KR20220008212A - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By including the organic electroluminescent compound according to the present application, the organic electroluminescent device having low driving voltage and/or high luminous efficiency characteristics can be manufactured. As a result of intensive research to solve the above technical problem, the present inventors have found that the organic electroluminescent compound represented by chemical formula 1 achieves the above object and completed the present invention.

Description

Organic electroluminescent compound and organic electroluminescent device comprising same

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

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

The organic electroluminescent device has a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer in order to increase their efficiency and stability. In this case, selection of the compound included in the hole transport layer is recognized as one of means for improving device characteristics such as hole transport efficiency to the light emitting layer, light emitting efficiency, and lifetime.

In this regard, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N as hole injection and transport materials in organic electroluminescent devices '-Diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-tris(3-methylphenyl) Phenylamino) triphenylamine (MTDATA) has been used, but when such a material is used, the quantum efficiency and lifespan of the organic electroluminescent device are deteriorated. , because thermal stress is generated between the anode and the hole injection layer, and the lifespan of the device is rapidly reduced due to such thermal stress In addition, the organic material used for the hole injection layer has very high hole mobility. For this reason, the hole-electron charge balance is broken, and thus quantum efficiency (cd/A) is lowered.

Therefore, the development of a hole transport layer material for improving the performance of the organic electroluminescent device is still required.

International Patent Publication No. WO 2016/021989 A1 discloses an example in which spiro[fluorene-9,9'-xanthene] derivative and spiro[fluorene-9,9'-thioxanthene] derivative compounds are used as an electron buffer layer or electron transport layer material. Although disclosed, it is not used as a hole transport layer material as in the present invention.

International Patent Publication WO 2016/021989 A1 (published on Nov. 2, 2016)

An object of the present invention is to provide an organic electroluminescent compound capable of manufacturing an organic electroluminescent device having low driving voltage and/or high luminous efficiency characteristics, and secondly, an organic electroluminescent compound comprising the organic electroluminescent compound. To provide a light emitting device.

As a result of intensive research to solve the above technical problem, the present inventors have found that the organic electroluminescent compound represented by the following Chemical Formula 1 achieves the above object and completed the present invention.

[Formula 1]

In Formula 1,

X and Y are each independently O or S;

L ₁ is a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₂ -N-(Ar ₃ )(Ar ₄ ); may be linked with adjacent substituents to form a ring;

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 (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, or -L ₃ -N-(Ar ₅ )(Ar ₆ ); may be linked with adjacent substituents to form a ring;

L ₂ and L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

Ar ₃ to Ar ₆ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted a fused ring group of a cyclic (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or a substituted or unsubstituted (3-30 membered) heteroaryl;

a to c are each independently an integer from 1 to 4, d is an integer from 1 to 3;

When a to d are each independently, an integer of 2 or more, each of R ₁ to R ₄ may be the same as or different from each other.

By including the organic electroluminescent compound according to the present invention, an organic electroluminescent device having low driving voltage and/or high luminous efficiency characteristics can be manufactured.

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

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present application is described in more detail, but it is for illustrative purposes only and should not be construed as limiting the scope of the present application.

The present application relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the organic electroluminescent compound.

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

As used herein, “organic electroluminescent material” means 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, if necessary. For example, the organic electroluminescent material may include a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, It may be an electron transporting material, an electron injecting material, or the like.

As used herein, the term "hole transport zone" refers to a region in which holes move between the first electrode and the light emitting layer, for example, at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, and an electron blocking layer. may include Each of the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emission auxiliary layer and the electron blocking layer may be a single layer or a plurality of layers in which two or more layers are stacked. According to an example of the present application, the hole transport zone may include a first hole transport layer and a second hole transport layer. The second hole transport layer may be one or more of the plurality of hole transport layers, and may include at least one of a hole auxiliary layer, a light emitting auxiliary layer, and an electron blocking layer. In addition, according to another example of the present application, the hole transport zone may include a first hole transport layer and a second hole transport layer, and the first hole transport layer may be positioned between the first electrode and the light emitting layer, and the The second hole transport layer may be positioned between the first hole transport layer and the light emitting layer, and the second hole transport layer may be a layer serving as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer and/or an electron blocking layer. .

As used herein, "(C1-C30)alkyl" means a straight-chain or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, and 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, tert -butyl, sec -butyl and the like. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, “(C6-C30)aryl(ene)” refers to a monocyclic or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, and includes a spiro structure. It is preferable that it is 6-20, and, as for the said ring skeleton carbon number, it is more preferable that it is 6-15. Specific examples of the aryl include phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, di Phenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl , pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl (xylyl), mesityl, cumenyl ( cumenyl) spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, and the like. More specifically, the aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-ku Menyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, 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, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorene nyl, 4-fluorenyl, 9-fluorenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9 -Phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1- Triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluorantenyl, 9-fluoranthenyl, benzofluorantenyl , 11,11-dimethyl-1-benzo [a] fluorenyl, 11,11-dimethyl-2-benzo [a] fluorenyl, 11,11-dimethyl-3-benzo [a] fluorenyl, 11 ,11-dimethyl-4-benzo [a] fluorenyl, 11,11-dimethyl-5-benzo [a] fluorenyl, 11,11-dimethyl-6-benzo [a] fluorenyl, 11,11 -dimethyl-7-benzo [a] fluorenyl, 11,11-dimethyl-8-benzo [a] fluorenyl, 11,11-dimethyl-9-benzo [a] fluorenyl, 11,11-dimethyl -10-benzo [a] fluorenyl, 11,11-dimethyl-1-benzo [b] fluorenyl, 11,11-dimethyl-2-benzo [b] fluorenyl, 11,11-dimethyl-3 -benzo [b] fluorenyl, 11,11-dimethyl-4-benzo [b ] fluorenyl, 11,11-dimethyl-5-benzo [b] fluorenyl, 11,11-dimethyl-6-benzo [b] fluorenyl, 11,11-dimethyl-7-benzo [b] flu Orenyl, 11,11-dimethyl-8-benzo [b] fluorenyl, 11,11-dimethyl-9-benzo [b] fluorenyl, 11,11-dimethyl-10-benzo [b] fluorenyl , 11,11-dimethyl-1-benzo [c] fluorenyl, 11,11-dimethyl-2-benzo [c] fluorenyl, 11,11-dimethyl-3-benzo [c] fluorenyl, 11 ,11-dimethyl-4-benzo [c] fluorenyl, 11,11-dimethyl-5-benzo [c] fluorenyl, 11,11-dimethyl-6-benzo [c] fluorenyl, 11,11 -dimethyl-7-benzo [c] fluorenyl, 11,11-dimethyl-8-benzo [c] fluorenyl, 11,11-dimethyl-9-benzo [c] fluorenyl, 11,11-dimethyl -10-benzo [c] fluorenyl, 11,11-diphenyl-1-benzo [a] fluorenyl, 11,11-diphenyl-2-benzo [a] fluorenyl, 11,11-di Phenyl-3-benzo [a] fluorenyl, 11,11-diphenyl-4-benzo [a] fluorenyl, 11,11-diphenyl-5-benzo [a] fluorenyl, 11,11- Diphenyl-6-benzo [a] fluorenyl, 11,11-diphenyl-7-benzo [a] fluorenyl, 11,11-diphenyl-8-benzo [a] fluorenyl, 11,11 -diphenyl-9-benzo [a] fluorenyl, 11,11-diphenyl-10-benzo [a] fluorenyl, 11,11-diphenyl-1-benzo [b] fluorenyl, 11, 11-diphenyl-2-benzo [b] fluorenyl, 11,11-diphenyl-3-benzo [b] fluorenyl, 11,11-diphenyl-4-benzo [b] fluorenyl, 11 , 11-diphenyl-5-benzo [b] fluorenyl, 11,11-diphenyl-6-benzo [b] fluorenyl, 11,11-diphenyl-7-benzo [b] fluorenyl, 11,11-diphenyl-8-benzo [b] fluorenyl, 11,11-diphenyl-9-benzo [b] fluorenyl, 11,11-diphenyl-10-benzo [b] fluorenyl , 11,11-diphenyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,11-diphenyl-3-benzo [c] fluorene nyl, 11,11-diphenyl-4- Benzo [c] fluorenyl, 11,11-diphenyl-5-benzo [c] fluorenyl, 11,11-diphenyl-6-benzo [c] fluorenyl, 11,11-diphenyl-7 -benzo [c] fluorenyl, 11,11-diphenyl-8-benzo [c] fluorenyl, 11,11-diphenyl-9-benzo [c] fluorenyl, 11,11-diphenyl- 10-benzo [c] fluorenyl 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro -2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4 -phenanthrenyl, etc. are mentioned. As used herein, "(3-30 membered) heteroaryl (ene)" has 3 to 30 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge. It means an aryl group comprising a, wherein the number of ring skeleton atoms is preferably 5 to 25. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein includes a form in which one or more heteroaryl groups or aryl groups are connected to a heteroaryl group by a single bond. Specifically, as examples of the heteroaryl, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl , tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, monocyclic heteroaryl such as pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzo Furanyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl , benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropira Zinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imida Zopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzo Carbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolidinyl, acridinyl, silafluorenyl, germaniumfluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl and fused-ring heteroaryls such as chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, the heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl , 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7- Indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 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, aza Carbazolyl-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-oxa zolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrole- 5-yl, 2-t-Butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl -3-Indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4- t-Butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl , 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3 -naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl , 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl nyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzo Furanyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]- Benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b] -benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b ]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1- b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1 -b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl , 4-naphtho- [1,2-b] -benzothiophenyl, 5-naphtho- [1,2-b]-benzothiophenyl, 6-naphtho- [1,2-b]-benzothio Phenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzo Thiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]- Benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b] -benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho- [2,1-b ]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1- b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1 -b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d ]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio [3,2-d] pyrimidinyl, 6-benzothio [3,2-d] pyrimidinyl, 7-benzothio [3,2-d] pyrimidinyl, 8-benzothio [ 3,2-d] pyrimidinyl, 9-benzothio [3,2-d] pyrimidinyl, 2-benzofuro [3,2-d] pyrazinyl, 6-benzofuro [3,2-d] Pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[ 3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl , 9-benzothio [3,2-d] pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl , 2- Germanfluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzo and selenophenyl. As used herein, "a fused ring group of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30)" has 3 to 30 ring carbon atoms, preferably 3 to 25 carbon atoms, more preferably 3 to 18 carbon atoms. It refers to a functional group of a ring in which one or more individual aliphatic rings and one or more aromatic rings having 6 to 30 ring skeleton carbon atoms, preferably 6 to 25 carbon atoms, and more preferably 6 to 18 carbon atoms are fused. For example, a fused ring group of at least one benzene and at least one cyclohexane, or a fused ring group of at least one naphthalene and at least one cyclopentane, and the like. In the present application, the carbon atom of the fused ring group of the aliphatic ring of (C3-C30) and the aromatic ring of (C6-C30) is at least one heteroatom selected from B, N, O, S, Si and P, preferably N, may be replaced with one or more heteroatoms selected from O and S. As used herein, “halogen” includes F, Cl, Br and I atoms.

In addition, "ortho; o", "meta; m", and "para; p" refer to the substitution positions of all substituents, and the ortho position is a compound in which the position of the substituent is immediately adjacent. and, for example, in the case of benzene, it means 1 and 2 positions, and the meta position refers to the next substitution position of the immediately neighboring substitution position. is a substitution position next to the meta position and means 1 or 4 positions in the case of, for example, benzene.

As used herein, the term "ring formed by connecting adjacent substituents" refers to a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination ring formed by connecting or fusion of two or more adjacent substituents. and preferably a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. In addition, the ring formed may comprise one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. According to an example of the present application, the number of ring skeleton atoms is (5 to 20 members), and according to another example of the present application, the number of ring skeleton atoms is (5 to 15 members). For example, the fused ring may include, for example, 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 indene ring, substituted or unsubstituted benzene ring or substituted Or it may be in the form of an unsubstituted carbazole ring.

In the description of "substituted or unsubstituted" herein, "substitution" means that a hydrogen atom in one functional group is replaced by another atom or another functional group (i.e., a substituent), and includes substitution of two or more substituents among the substituents with a connected group. do. For example, "a substituent to which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl or may be interpreted as a substituent in which two heteroaryls are connected. In the formulas herein, substituted alkyl, substituted alkylene, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, Substituent groups of substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl and substituted aliphatic and aromatic rings are each independently selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (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 membered) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (5-50 membered)heteroaryl unsubstituted or substituted with one or more of (C1-C30)alkyl, (C6-C30)aryl and di(C6-C30)arylamino; (C6-C30)aryl unsubstituted or substituted with one or more of (C1-C30)alkyl, (3-50 membered)heteroaryl, and mono- or di- (C6-C30)arylamino; 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- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino substituted or unsubstituted with one or more of (C1-C30)alkyl, (5-30 membered)heteroaryl and di(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphinyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, preferably at least one selected from the group consisting of, for example, unsubstituted methyl, unsubstituted phenyl, and unsubstituted naphthyl.

Hereinafter, an organic electroluminescent compound according to an embodiment will be described.

The organic electroluminescent compound according to an embodiment is represented by the following formula (1).

[Formula 1]

In Formula 1,

X and Y are each independently O or S;

L ₁ is a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₂ -N-(Ar ₃ )(Ar ₄ ); may be linked with adjacent substituents to form a ring;

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 (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, or -L ₃ -N-(Ar ₅ )(Ar ₆ ); may be linked with adjacent substituents to form a ring;

L ₂ and L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

Ar ₃ to Ar ₆ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted a fused ring group of a cyclic (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or a substituted or unsubstituted (3-30 membered) heteroaryl;

a to c are each independently an integer from 1 to 4, d is an integer from 1 to 3;

When a to d are each independently an integer of 2 or more, each of R ₁ to R ₄ may be the same as or different from each other.

For example, both X and Y may be O or both may be S, for example, X may be O and Y may be S, for example, X may be S and Y may be O.

For example, L ₁ may be a single bond or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond or a substituted or unsubstituted (C6-C25)arylene, more preferably , may be a single bond or a substituted or unsubstituted (C6-C18)arylene. For example, L ₁ may be a single bond or unsubstituted phenylene.

For example, Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C3-C30) may be a fused ring group of an aliphatic ring of and an aromatic ring of (C6-C30), preferably, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (5-30 membered) heteroaryl, or It may be a fused ring group of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C25) aromatic ring, more preferably, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, or a fused ring group of a substituted or unsubstituted (C3-C10) aliphatic ring and (C6-C18) aromatic ring. For example, Ar ₁ and Ar ₂ are each independently phenyl unsubstituted or substituted with naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p -biphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dihydrotetramethylphenanthrenyl.

For example, R ₁ to R ₄ may be all hydrogen.

The organic electroluminescent compound of Formula 1 according to an example may be represented by any one of Formulas 1-1 to 1-4 below.

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

[Formula 1-3] [Formula 1-4]

In Formulas 1-1 to 1-4,

R ₁ to R ₄ , X, Y, L ₁ , Ar ₁ , and Ar ₂ , and a to d are each independently the same as defined in formula (1).

In Formulas 1-1 to 1-4 according to an embodiment, X and Y are each independently O or S; L ₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene; Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring; It may be an organic electroluminescent compound, wherein _{R 1} to R _{4 are all hydrogen.}

According to an example, the organic electroluminescent compound of Formula 1 may be more specifically exemplified as the following compound, but is not limited thereto.

The compound of Formula 1 according to the present application may be prepared as shown in Schemes 1 to 3, but is not limited thereto, and may be prepared by a synthetic method known to those skilled in the art.

[Scheme 1]

[Scheme 2]

[Scheme 3]

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

Although exemplary synthesis examples of the present invention represented by Formula 1 have been described above, these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Specific synthesis examples 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 It will be readily understood by those skilled in the art that the reaction proceeds even if other substituents defined in Formula 1 other than the substituents specified in are bonded.

According to one embodiment, the present application provides an organic electroluminescent material including the organic electroluminescent compound of Formula 1 and an organic electroluminescent device including the organic electroluminescent material.

The organic electroluminescent material may consist of the organic electroluminescent compound of the present application alone, or may further include conventional materials included in the organic electroluminescent material.

The organic electroluminescent material according to an example may include at least one compound represented by Formula 1 above. The organic electroluminescent compound of Formula 1 of the present application may be preferably included as a hole transporting material in the hole transporting zone of the organic electroluminescent device. The hole transport zone includes a hole transport layer. In addition, the hole transport band may further include at least one of a hole injection layer, a hole auxiliary layer, a light emitting auxiliary layer, and an electron blocking layer in addition to the hole transport layer.

The organic electroluminescent material according to an example is a hole transporting material, a hole injecting material, a hole auxiliary material, a light emitting auxiliary material, and an electron blocking material, preferably a hole transporting material of a green light emitting organic electroluminescent device, a hole auxiliary material, or light emission. It may be an auxiliary material, and when the hole transporting layer is a plurality of layers, it may be a hole transporting material (hole auxiliary material) included in the hole transporting layer adjacent to the light emitting layer.

The organic electroluminescent material of the present application may include at least one host compound and a dopant compound in addition to the organic electroluminescent compound of Formula 1 above.

As the host included in the organic electroluminescent material of the present application, any known phosphorescent host may be used, for example, a plurality of host compounds (co-host) may be used as the host material. In this case, the weight ratio of the first host material to the second host material is 1:9 to 9:1, for example, 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, And it may be included in the organic electroluminescent material in a weight ratio range of 5:5. When two or more types of materials are included in one layer, they may be mixed and deposited to form a layer, or may be separately and simultaneously co-deposited to form a layer.

One or more phosphorescent or fluorescent dopants may be used as the dopant included in the organic electroluminescent material of the present application, and the phosphorescent dopant is preferable. The phosphorescent dopant material applied herein is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and may be preferred in some cases Preferably, it may be an ortho-metalated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases, more preferably, an ortho-metalated iridium complex It may be a compound.

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

[Formula 101]

In Formula 101,

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

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

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; It may be linked with adjacent substituents to form a ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted together with pyridine nopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; Adjacent substituted groups may be linked to form a substituted or unsubstituted ring, for example, together with benzene, 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;

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

s is an integer from 1 to 3.

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

Hereinafter, an organic electroluminescent device to which the aforementioned organic electroluminescent compound or organic electroluminescent material is applied will be described.

An organic electroluminescent device according to an embodiment includes a first electrode; a second electrode; and one or more artifact layers interposed between the first electrode and the second electrode.

According to an example, the organic layer includes a hole transport zone including the organic electroluminescent compound according to the present disclosure. The hole transport band is selected from the group consisting of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, and an electron blocking layer, for example, a hole transport layer, a hole injection layer, a hole auxiliary layer, and an electron blocking layer. It may consist of one or more layers. For example, the organic electroluminescent compound of the present application may be included alone or at least two of the organic electroluminescent compounds may be mixed, and conventional materials included in the organic electroluminescent material may be additionally included.

In addition, the organic layer may further include one or more layers selected from a light emitting layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron buffer layer, in addition to the hole transport band, each layer comprising: It can be further composed of several layers. In addition, the organic layer may further include one or more compounds selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. It may further include one or more metals selected from the group consisting of metals and organometallics of d-transition elements, or one or more complex compounds containing these metals.

The organic electroluminescent material according to an example may be used as a light emitting material for a white organic light emitting device. The white organic EL device is a side-by-side method, a stacking method, depending on the arrangement of R (red), G (green) or YG (yellow green), B (blue) light emitting units , or various structures such as a color conversion material (CCM) method have been proposed. In addition, the organic electroluminescent material according to an example may be used in an organic electroluminescent device including quantum dots (QD).

One of the first and second electrodes may be an anode (anode) and the other may be a cathode (cathode). In this case, each of the first electrode and the second electrode may be formed of a transparent conductive material or may be formed of a transflective or reflective conductive material. According to the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a double-sided emission type.

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. In the hole injection layer, a plurality of layers may be used for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, and two compounds may be used in each layer at the same time. In addition, the hole injection layer may be doped with a p-dopant. The electron blocking layer is positioned between the hole transport layer (or hole injection layer) and the light emitting layer, and blocks the overflow of electrons from the light emitting layer to trap excitons in the light emitting layer, thereby preventing light emission leakage. A plurality of layers may be used for the hole transport layer or the electron blocking layer, and a plurality of compounds may be used for each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. In the electron buffer layer, a plurality of layers may be used for the purpose of controlling electron injection and improving interfacial properties between the light emitting layer and the electron injection layer, and two compounds may be used for each layer at the same time. A plurality of layers may be used for the hole blocking layer or the electron transport layer, and a plurality of compounds may be used for each layer. In addition, the electron injection layer may be doped with an n-dopant.

The light-emitting auxiliary layer is located between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is located between the anode and the light-emitting layer, it facilitates injection and/or transfer of holes or It may be used to block overflow, and when the light-emitting auxiliary layer is positioned between the cathode and the light-emitting layer, it may be used to facilitate injection and/or transfer of electrons or to block overflow of holes. In addition, the hole auxiliary layer is positioned between the hole transport layer (or hole injection layer) and the light emitting layer, and may have an effect of smoothing or blocking the transport rate (or injection rate) of holes, and thus charge balance (charge balance) ) can be adjusted. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer may be used as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

In the organic electroluminescent device of the present application, on the inner surface of at least one of the pair of electrodes, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter, these are referred to as “surface layers”) ) is preferred. Specifically, it is preferable to arrange a chalcogenide (including oxide) layer of silicon and aluminum on the surface of the anode on the side of the light emitting medium layer, and a metal halide layer or metal oxide layer on the surface of the cathode on the side of the light emitting medium layer. Drive stabilization of an organic electroluminescent element can be obtained by the said surface layer. Preferred examples of the chalcogenide include SiO _X (1≤X≤2), AlO _X (1≤X≤1.5), SiON, SiAlON, and the like, and preferred examples of the metal halide include LiF, MgF ₂ , CaF ₂ , fluoride and rare earth metals, and preferred examples of the metal oxide include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

Further, in the organic electroluminescent device of the present application, it is also preferable to arrange a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant on at least one surface of a pair of electrodes. In this way, since the electron transport compound is reduced to an anion, it is easy to inject and transfer electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to a cation, it is easy to inject and transport holes from the mixing region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using the reducing dopant layer as a charge generating layer, it is possible to manufacture an organic electroluminescent device emitting white light having two or more light emitting layers.

Formation of each layer of the organic electroluminescent device of the present application is a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, ink jet printing (ink jet printing), nozzle printing (nozzle printing), slot coating (slot coating), Any one of wet film forming methods such as spin coating, dip coating, and flow coating may be applied.

In the case of the wet film forming method, a thin film is formed by dissolving or dispersing the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, the solvent in which the material forming each layer is dissolved or dispersed. It can be, and any one may be used as long as there is no problem in the film-forming property.

When forming the at least one organic electroluminescent compound according to an example, it may be deposited by co-deposition or mixed deposition, but is not limited thereto. The co-deposition is a method of mixing two or more isomeric materials by putting two or more isomeric materials into each individual crucible source, evaporating the materials by applying an electric current to the two cells at the same time, and performing mixed deposition. After mixing in the crucible source, a current is applied to one cell to evaporate the material, thereby performing mixed deposition.

According to one embodiment, using the organic electroluminescent device of the present invention, a display device, for example, a display device for a smartphone, tablet, notebook, PC, TV or vehicle, or a lighting device, for example, outdoors or indoor It is possible to manufacture a content lighting device.

Hereinafter, for a detailed understanding of the present application, a method for preparing a compound according to the present application will be described by taking as an example a method for synthesizing a representative compound or an intermediate compound of the present application.

[Example 1] Preparation of compound C-1

1) Synthesis of compound 1-2

Compound 1-1 (141 g, 375 mmol) and 1.4 L of toluene were dissolved in a flask, _{and then 700 mL of 30% hydrogen peroxide (H 2} O ₂ ) was slowly added dropwise at room temperature, and then 200 mL of 35% sodium bisulfite aqueous solution was added. It was added dropwise slowly. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 1-2 (90 g, yield: 69%).

2) Synthesis of compound 1-3

Compound 1-2 (90 g, 258 mmol), 2-bromo-1-chloro-3-fluorobenzene (54 g, 258 mmol), potassium carbonate (K ₂ CO ₃ ) (53 g, 387 mmol) in a flask ), and 900 mL of n-methylpyrrolidone (NMP) were added and refluxed at 160° C. for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 1-3 (97 g, yield: 70%).

3) Synthesis of compound 1-4

In a flask, add compound 1-3 (100 g, 186 mmol), palladium acetate (Pd(OAc) ₂ ) (2 g, 9.3 mmol), tricyclohexyl phosphine (PCy ₃ ) (5.2 g, 18 mmol), potassium carbonate (77 g, 558 mmol), and 1.5 L of dimethylacetamide (DMAc) were added and reacted at 150° C. for 10 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 1-4 (43 g, yield: 50 %).

4) Synthesis of compound C-1

In a flask, compound 1-4 (8.0 g, 17.5 mmol), compound 1-5 (5.2 g, 21.0 mmol), tris(dibenzylideneacetone)dipalladium(0)(Pd ₂ dba ₃ ) (0.80 g, 0.88 mmol) (0.80 g, 0.88 mmol) ), tri-t-butylphosphine (P(tBu) ₃ ) (0.86 mL, 1.75 mmol in 50% toluene solution), sodium t-butoxide (NaOtBu) (3.4 g, 35 mmol), and 90 mL of toluene and refluxed at 110° C. for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent of the reaction mixture was removed using a rotary evaporator and purified by column chromatography to obtain a white solid compound C-1 (8.8 g, yield: 76%).

[Example 2] Preparation of compound C-2

In a flask, place compound 1-4 (8.0 g, 17.5 mmol), compound 1-6 (6.0 g, 21.0 mmol), Pd ₂ dba ₃ (0.80 g, 0.88 mmol), P(tBu) ₃ (0.86 mL, 1.75 mmol in 50% toluene solution), NaOtBu (3.4 g, 35 mmol), and 90 mL of toluene were added and refluxed at 110° C. for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent of the reaction mixture was removed using a rotary evaporator and purified by column chromatography to obtain a white solid compound C-2 (6.6 g, yield: 53%).

[Example 3] Preparation of compound C-3

In a flask, compound 1-4 (10.0 g, 21.9 mmol), compound 1-7 (9.49 g, 26.3 mmol), Pd ₂ dba ₃ (1.00 g, 1.09 mmol), P(tBu) ₃ (1.08 mL, 2.19 mmol, in 50% toluene solution), NaOtBu (4.21 g, 43.8 mmol), and 90 mL of toluene were added, and the mixture was refluxed at 110° C. for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent of the reaction mixture was removed using a rotary evaporator and purified by column chromatography to obtain a white solid compound C-3 (8.7 g, yield: 51%).

[Example 4] Preparation of compound C-6

In a flask, compound 1-4 (5.0 g, 10.9 mmol), compound 1-8 (2.95 g, 12.0 mmol), Pd ₂ dba ₃ (0.50 g, 0.55 mmol), P(tBu) ₃ (0.54 mL, 1.09 mmol, 50% toluene solution), NaOtBu (2.10 g, 21.9 mmol), and 55 mL of toluene were added and refluxed for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent of the reaction mixture was removed using a rotary evaporator and purified by column chromatography to obtain a white solid compound C-6 (3.4 g, yield: 47%).

[Example 5] Preparation of compound C-281

In a flask, compound 1-4 (10.0 g, 21.9 mmol), compound 1-9 (6.46 g, 21.9 mmol), Pd ₂ dba ₃ (1.00 g, 1.09 mmol), P(tBu) ₃ (1.08 mL, 2.19 mmol, 50% toluene solution), NaOtBu (4.21 g, 43.8 mmol), and 110 mL of toluene were added and refluxed for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the solvent of the reaction mixture was removed using a rotary evaporator, and purified by column chromatography to obtain a white solid compound C-281 (9.0 g, yield: 57%).

Hereinafter, light emitting characteristics of an organic electroluminescent device including the organic electroluminescent compound of the present application will be described for a detailed understanding of the present application.

[Device Example 1] Preparation of a green light emitting organic electroluminescent device according to the present invention

OLEDs according to the invention were prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (Giomatec) substrate was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropanol and stored before use. Next, after mounting the ITO substrate in the substrate holder of the vacuum deposition equipment, the compound HI-1 is put into a cell in the vacuum deposition equipment, the compound HT-1 is put into another cell, and the two materials are evaporated at different rates. Based on the total amount of the material, compound HI-1 was doped in an amount of 3 wt% to deposit a 10 nm thick first hole injection layer. Then, a compound HT-1 as a first hole transport layer was deposited on the first hole injection layer to a thickness of 80 nm. Then, the compound C-1 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 30 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. After putting H-1 and H-2 as hosts in two cells in the vacuum deposition equipment, and D-130 as a dopant in another cell, the two host materials were evaporated at a different rate of 2:1 and at the same time A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by evaporating the dopant material at different rates and doping the dopant in an amount of 10% by weight based on the total amount of the host and the dopant. Then, on the light emitting layer, the compound ETL-1 : EIL-1 as an electron transport material was doped in a weight ratio of 40:60 to deposit an electron transport layer having a thickness of 35 nm. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED.

[Device Example 2] Preparation of green light emitting organic electroluminescent device according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that Compound C-2 was used as the material for the second hole transport layer.

[Device Example 3] Preparation of green light emitting organic electroluminescent device according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that Compound C-3 was used as the material for the second hole transport layer.

[Device Example 4] Preparation of a green light emitting organic electroluminescent device according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that Compound C-6 was used as the material for the second hole transport layer.

[Device Comparative Example 1] Preparation of a green light emitting organic electroluminescent device not according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that compound HT-1 was used as the material for the second hole transport layer.

[Device Comparative Example 2] Preparation of a green light emitting organic electroluminescent device not according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that compound HT-2 was used as the material for the second hole transport layer.

The driving voltage, luminous efficiency, and CIE color coordinates based on 1,000 nits luminance of the organic electroluminescent device according to the device examples and device comparative examples prepared as described above were measured, and the results are shown in Table 1 below.

From Table 1, it can be seen that the organic electroluminescent device including the organic electroluminescent compound according to the present invention as a hole transport material exhibits lower driving voltage and high luminous efficiency characteristics, compared to a device including a conventional hole transport material. .

The compounds used in the device examples and device comparative examples are specifically shown in Table 2 below.

Claims (7)

An organic electroluminescent compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X and Y are each independently O or S;
L ₁ is a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₂ -N-(Ar ₃ )(Ar ₄ ); may be joined with adjacent substituents to form a ring;
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 (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, or -L ₃ -N-(Ar ₅ )(Ar ₆ ); may be linked to adjacent substituents to form a ring;
L ₂ and L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
Ar ₃ to Ar ₆ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted a fused ring group of a cyclic (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or a substituted or unsubstituted (3-30 membered) heteroaryl;
a to c are each independently an integer from 1 to 4, d is an integer from 1 to 3;
When a to d are each independently, an integer of 2 or more, each of R ₁ to R ₄ may be the same as or different from each other. The organic electroluminescent compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-4:
[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

In Formulas 1-1 to 1-4,
R ₁ to R ₄ , X, Y, L ₁ , Ar ₁ , Ar ₂ , and a to d are each independently the same as defined in claim 1. 3. The method of claim 2,
L ₁ is a single bond or a substituted or unsubstituted (C6-C30)arylene;
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or a substituted or unsubstituted (C3-C30) aliphatic ring And (C6-C30) is a fused ring group of the aromatic ring, an organic electroluminescent compound. 4. The substituted cycloalkylene of claim 1, wherein substituted alkyl, substituted alkylene, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene , substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the substituents of the fused ring group of the substituted aliphatic ring and the aromatic ring are each independently deuterium ; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (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 membered) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (5-50 membered)heteroaryl unsubstituted or substituted with one or more of (C1-C30)alkyl, (C6-C30)aryl and di(C6-C30)arylamino; (C6-C30)aryl unsubstituted or substituted with one or more of (C1-C30)alkyl, (3-50 membered)heteroaryl, and mono- or di- (C6-C30)arylamino; 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- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino substituted or unsubstituted with one or more of (C1-C30)alkyl, (5-30 membered)heteroaryl and di(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30)arylphosphinyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And at least one selected from the group consisting of (C1-C30)alkyl (C6-C30)aryl, an organic electroluminescent compound. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 . The organic electroluminescent device according to claim 6, comprising the organic electroluminescent compound in a hole transport zone.

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