WO2018174678A1 - Heterocyclic compound and organic light emitting element comprising same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting element comprising the same.

Description

Heterocyclic compound and organic light emitting device comprising the same

This application is for the benefit date of Korean Patent Application No. 10-2017-0037979 filed to the Korean Intellectual Property Office on March 24, 2017 and Korean Patent Application No. 10-2018-0018782 filed to the Korean Patent Office on February 14, 2018. Claim, all of which are hereby incorporated by reference.

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

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

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

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound that may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like may be used.

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

Compounds having a chemical structure capable of satisfying the conditions required for materials usable in the organic light emitting device, such as appropriate energy level, electrochemical stability and thermal stability, and can play various roles required in the organic light emitting device according to substituents. There is a need for a study on an organic light emitting device comprising a.

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

[Formula 1]

In Chemical Formula 1,

N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,

L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, a is an integer of 1 to 3, when a is 2 or more, L is the same as or different from each other,

R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, b and c each represent an integer of 1 to 3 R9 is the same as or different from each other when b is 2 or more, and R10 is the same as or different from each other when c is 2 or more.

In addition, according to an exemplary embodiment of the present application, the first electrode; A second electrode provided to face the first 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 a heterocyclic compound represented by Chemical Formula 1. To provide.

The compound described in this specification can be used as an organic material layer material of an organic light emitting element. 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 in the organic light emitting device. In particular, the compound can be used as the light emitting layer material of the organic light emitting device. For example, the compound may be used alone as a light emitting material, or may be used as a host material of the light emitting layer.

In particular, in Formula 1, the N-containing ring is substituted at the carbon position of the dibenzofuran structure, and the carbazole structure is substituted for the benzene in which the N-containing ring is not substituted in the structure of the dibenzofuran structure, thereby providing a more electron stable structure. It is possible to improve the device life.

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

100: substrate

200: anode

300: organic material 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

Hereinafter, the present application will be described in detail.

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

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. Carbon number of 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, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 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 another substituent. Carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples thereof 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, and 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 and the like, 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 another substituent. 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 alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means 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 another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. 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 means 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 another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like. Carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, 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, the 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 another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The aryl group includes a spiro group. 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 phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyre Neyl group, tetrasenyl group, pentaxenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof Etc., but is not limited thereto.

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

When the fluorenyl group is substituted,

,

,

,

,

,

Etc., but is not limited thereto.

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 means 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 another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. Carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl and thiazolyl Group, isothiazolyl group, triazolyl group, furazanyl group, oxdiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxyyl group, triazinyl group, tetragenyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthrididi Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triaza indene group, indolyl group, indolinyl 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-dihydro Acridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthyridinyl group, phenanthrolinyl group, benzo [c] [1,2,5] thiadiazolyl group, 5,10-di Hydrodibenzo [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, 5,11-dihydroindeno [1,2-b] carbazolyl group, and the like, but are not limited thereto.

In the present specification, the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH ₂ ; Dialkylamine groups; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkyl heteroaryl amine group; And it may be selected from the group consisting of arylheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluore And a phenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.

In the present specification, an arylene group means one having two bonding positions, that is, a divalent group. The description of the aforementioned aryl group can be applied except that they are each divalent. In addition, a heteroarylene group means having two bond positions, ie, a divalent group, in a heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

In the present specification, the phosphine oxide group may be specifically substituted with an aryl group, and the aryl group described above may be applied. For example, the phosphine oxide group may include a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent” groups.

The structures exemplified as the cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group described above can be applied except that the aliphatic or aromatic hydrocarbon ring or heterocycle that the adjacent groups can form is not monovalent.

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

In one embodiment of the present application, Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 5.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5, the substituents are as defined in Chemical Formula 1.

In one embodiment of the present application, N-Het is a monocyclic or polycyclic heterocycle substituted or unsubstituted and containing one or more N.

In another exemplary embodiment, N-Het is a monocyclic or polycyclic heterocycle substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group, and containing one or more N.

In another exemplary embodiment, N-Het is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorene group, a dibenzofuran group and a dibenzothiophene group, It is a monocyclic or polycyclic heterocycle containing one or more N.

In another exemplary embodiment, N-Het is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorene group, a dibenzofuran group and a dibenzothiophene group, It is a monocyclic or polycyclic heterocycle containing 1 or more than 3 N.

In one embodiment of the present application, N-Het is a monocyclic hetero ring which is substituted or unsubstituted and includes one or more N.

In one embodiment of the present application, N-Het is a substituted or unsubstituted, bicyclic or more heterocyclic ring containing one or more N.

In one embodiment of the present application, N-Het is a monocyclic or polycyclic heterocycle substituted or unsubstituted and containing two or more N.

In one embodiment of the present application, N-Het is a bicyclic or higher polycyclic heterocycle including two or more N's.

In one embodiment of the present application, Chemical Formula 1 is represented by one of the following Chemical Formulas 6 to 8.

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 6 to 8,

Definitions of R1 to R10, L, a, b and c are the same as the definition in Formula 1,

X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N,

R11 to R15 and R17 to R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.

In one embodiment of the present application,

May be represented by one of the following Chemical Formulas 9 to 12. here,

Is the site linked to L.

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formula 9, at least one of X1, X3 and X5 is N, and the others are as defined in Formula 6,

In Formula 10, at least one of X1, X2 and X5 is N, and the others are as defined in Formula 6,

In Formula 11, at least one of X 1 to X 3 is N, and the others are as defined in Formula 6,

In Formula 12, at least one of X1, X2 and X5 is N, and the others are as defined in Formula 6,

R12, R14 and R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.

In one embodiment of the present application, Chemical Formula 9 may be selected from the following structural formulas.

In one embodiment of the present application, Chemical Formula 10 may be represented by the following Chemical Formula 13.

[Formula 13]

Substituents of Formula 13 are the same as defined in Formula 10.

In one embodiment of the present application, Chemical Formula 11 may be represented by the following Chemical Formula 14.

[Formula 14]

Substituents of Chemical Formula 14 are as defined in Chemical Formula 11.

In one embodiment of the present application, Chemical Formula 10 may be represented by the following Chemical Formula 15.

[Formula 15]

In Formula 15, R27 is the same as or different from each other, and hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And at least two groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, e is an integer from 0 to 7 and e is When two or more, R27 is same or different from each other.

In one embodiment of the present application, Chemical Formula 12 may be represented by the following Chemical Formula 16.

[Formula 16]

Substituents of Formula 16 are as defined in Formula 12.

In another exemplary embodiment, L is a direct bond or an arylene group.

In another exemplary embodiment, L is a direct bond or a phenylene group.

In another exemplary embodiment, R9 and R10 are hydrogen; Or deuterium.

In another exemplary embodiment, R9 and R10 are hydrogen.

In another exemplary embodiment, R1 to R8 are hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with an alkyl group, an aryl group or a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.

In another exemplary embodiment, R1 to R8 are hydrogen; heavy hydrogen; Aryl group; Heteroaryl group; Or a heteroaryl group substituted with an aryl group.

In another exemplary embodiment, R1 to R8 are hydrogen; heavy hydrogen; Phenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups; Or a carbazole group substituted with phenyl.

In another exemplary embodiment, R1 to R8 are hydrogen; heavy hydrogen; Phenyl group; Dibenzofuran group; Or a carbazole group substituted with phenyl.

In another exemplary embodiment, two adjacent substituents of R1 to R8 combine with each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, two adjacent substituents of R1 to R8 combine with each other to form a ring unsubstituted or substituted with an aryl group or an alkyl group.

In another exemplary embodiment, two adjacent substituents of R1 to R8 combine with each other to form an aromatic hydrocarbon ring or a heterocyclic ring which is unsubstituted or substituted with an aryl group or an alkyl group.

In another exemplary embodiment, two adjacent substituents of R1 to R8 combine with each other to form an aromatic hydrocarbon ring or a heterocyclic ring which is unsubstituted or substituted with a phenyl group or a methyl group.

In another exemplary embodiment, two adjacent substituents of R1 to R8 are bonded to each other to form a benzene ring; Indole substituted or unsubstituted with a phenyl group; Benzothiophene ring; Benzofuran ring; Or a substituted or unsubstituted indene ring with a methyl group.

In another embodiment,

Can be represented by the following formula (17). here,

Is a site linked to the dibenzofuran structure.

[Formula 17]

In Chemical Formula 17,

R1 to R4 are the same as defined in Formula 1,

Y is O, S, NR or CR'R ",

R, R ', R ", R31 and R32 are the same as or different from each other, hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted Or an unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted phosphine oxide group And two or more groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, f is an integer of 0 to 4 and f Is 31 or more, R31 is the same as or different from each other, g is an integer of 0 to 2, and if g is 2 or more, R32 is the same or different from each other.

In another exemplary embodiment, Chemical Formula 17 may be selected from the following structural formulas.

In another exemplary embodiment, R18 to R21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.

In another exemplary embodiment, R18 to R21 are the same as or different from each other, and each independently hydrogen; Or deuterium.

In yet one embodiment, R18 to R21 is hydrogen.

In another exemplary embodiment, R17 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.

In another exemplary embodiment, R17 and R22 are the same as or different from each other, and each independently an aryl group; Or a heteroaryl group.

In another exemplary embodiment, R17 and R22 are the same as or different from each other, and are each independently an aryl group.

In another exemplary embodiment, R17 and R22 are phenyl groups.

In another exemplary embodiment, R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with an alkyl group; Or a substituted or unsubstituted heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with an alkyl group; Or a heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with a methyl group; Or a heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenylyl group; Naphthyl group; Dimethyl fluorenyl group; Dibenzofuran group; Or a dibenzothiophene group.

In another exemplary embodiment, R12 and R14 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group; Or a heteroaryl group.

In yet one embodiment, R12 and R14 are the same as or different from each other, and each independently a phenyl group, a biphenylyl group, a naphthyl group, a dimethylfluorenyl group; Dibenzofuran group; Or a dibenzothiophene group.

In another exemplary embodiment, R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.

In another exemplary embodiment, R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group.

In another exemplary embodiment, R23 to R26 are the same as or different from each other, and each independently hydrogen; Or an aryl group.

In another exemplary embodiment, R23 to R26 are the same as or different from each other, and each independently hydrogen; Phenyl group; Or a biphenylyl group.

In another embodiment, R27 is hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.

In another exemplary embodiment, R27 is hydrogen; heavy hydrogen; Or an aryl group.

In another exemplary embodiment, R27 is hydrogen; Or an aryl group.

In another exemplary embodiment, R27 is hydrogen; Or a phenyl group.

In another embodiment, Y is O or S.

In another exemplary embodiment, Y is NR and R is an aryl group.

In another exemplary embodiment, Y is NR and R is a phenyl group.

In another exemplary embodiment, Y is CR'R ", and R 'and R" are alkyl groups.

In another exemplary embodiment, Y is CR'R ", and R 'and R" are methyl groups.

In another exemplary embodiment R31 is hydrogen; heavy hydrogen; Aryl group; Or a heteroaryl group.

In another exemplary embodiment R31 is hydrogen; heavy hydrogen; Or an aryl group.

In another exemplary embodiment R31 is hydrogen; Or a phenyl group.

In another exemplary embodiment, R32 is hydrogen; Or deuterium.

In another exemplary embodiment, R32 is hydrogen.

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.

In addition, by introducing various substituents into the structure of the formula (1) it is possible to synthesize a compound having the intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used in the hole injection layer material, the hole transporting material, the light emitting layer material, the electron transporting material and the charge generating layer material used in the manufacture of the organic light emitting device to meet the requirements required for each organic material layer The substance to make can be synthesize | combined.

In addition, by introducing a variety of substituents in the structure of the formula (1) it is possible to finely control the energy bandgap, on the other hand to improve the characteristics at the interface between the organic material and to vary the use of the material.

In addition, in an exemplary embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound according to Chemical Formula 1. to provide.

Details of the heterocyclic compound represented by Formula 1 are the same as described above.

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

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

In an exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the blue organic light emitting device.

In an exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the green organic light emitting device.

In an exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the red organic light emitting device.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound described above.

The heterocyclic compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer 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 and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include a light emitting layer, the light emitting layer may include a host material, and the host material may include the heterocyclic compound.

As another example, the organic material layer including the heterocyclic compound may include the heterocyclic compound represented by Chemical Formula 1 as a host, and may be used together with an iridium-based dopant.

In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

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

1 to 3 illustrate a lamination order of an electrode and an organic material layer of an organic light emitting diode according to an exemplary embodiment of the present application. However, these drawings are not intended to limit the scope of the present application, the structure of the organic light emitting device known in the art can 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, the present invention is not limited thereto, and as illustrated 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 illustrates a case where the organic material layer is a multilayer. 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 such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.

The organic material layer including the compound of Formula 1 may further include other materials as necessary.

In the organic light emitting device according to the exemplary embodiment of the present application, materials other than the compound of Chemical Formula 1 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, and are known in the art. Material may be replaced.

As the anode material, materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used. Specific examples of the positive electrode 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), indium zinc oxide (IZO); A combination of a metal and an oxide 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, and the like, but are not limited thereto.

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

As the hole injection material, a well-known hole injection material 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 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, or poly (line) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), polyaniline / Camphor sulfonic acid or polyaniline / Poly (4-styrenesulfonate) (Polyaniline / Poly (4-styrene-sulfonate)) etc. can be used.

As the hole transporting material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.

Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthhraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.

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

As the light emitting material, a red, green or blue light emitting material may be used, and if necessary, two or more light emitting materials may be mixed. In this case, two or more light emitting materials may be deposited and used as separate sources, or premixed and deposited as one 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 which combines holes and electrons injected from the anode and the cathode, respectively, to emit light may be used, but materials in which both the host material and the dopant material are involved in light emission may be used.

In the case of mixing and using a host of luminescent materials, a host of the same series may be mixed, or a host of another series may be mixed. For example, any two or more kinds of materials of n-type host material or P-type host material can 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 application may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.

The heterocyclic compound according to the exemplary embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.

Hereinafter, the present specification will be described in more detail with reference to Examples, but these are merely to illustrate the present application and are not intended to limit the scope of the present application.

Preparation of Compound 1-1

In a round bottom flask (One neck rbf), 1-bromo-2,3-difluorobenzene (40.5 g, 209 mmol), (2-chloro-6-methoxyphenyl) boronic acid (43 g, 230 mmol) , Tetrakis (triphenylphosphine) palladium (0) (24 g, 20.9 mmol), potassium carbonate (57.9 g, 419 mmol), toluene / ethanol / water (500 ml / 100 ml / 100 ml) mixture was refluxed at 110 ° C. Extracted with dichloromethane and dried over MgSO ₄ . The silica gel filter was then concentrated to give compound 1-1. (40.8g, 76%)

Preparation of Compound 1-2

In a round bottom flask (One neck rbf) of 2'-chloro-2,3-difluoro-6'-methoxy-1,1'-biphenyl (40.8 g, 160 mmol), MC (600 ml) The mixture was cooled to 0 ° C., BBr ₃ (30 mL, 320 mmol) was added dropwise, and the temperature was raised to room temperature, followed by stirring for 1 hour. The reaction was terminated with distilled water and extracted with dichloromethane and dried over MgSO ₄ . Column purification MC: HX = 1: 1 to give the compound 1-2. (21 g, 54%)

Preparation of Compound 1-3

In a single round bottom flask (One neck rbf) 4-chloro-2 ', 3'-difluoro- [1,1'-biphenyl] -2-ol (21 g, 87.2 mmol), Cs ₂ CO ₃ ( 71 g, 218 mmol) of dimethylacetamide (200 ml) mixture was stirred at 120 ° C. After cooling, the mixture was filtered, the solvent was removed from the filtrate, and the column was purified to HX: MC = 4: 1, to obtain Compound 1-3. (17g, 88%)

Preparation of Compound 1-4

In a round bottom flask (One neck rbf) 1-chloro-6-fluorodibenzo [b, d] furan (6g, 27.19 mmol), 9H-carbazole (5g, 29.9mmol), Cs ₂ CO ₃ (22g , 101.7 mmol), and a mixture of dimethylacetamide (60 ml) were refluxed at 170 ° C. for 12 h. After cooling, the mixture was filtered, the solvent was removed from the filtrate, and the column was purified to HX: MC = 3: 1 to obtain Compound 1-4. (9g, 90%)

Preparation of Compound 1-5

In a round bottom flask (One neck rbf) 9- (9-chlorodibenzo [b, d] furan-4-yl) -9H-carbazole (9 g, 24.4 mmol), bis (pinacolato) diboron 1,4-dioxane (100 ml) mixture of (12.4 g, 48.9 mmol), Pcy3 (1.37 g, 4.89 mmol), potassium acetate (7.1 g, 73 mmol), Pd2 (dba) 3 (2.2 g, 2.44 mmol) It was refluxed at 140 ° C. After cooling, the filtrate was concentrated to a column purified HX: MC = 3: 1 to give compound 1-5 (7.2g, 64%)

Preparation of Compound 1

In a round bottom flask (One neck rbf) 9- (9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, d] Furan-4-yl) -9H-carbazole (7.2 g, 15.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5 g, 18.8 mmol), tetrakis (triphenyl Phosphine) palladium (0) (1.8 g, 1.56 mmol), potassium carbonate (4.3 g, 31.2 mmol), 1,4-dioxane / water (100 ml / 25 ml) mixture was refluxed at 120 ° C. for 4 hours. After filtering at 120 degreeC, it washed with 1, 4- dioxane, distilled water, MeOH, and obtained compound 1 (C). (6.6g, 75%)

Compound C was synthesized in the same manner as in the preparation of Compound 1, except that A and B of the following [Table 1] to [Table 7] were used as intermediates in Preparation Example 1.

Preparation of Compound 129-1

In a round bottom flask (One neck rbf), 1-bromo-2,4-difluorobenzene (40 g, 207 mmol), (2-chloro-6-methoxyphenyl) boronic acid (42.4 g, 227 mmol) , Tetrakis (triphenylphosphine) palladium (0) (23 g, 20.7 mmol), potassium carbonate (57 g, 414 mmol), toluene / ethanol / water (600 ml / 150 ml / 150 ml) mixture was refluxed at 110 ° C.

Extracted with dichloromethane and dried over MgSO ₄ . The silica gel filter was then concentrated to give compound 129-1. (50 g, 94%)

Preparation of Compound 129-2

In a round bottom flask (One neck rbf) of 2'-chloro-2,4-difluoro-6'-methoxy-1,1'-biphenyl (50 g, 196 mmol), dichloromethane (700 ml) The mixture was cooled to 0 ° C., BBr ₃ (28.3 mL, 294 mmol) was added dropwise, and the temperature was raised to room temperature, followed by stirring for 2 hours.

The reaction was terminated with distilled water and extracted with dichloromethane and dried over MgSO ₄ . Compound 129-2 was obtained by silica gel filter. (27.5g, 58%)

Preparation of Compound 129-3

In a round bottom flask (One neck rbf), 4-chloro-2 ', 4'-difluoro- [1,1'-biphenyl] -2-ol (27 g, 114 mmol), Cs ₂ CO ₃ ( 83 g, 285 mmol) of dimethylacetamide (300 ml) mixture was stirred at 120 ° C. After cooling, the mixture was filtered and the solvent of the filtrate was removed, followed by silica gel filtering to obtain a compound 129-3. (23g, 92%)

Preparation of Compound 129-4

In a round bottom flask (One neck rbf), 1-chloro-7-fluorodibenzo [b, d] furan (5.5 g, 24.9 mmol), 9H-carbazole (4.58 g, 27.4 mmol), Cs ₂ CO ₃ A mixture of (20 g, 62 mmol) of dimethylacetamide (60 ml) was refluxed at 170 ° C. for 6 h. After cooling, the mixture was filtered, the solvent was removed from the filtrate, and the column was purified to HX: MC = 3: 1, to obtain Compound 129-4. (7.6 g, 83%)

Preparation of Compound 129-5

In a round bottom flask (One neck rbf) 9- (9-chlorodibenzo [b, d] furan-3-yl) -9H-carbazole (7.5 g, 20.3 mmol), bis (pinacolato) dibo 1,4-dioxane of ron (10.3 g, 40.7 mmol), Pcy ₃ (1.14 g, 4.07 mmol), potassium acetate (5.97 g, 60.9 mmol), Pd ₂ (dba) ₃ (1.85 g, 2.03 mmol) ( 80 ml) was refluxed at 140 ° C. After cooling, the filtrate was filtered and concentrated to column purification HX: MC = 2: 1 to obtain the compound 129-5 (6.5g, 70%).

Preparation of Compound 129

In a round bottom flask (One neck rbf) 9- (9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, d] Furan-3-yl) -9H-carbazole (6.5 g, 14.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.54 g, 16.9 mmol), tetrakis (tri Phenylphosphine) palladium (0) (1.6 g, 1.41 mmol), potassium carbonate (3.9 g, 28.2 mmol), 1,4-dioxane / water (80 ml / 28.2 ml) mixture was refluxed at 120 ° C. for 4 hours. After filtering at 120 ° C., the mixture was washed with 1,4-dioxane, distilled water and MeOH to obtain compound 129 (F) (5.4 g, 68%).

Compound F was synthesized in the same manner as in the preparation of Compound 129, except that D and E of the following [Table 8] to [Table 14] were used as intermediates in Preparation Example 2.

Compounds 1 to 284 other than the compounds described in Tables 1 to 14 were also prepared in the same manner as in the above-described production examples.

Synthesis confirmation data of the compounds prepared above are as described in Tables 15 and 16 below.

compound	FD-Mass	compound	FD-Mass
One	m / z = 564.63 (C39H24N4O = 564.20)	2	m / z = 640.73 (C45H28N4O = 640.23)
3	m / z = 640.73 (C45H28N4O = 640.23)	4	m / z = 716.83 (C51H32N4O = 717.26)
5	m / z = 716.83 (C51H32N4O = 717.26)	6	m / z = 729.82 (C51H31N5O = 729.25)
7	m / z = 729.82 (C51H31N5O = 729.25)	8	m / z = 805.92 (C57H35N5O = 805.28)
9	m / z = 730.81 (C51H30N4O2 = 730.81)	10	m / z = 680.79 (C48H32N4O = 680.26)
11	m / z = 680.79 (C48H32N4O = 680.26)	12	m / z = 680.79 (C48H32N4O = 680.26)
13	m / z = 670.78 (C45H26N4OS = 670.18)	14	m / z = 654.71 (C45H26N4O2 = 654.21)
15	m / z = 654.71 (C45H26N4O2 = 654.21)	16	m / z = 670.78 (C45H26N4OS = 670.18)
17	m / z = 640.73 (C45H2N4O = 640.23)	18	m / z = 716.83 (C51H32N4O = 716.26)
19	m / z = 716.83 (C51H32N4O = 716.26)	20	m / z = 792.92 (C57H36N4O = 792.29)
21	m / z = 792.92 (C57H36N4O = 792.29)	22	m / z = 640.73 (C45H2N4O = 640.23)
23	m / z = 792.92 (C57H36N4O = 792.29)	24	m / z = 792.92 (C57H36N4O = 792.29)
25	m / z = 792.92 (C57H36N4O = 792.29)	26	m / z = 728.84 (C52H32N4O = 728.26)
27	m / z = 728.84 (C52H32N4O = 728.26)	28	m / z = 804.93 (C58H36N4O = 804.29)
29	m / z = 746.21 (C51H30N4OS = 746.21)	30	m / z = 756.89 (C54H36N4O = 756.29)
31	m / z = 756.89 (C54H36N4O = 756.29)	32	m / z = 679.81 (C49H33N3O = 679.26)
33	m / z = 746.88 (C51H30N4OS = 746.21)	34	m / z = 730.81 (C51H30N4O2 = 730.24
35	m / z = 730.81 (C51H30N4O2 = 730.24	36	m / z = 669.79 (C46H27N3OS = 669.19)
37	m / z = 640.73 (C45H28N4O = 640.23)	38	m / z = 640.73 (C45H28N4O = 640.23)
39	m / z = 716.83 (C51H32N4O = 717.26)	40	m / z = 716.83 (C51H32N4O = 717.26)
41	m / z = 716.83 (C51H43N4O = 716.26)	42	m / z = 716.83 (C51H32N4O = 717.26)
43	m / z = 715.84 (C52H33N3O = 715.26)	44	m / z = 715.84 (C52H33N3O = 715.26)
45	m / z = 640.73 (C45H28N4O = 640.23	46	m / z = 716.83 (C51H32N4O = 716.26)
47	m / z = 716.83 (C51H32N4O = 716.26)	48	m / z = 792.92 (C57H36N4O = 792.29)
49	m / z = 756.89 (C54H36N4O = 756.29)	50	m / z = 716.83 (C51H32N4O = 716.26)
51	m / z = 716.83 (C51H32N4O = 716.26)	52	m / z = 716.83 (C51H32N4O = 716.26)
53	m / z = 792.92 (C57H36N4O = 792.29)	54	m / z = 792.92 (C57H36N4O = 792.29)
55	m / z = 601.69 (C43H27N3O = 601.69)	56	m / z = 601.69 (C43H27N3O = 601.69)
57	m / z = 677.79 (C49H31N3O = 677.25)	58	m / z = 677.79 (C49H31N3O = 677.25)
59	m / z = 677.79 (C49H31N3O = 677.25)	60	m / z = 677.79 (C49H31N3O = 677.25)
61	m / z = 753.89 (C55H35N3O = 753.28)	62	m / z = 753.89 (C55H35N3O = 753.28)
63	m / z = 753.89 (C55H35N3O = 753.28)	64	m / z = 753.89 (C55H35N3O = 753.28)
65	m / z = 717.85 (C52H35N3O = 717.28)	66	m / z = 717.85 (C52H35N3O = 717.28)
67	m / z = 707.84 (C49H29N3OS = 707.20)	68	m / z = 691.77 (C49H29N3O2 = 691.23)
69	m / z = 613.70 (C44H27N3O = 613.22)	70	m / z = 689.80 (C50H31N3O = 689.25)
71	m / z = 689.80 (C50H31N3O = 689.25)	72	m / z = 689.80 (C50H31N3O = 689.25)
73	m / z = 765.90 (C56H35N3O = 765.28)	74	m / z = 765.90 (C56H35N3O = 765.28)
75	m / z = 729.86 (C53H35N3O = 729.28)	76	m / z = 719.20 (C50H29N3OS = 719.20)
77	m / z = 537.61 (C38H23N3O = 537.18)	78	m / z = 613.70 (C44H27N3O = 613.22)
79	m / z = 613.70 (C44H27N3O = 613.22)	80	m / z = 613.70 (C44H27N3O = 613.22)
81	m / z = 689.80 (C50H31N3O = 689.25)	82	m / z = 689.80 (C50H31N3O = 689.25)
83	m / z = 702.80 (C50H30N4O = 702.24)	84	m / z = 702.80 (C50H30N4O = 702.24)
85	m / z = 537.61 (C38H23N3O = 537.18)	86	m / z = 613.70 (C44H27N3O = 613.22)
87	m / z = 613.70 (C44H27N3O = 613.22)	88	m / z = 613.70 (C44H27N3O = 613.22)
89	m / z = 689.80 (C50H31N3O = 689.25)	90	m / z = 689.80 (C50H31N3O = 689.25)
91	m / z = 778.90 (C56H34N4O = 78.27)	92	m / z = 703.78 (C50H29N3O2 = 703.23)
93	m / z = 536.62 (C39H24N2O = 536.19)	94	m / z = 612.72 (C45H28N2O = 612.22)
95	m / z = 612.72 (C45H28N2O = 612.22)	96	m / z = 612.72 (C45H28N2O = 612.22)
97	m / z = 688.81 (C51H32N2O = 688.25)	98	m / z = 688.81 (C51H32N2O = 688.25)
99	m / z = 652.78 (C48H32N2O = 652.25)	100	m / z = 652.78 (C48H32N2O = 652.25)
101	m / z = 536.62 (C39H24N2O = 536.19)	102	m / z = 612.72 (C45H28N2O = 612.22)
103	m / z = 612.72 (C45H28N2O = 612.22)	104	m / z = 612.72 (C45H28N2O = 612.22)
105	m / z = 688.81 (C51H32N2O = 688.25)	106	m / z = 688.81 (C51H32N2O = 688.25)
107	m / z = 642.77 (C45H26N2OS = 642.18)	108	m / z = 626.70 (C45H27N2O2 = 626.20)
109	m / z = 563.65 (C40H25N3O = 563.20)	110	m / z = 639.73 (C46H29N3O = 639.23)
111	m / z = 639.73 (C46H29N3O = 639.23)	112	m / z = 715.84 (C52H33N3O = 715.26)
113	m / z = 715.84 (C52H33N3O = 715.26)	114	m / z = 715.84 (C52H33N3O = 715.26)
115	m / z = 639.74 (C46H29N3O = 639.23)	116	m / z = 715.84 (C52H33N3O = 715.26)
117	m / z = 664.75 (C47H28N4O = 664.23)	118	m / z = 740.85 (C53H32N4O = 740.26)
119	m / z = 740.85 (C53H32N4O = 740.26)	120	m / z = 740.85 (C53H32N4O = 740.26)
121	m / z = 816.94 (C59H36N4O = 816.29)	122	m / z = 816.94 (C59H36N4O = 816.29)
123	m / z = 829.94 (C59H35N5O = 829.28)	124	m / z = 829.94 (C59H35N5O = 829.28)
125	m / z = 729.82 (C51H31N5O = 729.25)	126	m / z = 805.92 (C57H35N5O = 805.28)
127	m / z = 702.80 (C50H30N4O = 702.24)	128	m / z = 766.27 (C55H34N4O = 766.27)
129	m / z = 564.63 (C39H24N4O = 564.20)	130	m / z = 640.73 (C45H28N4O = 640.23)
131	m / z = 640.73 (C45H28N4O = 640.23)	132	m / z = 716.83 (C51H32N4O = 717.26)
133	m / z = 716.83 (C51H32N4O = 717.26)	134	m / z = 729.82 (C51H31N5O = 729.25)
135	m / z = 729.82 (C51H31N5O = 729.25)	136	m / z = 805.92 (C57H35N5O = 805.28)
137	m / z = 730.81 (C51H30N4O2 = 730.81)	138	m / z = 680.79 (C48H32N4O = 680.26)
139	m / z = 680.79 (C48H32N4O = 680.26)	140	m / z = 680.79 (C48H32N4O = 680.26)
141	m / z = 670.78 (C45H26N4OS = 670.18)	142	m / z = 654.71 (C45H26N4O2 = 654.21)
143	m / z = 654.71 (C45H26N4O2 = 654.21)	144	m / z = 670.78 (C45H26N4OS = 670.18)
145	m / z = 640.73 (C45H2N4O = 640.23)	146	m / z = 716.83 (C51H32N4O = 716.26)
147	m / z = 716.83 (C51H32N4O = 716.26)	148	m / z = 792.92 (C57H36N4O = 792.29)
149	m / z = 792.92 (C57H36N4O = 792.29)	150	m / z = 640.73 (C45H2N4O = 640.23)
151	m / z = 792.92 (C57H36N4O = 792.29)	152	m / z = 792.92 (C57H36N4O = 792.29)
153	m / z = 792.92 (C57H36N4O = 792.29)	154	m / z = 728.84 (C52H32N4O = 728.26)
155	m / z = 728.84 (C52H32N4O = 728.26)	156	m / z = 804.93 (C58H36N4O = 804.29)
157	m / z = 746.21 (C51H30N4OS = 746.21)	158	m / z = 756.89 (C54H36N4O = 756.29)
159	m / z = 756.89 (C54H36N4O = 756.29)	160	m / z = 679.81 (C49H33N3O = 679.26)
161	m / z = 746.88 (C51H30N4OS = 746.21)	162	m / z = 730.81 (C51H30N4O2 = 730.24
163	m / z = 730.81 (C51H30N4O2 = 730.24	164	m / z = 669.79 (C46H27N3OS = 669.19)
165	m / z = 640.73 (C45H28N4O = 640.23)	166	m / z = 640.73 (C45H28N4O = 640.23)
167	m / z = 716.83 (C51H32N4O = 717.26)	168	m / z = 716.83 (C51H32N4O = 717.26)
169	m / z = 716.83 (C51H43N4O = 716.26)	170	m / z = 716.83 (C51H32N4O = 717.26)
171	m / z = 715.84 (C52H33N3O = 715.26)	172	m / z = 715.84 (C52H33N3O = 715.26)
173	m / z = 640.73 (C45H28N4O = 640.23	174	m / z = 716.83 (C51H32N4O = 716.26)
175	m / z = 716.83 (C51H32N4O = 716.26)	176	m / z = 792.92 (C57H36N4O = 792.29)
177	m / z = 756.89 (C54H36N4O = 756.29)	178	m / z = 716.83 (C51H32N4O = 716.26)
179	m / z = 716.83 (C51H32N4O = 716.26)	180	m / z = 716.83 (C51H32N4O = 716.26)
181	m / z = 792.92 (C57H36N4O = 792.29)	182	m / z = 792.92 (C57H36N4O = 792.29)
183	m / z = 601.69 (C43H27N3O = 601.69)	184	m / z = 601.69 (C43H27N3O = 601.69)
185	m / z = 677.79 (C49H31N3O = 677.25)	186	m / z = 677.79 (C49H31N3O = 677.25)
187	m / z = 677.79 (C49H31N3O = 677.25)	188	m / z = 677.79 (C49H31N3O = 677.25)
189	m / z = 753.89 (C55H35N3O = 753.28)	190	m / z = 753.89 (C55H35N3O = 753.28)
191	m / z = 753.89 (C55H35N3O = 753.28)	192	m / z = 753.89 (C55H35N3O = 753.28)
193	m / z = 717.85 (C52H35N3O = 717.28)	194	m / z = 717.85 (C52H35N3O = 717.28)
195	m / z = 707.84 (C49H29N3OS = 707.20)	196	m / z = 691.77 (C49H29N3O2 = 691.23)
197	m / z = 613.70 (C44H27N3O = 613.22)	198	m / z = 689.80 (C50H31N3O = 689.25)
199	m / z = 689.80 (C50H31N3O = 689.25)	200	m / z = 689.80 (C50H31N3O = 689.25)
201	m / z = 765.90 (C56H35N3O = 765.28)	202	m / z = 765.90 (C56H35N3O = 765.28)
203	m / z = 729.86 (C53H35N3O = 729.28)	204	m / z = 719.20 (C50H29N3OS = 719.20)
205	m / z = 537.61 (C38H23N3O = 537.18)	206	m / z = 613.70 (C44H27N3O = 613.22)
207	m / z = 613.70 (C44H27N3O = 613.22)	208	m / z = 613.70 (C44H27N3O = 613.22)
209	m / z = 689.80 (C50H31N3O = 689.25)	210	m / z = 689.80 (C50H31N3O = 689.25)
211	m / z = 702.80 (C50H30N4O = 702.24)	212	m / z = 702.80 (C50H30N4O = 702.24)
213	m / z = 537.61 (C38H23N3O = 537.18)	214	m / z = 613.70 (C44H27N3O = 613.22)
215	m / z = 613.70 (C44H27N3O = 613.22)	216	m / z = 613.70 (C44H27N3O = 613.22)
217	m / z = 689.80 (C50H31N3O = 689.25)	218	m / z = 689.80 (C50H31N3O = 689.25)
219	m / z = 778.90 (C56H34N4O = 78.27)	220	m / z = 703.78 (C50H29N3O2 = 703.23)
221	m / z = 536.62 (C39H24N2O = 536.19)	222	m / z = 612.72 (C45H28N2O = 612.22)
223	m / z = 612.72 (C45H28N2O = 612.22)	224	m / z = 612.72 (C45H28N2O = 612.22)
225	m / z = 688.81 (C51H32N2O = 688.25)	226	m / z = 688.81 (C51H32N2O = 688.25)
227	m / z = 652.78 (C48H32N2O = 652.25)	228	m / z = 652.78 (C48H32N2O = 652.25)
229	m / z = 536.62 (C39H24N2O = 536.19)	230	m / z = 612.72 (C45H28N2O = 612.22)
231	m / z = 612.72 (C45H28N2O = 612.22)	232	m / z = 612.72 (C45H28N2O = 612.22)
233	m / z = 688.81 (C51H32N2O = 688.25)	234	m / z = 688.81 (C51H32N2O = 688.25)
235	m / z = 642.77 (C45H26N2OS = 642.18)	236	m / z = 626.70 (C45H27N2O2 = 626.20)
237	m / z = 563.65 (C40H25N3O = 563.20)	238	m / z = 639.73 (C46H29N3O = 639.23)
239	m / z = 639.73 (C46H29N3O = 639.23)	240	m / z = 715.84 (C52H33N3O = 715.26)
241	m / z = 715.84 (C52H33N3O = 715.26)	242	m / z = 715.84 (C52H33N3O = 715.26)
243	m / z = 639.74 (C46H29N3O = 639.23)	244	m / z = 715.84 (C52H33N3O = 715.26)
245	m / z = 664.75 (C47H28N4O = 664.23)	246	m / z = 740.85 (C53H32N4O = 740.26)
247	m / z = 740.85 (C53H32N4O = 740.26)	248	m / z = 740.85 (C53H32N4O = 740.26)
249	m / z = 816.94 (C59H36N4O = 816.29)	250	m / z = 816.94 (C59H36N4O = 816.29)
251	m / z = 829.94 (C59H35N5O = 829.28)	252	m / z = 829.94 (C59H35N5O = 829.28)
253	m / z = 729.82 (C51H31N5O = 729.25)	254	m / z = 805.92 (C57H35N5O = 805.28)
255	m / z = 702.80 (C50H30N4O = 702.24)	256	m / z = 766.27 (C55H34N4O = 766.27)
257	m / z = 716.83 (C51H32N4O = 716.26)	258	m / z = 654.71 (C45H26N4O2 = 654.21)
259	m / z = 730.81 (C51H30N4O2 = 730.24)	260	m / z = 654.71 (C45H26N4O2 = 654.21)
261	m / z = 730.81 (C51H30N4O2 = 730.24)	262	m / z = 730.81 (C51H30N4O2 = 730.24)
263	m / z = 716.83 (C51H32N4O = 716.26)	264	m / z = 654.71 (C45H26N4O2 = 654.21)
265	m / z = 730.81 (C51H30N4O2 = 730.24)	266	m / z = 730.81 (C51H30N4O2 = 730.24)
267	m / z = 746.88 (C51H30N4OS = 741.21)	268	m / z = 756.89 (C54H36N4O = 756.29)
269	m / z = 614.71 (C43H26N4O = 614.21)	270	m / z = 664.77 (C47H28N4O = 664.23)
271	m / z = 729.84 (C51H31N5O = 729.25)	272	m / z = 729.84 (C51H31N5O = 729.25)
273	m / z = 654.73 (C45H26N4O2 = 654.21)	274	m / z = 670.79 (C45H26N4OS = 670.18)
275	m / z = 779.90 (C55H33N5O = 779.27)	276	m / z = 829.96 (C59H35N5O = 829.28)
277	m / z = 704.79 (C49H28N4O2 = 704.22)	278	m / z = 720.85 (C49H28N4OS = 720.20)
279	m / z = 754.85 (C53H30N4O2 = 754.24)	280	m / z = 770.91 (C53H30N4OS = 770.21)
281	m / z = 693.82 (C48H27N3OS = 693.19)	282	m / z = 758.90 (C52H30N4OS = 758.21)
283	m / z = 799.97 (C54H29N3OS2 = 799.18)	284	m / z = 783.90 (C54H29N3O2S = 783.20)

compound	1 H NMR (CDCl 3, 200Mz )
One	δ = 8.55 (1h, d), 8.28 (4h, d), 8.12 (1H, d), 7.94-7.89 (2H, q), 7.75 (1H, d), 7.63-7.82 (2H, m), 7.51- 7.25 (13 H, m)
2	δ = 8.55 (1H, d), 8.28 (4H, d), 8.18 (1H, d), 7.94-7.89 (2H, q), 7.79-7.75 (2H, q), 7.62 (2H, m), 7.52- 7.5 (16H, m)
3	δ = 8.55 (1H, d), 8.28 (4H, d), 7.94-7.87 (3H, q), 7.77-7.69 (4H, m), 7.52-7.2 (16H, m)
5	δ = 8.28 (4H, d), 8.18 (1H, d), 8.00 (1H, d), 7.89-7.87 (2H, t) 7.77-7.69 (4H, m), 7.52-7.25 (16H, m)
10	δ = 8.39 (1H, s), 8.28 (4H, d), 8.12-8.059 (2H, t), 7.89 (1H, d), 7.75 (1H, d), 7.69 (1H, s), 7.63-7.61 ( 3H, m), 7.51 ~ 7.24 (13H, m)
17	δ = 8.52 (1H, d), 8.28-8.24 (3H, m), 8.12 (1H, d), 7.94-7.89 (2H, d), 7.75-7.70 (2H, m), 7.62-7.25 (19H, m )
18	δ = 8.53 (1H, d), 8.28-8.18 (4H, m), 7.94-7.89 (2H, q), 7.79-7.70 (3H, m), 7.62-7.25 (22H, m)
129	δ = 8.55 (1H, d), 8.28 (4H, d), 8.12 (1H, d), 7.94-7.89 (2H, q), 7.75 (2H, d), 7.73 (1H, s), 7.63-7.82 ( 2H, m), 7.51 ~ 7.25 (12H, m)
130	δ = 8.55 (1H, d), 8.28 (4H, d), 8.18 (1H, d), 7.94-7.89 (2H, q), 7.79-7.73 (3H, m), 7.62 (2H, m), 7.52- 7.25 (15 H, m)
131	δ = 8.55 (1H, d), 8.28 (4H, d), 7.94-7.87 (3H, m), 7.77-7.73 (5H, m), 7.52-7.25 (15H, m)
133	δ = 8.28 (4H, d), 8.18 (1H, d), 8.0 (1H, d), 7.89-7.87 (2H, t), 7.77-7.73 (5H, m), 7.62 (1H, m), 7.52- 7.41 (18H, m)
138	δ = 8.39 (1H, d), 8.28 (4H, d), 8.12-8.09 (2H, t), 7.89 (1H, d), 7.75-7.61 (6H, m), 7.51-7.41 (10H, m),
145	δ = 8.55 (1H, d), 8.28-8.24 (3H, m), 8.12 (1H, d), 7.94-7.89 (2H, q), 7 75-7.70 (3H, t), 7.63-7.25 (18H, m)
146	δ = 8.55 (1H, d), 8.28-8.18 (4H, m), 7.94-7.89 (2H, d), 7.79-7.70 (4H, m), 7.62-7.25 (21H, m)
257	δ = 8.55 (1H, d), 8.24 (2H, d), 8.12 (1H, d), 7.94-7.89 (2H, q) 7.75-7.70 (3H, m), 7.63-7.25 (23H, m)
265	δ = 8.28 (2H, d), 8.18-8.12 (2H, q), 8.00 (1H, d), 7.89-7.73 (7H, m), 7.66-7.82 (3H, m), 7.52-7.29 (15H, m )
271	δ = 8.55 (2H, d), 8.36 (4H, t), 7.98-7.74 (3H, m), 7.82 (1H, d), 7.69-7.50 (15H, m), 7.35 (2H, t), 7.26- 7.25 (2H, d), 7.16 (2H, t)
272	δ = 8.55 (2H, d), 8.36 (4H, t), 8.12 (1H, d), 7.98-7.94 (3H, m), 7.82 (1H, d), 7.69-7.50 (14H, m), 7.35 ( 2H, t), 7.25 ~ 7.16 (4H, m)
282	δ = 8.55 (2H, d), 8.05 (1H, d), 7.98-7.82 (7H, m), 7.69-7.35 (16H, m), 7.26-7.25 (2H, d), 7.16 (2H, t)

1) Fabrication of organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then treated with UVO for 5 minutes using UV in a UV cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove ITO work function and residual film in a vacuum state, and then transferred to an organic deposition thermal deposition apparatus.

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

The light emitting layer was thermally vacuum deposited on it as follows. As the host, the light emitting layer was Ir (ppy) ₃ as a compound and a green phosphorescent dopant described in [Table 17]. (tris (2-phenylpyridine) iridium) was used to dope 400 Å of the host by irradiating Ir (ppy) ₃ to 7% of the light emitting layer deposition thickness. Subsequently, 60 Å of BCP was deposited using the hole blocking layer, and Alq ₃ was deposited on the electron transport layer. Was deposited at 200 Hz. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to form a electron injecting layer by depositing 10 Å thick. Then, an aluminum (Al) cathode is deposited to a thickness of 1200 층 on the electron injecting layer to form a cathode. A light emitting device was manufactured.

On the other hand, all the organic compounds required for OLED device fabrication was vacuum sublimation purification under 10 ^-6 ~ 10 ^-8 torr each material was used in the OLED production.

2) Driving voltage and luminous efficiency of organic EL device

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience Inc. with the measurement result. T ₉₀ was measured at cd / m ² . Properties of the organic electroluminescent device of the present invention are shown in [Table 17].

	compound	Driving voltage (V)	Efficiency (cd / A)	Color coordinates (x, y)	Life (T 90 )
Comparative Example 1	A	5.84	44.3	(0.276, 0.674)	57
Comparative Example 2	B	5.57	51.2	(0.286, 0.673)	58
Comparative Example 3	C	5.43	55.4	(0.286, 0.678)	77
Comparative Example 4	D	5.92	57.2	(0.288, 0.677)	43
Comparative Example 5	E	5.62	54.5	(0.281, 0.674	65
Comparative Example 6	F	5.33	55.5	(0.285, 0.676)	71
Comparative Example 7	G	5.72	56.3	(0.284, 0.679)	69
Example 1	One	5.02	56.4	(0.287, 0.673)	183
Example 2	2	3.54	80.1	(0.287, 0.677)	172
Example 3	3	3.53	76.2	(0.289, 0.672)	177
Example 4	5	3.82	73.4	(0.287, 0.677)	161
Example 5	7	4.42	68.4	(0.287, 0.674)	141
Example 6	10	4.44	62.3	(0.289, 0.679)	138
Example 7	17	3.92	78.2	(0.276, 0.672)	147
Example 8	18	3.75	71.3	(0.278, 0.673)	173
Example 9	19	3.72	79.1	(0.280, 0.676)	175
Example 10	22	3.88	79.3	(0.278, 0.672)	178
Example 11	28	4.23	67.2	(0.283, 0.684)	142
Example 12	29	4.12	63.4	(0.287, 0.687)	139
Example 13	34	4.03	69.2	(0.274, 0.678)	146
Example 14	38	3.88	78.1	(0.277, 0.677)	151
Example 15	39	3.76	77.2	(0.277, 0.678)	132
Example 16	43	4.12	67.3	(0.276, 0.673)	145
Example 17	48	4.32	72.3	(0.284, 0.674)	157
Example 18	51	4.12	74.2	(0.283, 0.681)	154
Example 19	53	4.33	72.3	(0.274, 0.677)	155
Example 20	59	3.99	69.2	(0.276, 0.678)	156
Example 21	62	3.89	70.2	(0.289, 0.670)	142
Example 22	65	4.12	69.6	(0.286, 0.671)	132
Example 23	67	3.87	69.4	(0.288, 0.674)	152
Example 24	70	4.03	64.2	(0.285, 0.673)	142
Example 25	71	3.76	70.3	(0.273, 0.677)	144
Example 26	75	3.65	72.2	(0.287, 0.673)	156
Example 27	77	3.99	69.9	(0.288, 0.679)	165
Example 28	80	4.21	65.2	(0.286, 0.681)	154
Example 29	83	4.13	68.3	(0.275, 0.679)	167
Example 30	86	4.21	71.3	(0.283, 0.677)	153
Example 31	90	4.32	69.2	(0.286, 0.678)	152
Example 32	92	4.12	73.2	(0.284, 0.678)	157
Example 33	95	4.22	64.2	(0.271, 0.673)	143
Example 34	100	3.75	63.2	(0.283, 0.687)	144
Example 35	101	4.11	63.1	(0.283, 0.677)	173
Example 36	109	4.21	63.6	(0.289, 0.674)	153
Example 37	115	4.32	66.3	(0.287, 0.678)	154
Example 38	118	4.32	65.2	(0.271, 0.679)	144
Example 39	121	4.34	62.4	(0.273, 0.689)	149
Example 40	125	3.66	73.1	(0.274, 0.687)	162
Example 41	127	3.79	71.4	(0.279, 0.673)	170
Example 42	129	3.80	69.9	(0.275, 0.675)	170
Example 43	130	3.90	67.4	(0.282, 0.676)	167
Example 44	131	3.81	62.9	(0.283, 0.673)	155
Example 45	133	3.99	70.6	(0.274, 0.679)	169
Example 46	135	3.82	72.4	(0.272, 0.676)	168
Example 47	138	3.72	73.6	(0.273, 0.675)	174
Example 48	145	3.67	68.7	(0.274, 0.676)	166
Example 49	146	4.42	65.2	(0.273, 0.676)	143
Example 50	147	4.43	63.4	(0.283, 0.677)	132
Example 51	150	3.89	75.9	(0.284, 0.676)	142
Example 52	156	3.71	71.4	(0.283, 0.675)	164
Example 53	157	3.72	69.4	(0.279, 0.676)	169
Example 54	162	3.98	76.6	(0.291, 0.677)	174
Example 55	166	4.59	67.3	(0.293, 0.684)	142
Example 56	167	4.42	66.5	(0.282, 0.674)	133
Example 57	171	4.52	65.1	(0.281, 0.678)	131
Example 58	173	4.10	73.9	(0.283, 0.675)	165
Example 59	176	3.91	73.4	(0.288, 0.676)	158
Example 60	179	4.13	68.4	(0.288, 0.674)	149
Example 61	181	4.42	66.1	(0.287, 0.675)	143
Example 62	187	4.67	63.5	(0.277, 0.678)	165
Example 63	190	4.32	69.4	(0.287, 0.676)	166
Example 64	193	4.65	66.8	(0.275, 0.677)	142
Example 65	195	4.32	67.8	(0.285, 0.680)	142
Example 66	198	4.21	71.3	(0.287, 0.680)	135
Example 67	199	3.93	67.4	(0.278, 0.681)	149
Example 68	203	4.12	64.6	(0.281, 0.677)	132
Example 69	205	3.95	67.8	(0.287, 0.676)	142
Example 70	208	3.89	68.8	(0.284, 0.677)	138
Example 71	211	4.23	67.4	(0.273, 0.673)	163
Example 72	214	4.42	62.2	(0.279, 0.676)	164
Example 73	218	4.33	68.3	(0.279, 0.677)	131
Example 74	220	4.53	67.8	(0.282, 0.687)	141
Example 75	223	4.23	67.4	(0.283, 0.676)	153
Example 76	228	4.32	78.3	(0.284, 0.674)	163
Example 77	229	4.12	68.4	(0.289, 0.674)	142
Example 78	238	3.78	62.8	(0.284, 0.672)	141
Example 79	241	4.32	66.4	(0.283, 0.681)	158
Example 80	246	4.21	68.9	(0.279, 0.680)	133
Example 81	247	3.66	73.4	(0.279, 0.674)	178
Example 82	249	3.79	72.8	(0.278, 0.671)	177
Example 83	253	4.64	69.3	(0.275, 0.677)	154
Example 84	255	3.78	72.5	(0.284, 0.673)	171
Example 85	257	4.32	70.4	(0.287, 0.676)	158
Example 86	258	4.01	69.2	(0.284, 0.678)	143
Example 87	261	3.86	72.3	(0.279, 0.675)	152
Example 88	263	3.65	78.8	(0.279, 0.670)	177
Example 89	264	3.64	80.3	(0.281, 0.669)	185
Example 90	265	3.76	77.6	(0.282, 0.673)	162
Example 85	257	4.32	70.4	(0.287, 0.676)	158
Example 86	258	4.01	69.2	(0.284, 0.678)	143
Example 87	261	3.86	72.3	(0.279, 0.675)	152
Example 88	263	3.65	78.8	(0.279, 0.670)	177
Example 89	264	3.64	80.3	(0.281, 0.669)	185
Example 90	265	3.76	77.6	(0.282, 0.673)	162
Example 91	271	3.62	75.8	(0.288, 0.671)	152
Example 92	272	3.82	68.3	(0.279, 0.674)	139
Example 93	282	3.67	72.2	(0.281, 0.668)	148

As a result of device evaluation, it was confirmed that the efficiency, particularly the life characteristics, of the heterocyclic compound of the present invention are excellent. Long life is the most important factor for the commercialization of materials. In particular, the strong electron donor nature of the oxygen of dibenzofuran can reduce the device life due to the increased electron instability of the LUMO site, and the N-containing ring at the carbon positions 2,4 of the dibenzofuran is particularly due to the Ortho and para orientation. Although more affected when substituted, the compound according to the present invention can improve the life of the device by the N-containing ring is located on carbon number 1.

In particular, when an N-containing ring, such as a triazine, is substituted at the carbon position of dibenzofuran, a steric hindrance occurs at a rigid position in dibenzofuran, and the molecular structure is present in the form of a broken structure, resulting in an empty space in the deposition of molecules. In addition to enhancing the electron transfer capability, the conjugation length is shortened, resulting in a high T1 value. Substitution at the 2 or 4 carbon position of dibenzofuran may lead to a factor that impairs the charge transfer capacity (Chem. Eur. J. 2013, 19, 1194-1198). This can be confirmed through Comparative Examples 5 and 6.

Claims (12)

1. Heterocyclic compounds represented by the formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,

   L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, a is an integer of 1 to 3, when a is 2 or more, L is the same as or different from each other,

   R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, b and c each represent an integer of 1 to 3 R9 is the same as or different from each other when b is 2 or more, and R10 is the same as or different from each other when c is 2 or more.
2. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by one of Formulas 2 to 5:

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   In Chemical Formulas 2 to 5, the substituents are as defined in Chemical Formula 1.
3. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by one of Formulas 6 to 8.

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   In Chemical Formulas 6 to 8,

   Definitions of R1 to R10, L, a, b and c are the same as the definition in Formula 1,

   X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N,

   R11 to R15 and R17 to R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.
4. The method according to claim 3,

   

   Is a heterocyclic compound represented by one of the following Chemical Formulas 9 to 12:

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   [Formula 12]

   

   In Formula 9, at least one of X1, X3 and X5 is N, and the others are as defined in Formula 6,

   In Formula 10, at least one of X1, X2 and X5 is N, and the others are as defined in Formula 6,

   In Formula 11, at least one of X 1 to X 3 is N, and the others are as defined in Formula 6,

   In Formula 12, at least one of X1, X2 and X5 is N, and the others are as defined in Formula 6,

   R12, R14 and R23 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.
5. The heterocyclic compound according to claim 4, wherein Formula 9 is selected from the following structural formulas:

   

   In the above structural formula, R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.
6. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

   

   

   

   

   

   

   

   

   

   

   

   

   
7. A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound according to any one of claims 1 to 6. Phosphorescent organic light-emitting device.
8. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
9. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, the light emitting layer comprises a host material, and the host material includes the heterocyclic compound.
10. The organic light emitting device of claim 7, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
11. The organic light emitting device of claim 7, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the heterocyclic compound.
12. The method of claim 7, wherein the organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. The organic light emitting device further comprises one or two or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

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