JP2014531747A - NOVEL ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. Since the organic electroluminescent compound according to the present invention has high efficiency for transporting electrons, crystallization in the case of producing an element can be prevented. Furthermore, the compound has good layer formability and improves the current characteristics of the device. Thus, they can produce organic electroluminescent devices with low drive voltage and high power efficiency. [Selection figure] None

Description

  The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same.

  An electroluminescent (EL) device is a self-luminous device that offers advantages over other types of display devices in that it provides a wide viewing angle, a high contrast ratio, and has a faster response time. Organic EL devices were first developed by Eastman Kodak by using aromatic diamines and small molecules that are aluminum complexes as materials for forming the light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

The most important factor for determining the luminous efficiency in the organic EL element is the light emitting material. To date, fluorescent materials have been widely used as luminescent materials. However, in view of the electroluminescence mechanism, phosphorescent materials have been shown to theoretically increase luminous efficiency by a factor of four over fluorescent materials. Therefore, recently phosphorescent materials have been studied. Iridium (III) complexes are bis (2- (2′-benzothienyl) -pyridinate-N, C3 ′) iridium (acetylacetonate) ((acac) Ir (btp) as red, green and blue materials, respectively. ₂ ), phosphorescent materials including tris (2-phenylpyridine) iridium (Ir (ppy) ₃ ), and bis (4,6-difluorophenylpyridinate-N, C2) picolinate iridium (Firpic) Widely known. In particular, many phosphorescent materials have recently been studied in Japan, Europe, and the United States.

Currently, 4,4′-N, N′-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Furthermore, organic EL devices having high efficiency using batocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) for hole blocking layers are known. Pioneer (Japan) and others have developed a high-performance organic EL device using a BAlq derivative as a host material.

  Although these phosphorescent host materials provide good luminescent properties, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, during high temperature deposition processes in vacuum In addition, their decomposition can occur. (2) The power efficiency of the organic EL element is given by [(π / voltage) × current efficiency]. Since the power efficiency is inversely proportional to the voltage, the power efficiency should be increased to reduce power consumption. Organic EL devices containing phosphorescent materials provide much higher current efficiency (cd / A) than those containing fluorescent materials, but use conventional materials such as BAlq or CBP as phosphorescent host materials In this case, the driving voltage is significantly higher than that of an organic EL element using a fluorescent material. Thus, there is no advantage in terms of power efficiency (Lm / W). (3) Furthermore, the operating life of the organic EL element is short, and the light emission efficiency still needs to be improved.

  WO 2006/049013 discloses compounds for organic electroluminescent materials having bicyclic groups fused as skeletal structures. However, it does not disclose compounds having a fused bicyclic group containing nitrogen together with a carbazole group fused to an aromatic ring fused heterocycloalkyl or cycloalkyl group.

  An object of the present invention is to provide an organic electroluminescent compound having an excellent structure with high luminous efficiency and a long operating lifetime, suitable color adjustment, and high efficiency and a long lifetime using the compound. It is to provide an organic electroluminescence device having the same.

（式中、
Ｌ_１およびＬ_２は各々独立して、単結合、置換もしくは非置換３〜３０員ヘテロアリーレン基、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン基、または置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキレン基を表し、
Ｘ_１はＣＨまたはＮを表し、
Ｙ_１およびＹ_２は各々独立して、−Ｏ−、−Ｓ−、−ＣＲ_６Ｒ_７−または−ＮＲ_８−を表し、
Ｒ_１〜Ｒ_５は各々独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基、置換もしくは非置換３〜３０員ヘテロアリール基、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル基、置換もしくは非置換５〜７員ヘテロシクロアルキル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル基、−ＮＲ_１１Ｒ_１２、−ＳｉＲ_１３Ｒ_１４Ｒ_１５、−ＳＲ_１６、−ＯＲ_１７、シアノ基、ニトロ基、またはヒドロキシル基を表すか、あるいはＲ_４およびＲ_５は各々独立して、置換もしくは非置換（Ｃ３−Ｃ３０）アルキレンまたは置換もしくは非置換（Ｃ３−Ｃ３０）アルケニレン基を介して隣接する置換基（複数も含む）に結合して単環もしくは多環、脂環式環もしくは芳香環を形成し、その炭素原子（複数も含む）は、窒素、酸素および硫黄から選択される少なくとも１つのヘテロ原子で置換されてもよく、
Ｒ_６〜Ｒ_８およびＲ_１１〜Ｒ_１７は各々独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基、置換もしくは非置換３〜３０員ヘテロアリール基、置換もしくは非置換５〜７員ヘテロシクロアルキル基、または置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル基を表すか、あるいは置換もしくは非置換（Ｃ３−Ｃ３０）アルキレンまたは置換もしくは非置換（Ｃ３−Ｃ３０）アルケニレン基を介して隣接する置換基（複数も含む）に結合して単環もしくは多環、脂環式環もしくは芳香環を形成し、その炭素原子（複数も含む）は、窒素、酸素および硫黄から選択される少なくとも１つのヘテロ原子で置換されてもよく、
ａ、ｂ、ｃおよびｅは各々独立して１〜４の整数を表し、ａ、ｂ、ｃまたはｅが２以上の整数である場合、Ｒ_１の各々、Ｒ_２の各々、Ｒ_３の各々、またはＲ_５の各々は、同じまたは異なり、
ｄは１〜３の整数を表し、ｄが２以上の整数である場合、Ｒ_４の各々は同じまたは異なり、
ヘテロシクロアルキル基、およびヘテロアリール（アリーレン）基は、Ｂ、Ｎ、Ｏ、Ｓ、Ｐ（＝Ｏ）、ＳｉおよびＰから選択される少なくとも１つのヘテロ原子を含有する）
により達成され得ることを見出した。 The inventors of the present invention have an organic electroluminescent compound represented by the following formula 1 as described above:

(Where
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted 3 to 30 membered heteroarylene group, substituted or unsubstituted (C6-C30) arylene group, or substituted or unsubstituted (C3-C30) cycloalkylene Represents a group,
X ₁ represents CH or N;
Y ₁ and Y ₂ each independently represent —O—, —S—, —CR ₆ R ₇ — or —NR ₈ —,
R _{1 to} R ₅ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted 3 to 30 members. A heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl group, -NR ₁₁ R ₁₂ , —SiR ₁₃ R ₁₄ R ₁₅ , —SR ₁₆ , —OR ₁₇ , a cyano group, a nitro group, or a hydroxyl group, or R ₄ and R ₅ are each independently substituted or unsubstituted ( C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene group linked to adjacent substituent (s) Combine to form a monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur ,
R _{6 to} R ₈ and R _{11 to} R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or Represents an unsubstituted 3-30 membered heteroaryl group, a substituted or unsubstituted 5-7 membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group, or substituted or unsubstituted (C3-C30) Bonded to adjacent substituent (s) via alkylene or substituted or unsubstituted (C3-C30) alkenylene group to form a monocyclic or polycyclic, alicyclic or aromatic ring, and the carbon atom ( May also be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur,
a, b, c and e each independently represents an integer of 1 to 4, and when a, b, c or e is an integer of 2 or more, each of R ₁ , each of R ₂ and each of R ₃ Or each of R ₅ is the same or different,
d represents an integer of 1 to 3, and when d is an integer of 2 or more, each R ₄ is the same or different;
A heterocycloalkyl group and a heteroaryl (arylene) group contain at least one heteroatom selected from B, N, O, S, P (═O), Si and P)
It has been found that can be achieved.

  The organic electroluminescent compound according to the present invention can produce an organic electroluminescent device having high luminous efficiency and long operating lifetime.

  In addition, since the organic electroluminescent compound according to the present invention has a high efficiency in transporting electrons, crystallization in the case of producing an element can be prevented. Furthermore, the compound has good layer formability and improves the current characteristics of the device. Thus, they can produce organic electroluminescent devices with low drive voltage and high power efficiency.

  The present invention is described in detail below. However, the following details are intended to illustrate the present invention and are in no way intended to limit the scope of the invention.

  The present invention relates to a compound represented by the above formula 1, an organic electroluminescent material including the compound, and an organic electroluminescent element including the material.

  As used herein, “(C1-C30) alkyl (alkylene)” means a straight or branched alkyl (alkylene) having 1 to 30 carbon atoms, where the number of carbon atoms is Preferably it is 1-20, more preferably 1-10, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like.

  As used herein, “(C2-C30) alkenyl (alkenylene)” means a straight or branched alkenyl (alkenylene) having 2 to 30 carbon atoms, where the number of carbon atoms is Preferably 2-20, more preferably 2-10, including vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. It is not limited to.

  In the present specification, “(C 2 -C 30) alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably 2 to 20, more preferably Is 2-10 and includes, but is not limited to, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like.

  In the present specification, “(C1-C30) alkoxy” is a linear or branched alkoxy having 1 to 30 carbon atoms, wherein the number of carbon atoms is preferably 1 to 20, more preferably Is 1-10, including but not limited to methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy and the like.

  In the present specification, “(C3-C30) cycloalkyl” is a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, More preferably 3-7, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

  As used herein, “(C3-C30) cycloalkylene” is formed by removing hydrogen from a cycloalkyl having 3 to 30, preferably 3 to 20, more preferably 3 to 7 carbon atoms. Is.

  As used herein, “5- to 7-membered heterocycloalkyl” refers to B, N, O, S, P (═O), Si and P, preferably N, O and S, and 5 to 7 rings. Cycloalkyl having at least one heteroatom selected from skeletal atoms, including but not limited to tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like.

  As used herein, “halogen” includes F, Cl, Br and I.

  As used herein, “(C6-C30) aryl (arylene)” is a monocyclic or condensed ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, where the number of carbon atoms Is preferably 6-20, more preferably 6-12, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. Including, but not limited to. Naphthyl includes 1-naphthyl, 2-naphthyl and the like, anthracenyl includes 1-anthracenyl, 2-anthracenyl, 9-anthracenyl and the like, and phenanthrenyl includes 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl , 9-phenanthrenyl and the like, naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl and the like, pyrenyl includes 1-pyrenyl, 2-pyrenyl, 4-pyrenyl and the like, and biphenyl is 2-biphenyl. Terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4- Yl, m-terphenyl-3-yl, m-terphenyl 2-yl and the like, fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl and the like.

  In the present specification, “3 to 30-membered heteroaryl (heteroarylene)” is a group consisting of B, N, O, S, P (═O), Si and P, and 3 to 30 ring skeleton atoms. Aryl having at least one, preferably 1 to 4 heteroatoms selected; a single ring or a condensed ring fused with at least one benzene ring; preferably 5 to 21, more preferably 5 Having -12 ring skeleton atoms; may be partially saturated; formed by linking at least one heteroaryl or aryl group to a heteroaryl group through a single bond (s) It may be. Heteroaryl (arylene) includes a divalent aryl group that forms N-oxides, quaternary salts, and the like by oxidation or quaternization of heteroatoms present in the ring. Heteroaryl (arylene) includes furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like Cyclic heteroaryl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl , Benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, Fused ring heteroaryls including rubazolyl, phenanthridinyl, benzodioxolyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like, and N-oxides (eg, pyridyl N-oxide and quinolyl N -Oxides) and quaternary salts thereof. Pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, etc., pyridyl includes 2-pyridyl, 3-pyridyl, 4-pyridyl, etc., and indolyl includes 1-indolyl, 2-indolyl, 3-indolyl , 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl and the like. Furyl includes 2-furyl, 3-furyl and the like, and benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl and the like, Furanyl is 1-isobenzofurani , 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, etc., and quinolyl includes 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl and the like, and isoquinolyl includes 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl and the like Quinoxalinyl includes 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, and the like, and carbazolyl includes 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, and the like, and phenanthridine 1-phenanthridinyl, 2-phenanthridinyl, -Phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl and the like , Acridinyl includes 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl and the like; phenanthrolinyl includes 1,7-phenanthrolin-2-yl, 1,7-phenanthroline-3 -Yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9 -Yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline -3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline -9-yl, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline -5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-phenanthroline -2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6- Yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3- Yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9- Yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7- Enanthrolin-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7- Phenanthrolin-10-yl and the like, phenazinyl includes 1-phenazinyl, 2-phenazinyl and the like, and phenothiazinyl includes 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, Phenoxazinyl includes 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, etc., oxazolyl includes 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, etc., and oxadiazolyl Is 2 -Oxadiazolyl, 5-oxadiazolyl and the like, flazanyl includes 3-furanyl, etc., dibenzofuranyl includes 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl and the like. And dibenzothiophenyl includes 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, and the like.

  In the present specification, the term “substituted” in the term “substituted or unsubstituted” means that a hydrogen atom in a specific functional group is replaced with another atom or group, that is, a substituent.

Substituted alkyl (alkylene) group, substituted alkenyl group, substituted cycloalkyl (cycloalkylene) group, substituted heterocycloalkyl group, substituted aryl (arylene) in L ₁ , L ₂ , R _{1 to} R ₈ and R _{11 to} R ₁₇ groups Group, substituted heteroaryl (heteroarylene) group, substituted arylalkyl group and substituted aromatic ring substituent are each independently preferably substituted or unsubstituted with deuterium, halogen, halogen (C1-C30). ) Alkyl group, (C6-C30) aryl group, 3-30 membered heteroaryl group, (C1-C30) alkyl substituted 3-30 membered heteroaryl group, (C6-C30) aryl substituted 3 30-membered heteroaryl group, (C3-C30) cycloalkyl group, 5- to 7-membered heterocycloalkyl group, tri ( C1-C30) alkylsilyl group, tri (C6-C30) alkylsilyl group, di (C1-C30) alkyl (C6-C30) arylsilyl group, (C1-C30) alkyldi (C6-C30) arylsilyl group, C2-C30) alkenyl group, (C2-C30) alkynyl group, cyano group, N-carbazolyl group, di (C1-C30) alkylamino group, di (C6-C30) arylamino group, (C1-C30) alkyl ( C6-C30) arylamino group, di (C6-C30) arylboronyl group, di (C1-C30) alkylboronyl group, (C1-C30) alkyl (C6-C30) arylboronyl group, (C6-C30) ) Aryl (C1-C30) alkyl group, (C1-C30) alkyl (C6-C30) aryl group, carboxyl group, At least one selected from the group consisting of a tro group and a hydroxyl group, and more preferably a deuterium, halogen, (C1-C20) alkyl group substituted with or not substituted with a halogen and (C6-C20) It is at least one selected from the group consisting of aryl groups, and even more preferably at least one selected from the group consisting of deuterium, fluorine, methyl, phenyl and naphthyl.

In particular, in Formula 1 above, L ₁ and L ₂ each independently represent a single bond, a 3-30 membered heteroarylene group, a (C6-C30) arylene group, or a (C6-C30) cycloalkylene group; X ₁ is CH or N; Y ₁ and Y ₂ each independently represent —O—, —S—, —CR ₆ R ₇ — or —NR ₈ —; R _{1 to} R ₅ each independently and hydrogen, deuterium, halogen, (C1-C30) alkyl group, (C6-C30) aryl group, 3-30-membered heteroaryl group, N- carbazolyl _{group, -NR} 11 _{R 12} or -SiR ₁₃ R, ₁₄ R ₁₅ ; or R ₄ and R ₅ are each independently bonded to the adjacent substituent (s) via a (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene group, Ring or Forming a polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur; R _{6 to} R ₈ Each independently represents hydrogen, deuterium, halogen, a (C1-C30) alkyl group, a (C6-C30) aryl group, or a 3- to 30-membered heteroaryl group; R _{11 to} R ₁₅ are each independently Represents a (C1-C30) alkyl group, a (C6-C30) aryl group, or a 3- to 30-membered heteroaryl group; an arylene group, a heteroarylene group and a cycloalkylene group in L ₁ and L ₂ , and R ₁ alkyl group in to R ₈ and R ₁₁ to R _15, aryl and heteroaryl groups, deuterium, halogen, not been substituted or unsubstituted with halogen C1-C30) alkyl group, (C6-C30) aryl group, (C1-C30) alkyl (C6-C30) aryl group, 3-30 membered heteroaryl group, 3-30 substituted with (C6-C30) aryl It may be substituted with at least one selected from the group consisting of a membered heteroaryl group, a (C3-C30) cycloalkyl group and a (C6-C30) aryl (C1-C30) alkyl group.

In the above formula 1, L ₁ and L ₂ are each independently preferably a single bond, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, phenylene, methylphenylene, naphthylene, Biphenylene, terphenylene, anthracenylene, indenylene, fluorenylene, phenanthrenelene, triphenylenylene, pyrenylene, phenylylene, chrysenylene, naphthacenylene, fluoranthenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiazolylene, isothiazylene, isothylene Oxazolylene, Oxazolylene, Oxadiazolylene, Triazinylene, Tetrazinylene, Triazolylene, Frazanylene, Pyridylene, Pyra Nylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzimidazolylene, benzothiazolylene, benzisothiazolylene, benzoisoxazolylene, benzoxazolylene, isoindoleylene, indoleylene, indazolylene, Selected from the group consisting of benzothiadiazolylene, quinolylene, isoquinolylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxolylene, dibenzofuranylene and dibenzothiophenylene, and L ₁ and L ₂ are heavy Hydrogen, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl group, (C6-C30) aryl group, (C1-C30) alkyl (C6-C 0) aryl group, 3-30 membered heteroaryl group, (C6-C30) aryl substituted 3-30 membered heteroaryl group, (C3-C30) cycloalkyl group and (C6-C30) aryl (C1-C30) ) It may be substituted with at least one selected from the group consisting of alkyl. In Formula 1 above, L ₁ and L ₂ are each independently selected from the group consisting of a single bond, phenylene, methylphenylene and cyclohexylene.

から選択される。 In Formula 1 above, Y ₁ and Y ₂ are each independently the following structure:

Selected from.

In the above formula 1, R _{1 to} R ₅ are each independently preferably (C 6 -C 20) aryl group, 5 to 21 membered heteroaryl group, —NR ₁₁ R ₁₂ or —SiR ₁₃ R ₁₄ R ₁₅ . Yes; or substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene group attached to adjacent substituent (s) to form a monocyclic or polycyclic, alicyclic ring Form a ring of formula or aromatic, more preferably phenyl, carbazolyl, diphenylamino or methyldiphenylsilyl; or via a substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene group Bond to adjacent substituent (s) to form a monocyclic or polycyclic, alicyclic or aromatic ring. R _{11 to} R ₁₅ are each independently preferably a (C 1 -C 6) alkyl group or a (C 6 -C 20) aryl group, more preferably methyl or phenyl.

In the above formula 1, R _{6 to} R ₈ are preferably each independently hydrogen, (C1-C6) alkyl group, substituted or unsubstituted (C6-C20) aryl group, or substituted or unsubstituted 5-21. A member heteroaryl group, more preferably hydrogen; methyl; phenyl; biphenyl; naphthyl; phenyl substituted with deuterium; phenyl substituted with fluorine; fluorenyl substituted with methyl; or naphthylphenyl.

は、以下の構造：

から選択されるが、それらに限定されない。 In Equation 1 above,

Has the following structure:

But is not limited to these.

Representative organic electroluminescent compounds of the present invention include, but are not limited to, the following compounds:

（式中、Ｌ_１、Ｌ_２、Ｘ_１、Ｙ_１、Ｙ_２、Ｒ_１〜Ｒ_５、ａ、ｂ、ｃ、ｄおよびｅは、上記の式１に定義されている通りであり、Ｈａｌはハロゲンを表す。） The organic electroluminescent compound according to the present invention can be prepared according to the following reaction scheme.
[Reaction Scheme 1]

(In the formula, L ₁ , L ₂ , X ₁ , Y ₁ , Y ₂ , R _{1 to} R ₅ , a, b, c, d and e are as defined in Formula 1 above, and Hal Represents halogen.)

  In addition, the present invention provides an organic electroluminescent material comprising the compound of Formula 1 and an organic electroluminescent device comprising the material. The above materials may be composed solely of the organic electroluminescent compounds according to the present invention, or may further comprise conventional materials generally used for organic electroluminescent materials. The organic electroluminescence element includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. Said organic layer comprises at least one organic electroluminescent compound of formula 1 according to the invention. Further, the organic layer includes a light emitting layer, and the organic electroluminescent compound of Formula 1 is included as a host material in the light emitting layer.

（式中、Ｍ^１はＩｒ、Ｐｔ、ＰｄおよびＯｓからなる群から選択され；Ｌ^１０１、Ｌ^１０２およびＬ^１０３は各々独立して以下の構造：

から選択され、
Ｒ_２０１〜Ｒ_２０３は各々独立して、水素、重水素、ハロゲン（複数も含む）で置換されたもしくは置換されていない（Ｃ１−Ｃ３０）アルキル基、（Ｃ１−Ｃ３０）アルキル基（複数も含む）で置換されたもしくは置換されていない（Ｃ６−Ｃ３０）アリール基、またはハロゲンを表し、
Ｒ_２０４〜Ｒ_２１９は各々独立して、水素、重水素、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル基、置換もしくは非置換（Ｃ１−Ｃ３０）アルコキシ基、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル基、置換もしくは非置換（Ｃ２−Ｃ３０）アルケニル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基、置換もしくは非置換モノ−もしくはジ−（Ｃ１−Ｃ３０）アルキルアミノ基、置換もしくは非置換モノ−もしくはジ−（Ｃ６−Ｃ３０）アリールアミノ基、ＳＦ_５、置換もしくは非置換トリ（Ｃ１−Ｃ３０）アルキルシリル基、置換もしくは非置換ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル基、置換もしくは非置換トリ（Ｃ６−Ｃ３０）アリールシリル基、シアノ基またはハロゲンを表し、
Ｒ_２２０〜Ｒ_２２３は各々独立して、水素、重水素、ハロゲン（複数も含む）で置換されたもしくは置換されていない（Ｃ１−Ｃ３０）アルキル基、または（Ｃ１−Ｃ３０）アルキル基（複数も含む）で置換されたもしくは置換されていない（Ｃ６−Ｃ３０）アリール基を表し、
Ｒ_２２４およびＲ_２２５は各々独立して、水素、重水素、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基、またはハロゲンを表し、あるいはＲ_２２４およびＲ_２２５は、（Ｃ３−Ｃ１２）アルキレン基または（Ｃ３−Ｃ１２）アルケニレン基を介して互いに結合して、単環または多環、脂環式環または芳香環を形成し、
Ｒ_２２６は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基、置換もしくは非置換３〜３０員ヘテロアリール基またはハロゲンを表し、
Ｒ_２２７〜Ｒ_２２９は各々独立して、水素、重水素、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル基、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基またはハロゲンを表し、
Ｑは、

を表し、Ｒ_２３１〜Ｒ_２４２は各々独立して、水素、重水素、ハロゲン（複数も含む）で置換されたもしくは置換されていない（Ｃ１−Ｃ３０）アルキル基、（Ｃ１−Ｃ３０）アルコキシ基、ハロゲン、置換もしくは非置換（Ｃ６−Ｃ３０）アリール基、シアノ基、または置換もしくは非置換（Ｃ５−Ｃ３０）シクロアルキル基を表し、あるいはＲ_２３１〜Ｒ_２４２の各々は、（Ｃ２−Ｃ３０）アルキレン基または（Ｃ２−Ｃ３０）アルケニレン基を介して隣接する置換基に結合してスピロ環もしくは縮合環を形成でき、または（Ｃ２−Ｃ３０）アルキレン基もしくは（Ｃ２−Ｃ３０）アルケニレン基を介してＲ_２０７〜Ｒ_２０８に結合して飽和もしくは非飽和縮合環を形成できる）
によって表される化合物から選択され得る。 In addition, the phosphorescent dopant used for the organic electroluminescent device together with the host material according to the present invention is represented by the following formula 2:

Wherein M ¹ is selected from the group consisting of Ir, Pt, Pd and Os; L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are each independently the following structures:

Selected from
R _{201 to} R ₂₀₃ each independently represent a hydrogen (C 1 -C 30) alkyl group or a (C 1 -C 30) alkyl group (including a plurality) substituted or unsubstituted with hydrogen, deuterium, or halogen (s). ) Substituted or unsubstituted (C6-C30) aryl group, or halogen,
R ₂₀₄ to R ₂₁₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C3-C30) cycloalkyl Alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted mono- or di- (C1-C30) alkylamino group, substituted or unsubstituted mono - or di - (C6-C30) arylamino group, SF _5, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) aryl silyl group, Represents a substituted or unsubstituted tri (C6-C30) arylsilyl group, cyano group or halogen;
R _{220 to} R ₂₂₃ each independently represents a (C1-C30) alkyl group substituted with or not substituted with hydrogen, deuterium, halogen (s), or a (C1-C30) alkyl group (s). Represents a substituted or unsubstituted (C6-C30) aryl group,
R ₂₂₄ and R ₂₂₅ each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a halogen, or _R224 and R225 ₂₂₅ are bonded to each other via a (C3-C12) alkylene group or a (C3-C12) alkenylene group to form a monocyclic or polycyclic, alicyclic or aromatic ring;
R ₂₂₆ represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted 3 to 30 membered heteroaryl group, or halogen;
R _{227 to} R ₂₂₉ each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a halogen;
Q is

Each of R _{231 to} R ₂₄₂ is independently a (C1-C30) alkyl group substituted with or not substituted with hydrogen, deuterium, halogen (s), or a (C1-C30) alkoxy group, halogen, unsubstituted or substituted (C6-C30) aryl group, a cyano group or a substituted or represents unsubstituted (C5-C30) cycloalkyl group, or each of _R 231 _{to R 242} is, (C2-C30) alkylene group, Or a (C2-C30) alkenylene group can be bonded to an adjacent substituent to form a spiro ring or a condensed ring, or a (C2-C30) alkylene group or a (C2-C30) alkenylene group can be used as R ₂₀₇ to Can be bonded to R ₂₀₈ to form a saturated or unsaturated condensed ring)
May be selected from the compounds represented by

を含むが、それらに限定されない。 The dopant of formula 2 is:

Including, but not limited to.

  The organic electroluminescence device according to the present invention may further include at least one compound selected from the group consisting of arylamine compounds and styrylaryl compounds in addition to the organic electroluminescence compound represented by Formula 1. Good.

  In the organic electroluminescence device according to the present invention, the organic layer further includes a Group 1 metal, a Group 2 metal, a transition metal of the fourth period, a transition metal of the fifth period, a lanthanide, and an organic metal of a d-transition element of the periodic table, Alternatively, at least one metal selected from the group consisting of at least one complex compound containing the metal may be included. The organic layer may include a light emitting layer and a charge generation layer.

  Furthermore, the organic electroluminescent element emits white light by further including at least one light emitting layer containing a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound in addition to the organic electroluminescent compound according to the present invention. it can.

Preferably, in the organic electroluminescence device according to the present invention, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as “surface layer”) is one or both. May be disposed on the inner surface (including the plurality) of the electrode (including the plurality). In particular, a silicon or aluminum chalcogenide (including oxide) layer is disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is disposed on the cathode surface of the electroluminescent medium layer. Is preferred. Such a surface layer provides operational stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiO _X (1 ≦ X ≦ 2), AlO _X (1 ≦ X ≦ 1.5), SiON, SiAlON, etc., and the metal halide includes LiF, MgF ₂ , CaF ₂ , The rare earth metal fluoride is included, and the metal oxide includes Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

  Preferably, in the organic electroluminescence device according to the present invention, the mixed region of the electron transport compound and the reducing dopant or the mixed region of the hole transport compound and the oxidizing dopant may be disposed on at least one surface of the pair of electrodes. In this case, since the electron transport compound is reduced to an anion, it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. Furthermore, since the hole transport compound is oxidized to cations, it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer has two or more electroluminescent layers, and may be used as a charge generation layer to produce an electroluminescent device that emits white light.

  Hereinafter, the organic electroluminescent compound, the method for preparing the compound, and the light emission characteristics of the device containing the compound of the present invention will be described in detail with reference to the following examples.

化合物１−１の調製
トルエン（１Ｌ）および精製水（２００ｍＬ）の混合物中に２，４−ジクロロキナゾリン（５０ｇ、２５１ｍｍｏｌ）およびジベンゾ［ｂ，ｄ］フラン−４−イルボロン酸（５３．２ｇ、２５１ｍｍｏｌ）を溶解した後、Ｐｄ（ＰＰｈ_３）_４（１４．５ｇ、１２．５ｍｍｏｌ）およびＮａ_２ＣＯ_３（８０ｇ、７５５ｍｍｏｌ）をその混合物に加えた。その混合物を８０℃にて２０時間撹拌した。反応混合物を室温に冷却し、反応を塩化アンモニウム水溶液（２００ｍＬ）で停止させた。反応混合物を酢酸エチル（ＥＡ）（１Ｌ）で抽出し、水層をジクロロメタン（１Ｌ）でさらに抽出した。得られた有機層を無水硫酸マグネシウムで乾燥させ、減圧下で有機溶媒を除去した。得られた固体をシリカゲルで濾過し、減圧下で溶媒を除去した。得られた固体をＥＡ（１００ｍＬ）で洗浄して化合物１−１（５０ｇ、７４％）を得た。 Example 1: Preparation of compound C-18

Preparation of Compound 1-1 2,4-Dichloroquinazoline (50 g, 251 mmol) and dibenzo [b, d] furan-4-ylboronic acid (53.2 g, 251 mmol) in a mixture of toluene (1 L) and purified water (200 mL). ) Was dissolved, and Pd (PPh ₃ ) ₄ (14.5 g, 12.5 mmol) and Na ₂ CO ₃ (80 g, 755 mmol) were added to the mixture. The mixture was stirred at 80 ° C. for 20 hours. The reaction mixture was cooled to room temperature and the reaction was quenched with aqueous ammonium chloride (200 mL). The reaction mixture was extracted with ethyl acetate (EA) (1 L) and the aqueous layer was further extracted with dichloromethane (1 L). The obtained organic layer was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. The resulting solid was filtered through silica gel and the solvent was removed under reduced pressure. The obtained solid was washed with EA (100 mL) to obtain compound 1-1 (50 g, 74%).

Preparation of compound 1-2 9-phenyl-9H-carbazol-3-ylboronic acid (30 g, 149 mmol), 1-bromo-2-nitrobenzene in a mixture of toluene (600 mL), EtOH (150 mL) and purified water (150 mL) After dissolving (51 g, 178.8 mmol), K ₂ CO ₃ (52 g, 372.5 mmol) and Pd (PPh ₃ ) ₄ (6.8 g, 5.8 mmol), the reaction mixture was stirred at reflux for 24 hours. did. After the reaction stopped, the reaction mixture was cooled to room temperature and the aqueous layer was removed from the mixture by gravity separation. The resulting organic layer was concentrated, triturated with methylene chloride (MC) and then filtered to give compound 1-2 (50 g, 92%).

Preparation of Compound 1-3 After dissolving Compound 1-2 (50 g, 137 mmol) in a mixture of P (OEt) ₃ (300 mL) and 1,2-dichlorobenzene (300 mL), the reaction mixture was stirred at 150 ° C. for 24 hours. Stir for hours. After stopping the reaction, the reaction mixture was concentrated under reduced pressure and extracted with EA. The organic layer was then concentrated and purified through a silica column to give compound 1-3 (32 g, 70%).

Preparation of Compound C-18 Compound 1-1 (5.5 g, 16.5 mmol) and Compound 1-3 (5.0 g, 15 mmol) were suspended in 80 mL of dimethylformamide (DMF) and then 60% NaH (930 mg). 23.2 mmol) was added to the mixture at room temperature. The reaction mixture was stirred for 12 hours. After adding purified water (1 L), the mixture was filtered under reduced pressure. The resulting solid was triturated with MeOH / EA, triturated with DMF, and triturated with EA / tetrahydrofuran (THF). It was dissolved in MC and filtered through silica. It was then triturated with MeOH / EA to give compound C-18 (4.6 g, 48.9%).
MS / FAB measured value 627; calculated value 626.70

Element Example 1: Production of an organic light emitting diode (OLED) element using the organic electroluminescent compound according to the present invention An OLED element was produced using the compound according to the present invention. Transparent electrode indium tin oxide (ITO) thin film (15Ω / sq) on glass substrate for OLED device (Samsung Corning, Public of Korea) was ultrasonically cleaned continuously with trichlorethylene, acetone, ethanol and distilled water And then stored in isopropanol. Next, the ITO substrate was attached to the substrate holder of the vacuum evaporation apparatus. ^{N 1, N 1 '- (} [1,1'- biphenyl] -4,4'-diyl) bis ^{(N 1} - ^{(naphthalen-1-yl)} -N ^{4, N} 4 - diphenyl-1,4 Diamine) was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to 10 ⁻⁶ torr. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Next, N, N′-di (4-biphenyl) -N, N′-di (4-biphenyl) -4,4′-diaminobiphenyl is introduced into another cell of the vacuum deposition apparatus, and current is supplied to the cell. Evaporation was performed by applying, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-18 was introduced as a host material into one cell of a vacuum vapor deposition apparatus, and compound D-7 was introduced as a dopant into another cell. The two materials were evaporated at different rates and deposited with a doping amount of 4 wt% dopant relative to the total amount of host material and dopant to form a light emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole was introduced into one cell and lithium The quinolate was introduced into another cell. The two materials were evaporated at the same rate, and each material was deposited with a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light emitting layer. Next, after depositing lithium quinolate as an electron injection layer having a thickness of 1 to 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm is deposited by another vacuum deposition device on the electron injection layer. It was. Thus, the OLED element was manufactured.

The manufactured OLED element showed red light emission with a luminance of 3,400 cd / m ² and a current density of 44.7 mA / cm ² at a driving voltage of 5.6V.

Comparative Example 1: Production of OLED Device Using Conventional Electroluminescent Material Light-Emitting Layer by Using 4,4′-N, N′-Dicarbazole-biphenyl (CBP) as a Host Material and Compound D-11 as a Dopant And a hole blocking layer having a thickness of 10 nm by using aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate as a light emitting layer. An OLED element was manufactured in the same manner as in the element example 1, except that vapor deposition was performed between the electron transport layer and the electron transport layer.

The manufactured OLED element showed red emission having a luminance of 1,000 cd / m ² and a current density of 20.0 mA / cm ² at a driving voltage of 8.2V.

Claims (6)

Organic electroluminescent compounds represented by the following formula 1:

(Where
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted 3 to 30 membered heteroarylene group, substituted or unsubstituted (C6-C30) arylene group, or substituted or unsubstituted (C3-C30) cycloalkylene Represents a group,
X ₁ represents CH or N;
Y ₁ and Y ₂ each independently represent —O—, —S—, —CR ₆ R ₇ — or —NR ₈ —,
R _{1 to} R ₅ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted 3 to 30 members. A heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl group, -NR ₁₁ R ₁₂ , —SiR ₁₃ R ₁₄ R ₁₅ , —SR ₁₆ , —OR ₁₇ , a cyano group, a nitro group, or a hydroxyl group, or R ₄ and R ₅ are each independently substituted or unsubstituted ( C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene group linked to adjacent substituent (s) Combined to form a monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur. Often,
R _{6 to} R ₈ and R _{11 to} R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or Represents an unsubstituted 3-30 membered heteroaryl group, a substituted or unsubstituted 5-7 membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group, or substituted or unsubstituted (C3-C30) Bonded to an adjacent substituent (s) via an alkylene or substituted or unsubstituted (C3-C30) alkenylene group to form a monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom ( May also be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur,
a, b, c and e each independently represents an integer of 1 to 4, and when a, b, c or e is an integer of 2 or more, each of R ₁ , each of R ₂ and each of R ₃ Or each of R ₅ is the same or different,
d represents an integer of 1 to 3, and when d is an integer of 2 or more, each R ₄ is the same or different;
Heterocycloalkyl and heteroaryl (heteroarylene) groups contain at least one heteroatom selected from B, N, O, S, P (═O), Si and P). The substituted alkyl (alkylene) group, substituted alkenylene group, substituted cycloalkyl (alkylene) group, substituted heterocycloalkyl group, substituted aryl (arylene) in the L ₁ and L ₂ , R _{1 to} R ₈ and R _{11 to} R ₁₇ groups A group, a substituted heteroaryl (arylene) group, a substituted arylalkyl group and a substituted aromatic ring substituent each independently a deuterium, halogen, halogen substituted or unsubstituted (C1-C30) alkyl group, (C6-C30) aryl group, 3-30 membered heteroaryl group, (C1-C30) 3-30 membered heteroaryl group substituted with alkyl, (C6-C30) 3-30 membered heteroaryl substituted with aryl Group, (C3-C30) cycloalkyl group, 5- to 7-membered heterocycloalkyl group, tri (C1-C30) Alkylsilyl group, tri (C6-C30) arylsilyl group, di (C1-C30) alkyl (C6-C30) arylsilyl group, (C1-C30) alkyldi (C6-C30) arylsilyl group, (C2-C30) Alkenyl group, (C2-C30) alkynyl group, cyano group, N-carbazolyl group, di (C1-C30) alkylamino group, di (C6-C30) arylamino group, (C1-C30) alkyl (C6-C30) Arylamino group, di (C6-C30) arylboronyl group, di (C1-C30) alkylboronyl group, (C1-C30) alkyl (C6-C30) arylboronyl group, (C6-C30) aryl (C1 -C30) alkyl group, (C1-C30) alkyl (C6-C30) aryl group, carboxyl group, nitro group and Is at least one selected from the group consisting of hydroxyl group, organic electroluminescent compound according to claim 1. L ₁ and L ₂ each independently represents a single bond, a 3- to 30-membered heteroarylene group, a (C6-C30) arylene group, or a (C6-C30) cycloalkylene group,
X ₁ is CH or N;
Y ₁ and Y ₂ each independently represent —O—, —S—, —CR ₆ R ₇ — or —NR ₈ —,
R _{1 to} R ₅ are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl group, (C 6 -C 30) aryl group, 3 to 30 membered heteroaryl group, N-carbazolyl group, —NR ₁₁ R ₁₂ , or —SiR ₁₃ R ₁₄ R ₁₅ , or R ₄ and R ₅ each independently represents an adjacent substituent (s) via (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene groups. The carbon atom (s) is substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur, to form a monocyclic or polycyclic, alicyclic or aromatic ring. You can,
R _{6 to} R ₈ each independently represent hydrogen, deuterium, halogen, a (C1-C30) alkyl group, a (C6-C30) aryl group, or a 3-30 membered heteroaryl group;
R _{11 to} R ₁₅ each independently represents a (C1-C30) alkyl group, a (C6-C30) aryl group, or a 3-30 membered heteroaryl group,
The arylene group, heteroarylene group and cycloalkylene group in L ₁ and L ₂ , and the alkyl group, aryl group, and heteroaryl group in R _{1 to} R ₈ and R _{11 to} R ₁₅ are substituted with deuterium, halogen, and halogen. Or (C1-C30) alkyl group, (C6-C30) aryl group, (C1-C30) alkyl (C6-C30) aryl group, 3-30 membered heteroaryl group, (C6-C30) aryl And may be substituted with at least one selected from the group consisting of a 3- to 30-membered heteroaryl group, a (C3-C30) cycloalkyl group, and a (C6-C30) aryl (C1-C30) alkyl group substituted with The organic electroluminescent compound according to claim 1. Part in Equation 1:

Has the following structure:

The organic electroluminescent compound according to claim 1, which is selected from: The compound represented by Formula 1 is

The organic electroluminescent compound according to claim 1, which is selected from the group consisting of:   The organic electroluminescent element containing the organic electroluminescent compound of Claim 1.