KR20220077067A - Organic electroluminescent compound, a plurality of host materials comprising the same, and organic electroluminescent device - Google Patents

Abstract

The present application relates to an organic electroluminescent compound, a plurality of host materials including the same, and an organic electroluminescent device. By including the organic electroluminescent compound according to the present disclosure and/or a plurality of host materials including the same, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan characteristics can be manufactured.

Description

An organic electroluminescent compound, a plurality of host materials comprising the same, and an organic electroluminescent device

The present application relates to an organic electroluminescent compound, a plurality of host materials including the same, and an organic electroluminescent device.

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

The light emitting material of an organic electroluminescent device is the most important factor determining the light emitting efficiency of the device, and can be divided into a host material and a dopant material from a functional point of view. It can be used by mixing In general, a device having excellent EL characteristics has a structure including a light emitting layer made by doping a dopant into a host. , the choice is important.

Recently, the development of high-efficiency and long-lived organic electroluminescent devices has emerged as an urgent task. In particular, considering the level of electroluminescence characteristics required for mid- to large-sized OLED panels, the development of materials that are very superior compared to conventional light emitting materials is difficult. It is urgent.

Japanese Patent Application Publication JP 5185591 B2 discloses a specific dopant compound and a host compound having a polycyclic condensed aromatic skeleton such as benzochrysene, but the organic electroluminescent compound claimed in the present application and a host material of a specific combination including the same are specifically disclosed. It has not been disclosed, and there is a continuous need to develop a light emitting material having improved performance, such as improved driving voltage, luminous efficiency, and long lifespan, compared to the combination of a specific compound previously disclosed.

Japanese Patent Publication JP 5185591 B2 (Registered on January 1, 2013)

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent compound capable of manufacturing an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan characteristics, and a plurality of types of host materials including the same and, secondly, to provide an organic electroluminescent device including the organic electroluminescent compound and/or a plurality of host materials.

As a result of intensive research to solve the above technical problem, the present inventors found that a compound having a benzo [c] chrysenyl moiety has an energy level suitable for use in OLEDs, and particularly binds to an aminoaryl or azine-based heteroaryl moiety As a result, it was discovered that excellent device characteristics were exhibited, and the present invention was completed. The organic electroluminescent compound according to the present invention exhibiting these characteristics is represented by the following formula (1).

[Formula 1]

In Formula 1,

R ₁ to R ₁₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, A fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -(L ₁ ) _n -(HAr) _m , or -L ₃ -N-(Ar ₃ ) (Ar ₄ ); adjacent substituents may be linked to each other to form a ring;

provided that at least one of R ₁ to R ₁₄ is -(L ₁ ) _n -(HAr) _m or -L ₃ -N-(Ar ₃ )(Ar ₄ );

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

HAr is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

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

Ar ₃ and Ar ₄ are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

n and m are each independently an integer of 1 or 2;

when n and m are integers of 2, each of L ₁ and HAr may be the same as or different from each other;

However, the following compounds are excluded from the organic electroluminescent compound represented by Formula 1 above.

By including the organic electroluminescent compound according to the present invention, it is possible to manufacture an organic electroluminescent device having a low driving voltage and/or high luminous efficiency and/or long lifespan characteristics.

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

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

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

The present application relates to a plurality of host materials including a first host material including the organic electroluminescent compound represented by Formula 1 and a second host material different from the first host material, and an organic electroluminescent device including the same.

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

As used herein, “organic electroluminescent material” means a material that can be used in an organic electroluminescent device, and may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may include a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, It may be an electron transporting material, an electron injecting material, or the like.

As used herein, "a plurality of types of host materials" means an organic electroluminescent material in which two or more types of host materials are combined, and before (eg, before deposition) and after being included in an organic electroluminescent device (eg, for example) , after deposition) may mean all of the materials. The plurality of types of host materials of the present application may be included in any light emitting layer constituting the organic electroluminescent device, and two or more kinds of compounds included in the plurality of types of host materials may be included in one light emitting layer, respectively, in different light emitting layers. may be included. When two or more types of host materials are included in one layer, for example, the layer may be mixed and vapor-deposited, or the layer may be separately and simultaneously co-deposited to form the layer.

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

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

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

In addition, in the description of "substituted or unsubstituted" herein, "substitution" means that a hydrogen atom in a functional group is replaced with another atom or another functional group (ie, a substituent), and two or more substituents among the substituents are substituted with a connected group. do. For example, "a substituent to which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl or may be interpreted as a substituent in which two heteroaryls are connected. In the formula herein, substituted (C1-C30)alkyl, substituted (C2-C30)alkenyl, substituted (C6-C30)aryl(ene), substituted (3-30 membered)heteroaryl(ren), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring group, substituted tri (C1-C30) Substituents of alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, and substituted tri(C6-C30)arylsilyl 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 membered) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl unsubstituted or substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with one or more of (C1-C30)alkyl and (3-30 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- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino substituted or unsubstituted with (C1-C30)alkyl; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30)arylphosphinyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl (C6-C30)aryl, preferably at least one selected from the group consisting of, for example, deuterium; methyl; tert -butyl; cyclohexyl; phenyl unsubstituted or substituted with one or more of methyl and tert -butyl; naphthyl; m-biphenyl; p-biphenyl; anthracenyl; fluoranthenyl; fluorenyl unsubstituted or substituted with (C1-C10)alkyl or (C6-C18)aryl; 9,10-dihydrophenanthrenyl unsubstituted or substituted with (C1-C10)alkyl; pyridyl unsubstituted or substituted with phenyl; phenoxazinyl; diphenylamino; phenyl-substituted benzimidazolyl; dibenzothiophenyl; And it may be at least one selected from dibenzofuranyl.

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

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

[Formula 1]

In Formula 1,

R ₁ to R ₁₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, A fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -(L ₁ ) _n -(HAr) _m , or -L ₃ -N-(Ar ₃ ) (Ar ₄ ); adjacent substituents may be linked to each other to form a ring;

provided that at least one of R ₁ to R ₁₄ is -(L ₁ ) _n -(HAr) _m or -L ₃ -N-(Ar ₃ )(Ar ₄ );

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

HAr is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

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

Ar ₃ and Ar ₄ are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

n and m are each independently an integer of 1 or 2;

when n and m are integers of 2, each of L ₁ and HAr may be the same as or different from each other;

However, the following compounds are excluded from the organic electroluminescent compound represented by Formula 1 above.

For example, R ₁ to R ₁₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 membered) heteroaryl, -(L ₁ ) _n - (HAr) _m , or -L ₃ -N-(Ar ₃ )(Ar ₄ ), preferably hydrogen, deuterium, substituted or unsubstituted with substituted or unsubstituted (5-30 membered) heteroaryl (C6-C25)aryl, substituted or unsubstituted (5-25 membered)heteroaryl, -(L ₁ ) _n -(HAr) _m , or -L ₃ -N-(Ar ₃ )(Ar ₄ ) can be and more preferably hydrogen, deuterium, substituted or unsubstituted (5-25 membered) heteroaryl or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-18 membered) heteroaryl, -(L ₁ ) _n -(HAr) _m , or -L ₃ -N-(Ar ₃ )(Ar ₄ ).

At least one of R ₁ to R ₁₄ according to an embodiment is -(L ₁ ) _n -(HAr) _m or -L ₃ -N-(Ar ₃ )(Ar ₄ ).

For example, at least one of R ₁ to R ₁₄ may be -(L ₁ ) _n -(HAr) _m .

For example, L ₁ may be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5-30 membered)heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or It may be an unsubstituted (5-18 membered) heteroarylene. For example, L ₁ may be a single bond or may be a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted pyridylene.

For example, HAr may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30 membered)heteroaryl, preferably a substituted or unsubstituted (5-25 membered)heteroaryl may be, and more preferably a substituted or unsubstituted (5-18 membered) heteroaryl containing at least one nitrogen. For example, HAr can be substituted or unsubstituted carbazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted quinazolinyl. The substituents of the substituted carbazolyl, substituted triazinyl, substituted quinoxalinyl, and substituted quinazolinyl include a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fusion ring; substituted or unsubstituted (C6-C30)aryl; and substituted or unsubstituted (5-30 membered) heteroaryl, preferably a fused ring group of a substituted or unsubstituted (C5-C25) aliphatic ring and (C6-C25) aromatic ring ; substituted or unsubstituted (C6-C25)aryl; And it may be one or more selected from substituted or unsubstituted (5-25 membered) heteroaryl, for example, the substituent is phenyl; naphthyl; m-biphenyl; p-biphenyl; fluorenyl unsubstituted or substituted with (C1-C10)alkyl; 9,10-dihydrophenanthrenyl unsubstituted or substituted with (C1-C10)alkyl; pyridyl; dibenzothiophenyl; And it may be at least one selected from dibenzofuranyl.

For example, at least one of R ₁ to R ₁₄ may be -L ₃ -N-(Ar ₃ )(Ar ₄ ).

For example, L ₃ may be a single bond.

For example, Ar ₃ and Ar ₄ may each independently be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18) aryl or substituted or unsubstituted (5-18 membered) ) may be heteroaryl. For example, Ar ₃ and Ar ₄ are each independently, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

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

The compound of Formula 1 according to the present application may be prepared by a known synthesis method, and in particular, a synthesis method disclosed in a number of patent documents may be used.

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

The organic electroluminescent material may consist of the organic electroluminescent compound of the present application alone, or may further include conventional materials included in the organic electroluminescent material. When two or more types of materials are included in one layer, they may be mixed and deposited to form a layer, or may be separately and simultaneously co-deposited to form a layer. The organic electroluminescent material according to an example may include at least one compound represented by Formula 1 above. For example, the compound of Formula 1 may be included in the emission layer, and when included in the emission layer, the compound of Formula 1 may be included as a host, and more specifically, may be included as a phosphorescent host.

According to one embodiment, the present application provides a plurality of host materials including a first host material represented by Formula 1 and a second host material different therefrom.

The second host material according to an example includes an organic electroluminescent compound represented by Formula 2 below.

[Formula 2]

In Formula 2,

X ₁ and Y ₁ are each independently -N=, -NR ₆₇ -, -O-, or -S-, with the proviso that any one of X ₁ and Y ₁ is -N=, and among X ₁ and Y ₁ the other is -NR ₆₇ -, -O- or -S-;

R ₆₁ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

R ₆₂ to R ₆₄ and R ₆₇ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30) Arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L ₃ "-N(Ar ₃ ")(Ar ₄ "); Substituents may be linked to each other to form a ring;

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

Ar ₃ ” and Ar ₄ ” are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C3-C30) a fused ring group of an aliphatic ring and an aromatic ring of (C6-C30), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

L ₄ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

R ₆₅ and R ₆₆ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

a is 1, b and c are each independently 1 or 2, d is an integer from 1 to 4, and when b to d are an integer of 2 or more, each of R ₆₂ to R ₆₄ may be the same or different from each other. have.

For example, any one of X ₁ and Y ₁ may be -N=, and the other may be -O- or -S-. For example, X ₁ may be -N= and Y ₁ may be -O-, X ₁ may be -O- and Y ₁ may be -N=, or X ₁ may be -S- and Y ₁ may be -N=

For example, R ₆₁ may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30 membered)heteroaryl, preferably a substituted or unsubstituted (C6-C25)aryl or It may be a substituted or unsubstituted (5-25 membered)heteroaryl, more preferably a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5-18 membered)heteroaryl. For example, R ₆₁ may be unsubstituted phenyl, unsubstituted naphthyl, unsubstituted o-biphenyl, unsubstituted m-biphenyl, unsubstituted p-biphenyl, or unsubstituted pyridyl .

For example, R ₆₂ to R ₆₄ and R ₆₇ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C6-C30)arylyl and preferably hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted (C6-C25)aryl, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C18) may be aryl. For example, R ₆₂ to R ₆₄ may each independently be hydrogen or unsubstituted phenyl.

For example, L ₄ may be a single bond or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond or a substituted or unsubstituted (C6-C25)arylene, more preferably a substituted or an unsubstituted (C6-C18)arylene. For example, L ₄ may be a single bond or may be unsubstituted phenylene or unsubstituted naphthylene.

For example, R ₆₅ and R ₆₆ may each independently represent a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-20 membered) ) may be heteroaryl. For example, R ₆₅ and R ₆₆ are each independently, substituted or unsubstituted phenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl , substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted di Benzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted C22 aryl, substituted or unsubstituted carbazolyl , a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzofuropyridyl. The substituent of the substituted substituent is deuterium; methyl; tert -butyl; cyclohexyl; phenyl unsubstituted or substituted with one or more of methyl and tert -butyl; naphthyl; biphenyl; anthracenyl; fluoranthenyl; phenylfluorenyl; pyridyl unsubstituted or substituted with phenyl; phenoxazinyl; diphenylamino; and phenyl-substituted benzimidazolyl.

According to an example, the organic electroluminescent compound of Formula 2 may be more specifically exemplified as the following compound, but is not limited thereto.

The compound represented by Formula 2 according to an example may be prepared with reference to a synthesis method known to those skilled in the art.

The second host material according to another embodiment includes an organic electroluminescent compound represented by the following Chemical Formula 3.

[Formula 3]

In Formula 3,

Y is -O- or -S-;

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

HAr' is a substituted or unsubstituted (3-30 membered) heteroaryl containing one or more nitrogen atoms;

R′ ₁ and R′ ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)aryl Silyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl (C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl ( C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino is; may be linked to adjacent substituents to form a ring;

e is an integer from 1 to 4, f is an integer from 1 to 3;

When e and f are each an integer of 2 or more, each R′ ₁ and each R′ ₂ may be the same as or different from each other.

For example, L′ ₁ may be a single bond or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond or a substituted or unsubstituted (C6-C25)arylene, more preferably It may be a single bond or a substituted or unsubstituted (C6-C18)arylene. For example, L′ ₁ may be a single bond, phenylene substituted or unsubstituted with naphthyl, naphthylene unsubstituted or substituted with phenyl, or unsubstituted biphenylene.

For example, HAr' may be a substituted or unsubstituted (5-30 membered)heteroaryl containing one or more nitrogen atoms, preferably (C6-C30)aryl containing at least two nitrogen atoms and/or or (5-30 membered)heteroaryl unsubstituted or substituted with (5-30 membered)heteroaryl, more preferably (C6-C25)aryl and/or ( It may be a (5-18 membered) heteroaryl substituted or unsubstituted with 5-25 membered) heteroaryl. For example, HAr' is substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridopyra zinyl, substituted or unsubstituted benzoquinazolinyl, or substituted or unsubstituted benzoquinoxalinyl. In this case, the substituent of the above substituent may be at least one of a substituted or unsubstituted (C6-C30)aryl and a substituted or unsubstituted (5-30 membered)heteroaryl, preferably a substituted or unsubstituted (C6 It may be at least one of -C25)aryl and substituted or unsubstituted (5-25 membered)heteroaryl, more preferably substituted or unsubstituted (C6-C18)aryl and substituted or unsubstituted (5-18 membered) One) may be at least one of heteroaryl. For example, the substituent of the above substituent is phenyl unsubstituted or substituted with at least one of naphthyl, m-biphenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, and quinoxalinyl substituted with phenyl; biphenyl; terphenyl; naphthyl unsubstituted or substituted with phenyl; phenyl-substituted or unsubstituted carbazolyl; fluorenyl; phenanthrenyl; triphenylenyl; benzofluorenyl; dibenzofuranyl; dibenzothiophenyl; and benzocarbazolyl.

R′ ₁ and R′ ₂ may each independently be hydrogen or deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, for example, R′ ₁ and R′ ₂ are both hydrogen can be

According to an example, the organic electroluminescent compound of Formula 3 may be more specifically exemplified as the following compound, but is not limited thereto.

The compound represented by Formula 3 according to an example may be prepared by referring to a synthesis method known to those skilled in the art.

Hereinafter, an organic electroluminescent device to which the aforementioned organic electroluminescent compound and/or a plurality of types of host materials is applied will be described.

An organic electroluminescent device according to an embodiment includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light emitting layer, and the light emitting layer may include the organic electroluminescent compound represented by Formula 1 above. The organic electroluminescent device according to another embodiment of the present application includes a plurality of types including at least one first host material represented by Formula 1 and at least one second host material represented by Formula 2 and/or Formula 3 may contain a host material of

According to an example, the organic electroluminescent material of the present application includes at least one compound of compounds C-1 to C-410 represented by Formula 1 alone or in combination of two or more, and such an organic electroluminescent material is an organic electroluminescent material. It may be included in the organic layer of the light emitting device, for example, the light emitting layer.

According to another example, the organic electroluminescent material of the present application includes at least one compound among compounds C-1 to C-410 as a first host material, and compounds H1-1 to H1 as a second host material represented by Formula 2 It may include at least one compound of -131 and/or at least one compound of compounds C2-1 to C2-275, which is a second host material represented by Formula 3, and the plurality of types of host materials are the same organic layer. , for example, may be included in the light emitting layer, and may be included in different light emitting layers, respectively.

In addition to the light emitting layer, the organic layer 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 injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. It may further include more than one layer. The organic layer may further include an amine-based compound and/or a azine-based compound in addition to the light emitting material of the present application. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emitting layer, the light emission auxiliary layer, or the electron blocking layer is an amine-based compound, for example, an arylamine-based compound, a styrylarylamine-based compound, etc., as an injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emitting auxiliary material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may include a azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layer is one or more metals selected from the group consisting of group 1, group 2, 4th period transition metal, 5th period transition metal, lanthanide series metal, and organometal of a d-transition element, or at least one containing such metal It may further contain a complex compound.

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

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

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

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. In the electron buffer layer, a plurality of layers may be used for the purpose of controlling electron injection and improving interfacial properties between the light emitting layer and the electron injection layer, and two compounds may be used for each layer at the same time. The hole blocking layer is located between the electron transport layer (or electron injection layer) and the light emitting layer and blocks the holes from reaching the cathode, thereby improving the recombination probability of electrons and holes in the light emitting 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. In addition, the electron injection layer may be doped with an n-dopant.

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

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

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

The organic electroluminescent device according to an example may further include one or more dopants in the light emitting layer.

As a 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 a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt). , optionally, it may be an ortho-metalation complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases more preferably, ortho-metalated iridium complex compounds.

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

[Formula 101]

In Formula 101,

L is selected from the following structures 1 to 3;

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

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

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

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

s is an integer from 1 to 3.

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

Formation of each layer of the organic electroluminescent device of the present application is a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, ink jet printing (ink jet printing), nozzle printing (nozzle printing), slot coating (slot coating), Any one of wet film forming methods such as spin coating, dip coating, and flow coating may be applied. In the case of the wet film forming method, a thin film is formed by dissolving or dispersing the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, the solvent in which the material forming each layer is dissolved or dispersed. It can be, and any one may be used as long as there is no problem in the film-forming property.

When forming the first host material and the second host material according to an example, the film may be formed by the methods listed above, and may be formed by a co-deposition or mixed vapor deposition process. The co-deposition is a method of mixing two or more materials by putting two or more materials into each individual crucible source, evaporating the materials by applying an electric current to the two cells at the same time, and performing mixed deposition. After mixing, a current is applied to one cell to evaporate the material, and mixed deposition is performed.

According to an example, when the first host material and the second host material are present in the same layer or different layers in the organic electroluminescent device, the two host compounds may be separately formed. For example, after depositing the first host material, the second host material may be deposited.

According to one embodiment, the present invention provides a plurality of types of organic electroluminescent compound represented by Formula 1 and a first host material represented by Formula 1 and a second host material represented by Formula 2 and/or Formula 3 A display device including a host material may be provided. In addition, a display device, for example, a display device for a smartphone, tablet, notebook, PC, TV or vehicle, or a lighting device, for example, an outdoor or indoor lighting device using the organic electroluminescent device of the present invention It is possible to manufacture

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

[Example 1] Synthesis of compound C-277

1) Synthesis of compound 1-1

In a flask, 1-bromophenanthrene (50 g, 194 mmol), (5-chloro-2-formylphenyl) boronic acid ((5-chloro-2-formylphenyl) boronic acid) (43.0 g, 233 mmol), Pd(PPh ₃ ) ₄ (11.2 g, 9.72 mmol), K ₂ CO ₃ (67.2 g, 486 mmol), Toluene 600 mL, EtOH 300 mL, and H ₂ O 450 mL were added and dissolved, 140 It was stirred under reflux at ℃ for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound 1-1 (34.7 g, yield: 56%).

2) Synthesis of compound 1-2

Compound 1-1 (34.6 g, 109.2 mmol) and methoxymethyl (triphenylphosphonium) chloride ((Methoxymethyl) triphenylphosphonium chloride, MeOCH ₂ ClPPh ₃ ) (56.2 g, 163.8 mmol) were placed in 130 mL of THF and KOt-Bu (1M in THF) (163.8 mL, 163.8 mmol) was added dropwise and stirred at room temperature for 1.5 hours. After the reaction was completed, ethyl acetate and water were added to separate the organic layer, and then Compound 1-2 (28.0 g, yield: 74.2%) was obtained through a silica filter.

3) Synthesis of compound 1-3

Compound 1-2 (16.0 g, 44.8 mmol) was dissolved in 400 mL of MC, followed by dropwise addition of BF ₃ EtOEt (31.0 mL, 247.1 mmol), followed by stirring at room temperature for one day. After the reaction was completed, MC and water were added to separate the organic layer, and then compound 1-3 (13.3 g, yield: 51.5%) was obtained through a silica filter.

4) Synthesis of compound 1-4

Compound 1-3 (4.0 g, 12.8 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxa) Borolane) (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) (8.44 g, 33.2 mmol) , Pd ₂ (dba) ₃ (1.17 g, 1.28 mmol), sphos (0.525 g, 1.28 mmol), and KOAc (7.53 g, 76.7 mmol) in 120 mL of 1,4-dioxane and stirred under reflux at 130° C. for 3 hours. Separation by column chromatography gave compound 1-4 (5.00 g, yield: 96.7%).

5) Synthesis of compound C-277

In a flask, 1-4 (4.0 g, 12.7 mmol), 2-chloro-4- (dibenzo [b,d] furan-1-yl) -6-phenyl-1,3,5-triazine (2-chloro -4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine) (8.24 g, 32.5 mmol), Pd(PPh ₃ ) ₄ (0.844 g, 0.730 mmol) , K ₂ CO ₃ (5.05 g, 36.5 mmol), Toluene 40 mL, EtOH 15 mL, and H ₂ O 15 mL were added and dissolved, followed by stirring under reflux at 140° C. for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound C-277 (5.7 g, yield: 77%).

[Example 2] Synthesis of compound C-233

1-3 (5.0 g, 16.0 mmol), N-phenyldibenzo[b,d]furan-3-amine) (4.4 g, 16.8 mmol) in a flask , Pd ₂ (dba) ₃ (0.732 g, 0.800 mmol), Sphos (0.657 g, 1.60 mmol) NaOt-Bu (3.08 g, 32.0 mmol), and 80 mL of o-xylene were added and dissolved. The mixture was stirred under reflux at 190°C for 1 hour. After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound C-233 (5.0 g, yield: 58.4%).

[Example 3] Synthesis of compound C-282

1) Synthesis of compound 2-2

In a flask, 2-1 (15.0 g, 42.0 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-ratio (1,3,2-di Oxaborolane) (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) (12.8 g, 50.4 mmol ), PdCl ₂ (PPh ₃ ) ₂ (1.47 g, 2.10 mmol), KOAc (1.03 g, 10.5 mmol), and 210 mL of 1,4-dioxane were added and dissolved, followed by stirring under reflux at 140° C. for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound 2-2 (15.8 g, yield: 93.0%).

2) Synthesis of compound C-282

In a flask 2-2 (5.0 g, 12.4 mmol), 2-chloro-4- (dibenzo [b,d] furan-1-yl) -6-phenyl-1,3,5-triazine (2-chloro -4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine) (4.0 g, 11.2 mmol), Pd(PPh ₃ ) ₄ (0.647 g, 0.56 mmol) , K ₂ CO ₃ (3.87 g, 28.0 mmol), Toluene 30 mL, EtOH 15 mL, and H ₂ O 15 mL were added and dissolved, followed by stirring under reflux at 140° C. for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound C-282 (3.2 g, yield: 47.6%).

[Example 4] Synthesis of compound C-343

1) Synthesis of compound 3-1

In a flask, compound C (17.4 g, 48.5 mmol), 2-chloro-4- (dibenzo [b,d] furan-1-yl) -6-phenyl-1,3,5-triazine (2-chloro- 4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine) (21.0 g, 72.8 mmol), Pd(PPh ₃ ) ₄ (1.68 g, 1.46 mmol), K ₂ CO ₃ (20.1 g, 145.5 mmol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added and dissolved, followed by stirring under reflux at 140° C. for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound 3-1 (18.4 g, yield: 78%).

2) Synthesis of compound 3-2

Compound 3-1 (18.4 g, 37.9 mmol), bis(pinacolato)diboron (B ₂ Pin ₂ ) (13.5 g, 53.0 mmol), Pd ₂ (dba) ₃ (1.73 g, 1.89 mmol), sphos ( 1.56 g, 3.79 mmol), and KOAc (11.1 g, 114 mmol) were added to 200 mL of 1,4-dioxane and stirred at room temperature for 1.5 hours. After the reaction was completed, ethyl acetate and water were added to separate the organic layer, and then compound 3-2 (18.5 g, yield: 85%) was obtained through a silica filter.

3) Synthesis of compound 3-3

Compound 3-2 (13.2 g, 22.9 mmol) and 1-formylnaphthalen-2-yl trifluoromethanesulfonate (5.8 g, 19.1 mmol), Pd (PPh ₃ ) in a flask ) ₄ (0.661 g, 0.572 mmol), K ₂ CO ₃ (7.90 g, 57.2 mmol), Toluene 50 mL, EtOH 25 mL, and H ₂ O 25 mL were added and dissolved, followed by stirring under reflux at 140° C. for 3 hours. . After the reaction was completed, the mixture was cooled to room temperature and separated through a silica filter to obtain compound 3-3 (4.8 g, yield: 35%).

4) Synthesis of compound 3-4

Compound 3-3 (4.0 g, 8.78 mmol) and (methoxymethyl) triphenylphosphonium chloride ((Methoxymethyl) triphenylphosphonium chloride; PPh ₃ CH ₂ OMeCl) (3.40 g, 13.2 mmol) were placed in 50 mL of THF and KOt- Bu (1M in THF) (9.93 mL, 13.2 mmol) was added dropwise, followed by stirring at room temperature for 1.5 hours. After the reaction was completed, ethyl acetate and water were added to separate the organic layer, and then compound 3-4 (4.0 g, yield: 72%) was obtained through a silica filter.

5) Synthesis of compound C-343

Compound 3-4 (3.5 g, 5.54 mmol) and 400 mL of MC were dissolved in a flask, and then BF _3' EtOEt (0.894 mL, 16.6 mmol) was added dropwise and stirred at room temperature for one day. After the reaction was completed, MC and water were added to separate the organic layer, and then compound C-343 (13.3 g, yield: 51.5%) was obtained through a silica filter.

Hereinafter, for a detailed understanding of the present application, a method for manufacturing an organic electroluminescent device including the organic electroluminescent compound of the present application and properties thereof will be described.

[Device Examples 1 to 4] Preparation of red light emitting OLED according to the present invention

An OLED according to the present invention was prepared. First, the transparent electrode ITO thin film (10Ω/□) on the glass for OLED (Giomatec) substrate was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropanol and stored before use. Next, after mounting the ITO substrate in the substrate holder of the vacuum deposition equipment, the compound HI-1 as a first hole injection compound is put into a cell in the vacuum deposition equipment, and the first hole transport compound HT-1 is put into another cell , by evaporating the two materials at different rates to dope the first hole injection compound in an amount of 3 wt% with respect to the total amount of the first hole injection compound and the first hole transport compound to deposit a first hole injection layer with a thickness of 10 nm . Then, a compound HT-1 as a first hole transport layer was deposited on the first hole injection layer to a thickness of 80 nm. Then, the compound HT-2 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. After putting the first host material and the second host material described in Table 1 below as hosts in a cell in the vacuum deposition equipment, respectively, and putting compound D-39 as a dopant in another cell, the two host materials were mixed at a rate of 1:1 A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by doping with 3 wt% of the dopant with respect to the total amount of the host and the dopant by evaporating the dopant material at a different rate. Then, 35 nm of compound ETL-1 : EIL-1 as an electron transport material was deposited on the light emitting layer at a weight ratio of 50:50. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Device Comparative Examples 1 and 2] OLED manufacturing including a single host compound

An OLED was manufactured in the same manner as in Device Example 1, except that the second host material of Table 1 below was used alone as a host of the light emitting layer.

The driving voltage, luminous efficiency, luminous color, and 5,000 nits luminance of the organic electroluminescent devices according to Comparative Examples 1 and 2 and Device Examples 1 to 4 prepared as described above were 100% at 100%. The time until the drop to 95% (lifetime: T95) was measured, and the results are shown in Table 1 below.

[Device Examples 5 to 7] Preparation of blue OLED according to the present invention

OLEDs according to the invention were prepared. First, the transparent electrode ITO thin film (10Ω/□) on the glass for OLED (Giomatec) substrate was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropanol and stored before use. Next, after mounting the ITO substrate in the substrate holder of the vacuum deposition equipment, the compound HI-1 as a first hole injection compound is put into the cell in the vacuum deposition equipment, and the compound HT-3 is put into another cell, and then the two materials By evaporation at different rates, compound HI-1 and Compound HI-1 was doped in an amount of 3 wt% with respect to the total amount of compound HT-3 to deposit a hole injection layer with a thickness of 10 nm. Then, a compound HT-3 as a first hole transport layer was deposited on the hole injection layer to a thickness of 80 nm. Then, the compound HT-4 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. After putting compound BH as a host in two cells in the vacuum deposition equipment, and putting compound BD as a dopant in another cell, the dopant material was evaporated at the same time at different rates, so that the dopant was added to the total amount of the host and the dopant. A light emitting layer with a thickness of 20 nm was deposited on the hole transport layer by doping in an amount of 3 wt%. Next, the compound of Table 2 below was doped as an electron buffer layer on the light emitting layer to deposit an electron buffer layer with a thickness of 5 nm. Subsequently, an electron transport layer having a thickness of 30 nm was deposited on the electron buffer layer in a 50:50 weight ratio of ETL-1 : EIL-1 as an electron transport material. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Device Comparative Example 3] OLED manufacturing including comparative compound as an electron buffer layer

An OLED was manufactured in the same manner as in Device Example 5, except that the compound shown in Table 2 was used as the electron buffer layer.

Until the driving voltage, luminous efficiency, emission color, and light intensity based on 2,000 nits luminance of the OLEDs of Comparative Example 3 and Device Examples 5 to 7 manufactured as described above fall from 100% to 95% The time (lifetime: T95) was measured, and the results are shown in Table 2 below.

The compounds used in the device examples and device comparative examples are specifically shown in Table 3 below.

Claims (13)

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

In Formula 1,
R ₁ to R ₁₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, A fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -(L ₁ ) _n -(HAr) _m , or -L ₃ -N-(Ar ₃ ) (Ar ₄ ); adjacent substituents may be linked to each other to form a ring;
provided that at least one of R ₁ to R ₁₄ is -(L ₁ ) _n -(HAr) _m or -L ₃ -N-(Ar ₃ )(Ar ₄ );
L ₁ is a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
HAr is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
L ₃ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₃ and Ar ₄ are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
n and m are each independently an integer of 1 or 2;
when n and m are integers of 2, each of L ₁ and HAr may be the same as or different from each other;
However, the following compounds are excluded from the organic electroluminescent compound represented by Formula 1 above.

The organic electroluminescent compound according to claim 1, wherein at least one of R ₁ to R ₁₄ is -(L ₁ ) _n -(HAr) _m . The organic electroluminescent compound according to claim 1, wherein at least one of R ₁ to R ₁₄ is -L ₃ -N-(Ar ₃ )(Ar ₄ ). The substituted (C1-C30)alkyl, substituted (C2-C30)alkenyl, substituted (C6-C30)aryl(ren), substituted (3-30 membered)heteroaryl(ene ), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring group Substituted tri (C1-C30) C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, and substituted tri(C6-C30)arylsilyl The 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 membered) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl unsubstituted or substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with one or more of (C1-C30)alkyl and (3-30 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- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino substituted or unsubstituted with (C1-C30)alkyl; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And (C1-C30) Alkyl (C6-C30) at least one selected from the group consisting of aryl, the organic electroluminescent compound. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

A plurality of host materials comprising a first host material comprising the organic electroluminescent compound according to claim 1 and a second host material different from the first host material. According to claim 6, wherein the second host material comprising a compound represented by the following formula (2), a plurality of types of host material:
[Formula 2]

In Formula 2,
X ₁ and Y ₁ are each independently -N=, -NR ₆₇ -, -O-, or -S-, with the proviso that any one of X ₁ and Y ₁ is -N=, and among X ₁ and Y ₁ the other is -NR ₆₇ -, -O- or -S-;
R ₆₁ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
R ₆₂ to R ₆₄ and R ₆₇ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30) Arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L ₃ "-N(Ar ₃ ")(Ar ₄ "); Substituents may be linked to each other to form a ring;
L ₃ ″ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₃ ” and Ar ₄ ” are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C3-C30) a fused ring group of an aliphatic ring and an aromatic ring of (C6-C30), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
L ₄ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
R ₆₅ and R ₆₆ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
a is 1, b and c are each independently 1 or 2, d is an integer from 1 to 4, and when b to d are an integer of 2 or more, each of R ₆₂ to R ₆₄ may be the same or different from each other. have. According to claim 7, wherein the compound represented by Formula 2 is selected from the following compounds, a plurality of kinds of host material.

According to claim 6, wherein the second host material comprises a compound represented by the following formula (3), a plurality of types of host material:
[Formula 3]

In Formula 3,
Y is -O- or -S-;
L′ ₁ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
HAr' is a substituted or unsubstituted (3-30 membered) heteroaryl containing one or more nitrogen atoms;
R′ ₁ and R′ ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)aryl Silyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl (C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl ( C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino is; may be linked to adjacent substituents to form a ring;
e is an integer from 1 to 4, f is an integer from 1 to 3;
When e and f are each an integer of 2 or more, each R′ ₁ and each R′ ₂ may be the same as or different from each other. The host material of claim 9, wherein the compound represented by Formula 3 is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 . The organic electroluminescent device according to claim 11, comprising the organic electroluminescent compound in a light emitting layer. a first electrode; a second electrode; and at least one light emitting layer between the first electrode and the second electrode, wherein the at least one light emitting layer comprises a plurality of types of host materials according to claim 8 or 10, an organic electroluminescent device .

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