Compound and organic electroluminescent device comprising the same

Abstract

To provide a compound and an organic electroluminescent device comprising the same.SOLUTION: The present disclosure relates to a compound and an organic electroluminescent device comprising the same. By including the compound according to the present disclosure as an organic electroluminescent material, an organic electroluminescent device exhibiting low driving voltage and / or high power efficiency and / or long lifespan characteristics can be provided.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a compound and an organic electroluminescent device containing the same.

Background Art

[0002] An organic electroluminescent device (OLED) is a self-luminous display device having advantages in that it provides a wider viewing angle, a higher contrast ratio, and a faster response time. In such an OLED, holes from an anode and electrons from a cathode are injected into a light-emitting layer by the application of a voltage, and excitons having high energy are generated by the recombination of holes and electrons. The organic light-emitting compound is excited by the energy when the organic light-emitting compound returns from an excited state to a ground state, and emits light from the energy.

[0003] Unlike the already commercialized red and green high-efficiency phosphorescent materials among the light-emitting materials of OLEDs, blue phosphorescent materials have been pointed out to be not suitable for long-term use such as several years or more because they have a short lifespan and a high driving voltage, and thus fluorescent materials are used. Thus, conventional materials cannot satisfy the light-emitting characteristics of OLEDs, and therefore, the development of OLEDs containing organic electroluminescent materials having excellent performance is required.

[0004] Korean Patent Application Publication No. 2015-0121394 discloses an organic electroluminescent device including a quinazoline derivative substituted with a heterocyclic group containing at least one nitrogen atom as an electron transport layer material, and Korean Patent Application Publication No. 2017-0105040 discloses a light-emitting device including a phenanthroline derivative as an electron transport layer material. However, the above documents do not specifically disclose an organic electroluminescent device including a phenanthroline derivative as an N-type charge generation layer material according to the present disclosure.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0006] The object of the present disclosure is, firstly, to provide a compound capable of manufacturing an organic electroluminescent device having a low driving voltage, and / or high power efficiency, and / or long lifespan characteristics, and an organic electroluminescent material containing the same, and secondly, to provide an organic electroluminescent device containing the compound and the organic electroluminescent material.

Means for Solving the Problems

[0007] As a result of intensive studies to solve the above technical problems, the present inventors have found that the aforementioned object can be achieved by a compound represented by the following Formula 1, thereby completing the present invention.

Chemical Formula

[0008] In Formula 1, R1 represents hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 30 ) alkyl, or substituted or unsubstituted (3-30 membered) heteroaryl; R2 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 ) alkenyl, substituted or unsubstituted (C6-C 30)Aryl, substituted or unsubstituted (3 - 30 membered) heteroaryl, substituted or unsubstituted (C3 - C 30 )Cycloalkyl, substituted or unsubstituted (C3 - C 30 )Cycloalkenyl, substituted or unsubstituted (3 - 7 membered) heterocycloalkyl, substituted or unsubstituted (C1 - C 30 )Alkoxy, substituted or unsubstituted tri(C1 - C 30 )Alkylsilyl, substituted or unsubstituted di(C1 - C 30 )Alkyl (C6 - C 30 )Arylsilyl, substituted or unsubstituted (C1 - C 30 )Alkyldi(C6 - C 30 )Arylsilyl, substituted or unsubstituted tri(C6 - C 30 )Arylsilyl, (C3 - C 30 )A substituted or unsubstituted fused ring of an aliphatic ring and a (C6 - C 30 )aromatic ring, or represents -L-AHr, or may be linked with adjacent substituents to form a ring; However, at least one of R2 - R8 is -L-HAr; L represents a single bond, substituted or unsubstituted (C6 - C 30 )arylene, or substituted or unsubstituted (3 - 30 membered) heteroarylene; HAr represents a substituted or unsubstituted (3 - 30 membered) heteroaryl containing at least one nitrogen atom; However, when R4 or R5 is -L-HAr, compounds in which HAr is quinazoline are excluded.

[0009] Advantages of the Invention By using the compounds according to the present disclosure and the organic electroluminescent materials containing the same, an organic electroluminescent device having low driving voltage and / or high power efficiency and / or long lifespan characteristics can be manufactured.

Modes for Carrying Out the Invention

[0010] The present disclosure will be described in detail below. However, the following description is intended to explain the present invention and is not intended to limit the scope of the present invention in any way.

[0011] The present disclosure relates to a compound represented by Formula 1, an organic electroluminescent material containing the compound, and an organic electroluminescent device containing the organic electroluminescent material.

[0012] As used herein, the term "(organic electroluminescent) compound" means a compound that can be used in an organic electroluminescent device and can be included in any material layer constituting the organic electroluminescent device as needed.

[0013] As used herein, "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can contain at least one compound. The organic electroluminescent material can be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0014] As used herein, "(C1-C 30 )alkyl(ene)" means a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Examples of the above alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. As used herein, "(C3-C 30) "Cycloalkyl(ene)" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In the present disclosure, "(3-7 membered) heterocycloalkyl" means a cycloalkyl having 3 to 7 ring skeleton atoms, preferably 5 to 7 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of O, S, and N. Examples of these include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. In the present disclosure, "(C6-C 30"Aryl(ene)" means a monocyclic ring or a fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated or may contain a spiro structure. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, etc. More specifically, aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-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-fluorenyl, 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 - Chryshenyl, 2 - Chryshenyl, 3 - Chryshenyl, 4 - Chryshenyl, 5 - Chryshenyl, 6 - Chryshenyl, Benzo[c]phenanthryl, Benzo[g]chryshenyl, 1 - Triphenylenyl, 2 - Triphenylenyl, 3 - Triphenylenyl, 4 - Triphenylenyl, 3 - Fluoranthenyl, 4 - Fluoranthenyl, 8 - Fluoranthenyl, 9 - Fluoranthenyl, Benzofluoranthenyl, 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]fluorenyl, 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-phenanthrenylExamples include 9,9,10,10 - tetramethyl - 9,10 - dihydro - 4 - phenanthrenyl and the like. In the present disclosure, "(3 - to 30 - membered) heteroaryl(ene)" refers to an aryl having 3 to 30 ring - skeleton atoms containing at least 1 heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, and the number of ring - skeleton carbon atoms is preferably 3 to 30, more preferably 5 to 20. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above heteroaryl may be a monocyclic ring, or a condensed ring condensed with at least 1 benzene ring, and may also be partially saturated. Also, the above heteroaryl or heteroarylene in this specification may be formed by bonding at least 1 heteroaryl or aryl group to a heteroaryl group via a single bond, and may include a spiro structure. Specific examples of heteroaryl include monocyclic ring - type heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroxazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidylindolyl, benzopyrimidylindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl,Examples of the condensed ring heteroaryl include dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenokazinolinyl, thiocromenokazinolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, indenocarbazolyl, etc. 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-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 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, azacarbazol - 1 - yl, azacarbazol - 2 - yl, azacarbazol - 3 - yl, azacarbazol - 4 - yl, azacarbazol - 5 - yl, azacarbazol - 6 - yl, azacarbazol - 7 - yl, azacarbazol - 8 - yl, azacarbazol - 9 - yl, 1 - phenanthridinyl, 2 - phenanthridinyl, 3 - phenanthridinyl, 4 - phenanthridinyl, 6 - phenanthridinyl, 7 - phenanthridinyl, 8 - phenanthridinyl, 9 - phenanthridinyl, 10 - phenanthridinyl, 1 - acridinyl, 2 - acridinyl, 3 - acridinyl, 4 - acridinyl, 9 - acridinyl, 2 - oxazolyl, 4 - oxazolyl, 5 - oxazolyl, 2 - oxadiazolyl, 5 - oxadiazolyl, 3 - furazanyl, 2 - thienyl, 3 - thienyl, 2 - 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 - methylpyrrol - 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, 2-naphtho[2,3-b]-benzofuranyl, 3-naphtho[2,3-b]-benzofuranyl, 4-naphtho[2,3-b]-benzofuranyl, 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]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl,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-germaf luorenyl, 2-germaf luorenyl, 3-germaf luorenyl, 4-germaf luorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. may also be used. Further, "heteroaryl(ene)" is,It can be classified into a heteroaryl(ene) having electronic properties and a heteroaryl(ene) having hole properties. The heteroaryl(ene) having electronic properties is a substituent in which electrons are relatively abundant in the mother nucleus, and may be, for example, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolyl, etc. The heteroaryl(ene) having hole properties is a substituent having relatively insufficient electrons in the mother nucleus, and may be, for example, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. In the present specification, the term "(C3~C, 30 ) condensed ring of an aliphatic ring and a (C6~C 30 ) aromatic ring" means a ring formed by condensation of at least one aliphatic ring having 3 to 30 ring-skeleton carbon atoms, preferably 3 to 25 carbon atoms, more preferably 3 to 18 carbon atoms, and at least one aromatic ring having 6 to 30 ring-skeleton carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms. For example, the condensed ring may be a condensed ring of at least one benzene and at least one cyclohexane, or a condensed ring of at least one naphthalene and at least one cyclopentane, etc. In the present specification, the carbon atoms in the condensed ring of the (C3~C 30 ) aliphatic ring and the (C6~C 30 ) aromatic ring can be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. "Halogen" in the present disclosure includes F, Cl, Br, and I.

[0015] Furthermore, "ortho (o-)", "meta (m-)", and "para (p-)" are intended to indicate the substitution positions of all substituents. The ortho position represents, for example, a compound having substituents adjacent to each other at the 1- and 2-positions of benzene. The meta position indicates the substitution position next to the directly adjacent substitution position, for example, a compound having substituents at the 1- and 3-positions of benzene. The para position indicates the substitution position next to the meta position, for example, a compound having substituents at the 1- and 4-positions of benzene.

[0016] As used herein, the term "ring formed by linking adjacent substituents" means a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof formed by linking or condensing two or more adjacent substituents, preferably it may be a substituted or unsubstituted (5- to 25-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Further, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20, and according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the fused ring may be, 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, a substituted or unsubstituted benzofluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, etc.

[0017] Furthermore, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced by another atom or another functional group, i.e., a substituent. Unless otherwise specified, the substituent does not have to be limited to hydrogen at the position where the substituent can be substituted. When two or more hydrogen atoms in a functional group are each substituted by a substituent, the substituents may be the same or different from each other. For example, the "substituent in which two or more substituents are linked" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl or may be interpreted as one substituent in which two heteroaryls are linked. Preferably, substituted alkyl, substituted alkenyl, substituted aryl(ene), substituted heteroaryl(ene), substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the substituted condensed ring of an aliphatic ring and an aromatic ring in the formula of the present disclosure are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 )alkyl, halo(C1-C 30 )alkyl, (C2-C 30 )alkenyl, (C2-C 30 )alkynyl, (C1-C 30 )alkoxy, (C1-C 30 )alkylthio, (C3-C 30 )cycloalkyl, (C3-C 30 )cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C 30 )aryloxy, (C6-C 30 )arylthio, unsubstituted or (C6-C 30 )aryl-substituted (5-30 membered) heteroaryl, unsubstituted or (5-30 membered) heteroaryl-substituted (C6-C 30 )aryl, tri(C1-C 30 )alkylsilyl, tri(C6-C 30 )arylsilyl, di(C1-C 30 )alkyl(C6-C 30 )arylsilyl, (C1-C 30)Alkyldi(C6-C 30 )Arylsilyl, (C3-C 30 )Aliphatic ring and (C6-C 30 )Condensed ring of aromatic ring, amino, mono- or di(C1-C 30 )Alkylamino, substituted or unsubstituted mono- or di(C6-C 30 )Arylamino, (C1-C 30 )Alkyl(C6-C 30 )Arylamino, mono- or di(3-30 membered) heteroarylamino, (C1-C 30 )Alkyl(3-30 membered) heteroarylamino, (C6-C 30 )Aryl(3-30 membered) heteroarylamino, (C1-C 30 )Alkylcarbonyl, (C1-C 30 )Alkoxycarbonyl, (C6-C 30 )Arylcarbonyl, (C6-C 30 )Arylphosphinyl, di(C6-C 30 )Arylboronyl, di(C1-C 30 )Alkylboronyl, (C1-C 30 )Alkyl(C6-C 30 )Arylboronyl, (C6-C 30 )Al(C1-C 30 )Alkyl, and (C1-C 30 )Alkyl(C6-C 30 )Aryl is substituted by at least one selected from the group consisting of.

[0018] When a substituent is not shown in the chemical formula or compound structure of the present disclosure, it may mean that all positions where it can be present as a substituent are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be from 0% to 100%. When a substituent is not shown in the chemical formula or compound structure of the present disclosure and deuterium is not explicitly excluded, for example, when the deuterium content is 0%, the hydrogen content is 100%, all substituents are hydrogen, and hydrogen and deuterium may be mixed and used together in the compound. Deuterium is an element having a deuteron composed of one proton and one neutron as a nucleus, is one of the isotopes of hydrogen, can be represented by hydrogen-2, and the element symbol may be D or 2 H. Isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0019] As used herein, "their combinations" means combining one or more components of the corresponding list to form a known or chemically stable form that a person skilled in the art can conceive from the corresponding list. For example, an alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group, a halogen and an alkyl can be combined to form a halogenated alkyl substituent, and a halogen, an alkyl, and an aryl can be combined to form a halogenated arylalkyl. For example, a preferred combination of substituents may contain up to 50 atoms excluding hydrogen and deuterium, or may contain up to 40 atoms excluding hydrogen and deuterium, or may contain up to 30 atoms excluding hydrogen and deuterium, or in many cases, a preferred combination of substituents may contain up to 20 atoms excluding hydrogen and deuterium.

[0020] In the formulas of the present disclosure, when a plurality of substituents are represented by the same symbol, each of these substituents represented by the same symbol may be the same as or different from each other.

[0021] Hereinafter, a compound according to an embodiment will be described.

[0022] A compound according to an embodiment of the present disclosure is represented by the following formula 1. [Chemical Formula]

[0023] In formula 1, R1 represents hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 30 ) alkyl, or substituted or unsubstituted (3-30 membered) heteroaryl; R2 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 ) alkenyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C3-C 30 ) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) alkyldi(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, a substituted or unsubstituted condensed ring of an (C3-C 30 ) aliphatic ring and a (C6-C 30 ) aromatic ring, or -L-AHr, or may be linked with adjacent substituents to form a ring; However, at least one of R2 to R8 is -L-HAr; L represents a single bond, a substituted or unsubstituted (C6-C 30 ) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom; However, when R4 or R5 is -L-HAr, compounds in which HAr is quinazoline are excluded.

[0024] In one embodiment, R1 is hydrogen, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 10 ) alkyl, or substituted or unsubstituted (5-30 membered) heteroaryl, preferably hydrogen, halogen, phenyl unsubstituted or substituted with (C1-C 10 ) alkyl or (5-30 membered) heteroaryl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, (C1-C 10 ) alkyl unsubstituted or substituted with deuterium, or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably hydrogen, halogen, phenyl unsubstituted or substituted with (C1-C4) alkyl or (5-25 membered) heteroaryl, unsubstituted p-biphenyl, unsubstituted m-biphenyl, unsubstituted o-biphenyl, unsubstituted m-terphenyl, unsubstituted o-terphenyl, (C1-C4) alkyl unsubstituted or substituted with deuterium, or substituted or unsubstituted (5-18 membered) heteroaryl.

[0025] For example, R1 may be hydrogen, F, phenyl substituted with unsubstituted or tert-butyl or benzotriazolyl, unsubstituted p-biphenyl, unsubstituted m-biphenyl, unsubstituted o-biphenyl, unsubstituted m-terphenyl, unsubstituted o-terphenyl, methyl substituted with deuterium, unsubstituted or deuterium-substituted tert-butyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted benzotriazolyl.

[0026] In one embodiment, R2 to R8 may each independently be hydrogen, substituted or unsubstituted (C6~C 30 ) aryl, or -L-HAr, and at least one of R2 to R8 is -L-HAr, preferably hydrogen, substituted or unsubstituted (C6~C 25 ) aryl, or -L-HAr, more preferably hydrogen, substituted or unsubstituted (C6~C 18 ) aryl, or -L-HAr. For example, R2 to R8 may each independently be hydrogen, substituted or unsubstituted phenyl, or -L-HAr.

[0027] According to one embodiment, the compound represented by Formula 1 may be represented by any one of Formulas 1-1 to 1-7 below.

Chemical formula

[0028] In Formulas 1-1 to 1-7, R1, L and HAr are as defined in Formula 1; R2 to R8 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6~C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0029] In one embodiment, L is a single bond or substituted or unsubstituted (C6~C 30An arylene, preferably a single bond or a substituted or unsubstituted (C6-C 25 ) arylene, more preferably a single bond or a substituted or unsubstituted (C6-C 18 ) arylene may be used. For example, L may be a single bond, unsubstituted phenylene or phenylene substituted with at least one phenyl, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0030] In one embodiment, HAr is a substituted or unsubstituted (5-30 membered) heteroaryl containing at least one nitrogen, preferably containing at least one nitrogen atom and being unsubstituted, or a (5-25 membered) heteroaryl substituted with a (C6-C 30 ) aryl or a (5-30 membered) heteroaryl, more preferably containing at least two nitrogen atoms and being unsubstituted, or a (5-18 membered) heteroaryl substituted with a (C6-C 25 ) aryl or a (5-25 membered) heteroaryl may be used. For example, HAr may be unsubstituted quinazolinyl or quinazolinyl substituted with at least one phenyl or at least one pyridyl, unsubstituted quinoxalinyl or quinoxalinyl substituted with at least one phenyl or at least one pyridyl, or unsubstituted benzotriazolyl or benzotriazolyl substituted with phenyl or dimethylfluorenyl.

[0031] In one embodiment, HAr may be represented by the following Formula 1-a or 1-b.

Chemical formula

[0032] In Formula 1-a or 1-b,

Chemical formula

[0033] In one embodiment, X1 can be N, and X2 can be CR 12 wherein.

[0034] In one embodiment, X1 can be CR 12 wherein, and X2 can be N.

[0035] In one embodiment, R 11 and R 12 each independently can be a substituted or unsubstituted (C6-C 30 ) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C 25 ) aryl or a substituted or unsubstituted (5-25 membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C 18 ) aryl or a substituted or unsubstituted (5-18 membered) heteroaryl. For example, R 11 and R 12 each independently can be phenyl substituted with unsubstituted or deuterium-substituted methyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0036] In one embodiment, Y1 and Y3 can be N, and Y2 can be NR 14 where R 14 can be a substituted or unsubstituted (C6-C 30 ) aryl.

[0037] In one embodiment, Y1 and Y3 can be N, and Y2 can be NR 14 where R 14 can be a moiety directly linked to L.

[0038] In one embodiment, R 13 and R 14 can each independently be hydrogen, deuterium, or a substituted or unsubstituted (C6-C 30 ) aryl, preferably hydrogen, deuterium, or a substituted or unsubstituted (C6-C 25 ) aryl, more preferably hydrogen, deuterium, or a substituted or unsubstituted (C6-C 18 ) aryl. For example, R 13 and R 14 can each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted fluorenyl.

[0039] According to one embodiment, the compound represented by Chemical Formula 1 can be more specifically exemplified by, but not limited to, the following compounds:

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0040] According to another embodiment, the present disclosure provides a compound selected from the following compounds, and an organic electroluminescent material containing the same.

Chem.

Chem.

Chem.

[0041] The compound represented by Formula 1 according to the present disclosure can be included in the N-type charge generation layer (CGL) of an organic electroluminescent device. In the compound of Formula 1 according to the present disclosure, the phenanthroline moiety has a relatively electron-rich sp 2It contains hybrid orbital nitrogen. In particular, since the phenanthroline moiety has a structure in which two nitrogens are adjacent to each other, it can form a covalent bond with surrounding hydrogen or coordinate with an alkali metal or alkaline earth metal such as Li and Yb. When a compound of Formula 1 having such a phenanthroline moiety is applied to an N-type charge generation layer, the phenanthroline moiety can capture a doped alkali metal or alkaline earth metal and increase the electron density within the molecule, thereby improving the electron injection and mobility. Further, when the compound of Formula 1 according to the present disclosure is applied to the N-type charge generation layer of an organic electroluminescent device, the nitrogen of the phenanthroline moiety can combine with an alkali metal or alkaline earth metal that is a dopant of the N-type charge generation layer to form a gap state. Therefore, the energy level difference between the N-type charge generation layer and the P-type charge generation layer is relaxed, and as a result, electrons can be smoothly transferred from the N-type charge generation layer to the electron transport layer.

[0042] An organic electroluminescent device according to an embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to an embodiment, a single light-emitting unit (light-emitting unit) may be formed in a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device includes a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer laminated between the first electrode and the second electrode and emitting light in a specific wavelength range, and may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units. The plurality of light-emitting units may emit the same color or different colors. In addition, one light-emitting unit may also include one or more light-emitting layers, and the plurality of light-emitting layers may be light-emitting layers of the same color or different colors. This may include one or more charge generation layers disposed between each light-emitting unit. The charge generation layer refers to a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer can be disposed between each light-emitting unit. The plurality of charge generation layers here may be the same as or different from each other. By disposing the charge generation layer between the light-emitting units, the current efficiency can be increased in each light-emitting unit, and the charge can be smoothly distributed. Specifically, the charge generation layer is provided between two adjacent stacks and can help drive a tandem organic electroluminescent device using only the pair of anode and cathode without a separate internal electrode disposed between the stacks.

[0043] Hereinafter, an organic electroluminescent device to which the above-described organic electroluminescent material according to the present disclosure is applied will be described.

[0044] An organic electroluminescent device according to an embodiment of the present invention includes a first electrode, a second electrode facing the first electrode, a plurality of light-emitting units disposed between the first electrode and the second electrode, and at least one charge generation layer disposed between adjacent light-emitting units. The light-emitting unit includes at least one light-emitting layer, and the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer. In this case, the N-type charge generation layer includes at least one compound selected from the compounds represented by Formula 1 according to the present disclosure, for example, Compounds C-1 to C-332, or Compounds C2-1 to C2-38.

[0045] An organic electroluminescent device according to an embodiment includes at least two light-emitting units, the charge generation layer is disposed between adjacent light-emitting units, and the number of light-emitting units may be increased. According to an embodiment, at least one of the plurality of light-emitting units may include a first light-emitting layer and a second light-emitting layer adjacent to each other.

[0046] One of the first electrode and the second electrode may be an anode for injecting holes, and the other may be a cathode for injecting electrons. In this case, the first electrode and the second electrode may be formed of a transmissive conductive material, a semi-transmissive conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type depending on the type of material forming the first electrode and the second electrode.

[0047] According to an embodiment, each of the light-emitting units includes each of a hole transport layer, each of the light-emitting layers, and each of an electron transport layer.

[0048] The first light-emitting unit includes a hole injection layer disposed between the first electrode and the first light-emitting layer, a first hole transport layer disposed between the hole injection layer and the first light-emitting layer, and a first electron transport layer disposed between the first light-emitting layer and the charge generation layer.

[0049] The second light-emitting unit includes a second hole transport layer, a second light-emitting layer, a second electron transport layer, and an electron injection layer. The second hole transport layer is disposed between the charge generation layer and the second light-emitting layer, and the second light-emitting layer is disposed between the second hole transport layer and the second electrode. In addition, the second electron transport layer is disposed between the second light-emitting layer and the second electrode, and the electron injection layer is disposed between the second electron transport layer and the second electrode.

[0050] The hole injection layer may be formed in multiple layers for the purpose of reducing the hole injection barrier (or hole injection voltage) from the anode to the first hole transport layer or the electron blocking layer, and each layer may use two kinds of compounds simultaneously. In addition, the hole injection layer may be doped with a p-type dopant. Furthermore, the electron blocking layer can be disposed between the hole transport layer (or hole injection layer) and the first light-emitting layer and the second light-emitting layer, and can prevent the overflow of electrons from the light-emitting layer, confine excitons in the light-emitting layer, and prevent light leakage. The first hole transport layer and the second hole transport layer or the electron blocking layer may be formed from multiple layers, and each layer may use multiple compounds. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer.

[0051] The organic electroluminescent device according to one embodiment may include a light-emitting auxiliary layer disposed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport, or to prevent the overflow of electrons. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent the overflow of holes. In addition, the hole auxiliary layer may be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby making it possible to control the charge balance.

[0052] The first light-emitting layer and the second light-emitting layer are layers that emit light containing a host and a dopant, and can be a single layer or a plurality of layers stacked with two or more layers. In this specification, the host mainly has a function of promoting the recombination of electrons and holes and confining excitons in the light-emitting layer, and the dopant has a function of efficiently emitting excitons obtained by recombination. The dopant material of the first light-emitting layer and the second light-emitting layer can be doped in an amount of less than 25% by weight, preferably less than 17% by weight, more preferably less than 10% by weight based on the total of the host material and the dopant material.

[0053] According to one embodiment, the first light-emitting layer and the second light-emitting layer can be an anthracene derivative compound as a host material. For example, the host material can be a fluorescent blue host material. In addition, the first light-emitting layer and the second light-emitting layer can further include one or more dopants. As the dopant included in the organic electroluminescent device of the present disclosure, one or more phosphorescent or fluorescent dopants may be used. For example, the dopant material can be a fluorescent blue dopant material.

[0054] According to one embodiment of the present disclosure, an organic electroluminescent device having a tandem structure has a charge generation layer disposed between a first light-emitting unit and a second light-emitting unit, which increases the current efficiency generated in each light-emitting layer and smoothly distributes charges. The charge generation layer is located adjacent to the first light-emitting unit and includes an N-type charge generation layer that supplies electrons to the first light-emitting unit, and a P-type charge generation layer that is located adjacent to the second light-emitting unit and supplies holes to the second light-emitting unit.

[0055] That is, the charge generation layer is disposed between the first light-emitting unit and the second light-emitting unit, and the first light-emitting unit and the second light-emitting unit are connected by the charge generation layer. The charge generation layer may be a PN junction charge generation layer in which the N-type charge generation layer and the P-type charge generation layer are disposed adjacent to each other and joined.

[0056] The N-type charge generation layer supplies electrons to the first electron transport layer of the first light-emitting unit, and the first electron transport layer supplies electrons to the first light-emitting layer adjacent to the first electrode.

[0057] According to an embodiment of the present disclosure, the N-type charge generation layer includes the aforementioned compound represented by Formula 1. The compound of Formula 1 has excellent electron mobility, and thus has excellent electron injection and transport capabilities. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device as an N-type charge generation layer material, an increase in the gradual driving voltage and a decrease in the lifespan of the device can be prevented.

[0058] According to another embodiment, the N-type charge generation layer includes at least one compound selected from Compounds C2-1 to C2-38.

[0059] According to an embodiment, the N-type charge generation layer may further include an N-type dopant in order to improve the electron injection characteristics into the N-type charge generation layer. For example, usable N-type dopants may further include alkali metals such as Li, Na, K, Rb, Cs, Fr, Yb, alkaline earth metals such as Be, Mg, Ca, Sr, Ba, Ra, or one or more complex compounds of such metals commonly used in the art. In the N-type charge generation layer, the doping concentration of the dopant may be 0.5% to 10% of the compound of Formula 1.

[0060] The P-type charge generation layer supplies holes to the second hole transport layer of the second light-emitting unit, and the second hole transport layer supplies holes to the second light-emitting layer adjacent to the second electrode. That is, the P-type charge generation layer is used as a hole injection layer and may contain only the hole injection layer material, or may contain the hole injection layer material in a mixture of hole transport materials.

[0061] In one embodiment, the P-type charge generation layer may be formed from a metal or an organic material doped with a P-type dopant. For example, the metal may be formed from one or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, as the P-type dopant and the host material used for the P-type doped organic material, generally used materials can be used.

[0062] The light-emitting unit according to one embodiment may further include a hole blocking layer between the light-emitting layer and the electron transport layer. The hole blocking layer is a layer that can prevent holes from reaching the cathode, thereby improving the recombination probability of electrons and holes in the light-emitting layer. For the hole blocking layer or the first and second electron transport layers, a plurality of layers can be used, and a plurality of compounds can be used for each layer. In addition, the first and second electron injection layers may be doped with an n-type dopant.

[0063] The organic electroluminescent device includes a first electrode and a second electrode facing each other, and an organic layer disposed between the first electrode and the second electrode. The organic layer may include a first light-emitting unit, a second light-emitting unit, a third light-emitting unit, a first charge generation layer, and a second charge generation layer. In another embodiment, four or more light-emitting units and three or more charge generation layers may be disposed between the first electrode and the second electrode.

[0064] The first charge generation layer is disposed between the first light-emitting unit and the second light-emitting unit, the second charge generation layer is disposed between the second light-emitting unit and the third light-emitting unit, and the first light-emitting unit, the first charge generation layer, the second light-emitting unit, the second charge generation layer, and the third light-emitting unit are sequentially stacked on the first electrode. That is, the first light-emitting unit is disposed between the first electrode and the first charge generation layer, the second light-emitting unit is disposed between the first charge generation layer and the second charge generation layer, and the third light-emitting unit is disposed between the second electrode and the second charge generation layer.

[0065] The first light-emitting unit may include a hole injection layer, a first hole transport layer, a first light-emitting layer, and a first electron transport layer that are sequentially stacked on the first electrode. At this time, the first electron transport layer is disposed between the first light-emitting layer and the first charge generation layer. The hole injection layer, the first hole transport layer, the first light-emitting layer, and the first electron transport layer have been described above, respectively, and thus their descriptions are omitted.

[0066] The second light-emitting unit may include a second hole transport layer, a second light-emitting layer, and a second electron transport layer. The second hole transport layer is disposed between the first charge generation layer and the second light-emitting layer, and the second electron transport layer is disposed between the second light-emitting layer and the second charge generation layer. The second hole transport layer, the second light-emitting layer, and the second electron transport layer have been described above, respectively, and thus their descriptions are omitted.

[0067] The third light-emitting unit may include a third hole transport layer, a third light-emitting layer, a third electron transport layer, and an electron injection layer. The third hole transport layer is disposed between the second charge generation layer and the third light-emitting layer, the third electron transport layer is disposed between the third light-emitting layer and the second electrode, and the electron injection layer is disposed between the third electron transport layer and the second electrode. The third hole transport layer, the third electron transport layer, and the electron injection layer may have the same characteristics as the second hole transport layer, the second electron transport layer, and the electron injection layer described above, respectively, and their descriptions are omitted. In addition, the third light-emitting layer may have the same characteristics as the first light-emitting layer or the second light-emitting layer. For example, the third light-emitting layer may include a fluorescent blue host material and a fluorescent blue dopant material.

[0068] In the second charge generation layer, the N-type charge generation layer is disposed between the second electron transport layer and the third hole transport layer, and the P-type charge generation layer is disposed between the N-type charge generation layer and the third hole transport layer. The first charge generation layer and the second charge generation layer generate charges or separate charges into holes and electrons to supply electrons and holes to the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit. The N-type charge generation layer and the P-type charge generation layer may have the same characteristics as the N-type charge generation layer and the P-type charge generation layer described above, respectively, and their descriptions are omitted.

[0069] In one embodiment according to the present disclosure, at least one of the N-type charge generation layer and the P-type charge generation layer contains the compound represented by the above formula 1.

[0070] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or wet film formation methods such as spin coating, dip coating, flow coating method, etc. can be used. When using a wet film formation method, the thin film can be formed by dissolving or dispersing the material for forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent that can dissolve or disperse the material for forming each layer and has no problem with film-forming ability.

[0071] When forming a layer with the compound of formula 1 according to one embodiment, the layer can be formed by the methods listed above, and in many cases, it can be formed by co-evaporation or co-deposition. Co-evaporation is a co-deposition method in which two or more materials are placed in their respective individual crucible sources, an electric current is passed through both cells simultaneously to evaporate the materials, and co-deposition is performed. Co-deposition is a co-deposition method in which two or more materials are mixed in one crucible source before evaporation, and then an electric current is passed through one cell to evaporate the materials.

[0072] In one embodiment, when organic electroluminescent materials are present in the same layer or different layers within the organic electroluminescent device, they can be deposited individually.

[0073] According to one embodiment, the present disclosure can provide a display device containing the compound represented by formula 1. In addition, the organic electroluminescent device of the present disclosure can be used for the manufacture of display devices such as smartphones, tablets, notebooks, PCs, TVs, etc., or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

[0074] Hereinafter, in order to understand the present disclosure in detail, a method for preparing a compound according to the present disclosure will be described with reference to a method for synthesizing a representative compound or an intermediate compound.

Examples

[0075] [Example 1] Synthesis of Compound C-1

Chemical formula

[0076]

Table 1

[0077] [Example 2] Synthesis of Compound C-3

Chemical formula

[0078] [Table 2]

[0079] [Example 3] Synthesis of Compound C-5 [Chemical formula] 2-Chloro-9-phenyl-1,10-phenanthroline (7.1 g, 24 mmol), 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) quinazoline (10 g, 24 mmol), PdCl2amphos (1.2 g, 1.7 mmol), Aliquat 336 (1.0 g, 2.5 mmol), Na2CO3 (5.2 g, 49 mmol), 122 mL of toluene, and 41 mL of distilled water were added to a flask and stirred at 140 °C under reflux. After 3 hours, the mixture was cooled to room temperature, and the obtained solid was filtered and separated by column chromatography to obtain C-5 (8.3 g, yield: 64%).

[0080] [Table 3]

[0081] [Example 4] Synthesis of Compound C-57 [Chem.] 2-Phenyl-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (7.0 g, 15.27 mmol), 5-bromo-2,3-diphenylquinoxaline (5.5 g, 15.27 mmol), Pd(amphos)Cl2 (0.8 g, 1.07 mmol), Aliquat 336 (0.6 g, 1.53 mmol), Na2CO3 (3.2 g, 30.54 mmol), 76 mL of toluene and 25 mL of distilled water were added to a flask and stirred at 130 °C under reflux. After 2 hours, the mixture was cooled to room temperature and the layers were separated. Next, this was filtered using silica and recrystallized to obtain Compound 57 (6.8 g, yield: 72.72%).

[0082] [Table 4]

[0083] [Example 5] Synthesis of Compound C-4 [Chem.] 2-Chloro-1,10-phenanthroline (5.0 g, 23.3 mmol), 2,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (10 g, 24.5 mmol), Pd(amphos)Cl2 (1.15 g, 1.63 mmol), Na2CO3 (4.94 g, 46.6 mmol), Aliquat 336 (0.188 g, 0.466 mmol), 50 mL of toluene and 50 mL of distilled water were added to a flask and stirred at 140 °C under reflux. After 12 hours, the mixture was cooled to room temperature and the layers were separated. Next, this was filtered using silica and recrystallized to obtain Compound C-4 (4.7 g, yield: 44%).

[0084] [Table 5]

[0085] [Example 6] Synthesis of Compound C-137 [Chemical Formula] 2-Chloro-9-phenyl-1,10-phenanthroline (8.6 g, 29.6 mmol), 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[d][1,2,3]triazole (11.4 g, 35.5 mmol), Pd(amphos)Cl2 (1.8 g, 2.48 mmol), Aliquat 336 (1.4 g, 3.55 mmol), Na2CO3 (7.5 g, 71.0 mmol), 177 mL of toluene and 59 mL of distilled water were added to a flask and stirred at 130 °C under reflux. After 3 hours, the mixture was cooled to room temperature and the layers were separated. Next, this was filtered using silica and recrystallized to obtain Compound 137 (3.5 g, yield: 26.35%).

[0086] [Table 6]

[0087] [Example 7] Synthesis of Compound C-6 [Chemical Formula] Compound 7-1 (10.0 g, 24.49 mmol), Compound 7-2 (7.8 g, 26.94 mmol), Pd(amphos)Cl2 (1.2 g, 1.71 mmol), Aliquat 336 (1.0 g, 2.45 mmol), and Na2CO3 (5.2 g, 48.98 mmol) in a flask were dissolved in 122 mL of toluene and 41 mL of distilled water and stirred at 130 °C under reflux. After 2 hours and 30 minutes, the mixture was cooled to room temperature and the layer of the obtained solid reaction product was separated. Next, this was filtered using silica and recrystallized. Then, this was separated by column chromatography to obtain Compound C-6 (3.5 g, yield: 26.63%).

[0088] [Table 7]

[0089] [Example 8] Synthesis of Compound C-200 [Chemical Formula] Compound 8-1 (8.0 g, 17.45 mmol), Compound 8-2 (5.3 g, 19.19 mmol), Pd(amphos)Cl2 (0.9 g, 1.22 mmol), Aliquat 336 (0.7 g, 1.74 mmol), and Na2CO3 (3.7 g, 34.90 mmol) placed in a flask were dissolved in 87 mL of toluene and 29 mL of distilled water, and stirred at 130 °C under reflux. After 2 hours, the mixture was cooled to room temperature and the layers were separated. Next, this was filtered using silica and recrystallized to obtain Compound C-200 (3.3 g, yield: 35.98%).

[0090] [Table 8]

[0091] [Example 9] Synthesis of Compound C-12 [Chemical Formula] Compound 9-1 (7.8 g, 23.91 mmol), Compound 9-2 (7.7 g, 35.87 mmol), Pd(amphos)Cl2 (1.2 g, 1.67 mmol), Aliquat 336 (1.0 g, 2.39 mmol), and Na2CO3 (5.1 g, 47.82 mmol) placed in a flask were dissolved in 120 mL of toluene and 40 mL of distilled water, and stirred at 130 °C under reflux. After 2 hours, the mixture was cooled to room temperature and the layers were separated. Next, this was filtered using silica and recrystallized to obtain Compound C-12 (8.1 g, yield: 73.56%).

[0092] [Table 9]

[0093] [Example 10] Synthesis of Compound C-82 [Chemical Formula] Compound 10-1 (15.0 g, 32.72 mmol), Compound 10-2 (13.0 g, 35.99 mmol), Pd(amphos)Cl2 (1.6 g, 2.29 mmol), Aliquat 336 (1.3 g, 3.27 mmol), and Na2CO3 (6.9 g, 65.44 mmol) placed in a flask were dissolved in 165 mL of toluene and 55 mL of distilled water, and stirred at 130 °C under reflux. After 3 hours, the mixture was cooled to room temperature, and the layers were separated. Next, this was filtered using silica to obtain Compound C-82 (13.0 g, yield: 64.83%).

[0094] [Table 10]

[0095] [Example 11] Synthesis of Compound C-76 [Chemical Formula] Compound 11-1 (17.0 g, 37.1 mmol), Compound 11-2 (12.0 g, 37.9 mmol), Pd(PPh3)4 (0.416 g, 1.85 mmol), SPhos (1.52 g, 3.71 mmol), and K2CO3 (15.4 g, 111 mmol) placed in a flask were dissolved in 340 mL of THF and 34 mL of distilled water, and stirred at 70 °C under reflux. After 3 hours, the mixture was cooled to room temperature and filtered through silica to obtain Compound C-76 (15.3 g, yield: 67.4%).

[0096] [Table 11]

[0097] [Example 12] Synthesis of Compound C-151 [Chemical Formula] Compound 12-1 (15.7 g, 49.0 mmol), Compound 12-2 (5.5 g, 22.1 mmol), Pd(amphos)Cl2 (2.42 g, 3.43 mmol), Aliquat 336 (1.98 g, 4.9 mmol), and Na2CO3 (10.4 g, 98.0 mmol) in a flask were dissolved in 200 mL of toluene and 50 mL of distilled water, and stirred at 100 °C under reflux for 18 hours. After 18 hours, methanol was added, and the resulting solid reaction product was cooled to room temperature, and the layers were separated. Next, this was separated by a silica filter to obtain Compound C-151 (7.5 g, yield: 59.9%).

[0098] [Table 12]

[0099] [Example 13] Synthesis of Compound C-213 [Chemical formula] Compound 13-1 (8.8 g, 23 mmol), Compound 13-2 (8.5 g, 24 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and K2CO3 (6.3 g, 46 mmol) in a flask were dissolved in 125 mL of toluene, 25 mL of ethanol, and 25 mL of distilled water, and stirred at 100 °C under reflux for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature, the organic matter was extracted with methylene chloride, and then distilled under reduced pressure. Then, this was separated by column chromatography to obtain Compound C-213 (9.0 g, yield: 73%).

[0100] [Table 13]

[0101] [Example 14] Synthesis of Compound C-170 [Chemical formula] Compound 14-1 (8.8 g, 23 mmol), Compound 14-2 (8.5 g, 24 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and K2CO3 (6.3 g, 46 mmol) in the flask were dissolved in 125 mL of toluene, 25 mL of ethanol, and 25 mL of distilled water, and stirred at 100 °C for 4 hours under reflux. After the reaction was completed, the reaction product was cooled to room temperature, the organic matter was extracted with methylene chloride, and then distilled under reduced pressure. After solidifying with ethyl acetate, this was separated by column chromatography to obtain Compound C-170 (7.5 g, yield: 61%).

[0102] [Table 14]

[0103] [Example 15] Synthesis of Compound C-300 [Chemical formula] Compound 15-1 (5.0 g, 13.08 mmol), Compound 15-2 (4.6 g, 14.39 mmol), Pd(amphos)Cl2 (0.6 g, 0.91 mmol), Aliquat 336 (1.1 g, 2.61 mmol), and Na2CO3 (2.8 g, 26.16 mmol) in the flask were dissolved in 65 mL of toluene and 22 mL of distilled water, and stirred at 130 °C for 5 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated, and then the obtained product was filtered through celite. Then, this was filtered through silica and recrystallized to obtain Compound C-300 (4.8 g, yield: 69%).

[0104] [Table 15]

[0105] [Example 16] Synthesis of Compound C-302 [Chemical formula] Compound 16-1 (5.0 g, 13.08 mmol), Compound 16-2 (4.6 g, 14.39 mmol), Pd(amphos)Cl2 (0.6 g, 0.91 mmol), Aliquat 336 (1.1 g, 2.61 mmol), and Na2CO3 (2.8 g, 26.16 mmol) in a flask were dissolved in 65 mL of toluene and 22 mL of distilled water, and stirred at 130 °C for 5 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated, and then the resulting product was filtered through celite. Next, this was filtered through silica and recrystallized to obtain Compound C-302 (3.5 g, yield: 49%).

[0106] [Table 16]

[0107] [Example 17] Synthesis of Compound C-233 [Chemical formula] Compound 17-1 (5.0 g, 12.2 mmol), Compound 17-2 (3.9 g, 13.4 mmol), Pd(amphos)Cl2 (0.6 g, 0.91 mmol), Aliquat 336 (1.0 g, 2.44 mmol), and Na2CO3 (2.6 g, 24.4 mmol) in a flask were dissolved in 61 mL of toluene and 20 mL of distilled water, and stirred at 130 °C for 5 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated, and then the resulting product was filtered through celite. Next, this was filtered through silica and recrystallized to obtain Compound C-233 (2.7 g, yield: 41%).

[0108] [Table 17]

[0109] [Example 18] Synthesis of Compound C-235 [Chemical formula] Compound 18-1 (13.7 g, 33.4 mmol), compound 18-2 (10.7 g, 36.7 mmol), Pd(amphos)Cl2 (1.6 g, 2.3 mmol), Aliquat 336 (2.7 g, 6.7 mmol), and Na2CO3 (7.1 g, 66.8 mmol) in a flask were dissolved in 167 mL of toluene and 55 mL of distilled water, and stirred at 130 °C for 3 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated, and then the resulting product was filtered through celite. Next, this was filtered through silica and recrystallized to obtain compound C-235 (4.2 g, yield: 23%).

[0110] [Table 18]

[0111] [Example 19] Synthesis of Compound C-299 [Chemical formula] Compound 19-1 (9.1 g, 30.2 mmol), compound 19-2 (5.6 g, 23.3 mmol), Pd(PPh3)4 (1.3 g, 1.2 mmol), and K2CO3 (6.4 g, 46.5 mmol) in a flask were dissolved in 110 mL of toluene, 22 mL of ethanol, and 22 mL of distilled water, and stirred at 100 °C for 3 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated, and then the resulting product was filtered through celite. Next, this was filtered through silica and recrystallized to obtain compound C-299 (9.4 g, yield: 88%).

[0112] [Table 19]

[0113] [Example 20] Synthesis of Compound C-215 [Chemical formula] Compound 20-1 (16.3 g, 42.6 mmol), compound 20-2 (7.5 g, 23.7 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), SPhos (0.93 g, 2.4 mmol), and K2CO3 (6.5 g, 47.3 mmol) in the flask were dissolved in 150 mL of THF and 15 mL of distilled water, and stirred at 65 °C for 15 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated, and then the obtained product was filtered through celite. Next, this was filtered through silica and recrystallized to obtain compound C-215 (8.5 g, yield: 67%).

[0114] [Table 20]

[0115] Hereinafter, for the purpose of understanding the present disclosure in detail, a method for manufacturing an organic electroluminescent device including a compound according to the present disclosure and its device characteristics will be described.

[0116] [Device Examples 1 to 7] Fabrication of an OLED in which a compound according to the present disclosure was vapor-deposited as an N-type charge generation layer material An OLED according to the present disclosure was fabricated. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatic Co., Ltd., Japan) on a glass substrate for the OLED was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, then stored in isopropyl alcohol, and then used. Thereafter, the ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Next, compound HI-1 was introduced into one cell of the vacuum evaporation apparatus, and compound HT-1 was introduced into another cell. The two materials were evaporated at different speeds, and compound HI-1 was deposited at a doping amount of 3 wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 5 nm. Next, compound HT-1 was deposited as a first hole transport layer having a thickness of 30 nm on the hole injection layer. Then, compound HT-2 was introduced into another cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate it, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emission layer was formed thereon as follows: Compound H-1 was introduced into a cell of the vacuum evaporation apparatus as a host, and compound D-1 was introduced into another cell as a dopant. The two materials were evaporated at different speeds, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form a first emission layer having a thickness of 20 nm on the second hole transport layer. Next, compound ET-1 was deposited as a first hole blocking layer material to a thickness of 5 nm on the first emission layer. Thereafter, compound ET-2 was doped to a thickness of 10 nm as an electron transport layer material, thereby forming a first electron transport layer. Then, 0.5 wt% of Li was deposited on the compound in Table 1 below to form an N-type charge generation layer having a thickness of 4 nm. Next, compound HI-1 was doped at 6 wt% based on the total amount of compound HI-1 and HT-1 to form a P-type charge generation layer having a thickness of 10 nm. Thereafter, compound HT-1 was deposited to a thickness of 30 nm to form a third hole transport layer, and then compound HT-2 was deposited to a thickness of 5 nm to form a fourth hole transport layer. Next, a second emission layer was deposited as follows. Compound H-1 was introduced into one cell of the vacuum evaporation apparatus as a host, and compound D-1 was introduced into another cell as a dopant.Two materials were evaporated at different speeds, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form a second light-emitting layer with a thickness of 20 nm on the fourth hole transport layer. A compound ET-1 as a second hole blocking layer material with a thickness of 5 nm was deposited on the second light-emitting layer. Compounds ET-3 and EI-1 as the second electron transport layer materials were respectively placed in two cells in a vacuum evaporation apparatus, and the two materials were deposited with a thickness of 25 nm at a weight ratio of 2:1. Next, Yb was deposited as an electron injection layer with a thickness of 1 nm on the second electron transport layer, and then an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using a further vacuum evaporation apparatus. Thus, an OLED was manufactured. Each compound used for all the materials was -6 Purified by vacuum sublimation with toluene.

[0117] [Device Comparative Example 1] Fabrication of an OLED Containing a Conventional Compound as an N-Type Charge Generation Layer An OLED was manufactured in the same manner as in Device Example 1 above, except that the compound shown in Table 1 below was used as the N-type charge generation layer material.

[0118] For the OLEDs of Device Examples 1 to 7 and Comparative Example 1 manufactured as described above, the driving voltage and power efficiency at a luminance of 1,000 nits, and the time required for the light emission to decrease from 100% to 95% (lifetime: T 95 ) were measured, and the results are shown in Table 1 below.

[0119]

Table 21

[0120] [Device Examples 8 to 13] Fabrication of an OLED with a Compound According to the Present Disclosure Deposited as an N-Type Charge Generation Layer Material An OLED was manufactured in the same manner as in Device Example 1, except that Yb was deposited in an amount of 2 wt% as shown in Table 2 below as the N-type charge generation layer material to form an N-type charge generation layer with a thickness of 8 nm, and the thickness of the P-type charge generation layer was changed to 5 nm.

[0121] [Device Comparative Example 2] Fabrication of an OLED Containing a Conventional Compound as the N-Type Charge Generation Layer An OLED was manufactured in the same manner as in Device Example 8, except that the compound shown in Table 2 below was used as the N-type charge generation layer material.

[0122] For the OLEDs of Device Examples 8 to 13 and Device Comparative Example 2 manufactured as described above, the driving voltage and power efficiency at a luminance of 1,000 nits, and the time required for the light emission to decrease from 100% to 95% at a luminance of 1,000 nits (lifetime: T 95 ) were measured, and the results are shown in Table 2 below.

[0123]

Table 22

[0124] From the results of Table 1 and Table 2 above, it can be confirmed that the organic electroluminescent device containing the compound of the present disclosure in the N-type charge generation layer exhibits low driving voltage and / or high power efficiency and / or significantly improved long lifetime characteristics.

[0125] The compounds used in the device examples and comparative examples are shown in Table 3 below.

[0126]

Table 23

[0127]

Table 24

[0128]

Table 25

[0129] [Device Examples 14 to 21] Fabrication of an OLED in which the Compound According to the Present Disclosure is Deposited as the N-Type Charge Generation Layer The thickness of the first electron transport layer was changed to 12 nm, and Yb was vapor-deposited with the N-type charge generation layer material of the compound shown in Table 4 below at 2 wt% to form an N-type charge generation layer with a thickness of 9 nm. An OLED was manufactured in the same manner as in Device Example 1 except that the thickness of the P-type charge generation layer was changed to 6 nm.

[0130] [Device Comparative Example 3] Fabrication of an OLED Containing a Conventional Compound as the N-Type Charge Generation Layer An OLED was manufactured in the same manner as in Device Example 14 above, except that the compound shown in Table 4 below was used as the N-type charge generation layer material.

[0131] The driving voltage, power efficiency, and progressive driving voltage change (ΔV) at a luminance of 1,000 nits of the OLEDs according to Device Examples 14 to 21 and Device Comparative Example 3 manufactured as described above were measured, and the results are shown in Table 4 below.

[0132]

Table 26

[0133] From the results in Table 4 above, it can be confirmed that the organic electroluminescent device containing the compound of the present disclosure in the N-type charge generation layer exhibits a low driving voltage, and / or a high power efficiency, and / or a low driving voltage change.

[0134] The compounds used in the device examples and device comparative examples are shown in Table 5 below.

[0135]

Table 27

[0136]

Table 28

Claims

1. The following formula 1: 【Chemistry 1】 (In the formula, R １ is hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C １ ~C ３０ ) alkyl, or substituted or unsubstituted (3-30 membered) heteroaryl; R ２ ~R ８ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl, substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) a substituted or unsubstituted fused ring with an aromatic ring, or -L-AHr, or may be linked to adjacent substituents to form a ring; However, R ２ ~R ８ at least one of is -L-HAr; L is a single bond, a substituted or unsubstituted (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom; However, R ４ Or R ５ is -L-HAr, compounds in which HAr is quinazoline are excluded. A compound represented by the formula:

2. The substituted alkyl, the substituted alkenyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) The substituted condensed rings with the aromatic ring are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C １ ~C ３０ ) alkyl, halo (C １ ~C ３０ ) alkyl, (C ２ ~C ３０ ) alkenyl, (C ２ ~C ３０ ) alkynyl, (C １ ~C ３０ ) alkoxy, (C １ ~C ３０ ) alkylthio, (C ３ ~C ３０ ) cycloalkyl, (C ３ ~C ３０ ) cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C ６ ~C ３０ ) aryloxy, (C ６ ~C ３０ ) arylthio, unsubstituted or (C ６ ~C ３０ ) aryl-substituted (5-30 membered) heteroaryl, unsubstituted or (5-30 membered) heteroaryl-substituted (C ６ ~C ３０ ) aryl, tri(C １ ~C ３０ ) alkylsilyl, tri(C ６ ~C ３０ ) arylsilyl, di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) fused ring with an aromatic ring, amino, mono- or di(C １ ~C ３０ ) alkylamino, mono- or di(C ６ ~C ３０ ) arylamino, (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylamino, mono- or di(3- to 30-membered)heteroarylamino, (C １ ~C ３０ ) alkyl(3-30 membered)heteroarylamino, (C ６ ~C ３０ ) aryl(3-30 membered)heteroarylamino, (C １ ~C ３０ ) alkylcarbonyl, (C １ ~C ３０ ) alkoxycarbonyl, (C ６ ~C ３０ ) arylcarbonyl, (C ６ ~C ３０ ) arylphosphinyl, di(C ６ ~C ３０ ) arylboronyl, di(C １ ~C ３０ ) alkylboronyl, (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylboronyl, (C ６ ~C ３０ ) Al (C １ ~C ３０ ) alkyl, and (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) aryl.

3. Formula 1 is the following formulas 1-1 to 1-7: 【Chemistry 2】 (In the formula, R １ , L and HAr are as defined in claim 1; R ２ ~R ８ are each independently hydrogen, deuterium, substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; The compound according to claim 1, wherein the compound is represented by any one of the following formulas:

4. HAr is represented by formula 1-a or 1-b: 【Chemistry 3】 (In the formula, 【Chemistry 4】 represents the site of attachment to L; X １ and X ２ are each independently N or CR １２ represents; Y １ ~Y ３ are each independently N or NR １４ represents; R １１ and R １２ are each independently hydrogen, substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; R １３ and R １４ are each independently hydrogen, deuterium, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or a moiety directly linked to L; a represents an integer of 1 to 4, and when a is an integer of 2 or more, R １３ may be the same or different from each other) 2. The compound of claim 1, represented by:

5. The compound of formula 1 is the compound: 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 (Wherein, in the above compound, D ｎ means that n hydrogens are replaced with deuterium, where n is an integer equal to or greater than 1, and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

2. The compound of claim 1 , selected from:

6. 13. An organic electroluminescent material comprising a compound represented by formula 1 according to claim 1.

7. 10. An organic electroluminescent device comprising: a plurality of light-emitting units disposed between a first electrode and a second electrode; and at least one charge-generating layer disposed between adjacent light-emitting units, wherein the charge-generating layer comprises a compound represented by formula 1 according to claim 1.

8. 8. The organic electroluminescent device of claim 7, wherein at least one of the plurality of light-emitting units comprises a first light-emitting layer and a second light-emitting layer adjacent to each other.

9. The following compound: 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 A compound selected from:

10. An organic electroluminescent material comprising the compound according to claim 9.

11. 10. An organic electroluminescent device comprising a plurality of light-emitting units disposed between a first electrode and a second electrode, and at least one charge generating layer disposed between adjacent light-emitting units, the charge generating layer comprising the compound of claim 9.

12. 12. The organic electroluminescent device of claim 11, wherein at least one of the plurality of light-emitting units comprises a first light-emitting layer and a second light-emitting layer adjacent to each other.

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