KR20200101740A - 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 disclosure, the organic electroluminescent device having improved driving voltage, luminous efficiency, lifetime characteristics, and/or power efficiency may be provided.

Description

An organic electroluminescent compound and an organic electroluminescent device containing the same TECHNICAL FIELD [ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

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

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

The most important factor determining luminous efficiency in an organic electroluminescent device is a light-emitting material. Fluorescent materials have been widely used as luminescent materials until now. However, due to the mechanism of electroluminescence, phosphorescent luminescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescent materials. Has become. Until now, iridium (III) complex series are widely known as phosphorescent materials, and for each RGB, bis(2-(2'-benzothienyl)-pyridinato-N,C-3') iridium (acetylacetonate ) [(acac)Ir(btp) ₂ ], tris(2-phenylpyridine)iridium [Ir(ppy) ₃ ] and bis(4,6-difluorophenylpyridinato-N,C2)picolinei Materials such as toiridium (Firpic) are known.

In the prior art, 4,4'-N,N'-dicarbazole-biphenyl (CBP) was most widely known as a host material for phosphorescence. Recently, Bathocuproine (BCP) and aluminum (III) bis(2-methyl-8-quinolinate) (4-phenylphenolate), which were used as materials for hole blocking layers by Japanese pioneers and the like ( Balq) has been used as a host material to develop a high-performance organic electroluminescent device.

However, conventional materials have advantages in terms of light-emitting properties, but have the following disadvantages: (1) The glass transition temperature is low and thermal stability is low, so that it deteriorates during a high-temperature evaporation process under vacuum, and the life of the device is reduced. (2) In an organic electroluminescent device, power efficiency = [(π/voltage) × current efficiency], so the power efficiency is inversely proportional to the voltage. The organic electroluminescent device using a phosphorescent host material is an organic electric field using a fluorescent material. Compared to the light emitting device, the current efficiency (cd/A) is high, but the driving voltage is also considerably high, so there is no significant advantage in terms of power efficiency (lm/w). (3) In addition, when used in an organic electroluminescent device, the operating life is not satisfactory, and the luminous efficiency is still required to be improved.

Various materials or concepts have been proposed for an organic layer of an organic electroluminescent device in order to improve luminous efficiency, driving voltage, and/or lifetime, but they are not satisfactory for practical use.

Korean Patent Publication No. 2018-0012709 discloses a compound having a fused structure including indolocarbazole and azepine, but does not specifically disclose a compound in which an aryl or heteroaryl is bonded to the core structure.

Korean Patent Publication No. 2018-0012709 (published on February 6, 2018)

The object of the present application is to firstly provide an organic electroluminescent compound effective in manufacturing an organic electroluminescent device having improved driving voltage, luminous efficiency, life characteristics and/or power efficiency, and secondly, comprising the organic electroluminescent compound It is to provide an organic electroluminescent device.

Specifically, the present inventors completed the present invention by discovering that the organic electroluminescent compound represented by the following formula (1) achieves the above object.

[Formula 1]

In Formula 1,

X ₁ to X ₁₃ are each independently N or CR ₁ , and at least one of X ₁ to X ₁₃ is CR ₁ ;

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

R ₁ 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) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ; Adjacent substituents may be linked to each other to form a ring;

When R ₁ is plural, each R ₁ may be the same or different from each other, and at least one R ₁ is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) hetero Aryl;

Ar 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, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ;

R ₂ to R ₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl , Or a substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked with an adjacent substituent to form a ring, and when R ₂ to R ₆ are plural, each of R ₂ to R ₆ may be the same or different from each other. Can;

a is an integer of 1 to 3, and when a is 2 or more, each Ar may be the same or different.

When the organic electroluminescent compound according to the present application is used, it is possible to manufacture an organic electroluminescent device having a low driving voltage, high luminous efficiency, excellent lifetime characteristics, and/or high power efficiency.

1 is a representative formula of an organic electroluminescent compound of 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" refers to a compound that can be used in an organic electroluminescent device, and may 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 for an organic electroluminescent device, 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 be 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, an electron buffer material, a hole blocking material, an electron transmission material, an electron injection material. have.

The organic electroluminescent material of the present application may include one or more compounds represented by Formula 1 above. Although not limited thereto, the compound of Formula 1 may be included in the light emitting layer, the electron transport layer, and/or the electron buffer layer. When included in the emission layer, the compound of Formula 1 may be included as a host material. Here, the host material may be a host material of a green or red light-emitting organic electroluminescent device. In addition, when included in the electron transport layer, the compound of Formula 1 may be included as an electron transport material, and when included in the electron buffer layer, the compound of Formula 1 may be included as an electron buffer material.

The compound represented by Formula 1 will be described in more detail as follows.

As used herein, "(C1-C30)alkyl" refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting a chain, wherein the carbon number is preferably 1 to 20, more preferably 1 to 10. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C2-C30)alkenyl" refers to a straight or branched alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20, more preferably 2 to There are 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbut-2-enyl. As used herein, "(C2-C30)alkynyl" refers to a straight or branched alkynyl having 2 to 30 carbon atoms constituting a chain, wherein the carbon number is preferably 2 to 20, more preferably 2 to There are 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 (ene)" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, and the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7 It's a dog. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7, preferably 5 to 7 ring skeleton atoms, and the 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 (ene)" refers to a monocyclic or fused cyclic radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated. The number of ring skeleton carbon atoms 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, benzofluorenyl, dibenzoflu Orenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azule Neil and others. More specifically, examples of the aryl include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, benzanthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, naphthacenyl group, pyrenyl group, 1-chrycenyl group, 2-chrycenyl group, 3-chrycenyl group, 4 -Chrysenyl group, 5-crycenyl group, 6-crycenyl group, benzo[c]phenanthryl group, benzo[g]chrycenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-tri Phenylenyl group, 4-triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, benzofluorenyl group, dibenzofluore Nyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-terphenyl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2- Diary, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-quaterphenyl group, 3-fluoranthenyl group, 4-fluoranthenyl group, 8- Fluoranthenyl group, 9-fluoranthenyl group, benzofluoranthenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5 -Xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, pt-butylphenyl group, p-(2-phenylpropyl)phenyl group, 4'-methylbiphenylyl group, 4"-t- Butyl-p-terphenyl-4-yl group, 9,9-dimethyl-1-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-dimethyl-3-fluorenyl group, 9,9 -Dimethyl-4-fluorenyl group, 9,9-diphenyl-1-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-3-fluorenyl group, 9, And 9-diphenyl-4-fluorenyl group.

As used herein, "(3-30 membered) heteroaryl (ene)" refers to an aryl group having 3 to 30 ring skeleton atoms and including at least one heteroatom 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 condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein includes one or more heteroaryl or aryl groups connected to a heteroaryl group by a single bond, and includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and other single ring heteroaryl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, iso Quinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazolyl, phenothiazinyl, Fused ring heteroaryl such as phenanthridinyl, benzodioxolyl, dihydroacridinyl, and the like. More specifically, examples of the heteroaryl include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5- Pyrimidinyl group, 6-pyrimidinyl group, 1,2,3-triazine-4-yl group, 1,2,4-triazine-3-yl group, 1,3,5-triazin-2-yl group, 1 -Imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7 -Indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group , 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group , 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7- Isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group , 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3 -Quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4 -Isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxali Nyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazolyl-1-yl group, azacarbazolyl -2-yl group, azacarbazolyl-3-yl group, azacarbazolyl-4-yl group, azacarbazolyl-5-yl group, azacarbazolyl-6-yl group, azacarbazolyl-7-yl group, Azacarbazolyl-8-yl group, azacarbazolyl-9-yl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6 -Phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridy Nyl group, 4-acridinyl group, 9-acridinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furaza Nyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3- Methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3-(2- Phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl -1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group, 4-t-butyl-3-indolyl group, 1-dibenzofuranyl group, 2-dibenzo Furanyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-silafluore Nyl group, 2-silafluorenyl group, 3-silafluorenyl group, 4-silafluorenyl group, 1-germafluorenyl group, 2-germafluorenyl group, 3-germafluorenyl group, 4-ger Mafluorenyl group, etc. are mentioned. "Halogen" herein includes F, Cl, Br and I atoms.

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

In addition, in the description of "substituted or unsubstituted" as described herein, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a functional group. Herein substituted (C1-C30)alkyl, substituted (C6-C30)aryl (ene), substituted (3-30 membered) heteroaryl (ene), substituted (C3-C30)cycloalkyl (ene), Substituted (C1-C30)alkoxy, substituted tri(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30) ) Arylsilyl, substituted tri (C6-C30) arylsilyl, substituted mono- or di- (C1-C30) alkylamino, substituted mono- or di- (C6-C30) arylamino and substituted (C1- The substituents of C30)alkyl(C6-C30)arylamino 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 member) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30) heteroaryl unsubstituted or substituted with aryl; (C6-C30)aryl unsubstituted or substituted with (5-30 membered) heteroaryl; 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)arylboronyl; Di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And (C1-C30) alkyl (C6-C30) is at least one selected from the group consisting of aryl, and according to an embodiment of the present application, the substituents are each independently one or more (C1-C6) alkyl, (C6-C15) Aryl, (5-15 membered) heteroaryl and/or (C1-C6)alkyl(C6-C15)aryl. Specifically, the substituents may each independently be one or more methyl, tert butyl, phenyl, biphenyl, dimethylfluorenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl and/or carbazolyl.

The compound of Formula 1 may be represented by the following Formula 1-1.

[Formula 1-1]

In Formula 1-1,

L, Ar and a are as defined in Formula 1;

R _a to R _m 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, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ; Adjacent substituents may be linked to each other to form a ring; Provided that at least one of R _a to R _m is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

R ₂ to R ₆ are as defined in Formula 1.

In Formula 1, X ₁ to X ₁₃ are each independently N or CR ₁ , and at least one of X ₁ to X ₁₃ is CR ₁ .

In Formula 1, L is a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cyclo Alkylene, preferably a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5-20 membered) heteroarylene, more preferably a single bond, unsubstituted (C6-C15)arylene, or (5-20 membered) heteroarylene unsubstituted or substituted with one or more (C1-C6)alkyl. The heteroarylene may include one or more of nitrogen, oxygen, and sulfur. According to one aspect of the present application, L is a single bond, phenylene, naphthylene, pyridylene, pyrimidinylene, triazinylene, quinolinylene, quinazolinylene, quinoxalinylene, naphthyridinylene, carbazolylene, benzo Furopyrimidinylene, benzothienopyrimidinylene, dimethyl indenopyrimidinylene, benzoquinoxalinylene, benzocarbazolylene, and the like.

In Formula 1, R ₁ 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) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ; Adjacent substituents may be linked to each other to form a ring. When R ₁ is plural, each R ₁ may be the same or different from each other, and at least one R ₁ is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) hetero It is aryl.

R ₁ is preferably each independently hydrogen, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-15 membered) heteroaryl, and more preferably each independently hydrogen; (C6-C30)aryl unsubstituted or substituted with one or more (C1-C6)alkyl, (5-15 membered)heteroaryl and/or (C1-C6)alkyl(C6-C15)aryl; Or one or more (C6-C15) aryl substituted or unsubstituted (5-15 membered) heteroaryl. According to an aspect of the present application, R ₁ is each independently hydrogen, phenyl, naphthyl, biphenyl, terphenyl, quarterphenyl, phenyl substituted with dimethylfluorenyl, phenyl substituted with dibenzofuranyl, carbazolylo Substituted phenyl, biphenyl substituted with dimethylfluorenyl, biphenyl substituted with dibenzofuranyl, biphenyl substituted with dibenzothiophenyl, pyridinyl, pyridinyl substituted with biphenyl, substituted with one or more phenyl Triazinyl, quinazolinyl substituted with phenyl, carbazolyl substituted with phenyl, and the like.

In Formula 1, Ar 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)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ .

Ar is preferably substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-20 membered) heteroaryl, or -NR ₅ R ₆ , more preferably (C1-C6) alkyl (C6-C30)aryl unsubstituted or substituted with; (5-20 membered) heteroaryl unsubstituted or substituted with one or more (C6-C12)aryl and/or (5-15 membered) heteroaryl; Or -NR ₅ R ₆ . According to one aspect of the present application, Ar is phenyl, naphthyl, biphenyl, terphenyl, phenyl substituted with tert butyl, diphenylfluorenyl, pyridinyl, triazinyl substituted with one or more phenyl, phenyl and pyridinyl. Substituted triazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl substituted with phenyl, benzonaphthofuranyl, diphenylamino, and the like.

In Formula 1, R ₂ to R ₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl, or may be linked to each other with adjacent substituents to form a ring, and when R ₂ to R ₆ are plural, each of R ₂ to R ₆ May be the same as or different from each other, preferably each independently a substituted or unsubstituted (C6-C12)aryl, more preferably each independently an unsubstituted (C6-C12)aryl. According to an aspect of the present application, R ₂ to R ₆ may each independently be phenyl or the like.

In Formula 1, a is an integer of 1 to 3, and when a is 2 or more, each Ar may be the same or different. According to an aspect of the present application, a is 1 or 2.

According to an aspect of the present disclosure, in Formula 1, Ar and R ₁ may each independently be selected from hydrogen or any one of the substituents listed in Group 1 below. At this time, at least one R ₁ is selected from the following group 1.

[Group 1]

In group 1 above,

D1 and D2 are each independently a benzene ring or a naphthalene ring;

X ₂₁ is O, S, NR ₂₂ , or CR ₂₃ R ₂₄ ;

Each X ₂₂ is independently CR ₃₁ or N, provided that at least one of X ₂₂ is N;

Each X ₂₃ is independently CR ₃₂ or N;

L ₁₁ to L ₁₃ and L ₁₅ to L ₁₈ are each independently a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;

L ₁₄ is a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;

R ₁₁ to R ₂₄ , R ₃₁ and R ₃₂ 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, or substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked to adjacent substituents to form a substituted or unsubstituted ring;

aa, ff, and gg are each independently an integer of 1 to 5, bb is an integer of 1 to 7, and cc, dd and ee are each independently an integer of 1 to 4.

According to another aspect of the present disclosure, in Formula 1, Ar and R ₁ may each independently be selected from hydrogen or any one of the substituents listed in Group 2 below. At this time, at least one R ₁ is selected from Group 2 below.

[Group 2]

In group 2 above,

L ₁ is the same as the definition of L in Formula 1;

A ₁ to A ₃ are each independently a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl.

According to another aspect of the present application, in Formula 1, Ar and R ₁ may each independently be selected from hydrogen or any one of the substituents listed in Group 3 below. At this time, at least one R ₁ is selected from Group 3 below.

[Group 3]

According to one embodiment of the present application, X ₁ to X ₁₃ are each independently N or CR ₁ , and at least one of X ₁ to X ₁₃ is CR ₁ ; L is a single bond, a substituted or unsubstituted (C6-C15) arylene, or a substituted or unsubstituted (5-20 membered) heteroarylene; Each R ₁ is independently hydrogen, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5-15 membered) heteroaryl; Provided that at least one R ₁ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Ar is substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-20 membered)heteroaryl, or -NR ₅ R ₆ ; R ₂ to R ₆ are each independently substituted or unsubstituted (C6-C12)aryl; a is 1 or 2.

According to another embodiment of the present application, X ₁ to X ₁₃ are each independently N or CR ₁ , and at least one of X ₁ to X ₁₃ is CR ₁ ; L is a single bond, unsubstituted (C6-C15)arylene, or (5-20 membered) heteroarylene substituted or unsubstituted with one or more (C1-C6)alkyl; Each R ₁ is independently each independently hydrogen; (C6-C30)aryl unsubstituted or substituted with one or more (C1-C6)alkyl, (5-15 membered)heteroaryl and/or (C1-C6)alkyl(C6-C15)aryl; Or (5-15 membered) heteroaryl unsubstituted or substituted with one or more (C6-C15)aryl; Provided that at least one R ₁ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Ar is (C6-C30)aryl unsubstituted or substituted with (C1-C6)alkyl; (5-20 membered) heteroaryl unsubstituted or substituted with one or more (C6-C12)aryl and/or (5-15 membered) heteroaryl; Or -NR ₅ R ₆ ; R ₂ to R ₆ are each independently unsubstituted (C6-C12)aryl; a is 1 or 2.

In the present formula, when adjacent substituents are linked to each other to form a ring, the ring may be a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof. In addition, the formed ring may contain one or more heteroatoms selected from nitrogen, oxygen and sulfur. 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 non-substituted 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 formula herein, the heteroaryl (ene) 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 (5-30 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, 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(C6-30)aryl One or more substituents selected from the group consisting of amino may be bonded.

The compound represented by Formula 1 may be specifically exemplified as the following compound, but is not limited thereto.

The compound of Formula 1 according to the present application can be prepared by a synthetic method known to those skilled in the art based on the contents described in KR 2018-0012709 A, for example, it can be prepared as shown in the following scheme.

[Scheme 1]

In Reaction Scheme 1, X ₁ to X ₁₃ , L, Ar, and a are the same as defined in Formula 1.

Exemplary synthesis examples of the present invention represented by Formula 1 have been described above, but these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, 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 are bonded in addition to the substituents specified in

The present application provides an organic electroluminescent material including the organic electroluminescent compound of Formula 1 and an organic electroluminescent device including the material.

The material may be formed 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 compound of Formula 1 of the present application includes the emission layer, hole injection layer, hole transport layer, hole auxiliary layer, light emission auxiliary layer, electron transport layer, electron buffer layer, electron injection layer, interlayer, hole blocking layer, and It may be included in one or more of the electron blocking layers. In some cases, preferably, it may be included in the light emitting layer. When used in the light emitting layer, the organic electroluminescent compound of Formula 1 herein may be included as a host material. Preferably, the emission layer may further include one or more dopants. If necessary, the organic electroluminescent compound of the present application can be used as a co-host material. That is, the emission layer may further include an organic electroluminescent compound other than the organic electroluminescent compound (first host material) of Formula 1 of the present application as the second host material. In this case, the weight ratio of the first host material and the second host material is in the range of 1:99 to 99:1. When two or more types of materials are included in one layer, a layer may be formed by mixed deposition, or co-deposited separately at the same time to form a layer.

Any known host material may be used as the second host material, and it may be preferably selected from the group consisting of compounds represented by the following Chemical Formulas 11 to 16.

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

In Formulas 11 to 15,

Cz is the following structure,

A is -O- or -S-;

R ₄₁ to R ₄₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 membered) Heteroaryl or -SiR ₄₅ R ₄₆ R ₄₇ , and R ₄₅ to R ₄₇ are each independently substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C6-C30)aryl; L ₄ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y ₁ and Y ₂ are each independently -O-, -S-, -N(R ₅₁ )-, or -C(R ₅₂ )(R ₅₃ )-, and Y ₁ and Y ₂ are not simultaneously present; R ₅₁ to R ₅₃ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl, and R ₅₂ and R ₅₃ may be the same or different; h and i are each independently an integer of 1 to 3, j, k, l and m are each independently an integer of 1 to 4, q is an integer of 1 to 3, h, i, j, k, l , when m or q is an integer of 2 or more, each (Cz-L ₄ ), each (Cz), each R ₄₁ , each R ₄₂ , each R ₄₃ or each R ₄₄ may be the same or different .

[Formula 16]

In Chemical Formula 16,

Y ₃ to Y ₅ are each independently CR ₅₄ or N;

R ₅₄ is hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5-30 membered)heteroaryl;

B ₁ and B ₂ are each independently hydrogen, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

B ₃ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

L ₅ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene.

Specifically, examples of the second host material are as follows, but is not limited thereto.

[Here, TPS is a triphenylsilyl group]

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

The dopant included in the organic electroluminescent device of the present application may include, for example, a compound represented by Formula 101, but is not limited thereto.

[Formula 101]

In Chemical Formula 101,

L'is selected from the following structures 1 or 2;

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

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, 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 are adjacent substituents connected to each other to form a substituted or unsubstituted fused ring with pyridine, for example, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted Substituted 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, 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 are adjacent substituents connected to each other to form a substituted or unsubstituted fused ring with benzene, for example, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted It is possible to form a substituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothienopyridine;

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

n is an integer of 1 to 3.

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

The organic electroluminescent device according to the present application includes a first electrode; A second electrode; And at least one organic material layer 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 an emission layer, and is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission 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 floors. Each of the layers may be further composed of several layers.

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. Depending on 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-side emission type. In addition, the hole injection layer may be additionally doped with a p-dopant, and the electron injection layer may be additionally doped with an n-dopant.

The organic material layer may further include at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound.

In addition, in the organic electroluminescent device of the present application, the organic material layer is at least one metal selected from the group consisting of group 1, group 2, period 4 transition metal, period 5 transition metal, lanthanum metal and organometals of d-transition elements, Alternatively, it may further include one or more complex compounds containing such metals.

In addition, the organic electroluminescent device of the present application may emit white light by further including at least one emission layer including a blue, red, or green emission compound known in the art in addition to the compound of the present disclosure. In addition, if necessary, a yellow or orange light emitting layer may be further included.

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 referred to as "surface layer" It is desirable to place ). Specifically, it is preferable to provide a silicon and aluminum chalcogenide (including oxide) layer on the surface of the anode on the side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer on the surface of the cathode on the side of the light-emitting medium layer. Stabilization of driving of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide include SiO _X (1≤X≤2), AlO _X (1≤X≤1.5), SiON, SiAlON, etc., and preferred examples of the metal halide are LiF, MgF ₂ , CaF ₂ , fluoride Rare earth metals and the like, and preferred examples of metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

A hole injection layer, a hole transport layer or an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. For the hole injection layer, a plurality of layers may be used for the purpose of lowering a hole injection barrier (or a hole injection voltage) from an anode to a hole transport layer or an electron blocking layer, and two compounds may be used simultaneously for each layer. A plurality of layers may be used for the hole transport layer or the electron blocking layer.

An electron buffer layer, a hole blocking layer, an electron transport layer or 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 simultaneously for each layer. 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.

The light emitting auxiliary layer is a layer positioned between the anode and the light emitting layer, or between the cathode and the light emitting layer, and when positioned between the anode and the light emitting layer, it facilitates injection and/or transfer of holes or blocks overflow of electrons. When used for a purpose, or when positioned between the cathode and the light emitting layer, it can be used to facilitate injection and/or transmission of electrons or to block overflow of holes. In addition, the hole auxiliary layer is located between the hole transport layer (or the hole injection layer) and the light emitting layer, and may exhibit an effect of smoothing or blocking a hole transfer rate (or injection rate), and accordingly, a charge balance ) Can be adjusted. In addition, the electron blocking layer is a layer positioned between the hole transport layer (or hole injection layer) and the emission layer, and blocks the overflow of electrons from the emission layer to confine excitons in the emission layer to prevent leakage of light. When two or more hole transport layers are included, an additional layer may be used as the hole auxiliary layer or the electron blocking layer. The hole auxiliary layer and the electron blocking layer have an effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

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 the pair of electrodes. In this way, since the electron transfer compound is reduced to an anion, it becomes 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 become a cation, it becomes easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferable reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, it is possible to manufacture an organic electroluminescent device emitting white light having two or more light emitting layers by using the reducing dopant layer as a charge generating layer.

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

The formation of each layer of the organic electroluminescent device of the present application can be performed by any one of a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, or a wet film deposition method such as spin coating, dip coating, and flow coating. Can be applied. When forming a film of the first host compound and the second host compound of the present application, a process is performed by co-deposition or mixed evaporation.

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

In addition, a display device, for example, a smart phone, tablet, notebook, PC, TV or vehicle display device, or a lighting device, for example, an outdoor or indoor lighting device is manufactured using the organic electroluminescent device of the present application. It is possible to do.

In the following, for a detailed understanding of the present application, a method for preparing a compound according to the present application and its physical properties are shown, including the representative compound of the present application. However, the present invention is not limited to the following examples.

[ Example 1] Preparation of compound C-74

1) Synthesis of compound 3

In a flask, compound 1 (50.0 g, 205.7 mmol), compound 2 (87.0 g, 308.5 mmol), CuSO ₄ (16.4 g, 102.9 mmol) and K ₂ CO ₃ (56.9 g, 411.4 mmol) were added to 1,2-dichlorobenzene. After dissolving in 1000 mL, it was stirred under reflux for one day. The mixture was distilled to remove the solvent, and then separated by column chromatography to obtain compound 3 (71.9 g, yield: 88%).

2) Synthesis of compound 4

After adding 450 mL of toluene and 450 mL of tetrahydrofuran (THF) to a flask, n-BuLi (100.0 mL, 252.7 mmol) was added dropwise thereto at -78°C. Compound 3 (71.9 g, 180.5 mmol) and B(OiPr) ₃ (62.0 mL, 270.8 mmol) were added thereto, followed by reflux stirring at room temperature for one day. After completion of the reaction, the mixture was extracted with EA/H ₂ O and concentrated to obtain compound 4 (49.4 g, yield: 75%).

3) Synthesis of compound 6

In a flask, compound 4 (47.4 g, 316.8 mmol), compound 5 (62.0 g, 261.0 mmol), K ₂ CO ₃ (45.0 g, 326.3 mmol), o-xylene 650 mL, 1,4-dioxane 160 mL, and After adding 160 mL of H ₂ O, the mixture was stirred under reflux at 200°C for 18 hours. After completion of the reaction, it was extracted with EA/H ₂ O and separated by column chromatography to give compound 6 (47.9 g, yield: 77%).

4) Synthesis of compound 7

In a flask, compound 6 (49.3 g, 103.8 mmol), Pd(OAc) ₂ (2.3 g, 10.4 mmol), tricyclohexylphosphonium tetrafluoroborate (7.5 g, 20.8 mmol), Cs ₂ CO ₃ (101.5 g, 311.4 mmol) and 520 mL of o-xylene were added, followed by reflux stirring for 3 hours and 30 minutes. After completion of the reaction, the mixture was extracted with EA/H ₂ O and separated by column chromatography to obtain compound 7 (38.1 g, yield: 84%).

5) Synthesis of compound 8

Compound 7 (38.1 g, 86.9 mmol), PPh ₃ (57.0 g, 217.2 mmol) and 440 mL of 1,2-dichlorobenzene were added to the flask, followed by reflux stirring for 17 hours. After completion of the reaction, the mixture was distilled and then separated by column chromatography to obtain compound 8 (29.5 g, yield: 84%).

6) Synthesis of Compound C-74

Compound 8 (5.0 g, 12.3 mmol), compound 9 (4.4 g, 18.5 mmol), DMAP (0.75 g, 6.2 mmol), Cs ₂ CO ₃ (6.0 g, 18.5 mmol) and 62 mL of DMSO were added dropwise to a flask, and 100 It was stirred at °C for 1 hour. After completion of the reaction, the mixture was extracted with EA/H ₂ O and separated by column chromatography to obtain compound C-74 (5.8 g, yield: 77%).

[ Example 2] Preparation of compound C-13

In a flask, compound 10 (4.2 g, 10 mmol), 2-chloro-3-phenylquinoxaline (7.4 g, 30.7 mmol), dimethylaminopyridine (DMAP) (1.262 g, 10 mmol), cesium carbonate (Cs ₂ CO ₃₎ ) (40.4 g, 124 mmol) and 50 mL of dimethyl sulfoxide (DMSO) were added and stirred under reflux for 24 hours. After completion of the reaction, the mixture was extracted with ethyl acetate (EA)/H ₂ O and separated by column chromatography to obtain compound C-13 (2.0 g, yield: 32%).

[device Manufacturing example 1] Depositing the compound according to the present application as a host OLED Device fabrication

An OLED device comprising the compound according to the present application was prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (manufactured by Geomatech) substrate was subjected to ultrasonic cleaning by sequentially using acetone, ethanol and distilled water, and then stored in isopropyl alcohol and used. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, insert the compound HI-1 into the cell in the vacuum evaporation equipment, evacuate until the vacuum level in the chamber reaches 10 ^-6 torr, and then apply a current to the cell. Then, evaporation was performed to deposit a first hole injection layer having a thickness of 80 nm on the ITO substrate. Subsequently, compound HI-2 was put into another cell in a vacuum deposition equipment, and a second hole injection layer having a thickness of 5 nm was deposited on the first hole injection layer by evaporation by applying a current to the cell. Subsequently, 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 first hole transport layer having a thickness of 10 nm on the second hole injection layer. Subsequently, compound HT-2 was placed in another cell in a vacuum deposition equipment, and a second hole transport layer having a thickness of 60 nm was deposited on the first hole transport layer by evaporating by applying a current to the cell. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. After putting the compound of Table 1 as a host in one cell of the vacuum deposition equipment and compound D-39 as a dopant in the other cell, the two materials were evaporated at different rates and doped in an amount of 3% by weight, respectively. 2 A light emitting layer having a thickness of 40 nm was deposited on the hole transport layer. Then, addition of other cells Compound ET-1 and Compound EI -1 in two places 1: 1 was deposited by evaporation at a rate of the electron transport layer of 35 nm of thickness on the light emitting layer. Subsequently, after depositing compound EI- 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 other vacuum deposition equipment to manufacture an OLED device. I did.

[ Comparative example 1 and 2] deposited comparative compound as host OLED Device fabrication

An OLED device was manufactured in the same manner as in Device Manufacturing Example 1, except that the compound of Table 1 was used as the host of the light emitting layer.

The driving voltage based on 1,000 nit luminance, luminous efficiency, CIE color coordinates, and light intensity based on 5,000 nit luminance of the organic electroluminescent devices of Preparation Example 1 and Comparative Examples 1 and 2 prepared as described above were from 100% to 95%. The time taken to fall off (life: T95) is shown in Table 1 below.

[Table 1]

The organic electroluminescent device using the organic electroluminescent compound according to the present application as a host showed a driving voltage equal to or higher than that of the organic electroluminescent device using the compound of Comparative Example, luminous efficiency equal to or higher, and excellent lifetime characteristics.

[Table 2]

Claims (10)

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

In Formula 1,
X ₁ to X ₁₃ are each independently N or CR ₁ , and at least one of X ₁ to X ₁₃ is CR ₁ ;
L is a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
R ₁ 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) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ; Adjacent substituents may be linked to each other to form a ring;
When R ₁ is plural, each R ₁ may be the same or different from each other, and at least one R ₁ is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) hetero Aryl;
Ar 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, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ;
R ₂ to R ₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl , Or a substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked with an adjacent substituent to form a ring, and when R ₂ to R ₆ are plural, each of R ₂ to R ₆ may be the same or different from each other. Can;
a is an integer of 1 to 3, and when a is 2 or more, each Ar may be the same or different. The organic electroluminescent compound of claim 1, wherein the formula 1 is represented by the following formula 1-1:
[Formula 1-1]

In Formula 1-1,
L, Ar and a are as defined in claim 1;
R _a to R _m 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, -SiR ₂ R ₃ R ₄ , or -NR ₅ R ₆ ; Adjacent substituents may be linked to each other to form a ring; Provided that at least one of R _a to R _m is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
R ₂ to R ₆ are as defined in claim 1. The method of claim 1, wherein in L, Ar and R ₁ to R ₆ , substituted (C1-C30)alkyl, substituted (C6-C30)aryl (ene), substituted (3-30 membered) heteroaryl (ene ), substituted (C3-C30) cycloalkyl (ene) and substituted (C1-C30) alkoxy substituents 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 member) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30) heteroaryl unsubstituted or substituted with aryl; (C6-C30)aryl unsubstituted or substituted with (5-30 membered) heteroaryl; 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)arylboronyl; Di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And (C1-C30) alkyl (C6-C30) at least one selected from the group consisting of aryl, an organic electroluminescent compound. The method of claim 1, wherein Ar and R ₁ are each independently selected from hydrogen or any one of the substituents listed in the following group 1, provided that at least one R ₁ is selected from the following group 1, organic electroluminescence compound:
[Group 1]

In group 1 above,
D1 and D2 are each independently a benzene ring or a naphthalene ring;
X ₂₁ is O, S, NR ₂₂ , or CR ₂₃ R ₂₄ ;
Each X ₂₂ is independently CR ₃₁ or N, provided that at least one of X ₂₂ is N;
Each X ₂₃ is independently CR ₃₂ or N;
L ₁₁ to L ₁₃ and L ₁₅ to L ₁₈ are each independently a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;
L ₁₄ is a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;
R ₁₁ to R ₂₄ , R ₃₁ and R ₃₂ 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, or substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked to an adjacent substituent to form a substituted or unsubstituted ring;
aa, ff, and gg are each independently an integer of 1 to 5, bb is an integer of 1 to 7, and cc, dd and ee are each independently an integer of 1 to 4. The method of claim 1, wherein Ar and R ₁ are each independently selected from hydrogen or any one of the substituents listed in the following group 2, provided that at least one R ₁ is selected from the following group 2, organic electroluminescence compound:
[Group 2]

In group 2 above,
L ₁ is the same as the definition of L in claim 1;
A ₁ to A ₃ are each independently a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl. The organic electric field of claim 1, wherein Ar ₁ and R ₁ are each independently selected from hydrogen or any one of the substituents listed in the group 3 below, provided that at least one R ₁ is selected from the group 3 below. Luminous Compound:
[Group 3]

The organic electroluminescent compound of claim 1, wherein the compound represented by Formula 1 is selected from 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 9, wherein the organic electroluminescent compound is included in the emission layer.

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