CN113316627A

CN113316627A - Organic electroluminescent compounds and organic electroluminescent device comprising the same

Info

Publication number: CN113316627A
Application number: CN202080010139.8A
Authority: CN
Inventors: 文斗铉; 李琇炫; 朴头龙; 赵相熙; 李东炯
Original assignee: Rohm and Haas Electronic Materials Korea Ltd
Current assignee: Rohm and Haas Electronic Materials Korea Ltd
Priority date: 2019-01-25
Filing date: 2020-01-22
Publication date: 2021-08-27
Also published as: KR102682980B1; KR102687418B1; KR20210107600A; KR20220002192A; KR102302838B1; KR20210107602A; KR20240068612A; KR20200092879A; KR20210111200A

Abstract

The present disclosure relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the same. By including the organic electroluminescent compounds of the present disclosure, an organic electroluminescent device having characteristics of a long life and/or a high luminous efficiency can be provided.

Description

Organic electroluminescent compounds and organic electroluminescent device comprising the same

Technical Field

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

Background

An electroluminescent device (EL device) is a self-luminous display device, which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic electroluminescent device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming a light emitting layer (see appl. phys. lett. [ appphysics promt ]51, 913, 1987).

An organic electroluminescent device (OLED) converts electrical energy into light by applying power to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the OLED may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., if necessary. Materials used in the organic layer may be classified into a hole injection material, a hole transport material, a hole assist material, a light emission assist 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, an electron transport material, an electron injection material, and the like according to their functions. In the OLED, holes from an anode and electrons from a cathode are injected into a light emitting layer by applying a voltage, and excitons having high energy are generated by recombination of the holes and the electrons. The organic light emitting compound moves to an excited state by energy and emits light by the energy when the organic light emitting compound returns to a ground state from the excited state.

The most important factor determining the luminous efficiency in OLEDs is the light-emitting material. The luminescent material is required to have the following characteristics: high quantum efficiency, high electron and hole mobility, and uniformity and stability of the formed light emitting material layer. The light emitting materials are classified into blue, green and red light emitting materials according to emission colors, and further include yellow or orange light emitting materials. In addition, in terms of functions, the light emitting material is classified into a host material and a dopant material. Recently, it has been an urgent task to develop an OLED having high efficiency and long life. In particular, in consideration of EL characteristics required for medium-and large-sized OLED panels, development of highly excellent light emitting materials superior to conventional materials is urgently required.

Meanwhile, korean patent application laid-open nos. 2017 and 0096769 and 1814875 disclose heterocyclic compounds and organic electroluminescent devices comprising the same. However, there is still a need to develop a method for improving the performance of OLEDs.

Disclosure of Invention

Technical problem

An object of the present disclosure is to provide an organic electroluminescent compound which is effective for producing an organic electroluminescent device having characteristics of a long life and/or a high luminous efficiency.

Solution to the problem

The present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 1:

wherein,

x represents O or S;

R₁to R₄Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; or may be linked to one or more adjacent substituents to form one or more rings; and is

Radical R₅And R₆Group R₆And R₇And a group R₇And R₈Is fused with the following formula 2 to form one or more rings:

wherein,

R₅to R₈Does not form a ring, each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

R₉to R₁₂Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or-L-ETU; provided that R is₉To R₁₂At least one of them represents a-L-ETU;

l represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene; and is

ETU represents a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted dibenzoquinazolinyl group, a substituted or unsubstituted benzofuropyrazinyl group, a substituted or unsubstituted benzothienopyrazinyl group, a substituted or unsubstituted benzofuropyrimidinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group.

The invention has the advantages of

The organic electroluminescent compounds according to the present disclosure may provide organic electroluminescent devices having characteristics of long life and/or high luminous efficiency.

Detailed Description

Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure and is not meant to limit the scope of the disclosure in any way.

The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.

The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may include at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, or the like.

Herein, the term "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. The term "(C2-C30) alkenyl" means a straight or branched chain alkenyl group having 2 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. The term "(C2-C30) alkynyl" means a straight or branched chain alkynyl group having 2 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. The term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The term "(3-to 7-membered) heterocycloalkyl" refers to a cycloalkyl group having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms, and includes at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, and preferably O, S and N. The above-mentioned heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. The term "(C6-C30) (arylene) means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, preferably 6 to 25 ring backbone carbon atoms, and more preferably 6 to 18 ring backbone carbon atoms. The above aryl or arylene groups may be partially saturated and may include a spiro structure. The above aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthonaphthyl, fluoranthenyl, spirobifluorenyl, azulenyl and the like. More specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthonaphthyl, pyrenyl, 1-thienyl, 2-thienyl, 3-thienyl, 4-thienyl, 5-thienyl, 6-thienyl, benzo [ c ] phenanthryl, benzo [ g ] thienyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, etc, 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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, 9, 9-dimethyl-1-fluorenyl group, 9-dimethyl-2-fluorenyl group, 9-dimethyl-3-fluorenyl group, 9-dimethyl-4-fluorenyl group, 9-diphenyl-1-fluorenyl group, 9-diphenyl-2-fluorenyl group, 9-diphenyl-3-fluorenyl group, 9-diphenyl-4-fluorenyl group and the like.

The term "(3-to 30-membered) hetero (arylene) group" is an (arylene) group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above-mentioned hetero (arylene) group may be a single ring, or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a (arylene) heteroaryl group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may comprise a spiro structure. The above heteroaryl group may include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like; and fused-ring type heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinidinyl, cinnazinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolanyl, dihydroacridinyl and the like. More specifically, the heteroaryl group may include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 6-pyrimidinyl group, a 1, 2, 3-triazin-4-yl group, a 1, 2, 4-triazin-3-yl group, a 1, 3, 5-triazin-2-yl group, a 1-imidazolyl group, a 2-imidazolyl group, a 1-pyrazolyl group, a 1-indolinyl group, a 2-indolinyl group, a 3-indolinyl group, a 5-indolinyl group, a 6-indolinyl group, a 7-indolinyl group, an 8-indolinyl group, a 2-imidazopyridinyl group, a 3-imidazopyridinyl group, a 5-imidazopyridinyl group, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 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-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalyl group, 5-quinoxalyl group, 6-quinoxalyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazolyl-1-yl group, azacarbazolyl-2-yl group, azacarbazolyl group, 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-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-tert-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-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, 4-germanium fluorenyl, and the like. "halogen" includes F, Cl, Br, and I.

Further, "ortho (o-)", "meta (m-)" and "para (p-)" are prefixes, and respectively indicate the relative positions of substituents. The ortho position means that two substituents are adjacent to each other, and for example when two substituents in a benzene derivative occupy positions 1 and 2, it is referred to as ortho position. Meta indicates that the two substituents are at positions 1 and 3, and is referred to as meta, for example, when the two substituents in the benzene derivative occupy positions 1 and 3. Para represents the two substituents at positions 1 and 4, and is referred to as para, for example, when the two substituents in the benzene derivative occupy positions 1 and 4.

In this context, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or another functional group (i.e., substituent). In the present disclosure, the substituents of the substituted alkyl, substituted (arylene), substituted heteroaryl, substituted silyl, substituted amino, substituted pyrimidinyl, substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted dibenzoquinazolinyl, substituted benzofuropyrazinyl, substituted benzothienopyrazinyl, substituted benzofuropyrimidinyl, and substituted benzothienopyrimidinyl are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (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-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl unsubstituted or substituted with one or more (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with one or more (3-to 30-membered) heteroaryl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino unsubstituted or substituted with one or more (C1-C30) alkyl groups; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, each substituent is independently at least one selected from the group consisting of: (C1-C20) alkyl; (C6-C25) aryl; (5-to 25-membered) heteroaryl unsubstituted or substituted with one or more (C6-C25) aryl; and (C1-C10) alkyl (C6-C25) aryl. According to another embodiment of the present disclosure, each of the substituents is independently at least one selected from the group consisting of: (C1-C10) alkyl; (C6-C25) aryl; (5-to 20-membered) heteroaryl unsubstituted or substituted with one or more (C6-C18) aryl; and (C1-C5) alkyl (C6-C25) aryl. For example, each substituent independently may be at least one selected from the group consisting of: methyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl substituted with one or more phenyl groups, dibenzothienyl, dibenzofuranyl, benzonaphthothienyl, and benzonaphthofuranyl.

In the formulae of the present disclosure, a ring formed by the connection of adjacent substituents means that at least two adjacent substituents are connected to each other or fused to form a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof; and preferably, a substituted or unsubstituted, mono-or polycyclic (3-to 26-membered), alicyclic or aromatic ring, or a combination thereof. Furthermore, the ring may contain at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. For example, the ring may be 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 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, a substituted or unsubstituted carbazole ring, or the like.

Herein, heteroaryl (ene) and heterocycloalkyl each independently may contain at least one heteroatom selected from B, N, O, S, Si and P. Further, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, And substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino.

In formula 1, R₁To R₄Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; or may be linked to one or more adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, R₁To R₄Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group; or a radical R₁And R₂Group R₂And R₃And a group R₃And R₄At least one group of (a) may be linked to each other to form one or more rings. According to another embodiment of the disclosure, R₁To R₄Each independently represents hydrogen, deuterium, unsubstitutedOr a (5-to 25-membered) heteroaryl group unsubstituted or substituted with one or more (C6-C18) aryl groups. For example, R₁To R₄Each independently represents hydrogen, phenyl, naphthyl, biphenyl, phenanthryl, carbazolyl substituted with one or more phenyl groups, dibenzothienyl, or dibenzofuranyl.

In formula 1, the group R₅And R₆Group R₆And R₇And a group R₇And R₈Is fused with the following formula 2 to form one or more rings. According to one embodiment of the disclosure, R5 and R₆Or R₆And R₇Or R₇And R₈Fused with the following formula 2 to form one or more rings.

In formula 1, R₅To R₈Does not form a ring, and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one embodiment of the present disclosure, R₅To R₈Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 20-membered) heteroaryl group. According to another embodiment of the disclosure, R₅To R₈Each independently represents hydrogen, deuterium, or an unsubstituted (C6-C18) aryl group. For example, R₅To R₈Each independently may represent hydrogen, phenyl, naphthyl or biphenyl.

In formula 1, R₉To R₁₂Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or-L-ETU. R₉To R₁₂At least one of them represents an x-L-ETU. According to one embodiment of the present disclosure, R₉To R₁₂Any of which is x-L-ETU. According to another embodiment of the disclosure, R₉To R₁₂Each independently represents hydrogen, deuterium or x-L-ETU; provided that R is₉To R₁₂Any of them represents x-L-ETU.

L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-to 25-membered) heteroarylene. According to another embodiment of the disclosure, L represents a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5-to 20-membered) heteroarylene. For example, L may represent a single bond, phenylene, naphthylene, biphenylene, or pyridylene.

ETU represents a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted dibenzoquinazolinyl group, a substituted or unsubstituted benzofuropyrazinyl group, a substituted or unsubstituted benzothienopyrazinyl group, a substituted or unsubstituted benzofuropyrimidinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group. According to one embodiment of the disclosure, ETU represents a substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted benzofuropyrimidinyl, or substituted benzothienopyrimidinyl group. Each of the substituents of the substituted triazinyl, the substituted quinazolinyl, the substituted quinoxalinyl, the substituted benzoquinoxalinyl, the substituted dibenzoquinoxalinyl, the substituted benzoquinazolinyl, the substituted benzofuropyrimidinyl, and the substituted benzothienopyrimidinyl independently may be at least one selected from the group consisting of: substituted or unsubstituted (C6-C25) aryl and substituted or unsubstituted (5-to 30-membered) heteroaryl, and preferably at least one selected from the group consisting of: phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl substituted with one or more phenyl groups, dibenzothienyl, dibenzofuranyl, benzonaphthothienyl, and benzonaphthofuranyl. For example, the ETU may be represented by any one of the following.

Herein, each R independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one embodiment of the disclosure, each R independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl. According to another embodiment of the disclosure, each R independently represents hydrogen, deuterium, (C6-C25) aryl unsubstituted or substituted with one or more (C1-C10) alkyl groups and/or one or more (C6-C18) aryl groups, or (5-to 30-membered) heteroaryl unsubstituted or substituted with one or more (C6-C18) aryl groups. For example, each R independently may represent hydrogen, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl substituted with one or more phenyl groups, dibenzothienyl, dibenzofuranyl, benzonaphthothienyl, or benzonaphthofuranyl.

The compound represented by formula 1 may be represented by any one of the following formulas 1-1 to 1-3.

In the formulae 1-1 to 1-3, R₅To R₁₂Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; and R is₁To R₄L, ETU and X are as defined above in formula 1. Further, R in the formulae 1-1 to 1-3₁To R₁₂Preferred and specific examples of L, ETU and X are as mentioned in formula 1 above.

The compound represented by formula 1 may be any one selected from the group consisting of the following compounds, but is not limited thereto.

The organic electroluminescent compounds according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, and for example, may be prepared as shown in the following reaction schemes 1 to 4, but are not limited thereto.

[ reaction scheme 1]

[ reaction scheme 2]

[ reaction scheme 3]

[ reaction scheme 4]

In reaction schemes 1 to 4, R₁To R₁₂X, L and ETU are as defined in formula 1, and Hal represents halogen.

Although illustrative synthetic examples of the compound represented by formula 1 are described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling Reaction, N-arylation Reaction, acidified montmorillonite (H-mont) -mediated etherification Reaction, Miyaura boronation Reaction, Suzuki cross-coupling Reaction, intramolecular acid-induced cyclization Reaction, Pd (II) -catalyzed oxidative cyclization Reaction, Grignard Reaction (Grignard Reaction), Heck Reaction (Hereacion), dehydration cyclization Reaction, SN Reaction₁Substitution reaction, SN₂Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like, and the above reaction proceeds even if a substituent defined by the above formula 1 but not specified in the specific synthetic examples is bonded.

The dopant that may be used in combination with the compounds according to the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material is not particularly limited, but may be preferably selected from a metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from an ortho-metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.

The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following formula 101, but is not limited thereto.

In formula 101, L is selected from any one of the following structures 1 to 3:

R₁₀₀to R₁₀₃Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to adjacent one or more R₁₀₀To R₁₀₃To form a substituted or unsubstituted fused ring with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, 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;

R₁₀₄to R₁₀₇Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to adjacent one or more R₁₀₄To R₁₀₇To form a substituted or unsubstituted fused ring with benzene, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;

R₂₀₁to R₂₂₀Each independently represents hydrogen, deuterium, halogen, or an unsubstituted(C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, substituted or substituted with deuterium or halogen; or may be linked to adjacent one or more R₂₀₁To R₂₂₀Form a substituted or unsubstituted fused ring thereon; and is

s represents an integer of 1 to 3.

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

The compound represented by formula 1 of the present disclosure may be included in at least one layer constituting an organic electroluminescent device, and for example, in at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, a light emitting layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each layer may further be composed of a plurality of layers.

In addition, the compound represented by formula 1 of the present disclosure is not limited thereto, but may be included in the light emitting layer and or the electron transport region. The compound represented by formula 1 of the present disclosure may be included in the light emitting layer as a host material, and simultaneously or optionally, may be included in the electron transport region as one or more electron buffer materials and/or one or more electron blocking materials.

The hole transport region of the present disclosure may be comprised of at least one layer selected from the group consisting of: an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and each of the layers may be composed of one or more layers. Preferably, the electron transport region may include an electron buffer layer and/or an electron blocking layer. In addition, the electron transport region may further include at least one of one or more electron transport layers and one or more electron injection layers.

The organic electroluminescent material of the present disclosure, for example, at least one of a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transport material, and an electron injection material, may include the compound represented by formula 1. The organic electroluminescent material may be at least one of a light emitting material, an electron buffering material, and a hole blocking material. The organic electroluminescent material may consist of only the compound represented by formula 1, and may further include one or more conventional materials included in the organic electroluminescent material. When two or more materials are contained in one layer, they may be deposited in a mixture, or may be co-deposited separately to form a layer.

An organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include at least one light emitting layer, and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer.

The first electrode and the second electrode may each be formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be a top emission type, a bottom emission type, or a both-side emission type according to the kind of materials forming the first electrode and the second electrode. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

The organic electroluminescent device of the present disclosure may include the compound represented by formula 1, and may further include one or more conventional materials included in the organic electroluminescent device. The organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 of the present disclosure may exhibit high luminous efficiency and/or long life characteristics.

In addition, the organic electroluminescent material according to one embodiment of the present disclosure may be used as a light emitting material for a white organic light emitting device. According to the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light emitting cells, various structures have been proposed for a white organic light emitting device, such as a parallel arrangement (side-by-side) method, a stack arrangement method, or a Color Conversion Material (CCM) method, etc. The organic electroluminescent compounds according to the present disclosure may also be applied to white organic light emitting devices.

The organic electroluminescent material according to one embodiment of the present disclosure may also be applied to an organic electroluminescent device including QDs (quantum dots).

Further, the present disclosure may provide a display system by using the compound represented by formula 1. Further, a display system or a lighting system can be produced by using the compound of the present disclosure. Specifically, a display system, such as a display system for a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, may be produced by using the organic electroluminescent compounds of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.

Hereinafter, the preparation method of the compound of the present disclosure, and the characteristics of the compound will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

Example 1: preparation of Compound C-160

Synthesis of Compound 1-1

In a reaction vessel, 37g of benzo [ b ] thiophen-2-ylboronic acid (205.05mmol), 30g of 2-bromo-6-chlorobenzaldehyde (136.7mmol), 4.7g of tetrakis (triphenylphosphine) palladium (4.1mmol), 47.2g of potassium carbonate (341.75mmol), 400mL of tetrahydrofuran and 100mL of distilled water were added, and the mixture was stirred at 100 ℃ for 4 hours. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 35g of compound 1-1 (yield: 94%).

Synthesis of Compound 1-2

In a reaction vessel, 35g of Compound 1-1(128.32mmol) and 66g of (methoxymethyl) triphenylphosphonium chloride (192.48mmol) were added to 350mL of tetrahydrofuran, and 193mL of 1M potassium tert-butoxide was added dropwise to the mixture at 0 ℃. After completion of the dropwise addition, the reaction temperature was gradually raised to room temperature, and the mixture was further stirred for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 31g of compound 1-2 (yield: 80%).

Synthesis of Compounds 1-3

In a reaction vessel, 31g of compound 1-2(103.06mmol) was dissolved in chlorobenzene and 3.1mL of Eton's reagent was slowly added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 24.4g of the compounds 1 to 3 (yield: 88%).

Synthesis of Compounds 1-4

In a reaction vessel, 9.0g of the compounds 1 to 3(29.77mmol), 9.1g of bis (pinacolato) diboron (35.72mmol), 1.1g of tris (dibenzylideneacetone) dipalladium (1.19mmol), 1.0g of 2-dicyclohexylphosphino-2 ', 6' -dimethoxybiphenyl (s-phos) (2.38mmol), 8.8g of potassium acetate (89.31mmol) and 150mL of 1, 4-dioxane were added, and the mixture was stirred at 130 ℃ for 6 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 9.0g of the compounds 1 to 4 (yield: 84%).

Synthesis of Compound C-160

In a reaction vessel, 4.5g of the compound 1-4(12.49mmol), 6.6g of 2- (3 '-bromo- [1, 1' -biphenyl ] -3-yl) -4, 6-diphenyl-1, 3, 5-triazine (14.20mmol), 0.4g of tetrakis (triphenylphosphine) palladium (0.34mmol), 3.0g of sodium carbonate (28.38mmol), 55mL of toluene, 14mL of ethanol, and 14mL of distilled water were added, and the mixture was stirred at 120 ℃ for 4 hours. After the reaction was completed, the precipitated solid was washed with distilled water and methanol. The residue was separated by column chromatography to obtain 3.9g of Compound C-160 (yield: 51%). The physical properties of the synthesized compound C-160 are as follows.

	MW	M.P.
			C-160	617.7	268℃

Example 2: preparation of Compound C-5

4.0g of the compound 1-4(11.1mmol) and 4.6g of 2- ([1, 1' -biphenylyl) benzene were added]-4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (13.3mmol), 0.6g Pd (PPh)₃)₄(0.56mmol) and 3.1g of K₂CO₃(22.2mmol) was added to 5.0mL of EtOH, 40mL of toluene, and 11mL of distilled water, and the mixture was stirred at reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and stirred at room temperature. MeOH was added thereto, and the resulting solid was filtered under reduced pressure. The residue was separated by column chromatography using MC/Hex to obtain 4.9g of Compound C-5 (yield: 81%).

	MW	M.P.
			C-5	541.7	280℃

Example 3: preparation of Compound C-146

4.0g of the compound 1-3(14.9mmol), 7.1g of 2, 4-diphenyl-6- (3- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1, 3, 5-triazine (16.4mmol), 0.7g of Pd₂(dba)₃(0.8mmol), 0.6g of s-phos (1.5mmol) and 3.5g of NaOtBu (37.3mmol) were added to 80mL of o-xylene and the mixture was stirred at reflux for 6 h. After completion of the reaction, the reaction mixture was cooled to room temperature and stirred at normal temperature. MeOH was added thereto, and the resulting solid was filtered under reduced pressure. The residue was separated by column chromatography using MC/Hex to obtain 3.6g of Compound C-146 (yield: 45%).

	MW	M.P.
			C-146	541.7	261℃

Example 4: preparation of Compound C-499

In a flask, 5.40g of the compound 4-1(15.7mmol), 5.41g of 2- (6-chloropyridin-3-yl) -4, 6-diphenyl-1, 3, 5-triazine (15.7mmol), 551mg of bis (triphenylphosphine) palladium (II) dichloride (0.78mmol) and 2.5g of sodium carbonate (23.5mmol) were dissolved in 80mL of THF: distilled water (10: 1 mixed solution), and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate. The residue was separated by column chromatography to obtain 3.0g of compound C-499 (yield: 36%).

	MW	M.P.
			C-499	526.6	305℃

Example 5: preparation of Compound C-230

Synthesis of Compound 5-1

In a flask, 30g of 6-chloro-3-iodo-2-methoxynaphthalene (94.19mmol), 13.1g of (2-fluorophenyl) boronic acid (94.19mmol), 5.4g of tetrakis (triphenylphosphine) palladium (4.709mmol) and 39g of potassium carbonate (282.5mmol) were dissolved in 580mL of toluene, 145mL of ethanol and 145mL of water, and the mixture was stirred at reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic layer was extracted with ethyl acetate. The residue was separated by column chromatography to obtain 18.5g of compound 5-1 (yield: 68%).

Synthesis of Compound 5-2

In a flask, 18.5g of compound 5-1(64.52mmol) and 112g of pyridine hydrochloride (967.9mmol) were added, and the mixture was stirred at 230 ℃ for 3 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic layer was extracted with dimethyl chloride. After distillation under reduced pressure, hexane was added dropwise and filtered to obtain 14.8g of compound 5-2 (yield: 84%).

Synthesis of Compound 5-3

In a flask, 14.8g of compound 5-2(54.27mmol), 3.75g of potassium carbonate (27.13mmol), and 360mL of dimethylformamide were added, and the mixture was stirred under reflux for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature and water was added dropwise and filtered to obtain 13g of compound 5-3 (yield: 94%).

Synthesis of Compound 5-4

In a flask, 10g of the compound 5-3(39.57mmol), 12g of bis (pinacolato) diboron (47.48mmol), 1.4g of tris (dibenzylideneacetone) dipalladium (0) (1.582mmol), 1.3g of 2-dicyclohexylphosphino-2 ', 6' -dimethoxybiphenyl (3.165mmol), 11.6g of potassium acetate (118.7mmol) and 200mL of 1, 4-dioxane were added, and the mixture was stirred at reflux for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate. The residue was separated by column chromatography to obtain 7.8g of compound 5-4 (yield: 54%).

Synthesis of Compound C-230

In a flask, 4.5g of the compound 5-4(13.07mmol), 5g of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (13.07mmol), 0.75g of tetrakis (triphenylphosphine) palladium (0.653mmol), 5.4g of potassium carbonate (39.22mmol), 80mL of toluene, 20mL of ethanol, and 20mL of water were added, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and methanol was added dropwise and filtered. The residue was dissolved in dimethyl chloride and separated by column chromatography to obtain 3.7g of compound C-230 (yield: 53%).

	MW	M.P.
			C-230	525.6	272℃

Meanwhile, the present inventors have found the following fact by comparing the following compound of type B according to the present disclosure with the following compound of type a not according to the present disclosure.

Devices comprising a type B compound as a red host material may have improved lifetime characteristics compared to devices comprising a type a compound as a red host material. Without intending to be limited by theory, compounds of type B have longer conjugation and lower steric energy than compounds of type a, wherein compounds with long conjugation can stabilize electrons. It is believed that this is because compounds having low steric hindrance are difficult to decompose at high temperatures.

Hereinafter, characteristics of an organic electroluminescent device (OLED) including the compound according to the present disclosure will be explained in detail. However, the following examples only illustrate the characteristics of the OLED according to the present disclosure in detail, but the present disclosure is not limited to the following examples.

Apparatus examples 1 and 2: production of OLEDs using compounds according to the present disclosure

Production comprising conversion according to the present disclosureOLED of compound (i): a transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) (geomaoma co., ltd., Japan) on a glass substrate for an OLED was sequentially ultrasonically washed with acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Introducing the compound HI-1 into a chamber of a vacuum vapor deposition apparatus, and then controlling the pressure in the chamber of the apparatus to 10^-6And (4) supporting. Thereafter, a current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80nm on the ITO substrate. Next, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. Then, the compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a first hole transport layer having a thickness of 10nm on the second hole injection layer. Then, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the compound shown as the main body in table 1 below was introduced as the main body into one cell of the vacuum vapor deposition apparatus, and the compound D-71 was introduced as a dopant into the other cell. The two materials were evaporated at different rates and deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 40nm on the second hole transporting layer. The compound ET-1 and the compound EI-1 were then introduced into two additional cells, evaporated at a rate of 1: 1, and deposited to form an electron transport layer having a thickness of 35nm on the light-emitting layer. After depositing the compound EI-1 on the electron transport layer as an electron injection layer having a thickness of 2nm, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED device was produced.

Example apparatus 3: production of OLEDs using compounds according to the present disclosure

An OLED device was produced in the same manner as device example 1, except that the first hole injection layer was deposited to a thickness of 60nm, the first hole transport layer was deposited to a thickness of 20nm, and compound HT-3 was used instead of compound HT-2 to form a second hole transport layer having a thickness of 5 nm: the compound BH was introduced as a host into one cell of a vacuum vapor deposition apparatus, and the compound BD was introduced as a dopant into the other cell. The two materials were evaporated at different rates and deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 20nm on the second hole transporting layer. Next, compound C-160 was deposited on the light emitting layer to form an electron buffer layer (or hole blocking layer) having a thickness of 5 nm. Compound ET-1 and compound EI-1 were then introduced into two additional chambers at a rate of 1: 1, and is deposited to form an electron transport layer having a thickness of 30nm on the electron buffer layer (or hole blocking layer).

Comparative example 1: production of OLEDs using compounds not according to the present disclosure

An OLED device was produced in the same manner as in device example 1, except that compound a was used as a host of the light emitting layer.

Comparative example 2: production of OLEDs using compounds not according to the present disclosure

An OLED device was produced in the same manner as in device example 1, except that compound B was used as a host of the light emitting layer.

Comparative example 3: production of OLEDs using compounds not according to the present disclosure

Except that no electron buffer layer (or hole blocking layer) was deposited and the thickness of the layer was measured at 1: an OLED device was produced in the same manner as device example 3, except that compound ET-1 and compound EI-1 were evaporated at a rate of 1 and deposited to form an electron transport layer having a thickness of 35nm on the light emitting layer.

The driving voltage and CIE color coordinates of the OLEDs produced in device examples 1 and 2 and comparative examples 1 and 2 at a luminance of 1,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 5,000 nits (lifetime; T95) are provided in table 1 below.

[ watch 1]

From table 1, it can be determined that the OLED including the compound according to the present disclosure as a host has longer life characteristics than the OLED including the compound not according to the present disclosure as a host.

The driving voltage, the light emitting efficiency, and the CIE color coordinates of the OLEDs produced in device example 3 and comparative example 3 at a luminance of 1,000 nits are provided in table 2 below.

[ Table 2]

From table 2, it can be determined that the OLED including the compound according to the present disclosure in the electron buffer layer (or the hole blocking layer) has higher luminous efficiency characteristics than the OLED not according to the present disclosure.

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

[ Table 3]

Claims

1. An organic electroluminescent compound represented by the following formula 1:

wherein,

x represents O or S;

wherein,

2. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted alkyl group, the substituted (arylene) heteroaryl group, the substituted silyl group, the substituted amino group, the substituted triazinyl group, the substituted quinazolinyl group, the substituted quinoxalinyl group, the substituted benzoquinoxalinyl group, the substituted dibenzoquinoxalinyl group, the substituted benzoquinazolinyl group, the substituted dibenzoquinazolinyl group, the substituted benzofuropyrazinyl group, the substituted benzothienopyrazinyl group, the substituted benzofuropyrimidinyl group, and the substituted benzothienopyrimidinyl group are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (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-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl unsubstituted or substituted with one or more (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with one or more (3-to 30-membered) heteroaryl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino unsubstituted or substituted with one or more (C1-C30) alkyl groups; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.

3. The organic electroluminescent compound according to claim 1, wherein the formula 1 is represented by any one of the following formulae 1-1 to 1-3:

wherein,

R₅to R₁₂Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; and is

R₁To R₄L, ETU and X are as defined in claim 1.

4. The organic electroluminescent compound according to claim 1, wherein ETU is represented by any one of:

wherein,

each R independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted silyl, or substituted or unsubstituted amino.

5. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is any one selected from the group consisting of:

6. an organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.

7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

8. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent compound is contained in at least one of a light emitting layer and an electron transport region.