KR20220102317A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound and an organic light emitting device including the same. An exemplary embodiment of the present specification provides the compound represented by chemical formula 1. The compound according to an exemplary embodiment of the present specification can be used as a material of an organic material layer of the organic light emitting device, and by using the same, and it is possible to improve efficiency, lower driving voltage, and/or improve lifespan characteristics of the organic light emitting device.

Description

Compound and organic light emitting device including the same

The present specification relates to a compound and an organic light emitting device including the same.

The organic light emitting diode has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

As materials used in organic light emitting devices, pure organic materials or complex compounds in which organic materials and metals are complexed account for most, and depending on the use, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed A material with high luminous efficiency that converts it into light when it is formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

Korean Patent Publication No. 2016-132822

The present specification provides a compound and an organic light emitting device comprising the same.

An exemplary embodiment of the present specification provides a compound of Formula 1 below.

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,

b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,

r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.

In addition, an exemplary embodiment of the present specification includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device.

In particular, when the compound of the present invention is used in the hole injection layer, the hole transport layer or the electron blocking layer, the driving voltage of the device is lowered, the efficiency of the device is increased, and the lifespan is prolonged.

1 to 3 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in more detail.

The present specification provides a compound of Formula 1 below.

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,

b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,

r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.

The compound of Formula 1 is characterized in that when the carbon number of the naphthalene group is referred to as follows, carbon 1 is an amine group and carbon 2 is a carbazole group.

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

Hereinafter, the substituents of the present specification will be described in detail below, but the present invention is not limited thereto.

As used herein, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and two or more When substituted, two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); amine group; alkoxy group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, such as 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrene group, triphenylene group, pyrene group, phenalenyl group, perylenyl group, chrysenyl group, fluorenyl group, fluoranthene group, etc. However, the present invention is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

and

etc. can be However, the present invention is not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, S and P, and the like. The number of carbon atoms is not particularly limited, but preferably has 1 to 50 carbon atoms, further preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group may be an aromatic ring, an aliphatic ring, and a ring condensed therewith. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, A phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the heteroaryl group is an aromatic ring group containing one or more atoms other than carbon and heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S. can Although carbon number is not specifically limited, It is preferable that carbon number is 2-60. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heteroaryl group may be selected from the examples of the heterocyclic group.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto it is not

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the alkyl group and the aryl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the aryl group described above.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 1 to 50 carbon atoms.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R1 and R2 are each hydrogen.

In an exemplary embodiment of the present specification, a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other.

In an exemplary embodiment of the present specification, R1 is hydrogen, and a is 4.

In the exemplary embodiment of the present specification, b is an integer of 1 to 4, and when b is 2 or more, two R2 are the same as or different from each other.

In the exemplary embodiment of the present specification, R2 is hydrogen, and b is 4.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; terphenylene group; or a naphthylene group.

In an exemplary embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In an exemplary embodiment of the present specification, L3 is a direct bond; phenylene group; or a biphenylene group.

In an exemplary embodiment of the present specification, L3 is a phenylene group; or a biphenylene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group, an aryl group, or a phenyl group unsubstituted or substituted with a heterocyclic group; a biphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a terphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a naphthyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a phenanthrene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a triphenylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a fluorenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a carbazole group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; a dibenzofuran group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; or a dibenzothiophene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; a biphenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; terphenyl group unsubstituted or substituted with an aryl group; a naphthyl group unsubstituted or substituted with an aryl group; a phenanthrene group unsubstituted or substituted with an aryl group; a triphenylene group unsubstituted or substituted with an aryl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; carbazole group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group, a carbazole group, or a dibenzofuran group; a biphenyl group unsubstituted or substituted with a naphthyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a carbazole group; phenanthrene group; triphenylene group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; carbazole group; dibenzofuran group; or a dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are each represented by any one of the following structures.

In the above structures, the dotted line indicates a bonding position, and R101 is a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1 above,

R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

c is an integer of 1 to 4, and when c is 2 or more, 2 or more R3 are the same as or different from each other,

d is an integer of 1 to 4, and when d is 2 or more, 2 or more R4 are the same as or different from each other,

e is an integer of 1 to 4, and when e is 2 or more, 2 or more R 5 are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1-1 is any one of the following Chemical Formulas 1-1-1 to 1-1-3.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

In Formulas 1-1-1 to 1-1-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1,

R3 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

c is an integer of 1 to 4, and when c is 2 or more, 2 or more R3 are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1-2 is any one of the following Chemical Formulas 1-2-1 to 1-2-3.

[Formula 1-2-1]

[Formula 1-2-2]

[Formula 1-2-3]

In Formulas 1-2-1 to 1-2-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1,

R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer of 1 to 4, and when d is 2 or more, R4 of 2 or more are the same as or different from each other,

e is an integer of 1 to 4, and when e is 2 or more, 2 or more R 5 are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1-3 is any one of the following Chemical Formulas 1-3-1 to 1-3-3.

[Formula 1-3-1]

[Formula 1-3-2]

[Formula 1-3-3]

In Formulas 1-3-1 to 1-3-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1,

R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer of 1 to 4, and when d is 2 or more, R4 of 2 or more are the same as or different from each other,

e is an integer of 1 to 4, and when e is 2 or more, 2 or more R 5 are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1-4 is any one of the following Chemical Formulas 1-4-1 to 1-4-3.

[Formula 1-4-1]

[Formula 1-4-2]

[Formula 1-4-3]

In Formulas 1-4-1 to 1-4-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1,

R4 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer of 1 to 4, and when d is 2 or more, R4 of 2 or more are the same as or different from each other,

e is an integer of 1 to 4, and when e is 2 or more, 2 or more R 5 are the same as or different from each other.

In an exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; or an aryl group.

In an exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; or a phenyl group.

In an exemplary embodiment of the present specification, the compound of Formula 1 is any one of the following compounds.

The compound of Formula 1 of the present specification may have a core structure as shown in the following reaction scheme. Substituents may be combined by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

<Scheme 1>

In the above scheme, R1, R2, L1 to L3, Ar1 to Ar3, a, b, r1 to r3 are as defined in Formula 1.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.

In addition, by introducing various substituents into the core structure of the structure as described above, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport layer material, an electron blocking layer material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.

In addition, the organic light emitting device according to the present specification includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound of Formula 1 described above.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate. It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that injects and transports holes at the same time, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons, etc. However, the present invention is not limited thereto and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

In the exemplary embodiment of the present specification, the organic material layer may have a single-layer structure, but may have a multi-layered structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present specification is an organic material layer, a hole injection layer, a hole transport layer, a layer that transports and injects holes at the same time, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and an electron transport and electron injection layer at the same time. It may have a structure including layers and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In an exemplary embodiment of the present specification, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer may include the compound.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present specification, the organic material layer may include an emission layer, and the emission layer may include the compound as a dopant of the emission layer.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, and may further include a host.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, further includes a fluorescent host or a phosphorescent host, and another organic compound, a metal or a metal compound as a dopant may further include

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes the compound as a dopant of the emission layer, further includes a fluorescent host or a phosphorescent host, and an iridium-based (Ir) dopant can also be used. have.

In the exemplary embodiment of the present specification, the organic material layer may include an emission layer, and the emission layer may include the compound as a host of the emission layer.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a host of the light emitting layer, and may further include a dopant.

In the exemplary embodiment of the present specification, the organic material layer may include an electron blocking layer, and the electron blocking layer may include the compound.

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

For example, the structure of the organic light emitting device of the present specification may have the structure shown in FIGS. 1 and 2 , but is not limited thereto.

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , a first electrode 2 , a light emitting layer 3 , and a second electrode 4 .

2 is an organic light emitting device including a substrate 1 , a first electrode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 7 , an electron transport layer 8 , and a second electrode 4 . shows an example of

3 is a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, a hole blocking layer 10, electron transport and An example of an organic light emitting device connected to the layer 11 and the second electrode 4 for injecting electrons at the same time is shown.

Specifically, the organic light emitting device may have, for example, the following stacked structure in addition to the structure specified in the drawings, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

(3) anode/hole transport layer/light emitting layer/electron transport layer/cathode

(4) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(5) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(7) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(8) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(9) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(10) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(11) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(12) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(13) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(14) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(15) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / layer that simultaneously transports and injects electrons / cathode

In the exemplary embodiment of the present specification, the 'electron transport layer/electron injection layer' may be replaced with an electron injection and transport layer.

In an exemplary embodiment of the present specification, the hole transport layer may have a multilayer structure. For example, it may be composed of a first hole transport layer and a second hole transport layer including different materials.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. For example, examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto. .

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. For example, as the anode material, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, LiF/Al or LiO ₂ /Al, such as multi-layered materials, and the like, but are not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode to the light emitting layer. The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. For example, as the hole injection material, metal porphyrine, oligothiophene, arylamine-based compound, hexanitrile hexaazatriphenylene-based compound, quinacridone-based compound, and perylene-based compound compound, benzonitrile-based compound, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but is not limited thereto. Specifically, for the hole injection layer, an arylamine-based compound and a benzonitrile-based compound may be used. More specifically, a benzonitrile-based compound substituted with a halogen group and an arylamine-based compound substituted with a carbazole group may be used, but the present invention is not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of transporting holes from the anode or hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. For example, the hole transport material includes, but is not limited to, an arylamine-based compound, a carbazole-based compound, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. Specifically, a carbazole-based compound substituted with an arylamine group may be used in the hole transport layer, but is not limited thereto.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-described compound or a material known in the art may be used for the electron blocking layer.

The light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, the light-emitting material includes an 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. For example, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Specifically, an anthracene derivative may be used as the host of the emission layer, but is not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light-emitting layer emits blue light, the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a pyrene-based compound, a PFO-based polymer, or a PPV-based polymer may be used, but is not limited thereto. Specifically, a pyrene-based compound may be used as the dopant, but is not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer. The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. For example, the material applied to the hole blocking layer includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a triazine derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like. Specifically, a triazine derivative may be used, but is not limited thereto.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. For example, the electron transport material includes an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, a hydroxyflavone-metal complex, and the like, but is not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and a thin film A compound excellent in forming ability is preferred. For example, as the electron injection material, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane , anthrone and the like, derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The electron transport layer and the electron injection layer may be formed as a single layer. For example, the electron injection and transport layer may be formed by vacuum deposition of the electron injection material and the electron transport material at the same time. The electron injection and transport layer may further include a metal complex. Examples of the metal complex include, but are not limited to, an Al complex of 8-hydroxyquinoline (Alq ₃ ), LiQ, and a metal complex compound. For example, a triazine derivative and lithium quinolite (LiQ) may be used for the electron injection and transport layer, but the present invention is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

Hereinafter, an experimental example will be described in detail to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those of ordinary skill in the art.

< production example >

production example One.

Compound 9-(1-(4-chlorophenyl)naphthalen-2-yl)-9H-carbazole(9-(1-(4-chlorophenyl)naphthalen-2-yl)- in a 500 mL round bottom flask under nitrogen atmosphere 9H-carbazole) (8.26 g, 20.45 mmol) and compound a1 (10.06 g, 22.49 mmol) were completely dissolved in 270 mL of xylene, and then sodium tert-butoxide (NaOtBu) (2.95 g, 30.67 mmol) was added, bis(tri- tert -butylphosphine)palladium(0)(Bis(tri- tert -butylphosphine)palladium(0))(0.21 g, 0.41 mmol) was added, and then heated and stirred for 4 hours. did. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 280 mL of ethyl acetate to prepare compound 1 (11.24 g, yield: 67%).

MS[M+H] ⁺ = 816

production example 2.

Compounds in 500 mL round bottom flasks under nitrogen atmosphere

9-(1-(4-chlorophenyl)naphthalen-2-yl)-9H-carbazole (9-(1-(4-chlorophenyl)naphthalen-2-yl)-9H-carbazole) (8.05 g, 19.93 mmol) ) and compound a2 (9.22 g, 21.92 mmol) were completely dissolved in 280 mL of xylene, NaOtBu (2.87 g, 29.89 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.20 g, 0.40 mmol) was added. ) and then heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare compound 2 (8.96 g, yield: 57%).

MS[M+H] ⁺ = 789

production example 3.

Compound 9-(1-(4-chlorophenyl)naphthalen-2-yl)-9H-carbazole(9-(1-(4-chlorophenyl)naphthalen-2-yl)- in a 500 mL round bottom flask under nitrogen atmosphere 9H-carbazole) (7.88 g, 19.50 mmol) and compound a3 (9.39 g, 21.46 mmol) were completely dissolved in 270 mL of xylene, NaOtBu (2.81 g, 29.26 mmol) was added, and Bis(tri- tert -butylphosphine) After adding palladium (0) (0.20 g, 0.39 mmol), the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 3 (11.34 g, yield: 57%).

MS[M+H] ⁺ = 806

production example 4.

Compound 9-(1-(4-chlorophenyl)naphthalen-2-yl)-9H-carbazole(9-(1-(4-chlorophenyl)naphthalen-2-yl)- in a 500 mL round bottom flask under nitrogen atmosphere 9H-carbazole) (8.37 g, 20.72 mmol) and compound a4 (9.97 g, 22.79 mmol) were completely dissolved in 260 mL of xylene, NaOtBu (2.99 g, 31.08 mmol) was added, and Bis(tri- tert -butylphosphine) After adding palladium (0) (0.21 g, 0.41 mmol), the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare compound 4 (9.76 g, yield: 58%).

MS[M+H] ⁺ = 779

production example 5.

Compound 9-(1-(4'-chloro-[1.1'-biphenyl]-4-yl)naphthalen-2-yl)-9H-carbazole (9-(1- (4'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-2-yl)-9H-carbazole) (7.55 g, 15.73 mmol) and compound a5 (5.97 g, 17.30 mmol) with xylene After it was completely dissolved in 270 mL, NaOtBu (2.27 g, 23.59 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.16 g, 0.31 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 280 mL to prepare compound 5 (7.39 g, yield: 60%).

MS[M+H] ⁺ = 789

production example 6.

Compounds in 500 mL round bottom flasks under nitrogen atmosphere

9-(1-(3'-chloro-[1,1'-biphenyl]-3-yl)naphthalen-2-yl)-9H-carbazole (9-(1-(3'-chloro-[1) ,1'-biphenyl]-3-yl)naphthalen-2-yl)-9H-carbazole) (7.88 g, 16.42 mmol) and compound a6 (6.72 g, 18.06 mmol) were completely dissolved in 290 mL of xylene, and then NaOtBu ( 2.37 g, 24.63 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.17 g, 0.33 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 6 (9.14 g, yield: 68%).

MS[M+H] ⁺ = 816

production example 7.

Compounds in 500 mL round bottom flasks under nitrogen atmosphere

9-(1-(2'-chloro-[1,1'-biphenyl]-2-yl)naphthalen-2-yl)-9H-carbazole (9-(1-(2'-chloro-[1) ,1'-biphenyl]-2-yl)naphthalen-2-yl)-9H-carbazole) (7.28 g, 15.17 mmol), and compound a7 (7.04 g, 16.68 mmol) were completely dissolved in 240 mL of Xylene and then NaOtBu ( 2.19 g, 22.75 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.16 g, 0.30 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure, and recrystallized from 310 mL of ethyl acetate to prepare compound 7 (8.82 g, yield: 67%).

MS[M+H] ⁺ = 866

production example 8.

Compounds in 500 mL round bottom flasks under nitrogen atmosphere

9-(1-(3'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-2-yl)-9H-carbazole (9-(1-(3'-chloro-[1) ,1'-biphenyl]-4-yl)naphthalen-2-yl)-9H-carbazole) (7.66 g, 15.96 mmol) and compound a8 (6.94 g, 17.55 mmol) were completely dissolved in 260 mL of xylene, and then NaOtBu ( 2.30 g, 23.94 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.16 g, 0.32 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 8 (7.68 g, yield: 57%).

MS[M+H] ⁺ = 840

production example 9.

Compound 9-(1-(2'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-2-yl)-9H-carbazole (9-( 1-(2'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-2-yl)-9H-carbazole) (7.83 g, 16.31 mmol) and compound a9 (7.20 g, 17.94 mmol) After completely dissolving in 270 mL of xylene, NaOtBu (2.35 g, 24.47 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0) (0.17 g, 0.33 mmol) was added, and the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of tetrahydrofuran to prepare compound 9 (8.63 g, yield: 63%).

MS[M+H] ⁺ = 846

Example One.

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermally vacuum-depositing a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode. A hole transport layer was formed by vacuum-depositing a compound (1150 Å) represented by the following formula HT1 on the hole injection layer. Then, the compound of Preparation Example 1 was vacuum-deposited to a film thickness of 50 Å on the hole transport layer to form an electron blocking layer. Then, the compound represented by the following formula BH and the compound represented by the following formula BD to a film thickness of 200 Å on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing a compound represented by the following Chemical Formula HB1 to a film thickness of 50 Å on the light emitting layer. Then, on the hole blocking layer, the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10. ^{- 7} torr to 5 x 10 ^{- 6} torr was maintained, an organic light emitting device was manufactured.

Example 2 to 9.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1.

comparative example 1 to 6.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1. The compounds of EB2, EB3, EB4, EB5, EB6 and EB7 used in Table 1 below are as follows.

When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 denotes the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(Electronic blocking layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1 One 4.41 6.80 (0.144, 0.145) 255 Example 2 2 4.56 6.71 (0.147, 0.146) 240 Example 3 3 4.64 6.73 (0.146, 0.148) 245 Example 4 4 4.67 6.84 (0.145, 0.147) 240 Example 5 5 4.58 6.76 (0.146, 0.145) 235 Example 6 6 4.52 6.87 (0.147, 0.146) 245 Example 7 7 4.50 6.68 (0.146, 0.147) 230 Example 8 8 4.69 6.69 (0.145, 0.146) 235 Example 9 9 4.65 6.65 (0.147, 0.145) 240 Comparative Example 1 EB2 5.17 5.84 (0.147, 0.147) 85 Comparative Example 2 EB3 4.73 6.16 (0.146, 0.146) 70 Comparative Example 3 EB4 5.37 5.65 (0.146, 0.145) 55 Comparative Example 4 EB5 5.01 5.77 (0.145, 0.144) 60 Comparative Example 5 EB6 4.83 6.29 (0.146, 0.145) 155 Comparative Example 6 EB7 4.88 6.13 (0.147, 0.145) 160

As shown in Table 1, the organic light emitting device using the compound of the present invention as the electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.

On the other hand, the organic light-emitting device using a compound other than Chemical Formula 1 as the electron blocking layer showed a characteristic that the driving voltage increased and the efficiency and lifespan decreased.

Specifically, the compound in which the non-N ring portion of the carbazole group is substituted with a naphthalene group (EB2), the compound in which naphthalene is further substituted with an amine group and a substituent other than the carbazole group (EB3 and EB5), the substitution position of the amine group in naphthalene is Comparative Examples 1 to 6 in which other compounds (EB6 and EB7) and compounds (EB4) in which the substitution positions of the amine group and the carbazole group in naphthalene are all different (EB4) have higher driving voltages, and lower efficiency and lifespan compared to Examples 1 to 9 showed the characteristics of being

Although the preferred embodiment (electronic blocking layer) of the present invention has been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and the detailed description of the invention, and this belongs to the scope of the invention.

1: substrate
2: first electrode
3: light emitting layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: light emitting layer
8: electron transport layer
9: Electronic barrier layer
10: hole blocking layer
11: Electron injection and transport layer

Claims (7)

A compound of formula (1):
[Formula 1]

In Formula 1,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,
b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,
r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other. The method according to claim 1,
L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group. The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group. The method according to claim 1,
Formula 1 is a compound of any one of Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1 above,
R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
c is an integer of 1 to 4, and when c is 2 or more, 2 or more R3 are the same as or different from each other,
d is an integer of 1 to 4, and when d is 2 or more, 2 or more R4 are the same as or different from each other,
e is an integer of 1 to 4, and when e is 2 or more, 2 or more R 5 are the same or different. The method according to claim 1,
The compound of Formula 1 is any one of the following compounds:

a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 5. light emitting element. The organic light emitting device of claim 6 , wherein the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer includes the compound.

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