KR20200078255A - Heterocyclic Compound and Organic Light Emitting Device Comprising The Same - Google Patents

Abstract

The present invention provides a heterocyclic compound represented by chemical formula 1 and an organic light emitting device including the same. It is possible to improve quantum efficiency.

Description

Heterocyclic Compound and Organic Light Emitting Device Comprising The Same}

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

The organic light emitting diode (OLED) is a self-emission type device, and has a wide viewing angle, excellent contrast, a fast response time, excellent luminance, driving voltage, and response speed characteristics, and is capable of multicolorization. A typical organic light-emitting diode may include an anode and a cathode and an organic layer interposed between the anode and the cathode. The organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole transport layer, and electrons injected from the cathode move to the light emitting layer via the electron transport layer. Carriers, such as holes and electrons, recombine in the light emitting layer region to generate excitons. As the excitons change to the ground state, light is generated.

In general, excitons generated when driving an organic light-emitting diode are randomly generated with a singlet state of 25% and triplet state of 75%. In the case of a fluorescent material, 25% of the singlet state is caused by excitons. Only luminescence is generated so that the internal quantum efficiency stays at the maximum level of 25%. In order to improve these properties, iridium or platinum complexes that can use triplet energy are used, and it is known to possess excellent quantum efficiency properties. However, these materials are expensive, and their application is limited due to the instability of the blue light emitting material.

Conventional thermally activated delayed fluorescence organic materials (Thermally Activated Delayed Fluorescence, TDAF) have a difference between singlet and triplet states of excitons of 0.3 eV or less, which corresponds to room temperature or device driving temperature. By transferring the triplet state to the singlet state by heat, theoretically, a quantum efficiency of 100% can be exhibited. However, there is a problem in that the actual quantum efficiency is very different from the above theoretical quantum efficiency.

Korean Patent Publication No. 2010-0082986

The problem to be solved by the present invention is a thermally active delayed fluorescence material capable of improving actual quantum efficiency as energy transfer is more efficiently possible from a triplet state to a singlet state. , TDAF) and an organic light emitting device including the same.

One embodiment of the present invention provides a heterocyclic compound represented by Formula 1 below:

[Formula 1]

In Chemical Formula 1,

X1 to X3 are the same or different from each other, each independently N or CR, and at least two of X1 to X3 are N,

R1 is an aryl group unsubstituted or substituted with a cyano group,

R2 is hydrogen; heavy hydrogen; Cyano group; Or an aryl group unsubstituted or substituted with a cyano group,

R and R3 are the same or different from each other, and independently are hydrogen or deuterium,

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heteroaryl group,

a is an integer of 1 to 4, and when a is 2 or more, R2 is the same or different from each other,

b is an integer of 1 to 3, and when b is 2 or more, R3 is the same or different from each other.

In addition, another embodiment of the present invention, the first electrode, the second electrode and an organic material layer between the first electrode and the second electrode, the organic material layer is an organic compound containing a heterocyclic compound represented by the formula (1) A light emitting device is provided.

The heterocyclic compound of the present invention can improve the actual quantum efficiency as it is possible to more efficiently transfer energy from a triplet state to a singlet state, so it is suitable as a thermally active delayed fluorescent material (TDAF). Can be used.

Further, the heterocyclic compound of the present invention can be used as a hole injection material, a hole transport material, a host material, an electron injection material, or an electron transport material by being included in one or more organic material layers in an organic light emitting device. The organic light emitting device using the same has excellent electrochemical and thermal stability, and thus has excellent life characteristics, and has a high luminous efficiency even at a low driving voltage.

1 is a schematic view showing a stacked structure of an organic light emitting device according to an embodiment of the present invention.
2 is a view schematically showing a stacked structure of an organic light emitting device according to another embodiment of the present invention.
3 is a view schematically showing a stacked structure of an organic light emitting device according to another embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

In the present specification, "substituted or unsubstituted" means deuterium, halogen group, hydroxyl group; Cyano group (CN), nitro group, C ₁ to C ₆₀ alkyl group, C ₂ to C ₆₀ alkenyl group, C ₂ to C ₆₀ alkynyl group, C ₃ to C ₆₀ cycloalkyl group, C ₂ to C ₆₀ Heterocycloalkyl group, C ₆ to C ₆₀ aryl group, C ₂ to C ₆₀ heteroaryl group, C ₁ to C ₆₀ alkylamine group, C ₆ to C ₆₀ arylamine group, and C ₂ to C ₆₀ Substituted or unsubstituted with one or more substituents selected from the group consisting of heteroarylamine groups, substituted or unsubstituted with two or more of the substituents attached, or substituted or unsubstituted with two or more substituents selected from the substituents Means For example, "substituent to which two or more substituents are connected" may be a 9-phenylcarbazolyl group. That is, the 9-phenylcarbazolyl group may be a heteroaryl group, or may be interpreted as a substituent to which a phenyl group and a carbazolyl group are connected. The additional substituents may be further substituted.

The "substituted or unsubstituted" is deuterium, halogen group, hydroxyl group, cyano group, nitro group, C ₁ to C ₆₀ straight or branched chain alkyl group, C ₆ to C ₆₀ aryl group, C ₂ to C ₆₀ It may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group, C ₆ to C ₆₀ arylamine group, and C ₂ to C ₆₀ heteroarylamine group.

The "substituted or unsubstituted" is deuterium, halogen group, hydroxyl group, cyano group, nitro group, C ₁ to C ₃₀ straight or branched chain alkyl group, C ₆ to C ₃₀ aryl group, and C ₂ to C It may be unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heteroaryl groups.

The "substituted or unsubstituted" is deuterium, halogen group, hydroxyl group, cyano group, nitro group, C ₁ to C ₁₀ straight or branched chain alkyl group, C ₆ to C ₁₈ aryl group, and C ₂ to C It may be unsubstituted or substituted with one or more substituents selected from the group consisting of ₁₈ heteroaryl groups.

The "substituted or unsubstituted" is deuterium, halogen group, hydroxyl group, cyano group, nitro group, 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-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl Practical group, 1-methylpentyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, carbazolyl group and dibenzofue It may be substituted or unsubstituted with one or more substituents selected from the group consisting of a ranyl group.

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 is substitutable, 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 group may be a fluorine group, a chlorine group, a bromine group, or an iodine group.

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 or unsubstituted by other substituents. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 30 carbon atoms, and more specifically 1 to 10 carbon atoms. Specific examples of the alkyl group 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-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl 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 Tyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethylpropyl group, 1,1-dimethylpropyl group, isohexyl 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 or unsubstituted by other substituents. Carbon number of the alkenyl group may be 2 to 60, specifically 2 to 30, more specifically, 2 to 20. Specific examples of the alkenyl group include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3 -Methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2 -Phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, and the like. It is not limited.

In the present specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted or unsubstituted by other substituents. Carbon number of the alkynyl group may be 2 to 60, specifically 2 to 30, more specifically, 2 to 20.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted or unsubstituted 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 cyclic group may be a cycloalkyl group, but may be another kind 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 30 carbon atoms, and more specifically 5 to 20 carbon atoms. Specific examples of the cycloalkyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methyl Cyclohexyl 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, and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted or unsubstituted by other substituents. have. 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 kind of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 30 carbon atoms, and more specifically 3 to 18 carbon atoms.

In the present specification, the aryl group includes 6 to 60 carbon atoms or a monocyclic ring, and may be further substituted or unsubstituted 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 kind of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 30 carbon atoms, and more specifically 6 to 18 carbon atoms. Specific examples of the aryl group include a phenyl group, biphenyl group, triphenyl group, naphthyl group, anthracenyl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyre group 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 is not limited thereto.

In the present specification, the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, and includes monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted or unsubstituted 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 30 carbon atoms, and more specifically 3 to 18 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, naphthyridinyl group, acridinyl group, phenanthridinyl group, diaza Naphthalenyl group, triazaindenyl group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuranyl group, dibenzothiophene group, dibenzo Furanyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, imidazopyridinyl group, dibenzosilol group, spirobi (dibenzosilol), Dihydrophenazinyl group, phenoxazinyl group, phenanthridinyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11- Dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthyridinyl 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, or 5,11-dihydroindeno[1,2-b]cover Sleepy groups 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 groups; Alkyl heteroarylamine groups; And aryl heteroarylamine group may include at least one selected from the group consisting of, wherein the alkyl, aryl, heteroaryl may be applied to the content of the above-described alkyl group, aryl group, heteroaryl group. 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, terphenylamine group, biphenylphenylamine group, phenylterphenylamine group, biphenylterphenylamine group, naphthylphenylamine group, dinaphthylamine group, biphenyl It may be a naphthylamine group, a naphthyl terphenylamine group, a ditolylamine group, or a phenyltolylamine group, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more of the aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including the two or more heterocyclic groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously. The heteroaryl group in the heteroarylamine group may be selected from examples of the heteroaryl group described above.

The heterocyclic compound of the present invention may be represented by Formula 1 above.

In particular, in the heterocyclic compound of the present invention, electron-donor substituents Y1 and Y2 are substituted on the N-containing benzene ring of Formula 1, and at least one electron acceptor substituent R1 or R2 of the carbazolyl group of Formula 1 When combined, when used as a thermally active delayed fluorescent material (TDAF), the actual quantum efficiency is theoretical quantum efficiency (100) as it becomes possible to more efficiently transfer energy from triplet to singlet. %).

In addition, when the electron acceptor substituent (Y1) is substituted at position 1 or 8 of the carbazole ring in Chemical Formula 1, structural steric hindrance increases, and HOMO and LUMO are well separated, thereby reducing ΔEST value and causing heat. As an active delayed fluorescent material (TADF), efficiency characteristics and voltage characteristics are excellent.

The X1 to X3 are the same or different from each other, each independently N or CR, and at least two of X1 to X3 may be N. As described above, when the heterocyclic compound represented by Formula 1 has a pyrimidine having 2 N or a triazine ring having 3 N among X1 to X3, it is generally organic light-emitting compared to having a pyridine ring having 1 N. It has the effect of lowering the driving voltage of the device.

Two of X1 to X3 may be N, and the other may be CR.

All of X1 to X3 may be N.

The Chemical Formula 1 may be represented by any one selected from the following Chemical Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Chemical Formulas 2-1 to 2-4, X1 to X3, R1 to R3, Y1, Y2, a and b are as defined in Chemical Formula 1.

The R may be hydrogen or deuterium.

R may be hydrogen.

The R3 may be hydrogen or deuterium.

R3 may be hydrogen.

The R1 may be an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a cyano group.

The R1 may be an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group.

The R1 may be an aryl group having 6 to 18 carbon atoms unsubstituted or substituted with a cyano group.

R1 is a phenyl group unsubstituted or substituted with a cyano group; A biphenyl group unsubstituted or substituted with a cyano group; A triphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; An anthracenyl group unsubstituted or substituted with a cyano group; A chrysenyl group unsubstituted or substituted with a cyano group; A phenanthrenyl group unsubstituted or substituted with a cyano group; A perylenyl group unsubstituted or substituted with a cyano group; A fluoranthenyl group unsubstituted or substituted with a cyano group; A triphenylenyl group unsubstituted or substituted with a cyano group; A phenenyl group unsubstituted or substituted with a cyano group; A pyrenyl group unsubstituted or substituted with a cyano group; A tetrasenyl group unsubstituted or substituted with a cyano group; A pentacene group unsubstituted or substituted with a cyano group; A fluorenyl group unsubstituted or substituted with a cyano group; An indenyl group unsubstituted or substituted with a cyano group; An acenaphthylenyl group unsubstituted or substituted with a cyano group; A benzofluorenyl group unsubstituted or substituted with a cyano group; A spirobifluorenyl group unsubstituted or substituted with a cyano group; Or it may be a 2,3-dihydro-1H-indenyl group unsubstituted or substituted with a cyano group.

R1 is a phenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; A biphenyl group unsubstituted or substituted with a cyano group; A terphenyl group unsubstituted or substituted with a cyano group; Or it may be a phenanthrenyl group unsubstituted or substituted with a cyano group.

The R1 may be a phenyl group unsubstituted or substituted with a cyano group.

R1 may be a phenyl group substituted with a cyano group.

The R1 may be represented by any one selected from the following formulas R-1 to R-3.

[Formula R-1]

[Formula R-2]

[Formula R-3]

는 상기 화학식 1로 표시되는 헤테로고리 화합물에 치환되는 위치를 나타낸다.In the formulas R-1 to R-3,

Represents a position substituted with the heterocyclic compound represented by Formula 1 above.

The Chemical Formula 1 may be represented by at least one selected from the following Chemical Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Chemical Formulas 2-1 to 2-4,

X1 to X3, R1 to R3, a, b, Y1 and Y2 are as defined in Chemical Formula 1.

R2 is hydrogen; heavy hydrogen; Cyano group; Or it may be an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a cyano group.

R2 is hydrogen; heavy hydrogen; Cyano group; Or it may be an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group.

R2 is hydrogen; heavy hydrogen; Cyano group; Or it may be an aryl group having 6 to 18 carbon atoms unsubstituted or substituted with a cyano group.

R2 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a cyano group; A biphenyl group unsubstituted or substituted with a cyano group; A triphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; An anthracenyl group unsubstituted or substituted with a cyano group; A chrysenyl group unsubstituted or substituted with a cyano group; A phenanthrenyl group unsubstituted or substituted with a cyano group; A perylenyl group unsubstituted or substituted with a cyano group; A fluoranthenyl group unsubstituted or substituted with a cyano group; A triphenylenyl group unsubstituted or substituted with a cyano group; A phenenyl group unsubstituted or substituted with a cyano group; A pyrenyl group unsubstituted or substituted with a cyano group; A tetrasenyl group unsubstituted or substituted with a cyano group; A pentacene group unsubstituted or substituted with a cyano group; A fluorenyl group unsubstituted or substituted with a cyano group; An indenyl group unsubstituted or substituted with a cyano group; An acenaphthylenyl group unsubstituted or substituted with a cyano group; A benzofluorenyl group unsubstituted or substituted with a cyano group; A spirobifluorenyl group unsubstituted or substituted with a cyano group; Or it may be a 2,3-dihydro-1H-indenyl group unsubstituted or substituted with a cyano group.

R2 is hydrogen; heavy hydrogen; Cyano group; A phenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; A biphenyl group unsubstituted or substituted with a cyano group; A terphenyl group unsubstituted or substituted with a cyano group; Or it may be a phenanthrenyl group unsubstituted or substituted with a cyano group.

R2 is hydrogen; heavy hydrogen; Cyano group; Or it may be a phenyl group unsubstituted or substituted with a cyano group.

R2 is hydrogen; heavy hydrogen; Cyano group; Or it may be a phenyl group substituted with a cyano group.

The phenyl group substituted with the cyano group may be represented by any one selected from the formulas R-1 to R-3.

Y1 and Y2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

Y1 and Y2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 18 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted arylamine group; Or it may be a substituted or unsubstituted heteroaryl group containing 2 to 18 carbon atoms or O.

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted pyrimidyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted acridil group; A substituted or unsubstituted phenoxazinyl group; Or it may be a substituted or unsubstituted dibenzofuranyl group.

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted pyrimidyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted acridil group; A substituted or unsubstituted phenoxazinyl group; Or it may be a substituted or unsubstituted dibenzofuranyl group.

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted arylamine group; A heteroaryl group containing 2 to 18 carbon atoms; Or a substituted or unsubstituted dibenzofuranyl group.

Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or it may be a substituted or unsubstituted heteroaryl group, wherein the aryl group, arylamine group and heteroaryl group is a halogen group, hydroxyl group, cyano group, nitro group, 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-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group , Neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, phenyl group, biphenyl group, triphenyl group, naphthyl group, anthracenyl group, chrysenyl group, phenanthrenyl group, perylenyl group , Fluoranthenyl group, triphenylenyl group, phenenyl group, pyrenyl group, tetrasenyl group, pentasenyl group, fluorenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, carbazolyl group and dibenzofu It may be substituted with at least one substituent selected from the group consisting of a ranyl group, but is not limited thereto.

Y1 and Y2 are the same as or different from each other, and each independently a phenyl group; A carbazolyl group unsubstituted or substituted with a phenyl group; An acridil group unsubstituted or substituted with a methyl group; Phenoxazinyl group; Or it may be a dibenzofuranyl group.

Y1 and Y2 are the same as or different from each other, and are each independently selected from the following structural formulas.

는 상기 Y1 및 Y2가 상기 화학식 1로 표시되는 헤테로고리 화합물에 치환되는 위치를 나타낸다.In the above structural formula,

Indicates a position where Y1 and Y2 are substituted with the heterocyclic compound represented by Chemical Formula 1 above.

Formula 1 may be represented by any one selected from the following compounds, but is not limited thereto.

In addition, by introducing various substituents to the heterocyclic compound represented by the formula (1), it is possible to synthesize a compound having the inherent properties of the introduced substituent. For example, a hole injection layer material, a hole transport material, a light emitting layer material, a hole blocking layer material, an electron transport layer material, or a electron transport layer material used in the manufacture of an organic light emitting device is introduced into the core structure by introducing a substituent, which is mainly used in each organic material layer. Materials can be synthesized that meet the required conditions.

In addition, the energy band gap can be finely controlled by introducing various substituents to the heterocyclic compound represented by Chemical Formula 1, and on the other hand, by improving the interfacial properties between the organic material layers, the use of the heterocyclic compound can be varied. have.

Meanwhile, the heterocyclic compound represented by Chemical Formula 1 has a high glass transition temperature (Tg) and excellent thermal stability. Such an increase in thermal stability may be an important factor providing driving stability to the organic light emitting device.

The heterocyclic compound of the present invention can be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and heterocyclic compounds represented by Formula 1 may be prepared from the intermediate compounds.

In addition, the present invention provides an organic light emitting device comprising a heterocyclic compound represented by the formula (1).

Specifically, the organic light emitting device includes a first electrode, a second electrode, and an organic material layer provided between the first electrode and the second electrode, and the organic material layer may include a heterocyclic compound represented by Chemical Formula 1 have.

The organic light-emitting device may be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic material layer is formed using the aforementioned heterocyclic compound.

The heterocyclic compound represented by Chemical Formula 1 may be formed as 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. For example, when the heterocyclic compound represented by the formula (1) is used as a material for a hole injection layer, a hole transport layer, a light emitting layer (host or dopant), a hole blocking layer, an electron transport layer or an electron injection layer, an organic material layer using a solution coating method Formation is possible.

As another example, when forming an organic material layer with the heterocyclic compound represented by the formula (1), the organic material layer thereunder is formed by a solution coating method, the organic material layer containing the heterocyclic compound represented by the formula (1) is vacuum deposition method It can also be formed using. Specifically, when the heterocyclic compound represented by Chemical Formula 1 is used as a material for a hole blocking layer, an electron transporting layer, or an electron injection layer, a light emitting layer is formed on the first electrode, or a hole injection layer and/or on the first electrode When forming the hole transport layer and the light emitting layer, a solution coating method may be used, and an organic material layer including the heterocyclic compound represented by Chemical Formula 1 may be formed thereon using a vacuum deposition method. In this case, even though the organic material layer containing the heterocyclic compound represented by Chemical Formula 1 was prepared by a vacuum deposition method, it is well matched with the organic material layer formed by a solution coating method under the organic material layer.

The organic light emitting device includes at least one of a hole injection layer, a hole transport layer, a light emitting layer (host or dopant), a hole blocking layer, an electron injection layer, and an electron transport layer as an organic material layer, and such a hole injection layer, a hole transport layer, and a light emitting layer (host) Or a dopant), a hole blocking layer, an electron injection layer and at least one of the electron transport layer may include a heterocyclic compound represented by the formula (1).

In addition, the organic light emitting device may include a light emitting layer as an organic material layer, and the dopant material of the light emitting layer may include a heterocyclic compound represented by Chemical Formula 1. The emission layer including the heterocyclic compound represented by Chemical Formula 1 may be a green emission layer.

When the heterocyclic compound represented by Chemical Formula 1 is included in the host of the light emitting layer, the light emitting layer may further include a dopant. Specifically, the heterocyclic compound represented by Chemical Formula 1 may be used as a p-type phosphorescent host or an n-type phosphorescent host.

The dopant that can be used together with the heterocyclic compound represented by Formula 1 may be used without limitation as long as it is known in the art. For example, when the heterocyclic compound represented by Chemical Formula 1 is used as a phosphorescent host, tris(2-phenylpyridine)iridium(III)(Ir(ppy) ₃ ), bis[2-(4, 6-difluorophenyl)pyridinato-C ² , N](picolinato) iridium(III) (FIrpic), platinum(II)octaethylporphyrin (PtOEP), TBE002 (Cobion) However, it is not limited thereto.

1 illustrates a stacking order of organic light emitting devices according to an embodiment of the present invention. According to FIG. 1, a first electrode, a light emitting layer, and a second electrode may be sequentially stacked on a substrate. The light-emitting layer may include a heterocyclic compound represented by the formula (1).

2 shows a stacking order of the organic light emitting devices according to another embodiment of the present invention. According to FIG. 2, a first electrode, a light emitting layer, an electron transport layer, and a second electrode may be sequentially stacked on a substrate. A heterocyclic compound represented by Chemical Formula 1 may be included in at least one of the light emitting layer and the electron transport layer.

In addition, the stacking order of the organic light emitting device according to another embodiment of the present invention is shown in FIG. 3. According to FIG. 3, a first electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a second electrode may be sequentially stacked on a substrate. A heterocyclic compound represented by Chemical Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer.

Although the stacked structure of the organic light emitting device according to an embodiment of the present invention is shown in FIGS. 1 to 3 as described above, the scope of the present invention is not intended to be limited by the FIGS. 1 to 3, and is known in the art. The structure of the organic light emitting device can be applied to the present invention.

Specifically, the organic light emitting device includes: a substrate/first electrode/light emitting layer/second electrode; A substrate/first electrode/hole injection layer/light emitting layer/second electrode; A substrate/first electrode/hole transport layer/light emitting layer/second electrode; A substrate/first electrode/hole injection layer/hole transport layer/light emitting layer/second electrode; A substrate/first electrode/light emitting layer/electron transport layer/second electrode; A substrate/first electrode/light emitting layer/electron injection layer/second electrode; A substrate/first electrode/light emitting layer/hole blocking layer/second electrode; A substrate/first electrode/light emitting layer/electron transport layer/electron injection layer/second electrode; A substrate/first electrode/light emitting layer/hole blocking layer/electron transport layer/second electrode; A substrate/first electrode/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/second electrode; A substrate/first electrode/hole injection layer/light emitting layer/electron transport layer/second electrode; A substrate/first electrode/hole injection layer/light emitting layer/electron injection layer/second electrode; A substrate/first electrode/hole injection layer/light emitting layer/electron transport layer/electron injection layer/second electrode; A substrate/first electrode/hole transport layer/light emitting layer/electron transport layer/second electrode; A substrate/first electrode/hole transport layer/light emitting layer/electron injection layer/second electrode; A substrate/first electrode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/second electrode; A substrate/first electrode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/second electrode; A substrate/first electrode/hole injection layer/hole transport layer/light emitting layer/electron injection layer/second electrode; It may have a structure of a substrate/first electrode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/second electrode, etc., wherein at least one layer of organic material between the first electrode and the second electrode, such as hole The injection layer, the hole transport layer, the emission layer, the hole blocking layer, the electron transport layer, or the electron injection layer may include a heterocyclic compound represented by Chemical Formula 1 above. More specifically, the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a light emitting layer or an electron transport layer in a stacked structure of the organic light emitting device as described above.

The organic light emitting device according to the present specification may be manufactured by materials and methods known in the art, except that the heterocyclic compound represented by Chemical Formula 1 is included in at least one layer of the organic material layer.

The heterocyclic compound represented by Chemical Formula 1 may independently constitute one or more layers of the organic material layer of the organic light emitting device. However, if necessary, an organic material layer may be formed by mixing with other materials.

In the organic light emitting device, materials other than the heterocyclic compound represented by Chemical Formula 1 are exemplified below, but these are for illustration only, and are not intended to limit the scope of the present invention. Materials known in the art Can be replaced with

According to an embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode. According to another embodiment of the present invention, the first electrode may be a cathode, and the second electrode may be an anode.

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 anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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, or polyaniline, but is 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 cathode 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 described in Advanced Material, 6, p.677 (1994). Starburst amine derivatives, such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenyl Amine (2-TNATA; 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine), a polyaniline/dodecylbenzenesulfonic acid (Polyaniline/Dodecylbenzenesulfonic acid) or poly(3, 4-Ethylenedioxythiophene)/Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), Polyaniline/Camphor sulfonic acid, Polyaniline/Poly( 4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)), N,N''-di(1-naphthyl)-N,N''-diphenyl-(1,1''-ratio Phenyl)-4,4′'-diamine (N,N′-Di(1-naphthyl)-N,N′'-diphenyl-(1,1′'-biphenyl)-4,4′'-diamine, NPB ), or 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, HAT-CN).

As the hole transport material, a pyrazoline derivative, an arylamine-based derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, specifically α-NPD(N, N'-Bis(naphthalen-1-yl)-N, N'-bis(phenyl)-2,2-diMe), NPB(N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'- diamine), or TPD (N,N'-Bis(3-methylphenyl)-N,N'-diphenylbenzidine).

Examples of the electron transport material include a heterocyclic compound represented by Chemical Formula 1, an oxadiazole derivative, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, and tetracyano Anthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and the like can be used. It can also be used. Specifically, LGC 201 (LG Chem) can be used.

As the electron injection material, for example, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used.

Hole blocking materials include (8-hydroxyquinolinolato)lithium (Liq), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), and bassocuproin ( bathocuproine, BCP), or LiF.

As the electron blocking material, TCTA (Tris(4-carbazoyl-9-ylphenyl)amine) may be used.

Red, green, or blue light-emitting materials may be used as the light-emitting material, and two or more light-emitting materials may be mixed and used if necessary. Further, a fluorescent material may be used as the light emitting material, but a phosphorescent material may also be used. 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 also be used.

The luminescent material includes a heterocyclic compound represented by Chemical Formula 1, tris(8-hydroxyquinolinolato)aluminum (Alq ₃ ), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy City) Aluminum (BAlq), 4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl (DPVBi), spiro material, spiro-DPVBi (spyro) -4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl), iPBO (2-(2-benzooxazolyl)-phenol lithium salt), bis(biphenylvinyl) Metal complexes of benzene, aluminum-quinoline metal complexes, imidazoles, thiazoles, or oxazoles can be used.

The organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

The heterocyclic compound may act on a similar principle to that applied to an organic light emitting device in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors.

In addition, the present invention provides an electronic device including the above-described organic light emitting device.

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

<Production Example>

<Production Example 1>

Preparation of Intermediate 1-a

30 g (121.9 mmol) of 1-bromocarbazole and 9.7 g (243.8 mmol) of sodium hydride (60%) were suspended in 850 ml of dimethylformamide, followed by stirring at room temperature for 10 minutes. Then, 39.1 g (16.3 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was suspended in 255 ml of dimethylformamide and stirred for 15 hours at 60°C. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain intermediate 1-a, 43.6 g (yield: 75%).

Preparation of compound 1

Intermediate 1-a 10 g (20.9 mmol), (4-cyanophenyl) boronic acid 3.4 g (23.0 mmol), Pd(PPh ₃ ) ₄ 1.2 g (1.0 mmol), potassium carbonate 5.8 g (41.9 mmol) After suspended in 100 ml of toluene, 20 ml of ethyl alcohol, and 20 ml of distilled water, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain compound 1, 4.2 g (yield: 40%).

<Production Example 2>

Preparation of Intermediate 2-a

In a nitrogen atmosphere, 27.2 g (162.7 mmol) of carbazole was suspended in 800 ml of anhydrous tetrahydrofuran to prepare a suspension, and 71.6 ml (178.9 mmol) of 2.5 M n-butyllithium was slowly added dropwise at 0° C. for 30 minutes at room temperature. It was stirred. Then, the suspension prepared before 15 g (81.3 mmol) of cyanuric chloride was diluted with 400 ml of anhydrous tetrahydrofuran was slowly added dropwise, and the mixture was heated to reflux at 55° C. for 1 hour. After the mixture was cooled to room temperature, the reaction was terminated by adding excess water. The resulting solid was washed with distilled water and tetrahydrofuran mixture, and then washed once again with methanol to obtain intermediate 2-a, 25.4 g (yield: 70%).

Preparation of Intermediate 2-b

10 g (37.9 mmol) of 1-bromo-9H-carbazole and 3.0 g (75.7 mmol) of sodium hydride (60%) were suspended in 265 ml of dimethylformamide, followed by stirring at room temperature for 10 minutes. Then, 20.3 g (45.4 mmol) of the intermediate 2-a was suspended in 80 ml of dimethylformamide, and stirred at 60° C. for 15 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain intermediate 2-b, 19.8 g (yield: 80%).

Preparation of compound 2

Intermediate 2-b 10 g (15.2 mmol), (4-cyanophenyl) boronic acid 2.5 g (16.8 mmol), Pd(PPh ₃ ) ₄ 0.9 g (0.8 mmol), potassium carbonate 4.2 g (30.5 mmol) After suspended in 80 ml of toluene, 16 ml of ethyl alcohol, and 16 ml of distilled water, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain compound 2, 4.1 g (yield: 40%).

<Production Example 3>

Preparation of Intermediate 3-a

30 g (92.3 mmol) of 1,8-dibromo-9H-carbazole and 7.4 g (184.6 mmol) of sodium hydride (60%) were suspended in 650 ml of dimethylformamide, followed by stirring at room temperature for 10 minutes. Then, 29.6 g (110.8 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was suspended in 200 ml of dimethylformamide and stirred for 15 hours at 60°C. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain intermediate 3-a, 41.1 g (yield: 80%).

Preparation of compound 3

Intermediate 3-a 10 g (18 mmol), (4-cyanophenyl) boronic acid 2.9 g (19.8 mmol), Pd(PPh ₃ ) ₄ 1.0 g (0.9 mmol), potassium carbonate 5 g (36 mmol) After suspended in 90 ml of toluene, 18 ml of ethyl alcohol, and 18 ml of distilled water, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain compound 3, 4.6 g (yield: 43%).

<Comparative Production Example 1>

Preparation of Comparative Intermediate 1-a'

30 g (113.6 mmol) of 1-bromocarbazole and 9.1 g (227.2 mmol) of sodium hydride (60%) were suspended in 800 ml of dimethylformamide, followed by stirring at room temperature for 10 minutes. Then, 36.2 g (136.3 mmol) of 4-chloro-2,6-diphenylpyridine was suspended in 250 ml of dimethylformamide and stirred for 15 hours at 60°C. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain Comparative Intermediate 1-a', 45.9 g (yield: 85%).

Preparation of Comparative Compound A

Comparative intermediate 1-a' 10 g (21.0 mmol), (4-cyanophenyl) boronic acid 3.4 g (23.1 mmol), Pd(PPh ₃ ) ₄ 1.2 g (1.0 mmol), potassium carbonate 5.8 g (42.1 mmol) ) Was suspended in 100 ml of toluene, 20 ml of ethyl alcohol, and 20 ml of distilled water, and stirred at reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure, followed by silica gel column to obtain Comparative Compound A, 4.2 g (yield: 40%).

<Comparative Example 1>

ITO (Indium Tin Oxide) glass used as a positive electrode was ultrasonically washed for 30 minutes using IPA and distilled water, dried in an oven at 100°C for 30 minutes, and then transferred to a vacuum deposition apparatus chamber.

Next, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an organic emitting layer (OEL), and electrons in turn on the ITO substrate A transport layer (Electron Transport Layer, ETL) and an electron injecting layer (EIL) were sequentially deposited (0.5 to 1.0 Å/sec, 1 × 10 ^-7 to 4 × 10 ^-7 torr), and an Al layer as a negative electrode Was deposited. The organic light emitting layer was prepared to include a dopant (Comparative Compound A) in a weight ratio of 60:40 on each host (mCBP: 3,3-Di(9H-carbazol-9-yl)biphenyl).

After vacuum deposition, the substrate was transferred to a glove box, and an encapsulation was performed to manufacture an organic light emitting device. The sealing member may be provided with a glass cap equipped with a BaO hygroscopic agent (Getter), and applied with a sealing epoxy sealant to be UV irradiated to prevent oxygen and moisture penetration into the deposition surface. Was prevented.

<Example 1>

In Comparative Example 1, CBP (4,4′-Bis(N-carbazolyl)-1,1′'-biphenyl) was used instead of mCBP as the host, and the compound prepared in Preparation Example 1 was used instead of Comparative Compound A as the dopant. An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that 1 was used.

<Example 2>

In Comparative Example 1, mCP (N,N'-dicarbazolyl-3,5-benzene) was used instead of mCBP as the host, and Compound 2 prepared in Preparation Example 1 was used instead of Comparative Compound A as the dopant. , In the same manner as in Comparative Example 1, an organic light emitting device was manufactured.

<Example 3>

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 3 prepared in Preparation Example 1 was used instead of Comparative Compound A as the dopant in Comparative Example 1.

The components used in the Examples and Comparative Examples are shown in Table 1 below.

layer material Thickness (nm) Cathode Al 100 EIL LiF One ETL LGC201 (LG Chem) 35 OEL Host: mCBP, CBP, or mCP
Dopant: Compounds 1-3 or Comparative Compound A
Host: Dopant=60:40 weight ratio 35 EBL TCTA 15 HTL NPB 75 HIL NPB: HAT-CN = 90:10 weight ratio 10 Anode ITO 150

<Experimental Example>

For the organic light-emitting device prepared in the above Examples and Comparative Examples, the luminescence luminance, luminous efficiency, and luminescence peak were respectively evaluated based on 10 mA/cm ² using Keithley sourcemeter “2400” and KONIKA MINOLTA “CS-2000”. The results are shown in Table 2 below. The samples showed a green emission peak value in the range of 520 to 526 nm.

division Light emitting layer (host) Light emitting layer (dopant) Luminance
[cd/m ² ] efficiency
[cd/A] Luminous peak
[nm] Example 1 CBP Compound 1 5,193 51.9 524 Example 2 mCP Compound 2 5,281 52.8 520 Example 3 mCBP Compound 3 5,311 53.1 520 Comparative Example 1 mCBP Comparative Compound A 4,072 40.7 516

In the above, the present invention has been described in detail only with respect to the described embodiments, but it is apparent to those skilled in the art that various modifications and variations are possible within the technical scope of the present invention, and it is natural that such modifications and modifications belong to the appended claims.

Claims (17)

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

In Chemical Formula 1,
X1 to X3 are the same or different from each other, each independently N or CR, and at least two of X1 to X3 are N,
R1 is an aryl group unsubstituted or substituted with a cyano group,
R2 is hydrogen; heavy hydrogen; Cyano group; Or an aryl group unsubstituted or substituted with a cyano group,
R and R3 are the same or different from each other, and independently are hydrogen or deuterium,
Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heteroaryl group,
a is an integer of 1 to 4, and when a is 2 or more, R2 is the same or different from each other,
b is an integer of 1 to 3, and when b is 2 or more, R3 is the same or different from each other. The method according to claim 1,
Formula 1 is a heterocyclic compound represented by any one selected from the following formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Chemical Formulas 2-1 to 2-4, X1 to X3, R1 to R3, Y1, Y2, a and b are as defined in Chemical Formula 1. The method according to claim 1,
The R1 is a heterocyclic compound which is an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a cyano group. The method according to claim 1,
R1 is a phenyl group unsubstituted or substituted with a cyano group; A biphenyl group unsubstituted or substituted with a cyano group; A triphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; An anthracenyl group unsubstituted or substituted with a cyano group; A chrysenyl group unsubstituted or substituted with a cyano group; A phenanthrenyl group unsubstituted or substituted with a cyano group; A perylenyl group unsubstituted or substituted with a cyano group; A fluoranthenyl group unsubstituted or substituted with a cyano group; A triphenylenyl group unsubstituted or substituted with a cyano group; A phenenyl group unsubstituted or substituted with a cyano group; A pyrenyl group unsubstituted or substituted with a cyano group; A tetrasenyl group unsubstituted or substituted with a cyano group; A pentacene group unsubstituted or substituted with a cyano group; A fluorenyl group unsubstituted or substituted with a cyano group; An indenyl group unsubstituted or substituted with a cyano group; An acenaphthylenyl group unsubstituted or substituted with a cyano group; A benzofluorenyl group unsubstituted or substituted with a cyano group; A spirobifluorenyl group unsubstituted or substituted with a cyano group; Or a heterocyclic compound which is a 2,3-dihydro-1H-indenyl group unsubstituted or substituted with a cyano group. The method according to claim 1,
R1 is a heterocyclic compound represented by any one selected from the following formulas R-1 to R-3:
[Formula R-1]

[Formula R-2]

[Formula R-3]

In the formulas R-1 to R-3,

Represents a position substituted with the heterocyclic compound represented by Formula 1 above. The method according to claim 1,
The formula 1 is a heterocyclic compound represented by at least one selected from the following formulas 2-1 to 2-4.
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Chemical Formulas 2-1 to 2-4,
X1 to X3, R1 to R3, a, b, Y1 and Y2 are as defined in Chemical Formula 1. The method according to claim 1,
R2 is hydrogen; heavy hydrogen; Cyano group; Or a heterocyclic compound which is an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a cyano group. The method according to claim 1,
R2 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a cyano group; A biphenyl group unsubstituted or substituted with a cyano group; A triphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; An anthracenyl group unsubstituted or substituted with a cyano group; A chrysenyl group unsubstituted or substituted with a cyano group; A phenanthrenyl group unsubstituted or substituted with a cyano group; A perylenyl group unsubstituted or substituted with a cyano group; A fluoranthenyl group unsubstituted or substituted with a cyano group; A triphenylenyl group unsubstituted or substituted with a cyano group; A phenenyl group unsubstituted or substituted with a cyano group; A pyrenyl group unsubstituted or substituted with a cyano group; A tetrasenyl group unsubstituted or substituted with a cyano group; A pentacene group unsubstituted or substituted with a cyano group; A fluorenyl group unsubstituted or substituted with a cyano group; An indenyl group unsubstituted or substituted with a cyano group; An acenaphthylenyl group unsubstituted or substituted with a cyano group; A benzofluorenyl group unsubstituted or substituted with a cyano group; A spirobifluorenyl group unsubstituted or substituted with a cyano group; Or a heterocyclic compound which is a 2,3-dihydro-1H-indenyl group unsubstituted or substituted with a cyano group. The method according to claim 1,
R2 is hydrogen; heavy hydrogen; Cyano group; Or a heterocyclic compound which is a phenyl group unsubstituted or substituted with a cyano group. The method according to claim 1,
Y1 and Y2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic compound having a heteroaryl group having 2 to 60 carbon atoms. The method according to claim 1,
Y1 and Y2 are the same as or different from each other, and each independently a heterocyclic compound selected from the following structural formulas:

In the above structural formula,

Indicates a position where Y1 and Y2 are substituted with the heterocyclic compound represented by Chemical Formula 1 above. The method according to claim 1,
Formula 1 is a heterocyclic compound represented by at least one selected from the following compounds:

An organic material comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer comprises a heterocyclic compound according to any one of claims 1 to 12. Light emitting element. The method according to claim 13,
The organic material layer is an organic light emitting device comprising at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer and an electron transport layer. The method according to claim 13,
The organic layer includes a light emitting layer,
The light emitting layer is an organic light emitting device comprising the heterocyclic compound as a dopant material. The method according to claim 15,
The light emitting layer is an organic light emitting device that is a green light emitting layer. An electronic device comprising the organic light-emitting device of claim 13.

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