KR20200092879A - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the same. By including the organic electroluminescent compound according to the present application, the organic electroluminescent device having a longer life and/or higher luminous efficiency compared to a conventional organic electroluminescent device may be provided.

Description

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.

An electroluminescent device (EL device) is a self-emissive display device, and has a wide viewing angle, excellent contrast, and high response speed. In 1987, Eastman Kodak first developed an organic electroluminescent device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

Organic electroluminescent devices (organic electroluminescent device) is a device that converts electric energy into light by applying electricity to an organic light-emitting material, and has a structure including an anode (anode) and a cathode (cathode) and an organic material layer therebetween. The organic material layer of the organic electroluminescent device includes a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., if necessary. can do. Materials used for the organic material layer are hole injection materials, hole transport materials, hole auxiliary materials, light emitting auxiliary materials, electron blocking materials, light emitting materials (including host and dopant materials), electron buffer materials, hole blocking materials, and electrons depending on function It can be divided into a delivery material, an electron injection material, and the like. In such an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode to the emission layer by applying a voltage, and excitons having high energy are formed by recombination of holes and electrons. By this energy, the light-emitting organic compound is brought into an excited state, and the excitation state of the light-emitting organic compound returns to the ground state and emits light by emitting energy as light.

The light-emitting material of the organic electroluminescent device is the most important factor for determining the light-emitting efficiency of the device, the light-emitting material must have high quantum efficiency and high mobility of electrons and holes, and the formed light-emitting material layer must be uniform and stable. These luminescent materials are divided into blue, green, or red luminescent materials depending on the luminous color, and there are also yellow or orange luminescent materials. In addition, the light emitting material may be divided into a host material and a dopant material in terms of functionality. In recent years, the development of high-efficiency and long-life organic electroluminescent devices has emerged as an urgent task. In particular, considering the level of EL characteristics required by medium- and large-sized OLED panels, it is urgent to develop materials that are superior to conventional light-emitting materials. .

On the other hand, Korean Patent Publication No. 2017-0096769 and Korean Registered Patent No. 1814875 disclose a heterocyclic compound and an organic electroluminescent device including the same, but there is still a need for development to improve the performance of the OLED device.

Korean Patent Publication No. 2017-0096769 (released on August 25, 2017) Korean Registered Patent No. 1814875 (released on December 27, 2017)

An object of the present application is to provide an organic electroluminescent compound effective for manufacturing an organic electroluminescent device having long life and/or high luminous efficiency characteristics.

The present inventors have completed the present invention by finding that the organic electroluminescent compound represented by the following formula (1) achieves the above object.

[Formula 1]

In Chemical Formula 1,

X is O or S;

R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or may be linked to each other to form a ring;

At least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ fuse with each other to the following Formula 2 to form a ring,

[Formula 2]

R ₅ to R ₈ which do not form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or Unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

이고, 단, R₉ 내지 R₁₂ 중 적어도 하나는

이고;R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino,

However, at least one of R ₉ to R ₁₂ is

ego;

L is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

ETU is substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted Or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted benzofuroprazinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted benzofuropyrimidinyl , Or substituted or unsubstituted benzothiopyrimidinyl.

The organic electroluminescent compound according to the present application may provide an organic electroluminescent device having long life and/or high luminous efficiency characteristics.

1 is a representative chemical formula of the organic electroluminescent compound according to the present application.

Hereinafter, the present application will be described in more detail, but this is for illustrative purposes and should not be construed to limit the scope of the present application.

As used herein, "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device, and can be included in any layer constituting the organic electroluminescent device, if necessary.

As used herein, “organic electroluminescent material” refers to a material that can be used in an organic electroluminescent device, and may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material is a hole injection material, hole transport material, hole auxiliary material, light emitting auxiliary material, electron blocking material, light emitting material, electron buffer material, hole blocking material, electron transport material, electron injection material, etc. Can.

As used herein, "(C1-C30)alkyl" means a straight or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. "(C2-C30)alkenyl" as used herein means a straight or branched chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20 carbon atoms, more preferably 2 to 20 carbon atoms. 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. As used herein, "(C2-C30)alkynyl" means a straight or branched chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20 carbon atoms, more preferably 2 to 20 carbon atoms. 10. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. As used herein, "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, and preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7 ring skeleton atoms, preferably 5 to 7, and is a group consisting of B, N, O, S, Si and P, preferably O , S and N means a cycloalkyl containing one or more heteroatoms selected from the group consisting of, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "(C6-C30)aryl(ren)" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated. The ring skeleton carbon number is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzoflu Orenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, perillynyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobi And fluorenyl and azulenyl groups. More specifically, examples of the aryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-Phenanthryl, 4-Phenanthryl, 9-Phenanthryl, Naphthacenyl, Pyrenyl, 1-Crysenyl, 2-Crysenyl, 3-Crysenyl, 4-Crysenyl, 5-Crysenyl, 6-Crysenyl , Benzo[c]phenanthryl, benzo[g]cristenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl , 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o- Terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p- Terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p -Tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p- tert -butylphenyl, p -(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4" -tert -butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl -2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl -2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, and the like.

As used herein, "(3-30 membered) heteroaryl (ren)" is an aryl group having 3 to 30 ring skeleton atoms, and including one or more heteroatoms selected from the group consisting of B, N, O, S, Si and P. it means. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system fused with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein also includes a form in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and includes a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, iso Quinolinyl, cynolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazineyl, And fused ring heteroaryls such as phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi Neil, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imi Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3- Pyridyl, 4-pyridyl, 1-indoleyl, 2-indoleyl, 3-indoleyl, 4-indoleyl, 5-indoleyl, 6-indoleyl, 7-indoleyl, 1-isoindoleyl, 2 -Isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3 -Benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl , 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2- Quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, Azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl , 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4 -Acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole -3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2- tert -butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indole Reel, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3- Indolyl , 4- tert -butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2 -Dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1- And germanium fluorenyl, 2-germa fluorenyl, 3-germa fluorenyl, 4-germa fluorenyl, and the like. “Halogen” as used herein includes F, Cl, Br and I atoms.

In addition, “ortho (o-)”, “meta (m-)”, and “para (p-)” are each prefixes indicating the relative positions of the substituents. Ortho (ortho) indicates that two substituents are adjacent to each other. For example, when the substituents are in positions 1 and 2 in a benzene substituent, they are called ortho positions. Meta indicates that two substituents are in positions 1 and 3, for example, when a substituent is in positions 1 and 3 in a benzene substituent, it is called a meta position. Para indicates that two substituents are in positions 1 and 4, and for example, when a substituent is in positions 1 and 4 in a benzene substituent, it is called a para position.

In addition, in the description of "substituted or unsubstituted" as used herein,'substitution' means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in one functional group. As used herein, substituted alkyl, substituted aryl (ren), substituted heteroaryl (ren), substituted silyl, substituted amino, substituted pyrimidine, substituted triazinyl, substituted quinazolinyl, substituted quinoxaly Neil, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted dibenzoquinazolinyl, substituted benzofuropyrazinyl, substituted benzothiopyrazinyl, substituted benzofuro Substituents of pyrimidinyl and substituted benzothiopyrimidinyl are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2 -C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 Circle) heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl substituted or unsubstituted (3-30 member) heteroaryl, (3-30 member) hetero (C6-C30)aryl, unsubstituted or substituted with aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1- C30) alkyldi(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, mono- or di-(C6-C30)aryl unsubstituted or substituted with (C1-C30)alkyl Amino, (C1-C30)alkyl (C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)aryl Boronyl, di(C1-C30)alkylboronil, (C1-C30)alkyl(C6-C30)arylboronil, (C6-C30)ar(C1-C30)alkyl, and (C1-C30) Alkyl(C6-C30)aryl. According to an aspect of the present application, the substituents are each independently (C1-C20)alkyl, (C6-C25)aryl, (C6-C25)aryl substituted or unsubstituted (5-25 membered) heteroaryl and (C1) -C10) alkyl (C6-C25) aryl. According to another aspect of the present application, the substituents are each independently (C1-C10) alkyl, (C6-C25) aryl, (C6-C18) aryl substituted or unsubstituted (5-20 membered) heteroaryl and ( C1-C5)alkyl (C6-C25)aryl. For example, the substituents are each independently methyl, phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenyl It may be one or more of substituted carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, and benzonaphthofuranyl.

Herein, a ring formed in connection with an adjacent substituent is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or combination of two or more adjacent substituents. Meaning and preferably, it may be a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic, or combinations thereof. Further, the formed ring may include one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. For example, the fused ring is a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted Fluorene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted indole ring, substituted or unsubstituted inden ring, substituted or unsubstituted benzene ring or substituted or It may be in the form of an unsubstituted carbazole ring.

In the formulas herein, heteroaryl (ren) and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 member) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1) -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted Mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl One or more selected from the group consisting of amino may be bound.

In Formula 1, R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted It may be substituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or may be linked to each other to form a ring. According to an aspect of the present application, R ₁ to R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-30 membered) Heteroaryl, or _one or more of R ₁ and R ₂ , R ₂ and R ₃ , and R ₃ and R ₄ may be connected to each other to form a ring. According to another aspect of the present application, R ₁ to R ₄ are each independently hydrogen, deuterium, unsubstituted (C6-C18)aryl, or (C6-C18)aryl substituted or unsubstituted (5-25 membered) Heteroaryl. For example, R ₁ to R ₄ may each independently be hydrogen, phenyl, naphthyl, biphenyl, phenanthrenyl, carbazolyl substituted with phenyl, dibenzothiophenyl, or dibenzofuranyl.

In Chemical Formula 1, at least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ are fused with Chemical Formula 2 to form a ring. According to an aspect of the present disclosure, R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ may be fused with Formula 2 to form a ring.

[Formula 2]

In Formula 1, those that do not form a ring by fusion with Formula 2 in R ₅ to R ₈ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to an aspect of the present application, each of R ₅ to R ₈ is independently hydrogen, deuterium, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C18)aryl, or substituted or unsubstituted (5-20 won) heteroaryl. According to another aspect of the present application, each of R ₅ to R ₈ may be independently hydrogen, deuterium, or unsubstituted (C6-C18)aryl. For example, R ₅ to R ₈ may be each independently hydrogen, phenyl, naphthyl or biphenyl.

이다. R₉ 내지 R₁₂ 중 적어도 하나는

이며, 본원의 일 양태에 따르면, R₉ 내지 R₁₂ 중 어느 하나는

일 수 있다. 본원의 또 다른 일 양태에 따르면, R₉ 내지 R₁₂는 각각 독립적으로 수소, 중수소, 또는

이고, 단, R₉ 내지 R₁₂ 중 어느 하나는

일 수 있다.In Formula 1, R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted Substituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino,

to be. At least one of R ₉ to R ₁₂

And according to one aspect of the present application, any one of R ₉ to R ₁₂ is

Can be According to another aspect of the present application, R ₉ to R ₁₂ are each independently hydrogen, deuterium, or

However, any one of R ₉ to R ₁₂

Can be

L is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to an aspect of the present disclosure, L is a single bond, substituted or unsubstituted (C6-C25)arylene, or substituted or unsubstituted (5-25 membered) heteroarylene. According to another aspect of the present application, L is a single bond, unsubstituted (C6-C18)arylene, or unsubstituted (5-20 membered) heteroarylene. For example, L can be a single bond, phenylene, naphthylene, biphenylene, or pyridylene.

The ETU is substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, Substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted benzofuroprazinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted benzofuropyrimiyl Dinyl, or substituted or unsubstituted benzothiopyrimidinyl. According to one aspect of the present application, ETU is substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted Benzofuropyrimidinyl, or substituted benzothiopyrimidinyl. The substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted benzofuropyrimidinyl, and substitution Substituents of benzothiopyrimidinyl may be each independently one or more of substituted or unsubstituted (C6-C25)aryl and substituted or unsubstituted (5-30 membered) heteroaryl, preferably each independently phenyl. , Naphthyl, biphenyl, phenanthrenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl substituted with phenyl, dibenzothiophenyl, dibenzofuran One, benzonaphthothiophenyl, and benzonaphthofuranyl. For example, ETU can be represented by any of the following equations.

Wherein R is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 Circle) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to an aspect of the present application, R is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-30 Won) Heteroaryl. According to another aspect of the present application, R are each independently (C6-C25)aryl substituted or unsubstituted with one or more of hydrogen, deuterium, (C1-C10)alkyl and (C6-C18)aryl, or (C6- C18) aryl substituted or unsubstituted (5-30 membered) aryl. For example, R is each independently substituted with hydrogen, phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenyl Can be carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, or benzonaphthofuranyl.

The compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.

[Formula 1-1] [Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, R ₅ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30) Aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; R ₁ to R ₄ , L, ETU, and X are the same as defined in Formula 1. In addition, in Chemical Formulas 1-1 to 1-3, preferred embodiments and specific examples of R ₁ to R ₁₂ , L, ETU, and X are as mentioned in Chemical Formula 1.

The compound represented by Formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.

The organic electroluminescent compounds herein can be prepared using synthetic methods known to those skilled in the art. For example, the organic electroluminescent compound of the present application may be synthesized as shown in the following reaction formulas 1 to 4, but is not limited thereto.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

In Reaction Schemes 1 to 4, R ₁ to R ₁₂ , X, L, and ETU are the same as defined in Formula 1, and Hal is halogen.

Although the exemplary synthetic examples of the present invention represented by Formula 1 have been described above, these are all Buchwald-Hartwig cross coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, Specific synthesis example based on intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN ₁ substitution reaction, SN ₂ substitution reaction, and Phosphine-mediated reductive cyclization reaction Those skilled in the art will readily understand that the reaction proceeds even if other substituents defined in Chemical Formula 1 are combined in addition to the substituents specified in the above.

The dopant that can be used in combination with the compounds herein can be one or more phosphorescent or fluorescent dopants, with phosphorescent dopants being preferred. The phosphorescent dopant is not particularly limited, but may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and preferably, iridium ( Ir), osmium (Os), copper (Cu) and platinum (Pt) may be an ortho metallized complex compound of a metal atom, and more preferably, an ortho metallized iridium complex compound.

As a dopant included in the organic electroluminescent device of the present application, a compound represented by Formula 101 may be used, but is not limited thereto.

[Formula 101]

In Chemical Formula 101,

L is any one selected from the following structures 1 to 3;

[Structure 1] [Structure 2] [Structure 3]

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₀ to R ₁₀₃ may be linked to adjacent substituents to form a substituted or unsubstituted fused ring with pyridine, for example, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted Benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted Noquinoline formation is possible;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₄ to R ₁₀₇ may be connected to adjacent substituents to form a substituted or unsubstituted fused ring with benzene, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted Dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine formation is possible;

R ₂₀₁ to R ₂₂₀ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted (C6-C30)aryl, or adjacent substituents may be connected to each other to form a substituted or unsubstituted fused ring;

s is an integer from 1 to 3.

Specifically, specific examples of the dopant compound are as follows, but are not limited thereto.

Compound represented by the formula (1) herein may be included in one or more layers constituting the organic electroluminescent device, for example, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, It may be included in one or more layers selected from an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. Each of the above layers may further consist of several layers.

In addition, the compound represented by Formula 1 herein is not limited thereto, and may be included in a light emitting layer and/or an electron transport band. The compound represented by Formula 1 herein may be included as a host material in the light emitting layer, and at the same time or alternatively, may be included as an electron buffer material and/or a hole blocking material in an electron transport band.

The electron transport band herein may be composed of one or more layers selected from the group consisting of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and each of the layers may be formed of one or more layers. Preferably, the electron transport band includes an electron buffer layer and/or a hole blocking layer. Further, the electron transport band may further include one or more layers of an electron transport layer and an electron injection layer.

Of the organic electroluminescent materials herein, for example, hole injection material, hole transport material, hole auxiliary material, light emitting auxiliary material, electron blocking material, light emitting material, electron buffer material, hole blocking material, electron transport material and electron injection material One or more materials may include a compound represented by Chemical Formula 1 above. The organic electroluminescent material may be at least one of a light emitting material, an electron buffer material, and a hole blocking material. The organic electroluminescent material may be composed of the compound represented by Formula 1 alone, or may further include common materials included in the organic electroluminescent material. When two or more types of materials are included in one layer, they may be mixed vapor-deposited to form a layer, or separately co-deposited to form a layer.

The organic electroluminescent device of the present application includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic material layer includes at least one light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer and an electron blocking layer It may further include one or more layers selected from the layers.

Each of the first electrode and the second electrode may be formed of a transparent conductive material, or may be formed of a semi-transmissive or reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a front emission type, a back emission type, or a double-sided emission type. Further, the hole injection layer may be additionally doped with p-dopant, and the electron injection layer may be additionally doped with n-dopant.

The organic electroluminescent device of the present application may include the compound represented by Chemical Formula 1, and may further include conventional materials included in the organic electroluminescent material. The organic electroluminescent device including the organic electroluminescent compound of the present application represented by Formula 1 may exhibit high luminous efficiency and/or long life characteristics.

In addition, the organic electroluminescent material according to an example of the present application may be used as a light emitting material for a white organic light emitting device (White Organic Light Emitting Device). The white organic electroluminescent device is a side-by-side method or a stacking method according to the arrangement form of R (red), G (green) or YG (yellow-green), B (blue) light-emitting units Alternatively, various structures such as a color conversion material (CCM) method have been proposed, and the present invention can also be applied to such a white organic electroluminescent device.

The organic electroluminescent material according to an example of the present application may also be used in an organic electroluminescent device including a quantum dot (QD).

In addition, the present application may provide a display device using the compound represented by Chemical Formula 1. That is, it is possible to manufacture a display device or a lighting device using the compound of the present application. Specifically, it is possible to manufacture a display device, for example, a smart phone, a tablet, a laptop, a PC, a TV or a vehicle display device, or a lighting device, for example, an outdoor or indoor lighting device, using the compounds of the present application. It is possible.

Hereinafter, for a detailed understanding of the present application, representative compounds of the present application are shown, and methods for preparing the compounds according to the present application and their physical properties are shown. However, the present application is not limited to the following examples.

[ Example 1] Preparation of Compound C-160

Preparation of compound 1-1

In the reaction vessel, benzo[b]thiophen-2-ylboronic acid (37 g, 205.05 mmol), 2-bromo-6-chlorobenzaldehyde (30 g, 136.7 mmol), tetrakis(triphenylphosphine)palladium ( 4.7 g, 4.1 mmol), potassium carbonate (47.2 g, 341.75 mmol), 400 mL of tetrahydrofuran, and 100 mL of distilled water were added, followed by stirring at 100°C for 4 hours. When the reaction was over, it was washed with distilled water and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. After that, purification was performed by column chromatography to obtain compound 1-1 (35 g, yield: 94%).

Preparation of compound 1-2

Compound 1-1 (35 g, 128.32 mmol), and (methoxymethyl)triphenylphosphonium chloride (66 g, 192.48 mmol) were added to 350 mL of tetrahydrofuran in a reaction vessel, followed by potassium- tert -at 0°C. 193 mL of butoxide 1M was added dropwise. After the dropwise addition, the reaction temperature was gradually raised to room temperature, and further stirred for 2 hours. After the reaction was completed, the mixture was extracted with ethyl acetate, and then the organic layer was dried over magnesium sulfate. After removal of the solvent by rotary evaporation, purification by column chromatography gave compound 1-2 (31 g, yield: 80%).

Preparation of compound 1-3

After dissolving compound 1-2 (31 g, 103.06 mmol) in chlorobenzene in a reaction vessel, 3.1 mL of Etons reagent was slowly added dropwise. After the dropwise addition, the mixture was further stirred at room temperature for 2 hours. When the reaction was over, it was washed with distilled water and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. After that, purification was performed by column chromatography to obtain Compound 1-3 (24.4 g, yield: 88%).

Preparation of compound 1-4

Compound 1-3 (9.0 g, 29.77 mmol), bis(pinacolato)diboron (9.1 g, 35.72 mmol), tris(dibenzylideneacetone)dipalladium (1.1 g, 1.19 mmol), 2 -Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (1.0 g, 2.38 mmol), potassium acetate (8.8 g, 89.31 mmol) and 150 mL of 1,4-dioxane are added Then, the mixture was refluxed at 130° C. for 6 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. After that, purification by column chromatography gave Compound 1-4 (9.0 g, yield: 84%).

Preparation of compound C-160

Compound 1-4 (4.5 g, 12.49 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3, in a reaction vessel 5-triazine (6.6 g, 14.20 mmol), tetrakis(triphenylphosphine)palladium (0.4 g, 0.34 mmol), sodium carbonate (3.0 g, 28.38 mmol), toluene 55 mL, ethanol 14 mL and distilled water 14 mL After the addition, the mixture was stirred at 120°C for 4 hours. After the reaction, the precipitated solid was washed with distilled water and methanol. After that, purification was performed by column chromatography to obtain compound C-160 (3.9 g, yield: 51%). The properties of the synthesized compound C-160 are as follows.

[ Example 2] Preparation of compound C-5

Compound 1-4 (4.0 g, 11.1 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (4.6 g, 13.3 mmol), Pd(PPh ₃ ) ₄ (0.6 g, 0.56 mmol), K ₂ CO ₃ (3.1 g, 22.2 mmol) was added 5.0 mL of EtOH, 40 mL of toluene and 11 mL of distilled water, followed by reflux stirring for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, stirred at room temperature, filtered with MeOH, and the resulting solid was filtered under reduced pressure and purified by column chromatography with MC/Hex to obtain compound C-5 (4.9 g, yield: 81%).

[ Example 3] Preparation of compound C-146

Compound 1-3 (4.0 g, 14.9 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- 1)phenyl)-1,3,5-triazine (7.1 g, 16.4 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.8 mmol), s-phos (0.6 g, 1.5 mmol), NaOtBu (3.5 g , 37.3 mmol) was added to 80 mL of o-xylene, followed by stirring under reflux for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, stirred at room temperature, filtered with MeOH, and the resulting solid was filtered under reduced pressure and purified by column chromatography with MC/Hex to obtain compound C-146 (3.6 g, yield: 45%).

[ Example 4] Preparation of compound C-499

Compound 4-1 (5.40 g, 15.7 mmol), 2-(6-chloropyridin-3-yl)-4,6-diphenyl-1,3,5-triazine (5.41 g, 15.7 mmol) in a flask, Bis(triphenylphosphine)palladium (II)dichloride (551 mg, 0.78 mmol), sodium carbonate (2.5 g, 23.5 mmol), and 80 mL of THF: distilled water (10:1 mixed solution) were dissolved and dissolved for 6 hours. It was stirred at reflux. After the reaction was completed, extraction was performed with ethyl acetate, followed by separation by column chromatography to obtain compound C-499 (3.0 g, yield: 36%).

[ Example 5] Preparation of compound C-230

Synthesis of Compound 5-1

To the flask 6-chloro-3-iodo-2-methoxynaphthalene (30 g, 94.19 mmol), (2-fluorophenyl)boronic acid (13.1 g, 94.19 mmol), tetrakis(triphenylphosphine)palladium (5.4 g, 4.709 mmol), potassium carbonate (39 g, 282.5 mmol), 580 mL of toluene, 145 mL of ethanol, and 145 mL of water were dissolved and stirred at reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. Then, it was separated by column chromatography to obtain compound 5-1 (18.5 g, yield: 68%).

Synthesis of Compound 5-2

Compound 5-1 (18.5 g, 64.52 mmol) and pyridine hydrochloride (112 g, 967.9 mmol) were added to the flask, and the mixture was stirred at reflux for 3 hours at 230°C. After the reaction was completed, the mixture was cooled to room temperature, and extracted with dimethyl chloride. After distillation under reduced pressure, hexane was added dropwise and filtered to obtain compound 5-2 (14.8 g, yield: 84%).

Synthesis of Compound 5-3

To the flask, compound 5-2 (14.8 g, 54.27 mmol), potassium carbonate (3.75 g, 27.13 mmol), and dimethylformamide 360 mL were added and stirred under reflux for 1 hour. After the reaction was completed, after cooling to room temperature, water was added dropwise and filtered to obtain compound 5-3 (13 g, yield: 94%).

Synthesis of Compound 5-4

To the flask, compound 5-3 (10 g, 39.57 mmol), bis(pinacolato)diboron (12 g, 47.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.4 g, 1.582 mmol) , 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.3 g, 3.165 mmol), potassium acetate (11.6 g, 118.7 mmol), and 200 mL of 1,4-dioxane The mixture was refluxed for 3 hours. After the reaction was completed, extraction was performed with ethyl acetate, and separated by column chromatography to obtain compound 5-4 (7.8 g, yield: 54%).

Synthesis of Compound C-230

To the flask, compound 5-4 (4.5 g, 13.07 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (5 g, 13.07 mmol), tetrakis( Triphenylphosphine) palladium (0.75 g, 0.653 mmol), potassium carbonate (5.4 g, 39.22 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of water were added and stirred under reflux for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, methanol was added dropwise, and then filtered. Thereafter, the mixture was dissolved with dimethyl chloride and separated by column chromatography to obtain compound C-230 (3.7 g, yield: 53%).

Meanwhile, the present inventors found the following fact by comparing the following B-type compound according to the present application with the following A-type compound not according to the present application.

A device comprising a B-type compound as a red host material may have improved life characteristics compared to a device containing an A-type compound as a red host material. This is not intended to be limited in theory, but the B-type compound has a long conjugation and low steric-hindrance energy compared to the A-type compound, and the compound having a long conjugation stabilizes the electron It is believed that this is because a compound having low steric hindrance energy is difficult to decompose at a high temperature.

Hereinafter, the characteristics of the organic electroluminescent device including the compound of the present application will be described for a detailed understanding of the present invention. However, the following examples merely describe the characteristics of the OLED according to the present application for a detailed understanding of the present application, and the present application is not limited to the following examples.

[device Manufacturing example 1 and 2] comprising a compound according to the present application OLED Produce

An OLED device comprising the compound according to the present application was prepared. First, the transparent electrode ITO thin film (10 Ω/□) obtained from the glass for OLED (manufactured by Geomatech Co., Ltd.) was subjected to ultrasonic cleaning using acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used. Next, after the ITO substrate is mounted on the substrate holder of the vacuum deposition equipment, compound HI-1 is put in a cell in the vacuum deposition equipment, exhausted until the vacuum degree in the chamber reaches 10 ^-6 torr, and then a current is applied to the cell And evaporated to deposit a 80 nm thick first hole injection layer on the ITO substrate. Subsequently, compound HI-2 was put into another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a 5 nm thick second hole injection layer on the first hole injection layer. Subsequently, a compound HT-1 was put into a cell in a vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a 10 nm thick first hole transport layer on the second hole injection layer. Compound HT-2 was put in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a 60 nm thick second hole transport layer on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. The compound described as a host in Table 1 as a host was put in a cell in a vacuum deposition apparatus as a host, and compound D-71 was added as a dopant in another cell. A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by doping the dopant in an amount of 3% by weight, respectively. Subsequently, the electron transporting layer having a thickness of 35 nm was deposited on the light emitting layer by evaporating Compound ET-1 and Compound EI -1 at 1:1 rates in two other cells. Subsequently, the compound EI- 1 was deposited as an electron injection layer on the electron transport layer to a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to produce an OLED. .

[Device Manufacturing Example 3] OLED production including the compound according to the present application

A first hole for the injection layer thickness was deposited by 60 nm, the first deposition the thickness of the hole transport layer was 20 nm thick, and the second with the use of the compound HT-3 in place of Compound HT-2 as the hole transport layer 5 nm An OLED was manufactured in the same manner as in Device Manufacturing Example 1, except that a second hole transport layer having a thickness was deposited, and a light emitting layer or an electron transport layer was deposited as follows. Compound BH is put as a host in a cell in a vacuum deposition apparatus, and compound BD is put as a dopant in another cell, and then the evaporation of the two materials at different rates makes the dopant 2 wt% of the total amount of the host and dopant, respectively. A light emitting layer having a thickness of 20 nm was deposited on the second hole transport layer by doping with a positive amount. Subsequently, Compound C-160 as an electron buffer layer (or hole blocking layer) was deposited on the light emitting layer to a thickness of 5 nm. Compound ET-1 and compound EI-1 were evaporated in two other cells at a rate of 1:1 to deposit a 30 nm thick electron transport layer on the electron buffer layer (or hole blocking layer).

[ Comparative example 1] comprising a compound not according to the present application OLED Produce

An OLED was manufactured in the same manner as in Device Manufacturing Example 1, except that Compound A was used as a host for the light emitting layer.

[ Comparative example 2] comprising a compound not according to the present application OLED Produce

An OLED was manufactured in the same manner as in Device Manufacturing Example 1, except that Compound B was used as a host for the light emitting layer.

[ Comparative example 3] comprising a compound not according to the present application OLED Produce

An electron buffer layer (or a hole blocking layer) was not deposited, except that a 35 nm thick electron transport layer was deposited by evaporating Compound ET-1 and Compound EI -1 as 1:1 electron transport layers on the light emitting layer at a rate of 1:1. OLED was manufactured in the same manner as in Device Manufacturing Example 3.

Device manufacturing examples 1 and 2 and the driving voltage of the OLED manufactured in Comparative Examples 1 and 2 based on the brightness of 1,000 nits, CIE color coordinates, and the time from the light intensity at the brightness of 5,000 nits falls from 100% to 95% ( Lifespan; T95) are shown in Table 1 below.

[Table 1]

From Table 1 above, it can be confirmed that the organic electroluminescent device comprising the compound according to the present application as a host material has a longer life characteristic compared to the organic electroluminescent device comprising the compound not according to the present application as a host material.

The driving voltage, luminous efficiency, and color coordinates of the 1,000 nit luminance standard of the OLEDs manufactured in Device Manufacturing Example 3 and Comparative Example 3 are shown in Table 2 below.

[Table 2]

From Table 2, it can be seen that the organic electroluminescent device comprising the compound according to the present application as an electron buffer layer (or hole blocking layer) material exhibits higher luminous efficiency characteristics compared to the organic electroluminescent device not according to the present application.

Compounds used in the device manufacturing examples and comparative examples are shown in Table 3 below.

[Table 3]

Claims (8)

An organic electroluminescent compound represented by Formula 1 below:
[Formula 1]

In Chemical Formula 1,
X is O or S;
R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or may be linked to each other to form a ring;
At least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ fuse with each other to the following Formula 2 to form a ring,
[Formula 2]

R ₅ to R ₈ which do not form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or Unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;
R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino,

However, at least one of R ₉ to R ₁₂ is

ego;
L is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
ETU is substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted Or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted benzofuroprazinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted benzofuropyrimidinyl , Or substituted or unsubstituted benzothiopyrimidinyl. The method of claim 1, wherein the substituted alkyl, substituted aryl (ren), substituted heteroaryl (ren), substituted silyl, substituted amino, substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, Substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted dibenzoquinazolinyl, substituted benzofuropyrazinyl, substituted benzothiopyrazinyl, substituted benzofuropyrimiyl The substituents of dinyl and substituted benzothiopyrimidinyl are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30) Alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 won) (3-30 membered) heteroaryl, (3-30 membered) heteroaryl substituted or unsubstituted with heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl Substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30) Alkyldi(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, mono- or di-(C6-C30)arylamino unsubstituted or substituted with (C1-C30)alkyl, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboro Neil, di(C1-C30)alkylboronil, (C1-C30)alkyl(C6-C30)arylboronil, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl( C6-C30) One or more organic electroluminescent compounds selected from the group consisting of aryl. According to claim 1, wherein the formula 1 is represented by any one of the following formula 1-1 to 1-3, an organic electroluminescent compound:
[Formula 1-1] [Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,
R ₅ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;
R ₁ to R ₄ , L, ETU, and X are the same as defined in claim 1. The organic electroluminescent compound according to claim 1, wherein the ETU is represented by any one of the following formulas:

In the above formula,
R is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) hetero Aryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted silyl, or substituted or unsubstituted amino. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds.

An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent compound is included in at least one of a light emitting layer and an electron transport band.

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