ethylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, Substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₂ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non- _{One of the} substituents of the aromatic heterocondensed polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group and substituted C ₁ -C ₆₀ alkoxy group At least one,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indaseyl group, an acenaph Tyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, Crysenyl group, naphthacenyl group, pisenyl group, peryleneyl group, pentaphenyl group, hexasenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, pyrroylyl group, thiophenyl group, furanyl group, imidazole Diary, pyrazolyl, thiazolyl, isothiazolyl, oxa Solyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolin Nyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzo Furanyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group , Benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) and -B (Q ₁₆ ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of (Q ₁₇ );

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cycloheptenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indaseyl group, acenaphthyl group, fluorene Nilyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pentansenyl group, rubisenyl group, coronyl group, ovarenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazole Diary, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazoleyl group, furinyl group, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, Lazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Solyl group, dibenzocarbazolyl group and imidazopyridinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, -N (Q ₂₁ ) (Q ₂₂ ) , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohepte substituted with at least one of -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) and -B (Q ₂₆ ) (Q ₂₇ ) Nilyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorene Nilyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl , Hexasenyl group, pentaxenyl group, rubisenyl group, coronyl group, opalenyl group, pyrroylyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group , Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, Phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group , Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzo Carbazolyl, dibenzocarbazolyl and imidazopi D group; And

-N (Q ₃₁ ) (Q ₃₂ ), -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) and -B (Q ₃₆ ) (Q ₃₇ ); Is selected from;

Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ , Q ₃₁ , Q ₃₂ and Q ₃₃ to Q ₃₇ are each independently hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cycloheptenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, argon Julenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluorine Lantenyl group, Triphenylenyl group, Pyrenyl group, Crysenyl group, Naphthacenyl group, Pisenyl group, Perylenyl group, Pentaphenyl group, Hexenyl group, Pentansenyl group, Rubysenyl group, Coronenyl group, Ovalle Nyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxa Diary, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl Group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothio Phenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group , Dibenzocarbazolyl group and imidazopyridinyl group.

In the present specification, "Ph" means phenyl, "Me" means methyl, "Et" means ethyl, and "ter-Bu" or "But" means tert-butyl.

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

EXAMPLE

Synthesis Example 1 Synthesis of Compound 20

9-bromo-10-phenylanthracene (3.5 g (1eq, 10.5 mmol)) and (3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) Pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid) 4.75 g (1.05eq) , 11.07 mmol), and tetrakis (triphenylphosphine) palladium (0) (485 mg (0.04eq, 0.42 mmol)) were added to a reaction vessel and vacuum dried, followed by nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.34 g of compound 20 (yield = 65%) was obtained through column chromatography.

1H-NMR: 9.26 (1H), 8.73 (1H), 8.43 (1H), 8.23 (2H), 7.91 (4H), 7.79 (5H), 7.57 (3H), 7.51 (8H), 7.41 (2H), 7.39 (4H). APCI-MS (m / z): 637.25 [M +]

Synthesis Example 2 Synthesis of Compound 23

6-bromo-12-phenylchrysene 4.0g (1eq, 10.5mmol) and (3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) Pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid) 4.75 g (1.05eq) , 11.07 mmol), and tetrakis (triphenylphosphine) palladium (0) (485 mg (0.04eq, 0.42 mmol)) were added to a reaction vessel and vacuum dried, followed by nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.00 g of compound 23 (yield = 70%) were obtained through column chromatography.

1H-NMR: 9.26 (1H), 9.15 (1H), 8.93 (2H), 8.70 (1H), 8.42 (1H), 8.24 (2H), 8.12 (2H), 7.88 ~ 7.70 (12H), APCI-MS ( m / z): 687.27 [M +]

Synthesis Example 3 Synthesis of Compound 26

3.7 g (1eq, 10.5 mmol) of 5-bromo-1-phenylpyrene and (3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) Pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid) 4.75 g (1.05eq) , 11.07 mmol), and tetrakis (triphenylphosphine) palladium (0) (485 mg (0.04eq, 0.42 mmol)) were added to a reaction vessel and vacuum dried, followed by nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.37 g of compound 26 (yield = 63%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.42 (1H), 8.24 (2H), 8.12 (1H), 8.04 (1H), 7.88 ~ 7.51 (13H), 7.57 ~ 7.41 (11H), APCI- MS (m / z): 661.25 [M +]

Synthesis Example 4 Synthesis of Compound 47

9-bromo-10- (naphthalen-1-yl) anthracene (9-bromo-10- (naphthalen-1-yl) anthracene) 4.0 g (1 eq, 10.5 mmol) and (3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2- yl) phenyl) boronic acid) 4.75g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (485mg (0.04eq, 0.42mmol) And vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.26 g of compound 47 (yield = 73%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.51 (1H), 8.42 (2H), 8.23 (2H), 8.04 (2H), 8.24 (4H) 7.91 (4H) 7.79-7.70 (5H), 7.61 ~ 7.41 (15H), APCI-MS (m / z): 687.27 [M +]

Synthesis Example 5 Synthesis of Compound 50

6-bromo-12- (naphthalen-1-yl) chrysene (6-bromo-12- (naphthalen-1-yl) chrysene) 4.5 g (1 eq, 10.5 mmol) and (3- (4-phenyl-6) -(3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2 -yl) phenyl) boronic acid) 4.75g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) 485mg (0.04eq, 0.42mmol) Placed in a vessel and dried under vacuum and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.03 g of compound 50 (yield = 65%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 9.15 (1H), 8.92 (2H), 8.70 (1H), 8.27 (1H), 8.42 (2H), 8.24 (2H) 8.12 (4H) 7.93-7.79 (10H), 7.61 ~ 7.41 (11H), APCI-MS (m / z): 737.28 [M +]

Synthesis Example 6 Synthesis of Compound 74

9-bromo-10- (naphthalen-2-yl) anthracene (9-bromo-10- (naphthalen-2-yl) anthracene) 4.0 g (1eq, 10.5 mmol) and (3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2- yl) phenyl) boronic acid) 4.75g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (485mg (0.04eq, 0.42mmol) And vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.12 g of compound 65 (yield = 71%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.51 (1H), 8.24 (2H), 8.04-7.79 (7H), 7.79-7.70 (6H), 7.61-7.41 (15H), APCI-MS (m / z): 687.27 [M +]

Synthesis Example 7 Synthesis of Compound 77

6-bromo-12- (naphthalen-2-yl) chrysene (6-bromo-12- (naphthalen-2-yl) chrysene) 4.53 g (1eq, 10.5 mmol) and (3- (4-phenyl-6) -(3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2 -yl) phenyl) boronic acid) 4.75g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) 485mg (0.04eq, 0.42mmol) Placed in a vessel and dried under vacuum and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.42 g of compound 77 (yield = 70%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.42 (1H), 8.24 (2H), 8.12 (1H), 8.04 (1H), 7.88 ~ 7.51 (13H), 7.57 ~ 7.41 (11H), APCI- MS (m / z): 661.25 [M +]

Synthesis Example 8 Synthesis of Compound 101

9-bromo-10- (phenanthren-9-yl) anthracene (9-bromo-10- (phenanthren-9-yl) anthracene) 4.56 g (1eq, 10.5 mmol) and (3- (4-phenyl-6 -(3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4-phenyl-6- (3- (pyridin-3-yl) phenyl) pyrimidin-2 -yl) phenyl) boronic acid) 4.75g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) 485mg (0.04eq, 0.42mmol) Placed in a vessel and dried under vacuum and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.42 g of compound 101 (yield = 70%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.93 (2H), 8.70 (1H), 8.42 (1H), 8.23 (2H), 8.12 (2H), 7.88-7.70 (14H), 7.59-7.41 (12H), APCI- MS (m / z): 737.28 [M +]

Synthesis Example 9 Synthesis of Compound 122

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (4- (pyridin-3-yl) -6- (3- (pyridine-3) -Yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4- (pyridin-3-yl) -6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl ) phenyl) boronic acid) 4.76g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (485mg (0.04eq, 0.42mmol) Put in, vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 5.42 g of compound 122 (yield = 70%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.42 (1H), 8.24 (2H), 8.12 (1H), 8.04 (1H), 7.88 ~ 7.51 (13H), 7.57 ~ 7.41 (11H), APCI- MS (m / z): 661.25 [M +]

Synthesis Example 10 Synthesis of Compound 140

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (4- (isoquinolin-4-yl) -6- (3- (pyridine- 3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4- (isoquinolin-4-yl) -6- (3- (pyridin-3-yl) phenyl) pyrimidin-2- yl) phenyl) boronic acid) 5.31g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) palladium (0)) 485mg (0.04eq, 0.42mmol) And vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.48 g of compound 140 (yield = 62%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.93 (1H), 8.70 (1H), 8.42 (2H), 8.23 (2H), 7.92 (5H), 7.75 (4H), 7.57-7.39 (16H), APCI-MS ( m / z): 688.26 [M +]

Synthesis Example 11 Synthesis of Compound 149

3.73 g (1 eq, 10.5 mmol) of 5-bromo-1-phenylpyrene and (3- (4- (isoquinolin-1-yl) -6- (3- (pyridine -3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4- (isoquinolin-1-yl) -6- (3- (pyridin-3-yl) phenyl) pyrimidin-2 -yl) phenyl) boronic acid) 5.31g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) 485mg (0.04eq, 0.42mmol) Placed in a vessel and dried under vacuum and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.37 g of compound 149 (yield = 63%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.42 (1H), 8.24 (2H), 8.12 (1H), 8.04 (1H), 7.88 ~ 7.51 (13H), 7.57 ~ 7.41 (11H), APCI- MS (m / z): 661.25 [M +]

Synthesis Example 12 Synthesis of Compound 158

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (4- (3- (pyridin-3-yl) phenyl) -6- (quinoline) -3-yl) pyrimidin-2-yl) phenyl) boronic acid ((3- (4- (3- (pyridin-3-yl) phenyl) -6- (quinolin-3-yl) pyrimidin-2-yl 5.31 g (1.05 eq, 11.07 mmol), tetrakis (triphenylphosphine) palladium (0)) 485 mg (0.04 eq, 0.42 mmol) was added to the reaction vessel. Put in, vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.56 g of compound 158 (yield = 65%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.93 (1H), 8.57 (1H), 8.42 (1H), 8.23 (3H), 8.06 (1H) 7.98 (5H), 7.78 (4H), 7.60-7.39 (15H), APCI-MS (m / z): 668.26 [M +]

Synthesis Example 13 Synthesis of Compound 176

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (6-phenyl-2- (3- (pyridin-3-yl) phenyl) pyri) Midin-4-yl) phenyl) boronic acid ((3- (6-phenyl-2- (3- (pyridin-3-yl) phenyl) pyrimidin-4-yl) phenyl) boronic acid) 5.02 g (1.05eq, 11.07 mmol) and 485 mg (0.04 eq, 0.42 mmol) of tetrakis (triphenylphosphine) palladium (0) were placed in a reaction vessel and dried under vacuum and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.35 g of compound 176 (yield = 65%) was obtained by column chromatography.

1H-NMR: 9.26 (1H), 8.70 (1H), 8.42 (1H), 8.24 (2H), 8.12 (1H), 8.04 (1H), 7.88 ~ 7.51 (13H), 7.57 ~ 7.41 (11H), APCI- MS (m / z): 661.25 [M +]

Synthesis Example 14 Synthesis of Compound 185

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (6- (pyridin-2-yl) -2- (3- (pyridine-3) -Yl) phenyl) pyrimidin-4-yl) phenyl) boronic acid ((3- (6- (pyridin-2-yl) -2- (3- (pyridin-3-yl) phenyl) pyrimidin-4-yl ) phenyl) boronic acid) 4.76 (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) 485mg (0.04eq, 0.42mmol) was added to the reaction vessel. Vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.15 g of compound 185 (yield = 62%) was obtained by column chromatography.

1 H-NMR: 9.26 (2H), 8.70 (2H), 8.42 (2H), 8.23 (2H), 7.78 (4H), 7.75 (3H), 7.51-7.41 (15H), APCI-MS (m / z): 638.76 [M +]

Synthesis Example 15 Synthesis of Compound 194

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (6- (isoquinolin-3-yl) -2- (3- (pyridine- 3-yl) phenyl) pyrimidin-4-yl) phenyl) boronic acid ((3- (6- (isoquinolin-3-yl) -2- (3- (pyridin-3-yl) phenyl) pyrimidin-4- yl) phenyl) boronic acid) 5.31g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) palladium (0)) 485mg (0.04eq, 0.42mmol) And vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.70 g of compound 194 (yield = 65%) was obtained through column chromatography.

1H-NMR: 9.26 (2H), 8.87 (1H), 8.70 (1H), 8.42 (2H), 8.23 (2H), 7.92 (5H), 7.75 (4H), 7.51-7.41 (16H), APCI-MS ( m / z): 688.26 [M +]

Synthesis Example 16 Synthesis of Compound 221

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (4- (pyridin-2-yl) -6- (3- (pyridine-3) -Yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid (3- (4- (pyridin-2-yl) -6- (3- (pyridin-3-yl) phenyl) pyrimidin-2-yl) phenyl) boronic acid) 4.76g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (485mg (0.04eq, 0.42mmol) Vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.15 g of compound 221 (yield = 62%) was obtained by column chromatography.

1 H-NMR: 9.26 (2H), 8.70 (2H), 8.59 (1H), 8.23 (2H), 7.92 (4H), 7.75 (4H), 7.51-7.41 (15H), APCI-MS (m / z): 638.25 [M +]

Synthesis Example 17 Synthesis of Compound 228

3.48 g (1 eq, 10.5 mmol) of 9-bromo-10-phenylanthracene and (3- (2- (isoquinolin-4-yl) -6- (4- (pyridine- 2-yl) phenyl) pyrimidin-4-yl) phenyl) boronic acid ((3- (2- (isoquinolin-4-yl) -6- (4- (pyridin-2-yl) phenyl) pyrimidin-4- yl) phenyl) boronic acid) 5.31g (1.05eq, 11.07mmol), tetrakis (triphenylphosphine) palladium (0) (485mg (0.04eq, 0.42mmol) And vacuum dried and filled with nitrogen gas. 80 ml of toluene, 40 ml of ethanol, and 16 ml (3eq, 31.6 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction vessel, followed by stirring under reflux at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layers were combined, and then the combined organic layers were dried over magnesium sulfate. The crude product was obtained by distillation under reduced pressure, and then 4.84 g of compound 228 (yield = 67%) was obtained by column chromatography.

1H-NMR: 8.87 (3H), 8.59 (1H), 8.50 (2H), 8.33 (2H), 7.92 (5H), 7.75 (3H), 7.51-7.41 (14H), 7.26 (1H), 7.01 (1H) APCI-MS (m / z): 688.26 [M +]

Example 1

Cut a 1200 유리 thick ITO glass substrate (from Corning) into 50mm x 50mm x 0.7mm and ultrasonically clean it for 5 minutes with isopropyl alcohol and pure water, and then irradiate with ultraviolet rays for 30 minutes It was exposed and cleaned and the ITO / Ag / ITO glass substrate was installed in a vacuum deposition apparatus.

After depositing m-MTDATA on the anode to form a hole injection layer having a thickness of 600 ,, Compound 309 is deposited on the hole injection layer to form a hole transport layer having a thickness of 300Å, and then ADN and FD9 on the hole transport layer. Was co-deposited at a weight ratio of 95: 5 to form a light emitting layer having a thickness of 200 kHz.

Compound 20 was deposited on the emission layer to form an electron transport layer of 300 kHz. An organic light emitting device was manufactured by depositing LiF on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then vacuum depositing Al on the electron injection layer to form a cathode having a thickness of 1000,.

Example 2

An organic EL device was prepared in the same manner as in Example 1, except that Compound 23 was used instead of Compound 20 as the electron transporting layer.

Example 3

An organic EL device was produced in the same manner as in Example 1, except that Compound 26 was used instead of Compound 20 as the electron transporting layer.

Example 4

An organic EL device was prepared in the same manner as in Example 1, except that Compound 47 was used instead of Compound 20 as the electron transporting layer.

Example 5

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 50 was used instead of Compound 20 as the electron transporting layer.

Example 6

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 74 was used instead of Compound 20 as the electron transporting layer.

Example 7

An organic EL device was produced in the same manner as in Example 1, except that Compound 77 was used instead of Compound 20 as the electron transporting layer.

Example 8

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 101 was used instead of Compound 20 as the electron transporting layer.

Example 9

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 122 was used instead of Compound 20 as the electron transporting layer.

Example 10

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 140 was used instead of Compound 20 as the electron transporting layer.

Example 11

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 149 was used instead of Compound 20 as the electron transporting layer.

Example 12

An organic EL device was produced in the same manner as in Example 1, except that Compound 158 was used instead of Compound 20 as the electron transporting layer.

Example 13

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 176 was used instead of Compound 20 as the electron transporting layer.

Example 14

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 185 was used instead of Compound 20 as the electron transporting layer.

Example 15

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 194 was used instead of Compound 20 as the electron transporting layer.

Example 16

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 221 was used instead of Compound 20 as the electron transporting layer.

Example 17

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 228 was used instead of Compound 20 as the electron transporting layer.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 20 as an electron transporter.

<Compound A>

Comparative Example 2

An organic EL device was prepared in the same manner as in Example 1, except that Compound B was used instead of Compound 309 as the hole transport layer.

<Compound B>

Comparative Example 3

An organic EL device was fabricated in the same manner as in Example 1, except that Compound A was used instead of Compound 20 as the electron transporting layer and Compound B was used instead of Compound 309 as the hole transporting layer.

Evaluation example 1

The driving voltage, brightness and efficiency of the organic light emitting diodes manufactured in Examples 1 to 17 and Comparative Examples 1 to 3 were measured using a Kethley SMU 236 and a luminance meter PR650.

Hole transport layer
Electron transport layer
Driving voltage
(V) Luminance
(cd / m ² ) efficiency
(cd / A) Example 1 Compound 309 Compound 20 3.7 350 3.50 Example 2 Compound 309 Compound 23 3.8 412 4.12 Example 3 Compound 309 Compound 26 3.7 385 3.85 Example 4 Compound 309 Compound 47 4.0 373 3.73 Example 5 Compound 309 Compound 50 3.9 325 3.25 Example 6 Compound 309 Compound 74 3.8 407 4.07 Example 7 Compound 309 Compound 77 3.7 362 3.62 Example 8 Compound 309 Compound 101 4.1 340 3.40 Example 9 Compound 309 Compound 122 4.0 312 3.12 Example 10 Compound 309 Compound 140 3.8 290 2.90 Example 11 Compound 309 Compound 149 3.7 360 3.60 Example 12 Compound 309 Compound 158 3.9 378 3.78 Example 13 Compound 309 Compound 176 4.2 408 4.08 Example 14 Compound 309 Compound 185 3.7 355 3.55 Example 15 Compound 309 Compound 194 4.1 342 3.42 Example 16 Compound 309 Compound 221 4.3 331 3.31 Example 17 Compound 309 Compound 228 4.1 389 3.89 Comparative Example 1 Compound 309 Compound A 4.5 255 2.55 Comparative Example 2 Compound B Compound 20 4.4 247 2.47 Comparative Example 3 Compound B Compound A 4.6 220 2.20

It can be seen from Table 1 that the driving voltage, brightness and efficiency of the organic light emitting diodes of Examples 1 to 17 are superior to the driving voltage, brightness and efficiency of the organic light emitting diodes of Comparative Examples 1 to 3.

As described above, the present invention has been described with reference to one embodiment shown in the drawings, which is merely exemplary, and it will be understood by those skilled in the art that various modifications and variations of the embodiment are possible therefrom. Therefore, the true technical protection scope of the present invention will be defined by the technical spirit of the appended claims.

10: organic light emitting device
110: first electrode
150: organic layer
190: second electrode

Claims (18)

A first electrode;
A second electrode opposed to the first electrode;
A light emitting layer interposed between the first electrode and the second electrode;
An electron transport region interposed between the light emitting layer and the second electrode;
A hole transport region interposed between the first electrode and the light emitting layer;
The electron transport region includes at least one selected from an electron transport material represented by Formula 1 below;
The hole transport region is an organic light emitting device comprising at least one selected from a hole transport material represented by the formula (2):
<Formula 1>

<Formula 2>

In Formulas 1 and 2,
X ₁₁ , X ₁₂ and X ₁₃ are, independently from each other, CH or N;
At least one of X ₁₁ , X ₁₂ and X ₁₃ is N;
L ₁₁ is phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, penalenylene, phenanthrenylene, fluoranthhenylene, triphenylenylene, pi Lenylene and chrysenylene; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthra At least one substituted with at least one selected from senyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl , Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, penalenylene, phenanthrenylene, fluoranthhenylene, triphenylenylene, pyrenylene And chrysenylene; Is selected from;
L ₁₂ is phenylene, naphthylene and triphenylenylene; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthra At least one substituted with at least one selected from senyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl , Phenylene, naphthylene and triphenylenylene; Is selected from;
n11 and n12 are integers of 1;
L ₂₁ to L ₂₃ are independently of each other,
Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysenylene, pyridinylene, pyrazinyl Ylenes, pyrimidinylene, pyridazinylene, quinolinilene, isoquinolinylene, quinoxalinylene, quinazolinylene, carbazolylene and triazinylene; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthra At least one substituted with at least one selected from senyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl , Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysenylene, pyridinylene, pyra Genylene, pyrimidinylene, pyridazinylene, quinolinylene, isoquinolinylene, quinone Salicylate alkenylene, quinazolinyl alkenylene, carbazol-ylene and triazinyl alkylene; Is selected from;
n21 to n23 are each independently selected from an integer of 0 to 3;
R ₁₁ to R ₁₃ and R ₂₁ are each independently of each other phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, Pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; And
Deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, Benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl Phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, anthracenyl substituted with at least one substituent selected from quinazolinyl, carbazolyl, triazinyl and -N (Q ₃₁ ) (Q ₃₂ ) , Pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; Is selected from;
Q ₃₁ and Q ₃₂ are each independently selected from a phenyl group and a naphthyl group;
R ₂₂ to R ₂₄ are independently of each other,
C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;
Phenyl, naphthyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, tria Genyl, dibenzofuranyl and dibenzothienyl; And
Deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, Benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl , Phenyl, naphthyl, fluorenyl, benzofluorenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidyl substituted with at least one substituent selected from quinazolinyl, carbazolyl and triazinyl Nil, pyridazinyl, quinolinyl, isoquinolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothienyl; Is selected from;
a13 is an integer of 1 to 3;
R ₂₅ to R ₂₈ are each independently
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₆₀ alkyl group, and C ₁ -C ₆₀ alkoxy group; Is selected from;
a25 and a27 are each independently selected from an integer of 1 to 3;
a26 and a28 are each independently selected from integers of 1 to 4. The method of claim 1,
X ₁₁ and X ₁₃ are N and X ₁₂ is CH;
X ₁₂ and X ₁₃ are N and X ₁₁ is CH;
X ₁₂ is N, and X ₁₁ and X ₁₃ are CH. The method of claim 1,
L ₁₁ is an organic light emitting device selected from Chemical Formulas 4-1 and 4-2:

In Formulas 4-1 to 4-3,
Z ₁ and Z ₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl , Dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl , Carbazolyl and triazinyl,
d1 is selected from an integer of 1 to 8;
d2 is selected from an integer of 1 to 4;
* And ** are binding sites with neighboring atoms. The method of claim 1,
L ₁₂ is represented by the following Chemical Formula 5-1, an organic light emitting device:

In Formula 5-1,
Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, Among phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Selected;
d1 is selected from an integer of 1 to 4;
* And ** are binding sites with neighboring atoms. The method of claim 1,
L ₂₁ to L ₂₃ may be each independently selected from Chemical Formulas 6-1 to 6-7.

In Chemical Formulas 6-1 to 6-7,
Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, Among phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Selected,
d1 is selected from an integer of 1 to 4;
d3 is selected from an integer of 1 to 6;
d4 is selected from an integer of 1 to 8;
* And ** are binding sites with neighboring atoms. The method of claim 1,
n21 is 1 and n22 and n23 are 0. The method of claim 1,
R ₁₁ to R ₁₃ are each independently an organic light emitting device selected from Chemical Formulas 7-1 to 7-18:

In Formulas 7-1 to 7-18,
* Is a bonding site with a neighboring atom. The method of claim 1,
R ₂₁ is phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; And
Deuterium, halogen atom, cyano, nitro, methyl and at least one substituent selected from methoxy, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and -N (Ph) ₃ Substituted phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; The organic light emitting element is selected from. The method of claim 1,
R ₂₂ to R ₂₄ are independently of each other,
Methyl and methoxy;
Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; And
At least one selected from deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, methyl, methoxy, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl substituted with substituents of; The organic light emitting element is selected from. The method of claim 1,
a13 is 1, The organic light emitting element. The method of claim 1,
R ₂₅ to R ₂₈ are each independently
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, methyl and methoxy; An organic light emitting device is selected from. The method of claim 1,
At least one selected from the electron transport material represented by Formula 1 is an organic light emitting device represented by Formula 1A:
<Formula 1A>

In Formula 1A,
X ₁₁ to X ₁₃ , L ₁₁ , n 11, R ₁₁ to R ₁₃ and a13 are the same as defined in claim 1. The method of claim 1,
At least one selected from the hole transport material represented by Formula 2 is an organic light emitting device represented by Formula 2A:
<Formula 2A>

In Formula 2A,
R ₂₁ to R ₂₈ and a25 to a28 are as defined in claim 1. The method of claim 1,
At least one selected from the electron transporting materials represented by Formula 1 is the following compounds 4 to 9, 13 to 18, 22 to 27, 31 to 36, 40 to 45, 49 to 54, 58 to 63, 67 to 72, 76 1 to 81, 85 to 90, 94 to 99, 103 to 108, 112 to 117, 127 to 135, 145 to 153, 163 to 171 and 244 to 267, 1 selected from the hole transport material represented by the formula At least one species selected from compounds 309 to 322, 325, and 326:

The method of claim 1,
The hole transport region comprises a hole transport layer,
The hole transport layer is an organic light emitting device comprising at least one selected from a hole transport material represented by the formula (2). The method of claim 1,
The electron transport region comprises an electron transport layer,
The electron transport layer comprises an organic light emitting device comprising at least one selected from the electron transport material represented by the formula (1). A first electrode;
A second electrode opposed to the first electrode;
A light emitting layer interposed between the first electrode and the second electrode;
An electron transport region interposed between the light emitting layer and the second electrode;
A hole transport region interposed between the first electrode and the light emitting layer;
The electron transport region includes at least one selected from an electron transport material represented by Formula 1 below;
The hole transport region is an organic light emitting device comprising at least one selected from a hole transport material represented by the formula (2):
<Formula 1>

<Formula 2>

In Formulas 1 and 2,
X ₁₁ , X ₁₂ and X ₁₃ are, independently from each other, CH or N;
At least one of X ₁₁ , X ₁₂ and X ₁₃ is N;
L ₁₁ is selected from Formulas 4-1 and 4-2;

In Formulas 4-1 to 4-3,
Z ₁ and Z ₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl , Dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl , Carbazolyl and triazinyl,
d1 is selected from an integer of 1 to 8;
d2 is selected from an integer of 1 to 4;
* And ** are binding sites with neighboring atoms;
L ₁₂ is represented by the following Chemical Formula 5-1;

In Formula 5-1,
Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, Among phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Selected;
d1 is selected from an integer of 1 to 4;
* And ** are binding sites with neighboring atoms;
n11 and n12 are integers of 1;
L ₂₁ to L ₂₃ are each independently selected from the following Chemical Formulas 6-1 to 6-7;

In Chemical Formulas 6-1 to 6-7,
Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, Among phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl Selected,
d1 is selected from an integer of 1 to 4;
d3 is selected from an integer of 1 to 6;
d4 is selected from an integer of 1 to 8;
* And ** are binding sites with neighboring atoms;
n21 to n23 are each independently selected from an integer of 0 to 3;
R ₁₁ to R ₁₃ are each independently selected from the following Chemical Formulas 7-1 to 7-18;

In Formulas 7-1 to 7-18,
* Is a binding site with a neighboring atom;
R ₂₁ is phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; And
Deuterium, halogen atom, cyano, nitro, methyl and at least one substituent selected from methoxy, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and -N (Ph) ₃ Substituted phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; Is selected from;
R ₂₂ to R ₂₄ are independently of each other,
Methyl and methoxy;
Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; And
At least one selected from deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, methyl, methoxy, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl Phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl substituted with substituents of; Is selected from;
a13 is an integer of 1 to 3;
R ₂₅ to R ₂₈ are each independently
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, methyl and methoxy; Is selected from;
a25 and a27 are each independently selected from an integer of 1 to 3;
a26 and a28 are each independently selected from integers of 1 to 4. delete

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