KR102626318B1 - Compound and organic light emitting device using the same - Google Patents

Abstract

The present application provides a compound that can significantly improve the lifespan, efficiency, electrochemical stability, and thermal stability of an organic light-emitting device, and an organic light-emitting device in which the compound is contained in an organic compound layer.

Description

Compound and organic light-emitting device using the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME}

This application relates to compounds and organic light-emitting devices using the same.

Electroluminescent devices are a type of self-luminous display devices and have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material of the organic thin film may have a light-emitting function as needed. For example, as an organic thin film material, a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material for the organic thin film, compounds that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

US Patent No. 4,356,429

A compound that can satisfy the conditions required for materials usable in organic light-emitting devices, such as appropriate energy level, electrochemical stability, and thermal stability, and has a chemical structure that can play various roles required in organic light-emitting devices depending on the substituent. Research on organic light-emitting devices containing is needed.

An exemplary embodiment of the present application provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

One of R1 to R4 is represented by the following formula 3, the other is represented by any of the following formulas 4 to 6, and the remainder is hydrogen,

R5 to R10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or selected from the group consisting of unsubstituted amine groups,

[Formula 3]

In Formula 3 above,

L1 is a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group,

R9 to R16 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or Two or more groups selected from the group consisting of unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted hydrocarbon condensed ring or heterocondensed ring,

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6,

L2 to L4 are the same or different from each other, and are each independently a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group,

At least one of X1 to X3 is N, and the others are each independently N or CR,

Ar2 to Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having C ₆ to C ₆₀ ; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group ; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

In addition, another embodiment of the present application is an organic light-emitting device comprising an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, wherein one or more layers of the organic material layer includes the compound represented by Formula 1 An organic light emitting device is provided.

In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, which simultaneously includes a compound represented by Formula 1 and a compound represented by Formula 2 below.

[Formula 2]

In Formula 2,

R1' to R4' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or Two or more groups selected from the group consisting of unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

L1' is a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group,

Ar1' is a substituted or unsubstituted aryl group having C ₆ to C ₆₀ ; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing at least one of S and O,

Ar2' is a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group ; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

m', p' and q' are each independently integers from 0 to 4,

n' is an integer from 0 to 2.

The compound according to an exemplary embodiment of the present application can be used as an organic layer material of an organic light-emitting device. The compound can be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a charge generation layer in an organic light emitting device. In particular, the compound represented by Formula 1 can be used as a material for the electron transport layer, hole transport layer, or light-emitting layer of an organic light-emitting device. In addition, when the compound represented by Formula 1 is used in an organic light-emitting device, the driving voltage of the device can be lowered, luminous efficiency can be improved, and the lifespan characteristics of the device can be improved due to the thermal stability of the compound.

Additionally, the compound represented by Formula 1 and the compound represented by Formula 2 can simultaneously be used as a material for the light-emitting layer of an organic light-emitting device. In addition, when the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 are used simultaneously in an organic light emitting device, the driving voltage of the device is lowered, the luminous efficiency is improved, and the lifespan characteristics of the device are improved by the thermal stability of the compound. can be improved.

1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present application.

The present application will be described in detail below.

The compound according to an exemplary embodiment of the present application is characterized by being represented by the above formula (1). More specifically, the compound represented by Formula 1 can be used as an organic layer material of an organic light-emitting device due to the structural characteristics of the core structure and substituents as described above.

According to an exemplary embodiment of the present application, R2 of Formula 1 may be represented by Formula 3, and R4 may be represented by any of Formulas 4 to 6.

According to an exemplary embodiment of the present application, R4 in Formula 1 may be represented by Formula 3, and R2 may be represented by any of Formulas 4 to 6.

According to an exemplary embodiment of the present application, R4 in Formula 1 may be represented by Formula 3, and R1 may be represented by any of Formulas 4 to 6.

According to an exemplary embodiment of the present application, R1 of Formula 1 may be represented by Formula 3, and R4 may be represented by any of Formulas 4 to 6.

According to an exemplary embodiment of the present application, Chemical Formula 3 may be represented by any of the following structural formulas.

In the above structural formula, X4 to

R17 to R23 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or Two or more groups selected from the group consisting of unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group ; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

m is an integer from 0 to 8, and n, o, p, q, r and s are each independently integers from 0 to 6.

In an exemplary embodiment of the present application, R5 to R8 in Formula 1 may each independently be hydrogen or deuterium.

In addition, the composition for the organic material layer of an organic light-emitting device according to an exemplary embodiment of the present application is characterized in that it simultaneously includes a compound represented by Formula 1 and a compound represented by Formula 2.

According to an exemplary embodiment of the present application, Formula 2 may be represented by any one of the following Formulas 11 to 22.

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

In Formulas 11 to 22, the definitions of L1, Ar1, Ar2, R1 to R4, m, n, p, and q are the same as those in Formula 2.

In an exemplary embodiment of the present application, when m', n', p', and q' of Formula 2 are each independently 2 or more, 2 or more R1' to R4' may be the same or different from each other.

In an exemplary embodiment of the present application, R1' to R4' in Formula 2 may each independently be hydrogen or deuterium.

In an exemplary embodiment of the present application, Ar1' of Formula 2 is a substituted or unsubstituted aryl group of C ₆ to C ₆₀ ; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing S; Or it may be a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing O.

In an exemplary embodiment of the present application, Ar1' of Formula 2 may be a phenyl group, a biphenyl group, a naphthyl group, a fluorene group substituted with an alkyl group, a dibenzothiophene group, or a dibenzofuran group.

In an exemplary embodiment of the present application, Ar2' of Formula 2 may be a substituted or unsubstituted aryl group of C ₆ to C ₆₀ .

In an exemplary embodiment of the present application, Ar2' in Formula 2 may be a phenyl group.

In the present application, the substituents of Formulas 1 and 2 are described in more detail as follows.

In this specification, “substituted or unsubstituted” means deuterium; halogen group; -CN; C ₁ to C ₆₀ alkyl group; C ₂ to C ₆₀ alkenyl group; C ₂ to C ₆₀ alkynyl group; C ₃ to C ₆₀ cycloalkyl group; C ₂ to C ₆₀ heterocycloalkyl group; C ₆ to C ₆₀ aryl group; C ₂ to C ₆₀ heteroaryl group; -SiRR'R"; -P(=O)RR'; C ₁ to C ₂₀ alkylamine group; C ₆ to C ₆₀ arylamine group; and substituted or unsubstituted with one or more substituents selected from the group consisting of C ₂ to C ₆₀ heteroarylamine groups, or substituted or unsubstituted with substituents in which two or more of the substituents are combined, or where two or more substituents selected from the above substituents are connected. It means substituted or unsubstituted with a substituent. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected. The additional substituents may be further substituted. R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cyclo An alkyl group; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

According to an exemplary embodiment of the present application, the "substituted or unsubstituted" refers to deuterium, halogen group, -CN, SiRR'R", P(=O)RR', C ₁ to C ₂₀ straight or branched alkyl group. , C ₆ to C ₆₀ aryl group, and C ₂ to C ₆₀ heteroaryl group, which is substituted or unsubstituted with one or more substituents selected from the group consisting of,

R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; -CN; deuterium, halogen group, -CN, C ₁ to C ₂₀ alkyl group, C ₆ to C ₆₀ aryl group, and a C ₁ to C ₆₀ alkyl group substituted or unsubstituted with a C ₂ to C ₆₀ heteroaryl group; deuterium, halogen, -CN, C ₁ to C ₂₀ alkyl group, C ₆ to C ₆₀ aryl group, and C ₂ C ₃ to C ₆₀ cycloalkyl group substituted or unsubstituted with C ₆₀ heteroaryl group; deuterium, halogen, -CN, C ₁ to C ₂₀ alkyl group, C ₆ to C ₆₀ aryl group, and C ₂ to C C ₆ to C ₆₀ aryl group substituted or unsubstituted with ₆₀ heteroaryl group; or deuterium, halogen, -CN, C ₁ to C ₂₀ alkyl group, C ₆ to C ₆₀ aryl group, and C ₂ to C ₆₀ It is a C ₂ to C ₆₀ heteroaryl group that is substituted or unsubstituted with a heteroaryl group.

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

In the present specification, the halogen may be fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.

In the present specification, the alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited to these.

In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the aryl group include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, and pyrethyl group. Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, and condensed rings thereof These may include, but are not limited to this.

In the present specification, the spiro group is a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group. Specifically, the spiro group below may include any one of the groups of the structural formula below.

In the present specification, the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, or aryl group. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, and thiazolyl group. group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyryl group, naphthyridyl group, acridinyl group, phenanthridide Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azacylinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido [1,2-b] indazolyl group, pyrido [1,2-a] imidazo [1,2-e] indolinyl group, 5,11-dihydroindeno [1,2-b ] Carbazolyl group, etc. may be mentioned, but it is not limited thereto.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH ₂ ; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms 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, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorescein Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited to these.

In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group. In addition, a heteroarylene group means that a heteroaryl group has two bonding positions, that is, a bivalent group. The description of the heteroaryl group described above can be applied, except that each of these is a divalent group.

According to an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

According to an exemplary embodiment of the present application, Formula 2 may be represented by any one of the following compounds, but is not limited thereto.

Additionally, by introducing various substituents into the structures of Formulas 1 and 2, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, the conditions required for each organic material layer are met. You can synthesize the desired substance.

In addition, by introducing various substituents into the structures of Formulas 1 and 2, the energy band gap can be finely adjusted, while improving the properties at the interface between organic materials and diversifying the uses of the material. .

Meanwhile, the compound has a high glass transition temperature (Tg) and has excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

A compound according to an exemplary embodiment of the present application can be manufactured through a multi-step chemical reaction. Some intermediate compounds are first prepared, and the compounds of Formula 1 or 2 can be prepared from the intermediate compounds. More specifically, the compound according to an exemplary embodiment of the present application can be manufactured based on the production example described later.

In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, characterized in that it simultaneously includes a compound represented by Formula 1 and a compound represented by Formula 2.

Specific details about the compound represented by Formula 1 and the compound represented by Formula 2 are the same as described above.

The weight ratio of the compound represented by Formula 1 to the compound represented by Formula 2 in the composition may be 1:10 to 10:1, 1:8 to 8:1, or 1:5 to 5:1. It may be 1:2 to 2:1, but is not limited thereto.

The composition can be used when forming an organic material of an organic light-emitting device, and can be particularly preferably used when forming a host for a light-emitting layer.

The composition is a simple mixture of two or more compounds, and powdered materials may be mixed before forming the organic material layer of the organic light-emitting device, or compounds in a liquid state at an appropriate temperature or higher may be mixed. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

Another embodiment of the present application provides an organic light-emitting device containing the compound represented by Formula 1 above.

In addition, the organic light-emitting device according to an exemplary embodiment of the present application includes an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, and at least one layer of the organic material layer is a compound represented by Formula 1, And it is characterized in that it includes a compound represented by the above formula (2).

The organic light-emitting device according to an exemplary embodiment of the present application is a typical organic light-emitting device, except that one or more organic layers are formed using the compound represented by the above-described formula 1 and the heterocyclic compound represented by formula 2. It can be manufactured using the manufacturing method and materials.

The compound represented by Formula 1 and the compound represented by Formula 2 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

Specifically, the organic light emitting device according to an exemplary embodiment of the present application includes an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, and at least one layer of the organic material layer contains the compound represented by Formula 1 above. Includes.

In addition, the organic light-emitting device according to an exemplary embodiment of the present application includes an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, and one or more layers of the organic material layers include a compound represented by Formula 1, and It includes a compound represented by Formula 2 above.

1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present application.

According to Figure 1, an organic light emitting device is shown in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure, and an organic light-emitting device may be implemented in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. 2.

Figure 3 illustrates the case where the organic material layer is multi-layered. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.

The organic light emitting device according to the present specification includes a compound represented by Formula 1 above in at least one layer of the organic material layer, or simultaneously contains a compound represented by Formula 1 and a compound represented by Formula 2. It can be manufactured using materials and methods known in the art.

The compound represented by Formula 1 may alone constitute one or more layers of the organic material layer of the organic light-emitting device. However, if necessary, it can be mixed with other materials to form an organic layer.

The compound represented by Formula 1 can be used as a material for an electron transport layer, hole blocking layer, and light emitting layer in an organic light emitting device. As an example, the compound represented by Formula 1 may be used as a material for the electron transport layer, hole transport layer, or light emitting layer of an organic light-emitting device.

Additionally, the compound represented by Formula 1 can be used as a material for an emission layer in an organic light-emitting device. As an example, the compound represented by Formula 1 can be used as a phosphorescent host material of the light-emitting layer in an organic light-emitting device.

In addition, the organic material layer containing the compound represented by Formula 1 and the compound represented by Formula 2 may further include other materials as needed.

The compound represented by Formula 1 and the compound represented by Formula 2 can be used as a material for a charge generation layer in an organic light-emitting device.

The compound represented by Formula 1 and the compound represented by Formula 2 can be used as materials for an electron transport layer, a hole blocking layer, and a light-emitting layer in an organic light-emitting device. As an example, the compound represented by Formula 1 and the compound represented by Formula 2 may be used as a material for an electron transport layer, a hole transport layer, or a light-emitting layer of an organic light-emitting device.

In addition, the compound represented by Formula 1 may be used as a material for the light-emitting layer in the organic light-emitting device represented by Formula 2. As an example, the compound represented by Formula 1 and the compound represented by Formula 2 may be used as a material for a phosphorescent host of a light-emitting layer in an organic light-emitting device.

In the organic light emitting device according to an exemplary embodiment of the present application, materials other than the compound of Formula 1 and the compound of Formula 2 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application. No, it can be replaced with materials known in the art.

As the anode material, materials with a relatively large work function can be used, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline are included, but are not limited to these.

As the cathode material, materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994). Starburst type amine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or poly( 3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) can be used.

As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

For example, LiF is typically used as an electron injection material in the industry, but the present application is not limited thereto.

Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material can be used as a light-emitting material, but it can also be used as a phosphorescent material. As a light-emitting material, a material that emits light by combining holes and electrons injected from an anode and a cathode, respectively, may be used, but materials that participate in light emission together with a host material and a dopant material may also be used.

When using a mixture of hosts of a light emitting material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials, such as an n-type host material or a P-type host material, can be selected and used as a host material for the light-emitting layer.

The organic light emitting device according to an exemplary embodiment of the present application may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.

The compound according to an exemplary embodiment of the present application may function in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

Below, the present specification is described in more detail through examples, but these are only for illustrating the present application and are not intended to limit the scope of the present application.

< Example >

< Synthesis example 1>

1) Preparation of Compound A-1

Compound methyl 2-iodobenzoate 21g (79.37mmol), 2-chloro-4-fluorophenyl boronic acid 16g (95.25mmol), Pd(PPh ₃ ) ₄ 4.58g (4mmol), K ₂ CO ₃ 32.9g (238mmol) toluene:ethanol:water 350:70:70mL was added and refluxed for 12 hours. After cooling to room temperature, extraction was performed using distilled water and dichloromethane. The organic layer was dried with MgSO ₄ , filtered using silica gel, and the solvent was removed to obtain 21 g (99%) of target compound A-1.

2) Preparation of Compound A

To a mixed solution containing 13 g (50.66 mmol) of Compound A-1 and 250 mL of THF, 39 mL (116.5 mmol) of 3M MeMgBr was added dropwise at room temperature, and stirred at 60°C for 12 hours. After cooling to room temperature, extraction was performed using distilled water and ethyl acetate. The organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. 350 mL of phosphoric acid and 250 mL of acetic acid were added to the residue and stirred at 120°C for 12 hours. The reaction product was cooled to room temperature and extracted using distilled water and dichloromethane. The organic layer was dried with MgSO ₄ , filtered using silica gel, and the solvent was removed to obtain 11.5 g (85%) of target compound A.

3) Preparation of Compound B

Compound A 11.5g (34mmol), bis(pinacolato)diborone 17.3g (68mmol), Pd(dba) ₂ 1.95g (3.4mmol), PCy ₃ 1.9g (6.8mmol), KOAc 10g (102mmol) 1,4 -120mL of dioxane was added and refluxed for 12 hours. After cooling to room temperature, extraction was performed using distilled water and dichloromethane. The organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was recrystallized from MeOH to obtain 12.8 g (85%) of target compound B.

< Synthesis example 2>

1) Preparation of Compound C-1

Compound A-1 of Synthesis Example 1, except that 2-chloro-5-fluoro boronic acid was used instead of 2-chloro-4-fluorophenyl boronic acid in the preparation of Compound A-1 of Synthesis Example 1. The target compound C-1 was obtained by preparing in the same manner as synthesis.

2) Preparation of Compound C

The target compound C was obtained in the same manner as the synthesis of Compound A in Synthesis Example 1, except that C-1 was used instead of A-1 in the preparation of Compound A in Synthesis Example 1.

3) Preparation of Compound D

Compound B of Synthesis Example 1 was prepared in the same manner as the synthesis of Compound B in Synthesis Example 1, except that C was used instead of A, and the target compound D was obtained.

< Synthesis example 3>

1) Preparation of compound E-1

Compound A-1 of Synthesis Example 1, except that 4-chloro-2-fluoro boronic acid was used instead of 2-chloro-4-fluorophenyl boronic acid in the preparation of Compound A-1 of Synthesis Example 1. The target compound E-1 was obtained by preparing in the same manner as synthesis.

2) Preparation of Compound E

The target compound E was obtained in the same manner as the synthesis of Compound A in Synthesis Example 1, except that E-1 was used instead of A-1.

3) Preparation of Compound F

The target compound F was obtained in the same manner as the synthesis of Compound B in Synthesis Example 1, except that E was used instead of A in the preparation of Compound B in Synthesis Example 1.

< Synthesis example 4>

1) Preparation of compound G-1

Compound A-1 of Synthesis Example 1, except that 5-chloro-2-fluorophenyl boronic acid was used instead of 2-chloro-4-fluorophenyl boronic acid in the preparation of Compound A-1 of Synthesis Example 1. The target compound G-1 was obtained by preparing in the same manner as the synthesis.

2) Preparation of Compound G

The target compound G was obtained in the same manner as the synthesis of Compound A in Synthesis Example 1, except that G-1 was used instead of A-1 in the preparation of Compound A in Synthesis Example 1.

3) Preparation of Compound H

The target compound H was obtained in the same manner as the synthesis of Compound B in Synthesis Example 1, except that G was used instead of A in the preparation of Compound B in Synthesis Example 1.

< Manufacturing example 1> Preparation of Compound 2

1) Preparation of compound 2-1

Compound D 10g (29.56mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine 12.19g (35.47mmol), Pd(PPh3 )4 1.7g (1.47mmol), K2CO3 12.25g (88.68mmol) 1,4-dioxane: 120mL of water were added and stirred under reflux for 12 hours. After cooling to room temperature, extraction was performed using distilled water and dichloromethane. The organic layer was dried with MgSO ₄ and then adsorbed on silica gel to obtain 12.28 g (80%) of target compound 2-1 using column chromatography purification (Hex:MC).

2) Preparation of Compound 2

10 g (19.24 mmol) of compound 2-1, 3.5 g (21.16 mmol) of 9H-carbazole, 31.34 g (96.2 mmol) of Cs ₂ CO ₃ and 100 mL of DMA were added and stirred under reflux for 12 hours. After cooling to room temperature, Cs ₂ CO ₃ was filtered, washed several times with dichloromethane, and then DMA and dichloromethane were concentrated. 9.36 g (73%) of target compound 2 was obtained by adsorption on silica gel and purification by column chromatography (Hex:MC).

< Manufacturing example 2> Preparation of compound 10

The target compound 10 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 3> Preparation of compound 14

The target compound 14 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 4> Preparation of compound 16

The target compound 16 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 5> Preparation of compound 18

The target compound 18 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 6> Preparation of compound 19

The target compound 19 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 7> Preparation of Compound 20

The target compound 20 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 8> Preparation of compound 21

The target compound 21 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 9> Preparation of Compound 22

The target compound 22 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 10> Preparation of Compound 41

The target compound 41 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 11> Preparation of compound 43

The target compound 43 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 12> Preparation of compound 47

The target compound 47 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 13> Preparation of compound 49

The target compound 49 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 14> Preparation of Compound 58

The target compound 58 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 15> Preparation of Compound 59

The target compound 59 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 16> Preparation of Compound 67

The target compound 67 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 17> Preparation of Compound 74

The target compound 74 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 18> Preparation of Compound 81

The target compound 81 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 19> Preparation of Compound 87

The target compound 87 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 20> Preparation of Compound 99

The target compound 99 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 21> Preparation of Compound 101

The target compound 101 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 22> Preparation of Compound 102

The target compound 102 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 23> Preparation of compound 113

The target compound 113 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 24> Preparation of Compound 114

The target compound 114 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 25> Preparation of Compound 115

The target compound 115 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 26> Preparation of Compound 116

The target compound 116 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 27> Preparation of Compound 129

The target compound 129 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 28> Preparation of Compound 130

The target compound 130 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 29> Preparation of Compound 135

The target compound 135 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 30> Preparation of Compound 140

The target compound 140 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 31> Preparation of Compound 149

The target compound 149 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 32> Preparation of Compound 150

The target compound 150 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 33> Preparation of Compound 163

The target compound 163 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 34> Preparation of Compound 164

The target compound 164 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 35> Preparation of Compound 177

The target compound 177 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 36> Preparation of Compound 178

The target compound 178 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 37> Preparation of Compound 184

The target compound 184 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 38> Preparation of Compound 185

The target compound 185 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 39> Preparation of Compound 190

The target compound 190 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 40> Preparation of Compound 191

The target compound 191 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 41> Preparation of Compound 197

The target compound 197 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 42> Preparation of Compound 198

The target compound 198 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 43> Preparation of Compound 202

The target compound 202 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 44> Preparation of Compound 203

The target compound 203 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 45> Preparation of Compound 211

The target compound 211 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 46> Preparation of Compound 216

The target compound 216 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 47> Preparation of Compound 218

The target compound 218 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 48> Preparation of Compound 241

The target compound 241 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

< Manufacturing example 49> Preparation of Compound 243

The target compound 243 was prepared in the same manner as the preparation of compound 2 in Preparation Example 1.

[Table 1]

Compounds were prepared in the same manner as in the above preparation examples, and the synthesis confirmation results are shown in Tables 2 and 3 below.

[Table 2]

[Table 3]

Table 2 is the NMR value, and Table 3 is the measurement value of FD-MS (Field desorption mass spectrometry).

< Experiment example >

< Experiment example 1>

A glass substrate coated with a thin film of ITO with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UV for 5 minutes using UV light in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) was formed on the ITO prepared as above as a hole injection layer, and NPB(N,N'-Di) was formed as a hole transport layer. (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed. The emitting layer was thermally vacuum deposited on the hole transport layer to form 400 Å.

The light-emitting layer was deposited with a host compound listed in Table 4, and was used as a phosphorescent dopant by doping 7% of Ir(ppy) ₃ (tris(2-phenylpyridine)iridium). Afterwards, BCP was deposited to a thickness of 60Å as a hole blocking layer, and Alq ₃ was deposited to a thickness of 200Å as an electron transport layer on top of it. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form the cathode, thereby forming an organic An electroluminescent device was manufactured.

The characteristics of the organic electroluminescent device of the present invention are shown in Table 4 below. For reference, Table 4 below shows device data obtained by simultaneously depositing one host compound from Experimental Example 1 as an individual source.

< Experiment example 2>

A glass substrate coated with a thin film of ITO with a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UV for 5 minutes using UV light in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

On the ITO transparent electrode (anode), a common hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB(N,N'-Di( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited at 400 Å with a constant ratio of one compound shown in Formula 1 and one compound shown in Formula 2 as a host, and the green phosphorescent dopant was deposited by doping 7% of Ir(ppy) ₃ . Afterwards, 60Å of BCP was deposited as a hole blocking layer, and Alq ₃ was deposited on top of it as an electron transport layer. 200Å was deposited. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form the cathode, thereby forming an organic An electroluminescent device was manufactured.

The characteristics of the organic electroluminescent device manufactured by Experimental Example 2 are shown in Table 5 below. Table 5 shows data on the device using the two compounds of Experimental Example 2 as hosts.

Meanwhile, all organic compounds required for manufacturing the OLED devices of Experimental Examples 1 and 2 were purified by vacuum sublimation under 10 ^-6 to ^{10 -8 torr} for each material and used for OLED manufacturing. In addition, the electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using the M7000 from McScience, and the standard luminance was measured using the lifespan measurement equipment (M6000) manufactured from McScience using the measurement results. When was 6,000 cd/m ² , T ₉₀ was measured.

[Comparative Compound A]

[Comparative compound B]

[Comparative compound C]

[Comparative compound D]

[Table 4] N-tpye host single deposition device characteristics

It was confirmed that the compound of the present invention was particularly superior in device life characteristics compared to comparative compounds B, C, and D. Compared to Comparative Compound B, the compound of the present application in which a fluorene substituent is substituted between carbazole and triazine is expected to have improved lifespan characteristics by reducing the band gap due to the effect of lengthening the conjugation length, and in the case of Comparative Compound C, fluorene In the case where carbalzol group and triazine group are substituted at positions 2 and 7, respectively, it has a flat molecular structure and may have crystallinity during deposition, so its lifespan is inevitably weak. In the case of comparative compound D, when only carbazole was substituted at positions 2 and 7 of fluorene, it was confirmed that the lifespan characteristics were deteriorated due to an imbalance in hole and electron transport.

[Table 5] P-tpye: N-tpye host simultaneous deposition device characteristics

The organic light-emitting device of the present invention includes a host and a light-emitting layer using a phosphorescent dopant, and the host is composed of a host compound (p-n type) that is a mixture of two or more compounds, and thus includes a host compound composed of a conventional single compound. It has the effect of having superior lifespan characteristics compared to organic light emitting devices.

In particular, the p-n type host system mixed with Chemical Formula 1 (n type host) and Chemical Formula 2 (p type host) has the advantage of increasing luminescent properties by adjusting the ratio of the host, which has good electron mobility. This is a result that can be achieved by an appropriate combination of Chemical Formula 1 and Chemical Formula 2, which has good hole mobility. In the case of comparative compounds A, B, C, and D, no significant improvement in lifespan was obtained even with two types of host composition.

100: substrate
200: anode
300: Organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (17)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
R4 is represented by any of the following structural formulas, any one of R1 to R3 is represented by any of the following formulas 4 to 6, and the remainder is hydrogen; or R4 is represented by any of the following formulas 4 to 6, any one of R1 to R3 is represented by any of the following structural formulas, and the remainder is hydrogen,
R5 to R10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or selected from the group consisting of unsubstituted amine groups,
[constitutional formula]



In the above structural formula,
X4 to X9 are the same or different from each other and are each independently NR, S, O or CR'R",
R17 to R23 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing one or more heteroatoms selected from O and S; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or Two or more groups selected from the group consisting of unsubstituted amine groups or adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,
m is an integer from 0 to 8, n, o, p, q, r and s are each independently an integer from 0 to 6,
[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6,
L2 to L4 are the same or different from each other, and are each independently a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group,
At least one of X1 to X3 is N, and the others are each independently N or CR,
Ar2 to Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having C ₆ to C ₆₀ ; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group ; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group. The compound according to claim 1, wherein R2 of Formula 1 is represented by any of the above structural formulas, and R4 is represented by any of the above formulas 4 to 6. The compound according to claim 1, wherein R4 in Formula 1 is represented by any of the above structural formulas, and R2 is represented by any of the above formulas 4 to 6. The compound according to claim 1, wherein R4 in Formula 1 is represented by any of the above structural formulas, and R1 is represented by any of the above formulas 4 to 6. The compound according to claim 1, wherein R1 of Formula 1 is represented by any of the above structural formulas, and R4 is represented by any of the above formulas 4 to 6. delete The compound according to claim 1, wherein R5 to R8 in Formula 1 are each independently hydrogen or deuterium. The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

An organic light-emitting device comprising an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 5, 7, and 8. The method according to claim 9, wherein the organic material layer includes at least one layer of a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one layer of the hole blocking layer, an electron injection layer, and an electron transport layer includes the compound. Organic light emitting device. The organic light-emitting device of claim 9, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound. The method of claim 9, wherein the organic material layer includes one or more layers among a hole injection layer, a hole transport layer, and a layer that simultaneously performs hole injection and hole transport, and one of the layers includes the compound. Organic light emitting device. The organic light-emitting device of claim 9, wherein the organic layer containing the compound further includes a compound represented by the following formula (2):
[Formula 2]

In Formula 2,
R1' to R4' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or Two or more groups selected from the group consisting of unsubstituted amine groups or adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,
L1' is a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group,
Ar1' is a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing at least one of S and O,
Ar2' is a substituted or unsubstituted aryl group having C ₆ to C ₆₀ ; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group ; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
m', p' and q' are each independently integers from 0 to 4,
n' is an integer from 0 to 2. The organic light-emitting device of claim 13, wherein Formula 2 is represented by any one of the following Formulas 11 to 22:
[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

In Formulas 11 to 22, the definitions of L1, Ar1, Ar2, R1 to R4, m, n, p, and q are the same as those in Formula 2. The organic light-emitting device according to claim 13, wherein Formula 2 is represented by any one of the following compounds:

A composition for an organic material layer of an organic light-emitting device, comprising simultaneously a compound according to any one of claims 1 to 5, 7, and 8 and a compound represented by the following formula (2):
[Formula 2]

In Formula 2,
R1' to R4' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; Substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; Substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; Substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; Substituted or unsubstituted C ₆ to C ₆₀ aryl group; Substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and substituted with a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a C ₂ to C ₆₀ heteroaryl group, or Two or more groups selected from the group consisting of unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,
L1' is a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group,
Ar1' is a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing at least one of S and O,
Ar2' is a substituted or unsubstituted aryl group having C ₆ to C ₆₀ ; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ alkyl group; substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group ; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
m', p' and q' are each independently integers from 0 to 4,
n' is an integer from 0 to 2. The composition for an organic material layer of an organic light-emitting device according to claim 16, wherein the weight ratio of the compound represented by Formula 1 to the compound represented by Formula 2 in the composition is 1:10 to 10:1.