KR20200056811A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1, and an organic light emitting device comprising the same. When the compound represented by the chemical formula 1 is used in an organic material layer, it is possible to lower a driving voltage and improve light efficiency of a device, and improve lifespan characteristics of the device by thermal stability of the compound.

Description

A heterocyclic compound and an organic light emitting device comprising the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

The electroluminescent device is a type of self-emissive display device, and has a wide viewing angle, excellent contrast, and high 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 two electrodes are combined and paired in an organic thin film, and then disappear and shine. 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 as needed. For example, as the organic thin film material, a compound that can itself constitute a light emitting layer may be used, or a compound capable of serving as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material for the organic thin film, a compound capable of performing roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

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

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

The present invention is to provide a heterocyclic compound and an organic light emitting device comprising the same.

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

[Formula 1]

In Chemical Formula 1,

X ₁ to X ₃ are the same as or different from each other, and each independently, CRa; Or N,

At least one of X ₁ to X ₃ is N,

Ra is hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; and -P (= O) RR ',

L ₁ to L ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Z ₁ to Z ₄ are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR ',

m, n, p and q are integers from 1 to 5, and when m, n, p and q are each 2 or more, the substituents in parentheses are the same or different from each other,

R, R 'and R "are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

In addition, in one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a heterocyclic compound represented by Chemical Formula 1 above. Provides

The compound described in this specification can be used as an organic material layer material for 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, a charge generating material in an organic light emitting device. In particular, the compound may be used as a charge generating layer material or an electron transport layer material for an organic light emitting device.

When the compound represented by Chemical Formula 1 is used in the organic material layer, the driving voltage of the device can be lowered, the light efficiency is improved, and the life characteristics of the device can be improved by thermal stability of the compound.

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.

Hereinafter, the present application will be described in detail.

The term "substitution" means that the hydrogen atom bonded to the 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 the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

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

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

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. 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 a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. 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, etc. It may be, but is not limited to this.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group 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 to or condensed with another ring group. Here, the other cyclic group may be a cycloalkyl group, but may be another type of cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. 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, monocyclic or polycyclic 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 to or condensed with another ring group. Here, the other cyclic group may be a heterocycloalkyl group, but may be another kind of cyclic group, for example, a cycloalkyl group, an aryl group, a heteroaryl group. 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 6 to 60 carbon atoms or a monocyclic ring, 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 another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyre Neil group, tetrasenyl group, pentasenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof And the like, but are not limited thereto.

In the present specification, the phosphine oxide group is represented by -P (= O) R ₁₀₃ R ₁₀₄ , and R ₁₀₃ and R ₁₀₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl group; Alkoxy groups; Cycloalkyl group; Aryl group; And a heterocyclic group. The phosphine oxide group is specifically a diphenylphosphine oxide group, a dinaphthyl phosphine oxide, and the like, but is not limited thereto.

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

In the present specification, the 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 S, O, Se, N or Si as a hetero atom, monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic group 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 another 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 pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, 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, quinozolinyl group, naphthyridyl group, acridinyl group, phenanthridy Niyl group, imidazopyridinyl group, diazanaphthalenyl group, triazinden group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , Dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo [2,3-a] carbazolyl group, indolo [2,3-b] carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo [b, f] azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthilidinyl 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, 5,11-dihydroindeno [1,2-b ] Carbazolyl 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 groups; Diarylamine group; Diheteroarylamine group; Alkylarylamine groups; Alkyl heteroarylamine groups; And may be selected from the group consisting of an aryl heteroarylamine group, the number of carbon is not particularly limited, it is preferably 1 to 30. Specific examples of the amine group are 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 A nilamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, an arylene group means one having two bonding positions on the aryl group, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group. In addition, the heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as “adjacent” to each other.

In the present specification, the term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited if the position where the hydrogen atom is substituted, that is, the position where the substituent is substitutable, When 2 or more are substituted, 2 or more substituents may be the same or different from each other.

In the present specification, "substituted or unsubstituted" means C1 to C60 straight or branched chain alkyl; C2 to C60 straight or branched chain alkenyl; C2 to C60 straight or branched chain alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R "; -P (= O) RR '; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine It means that it is substituted or unsubstituted with one or more substituents, or substituted or unsubstituted with two or more substituents selected from the substituents exemplified above.

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

In one embodiment of the present application, X ₁ to X ₃ are the same as or different from each other, and each independently CRa; Or N.

In one embodiment of the present application, at least one of X ₁ to X ₃ may be N.

In an exemplary embodiment of the present application, X ₁ and X ₂ may be N, and X ₃ may be CRa.

In one embodiment of the present application, X ₁ and X ₃ may be N, and X ₂ may be CRa.

In one embodiment of the present application, X ₁ to X ₃ may be N.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,

L ₁ to L ₄ , Z ₁ to Z ₄ , m, n, p, q, X ₂ and X ₃ are the same as defined in Chemical Formula 1 above.

In particular, in the case of Chemical Formula 2, electron mobility of HOMO and LUMO is faster than that of Chemical Formula 3 because the degree of separation is greater than that of Chemical Formula 3. Therefore, it may be more excellent in terms of driving and efficiency, and also in the case of Chemical Formula 3, the electron distribution is widely distributed compared to Chemical Formula 2, and thus excellent in terms of life.

In one embodiment of the present application, Ra is hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; and -P (= O) RR '.

In another exemplary embodiment, Ra is hydrogen; A substituted or unsubstituted aryl group; And it may be selected from the group consisting of a substituted or unsubstituted heteroaryl group.

In another exemplary embodiment, Ra is hydrogen; A substituted or unsubstituted C6 to C60 aryl group; And it may be selected from the group consisting of substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ra is hydrogen; A substituted or unsubstituted C6 to C40 aryl group; And it may be selected from the group consisting of substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ra is hydrogen; C6 to C40 aryl group; And C2 to C40 heteroaryl groups.

In another exemplary embodiment, Ra may be hydrogen.

In another exemplary embodiment, Ra may be a phenyl group.

In one embodiment of the present application, L ₁ to L ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted arylene group; Or it may be a substituted or unsubstituted heteroarylene group.

In another exemplary embodiment, L ₁ to L ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another exemplary embodiment, L ₁ to L ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.

In another exemplary embodiment, L ₁ to L ₄ are the same as or different from each other, and each independently, C6 to C40 arylene groups; Or it may be a C2 to C40 heteroarylene group.

In another exemplary embodiment, L ₁ to L ₄ are the same as or different from each other, and each independently, C6 to C20 arylene groups; Or it may be a C2 to C20 heteroarylene group.

In another exemplary embodiment, L ₁ to L ₄ are the same as or different from each other, and each independently, a phenylene group; Biphenylene group; Triphenylene group; Phenanthrene group; Naphthylene group; Divalent carbazole group; Divalent dibenzofuran group; Divalent dibenzothiophene group; A divalent quinazoline group; Or it may be a divalent pyridine group.

In one embodiment of the present application, Z ₁ to Z ₄ are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR '.

In another exemplary embodiment, Z ₁ to Z ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR '.

In another exemplary embodiment, Z ₁ to Z ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C6 to C40 aryl group; A substituted or unsubstituted C2 to C40 heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR '.

In another exemplary embodiment, Z ₁ to Z ₄ are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C6 to C40 aryl group; A substituted or unsubstituted C2 to C40 heteroaryl group; -CN; And -P (= O) RR '.

In another exemplary embodiment, Z ₁ to Z ₄ are the same as or different from each other, and each independently hydrogen; C6 to C40 aryl group; A C2 to C40 heteroaryl group unsubstituted or substituted with a C6 to C40 aryl group; -CN; And -P (= O) RR '.

In another exemplary embodiment, Z ₁ to Z ₄ are the same as or different from each other, and each independently hydrogen; Phenyl group; Triphenylenyl group; Dibenzofuran group; Carbazole; Dibenzothiophene group; Quinoline group; Pyridine group; A quinazoline group unsubstituted or substituted with a phenyl group; -CN; Or -P (= O) RR '.

In an exemplary embodiment of the present application, Z ₁ to Z ₄ are carbazole, 1,3-di (9H-carbazole-9-yl) benzyl (1,3-di (9H-carbazol-9) -yl) benzyl) has high T ₁ and hole transport capacity. The exciton generated in the light emitting layer by high T ₁ can be bound, and the triphenylene group and dibenzofuran group also strengthen the hole transport ability to polarize the molecule itself, driving the device, efficiency And the lifetime can be particularly improved.

Also, in the case of a phosphine group, electrons are not distributed, and accordingly, electrons can be prevented from spreading widely. In the case of an aryl group substituted with a cyano group, the efficiency of the device can be improved by stabilizing the molecule when electrons are injected under the influence of an electron withdrawing group.

In one embodiment of the present application, R, R 'and R "are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted It may be a heteroaryl group.

In another exemplary embodiment, R, R 'and R "are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group. have.

In another exemplary embodiment, R, R 'and R "are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group. have.

In another exemplary embodiment, the R, R 'and R "are the same as or different from each other, and may be each independently a C1 to C40 alkyl group; or a C6 to C40 aryl group.

In another exemplary embodiment, R, R 'and R "may be the same as or different from each other, and each independently a methyl group; or a phenyl group.

In another exemplary embodiment, R, R 'and R "may be a phenyl group.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 5 to 7.

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 5 to 7,

L ₃ , L ₄ , Z ₁ to Z ₄ , m, n, p, q, X ₁ to X ₃ are the same as defined in Chemical Formula 1,

L ₂₂ is a substituted or unsubstituted polycyclic arylene group; Or a substituted or unsubstituted heteroarylene group,

L ₃₁ and L ₃₂ is the same as or different from each other, and each independently a substituted or unsubstituted polycyclic arylene group,

Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR '.

In one embodiment of the present application, L ₂₂ is a substituted or unsubstituted polycyclic arylene group; Or a substituted or unsubstituted heteroarylene group.

In another exemplary embodiment, L ₂₂ is a substituted or unsubstituted C10 to C60 polycyclic arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In another exemplary embodiment, L ₂₂ is a substituted or unsubstituted C10 to C40 polycyclic arylene group; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

In another exemplary embodiment, L ₂₂ is a C10 to C40 polycyclic arylene group; Or a C2 to C40 heteroarylene group.

In another exemplary embodiment, L ₂₂ is a naphthylene group; Phenanthrene group; Triphenylene group; Divalent dibenzofuran group; Divalent carbazole group; Divalent dibenzothiophene group; Or it may be a divalent pyridine group.

In one embodiment of the present application, L ₃₁ And L ₃₂ may be the same or different from each other, and each independently a substituted or unsubstituted polycyclic arylene group.

In another exemplary embodiment, L ₃₁ and L ₃₂ may be the same or different from each other, and each independently a substituted or unsubstituted C10 to C60 polycyclic arylene group.

In another exemplary embodiment, L ₃₁ and L ₃₂ may be the same or different from each other, and each independently a substituted or unsubstituted C10 to C40 polycyclic arylene group.

In another exemplary embodiment, L ₃₁ and L ₃₂ may be the same as or different from each other, and each independently a C10 to C40 polycyclic arylene group.

L ₃₁ in another embodiment L ₃₂ are the same as or different from each other, and each independently a naphthylene group; Or it may be a phenanthrene group.

In one embodiment of the present application, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR '.

In another exemplary embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C6 to C60 aryl group; And substituted or unsubstituted C2 to C60 heteroaryl groups.

In another exemplary embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; And substituted or unsubstituted C2 to C60 heteroaryl groups.

In another exemplary embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; And C2 to C40 heteroaryl groups.

In another exemplary embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; Pyridine group; Or it may be a carbazole group.

In one embodiment of the present application, Chemical Formula 5 may be represented by any one of the following Chemical Formulas 5-1 to 5-4.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

In Chemical Formulas 5-1 to 5-4, L ₃ , L ₄ , Z ₁ to Z ₄ , p, q, and X ₁ to X ₃ are the same as defined in Chemical Formula 5.

In an exemplary embodiment of the present application, Chemical Formula 6 may be represented by any one of the following Chemical Formulas 6-1 to 6-3.

[Formula 6-1]

[Formula 6-2]

[Formula 6-3]

In Chemical Formulas 6-1 to 6-3, Z ₁ , Z ₂₂ , L ₂₂ , L ₃ , L ₄ , Z ₃ , Z ₄ , n, p, q, and X ₁ to X ₃ are represented by Chemical Formula 6 Same as definition.

In one embodiment of the present application, Chemical Formula 1 provides a heterocyclic compound represented by any one of the following compounds.

In addition, by introducing various substituents to the structure of Formula 1, it is possible to synthesize a compound having the inherent properties of the introduced substituent. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a charge generating layer material used in manufacturing an organic light emitting device, the conditions required for each organic material layer are satisfied You can synthesize a substance to let.

In addition, by introducing various substituents to the structure of Chemical Formula 1, it is possible to finely adjust the energy band gap, on the other hand, to improve the properties at the interface between organic substances, and to use various materials.

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

Details of the heterocyclic compound represented by Chemical 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 one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the blue organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the electron transport layer of the blue organic light emitting device.

In one 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 for the green organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the electron transport layer of the green organic light emitting device.

In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the red organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the electron transport layer of the red organic light emitting device.

The organic light-emitting device of the present invention can be manufactured by a conventional method and a method of manufacturing an organic light-emitting device, except that one or more layers of organic materials are formed using the aforementioned heterocyclic compound.

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

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

As another example, the organic material layer including the heterocyclic compound includes 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 includes an electron injection layer or an electron transport layer, and the electron transport layer or electron injection layer may include the heterocyclic compound.

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

1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to one embodiment of the present application. However, the scope of the present application is not intended to be limited by these drawings, and the structure of the organic light emitting device known in the art may 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 structure is not limited to this, 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 stacked structure, and if necessary, the remaining layers other than the light emitting layer may be omitted, and other necessary functional layers may be further added.

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 Formula 1 are illustrated below, but these are for illustration only and are not intended to limit the scope of the present application, and are known in the art Materials can be replaced.

As the anode material, materials having a relatively large work function may be used, and a transparent conductive oxide, metal, or 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), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

As the cathode material, materials having a relatively low work function may be used, and a metal, metal oxide, or 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; There is 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 U.S. Patent No. 4,356,429 or 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 (Polyaniline / Dodecylbenzenesulfonic acid) or poly ( 3,4-ethylenedioxythiophene) / poly (4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), polyaniline / Camphor sulfonic acid or polyaniline / Polyaniline / Poly (4-styrene-sulfonate) can be used.

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

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used, as well as low molecular weight materials and high molecular weight materials.

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

Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials can be used by depositing them as separate sources, or by premixing and depositing them as one source. Further, a fluorescent material may be used as the light emitting material, but it may also be used as a phosphorescent material. As the light emitting material, a material that combines holes and electrons injected from the anode and the cathode to emit light may be used alone, but materials in which the host material and the dopant material are involved in light emission may be used.

When a host of light-emitting materials is mixed and used, a host of the same series may be mixed or used, or a host of other series may be mixed and used. For example, two or more types of materials 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 an exemplary embodiment of the present application may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

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

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

< Manufacturing example >

< Manufacturing example  1> Preparation of compound 2

Preparation of compound 2-1

2,4-dichloro-6-phenyl-1,3,5-triazine (30g, 132.71mmol) and phenylboronic acid acid) (16.18g, 132.71mmol) dissolved in 300ml of tetrahydrofuran (THF) and 60ml of H ₂ O (N ₂ condition) Pd (PPh ₃ ) ₄ (7.67g, 6.64mmol) and K ₂ CO ₃ (45.85g, 331.77mmol) was added thereto, and the mixture was stirred under reflux for 24 hours. After completion of the reaction, methylene chloride (MC, methylene chloride) was dissolved in the reaction solution, extracted with distilled water, and the organic layer was dried over anhydrous MgSO ₄ , and then the solvent was removed with a rotary evaporator. The compound was purified by chromatography to obtain compound 2-1 (16 g, 45%).

Preparation of compound 2-2

Compound 2-1 (16 g, 59.91 mmol) and zinc cyanide (14.07 g, 119.82 mmol) were dissolved in 160 ml of dimethylformamide (DMF) (N ₂ condition) Pd (PPh ₃ ) ₄ (3.46 g, 3.00 mmol) was added thereto, and the mixture was stirred under reflux for 16 hours. After the reaction was completed, after cooling to room temperature, the obtained solid was filtered and washed with distilled water. The obtained solid was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain compound 2-2 (14 g, 90%).

Preparation of compound 2-3

Compound 2-2 (14 g, 54.20 mmol) was dissolved in 300 ml of benzene, followed by potassium t-buoxide (18.3 g, 186.46 mmol) and acetonitrile (6.68 g, 162.61 mmol) ) Was added and stirred at 20 ° C. When the reaction was completed, ether and 2% NaHCO ₃ were added. After concentration, the resulting compound was recrystallized to obtain compound 2-3 (11 g, 67%).

Preparation of compound 2-4

Compound 2-3 (11 g, 36.75 mmol) and N, N-dimethylbenzamide (6.03 g, 40.42 mmol) were added to 110 ml of POCl ₃ and refluxed. When the reaction was completed, the reactant was added to ice water, and then ammonium hydroxide was added. After extraction with chloroform and distilled water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized to obtain compound 2-4 (10 g, 64%).

Preparation of compound 2

Compound 2-4 (10g, 23.70mmol) and [1,1'-biphenyl] -4-ylboronic acid (5.16g, 26.07mmol) toluene ( Tol) After dissolving in 100ml, 20ml of EtOH, and 20ml of H ₂ O (N ₂ condition), add Pd (PPh ₃ ) ₄ (1.37g, 1.19mmol) and K ₂ CO ₃ (8.19g, 59.26mmol) and reflux for 16 hours. It was stirred. After the reaction was completed, the mixture was cooled to room temperature, solid was generated, filtered, and washed with ethyl acetate (EA, Ethyl acetate) and MeOH. Then, the solid was completely dissolved in an excess of dichloromethane, and then filtered with silica gel to obtain compound 2 (9 g, 70%).

In Preparation Example 1, instead of 2,4-dichloro-6-phenyl-1,3,5-triazine (2,4-dichloro-6-phenyl-1,3,5-triazine), intermediate A in Table 1 below Using, instead of phenylboronic acid (phenylboronic acid) using the intermediate B of Table 1 below, N, N-dimethylbenzamide (N, N-dimethylbenzamide) instead of using the intermediate C of Table 1, [1, 1'-biphenyl] -4-ylboronic acid ([1,1'-biphenyl] -4-ylboronic acid) instead of using the intermediate D in Table 1, the same method as in Preparation Example 1 to prepare the target compound Was synthesized.

< Manufacturing example  2> Synthesis of Compound 902

Preparation of compound 902

In a 250 ml round bottom flask, 0.2 g of Magnesium (0.92 g, 37.81 mmol) and I ₂ 0.2 g were added to THF under nitrogen and refluxed for 2 hours. After cooling to room temperature, 2-chloro-4,6-diphenylpyrimidine (8.53g, 31.99mmol) was dissolved in THF 50ml and slowly added dropwise. After dropwise addition, the mixture was refluxed for 2 hours and cooled to room temperature. 2-([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine (2-([1,1'-) in another 500 ml round bottom flask After dissolving biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine) (10g, 29.09mmol) in 50 ml of THF, the reaction solution was cooled to 0 ° C. The reaction solution was added dropwise while maintaining the temperature at 0 ° C. After the reaction was completed, the reaction was terminated with 4M hydrochloric acid aqueous solution, extracted, and then the organic layer was concentrated under reduced pressure and recrystallized with toluene to obtain compound 902 (9g, 57%).

Compounds other than the compounds described in Production Example 1, Production Example 2, and Table 1 were also prepared in the same manner as described in Production Example.

Tables 2 and 3 below are 1H NMR data and FD-MS data of the synthesized compound, and it can be confirmed that the desired compound was synthesized through the following data.

NO ^One H NMR ( CDCl ₃ , 300Mz ) 2 8.41-8.30 (9H, m), 7.85 (2H, d), 7.75 (2H, d), 7.50-7.41 (12H, m) 8 8.41-8.30 (9H, m), 8.08-7.98 (3H, m), 7.54-7.50 (11H, m), 7.39-7.25 (4H, m) 10 8.41-8.30 (9H, m), 7.98 (1H, d), 7.82 (1H, d), 7.69 (1H, d), 7.57-7.50 (11H, m), 7.39-7.25 (4H, m) 18 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (10H, m), 8.15 (1H, d), 7.70-7.64 (4H, m), 7.52-7.50 (10H, m) 24 8.41-8.35 (7H, m), 7.97-7.96 (4H, d), 7.77 (4H, d), 7.51-7.50 (15H, m) 34 8.41-8.35 (5H, m), 7.96-7.94 (4H, m), 7.75-7.73 (5H, m), 7.61 (1H, d), 7.50-7.41 (12H, m), 7.25 (2H, d) 37 8.41-8.35 (5H, m), 8.08 (1H, d), 7.98-7.96 (3H, m), 7.75-7.74 (3H, m), 7.54-7.31 (15H, m) 51 8.97 (1H, d), 8.41-8.35 (5H, m), 8.15-8.10 (2H, m), 8.00-7.96 (3H, m), 7.75 (2H, d), 7.59-7.41 (11H, m), 7.25 (2H, d) 55 8.41-8.35 (5H, m), 7.96-7.95 (4H, d), 7.82-7.75 (4H, m), 7.50-7.41 (9H, m), 7.25 (2H, d) 60 8.55 (2H, d), 8.41-8.35 (5H, m), 8.19-8.17 (4H, d), 7.96-7.94 (4H, d), 7.75 (2H, d), 7.58-7.35 (16H, m), 7.25-7.16 (6H, m) 63 8.41 (1H, s), 8.30 (2H, d), 7.96 (6H, d), 7.85 (2H, d), 7.75 (8H, d), 7.49-7.41 (12H, m), 7.25 (6H, d) 64 8.41-8.35 (3H, m), 7.96-7.94 (6H, m), 7.75-7.73 (7H, m), 7.61 (1H, d), 7.50-7.41 (12H, m), 7.25 (4H, d) 73 8.55 (1H, d), 8.41-8.35 (3H, m), 8.21-8.19 (2H, m), 7.96-7.94 (5H, m), 7.80-7.35 (19H, m), 7.25-7.16 (6H, m) ) 74 8.55 (1H, d), 8.41-8.35 (3H, m), 7.96-7.92 (6H, m), 7.75-7.70 (5H, m), 7.56-7.41 (11H, m), 7.25 (4H, d) 86 8.87 (1H, d), 8.55 (1H, d), 8.41-8.30 (5H, m), 8.05 (1H, d), 7.96 (5H, d), 7.75 (4H, d), 7.64 (1H, t) , 7.50-7.41 (10H, m), 7.25 (6H, d) 91 8.41-8.35 (6H, m), 7.94 (3H, m), 7.75-7.73 (3H, m), 7.61-7.41 (13H, m) 99 8.41-8.35 (6H, m), 7.98-7.94 (2H, m), 7.82-7.69 (5H, m), 7.61-7.31 (14H, m) 103 8.55 (1H, d), 8.41-8.35 (6H, m), 8.21-8.19 (2H, d), 7.94 (2H, d), 7.80-7.35 (19H, m), 7.20 (2H, q) 106 9.08 (1H, d), 8.84 (1H, d), 8.41-8.35 (6H, m), 8.17 (1H, d), 8.05 (1H, s), 7.94-7.90 (2H, m), 7.75-7.61 ( 8H, m), 7.50-7.41 (9H, m) 111 8.97 (1H, d), 8.41-8.35 (6H, m), 8.25 (1H, d), 8.15-8.10 (2H, m), 8.00-7.94 (2H, m), 7.75-7.73 (3H, m), 7.61-7.41 (12H, m) 126 8.41-8.38 (3H, m), 7.96-7.94 (6H, d), 7.75-7.73 (11H, m), 7.61 (3H, d), 7.49-7.41 (12H, m), 7.25 (2H, d) 132 8.55 (1H, d), 8.41-8.35 (5H, m), 8.19 (1H, d), 7.94-7.91 (7H, m), 7.75-7.73 (6H, m), 7.61-7.35 (15H, m), 7.20-7.16 (2H, q) 142 9.09 (1H, s), 8.49-8.38 (5H, m), 8.16-7.94 (9H, m), 7.75-7.73 (6H, m), 7.61-7.41 (12H, m) 148 9.24 (1H, s), 8.70 (1H, d), 8.59 (1H, s), 8.42-8.35 (5H, m), 7.94 (2H, s), 7.75-7.73 (6H, m), 7.61-7.41 ( 12H, m) 149 9.18-9.14 (4H, m), 8.59-8.55 (3H, m), 8.38-8.35 (4H, m), 7.94 (2H, s), 7.75-7.73 (8H, m), 7.61 (2H, d), 7.50-7.41 (9H, m), 7.23 (2H, t) 152 8.41-8.30 (6H, m), 7.96-7.94 (3H, m), 7.85 (2H, d), 7.75-7.73 (7H, m), 7.61 (1H, d), 7.50-7.41 (12H, m), 7.25 (2H, d) 155 8.41-8.38 (3H, m), 7.96-7.94 (6H, m), 7.75-7.73 (11H, m), 7.61 (3H, d), 7.49-7.41 (12H, m), 7.25 (2H, d) 165 8.55 (1H, d), 8.45-8.30 (8H, m), 7.96-7.93 (4H, m), 7.75-7.70 (6H, m), 7.61-7.41 (12H, m), 7.25 (4H, d) 167 9.08 (2H, d), 8.84 (2H, d), 8.41-8.38 (2H, m), 8.17 (2H, d), 8.05 (2H, s), 7.96-7.90 (5H, m), 7.75-7.62 ( 14H, m), 7.49-7.41 (6H, m), 7.25 (2H, d) 180 8.55 (2H, d), 8.41-8.35 (4H, m), 8.19-8.17 (4H, d), 7.96-7.94 (5H, m), 7.75-7.73 (5H, m), 7.61-7.35 (17H, m ), 7.25-7.16 (6H, m) 183 8.41-8.30 (5H, m), 8.08 (1H, d), 7.98-7.96 (3H, m), 7.88-7.85 (3H, m), 7.75 (4H, d), 7.54-7.25 (15H, m) 184 8.41-8.35 (5H, m), 8.08 (1H, d), 7.98-7.88 (4H, m), 7.75-7.73 (3H, m), 7.61-7.31 (14H, m) 198 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (8H, m), 8.15 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.88 (1H, d) , 7.70-7.64 (4H, tt), 7.54-7.50 (9H, m), 7.39-7.31 (2H, m) 200 8.46 (1H, s), 8.41-8.35 (5H, m), 8.08-7.98 (6H, m), 7.88 (1H, d), 7.61-7.50 (10H, m), 7.39-7.31 (2H, tt) 201 8.97 (1H, d), 8.41-8.35 (5H, m), 8.25 (1H, d), 8.15-7.98 (5H, m), 7.88 (1H, d), 7.59-7.50 (10H, m), 7.39- 7.31 (2H, tt) 219 8.41-8.35 (5H, m), 8.08-7.96 (6H, m), 7.82 (1H, d), 7.69 (1H, d), 7.57-7.50 (10H, m), 7.39-7.25 (6H, m) 222 8.55 (1H, d), 8.41-8.35 (5H, m), 8.19 (1H, d), 8.08-7.91 (10H, m), 7.58-7.50 (10H, m), 7.39-7.16 (7H, m) 225 8.55 (1H, d), 8.45-8.30 (9H, m), 8.08-7.93 (6H, m), 7.70 (1H, t), 7.56-7.49 (10H, m), 7.39-7.25 (6H, m) 233 8.41-8.30 (11H, m), 8.13-7.96 (6H, m), 7.84-7.83 (2H, m), 7.58-7.50 (12H, m), 7.39-7.25 (4H, m) 240 8.55 (2H, d), 8.41-8.35 (5H, m), 8.19-8.17 (4H, d), 8.08-7.94 (7H, m), 7.60-7.50 (13H, m), 7.39-7.16 (10H, m ) 244 8.41-8.35 (5H, m), 7.98-7.94 (3H, m), 7.82-7.69 (5H, m), 7.61-7.39 (14H, m) 246 8.41-8.36 (3H, m), 7.96-7.94 (5H, m), 7.82-7.69 (7H, m), 7.61-7.25 (16H, m) 255 8.55 (1H, d), 8.45-8.30 (9H, m), 7.98-7.93 (2H, dd), 7.82 (1H, d), 7.70-7.69 (2H, m), 7.57-7.49 (10H, m), 7.39-7.25 (4H, m) 260 8.46-8.35 (6H, m), 8.06-7.98 (5H, m), 7.82 (1H, d), 7.69-7.50 (11H, m), 7.39-7.31 (2H, tt) 264 8.41-8.35 (5H, m), 7.98-7.96 (5H, m), 7.82-7.69 (6H, m), 7.57-7.50 (14H, m), 7.39-7.31 (2H, m) 271 8.41-8.35 (5H, m), 7.98-7.94 (5H, m), 7.82 (1H, d), 7.69 (1H, d), 7.57-7.49 (11H, m), 7.39-7.25 (4H, m) 272 8.41-8.30 (7H, m), 7.98-7.96 (3H, m), 7.85-7.69 (6H, m), 7.57-7.25 (15H, m) 276 8.41-8.36 (3H, m), 7.98-7.94 (7H, m), 7.82-7.69 (7H, m), 7.61-7.25 (18H, m) 290 8.46-8.35 (6H, m), 8.06-7.96 (7H, m), 7.82 (1H, d), 7.69-7.50 (11H, m), 7.39-7.25 (4H, m) 293 8.41-8.30 (11H, m), 8.13 (1H, d), 7.98-7.96 (3H, m), 7.84-7.82 (3H, m), 7.69 (1H, d), 7.58-7.50 (12H, m), 7.39-7.25 (4H, m) 338 8.55 (1H, d), 8.41-8.30 (7H, m), 8.15 (1H, d), 8.08-7.91 (8H, m), 7.58-7.50 (10H, m), 7.39-7.16 (7H, m) 348 9.27 (1H, s), 8.79 (1H, d), 8.55 (1H, d), 8.41-8.30 (8H, m), 8.19-8.15 (2H, dd), 7.94-7.91 (5H, m), 7.70- 7.50 (13H, m), 7.35 (1H, t), 7.20-7.16 (2H, tt) 355 8.55 (1H, d), 8.41-8.35 (5H, m), 8.19 (1H, d), 7.95-7.91 (7H, m), 7.82 (2H, d), 7.58-7.50 (8H, m), 7.35 ( 1H, t), 7.20-7.16 (2H, m) 373 8.55 (2H, d), 8.41-8.35 (5H, m), 8.24-8.19 (5H, m), 7.94 (2H, d), 7.80 (1H, d), 7.68-7.50 (14H, m), 7.35 ( 2H, d), 7.20-7.16 (4H, tt) 380 8.55 (1H, d), 8.46-8.35 (6H, m), 8.24-8.19 (3H, m), 8.06-7.94 (5H, m), 7.68-7.50 (12H, m), 7.35 (1H, t), 7.20-7.16 (2H, tt) 384 8.55 (1H, d), 8.41-8.35 (5H, m), 8.21-8.19 (3H, m), 7.97-7.94 (5H, m), 7.77 (4H, m), 7.68 (1H, m), 7.60- 7.50 (15H, m), 7.35 (1H, t), 7.20-7.16 (2H, tt) 399 8.55 (1H, d), 8.45-8.35 (6H, m), 7.98-7.92 (3H, m), 7.82 (1H, d), 7.70-7.69 (2H, m), 7.57-7.49 (10H, m), 7.39-7.31 (2H, tt) 403 8.55 (2H, d), 8.45-8.35 (6H, m), 8.21-8.19 (2H, m), 7.94-7.92 (3H, m), 7.80 (1H, d), 7.70-7.49 (13H, m), 7.35 (1H, t), 7.20-7.16 (2H, tt) 415 8.55 (1H, d), 8.45-8.35 (6H, m), 7.95-7.92 (4H, m), 7.82 (2H, d), 7.70 (1H, t), 7.56-7.49 (8H, m) 425 8.55 (1H, d), 8.45-8.32 (6H, m), 7.96-7.93 (6H, m), 7.75-7.70 (7H, m), 7.61-7.41 (13H, m), 7.25 (2H, d) 430 8.55 (1H, d), 8.45-8.30 (9H, m), 7.98-7.93 (4H, m), 7.82 (1H, d), 7.70-7.69 (2H, m), 7.57-7.49 (10H, m), 7.39-7.25 (6H, m) 440 8.55 (1H, d), 8.46-8.32 (8H, m), 8.06-7.93 (7H, m), 7.70-7.49 (11H, m), 7.25 (2H, d) 454 9.08 (1H, d), 8.84 (1H, d), 8.41-8.35 (5H, m), 8.17 (1H, d), 8.05 (1H, s), 7.94-7.90 (3H, m), 7.75-7.61 ( 8H, m), 7.50-7.41 (9H, m) 459 9.08 (1H, d), 8.84 (1H, d), 8.41-8.35 (5H, m), 8.17 (1H, d), 8.05 (1H, s), 7.98 (1H, d), 7.90 (1H, d) , 7.82 (1H, d), 7.70-7.50 (13H, m), 7.39-7.31 (2H, tt) 479 9.18-9.08 (5H, m), 8.84 (1H, d), 8.59-8.55 (3H, m), 8.36-8.35 (4H, m), 8.17 (1H, d), 8.05 (1H, s), 7.90 ( 1H, d), 7.74-7.62 (6H, m), 7.50 (6H, m), 7.23 (2H, t) 511 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (8H, m), 8.15 (1H, d), 7.94 (2H, d), 7.70-7.49 (14H, m) 512 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (10H, m), 8.15 (1H, d), 7.85 (2H, d), 7.75-7.64 (6H, m), 7.52-7.41 ( 10H, m) 518 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (10H, m), 8.15-7.98 (4H, m), 7.70-7.64 (4H, m), 7.54-7.50 (9H, m), 7.39-7.25 (4H, m) 550 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (12H, m), 7.98-7.94 (2H, m), 7.82 (1H, d), 7.73-7.50 (16H, m), 7.39- 7.25 (4H, m) 561 9.27 (1H, s), 8.97 (1H, d), 8.79 (1H, d), 8.41-8.25 (11H, m), 8.15-8.10 (2H, m), 7.96-7.94 (1H, m), 7.73- 7.50 (15H, m) 564 9.27 (1H, s), 8.79 (1H, d), 8.38-8.33 (10H, m), 7.97-7.94 (5H, m), 7.77-7.61 (10H, m), 7.52-7.50 (13H, m) 574 9.09 (1H, s), 8.49 (1H, d), 8.41-8.35 (5H, m), 8.16 (1H, d), 8.08 (1H, d), 8.00-7.94 (3H, m), 7.75-7.73 ( 3H, m), 7.61-7.41 (12H, m) 582 9.09 (1H, s), 8.55-8.49 (2H, dd), 8.41-8.35 (5H, m), 8.19-8.16 (2H, m), 8.08 (1H, d), 8.00-7.91 (6H, m), 7.61-7.50 (10H, m), 7.35 (1H, t), 7.20-7.16 (2H, tt) 598 9.24 (1H, s), 9.09 (1H, s), 8.70 (1H, d), 8.59 (1H, s), 8.49-8.35 (6H, m), 8.16 (1H, d), 8.08 (1H, d) , 8.00 (1H, d), 7.61-7.50 (9H, m) 604 8.97 (1H, d), 8.41-8.35 (5H, m), 8.25 (1H, d), 8.15-8.10 (2H, m), 8.00-7.94 (3H, m), 7.75-7.73 (3H, m), 7.59-7.41 (12H, m) 606 8.97 (1H, d), 8.41-8.36 (3H, m), 8.25 (1H, d), 8.15-8.10 (2H, m), 8.00-7.94 (5H, m), 7.75-7.73 (5H, m), 7.61-7.41 (12H, m), 7.25 (2H, d) 608 8.97 (1H, d), 8.41-8.25 (8H, m), 8.15-7.98 (6H, m), 7.59-7.50 (10H, m), 7.39-7.25 (4H, m) 645 9.09 (2H, s), 8.55-8.30 (10H, m), 8.16-7.93 (7H, m), 7.70-7.49 (10H, m), 7.25 (2H, d) 650 9.09 (2H, s), 8.49-8.35 (6H, m), 8.16-7.98 (10H, m), 7.61-7.50 (9H, m) 654 9.09 (2H, s), 8.49 (2H, d), 8.41-8.35 (3H, m), 8.16-7.96 (10H, m), 7.77 (4H, m), 7.61-7.50 (13H, m) 681 8.97 (1H, d), 8.41-8.25 (10H, m), 8.15-8.10 (3H, m), 8.00-7.96 (3H, m), 7.84-7.83 (2H, m), 7.59-7.50 (12H, m ) 685 8.41-8.30 (9H, m), 8.13 (1H, d), 7.96-7.95 (4H, m), 7.84-7.82 (4H, m), 7.58-7.50 (10H, m) 690 8.55 (2H, d), 8.41-8.30 (9H, m), 8.19-8.13 (5H, m), 7.96-7.94 (4H, m), 7.84-7.83 (2H, m), 7.60-7.50 (15H, m ), 7.35 (2H, m), 7.20-7.16 (4H, tt) 694 8.41-8.35 (5H, m), 7.97-7.94 (6H, m), 7.77-7.73 (7H, m), 7.61 (1H, d), 7.51-7.41 (15H, m) 708 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (8H, m), 8.15 (1H, d), 7.97-7.96 (4H, s), 7.77-7.64 (8H, m), 7.52- 7.50 (13H, m) 709 9.27 (1H, s), 8.79 (1H, d), 8.41-8.30 (9H, m), 7.97-7.94 (6H, m), 7.77-7.61 (10H, m), 7.52-7.50 (13H, m) 751 8.87 (1H, d), 8.55 (1H, d), 8.41-8.35 (5H, m), 8.05 (1H, d), 7.96-7.94 (5H, m), 7.64-7.49 (11H, m), 7.25 ( 2H, d) 763 8.87 (1H, d), 8.55 (2H, d), 8.41-8.35 (5H, m), 8.21-8.19 (2H, m), 8.05 (1H, d), 7.96-7.94 (4H, m), 7.80 ( 1H, d), 7.68-7.49 (12H, m), 7.35 (1H, t), 7.25-7.16 (4H, m) 768 9.27 (1H, s), 8.87 (1H, d), 8.79 (1H, d), 8.55 (1H, d), 8.41-8.30 (8H, m), 8.15 (1H, d), 8.05 (1H, t) , 7.96 (3H, d), 7.70-7.64 (5H, m), 7.52-7.49 (8H, m), 7.25 (2H, d) 818 9.24 (1H, s), 8.70 (1H, d), 8.42-8.30 (8H, m), 8.08-7.98 (3H, m), 7.57-7.50 (9H, m), 7.39-7.25 (4H, m) 835 9.24 (1H, s), 8.70 (1H, d), 8.42-8.35 (6H, m), 7.95 (2H, d), 7.82 (2H, d), 7.57-7.50 (7H, m) 844 9.18-9.14 (4H, m), 8.55 (2H, d), 8.41-8.35 (5H, m), 7.94 (2H, m), 7.75-7.73 (5H, m), 7.61 (1H, d), 7.50- 7.41 (9H, m), 7.23 (2H, t) 871 8.55 (2H, d), 8.41-8.35 (5H, m), 8.19-8.17 (4H, m), 7.94 (4H, d), 7.60-7.49 (14H, m), 7.35 (2H, t), 7.20- 7.16 (4H, tt) 872 8.55 (2H, d), 8.41-8.30 (7H, m), 8.19-8.17 (4H, m), 7.94 (2H, d), 7.85 (2H, d), 7.75 (2H, d), 7.68-7.35 ( 16H, m), 7.20-7.16 (4H, tt) 890 8.55 (2H, d), 8.46 (1H, s), 8.41-8.35 (5H, m), 8.19-8.17 (4H, m), 8.06-7.94 (6H, m), 7.61-7.50 (13H, m), 7.35 (2H, t), 7.20-7.16 (4H, tt) 902 8.59 (1H, s), 8.28-8.24 (3H, m), 7.79 (4H, d), 7.70 (1H, s), 7.57-7.41 (16H, m)

compound FD-MS compound FD-MS 2 m / z = 539.63 (C37H25N5 = 539.21) 8 m / z = 629.71 (C43H27N5O = 629.22) 10 m / z = 629.71 (C43H27N5O = 629.22) 18 m / z = 613.71 (C43H27N5 = 613.23) 24 m / z = 663.70 (C43H30N5OP = 663.22) 34 m / z = 615.72 (C43H29N5 = 615.24) 51 m / z = 589.69 (C41H27N5 = 589.23) 55 m / z = 564.64 (C38H24N6 = 564.21) 60 m / z = 870.01 (C61H39N7 = 869.33) 63 m / z = 767.92 (C55H37N5 = 767.30) 64 m / z = 691.82 (C49H33N5 = 691.27) 73 m / z = 780.91 (C55H36N6 = 780.30) 74 m / z = 721.87 (C49H31N5S = 721.23) 86 m / z = 742.87 (C52H34N6 = 742.28) 91 m / z = 539.63 (C37H25N5 = 539.21) 99 m / z = 629.71 (C43H27N5O = 629.22) 103 m / z = 704.82 (C49H32N6 = 704.27) 106 m / z = 639.75 (C45H29N5 = 639.24) 111 m / z = 589.69 (C41H27N5 = 589.23) 126 m / z = 767.92 (C55H37N5 = 767.30) 132 m / z = 780.91 (C55H36N6 = 780.30) 142 m / z = 715.84 (C51H33N5 = 715.27) 148 m / z = 616.71 (C42H28N6 = 616.24) 149 m / z = 770.88 (C52H34N8 = 770.29) 152 m / z = 691.82 (C49H33N5 = 691.27) 155 m / z = 767.92 (C55H37N5 = 767.30) 165 m / z = 797.96 (C55H35N5S = 797.26) 167 m / z = 815.96 (C59H37N5 = 815.30) 180 m / z = 946.11 (657H43N7 = 945.36) 183 m / z = 705.80 (C49H31N5O = 705.25) 184 m / z = 629.71 (C43H27N5O = 629.22) 198 m / z = 703.79 (C49H29N5O = 703.24) 200 m / z = 603.67 (C41H25N5O = 603.21) 201 m / z = 603.67 (C41H25N5O = 603.21) 219 m / z = 719.79 (C49H29N5O2 = 719.23) 222 m / z = 794.90 (C55H34N6O = 794.28) 225 m / z = 811.95 (C55H33N5OS = 811.24) 233 m / z = 833.93 (C57H35N7O = 833.29) 240 m / z = 960.09 (C67H41N7O = 959.34) 244 m / z = 629.71 (C43H27N5O = 629.22) 246 m / z = 705.80 (C49H31N5O = 705.25) 255 m / z = 735.85 (C49H29N5OS = 735.21) 260 m / z = 603.67 (C41H25N5O = 603.21) 264 m / z = 753.78 (C49H32N5O2P = 753.23) 271 m / z = 629.71 (C43H27N5O = 629.22) 272 m / z = 705.80 (C49H31N5O = 705.25) 276 m / z = 781.90 (C55H35N5O = 781.28) 290 m / z = 679.77 (C47H29N5O = 679.24) 293 m / z = 833.93 (C57H35N7O = 833.29) 338 m / z = 794.90 (C55H34N6O = 794.28) 348 m / z = 778.90 (C55H34N6 = 778.28) 355 m / z = 653.73 (C44H27N7 = 653.23) 373 m / z = 793.91 (C55H35N7 = 793.30) 380 m / z = 678.78 (C47H30N6 = 678.25) 384 m / z = 828.90 (C55H37N6OP = 828.28) 399 m / z = 659.76 (C43H25N5OS = 659.18) 403 m / z = 734.87 (C49H30N6S = 734.23) 415 m / z = 594.69 (C38H22N6S = 594.16) 425 m / z = 797.96 (C55H35N5S = 797.26) 430 m / z = 811.95 (C55H33N5OS = 811.24) 440 m / z = 685.83 (C47H29N5S = 695.21) 454 m / z = 639.75 (C45H29N5 = 639.24) 459 m / z = 653.73 (C44H27N7 = 653.23) 479 m / z = 718.81 (C48H30N8 = 718.26) 511 m / z = 613.71 (C43H27N5 = 613.23) 512 m / z = 689.80 (C49H31N5 = 689.26) 518 m / z = 779.88 (C55H33N5O = 779.27) 550 m / z = 855.98 (C61H37N5O = 855.30) 561 m / z = 739.86 (C53H33N5 = 739.27) 564 m / z = 889.98 (C61H40N5OP = 889.30) 574 m / z = 589.69 (C41H27N5 = 589.23) 582 m / z = 678.78 (C47H30N6 = 678.25) 598 m / z = 514.58 (C34H22N6 = 514.19) 604 m / z = 589.69 (C41H27N5 = 589.23) 606 m / z = 665.78 (C47H31N5 = 665.26) 608 m / z = 679.77 (C47H29N5O = 679.24) 645 m / z = 745.89 (C51H31N5S = 745.23) 650 m / z = 613.71 (C43H27N5 = 613.23) 654 m / z = 763.82 (C51H34N5OP = 763.25) 681 m / z = 717.82 (C49H31N7 = 717.26) 685 m / z = 692.77 (C46H28N8 = 692.24) 690 m / z = 998.14 (C69H43N9 = 997.36) 694 m / z = 739.80 (C49H34N5OP = 739.25) 708 m / z = 813.88 (C55H36N5OP = 813.27) 709 m / z = 889.98 (C61H40N5OP = 889.30) 751 m / z = 590.67 (C40H26N6 = 590.22) 763 m / z = 755.87 (C52H33N7 = 755.28) 768 m / z = 740.85 (C52H32N6 = 740.27) 818 m / z = 630.70 (C42H26N6O = 630.22) 835 m / z = 489.53 (C31H19N7 = 489.17) 844 m / z = 694.78 (C46H30N8 = 694.26) 871 m / z = 793.91 (C55H35N7 = 793.30) 872 m / z = 870.01 (C61H39N7 = 869,33) 890 m / z = 843.97 (C59H37N7 = 843.31) 902 m / z = 539.63 (C37H25N5 = 539.21)

< Experimental Example  1> -Production of organic light emitting device

After the transparent electrode indium tin oxide (ITO) thin film obtained from glass for OLED (manufactured by Samsung-Corning) is trichloroethylene, acetone, ethanol, distilled water for 5 minutes each, ultrasonic cleaning is performed, and then it is stored in isopropanol. Used.

Next, an 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) triphenyl amine ( 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA) was added.

After evacuating until the vacuum degree in the chamber reached 10 ^-6 torr, a current was applied to the cell to evaporate 2-TNATA to deposit a 600 mm thick hole injection layer 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 to deposit a hole transport layer having a thickness of 300 위에 on the hole injection layer.

After forming the hole injection layer and the hole transport layer, a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, a blue light-emitting host material H1 was vacuum-deposited to a thickness of 200 mm 3 in one cell in the vacuum deposition equipment, and a blue light-emitting dopant material D1 was vacuum-deposited 5% of the host material.

Subsequently, the compound of Table 4 below was deposited as an electron transport layer to a thickness of 300 mm 3.

As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 Å, and an Al cathode was fabricated with a thickness of 1,000 Å.

On the other hand, all the organic compounds required for the production of OLED devices were vacuum sublimated and purified under 10 ^-6 to 10 ^-8 torr for each material, and used for OLED production.

2) Driving voltage and luminous efficiency of the organic light emitting device

The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with the M7000 of the McScience company, and the reference luminance was 700 cd / th through the life measurement equipment (M6000) manufactured by the McScience Company with the measurement results. When m ² , T95 was measured. The results of measuring the driving voltage, luminous efficiency, external quantum efficiency, and color coordinate (CIE) of the white organic light emitting device manufactured according to the present invention are shown in Table 4 below.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Example 1 2 4.38 6.80 (0.134, 0.101) 37 Example 2 8 5.44 6.44 (0.134, 0.102) 32 Example 3 10 4.42 6.78 (0.134, 0.101) 36 Example 4 18 5.38 6.20 (0.134, 0.103) 35 Example 5 24 5.60 6.12 (0.134, 0.102) 34 Example 6 34 5.45 6.01 (0.134, 0.101) 33 Example 7 37 5.44 6.22 (0.134, 0.102) 30 Example 8 51 5.46 6.18 (0.134, 0.101) 29 Example 9 55 5.40 6.13 (0.134, 0.101) 31 Example 10 60 4.40 6.92 (0.134, 0.100) 35 Example 11 63 5.37 6.35 (0.134, 0.101) 32 Example 12 64 5.38 6.41 (0.134, 0.100) 30 Example 13 73 4.81 6.93 (0.134, 0.100) 30 Example 14 74 5.48 6.21 (0.134, 0.100) 32 Example 15 86 5.47 6.28 (0.134, 0.100) 33 Example 16 91 5.45 6.98 (0.134, 0.100) 34 Example 17 99 4.92 5.98 (0.134, 0.102) 31 Example 18 103 5.12 6.20 (0.134, 0.101) 32 Example 19 106 4.89 6.87 (0.134, 0.102) 30 Example 20 111 5.12 6.88 (0.134, 0.100) 34 Example 21 126 5.21 7.00 (0.134, 0.103) 37 Example 22 132 4.38 6.66 (0.134, 0.100) 36 Example 23 142 5.40 6.36 (0.134, 0.102) 32 Example 24 148 5.42 6.26 (0.134, 0.101) 48 Example 25 149 5.39 6.19 (0.134, 0.100) 31 Example 26 152 5.55 6.27 (0.134, 0.102) 31 Example 27 155 4.98 6.20 (0.134, 0.103) 30 Example 28 165 5.41 6.19 (0.134, 0.100) 32 Example 29 167 5.22 6.28 (0.134, 0.103) 36 Example 30 180 5.19 6.41 (0.134, 0.102) 33 Example 31 183 5.43 6.17 (0.134, 0.100) 30 Example 32 184 4.94 6.85 (0.134, 0.099) 31 Example 33 198 5.92 6.87 (0.134, 0.102) 34 Example 34 200 4.98 7.03 (0.134, 0.100) 35 Example 35 201 5.00 6.21 (0.134, 0.103) 32 Example 36 219 4.93 6.35 (0.134, 0.101) 35 Example 37 222 4.74 6.92 (0.134, 0.104) 36 Example 38 225 5.03 6.27 (0.134, 0.100) 35 Example 39 233 5.11 6.22 (0.134, 0.103) 36 Example 40 240 5.38 6.20 (0.134, 0.102) 32 Example 41 244 5.60 6.12 (0.134, 0.101) 35 Example 42 246 5.45 6.01 (0.134, 0.102) 31 Example 43 255 5.44 6.22 (0.134, 0.100) 30 Example 44 260 5.46 6.18 (0.134, 0.103) 33 Example 45 264 5.40 6.13 (0.134, 0.100) 52 Example 46 271 5.19 6.11 (0.134, 0.100) 35 Example 47 272 5.21 6.31 (0.134, 0.103) 32 Example 48 276 5.19 6.41 (0.134, 0.102) 33 Example 49 290 5.43 6.17 (0.134, 0.100) 31 Example 50 293 4.94 6.85 (0.134, 0.099) 40 Example 51 338 4.51 6.87 (0.134, 0.102) 38 Example 52 348 4.45 7.03 (0.134, 0.100) 35 Example 53 355 5.00 6.21 (0.134, 0.103) 32 Example 54 373 4.46 7.03 (0.134, 0.101) 34 Example 55 380 4.50 6.92 (0.134, 0.104) 36 Example 56 384 4.52 6.44 (0.134, 0.100) 44 Example 57 399 5.11 6.22 (0.134, 0.103) 36 Example 58 403 5.46 6.18 (0.134, 0.103) 33 Example 59 415 5.40 6.13 (0.134, 0.100) 37 Example 60 425 5.19 6.11 (0.134, 0.100) 35 Example 61 430 5.21 6.31 (0.134, 0.103) 32 Example 62 440 5.19 6.41 (0.134, 0.102) 33 Example 63 454 5.43 6.17 (0.134, 0.100) 31 Example 64 459 5.12 6.20 (0.134, 0.101) 37 Example 65 479 4.87 6.87 (0.134, 0.102) 32 Example 66 511 5.39 6.88 (0.134, 0.100) 34 Example 67 512 4.47 7.00 (0.134, 0.103) 35 Example 68 518 5.34 6.31 (0.134, 0.100) 33 Example 69 550 5.40 6.36 (0.134, 0.102) 32 Example 70 561 5.42 6.26 (0.134, 0.101) 32 Example 71 564 5.39 6.19 (0.134, 0.100) 52 Example 72 574 5.55 6.27 (0.134, 0.102) 31 Example 73 582 4.98 6.20 (0.134, 0.103) 30 Example 74 598 5.41 6.19 (0.134, 0.100) 32 Example 75 604 4.62 6.52 (0.134, 0.103) 36 Example 76 606 5.43 6.17 (0.134, 0.100) 31 Example 77 608 5.12 6.20 (0.134, 0.101) 37 Example 78 645 4.87 6.87 (0.134, 0.102) 32 Example 79 650 5.50 6.32 (0.134, 0.101) 33 Example 80 654 5.44 6.44 (0.134, 0.102) 47 Example 81 681 5.34 6.38 (0.134, 0.101) 31 Example 82 685 5.38 6.20 (0.134, 0.103) 35 Example 83 690 5.60 6.12 (0.134, 0.102) 34 Example 84 694 5.45 6.01 (0.134, 0.101) 33 Example 85 708 5.44 6.22 (0.134, 0.102) 30 Example 86 709 5.46 6.18 (0.134, 0.101) 41 Example 87 751 5.40 6.13 (0.134, 0.101) 31 Example 88 763 5.44 6.30 (0.134, 0.100) 32 Example 89 768 5.37 6.35 (0.134, 0.101) 32 Example 90 818 5.38 6.41 (0.134, 0.100) 30 Example 91 835 4.81 6.93 (0.134, 0.100) 30 Example 92 844 5.48 6.21 (0.134, 0.100) 31 Example 93 871 5.47 6.28 (0.134, 0.100) 33 Example 94 872 4.45 6.98 (0.134, 0.100) 36 Example 95 890 4.52 6.63 (0.134, 0.102) 31 Example 96 902 5.49 6.11 (0.134, 0.100) 32 Comparative Example 1-1 E1 5.56 5.91 (0.134, 0.100) 28 Comparative Example 1-2 BBQB 5.50 6.10 (0.134, 0.101) 30 Comparative Example 1-3 TBQB 5.51 6.15 (0.134, 0.102) 29 Comparative Example 1-4 E2 5.43 5.50 (0.133, 0.106) 25 Comparative Example 1-5 E3 5.52 6.08 (0.133, 0.101) 13 Comparative Example 1-6 E4 5.52 5.99 (0.132, 0.102) 29

As can be seen from the results of Table 4, the organic light-emitting device using the electron transport layer material of the blue organic light-emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and life compared to Comparative Example 1-1. In particular, it was confirmed that the compounds 2, 10, 60, 132, 373, 384, 512, 604, and 872 were excellent in all aspects of driving, efficiency, and life.

The cause of these results is that when an invented compound with suitable length, strength and flat properties is used as an electron transport layer, it receives electrons under certain conditions to make the compound in an excited state, and in particular, the excited state of the heteroskeleton site of the compound. When is formed, it is judged that the excited energy is transferred to a stable state before the excited heteroskeleton site reacts, and the relatively stable compound can efficiently transfer electrons without decomposition or destruction of the compound. For reference, it is believed that those that have a stable state when excited are aryl or assenic compounds or polycyclic hetero compounds. therefore. It is judged that the compounds of the present invention have improved electron-transporting properties or improved stability, thereby bringing about superiority in all aspects of driving, efficiency, and lifetime.

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

Claims (13)

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

In Chemical Formula 1,
X ₁ to X ₃ are the same as or different from each other, and each independently, CRa; Or N,
At least one of X ₁ to X ₃ is N,
Ra is hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; and -P (= O) RR ',
L ₁ to L ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Z ₁ to Z ₄ are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR ',
m, n, p and q are integers from 1 to 5, and when m, n, p and q are each 2 or more, the substituents in parentheses are the same or different from each other,
R, R 'and R "are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. The method according to claim 1, "Substituted or unsubstituted" is C1 to C60 straight or branched chain alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched chain alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R "; -P (= O) RR '; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine Means substituted or unsubstituted with one or more substituents, or substituted or unsubstituted with two or more substituents selected from the substituents exemplified above,
The definition of R, R 'and R "is the same heterocyclic compound as the definition in the formula (1). The method according to claim 1,
Formula 1 is a heterocyclic compound represented by any one of the following formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,
L ₁ to L ₄ , Z ₁ to Z ₄ , m, n, p, q, X ₂ and X ₃ are the same as defined in Chemical Formula 1 above. The method according to claim 1,
Formula 1 is a heterocyclic compound represented by any one of the following formulas 5 to 7:
[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 5 to 7,
L ₃ , L ₄ , Z ₁ to Z ₄ , m, n, p, q, X ₁ to X ₃ are the same as defined in Chemical Formula 1,
L ₂₂ is a substituted or unsubstituted polycyclic arylene group; Or a substituted or unsubstituted heteroarylene group,
L ₃₁ and L ₃₂ is the same as or different from each other, and each independently a substituted or unsubstituted polycyclic arylene group,
Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -CN; -SiRR'R "; and -P (= O) RR '. The method according to claim 1,
L ₁ to L ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group. The method according to claim 1,
Z ₁ to Z ₄ are the same as or different from each other, and each independently, hydrogen; A substituted or unsubstituted C6 to C40 aryl group; A substituted or unsubstituted C2 to C40 heteroaryl group; -CN; And -P (= O) RR '. The method according to claim 1, wherein Formula 1 is a heterocyclic compound represented by any one of the following compounds:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the heterocyclic compound according to any one of claims 1 to 7. Phosphorus organic light emitting device. The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound. The organic light emitting device of claim 8, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer includes the heterocyclic compound. The organic light emitting device of claim 8, wherein the organic material layer includes an electron transport layer, and the electron transport layer includes the heterocyclic compound. The organic light emitting device of claim 8, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or a hole blocking layer includes the heterocyclic compound. The method according to claim 8, The organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. An organic light emitting device further comprising 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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