KR102032598B1 - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device.

Description

Organic light emitting element {ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

Korean Patent Publication No. 2000-0051826

In this specification, an organic light emitting device is provided.

In one embodiment of the present specification,

anode;

A cathode provided to face the anode;

A light emitting layer provided between the anode and the cathode; And

An organic light emitting device comprising an organic material layer provided between the anode and the cathode,

The organic material layer provides an organic light emitting device comprising a compound represented by the following formula (1) and (2).

[Formula 1]

In Chemical Formula 1,

Two or more of R1 to R4 are cyano groups, and the others are the same or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R5 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted haloalkyl 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 heteroaryl group,

[Formula 2]

In Chemical Formula 2,

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

G1 to G4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic ring,

Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroaryl group,

R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r101 is an integer of 1 to 4,

r102 is an integer of 1 to 3,

r103 is an integer of 1 to 3,

r104 is an integer from 1 to 4,

When r101 to r104 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other,

a, b and z are integers from 0 to 4,

When a, b and z are each 2 or more, the structures in the two or more parentheses are the same or different from each other.

The organic light emitting device according to the exemplary embodiment of the present specification may lower the driving voltage, improve the light efficiency, and improve the life characteristics of the device by thermal stability of the compound.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
FIG. 3 includes a substrate 1, an anode 2 and a cathode 4, the hole injection layers 5a and 5b, the hole transport layers 6a and 6b, the light emitting layers 3a and 3b between the anode and the cathode. An example of an organic light emitting device including two units including electron transport layers 7a and 7b, and a charge generation layer 8 provided between the units, is shown.

Hereinafter, this specification is demonstrated in detail.

In an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is a TCNQ (Tetracyanoquinodimethane) derivative, and has high thermal stability and crystallization does not occur in a device process by changing molecular steric structure, and an organic light emitting device having high electron acceptability, In particular, when used in the hole injection layer, it is possible to realize a reduction in driving voltage and a long service life. In addition, since the solubility in organic solvents is high, an organic light emitting device having high purity can be manufactured.

In one embodiment of the present specification, the compound represented by the formula (2), in particular, the compound represented by the formula (3) and 4 in the substituent of the trisubstituted amine consists of a fluorene unit two substituents, having a low structure It was confirmed that the drive voltage, high efficiency and device stability.

In one embodiment of the present specification, the compound represented by the formula (2) comprising a compound represented by the formula (1) and an amine group excellent in hole injection and / or hole transport ability provided between the cathode and the light emitting layer (A) excellent hole injection properties when used as an injection layer and / or a hole transport layer; (B) high hole mobility; (C) good electron blocking force; (D) stable thin film state; And / or (E) excellent heat resistance and low voltage, high efficiency and long life.

Examples of substituents herein are described below, but are not limited thereto.

는 연결되는 부위를 의미한다.In the present specification,

Means a site to be connected.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Alkyl groups; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Alkenyl groups; Silyl groups; Boron group; Phosphine oxide groups; Amine group; Arylamine group; Aryl group; And one or two or more substituents selected from the group consisting of heteroaryl groups including one or more of N, O, S, Se, and Si atoms, or two or more substituents among the substituents exemplified above are substituted with a substituent, or any It means that it does not have a substituent.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

In this specification, although carbon number of a carbonyl group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In this specification, although carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the amino group may be substituted with a nitrogen of the amino group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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 40. 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 40 carbon atoms, 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, and the like, but are not limited thereto. Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ , R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ , and R ₁₀₁ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 50 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C40. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

,

,

,

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

,

,

,

,

,

Etc., but is not limited thereto.

In the present specification, the heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 6 to 50 carbon atoms. Examples of heteroaryl groups include thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, triazole groups, pyridyl groups, bipyridyl groups, pyrimidyl groups, triazine groups, triazole groups, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, and dibenzofura Although there exist a nil group etc., it is not limited to these.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent, represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same as or different from each other. Each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And a substituent consisting of at least one of a heterocyclic group, provided that at least one of R ₁₀₇ and R ₁₀₈ is not hydrogen. For example, -NH ₂ ; Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of N-alkylheteroarylamine group, monoheteroarylamine group and diheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenylamine group and the like, but is not limited thereto.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

In the present specification, the aryl group in the aryloxy group and the arylthioxy group is the same as the examples of the aryl group described above. Specifically, the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1- naphthyloxy group, 5-methyl-2- naphthyloxy group, 1- anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. Examples of the arylthioxy group include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned, but it is not limited to these.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

In the present specification, in a substituted or unsubstituted ring in which adjacent groups are formed by bonding to each other, a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

In the present specification, the heterocycle 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, Se, and S, and the like. The heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.

In one embodiment of the present specification, at least two of R1 to R4 are cyano groups, and the others are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R1 to R4 are cyano groups.

In one embodiment of the present specification, at least two of R1 to R4 are cyano groups, and the others are the same as or different from each other, and may be any one selected from the following structures.

In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted haloalkyl group.

In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, or a trifluoromethyl group.

In one embodiment of the present specification, R5 and R6 are hydrogen.

In one embodiment of the present specification, R5 and R6 are halogen groups.

In one embodiment of the present specification, R5 and R6 are fluorine.

In one embodiment of the present specification, R5 and R6 are trifluoromethyl group.

In one 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; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; Alkyl groups; Haloalkyl group; And an aryl group substituted with one or more of substituents selected from the group consisting of haloalkoxy groups, or hydrogen; heavy hydrogen; Cyano group; Halogen group; Alkyl groups; Haloalkyl group; And a heteroaryl group substituted with one or more of substituents selected from the group consisting of haloalkoxy groups.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; Alkyl groups; Haloalkyl group; And a phenyl group substituted with one or more of the substituents selected from the group consisting of haloalkoxy groups.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, cyano group, fluorine, methyl group, ethyl group, trifluoromethyl group, difluoromethoxy, trifluoromethoxy, Phenyl group substituted with at least one of the substituents selected from the group consisting of trifluoroethoxy and hexafluoromethoxy.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, cyano group, fluorine, methyl group, ethyl group, trifluoromethyl group, difluoromethoxy, trifluoromethoxy, A pyridine group substituted with at least one of the substituents selected from the group consisting of trifluoroethoxy and hexafluoromethoxy.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a naphthyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a quinazoline group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a thiophene group.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each directly connected directly.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a phenylene group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group , A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar3 is a fluorenyl group in which a phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar3 is a phenyl group, biphenyl group, terphenyl group, fluorenyl group, naphthyl group, dibenzothiophene group, dibenzofuran group, or carbazole group.

In one embodiment of the present specification, R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R101 to R104 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R101 to R104 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present specification, R101 to R104 are the same as or different from each other, and are each independently hydrogen.

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic ring.

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a ter-butyl group, a phenyl group, or a biphenyl group.

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently a phenyl group.

In one embodiment of the present specification, G1 and G2 or G3 and G4 are combined with the following Chemical Formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In one embodiment of the present specification, * is a site to which G1 and G2 or G3 and G4 are connected.

In one embodiment of the present specification, R105 to R110 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R105 to R110 are the same as or different from each other, and are each independently hydrogen.

In one embodiment of the present specification, Chemical Formula 2 may be represented by the following Chemical Formula 3 or 4.

[Formula 3]

[Formula 4]

In one embodiment of the present specification, the compound represented by Formula 1 may be any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by Formula 2 may be any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by Formula 3 may be any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by Formula 4 may be any one selected from the following compounds.

The organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. The structure is illustrated. In such a structure, the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.

In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer comprises a compound represented by the formula (1).

In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer comprises a compound represented by the formula (2).

In one embodiment of the present specification, the organic material layer includes a hole injection layer, and the hole injection layer is made of a compound represented by Formula 1 alone or a compound represented by Formula 1 is doped.

In one embodiment of the present specification, the organic material layer includes a doped hole injection layer, and the doped hole injection layer is formed by doping the compound represented by Formula 1 with the compound represented by Formula 2.

In one embodiment of the present specification, the organic material layer includes a hole injection layer and a hole transport layer, the hole injection layer comprises a compound represented by the formula (1), the hole transport layer is a compound represented by the formula (2) Include.

In one embodiment of the present specification, the organic material layer includes a hole injection layer and a hole transport layer, the hole injection layer is formed by doping the compound represented by the formula (1) to the compound represented by the formula (2), the hole The transport layer includes a compound represented by Chemical Formula 1.

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, and a light emitting layer, and the hole transport layer is positioned between the hole injection layer and the light emitting layer.

In one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, a hole control layer and a light emitting layer, wherein the hole transport layer is located between the hole injection layer and the hole control layer.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

 In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a physical vapor deposition (PVD: physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or an alloy thereof on the substrate It can be prepared by forming an anode, 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 cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

For example, the organic light emitting diode may have a laminated structure as described below, 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 injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

(4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

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

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

(7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

(9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

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

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

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

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

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

(15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, Mg / Ag, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode with a hole injection material, and has a capability of transporting holes with a hole injection material, and thus has a hole injection effect at an anode, and an excellent hole injection effect with respect to a light emitting layer or a light emitting material. The compound which prevents the movement of the excitons produced | generated in the light emitting layer to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The hole control layer effectively receives holes from the hole transport layer and serves to control hole mobility to adjust the amount of holes transferred to the light emitting layer. In addition, it may simultaneously serve as an electron barrier to prevent electrons supplied from the light emitting layer from falling into the hole transport layer. This can maximize the balance of holes and electrons in the light emitting layer to increase the luminous efficiency, improve the life of the device through the electron stability of the hole control layer, it is possible to use materials known in the art.

The light emitting material of the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the above-mentioned arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transporting material of the electron transporting layer is a layer for receiving electrons from the electron injection layer and transporting electrons to the light emitting layer. The electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. This large material is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the 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-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.

The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoconductor, an organic transistor, and the like.

The organic light emitting device of the present specification includes a material known in the art, except that the first organic material layer includes the compound represented by Chemical Formula 1, and the second organic material layer includes the compound represented by Chemical Formula 2. It can be prepared by the method.

In one embodiment of the present specification,

anode;

A cathode provided to face the anode; And

An organic light emitting device comprising a plurality of stacks provided between the anode and the cathode,

The plurality of stacks including respective light emitting layers, the first stack emitting light of at least a first color, and the second stack emitting light of a second color,

A charge generation layer between the first stack, the second stack, and the first stack and the second stack,

The charge generation layer includes an N-type charge generation layer positioned adjacent to the first stack and a P-type charge generation layer positioned adjacent to the second stack,

The P-type charge generation layer provides an organic light emitting device comprising a compound represented by the following formula (1) and (2).

[Formula 1]

In Chemical Formula 1,

Two or more of R1 to R4 are cyano groups, and the others are the same or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R5 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted haloalkyl 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 heteroaryl group,

[Formula 2]

In Chemical Formula 2,

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

G1 to G4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic ring,

Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroaryl group,

R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r101 is an integer of 1 to 4,

r102 is an integer of 1 to 3,

r103 is an integer of 1 to 3,

r104 is an integer from 1 to 4,

When r101 to r104 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other,

a, b and z are integers from 0 to 4,

When a, b and z are each 2 or more, the structures in the two or more parentheses are the same or different from each other.

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIG. 3.

3 includes a substrate 1, an anode 2 and a cathode 4, between the anode and the cathode, the hole injection layers 5a and 5b, the hole transport layers 6a and 6b and the light emitting layers 3a and 3b. And two units including electron transport layers 7a and 7b, and may be included in one or more layers of the charge generation layer 8 between the units.

In an exemplary embodiment of the present specification, the first stack and the second stack are each an organic material layer including a light emitting layer, and the organic material layer is a hole injection layer, a hole buffer layer, a hole transport layer, an electron suppression layer, a hole suppression layer, and an electron in addition to the light emitting layer. One or more organic material layers such as a transport layer and an electron injection layer may be further included.

In one embodiment of the present specification, the stack includes one or more selected from the group consisting of a hole injection layer, a hole transport layer, and a hole control layer.

In an exemplary embodiment of the present specification, the organic light emitting diode is provided between an anode and a cathode, includes two or more stacks including a light emitting layer, and includes a charge generating layer provided between the stacks.

In another exemplary embodiment, the organic light emitting diode includes a light emitting layer provided between an anode and a cathode and a charge generating layer provided between the cathode and the light emitting layer.

In one embodiment of the present specification, the P-type charge generating layer is made of a compound represented by Formula 1 alone or a compound represented by Formula 1 and a compound represented by Formula 2.

In one embodiment of the present specification, the N-type charge generation layer includes 5 wt% or less of lithium (Li).

In one embodiment of the present specification, the stack includes a hole injection layer, and the hole injection layer includes LUMO of 3.5 to 5.5 eV of the compound represented by Formulas 1 and 2. The value means an absolute value.

In the present specification, the LUMO energy level may be measured using cyclic voltammetry (CV) and spectroscopic methods (UV-Vis spectroscopy and Photoelectron spectroscopy (PS)) which are electrochemical methods.

According to another exemplary embodiment, the organic material layer may include two or more light emitting layers, and may include a charge generation layer including the compound of Formula 1 provided between the two light emitting layers. In this case, one of the light emitting layers emits blue light and the other emits yellow light, thereby manufacturing an organic light emitting device that emits white light. One or more organic material layers, such as the above-described hole injection layer, hole buffer layer, hole transport layer, electron suppression layer, hole suppression layer, electron transport layer, electron injection layer, between the light emitting layer and the anode or cathode, and between the light emitting layer and the charge generation layer May be included.

Hereinafter, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. Embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

< Example  1>

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

The above-described ATO transparent electrode was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. The hole transporting material B11 (900 kPa) was vacuum-deposited to form a hole transporting layer, and in turn, the host H1 and the dopant D1 (4 wt%) were vacuum deposited to a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the lithium fluoride was 0.2 0.2 / sec, and the aluminum was maintained at a deposition rate of 3 to 7 Å / sec.

< Example  2>

Except for using B52 instead of B11 in the hole transport layer in Example 1 was the same experiment.

< Example  3>

Except for using B144 instead of B11 as the hole transport layer in Example 1 was the same experiment.

< Example  4>

Except for using B204 instead of B11 as the hole transport layer in Example 1 was the same experiment.

< Example  5>

Except for using C11 instead of B11 as the hole transport layer in Example 1 was the same experiment.

< Example  6>

Except for using C69 instead of B11 as the hole transport layer in Example 1 was the same experiment.

< Example  7>

Except for using the D2 instead of B11 in the hole transport layer in Example 1 was the same experiment.

< Example  8>

Except for using D109 instead of B11 in the hole transport layer in Example 1 was the same experiment.

< Example  9>

The hole injection layer was formed by thermally vacuum depositing A1 described above on the ITO transparent electrode prepared in Example 1 to a thickness of 50 kPa. The hole transporting material HT1 (800 kPa) was vacuum-deposited thereon to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer. Vacuum deposition to a thickness of. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  10>

Except for using B236 instead of B144 as the hole control layer in Example 9 was the same experiment.

< Example  11>

Except for using C19 instead of B144 as the hole control layer in Example 9 was the same experiment.

< Example  12>

Except for using the D9 instead of B144 as the hole control layer in Example 9 was the same experiment.

< Example  13>

Except that in Example 9 B12 instead of HT1 as the hole transport layer, and C58 instead of B144 as the hole control layer was the same experiment.

< Example  14>

Except that in Example 9 B52 instead of HT1 as the hole transport layer, and C57 instead of B144 as the hole control layer was the same experiment.

< Example  15>

Except that in Example 9 B204 instead of HT1 as the hole transport layer, and D58 instead of B144 as the hole control layer was tested in the same manner.

< Example  16>

On the ITO transparent electrode prepared as in Example 1, the above-described A6 was thermally vacuum deposited to a thickness of 50 kPa to form a hole injection layer. The hole transporting material HT1 (900 kPa) was vacuum deposited to form a hole transporting layer, and the host H1 and the dopant D1 (4 wt%) were vacuum deposited to a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kV and aluminum 800 m thick were sequentially deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  17>

Except for using B12 instead of HT1 in the hole transport layer in Example 16 was the same experiment.

< Example  18>

The same experiment was conducted except that B203 was used instead of HT1 as the hole transport layer in Example 16.

< Example  19>

The same experiment was conducted except that B252 was used instead of HT1 as the hole transport layer in Example 16.

< Example  20>

Except for using C23 instead of HT1 in the hole transport layer in Example 16 was the same experiment.

< Example  21>

On the ITO transparent electrode prepared as in Example 1, the above-mentioned A6 was thermally vacuum deposited to a thickness of 50 kV to form a hole injection layer. The hole transporting material HT1 (800 kPa) was vacuum-deposited thereon to form a hole transporting layer. B144 (100 kPa) was formed thereon as a hole control layer, and the host H1 and the dopant D1 (4 wt%) were sequentially formed at 300 kPa. Vacuum deposition to a thickness of. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  22>

Except that in Example 21 B144 instead of HT1 as the hole transport layer, HT2 instead of B144 as the hole control layer was the same experiment.

< Example  23>

Except that in Example 21 B252 instead of HT1 as the hole transport layer, and D58 instead of B14 as the hole control layer was tested in the same manner.

< Example  24>

A7 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. The hole transporting material B12 (900 kPa) was vacuum-deposited to form a hole transporting layer, and in turn, the host H1 and the dopant D1 (4 wt%) were vacuum deposited to a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  25>

Except for using B61 instead of B12 as the hole transport layer in Example 24 was the same experiment.

< Example  26>

Except for using B144 instead of B12 as the hole transport layer in Example 24 was the same experiment.

< Example  27>

Except for using the HT1 instead of B12 as the hole transport layer in Example 24 was the same experiment.

< Example  28>

Except that in Example 24 C32 instead of B12 as the hole transport layer was the same experiment.

< Example  29>

Except for using the D69 instead of B12 as the hole transport layer in Example 24 was the same experiment.

< Example  30>

A7 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  31>

Except for using the D58 instead of B144 as the hole control layer in Example 30 was the same experiment.

< Example  32>

Except for using 144 instead of HT1 as the hole transport layer, B248 instead of B144 as the hole transport layer in Example 30 was the same experiment.

< Example  33>

Except for using 144 instead of HT1 as the hole transport layer, and C59 instead of B144 as the hole transport layer in Example 30 was the same experiment.

< Example  34>

On the ITO transparent electrode prepared as in Example 1, the above-mentioned A8 was thermally vacuum deposited to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, onto the host H1 and dopant D1 (4 wt%), in turn, by vacuum deposition at a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  35>

Except for using the B144 instead of HT1 as the hole transport layer in Example 34 was the same experiment.

< Example  36>

Except for using the B252 instead of HT1 as the hole transport layer in Example 34 was the same experiment.

< Example  37>

On the ITO transparent electrode prepared as in Example 1, the above-mentioned A8 was thermally vacuum deposited to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  38>

Except for using B204 instead of B144 as the hole control layer in Example 37 was the same experiment.

< Example  39>

Except that in Example 37 B144 instead of HT1 as the hole transport layer, HT2 instead of B144 as the hole control layer was the same experiment.

< Example  40>

Except that in Example 37 B144 instead of HT1 as the hole transport layer, B245 instead of B144 as the hole control layer was the same experiment.

< Example  41>

In Example 37, the same experiment was performed except that B252 was used instead of HT1 as the hole transport layer and HT2 was used instead of B144 as the hole control layer.

< Example  42>

Except that in Example 37 C69 instead of HT1 as the hole transport layer, and D58 instead of B144 as the hole control layer was the same experiment.

< Example  43>

On the ITO transparent electrode prepared as in Example 1, the above-described A14 was thermally vacuum deposited to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  44>

Except for using B52 instead of HT1 as the hole transport layer in Example 43 was the same experiment.

< Example  45>

Except for using the B144 instead of HT1 as the hole transport layer in Example 43 was the same experiment.

< Example  46>

Except for using B147 instead of HT1 as the hole transport layer in Example 43 was the same experiment.

< Example  47>

Except for using the C52 instead of HT1 as the hole transport layer in Example 43 was the same experiment.

< Example  48>

The same experiment was carried out in Example 43 except that D26 was used instead of HT1 as the hole transport layer.

< Example  49>

A14 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  50>

Except for using C58 instead of B144 as the hole control layer in Example 49 was the same experiment.

< Example  51>

The same experiment was performed in Example 49 except that B144 was used instead of HT1 as the hole transport layer and B245 was used instead of B144 as the hole control layer.

< Example  52>

Except for using D59 instead of B245 in the hole control layer in Example 51 was the same experiment.

< Example  53>

A16 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  54>

Doping was maintained in Example 53, except that B52 was used instead of HT1 as the hole transport layer.

< Example  55>

Doping was maintained in Example 53, except that B144 was used instead of HT1 as the hole transport layer.

< Example  56>

Doping was maintained in Example 53, except that B147 was used instead of HT1 as the hole transport layer.

< Example  57>

Doping was maintained in Example 53, except that C52 was used instead of HT1 as the hole transport layer.

< Example  58>

Doping was maintained in Example 53, except that D26 was used instead of HT1 as the hole transport layer.

< Example  59>

A16 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  60>

Except for using C58 instead of B144 as the hole control layer in Example 59 was the same experiment.

< Example  61>

The same experiment was performed in Example 59 except that B144 was used instead of HT1 as the hole transport layer and B245 was used instead of B144 as the hole control layer.

< Example  62>

Except for using the D59 instead of B245 as the hole control layer in Example 61 was the same experiment.

< Example  63>

A25 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  64>

Doping was maintained in Example 63, except that B144 was used instead of HT1 as the hole transport layer.

< Example  65>

Doping was maintained in Example 63, except that C34 was used instead of HT1 as the hole transport layer.

< Example  66>

A25 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  67>

Except that in Example 66 B144 instead of HT1 as the hole transport layer, HT2 instead of B144 as the hole control layer was the same experiment.

< Example  68>

The same experiment was performed in Example 66 except that B252 was used instead of HT1 as the hole transport layer and C59 was used instead of B144 as the hole control layer.

< Example  69>

The same experiment was performed in Example 66 except that C19 instead of HT1 was used as the hole transport layer, and HT2 instead of B144 was used as the hole control layer.

< Example  70>

The same experiment was performed in Example 66 except that D81 was used instead of HT1 as the hole transport layer and D56 was used instead of B144 as the hole control layer.

< Example  71>

A28 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  72>

Except for using the B61 instead of HT1 as the hole transport layer in Example 71 was the same experiment.

< Example  73>

Except for using B144 instead of HT1 as the hole transport layer in Example 71 was the same experiment.

< Example  74>

Except for using C2 instead of HT1 as the hole transport layer in Example 71 was the same experiment.

< Example  75>

Except for using the C19 instead of HT1 as the hole transport layer in Example 71 was the same experiment.

< Example  76>

Except for using the D64 instead of HT1 as the hole transport layer in Example 71 was the same experiment.

< Example  77>

A28 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  78>

Except for using C57 instead of B144 as the hole control layer in Example 77 was the same experiment.

< Example  79>

The same experiment as in Example 77 except that B144 was used instead of HT1 as the hole transport layer and B248 was used instead of B144 as the hole control layer.

< Example  80>

Except for using C58 instead of B248 in the hole control layer in Example 79 was the same experiment.

< Example  81>

A34 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  82>

The same experiment was conducted except that B144 was used instead of HT1 as the hole transport layer in Example 81.

< Example  83>

Except for using B147 instead of HT1 as the hole transport layer in Example 81 was the same experiment.

< Example  84>

The same experiment was carried out in Example 81 except that B236 was used instead of HT1 as the hole transport layer.

< Example  85>

Except for using C52 instead of HT1 as the hole transport layer in Example 81 was the same experiment.

< Example  86>

Except for using D119 instead of HT1 as the hole transport layer in Example 81 was the same experiment.

< Example  87>

A34 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  88>

Except for using the C57 instead of B144 as the hole control layer in Example 87 was the same experiment.

< Example  89>

The same experiment was performed in Example 87 except that B144 was used instead of HT1 as the hole transport layer and B248 was used instead of B144 as the hole control layer.

< Example  90>

The same experiment was conducted except that D58 was used instead of B248 as the hole control layer in Example 89.

< Example  91>

The hole injection layer was formed by thermally vacuum depositing A35 described above on the ITO transparent electrode prepared as in Example 1 to a thickness of 50 kPa. A hole transporting layer was formed by vacuum depositing HT1 (900 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  92>

The same experiment was conducted except that B144 was used instead of HT1 as the hole transport layer in Example 91.

< Example  93>

Except for using the D81 instead of HT1 as the hole transport layer in Example 91 was the same experiment.

< Example  94>

The hole injection layer was formed by thermally vacuum depositing A35 described above on the ITO transparent electrode prepared as in Example 1 to a thickness of 50 kPa. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  95>

The same experiment was performed in Example 94 except that B144 was used as the hole transport layer instead of HT1 and HT2 was used instead of B144 as the hole control layer.

< Example  96>

Except for using the B252 instead of HT1 as the hole transport layer in Example 94 was the same experiment.

< Example  97>

Except for using C69 instead of HT1 as the hole transport layer in Example 94 was the same experiment.

< Example  98>

In Example 94, the same experiment was conducted except that D64 was used instead of HT1 as the hole transport layer and D59 was used instead of B144 as the hole control layer.

< Example  99>

A79 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting layer was formed by vacuum depositing HT1 (800 kPa), which is a material for transporting holes, to form a hole transporting layer, followed by vacuum deposition of a host H1 and a dopant D1 (4 wt%) in a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  100>

Except for using the B144 instead of HT1 as the hole transport layer in Example 99 was the same experiment.

< Example  101>

Except for using C34 instead of HT1 as the hole transport layer in Example 99 was the same experiment.

< Example  102>

Except for using C69 instead of HT1 as the hole transport layer in Example 99 was the same experiment.

< Example  103>

In Example 99, the same experiment was performed except that D12 was used instead of HT1 as the hole transport layer.

< Example  104>

The same experiment was conducted except that D64 was used instead of HT1 as the hole transport layer in Example 99.

< Example  105>

A79 was formed on the ITO transparent electrode prepared in Example 1 by thermal vacuum deposition to a thickness of 50 kV to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Example  106>

Except for using B245 instead of B144 as the hole control layer in Example 105 was the same experiment.

< Example  107>

In Example 105, the same experiment was conducted except that B144 was used instead of HT1 as the hole transport layer and C57 was used instead of B144 as the hole control layer.

< Example  108>

Except for using the D56 instead of C57 as the hole control layer in Example 107 was the same experiment.

< Comparative example  1>

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

P1 described above was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. The hole transporting material HT1 (900 kPa) was vacuum deposited to form a hole transporting layer, and the host H1 and the dopant D1 (4 wt%) were vacuum deposited to a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the lithium fluoride was 0.2 0.2 / sec, and the aluminum was maintained at a deposition rate of 3 to 7 Å / sec.

< Comparative example  2>

P1 described above was thermally vacuum deposited to a thickness of 50 kPa on the ITO transparent electrode prepared as in Comparative Example 1 to form a hole injection layer. A hole transporting material was formed by vacuum evaporation of HT1 (800 kPa), a material for transporting holes, to form a hole transporting layer, and B144 (100 kPa) was formed thereon as a hole control layer, followed by the host H1 and the dopant D1 (4 wt%) Was vacuum deposited to a thickness of 300 mm 3. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Comparative example  3>

Except for using the D57 instead of B144 as the hole control layer in Comparative Example 2 was the same experiment.

< Comparative example  4>

Except for using the C59 instead of B144 as the hole control layer in Comparative Example 2 was the same experiment.

< Comparative example  5>

Except for using B245 instead of B144 as the hole control layer in Comparative Example 2 was the same experiment.

< Comparative example  6>

Except that in Comparative Example 2, B144 instead of HT1 as the hole transport layer, HT2 instead of B144 as the hole control layer was the same experiment.

< Comparative example  7>

In Comparative Example 2, except that B144 was used as the hole transport layer instead of HT1, and C57 was used instead of B144 as the hole control layer.

< Comparative example  8>

Except for using the B252 instead of HT1 as the hole transport layer and B248 instead of B144 as the hole transport layer in Comparative Example 2 was the same experiment.

< Comparative example  9>

Except for using the B252 instead of HT1 as the hole transport layer and D59 instead of B144 as the hole control layer in Comparative Example 2 was the same experiment.

< Comparative Example 10 >

A hole injection layer was formed by thermal vacuum deposition of HT1 to a thickness of 50 kPa on the ITO transparent electrode prepared as in Comparative Example 1, but P2 was doped at a doping concentration of 10%, and the hole transport layer was formed by vacuum deposition of HT1 (800 kPa). Subsequently, the host H1 and the dopant D1 (4% by weight) were vacuum deposited to a thickness of 300 kPa. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Comparative example  11>

Except for using the hole injection layer B144 instead of HT1 in Comparative Example 10 was the same experiment

< Comparative example  12>

A hole injection layer was formed by thermal vacuum deposition of HT1 to a thickness of 50 kPa on the prepared ITO transparent electrode as in Comparative Example 1, but P2 was doped at a doping concentration of 10%, and the hole transport layer was formed by vacuum deposition of HT1 (800 kPa). Then, HT2 (100 kPa) was formed thereon as a hole control layer, and then host H1 and dopant D1 (4 wt%) were vacuum deposited to a thickness of 300 kPa in sequence. Next, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) having a thickness of 10 kW and 800 kW of aluminum were deposited to form a cathode, thereby manufacturing an organic light emitting device. It was.

< Comparative example  13>

The same experiment was conducted except that B144 was used instead of HT2 as the hole control layer in Comparative Example 12.

< Comparative example  14>

Except for using the C57 instead of HT2 as the hole control layer in Comparative Example 12 was the same experiment.

< Comparative example  15>

In Comparative Example 12, the same experiment was performed except that B252 was used instead of HT1 as the hole injection layer and the hole transport layer, and D57 was used instead of HT2 as the hole control layer.

< Comparative example  16>

Except for using the B144 instead of HT1 as the hole injection layer and the hole transport layer in Comparative Example 12 was the same experiment.

< Comparative example  17>

In Comparative Example 12, the same experiment was conducted except that B144 was used instead of HT1 as the hole injection layer and the hole transport layer, and B248 was used instead of HT2 as the hole control layer.

Table 1 shows the results of measuring the voltage (V) and the luminous efficiency (cd / A) at a current density of 10 mAcm ^{- 2} for the organic EL devices manufactured according to Examples 1 to 108 and Comparative Examples 1 to 17. It described in 1.

In Examples 1 to 108 and Comparative Examples 1 to 17, it can be seen that the injection of holes is effectively generated using the P-charge injection material as a result of the blue organic EL single layer device. In the above results, it can be seen through the examples and comparative examples that the charge injection capacity of the dibenzo-TCNQ derivative of the compound represented by the present formula (1) as P type is superior to the known P1 or P2, the formula of the claim When the device is fabricated with the hole transport material shown in Fig. 1, it can be seen that the device shows a lower driving voltage and higher efficiency than the device result of the combination with other hole transport materials. In particular, the combination of diphenyl-TCNQ with B144 and B252 showed particularly good device tendency.

< Example  109>

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

The above-described ATO transparent electrode was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. The hole transporting material HT1 (200 kPa) was vacuum-deposited thereon to form a hole transporting layer, and in turn, the hosts H2, H3 and dopant D2 (20 wt%) were vacuum deposited to a thickness of 400 kPa. Next, an E1 compound (250 kV) was deposited to form an electron transport layer, and then, E2 and Li (2%) were vacuum deposited to a thickness of 100 kPa with a charge forming layer, and 1,000 m thick aluminum was deposited to form a cathode. A light emitting device was manufactured.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, and the deposition rate of lithium was 0.2 Å / sec and aluminum was 3 to 7 Å / sec.

< Example  110>

Except for using the hole transport layer B18 instead of HT1 in Example 109 was the same experiment.

< Example  111>

Except for using the hole transport layer B144 instead of HT1 in Example 109 was the same experiment.

< Example  112>

Except for using the hole transport layer C19 instead of HT1 in Example 109 was the same experiment.

< Example  113>

Except for using the hole transport layer C34 instead of HT1 in Example 109 was the same experiment.

< Example  114>

Except for using the hole transport layer D2 instead of HT1 in Example 109 was the same experiment.

< Example  115>

Except for using the hole injection layer A6 instead of A1 in Example 109 was the same experiment.

< Example  116>

Except for using the hole injection layer A6 in place of A1 in Example 109 and B144 instead of HT1 in the hole injection layer was the same experiment.

< Example  117>

Except for using the hole injection layer A6 instead of A1 in Example 109 and B12 instead of HT1 in the hole injection layer was the same experiment.

< Example  118>

Except for using the hole injection layer A6 in place of A1 in Example 109 and B252 instead of HT1 in the hole injection layer was the same experiment.

< Example  119>

Except for using the hole injection layer A6 in place of A1 in Example 109 and C69 instead of HT1 in the hole injection layer was the same experiment.

< Example  120>

Except for using the hole injection layer A6 in place of A1 in Example 109 and D2 instead of HT1 in the hole injection layer was the same experiment.

< Example  121>

Except for using the hole injection layer A6 instead of A1 in Example 109 and D81 instead of HT1 in the hole injection layer was the same experiment.

< Example  122>

Except for using the hole injection layer A7 instead of A1 in Example 109 was the same experiment.

< Example  123>

Except for using the hole injection layer A7 instead of A1 and the hole transport layer B52 instead of HT1 in Example 109 was the same experiment.

< Example  124>

Except for using the hole injection layer A7 instead of A1 and the hole transport layer B144 instead of HT1 in Example 109 was the same experiment.

< Example  125>

Except for using the hole injection layer A7 in place of A1 in Example 109 and B252 instead of HT1 in the hole injection layer was the same experiment.

< Example  126>

Except for using the hole injection layer A7 instead of A1 and C52 instead of HT1 in Example 109 was the same experiment.

< Example  127>

Except for using the hole injection layer A7 in place of A1 in Example 109 and D26 instead of HT1 in the hole injection layer was the same experiment.

< Example  128>

Except for using the hole injection layer A8 instead of A1 in Example 109 was the same experiment.

< Example  129>

Except for using the hole injection layer A8 instead of A1 and the hole transport layer B144 instead of HT1 in Example 109 was the same experiment.

< Example  130>

Except for using the hole injection layer A8 instead of A1 and the hole transport layer B11 instead of HT1 in Example 109 was the same experiment.

< Example  131>

Except for using the hole injection layer A8 instead of A1 and the hole transport layer B236 instead of HT1 in Example 109 was the same experiment.

< Example  132>

Except for using the hole injection layer A8 instead of A1 and the hole transport layer B252 instead of HT1 in Example 109 was the same experiment.

< Example  133>

Except for using the hole injection layer A8 instead of A1 in Example 109 and C52 instead of HT1 for the hole injection layer was the same experiment.

< Example  134>

Except for using the hole injection layer A8 instead of A1 in Example 109 and D58 instead of HT1 for the hole injection layer was the same experiment.

< Example  135>

Except for using the hole injection layer A14 instead of A1 in Example 109 was the same experiment.

< Example  136>

Except for using the hole injection layer A14 instead of A1 in Example 109 and B11 instead of HT1 in the hole injection layer was the same experiment.

< Example  137>

Except for using the hole injection layer A14 instead of A1 in Example 109 and B144 instead of HT1 in the hole injection layer was the same experiment.

< Example  138>

Except for using the hole injection layer A14 instead of A1 in Example 109 and B252 instead of HT1 in the hole injection layer was the same experiment.

< Example  139>

Except for using the hole injection layer A14 instead of A1 in Example 109 and D32 instead of HT1 for the hole injection layer was the same experiment.

< Example  140>

Except for using the hole injection layer A14 instead of A1 in Example 109 and D52 instead of HT1 in the hole injection layer was the same experiment.

< Example  141>

Except for using the hole injection layer A25 instead of A1 in Example 109 was the same experiment.

< Example  142>

Except for using the hole injection layer A25 instead of A1 in Example 109 and B144 instead of the hole transport layer was tested in the same manner.

< Example  143>

Except for using the hole injection layer A25 instead of A1 in Example 109 and B236 instead of HT1 hole experiment was the same experiment.

< Example  144>

Except for using the hole injection layer A25 in place of A1 in Example 109 and B252 instead of HT1 in the hole injection layer was the same experiment.

< Example  145>

Except for using the hole injection layer A25 in place of A1 in Example 109 and C30 instead of HT1 in the hole injection layer was the same experiment.

< Example  146>

Except for using the hole injection layer A25 instead of A1 and C56 instead of HT1 in Example 109 was the same experiment.

< Example  147>

Except for using the hole injection layer A25 in place of A1 in Example 109 and D8 instead of HT1 in the hole injection layer was the same experiment.

< Example  148>

Except for using the hole injection layer A28 instead of A1 in Example 109 was the same experiment.

< Example  149>

Except for using the hole injection layer A28 instead of A1 and the hole transport layer B144 instead of HT1 in Example 109 was the same experiment.

< Example  150>

Except for using the hole injection layer A28 in place of A1 in Example 109 and B20 instead of HT1 in the hole injection layer was the same experiment.

< Example  151>

Except for using the hole injection layer A28 in place of A1 in Example 109 and B20 instead of HT1 in the hole injection layer was the same experiment.

< Example  152>

Except for using the hole injection layer A28 instead of A1 and the hole transport layer B206 instead of HT1 in Example 109 was the same experiment.

< Example  153>

Except for using the hole injection layer A28 instead of A1 in Example 109 and C69 instead of HT1 hole experiment was the same experiment.

< Example  154>

Except for using the hole injection layer A28 instead of A1 in Example 109 and D119 instead of HT1 in the hole injection layer was the same experiment.

< Example  155>

Except for using the hole injection layer A34 instead of A1 in Example 109 was the same experiment.

< Example  156>

Except for using the hole injection layer A34 instead of A1 in Example 109 and B144 instead of HT1 in the hole injection layer was the same experiment.

< Example  157>

Except for using the hole injection layer A34 instead of A1 and the hole transport layer B252 instead of HT1 in Example 109 was the same experiment.

< Example  158>

Except for using the hole injection layer A34 instead of A1 in Example 109 and D2 instead of HT1 in the hole injection layer was the same experiment.

< Example  159>

Except for using the hole injection layer A34 in place of A1 in Example 109 and D64 instead of HT1 in the hole injection layer was the same experiment.

< Example  160>

Except for using the hole injection layer A34 instead of A1 in Example 109 and D119 instead of HT1 in the hole injection layer was the same experiment.

< Example  161>

Except for using the hole injection layer A35 instead of A1 in Example 109 was the same experiment.

< Example  162>

Except for using the hole injection layer A35 instead of A1 and the hole transport layer B144 instead of HT1 in Example 109 was the same experiment.

< Example  163>

Except for using the hole injection layer A35 instead of A1 in the Example 109 and B2 instead of HT1 in the hole injection layer was the same experiment.

< Example  164>

Except for using the hole injection layer A35 instead of A1 and the hole transport layer B204 instead of HT1 in Example 109 was the same experiment.

< Example  165>

Except for using the hole injection layer A35 instead of A1 and the hole transport layer B252 instead of HT1 in Example 109 was the same experiment.

< Example  166>

Except for using the hole injection layer A35 instead of A1 and C70 instead of HT1 in Example 109 was the same experiment.

< Example  167>

Except for using the hole injection layer A35 in place of A1 in Example 109 and D32 instead of HT1 in the hole injection layer was the same experiment.

< Example  168>

Except for using the hole injection layer A79 instead of A1 in Example 109 was the same experiment.

< Example  169>

Except for using the hole injection layer A79 instead of A1 and the hole transport layer B61 instead of HT1 in Example 109 was the same experiment.

< Example  170>

Except for using the hole injection layer A79 instead of A1 and the hole transport layer B144 instead of HT1 in Example 109 was the same experiment.

< Example  171>

Except for using the hole injection layer A79 instead of A1 and the hole transport layer B146 instead of HT1 in Example 109 was the same experiment.

< Example  172>

Except for using the hole injection layer A79 instead of A1 and the hole transport layer B236 instead of HT1 in Example 109 was the same experiment.

< Example  173>

Except for using the hole injection layer A79 instead of A1 and the hole transport layer B252 instead of HT1 in Example 109 was the same experiment.

< Comparative example  18>

P1 described above was thermally vacuum deposited to a thickness of 50 kPa on the ITO transparent electrode prepared as in Example 1 to form a hole injection layer. The hole transporting material HT1 (200 kPa) was vacuum-deposited to form a hole transporting layer, and in turn, the hosts H2, H3 and dopant D2 (20 wt%) were vacuum deposited to a thickness of 400 kPa. Next, an E1 compound (250 kV) was deposited to form an electron transport layer, and then, E2 and Li (2%) were vacuum deposited to a thickness of 100 kPa with a charge forming layer, and 1,000 m thick aluminum was deposited to form a cathode. A light emitting device was manufactured.

< Comparative example  19>

In Comparative Example 18, the hole transport layer was tested in the same manner except that B61 was used instead of HT1.

< Comparative example  20>

Except for using the hole transport layer 144 instead of HT1 in Comparative Example 18 was the same experiment.

< Comparative example  21>

Except for using the hole transport layer in Comparative Example 18 C52 instead of HT1 was the same experiment.

< Comparative example  21>

Except for using the hole transport layer D26 instead of HT1 in Comparative Example 18 was the same experiment.

< Comparative example  23>

A hole injection layer was formed by thermal vacuum deposition of HT1 to a thickness of 50 kPa on the prepared ITO transparent electrode as in Comparative Example 1, but P2 was doped with a doping concentration of 10%, and HT1, a material for transporting holes, was formed thereon (200 kPa). Was deposited in vacuo to form a hole transporting layer, and in turn vacuum evaporated to host H2, H3 and dopant D2 (20 wt. Next, an E1 compound (250 kV) was deposited to form an electron transport layer, and then, E2 and Li (2%) were vacuum deposited to a thickness of 100 kPa with a charge forming layer, and 1,000 m thick aluminum was deposited to form a cathode. A light emitting device was manufactured.

< Comparative example  24>

In Comparative Example 23, the hole injection layer and the hole transport layer were tested in the same manner except that B144 was used instead of HT1.

< Comparative example  25>

In Comparative Example 23, the hole injection layer and the hole transport layer were tested in the same manner except that B252 was used instead of HT1.

< Comparative example  26>

In Comparative Example 23, the hole injection layer and the hole transport layer were tested in the same manner except that C52 was used instead of HT1.

Example 109 to 173 and Comparative Examples 18 to with respect to the organic EL device manufactured by the 26, 10mAcm ^- The results of measuring a voltage (V) and luminous efficiency (cd / A) at the current density of the ^second table 2 is described.

Table 2 is a result of the green organic EL single-layer device of Examples 109 to 173 and Comparative Examples 18 to 26, A1, A6, A7, A8, A14, A34, A25, A28, A34 , A green light emitting device fabricated using the diphneyl TCNQ derivatives corresponding to A35 and A79 and the HTL materials of the structure shown in the above claims has a lower driving voltage, compared with the combination of another hole injection layer and a hole injection layer and a hole transport layer. It can be seen that high efficiency is achieved.

In the results of the green organic light-emitting monolayer device, the combination of diphenyl-TCNQ with B144 and B252 shows particularly good device tendency.

[White EL element]

< Example  180>

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

[Formation of Green Light Emitting Device]

As described above, the hole injection layer was formed by thermally vacuum depositing P1 on the ITO transparent electrode to a thickness of 50 kPa. The hole transporting material B144 (200 kPa) was vacuum deposited on the substrate to form a hole transporting layer, and the host H2, H3 and dopant D2 (20 wt%) were vacuum deposited to a thickness of 400 kPa to form a green light emitting layer. Next, an E1 compound (250 cc) was deposited.

Subsequently, a charge forming layer was formed.

On the electron transporting layer of the light emitting unit, E 2 and Li (2%) were formed to a thickness of 100 kV as an N-charge forming layer. Subsequently, A1 described above was formed to a thickness of 50 GPa as a P-charge forming layer.

[Formation of Blue Light-Emitting Element]

 Next to the charge forming layer, blue was formed by the second light emitting unit.

HT1, a material for transporting holes, was vacuum deposited on the charge forming layer to form a hole transporting layer, and in turn, the host H1 and the dopant D1 (4 wt%) were vacuum deposited to a thickness of 300 kPa. Then, the E1 compound was formed into an electron transport layer with Liq 1: 1 (300 kV), and subsequently, lithium fluoride (LiF) of 10 kV and aluminum of 800 kW were deposited to form a cathode to form a white organic EL device. Prepared.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the lithium fluoride was 0.2 0.2 / sec, and the aluminum was maintained at a deposition rate of 3 to 7 Å / sec.

< Example  175 to 198 and Comparative example  27 to 28>

As in Example 180, the configuration of the white EL device was configured in the same manner as in Table 3, and the same experiment was performed.

In addition, the results of measuring the voltage (V) and the luminous efficiency (cd / A) at a current density of 10 mAcm ^-2 for the organic EL devices manufactured according to Examples 175 to 198 and Comparative Examples 27 to 28 were obtained. It is listed in Table 3 below.

As a result of comparing Examples 175 to 198 and Comparative Examples 27 to 28 through the combination, it was found that the blue and green organic light emitting diodes and the stacked white light emitting diodes had strengths in material synthesis and device driving.

Although the preferred embodiment of the present invention has been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also belong to the scope of the invention. .

1: substrate
2: anode
3: light emitting layer
4: cathode
5, 5a, 5b: hole injection layer
6, 6a, 6b: hole transport layer
7, 7a, 7b: electron transport layer
8: charge generation layer

Claims (22)

anode;
A cathode provided to face the anode;
A light emitting layer provided between the anode and the cathode; And
An organic light emitting device comprising an organic material layer provided between the anode and the cathode,
The organic material layer is an organic light emitting device comprising a compound represented by the following formula (1) and (2):
[Formula 1]

In Chemical Formula 1,
Two or more of R1 to R4 are cyano groups, and the others are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R5 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted haloalkyl group,
Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; Alkyl groups; Haloalkyl group; And a haloalkoxy group is substituted with at least one substituent selected from the group consisting of, at least one is an aryl group substituted with a haloalkoxy group,
[Formula 2]

In Chemical Formula 2,
L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
G1 to G4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic ring,
Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroaryl group,
R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r101 is an integer of 1 to 4,
r102 is an integer of 1 to 3,
r103 is an integer of 1 to 3,
r104 is an integer from 1 to 4,
When r101 to r104 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other,
a, b and z are integers from 0 to 4,
When a, b and z are each 2 or more, the structures in the two or more parentheses are the same or different from each other. The organic light emitting device of claim 1, wherein at least two of R1 to R4 are cyano groups, and the others are the same as or different from each other, and are selected from the following structures:

delete The organic light emitting diode of claim 1, wherein G1 and G2 or G3 and G4 are combined with Formula 2-1 or 2-2.
[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,
* Is the site where G1 and G2 or G3 and G4 are linked,
R105 to R110 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r105 is an integer from 1 to 4,
r 106 is an integer from 1 to 4,
r107 is an integer of 1 to 5,
r108 is an integer from 1 to 4,
r109 is an integer of 1 to 3,
r110 is an integer of 1 to 4,
When r105 to r110 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other. The organic light emitting diode of claim 1, wherein Chemical Formula 2 is represented by Chemical Formula 3 or 4.
[Formula 3]

[Formula 4]

In Chemical Formulas 3 and 4,
The definitions for L1 to L3, G3, G4, Ar3, R101 to R104, r101 to r104, a, b and z are the same as those defined in Chemical Formula 2,
R105 to R107 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
In Chemical Formula 3, r105 is an integer of 1 to 4, r106 is an integer of 1 to 4, r107 is an integer of 1 to 5,
In Chemical Formula 4, r105 is an integer of 1 to 3, r106 is an integer of 1 to 4, r107 is an integer of 1 to 4,
When r105 to r107 are each two or more, the structures in two or more parentheses are the same as or different from each other. The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 1 is selected from the following compounds:

The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 2 is selected from the following compounds:

The organic light emitting diode of claim 5, wherein the compound represented by Chemical Formula 3 is selected from the following compounds:

The organic light emitting diode of claim 5, wherein the compound represented by Chemical Formula 4 is selected from the following compounds:

The organic light emitting device of claim 1, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes a compound represented by Chemical Formula 1. The organic light emitting device of claim 1, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes a compound represented by Chemical Formula 2. The organic light emitting device of claim 1, wherein the organic material layer includes a hole injection layer, and the hole injection layer is formed of a compound represented by Formula 1 alone or a compound represented by Formula 1 doped. The organic light emitting device of claim 1, wherein the organic material layer includes a doped hole injection layer, and the doped hole injection layer is formed by doping the compound represented by Formula 1 with the compound represented by Formula 2. The method of claim 1, wherein the organic material layer comprises a hole injection layer and a hole transport layer, the hole injection layer comprises a compound represented by the formula (1), the hole transport layer comprises a compound represented by the formula (2) Organic light emitting device. The method according to claim 1, wherein the organic layer comprises a hole injection layer and a hole transport layer, the hole injection layer is formed by doping the compound represented by the formula (1) to the compound represented by the formula (2), the hole transport layer is An organic light emitting device comprising the compound represented by 1. The organic light emitting device of claim 1, wherein the organic material layer includes a hole injection layer, a hole transport layer, and a light emitting layer, and the hole transport layer is positioned between the hole injection layer and the light emitting layer. The organic light emitting device of claim 1, wherein the organic material layer includes a hole injection layer, a hole transport layer, a hole control layer, and a light emitting layer, and the hole transport layer is positioned between the hole injection layer and the hole control layer. anode;
A cathode provided to face the anode; And
An organic light emitting device comprising a plurality of stacks provided between the anode and the cathode,
The plurality of stacks including respective light emitting layers, the first stack emitting light of at least a first color, and the second stack emitting light of a second color,
A charge generation layer between the first stack, the second stack, and the first stack and the second stack,
The charge generation layer includes an N-type charge generation layer positioned adjacent to the first stack and a P-type charge generation layer positioned adjacent to the second stack,
The P-type charge generating layer is an organic light emitting device comprising a compound represented by Formula 1 below or a compound represented by Formula 1 and a compound represented by Formula 1 below:
[Formula 1]

In Chemical Formula 1,
Two or more of R1 to R4 are cyano groups, and the others are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R5 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted haloalkyl group,
Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; Alkyl groups; Haloalkyl group; And a haloalkoxy group is substituted with at least one substituent selected from the group consisting of, at least one is an aryl group substituted with a haloalkoxy group,
[Formula 2]

In Chemical Formula 2,
L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
G1 to G4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic ring,
Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl alkenyl group; Or a substituted or unsubstituted heteroaryl group,
R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r101 is an integer of 1 to 4,
r102 is an integer of 1 to 3,
r103 is an integer of 1 to 3,
r104 is an integer from 1 to 4,
When r101 to r104 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other,
a, b and z are integers from 0 to 4,
When a, b and z are each 2 or more, the structures in the two or more parentheses are the same or different from each other. The organic light emitting device of claim 18, wherein the stack comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, and a hole control layer. delete The organic light-emitting device as claimed in claim 18, wherein the N-type charge generation layer comprises 5 wt% or less of lithium (Li). The organic light emitting device of claim 18, wherein the stack includes a hole injection layer, and the hole injection layer is comprised of 3.5 to 5.5 eV LUMO of the compound represented by Chemical Formulas 1 and 2.

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