KR20210068935A - Compound and organic light emitting device including the same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same. The compound described in the present specification can be used as an organic material layer of the organic light emitting device. The compound can serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device.

Description

Compound and organic light emitting device including the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE INCLUDING THE SAME}

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

The electroluminescent device is a type of self-luminous display device, and has a wide viewing angle, excellent contrast, and fast response speed.

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

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

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

U.S. Patent No. 4,356,429

An object of the present specification is to provide a compound and an organic light emitting device including the same.

In an exemplary embodiment of the present specification, a compound represented by the following Chemical Formula 1 is provided.

[Formula 1]

In Formula 1,

R1 and R2 are each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 60 alkyl group; a 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,

L, L', L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,

a, b, m and n are each an integer from 1 to 3;

When a, b, m and n are each 2 or more, the substituents in parentheses are the same as or different from each other,

Z, Ar1 and Ar2 are each independently a cyano group; halogen group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the following formula (A),

[Formula A]

In the formula A,

A ₁ and A ₂ are each independently, a substituted or unsubstituted C 1 to C 60 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,

R _a is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a 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,

r is an integer from 1 to 4,

When r is 2 or more, two or more R _a are the same as or different from each other.

In addition, according to an exemplary embodiment of the present application, the first electrode; a second electrode provided to face the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes at least one compound represented by Formula 1 above.

The compound described herein can be used as an organic material layer of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting device. In particular, the compound can be used as a material for a hole transport layer and an electron blocking layer of an organic light emitting device.

Formula 1 has at least one substituent on both benzene rings of 9,9-dimethyl-9H-fluorene, and at least one of the substituents is an amine group. In addition, in the case of a fluorene group having a substituent, π-π stacking of the aromatic ring is suppressed, and accordingly, the driving voltage of the organic light emitting device is increased to prevent deterioration of device characteristics. In particular, when a compound of Formula 1 is used as a material for a hole transport layer or an electron blocking layer of an organic light emitting device, since a substituent is introduced at the 4th position of the fluorene group, steric hindrance occurs, and this increases the T1 value. , it is possible to lower the driving voltage of the device, improve the light efficiency, and improve the lifespan characteristics of the device.

In addition, when the compound of Formula 1 is used as a material for the hole transport layer or the electron blocking layer of the organic light emitting device, the driving voltage of the device may be lowered, the light efficiency may be improved, and the lifespan characteristics of the device may be improved.

1 to 4 are diagrams exemplarily showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present specification.

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

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

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

는 치환되는 위치를 의미한다.In this specification,

means a position to be substituted.

In the present specification, "substituted or unsubstituted" refers to a C1 to C60 linear or branched alkyl group; C2 to C60 linear or branched alkenyl group; C2 to C60 linear or branched alkynyl group; C3 to C60 monocyclic or polycyclic cycloalkyl group; C2 to C60 monocyclic or polycyclic heterocycloalkyl group; C6 to C60 monocyclic or polycyclic aryl group; C2 to C60 monocyclic or polycyclic heteroaryl group; silyl group; phosphine oxide group; And it means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an amine group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-described substituents are connected.

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

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, 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, and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a 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 are not limited thereto.

In the present specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, 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 other substituents. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, 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, and the like, but is not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, 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 other substituents. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

In the present specification, the aryl group includes a monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The aryl group includes a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, pyreth Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is 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, and is 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; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

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

,

,

,

,

,

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

,

,

,

,

,

and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes O, S, SO ₂ Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, thiazolyl 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, quinozolilyl group, naphthyridyl group, acridinyl group, phenanthridyl group Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene 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, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, benzofuro[2,3-d]pyrimidyl group; benzothieno[2,3-d] pyrimidyl group; Benzofuro[2,3-a]carbazolyl group, benzothieno[2,3-a]carbazolyl group, 1,3-dihydroindolo[2,3-a]carbazolyl group, benzofuro [3,2-a] carbazolyl group, benzothieno [3,2-a] carbazolyl group, 1,3-dihydroindolo [3,2-a] carbazolyl group, benzofuro [2, 3-b] carbazolyl group, benzothieno [2,3-b] carbazolyl group, 1,3-dihydroindolo [2,3-b] carbazolyl group, benzofuro [3,2-b ]carbazolyl group, benzothieno[3,2-b]carbazolyl group, 1,3-dihydroindolo[3,2-b]carbazolyl group, benzofuro[2,3-c]carbazolyl group Group, benzothieno[2,3-c]carbazolyl group, 1,3-dihydroindolo[2,3-c]carbazolyl group, benzofuro[3,2-c]carbazolyl group, benzo Thieno [3,2-c] carbazolyl group, 1,3-dihydroindolo [3,2-c] carbazolyl group, 1,3-dihydroindeno [2,1-b] carbazolyl group , 5,11-dihydroindeno [1,2-b] carbazolyl group, 5,12-dihydroindeno [1,2-c] carbazolyl group, 5,8-dihydroindeno [2, 1-c] carbazolyl group, 7,12-dihydroindeno[1,2-a]carbazolyl group, 11,12-dihydroindeno[2,1-a]carbazolyl group, and the like. , but is not limited thereto.

In the present specification, the phosphine oxide group may be specifically substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes a diphenylphosphine oxide group, a dinaphthyl phosphine oxide group, and the like, but 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; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of 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 a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorine group There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, examples of the aryl group described above may be applied to the arylene group, except that the arylene group is a divalent group.

In the present specification, the heteroarylene group, except that the heteroarylene group is a divalent group, examples of the above-described heteroaryl group may be applied.

In an exemplary embodiment of the present specification, a compound represented by Formula 1 is provided.

In one embodiment of the present specification, the L and L' are each independently, a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In one embodiment of the present specification, the L and L' are each independently, a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

In one embodiment of the present specification, the L and L' are each independently, a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

In one embodiment of the present specification, the L and L' are each independently, a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

In one embodiment of the present specification, the L and L' are each independently, a direct bond; or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, the L and L' is a direct bond.

In one embodiment of the present specification, the L1 and L2 are each independently, a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In one embodiment of the present specification, the L1 and L2 are each independently, a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

In one embodiment of the present specification, the L1 and L2 are each independently, a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

In one embodiment of the present specification, the L1 and L2 are each independently, a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

In one embodiment of the present specification, the L1 and L2 are each independently, a direct bond; a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, the L1 and L2 are each independently, a direct bond; It is a phenylene group or a biphenylene group.

In an exemplary embodiment of the present specification, L1 is a direct bond, and L2 is a direct bond; It is a phenylene group or a biphenylene group.

In an exemplary embodiment of the present specification, Z, Ar1 and Ar2 are each independently a cyano group; halogen group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the following formula (A),

[Formula A]

In the formula A,

A ₁ and A ₂ are each independently, a substituted or unsubstituted C 1 to C 60 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,

R _a is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a 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,

r is an integer from 1 to 4,

When r is 2 or more, two or more R _a are the same as or different from each other.

In an exemplary embodiment of the present specification, Z is a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the above formula (A).

In an exemplary embodiment of the present specification, Z is a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Z is a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Z is a substituted or unsubstituted monocyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Z is a substituted or unsubstituted monocyclic aryl group having 6 to 10 carbon atoms.

In an exemplary embodiment of the present specification, Z is a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, Z is a phenyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the above formula (A).

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the above formula (A).

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the above formula (A).

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the above formula (A).

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a cyano group; halogen group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a cyano group; halogen group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group unsubstituted or substituted with one or more substituents selected from an alkyl group and an aryl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a cyano group; halogen group; phenyl group; biphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with one or more substituents selected from a methyl group and a phenyl group; a dibenzofuran group unsubstituted or substituted with a cyano group or a halogen group; a dibenzothiophene group unsubstituted or substituted with a cyano group or a halogen group; Or a carbazole group unsubstituted or substituted with a phenyl group.

In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a dibenzofuran group unsubstituted or substituted with a cyano group or a halogen group; or a dibenzothiophene group unsubstituted or substituted with a cyano group or a halogen group.

In an exemplary embodiment of the present specification, Ar1 is a dibenzofuran group unsubstituted or substituted with a cyano group or a halogen group; or a dibenzothiophene group unsubstituted or substituted with a cyano group or a halogen group, wherein Ar2 is a cyano group; halogen group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the above formula (A).

In an exemplary embodiment of the present specification, Ar1 is a dibenzofuran group unsubstituted or substituted with a cyano group or a halogen group; or a dibenzothiophene group unsubstituted or substituted with a cyano group or a halogen group, wherein Ar2 is a cyano group; halogen group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group unsubstituted or substituted with one or more substituents selected from an alkyl group and an aryl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 60 alkyl group; a 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 heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted 6 to 60 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

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

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

In the exemplary embodiment of the present specification, a, b, m and n are each an integer of 1 to 3, and when a, b, m and n are each 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present specification, a and b are 1.

In one embodiment of the present specification, m is 1 or 2.

In one embodiment of the present specification, n is 1 or 2.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-1.

[Formula 1-1]

In Formula 1-1, Z1 is a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, and definitions of the remaining substituents are the same as those in Formula 1.

In the exemplary embodiment of the present specification, Z1 is a substituted or unsubstituted monocyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Z1 is a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, Z1 is a phenyl group.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-2.

[Formula 1-2]

In Formula 1-2, the definition of each substituent is the same as the definition in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 1-3 below.

[Formula 1-3]

In Formula 1-3, the definition of each substituent is the same as the definition in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formulas 2 to 5 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, X is O or S, and definitions of the remaining substituents are the same as those in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structure of Formula 1, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

In one embodiment of the present specification, the first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes at least one compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, at least one of the organic material layers includes one kind of compound represented by Formula 1 above.

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

In another exemplary embodiment of the present specification, the first electrode may be a negative electrode, and the second electrode may be an anode.

In the exemplary embodiment of the present specification, the organic light emitting device may be a blue organic light emitting device, and the compound represented by Formula 1 may be used as a material of the blue organic light emitting device. For example, the compound represented by Formula 1 may be included in the hole transport layer or the electron blocking layer of the blue organic light emitting device.

In the exemplary embodiment of the present specification, the organic light emitting device may be a green organic light emitting device, and the compound represented by Formula 1 may be used as a material of the green organic light emitting device. For example, the compound represented by Formula 1 may be included in the hole transport layer or the electron blocking layer of the green organic light emitting diode.

In the exemplary embodiment of the present specification, the organic light emitting device may be a red organic light emitting device, and the compound represented by Formula 1 may be used as a material of the red organic light emitting device. For example, the compound represented by Formula 1 may be included in the hole transport layer or the electron blocking layer of the red organic light emitting device.

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

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

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention 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, etc. 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 material layers.

In the organic light emitting device of the present specification, the organic material layer may include a hole transport layer, and the hole transport layer may include the compound represented by Formula 1 above.

In the organic light emitting device of the present specification, the organic material layer may include an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 above.

The organic light emitting device of the present invention may further include one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

1 to 4 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present specification. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.

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

3 and 4 illustrate a case in which 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 304 , an electron transport layer 305 and an electron injection layer 306 , and the organic light emitting device according to FIG. 4 is and a hole injection layer 301 , a hole transport layer 302 , an electron blocking layer 303 , a light emitting layer 304 , an electron transport layer 305 , and an electron injection layer 306 . However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

The organic material layer including the compound represented by Formula 1 may further include other materials as needed.

In the organic light emitting device according to an exemplary embodiment of the present specification, materials other than the compound represented by Chemical Formula 1 are exemplified below, but these are for illustration only and not for limiting the scope of the present application. may be substituted with known materials.

Materials having a relatively large work function may be used as the anode material, and a transparent conductive oxide, metal, or conductive polymer may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO _{2 :Sb;} conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

Materials having a relatively low work function may be used as the cathode material, and metal, metal oxide, conductive polymer, or the like may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type amine derivatives such as tris(4-carbazolyl-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), soluble conductive polymers polyaniline/dodecylbenzenesulfonic acid (Polyaniline/Dodecylbenzenesulfonic acid) or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid (Polyaniline/Camphor sulfonic acid) or polyaniline/ poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrenesulfonate)) and the like can be used.

As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, and a low molecular weight or high molecular material may be used.

Examples of the electron transport material 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 derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.

As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

A red, green or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as separate sources, or may be premixed and deposited as a single source. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which the host material and the dopant material together participate in light emission may be used.

When mixing and using the host of the light emitting material, a host of the same series may be mixed and used, or a host of different series may be mixed and used. For example, any two or more types of n-type host material or p-type host material may be selected and used as the host material of the light emitting layer.

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

The compound according to an 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 photoreceptor, and an organic transistor.

Hereinafter, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

[Preparation Example 1] Preparation of compound A1-5

1) Preparation of compound A1-5-4

[1,1'-biphenyl]-2-ylboronic acid ([1,1'-biphenyl]-2-ylboronic acid) (50g, 0.25mol, 1.1eq), methyl 2-bromo-5-chlorobenzoate (methyl 2-bromo-5-chlorobenzoate) (57.3 g, 0.23 mol, 1.0eq), Pd(PPh ₃ ) ₄ (tetrakis(triphenylphosphine)palladium(0)) (14.4g, 0.0125 mol, 0.05eq) ), K ₃ PO ₄ (69.1 g, 0.50 mol, 2eq) was added to toluene (750 ml), H ₂ O and EtOH (150 ml) and stirred at 110° C. for 5 hours. After completion of the reaction by adding water, extraction was performed using methylene chloride (MC) and water. Thereafter, water was removed with anhydrous Na ₂ CO _{3 .} It was separated by a silica gel column to obtain 62 g of Compound A1-5-4 in a yield of 77%.

2) Preparation of compound A1-5-3

Compound A1-5-4 (50g, 0.15 mol, 1eq) was added to ether (600ml), followed by N ₂ substitution and stirred at 0°C. CH ₃ MgBr 3M in Ether (127ml, 0.38 mol, 2.5 eq) was slowly added dropwise, followed by stirring at RT (room temperature) for 12 hours. After completion of the reaction by adding water, extraction was performed using MC and water. Thereafter, water was removed with anhydrous Na ₂ CO _{3 .} After separation using a silica gel column, 42 g of Compound A1-5-3 was obtained in a yield of 88%.

3) Preparation of compound A1-5-2

Compound A1-5-3 (40g, 0.12 mol, 1eq) was added to dichloromethane (DCM) (600ml) and stirred at 0°C. Acetic acid (AcOH) (400ml) and hydrochloric acid (HCl) (40ml) were slowly added dropwise, followed by stirring at 140°C for 2 hours. After completion of the reaction by adding water, extraction was performed using MC and water. Thereafter, water was removed with anhydrous Na ₂ CO _{3 .} It was separated by a silica gel column to obtain 23 g of Compound A1-5-2 in a yield of 62%.

4) Preparation of compound A1-5-1

Compound A1-5-2 (10 g, 0.033 mol, 1eq), dibenzo [b, d] furan-4-amine (dibenzo [b, d] furan-4-amine) (A) (6.6 g, 0.036 mol, 1.1eq), Na t- BuO(Sodium tert-butoxide) (6.3g, 0.066 mol, 2eq), Pd ₂ (dba) ₃ (tris(dibenzylideneacetone)dipalladium(0)) (1.5g, 0.0017 mol , 0.05eq), t-Bu ₃ P (tri-tert-butylphosphine) (1.5ml 0.0033 mol, 0.1eq) was added to Toluene (100ml) and stirred at 110° C. for 6 hours. After completion of the reaction by adding water, extraction was performed using MC and water. Thereafter, water was removed with anhydrous Na ₂ CO _{3 .} It was separated by a silica gel column to obtain 10.5 g of Compound A1-5-1 in a yield of 71%.

5) Preparation of compound A1-5

Compound A1-5-1 (10 g, 0.022 mol, 1eq), 4-bromo-1,1'-biphenyl (4-bromo-1,1'-biphenyl) (B) (5.7 g, 0.024 mol, 1.1 eq), Na t- BuO (4.2 g, 0.044 mol, 2eq), Pd ₂ (dba) ₃ (1.0 g, 0.0011 mol, 0.05 eq), t- Bu ₃ P (1.0 ml 0.0022 mol, 0.1eq) Toluene ( 100ml) and stirred at 110°C for 6 hours. After completion of the reaction by adding water, extraction was performed using MC and water. Thereafter, water was removed with anhydrous Na ₂ CO _{3 .} It was separated by a silica gel column to obtain 10.6 g of Compound A1-5 in a yield of 80%.

Intermediate A of Table 1, 4-bromo-1,1' instead of dibenzo [b, d] furan-4-amine (A) in Preparation Example 1 -Biphenyl (4-bromo-1,1'-biphenyl) (B) was synthesized in the same manner by using the intermediate B of Table 1 instead of (B).

compound
number Intermediate A Intermediate B yield A1-5

80% A1-8

77% A1-21

69% A1-25

65% A1-29

72% A1-30

70% A1-36

71% A1-41

85% A2-5

85% A2-21

71% A2-29

78% B1-5

80% B1-21

76% B1-29

70% B1-41

72% B2-5

66% B2-21

65% B2-29

71% C1-5

77% C1-8

69% C1-21

65% C1-25

80% C1-29

85% C1-30

70% C1-41

82% C1-42

85% C2-5

67% C2-21

69% D1-5

65% D1-8

85% D1-21

77% D1-25

66% D1-29

74% D1-30

79% D1-41

78%

Compounds were prepared in the same manner as in Preparation Examples, and the synthesis confirmation results are shown in Tables 2 and 3. Table 2 is ^{a measurement value of 1} H NMR (CDCl ₃ , 200Mz), Table 3 is a measurement value of the FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

compound ¹ H NMR (CDCl ₃ , 200 Mz) A1-5 δ = 7.98 (1H, d), 7.79 to 7.75 (6H, m), 7.64 (2H, m), 7.55 to 7.28 (16H, m), 7.16 (1H, d), 6.97 (1H, d), 1.69 ( 6H, s) A1-8 δ = 7.98 (1H, d), 7.79 to 7.75 (6H, m), 7.64 (2H, m), 7.55 to 7.28 (20H, m), 7.16 (1H, d), 6.97 (1H, d), 1.69 ( 6H, s) A1-21 δ = 7.98 (1H, d), 7.79 to 7.75 (6H, m), 7.64 (2H, m), 7.55 to 7.28 (13H, m), 7.16 (2H, d), 6.97 (1H, d), 1.69 ( 12H, s) A1-36 δ = 8.09 (1H, d), 7.98 (1H, d), 7.79 to 7.75 (9H, m), 7.64 (2H, m), 7.55 to 7.28 (13H, m), 7.16 (2H, d), 6.97 ( 1H, d), 1.69 (12H, s) A1-29 δ = 7.98 (1H, d), 7.90 to 7.78 (6H, m), 7.64 (2H, m), 7.54 to 7.28 (24H, m), 6.97 (1H, d), 1.69 (6H, s) A1-30 δ = 7.98 (1H, d), 7.90 to 7.78 (8H, m), 7.64 (2H, m), 7.54 to 7.28 (19H, m), 7.16 (2H, d), 6.97 (1H, d), 1.69 ( 6H, s) A1-25 δ = 7.98 (2H, d), 7.86 to 7.79 (4H, m), 7.64 (3H, m), 7.54 to 7.28 (13H, m), 7.16 (1H, d), 6.97 (2H, d), 1.69 ( 6H, s) A1-41 δ = 8.08 to 7.98 (4H, s), 7.79 to 8 (4H, m), 7.65 (2H, m), 7.54 to 7.25 (17H, m), 7.16 (1H, d), 6.97 (1H, d), 1.69 (6H, s) A2-5 δ=8.03 to 7.98 (2H, d), 7.80 to 7.75 (7H, m), 7.64 (1H, m), 7.55 to 7.28 (15H, m), 7.16 (1H, d), 6.97 (1H, d), 1.69 (6H, s) A2-21 δ=8.03 to 7.98 (2H, d), 7.80 to 7.75 (7H, m), 7.64 (1H, m), 7.55 to 7.28 (12H, m), 7.16 (2H, d), 6.91 (1H, d), 1.69 (12H, s) A2-29 δ=8.03 to 7.98 (2H, d), 7.80 to 7.75 (7H, m), 7.64 (1H, m), 7.55 to 7.28 (22H, m), 7.16 (1H, d), 1.69 (6H, s) B1-5 δ = 8.45 (1H, d), 8.11 (1H, d), 7.93 (1H, d), 7.80 to 7.75 (6H, m), 7.64 (1H, m), 7.55 to 7.28 (16H, m), 7.16 ( 1H, d), 1.69 (6H, s) B1-21 δ = 8.45 (1H, d), 8.11 (1H, d), 7.86 to 7.78 (7H, m), 7.64 (1H, m), 7.55 to 7.28 (13H, m), 7.16 (2H, d), 1.69 ( 6H, s) B1-29 δ=8.45 (1H, d), 8.11 (1H, d), 7.93 to 7.78 (7H, m), 7.64 (1H, m), 7.55 to 7.28 (21H, m), 1.69 (6H, s) B1-41 δ=8.45 (1H, d), 8.11 to 7.93 (5H, m), 7.79 to 7.78 (4H, m), 7.55 to 7.28 (17H, m), 7.16 (1H, m), 1.69 (6H, s) B2-5 δ = 8.45 (1H, d), 8.01 (1H, d), 7.93 (1H, d), 7.79 to 7.78 (6H, m), 7.64 (2H, m), 7.55 to 7.28 (15H, m), 7.16 ( 1H, d), 1.69 (6H, s) B2-21 δ = 8.30 (7H, m), 7.92 (1H, d), 7.76 (5H, m), 7.54 to 7.41 (19H, m) 7.25 (2H, d), 1.69 (6H, s) B2-29 δ = 8.45 (1H, d), 8.01 (1H, d), 7.86 to 7.78 (7H, d), 7.64 (2H, m) 7.55 to 7.28 (12H, m), 7.16 (2H, d), 1.69 (6H) , s) C1-5 δ = 8.08 to 7.98 (3H, m), 7.79 to 7.75 (6H, m), 7.65 (1H, d) 7.55 to 7.28 (20H, m), 7.16 (1H, d), 1.69 (6H, s) C1-8 δ = 8.08 to 7.98 (3H, m), 7.79 to 7.75 (6H, m), 7.65 (1H, d) 7.55 to 7.28 (24H, m), 7.16 (1H, d), 1.69 (6H, s) C1-21 δ = 8.08 to 7.98 (3H, m), 7.79 to 7.75 (6H, m), 7.65 (1H, d) 7.55 to 7.28 (17H, m), 7.16 (2H, d), 1.69 (12H, s) C1-25 δ = 8.08 to 7.98 (4H, m), 7.79 to 7.75 (4H, m), 7.65 (2H, d) 7.55 to 7.16 (17H, m), 7.16 (1H, d), 6.97 (1H, d), 1.69 (6H, s) C1-29 δ=8.08 to 7.98 (3H, m), 7.79 to 7.75 (6H, m), 7.65 (1H, d) 7.55 to 7.16 (28H, m), 1.69 (6H, s) C1-30 δ = 8.08 to 7.98 (3H, m), 7.79 to 7.75 (6H, m), 7.65 (1H, d) 7.55 to 7.16 (23H, m), 7.16 (2H, d), 1.69 (6H, s) C1-41 δ = 8.08 to 7.98 (6H, m), 7.79 to 7.75 (4H, m), 7.65 (1H, d) 7.55 to 7.16 (21H, m), 7.16 (1H, d), 1.69 (6H, s) C1-42 δ = 8.08 to 7.98 (6H, m), 7.79 to 7.75 (4H, m), 7.65 (1H, d) 7.55 to 7.16 (21H, m), 7.16 (1H, d), 1.69 (6H, s) C2-5 δ = 8.03 to 7.98 (2H, m), 7.79 to 7.75 (8H, m), 7.65 (1H, d) 7.55 to 7.16 (19H, m), 7.16 (1H, d), 1.69 (6H, s) C2-21 δ = 8.03 to 7.98 (2H, m), 7.79 to 7.75 (8H, m), 7.65 (1H, d) 7.55 to 7.16 (16H, m), 7.16 (2H, d), 1.69 (12H, s) D1-5 δ = 8.55 (1H, d), 8.45 (1H, d), 8.32 (1H, d), 7.93 to 7.65 (9H, m), 7.55 to 7.28 (18H, m), 7.16 (1H, d), 1.69 ( 6H, s) D1-8 δ = 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 7.93-7.65(9H, m), 7.55-7.28 (22H, m), 7.16(1H, d), 1.69( 6H, s) D1-21 δ = 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 7.93-7.65(9H, m), 7.55-7.28 (22H, m), 7.16(1H, d), 1.69( 12H, s) D1-29 δ = 8.45 (1H, d), 8.24 to 8.12 (3H, d), 7.93 to 7.78 (6H, m), 7.65 (1H, d), 7.55 to 7.16 (28H, m), 1.69 (6H, s) D1-30 δ = 8.45 (1H, d), 8.24 to 8.12 (3H, d), 7.93 to 7.78 (8H, m), 7.65 (1H, d), 7.55 to 7.28 (22H, m), 7.16 (1H, d), 7.06 (1H, d), 1.69 (6H, s) D1-25 δ = 8.55 (1H, d), 8.45 (1H, d), 8.32 (1H, d), 8.08 to 7.65 (10H, m), 7.55 to 7.28 (19H, m), 7.16 (1H, d), 6.97 ( 1H, d), 1.69 (6H, s) D1-41 δ = 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 7.98-7.16(20H, m), 7.55-7.28 (19H, m), 7.16(1H, d), 1.69( 12H, s)

compound FD-MS compound FD-MS A1-5 m/z = 603.76 (C45H33NO =603.76) C1-5 m/z = 679.86
(C51H37NO=679.86) A1-8 m/z = 679.86 (C51H37NO =679.86) C1-8 m/z = 755.96
(C57H41NO=755.96) A1-21 m/z = 643.83 (C48H37NO =643.83) C1-21 m/z= 719.93 (C54H41NO=719.93) A1-36 m/z = 633.81 (C45H31NOS =633.81) C1-29 m/z = 695.92
(C51H37NS=695.92) A1-29 m/z = 767.97 (C58H41NO =767.97) C1-30 m/z = 695.92
(C51H37NS=695.92) A1-30 m/z = 765.96 (C58H39NO =765.96) C1-25 m/z = 695.92
(C51H37NS=695.92) A1-25 m/z = 617.75 (C45H31NO2 =617.75) C1-41 m/z = 709.91
(C51H35NOS =709.91) A1-41 m/z = 693.85 (C51H35NO2 =693.85) C1-42 m/z = 709.91
(C51H35NOS =709.91) A2-5 m/z = 603.76 (C45H33NO =603.76) C2-5 m/z = 679.86
(C51H37NO=679.86) A2-21 m/z = 643.83 (C48H37NO =643.83) C2-21 m/z = 719.93
(C54H41NO=719.93) A2-29 m/z = 767.97 (C58H41NO =767.97) D1-5 m/z = 695.92
(C51H37NS=695.92) B1-5 m/z = 619.83 (C45H33NS =619.83) D1-8 m/z= 772.02
(C57H41NS =772.02) B1-21 m/z = 659.89 (C48H37NS = 659.89) D1-21 m/z = 735.99
(C54H41NS =735.99) B1-29 m/z= 784.03 (C58H41NS= 784.03) D1-29 m/z = 860.13
(C64H45NS = 860.13) B1-41 m/z = 709.91 (C51H35NOS = 709.91) D1-30 m/z = 858.12
(C64H43NS = 858.12) B2-5 m/z = 619.83 (C45H33NS =619.83) D1-25 m/z = 709.91
(C51H35NOS =709.91) B2-21 m/z = 659.89 (C48H37NS = 659.89) D1-41 m/z= 786.00
(C57H39NOS =786.00) B2-29 m/z = 784.03 (C58H41NS = 784.03)

[Experimental example]

<Experimental Example 1>

1) Fabrication of an organic light emitting device

-Comparative Example 1

The transparent electrode ITO (Indium Tin Oxide) thin film obtained from glass for OLED (manufactured by Samsung-Corning) was ultrasonically washed for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then placed in isopropanol and stored. was used. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.

Then, after evacuating the chamber ^{until the vacuum degree reached 10 -6} torr, an electric current was applied to the cell to evaporate 2-TNATA, and a 600 Å-thick hole injection layer was deposited on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis(α-naphthyl)-N, N'-diphenyl-4,4'-diamine: NPB) was added, and a current was applied to the cell to evaporate and deposit a hole transport layer with a thickness of 300 Å on the hole injection layer.

After the hole injection layer and the hole transport layer were formed in this way, a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 Å in one cell in the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% compared to the host material thereon.

Subsequently, a compound of the following structural formula E1 was deposited as an electron transport layer to a thickness of 300 Å.

As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 Å, and an Al cathode was deposited to a thickness of 1,000 Å to fabricate an OLED device. On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under ^{10 -8} to 10 ^{-6 torr for each material and used for OLED manufacturing.}

- Examples 1 to 35 and Comparative Examples 2 to 4

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 4 was used instead of the NPB used in forming the hole transport layer in Comparative Example 1.

2) Evaluation of organic light emitting devices

The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 700 cd/ When m ² , T ₉₅ was measured. Table 4 shows the results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the blue organic light emitting diode manufactured according to the present invention.

compound drive voltage
(V) Luminous Efficiency
(cd/A) life span
(T ₉₅ ) Example 1 A1-5 4.99 6.12 58 Example 2 A1-8 4.89 6.23 67 Example 3 A1-21 4.77 6.30 59 Example 4 A1-36 4.72 6.98 56 Example 5 A1-29 4.80 6.89 67 Example 6 A1-30 4.75 6.95 60 Example 7 A1-25 4.68 6.93 55 Example 8 A1-41 4.87 6.84 63 Example 9 A2-5 4.75 6.91 56 Example 10 A2-21 4.98 6.35 59 Example 11 A2-29 4.11 6.12 64 Example 12 B1-5 4.96 6.17 72 Example 13 B1-21 4.17 6.20 75 Example 14 B1-29 4.65 6.43 68 Example 15 B1-41 4.82 6.84 57 Example 16 B2-5 4.84 6.97 56 Example 17 B2-21 4.90 6.81 61 Example 18 B2-29 4.88 6.82 62 Example 19 C1-5 4.74 6.75 56 Example 20 C1-8 4.81 6.82 58 Example 21 C1-21 4.26 6.44 66 Example 22 C1-29 4.99 6.38 58 Example 23 C1-30 4.16 6.20 59 Example 24 C1-25 4.95 6.42 54 Example 25 C1-41 4.31 6,30 55 Example 26 C1-42 4.33 6.22 62 Example 27 C2-5 4.32 5.95 69 Example 28 C2-21 4.82 6.35 59 Example 29 D1-5 4.84 6.60 61 Example 30 D1-8 4.94 6.68 52 Example 31 D1-21 4.96 6.70 61 Example 32 D1-29 4.91 6.69 51 Example 33 D1-30 4.90 6.71 55 Example 34 D1-25 4.57 6.16 64 Example 35 D1-41 4.56 6.22 59 Comparative Example 1 NPB 5.10 5.99 50 Comparative Example 2 HTL 1 5.00 6.01 50 Comparative Example 3 HTL 2 5.01 5.97 45 Comparative Example 4 HTL 3 5.05 5.94 47

As can be seen from the results of Table 4, the organic light emitting device using the hole transport layer material of the blue organic light emitting device of the present invention has a lower driving voltage and lower luminous efficiency and lifetime than Comparative Examples 1, 2 and 3 significantly improved.

Comparing Comparative Example 1 and the compound of the present invention, although having an arylamine group is similar, the compound of the present invention has a difference from the compound of Comparative Example 1 in which a fluorene group is substituted with a dibenzofuran or dibenzothiophene group. have. In the case of a fluorene group with a substituent, it suppresses pi-pi stacking of the aromatic ring, thereby increasing the driving voltage of the organic light emitting diode, thereby preventing deterioration of device characteristics. In particular, it is judged that the compounds of fluorene, dibenzofuran or dibenzothiophene amine derivatives have improved hole transport properties or stability to provide superiority in all aspects of driving, efficiency, and lifespan.

The compound of Comparative Example 2 has a fluorene group and a dibenzofuran group as an arylamine group, which is similar to the present invention, but the compound of Comparative Example 2 does not have a substituent on the benzene ring of the fluorene group. In the case of the compound of the present invention, since a bulky phenyl group is introduced at the 4th position of the fluorene group, steric hindrance occurs, and this increases the T1 value. . In addition, by connecting the phenyl group to the fluorene group, the HOMO electron cloud is expanded, thereby increasing the HOMO energy level, thereby further strengthening the hole injection and hole transport capability, thereby lowering the driving voltage of the device to which the HOMO electron cloud is applied.

Comparing Comparative Example 3 and the compound of the present invention, having a fluorene group and a dibenzofuran group as an arylamine group is similar, but there is a difference in that another substituent of Comparative Example 3 is a spirofluorene group. On the other hand, since the compound of the present invention does not form a ring, the phenyl group having a π-bond suppresses π-π stacking between adjacent molecules, thereby increasing the driving voltage of the organic light emitting device, resulting in improved device characteristics. It can be confirmed that it prevents deterioration, has excellent driving and efficiency characteristics, and particularly has excellent lifespan characteristics. In addition, since the three-dimensional size increases and intermolecular interactions decrease, crystallization of the material is suppressed, and thus the stability of the thin film is improved.

Comparing Comparative Example 4 with the compound of the present invention, having a fluorene group and a dibenzofuran group as an arylamine group is similar, but the phenyl group substituted with the fluorene group of Comparative Example 4 and the phenyl group substitution position of the compound of the present invention are different Do. When the phenyl group of the present compound is substituted at the 4th position based on the amine and the phenyl group is substituted at the 4th position rather than the 2nd position than in Comparative Example 4, the hole mobility is high, and the HOMO of the present compound substituted at the 4th position The electron cloud distribution of phenyl is distributed to phenyl, so that the compound of the present invention has an appropriate energy level, which increases the charge balance in the light emitting layer of holes and electrons, indicating excellent results in driving voltage and efficiency life. do.

<Experimental Example 2>

1) Fabrication of an organic light emitting device

-Comparative Example 5

The transparent electrode ITO thin film obtained from glass for OLED (manufactured by Samsung-Corning) was ultrasonically washed for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then placed in isopropanol and stored before use. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.

Then, after evacuating the chamber ^{until the vacuum degree reached 10 -6} torr, an electric current was applied to the cell to evaporate 2-TNATA, and a 600 Å-thick hole injection layer was deposited on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis(α-naphthyl)-N, N'-diphenyl-4,4'-diamine: NPB) was added, and a current was applied to the cell to evaporate and deposit a hole transport layer with a thickness of 300 Å on the hole injection layer.

After the hole injection layer and the hole transport layer were formed in this way, a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 Å in one cell in the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% compared to the host material thereon.

Subsequently, a compound of the following structural formula E1 was deposited as an electron transport layer to a thickness of 300 Å.

As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 Å, and an Al cathode was deposited to a thickness of 1,000 Å to fabricate an OLED device. On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under ^{10 -8} to 10 ^{-6 torr for each material and used for OLED manufacturing.}

- Examples 36 to 70 and Comparative Examples 5 to 8

In Comparative Example 5, the thickness of the hole transport layer NPB was formed to be 250 Å, and then the electron blocking layer was formed to a thickness of 50 Å of the compound shown in Table 5 on the hole transport layer. to fabricate an organic electroluminescent device.

2) Evaluation of organic light emitting devices

Table 5 shows the results of measuring the driving voltage, luminous efficiency, and lifespan of the blue organic light emitting diode manufactured according to the present invention.

compound drive voltage
(V) Luminous Efficiency
(cd/A) life span
(T ₉₅ ) Example 36 A1-5 4.99 6.11 60 Example 37 A1-8 4.96 6.13 65 Example 38 A1-21 4.97 6.23 63 Example 39 A1-36 4.82 5.98 59 Example 40 A1-29 4.77 6.08 66 Example 41 A1-30 5.03 5.95 61 Example 42 A1-25 4.76 6.01 57 Example 43 A1-41 4.97 5.84 65 Example 44 A2-5 4.75 6.41 55 Example 45 A2-21 4.98 6.35 60 Example 46 A2-29 4.77 6.12 59 Example 47 B1-5 4.96 6.10 71 Example 48 B1-21 5.01 6.20 64 Example 49 B1-29 5.04 6.44 62 Example 50 B1-41 4.92 6.14 59 Example 51 B2-5 4.88 6.56 57 Example 52 B2-21 4.94 6.66 61 Example 53 B2-29 4.78 5.97 63 Example 54 C1-5 4.77 6.78 57 Example 55 C1-8 4.81 6.82 55 Example 56 C1-21 5.08 6.44 59 Example 57 C1-29 4.99 6.28 54 Example 58 C1-30 4.88 6.20 61 Example 59 C1-25 4.95 6.42 63 Example 60 C1-41 4.77 6,33 60 Example 61 C1-42 4.68 6.28 55 Example 62 C2-5 4.56 5.95 56 Example 63 C2-21 4.11 6.35 59 Example 64 D1-5 4.15 6.60 52 Example 65 D1-8 4.94 6.68 61 Example 66 D1-21 4.96 6.70 51 Example 67 D1-29 4.92 6.69 55 Example 68 D1-30 4.93 6.71 63 Example 69 D1-25 5.07 6.12 51 Example 70 D1-41 5.21 6.22 59 Comparative Example 5 NPB 5.50 5.33 45 Comparative Example 6 HTL1 5.47 5.55 49 Comparative Example 7 HTL2 5.49 5.54 48 Comparative Example 8 HTL3 5.44 5.60 47

As can be seen from the results of Table 5, the organic light emitting device using the electron blocking layer material of the blue organic light emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 5 to 8.

In the case of the former, if it passes through the hole transport layer to the anode without being combined in the light emitting layer, the efficiency and lifespan of the OLED device are reduced. When a compound having a high LUMO level is used as the electron blocking layer to prevent this phenomenon, electrons passing through the light emitting layer to the anode are blocked by the energy barrier of the electron blocking layer.

Therefore, the probability that holes and electrons form excitons increases and the possibility of emission as light from the light emitting layer increases, so that the compound of the present invention is driven due to a higher LUMO Level than the compounds of Comparative Examples 5, 6 and 7 and 8 It is judged that it brought excellence in all aspects of , efficiency, and lifespan.

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

Claims (11)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
R1 and R2 are each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 60 alkyl group; a 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,
L, L', L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,
a, b, m and n are each an integer from 1 to 3,
When a, b, m and n are each 2 or more, the substituents in parentheses are the same as or different from each other,
Z, Ar1 and Ar2 are each independently a cyano group; halogen group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or represented by the following formula (A),
[Formula A]

In the formula A,
A ₁ and A ₂ are each independently, a substituted or unsubstituted C 1 to C 60 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,
R _a is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a 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,
r is an integer from 1 to 4,
When r is 2 or more, two or more R _a are the same as or different from each other. The method according to claim 1,
The compound of Formula 1 is represented by the following Formula 1-1:
[Formula 1-1]

In Formula 1-1,
Z1 is a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms,
Definitions of the remaining substituents are the same as those in Formula 1. The method according to claim 1,
The compound of Formula 1 is represented by the following Formula 1-2:
[Formula 1-2]

In Formula 1-2,
The definition of each substituent is the same as the definition in Formula 1. The method according to claim 1,
At least one of Ar1 and Ar2 is a substituted or unsubstituted dibenzofuran group or a substituted or unsubstituted dibenzothiophene group. The method according to claim 1,
Wherein Ar1 is a substituted or unsubstituted dibenzofuran group or a substituted or unsubstituted dibenzothiophene group,
Wherein Ar2 is a cyano group; halogen group; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; Or a substituted or unsubstituted monocyclic or bicyclic aryl group having 6 to 20 carbon atoms, or a compound represented by Formula A. The method according to claim 1,
L1 is a direct bond; Or a compound that is a phenylene group. The method according to claim 1,
The compound of Formula 1 is represented by any one of the following compounds:

. a first electrode; a second electrode; and an organic material layer provided between the first electrode and the second electrode,
The organic material layer is an organic light emitting device comprising at least one compound according to any one of claims 1 to 7. 9. The method of claim 8,
The organic layer includes a hole transport layer,
The hole transport layer is an organic light emitting device comprising the compound of Formula 1. 9. The method of claim 8,
The organic layer includes an electron blocking layer,
The electron blocking layer is an organic light emitting device comprising the compound of Formula 1. 9. The method of claim 8,
The organic light emitting device further comprises one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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