Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved driving voltage, lifespan characteristics, and / or power efficiency can be provided.

Description

Technical Field

[0001] This disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Technology

[0002] Small-molecule green organic electroluminescent devices (OLEDs) were first developed in 1987 by Tang et al. at Eastman Kodak using a TPD / ALq3 bilayer consisting of a light-emitting layer and a charge-transport layer. Since then, OLED development has been rapidly influenced, and OLEDs have been commercialized. Currently, OLEDs primarily use phosphorescent materials with excellent luminous efficiency in panel implementation. Long-term use and high resolution of displays require low driving voltage and high luminous efficiency.

[0003] Various materials or concepts for organic layers in organic electroluminescent devices have been proposed to enhance luminous efficiency, driving voltage, and / or lifetime characteristics. However, they have not been satisfactory in practical applications. Summary of the Invention

[0004] Technical issues

[0005] The purpose of this disclosure is to provide an organic electroluminescent compound that is effective in producing organic electroluminescent devices with improved drive voltage, lifetime characteristics, and / or power efficiency. Another purpose of this disclosure is to provide an organic electroluminescent device comprising the said organic electroluminescent compound.

[0006] Solution to the problem

[0007] The inventors of this invention have discovered that the above-mentioned objective can be achieved by an organic electroluminescent compound represented by the following formula 1:

[0008]

[0009] in

[0010] L1 and L2 independently represent single-bonded, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;

[0011] Ar1 represents substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl;

[0012] Ar2 represents the following formula 1-1 or 1-2;

[0013]

[0014]

[0015] R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-membered to 30-membered) heteroaryl.

[0016] R3 to R9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-membered to 30-membered) heteroaryl, or may be connected to L2.

[0017] X represents O, S, or NR. 11 ;

[0018] R 11 This indicates a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group, or may be linked to L2; and

[0019] a, b, d, h, and i each independently represent integers from 1 to 4, c represents integers from 1 to 5, e and f each independently represent integers from 1 to 3, and g represents integers from 1 to 2. If a to i are integers of 2 or greater, then each R1 to each R9 can be the same or different.

[0020] Additionally, this disclosure provides an organic electroluminescent device comprising a first electrode; a second electrode; and a plurality of organic layers, the organic layers including a light-emitting layer between the first electrode and the second electrode, wherein at least two of the organic layers comprise one or more compounds represented by formulas 3-1 and 3-2:

[0021]

[0022]

[0023] in

[0024] R3' to R9' independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3- to 60-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, one or more substituted or unsubstituted (C3-C30) aliphatic rings and one or more substituted or unsubstituted (C6-C30) aromatic rings, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkoxy, substituted or unsubstituted (C1-C30) aryloxy, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, and substituted or unsubstituted mono- or di-(C1-C30) alkylamino. 2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino, or may be connected with adjacent substituents to form one or more rings;

[0025] X' represents O, S, or NR 11 ';

[0026] R 11 'Indicates -L 11 -Ar3;

[0027] L 11 Indicates a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-arylene) heteroarylene;

[0028] Ar3 represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted mono- or di- (C6-C60) arylamino, substituted or unsubstituted mono- or di- (3- to 60-membered) heteroarylamino, or substituted or unsubstituted (C6-C60) aryl (3- to 60-membered) heteroarylamino; and

[0029] c' represents an integer from 1 to 5, d', h', and i' each independently represent an integer from 1 to 4, e' and f' each independently represent an integer from 1 to 3, and g' represents an integer from 1 to 2. If c' to i' are integers of 2 or greater, then each R3' to each R9' can be the same or different.

[0030] Beneficial effects of the present invention

[0031] By using the organic electroluminescent compounds disclosed herein, organic electroluminescent devices with improved driving voltage, lifetime characteristics, and / or power efficiency can be produced. Detailed Implementation

[0032] This disclosure will be described in detail below. However, the following description is intended to explain this disclosure and is not intended to limit the scope of this disclosure in any way.

[0033] The term "organic electroluminescent compound" in this disclosure refers to a compound that can be used in an organic electroluminescent device. If necessary, the organic electroluminescent compound may be included in any layer constituting the organic electroluminescent device.

[0034] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If necessary, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting 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 transport assist material, an electron injection material, etc.

[0035] The organic electroluminescent material disclosed herein may comprise at least one compound represented by Formula 1. The compound represented by Formula 1 may be included in a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (including a host and a dopant), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, preferably in the light-emitting layer, the electron transport layer, and / or the electron transport auxiliary layer, but is not limited thereto. When included in the light-emitting layer, the compound represented by Formula 1 may be included as a host material or a dopant material, wherein the host material may be a host material for a blue, green, or red light-emitting organic electroluminescent device. Furthermore, when included in the electron transport layer, the compound represented by Formula 1 may be included as an electron transport material. Additionally, when included in the electron transport auxiliary layer, the compound represented by Formula 1 may be included as an electron transport auxiliary material.

[0036] In this document, the term "(C1-C30)alkyl" refers to a straight-chain or branched 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 aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term "(C2-C30)alkenyl" refers to a straight-chain or branched alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term "(C2-C30)ynyl" refers to a straight-chain or branched ynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned alkynyl groups may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpentan-2-ynyl, etc. The term "(C3-C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in its cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered) heterocyclic alkyl" refers to a cycloalkyl group having 3 to 7, preferably 5 to 7, cyclic skeleton atoms and containing at least one heteroatom, wherein the heteroatom is selected from the group consisting of B, N, O, S, Si, and P, and preferably from the group consisting of O, S, and N. The aforementioned heterocyclic alkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The term "(C6-C30)(aryl)-aryl" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 25, and more preferably 6 to 18. The aforementioned (aryl)-aryl group may be partially saturated and may contain a spirostructure. The aforementioned aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, phenylphenanthryl, anthracene, indene, triphenylene, pyrene, tetraphenyl, perylene, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, azuleyl, etc. More specifically, the above-mentioned aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzanthyl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, naphthyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Triphenylene, 2-Triphenylene, 3-Triphenylene, 4-Triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzo[a]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-triphenyl, m-triphenyl-4-yl, m-triphenyl-3-yl, m-triphenyl-2-yl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-tetraphenyl, 3-fluoranthyl, 4-fluoranthyl, 8-fluoranthyl, 9-fluoranthyl, benzo[a]fluoranthyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl 4'-methylbiphenyl, 4'-tert-butyl-p-triphenyl-4'-yl, 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, 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-benzene [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 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 1,1-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, 1 1,11-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, etc.

[0037] The term "(3- to 30-)heteroaryl or (3- to 60-)heteroaryl" refers to an aryl group having 3 to 30 or 3 to 60 ring skeleton atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The aforementioned heteroaryl group may be a monocyclic ring or a fused ring condensed with at least one benzene ring; it may be partially saturated; it may be a (hypo)heteroaryl group formed by linking at least one heteroaryl group or an aryl group to a heteroaryl group via one or more single bonds; and it may contain a spirostructure. The aforementioned heteroaryl groups can include monocyclic heteroaryl groups, such as furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; and fused-ring heteroaryl groups, such as benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, and naphthalene. Benzothiophene, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxoxazolyl, isoindolyl, indolyl, benzoindolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, naphridinyl, carbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzodioxacyclopentenyl, and dihydroacridinyl. More specifically, the aforementioned heteroaryl groups may include 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, pyrazinyl, 2-pyridyl, 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, and 1-indoline. 2-Indolinyl, 3-Indolinyl, 5-Indolinyl, 6-Indolinyl, 7-Indolinyl, 8-Indolinyl, 2-Imidazolopyridyl, 3-Imidazolopyridyl, 5-Imidazolopyridyl, 6-Imidazolopyridyl, 7-Imidazolopyridyl, 8-Imidazolopyridyl, 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-Furanyl, 3-Furanyl, 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-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl6-Isoquinolinyl, 7-Isoquinolinyl, 8-Isoquinolinyl, 2-Quinoxolinyl, 5-Quinoxolinyl, 6-Quinoxolinyl, 1-Carbazoleyl, 2-Carbazoleyl, 3-Carbazoleyl, 4-Carbazoleyl, 9-Carbazoleyl, Azacarbazole-1-yl, Azacarbazole-2-yl, Azacarbazole-3-yl, Azacarbazole-4-yl, Azacarbazole-5- ...2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2-yl, Azacarbazole-2 Carbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridyl, 2-phenanthridyl, 3-phenanthridyl, 4-phenanthridyl, 6-phenanthridyl, 7-phenanthridyl, 8-phenanthridyl, 9-phenanthridyl, 10-phenanthridyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 2- Oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrolo-1-yl, 2-methylpyrrolo-3-yl, 2-methylpyrrolo-4-yl, 2-methylpyrrolo-5-yl, 3-methylpyrrolo-1-yl, 3-methylpyrrolo-2-yl, 3-methylpyrrolo-4-yl, 3-methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-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-Naphtho-[1,2-b]-benzofuranyl, 2-Naphtho-[1,2-b]-benzofuranyl, 3-Naphtho-[1 [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 [-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]-benzothiophene, 2-Naphtho- [1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene, 4-naphtho-[1,2-b]-benzothiophene, 5-naphtho-[1,2-b]-benzothiophene, 6-naphtho-[1,2-b]-benzothiophene, 7-naphtho-[1,2-b]-benzothiophene, 8-naphtho-[1,2-b]-benzothiophene, 9-naphtho-[1,2-b]-benzothiophene, 10-naphtho-[1,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene ]-Benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene The list includes 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, etc. Furthermore, "halogens" include F, Cl, Br, and I.

[0038] Additionally, "ortho (o-)," "meta (m-)," and "para (p-)" are prefixes that indicate the relative positions of the substituents, respectively. Ortho indicates that the two substituents are adjacent to each other, and for example, when the two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta indicates that the two substituents are at positions 1 and 3, and for example, when the two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para indicates that the two substituents are at positions 1 and 4, and for example, when the two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0039] In this document, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). The substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted aliphatic ring, substituted aromatic ring, substituted alkenyl, substituted alkoxy, substituted aryloxy, substituted mono- or dialkylamino, substituted mono- or di-enylamino, substituted mono- or di-arylamino, substituted mono- or di-heteroarylamino, substituted alkylenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, and substituted arylheteroarylamino substituents are each independently selected from at least one of the following groups: deuterium Halogen; cyano; carboxyl; nitro; hydroxyl; (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)heterocyclic alkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl groups; unsubstituted or (C6-C30)aryl substituted with at least one of (C1-C30)alkyl and (3- to 30-membered)heteroaryl groups; tri (C1-C30)alkylsilyl; tris(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C 2-C30) alkenyl(C6-C30) arylamino; (C2-C30) alkenyl(3- to 30-membered) heteroarylamino; (C6-C30) aryl(3- to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylboroncarbonyl; di(C1-C30) alkylboroncarbonyl; (C1-C30) alkyl(C6-C30) arylboroncarbonyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl, wherein the substituents may be replaced by deuterium instead of hydrogen at optional positions.According to one embodiment of this disclosure, each substituent is independently selected from at least one group consisting of (C1-C6)alkyl and (C6-C25)aryl groups. Specifically, each substituent may be independently selected from at least one group consisting of methyl and naphthyl groups.

[0040] In the formulas of this disclosure, if a substituent is connected to an adjacent substituent to form a ring, the ring may be a substituted or unsubstituted, monocyclic or polycyclic (3-membered to 30-membered) aliphatic or aromatic ring, or a combination thereof, wherein the two or more adjacent substituents are connected to form the ring. Furthermore, the formed 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. According to one embodiment of this disclosure, the number of ring skeleton atoms is 5 to 20. According to another embodiment of this disclosure, the number of ring skeleton atoms is 5 to 15.

[0041] In the formula disclosed herein, each (hetero)aryl group may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be bonded to at least one of the following groups: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-membered 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)alkylbis(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.

[0042] The compounds represented by Formula 1 will be described in more detail below.

[0043] According to one embodiment of this disclosure, the compound represented by Formula 1 can be represented by any one of Formulas 2-1 to 2-9:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] in

[0054] Ar1, R1 to R9, L1, L2, X, and a to i are defined as in Equation 1.

[0055] In Formula 1, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-membered to 30-membered) heteroarylene. According to one embodiment of this disclosure, L1 and L2 each independently represent a single bond, or a substituted or unsubstituted (C6-C15) arylene. According to another embodiment of this disclosure, L1 and L2 each independently represent a single bond or an unsubstituted (C6-C15) arylene. Specifically, L1 and L2 may each independently represent a single bond, a phenylene group, etc.

[0056] In Formula 1, Ar1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group. According to one embodiment of this disclosure, Ar1 represents a substituted or unsubstituted (C6-C12) aryl group. According to another embodiment of this disclosure, Ar1 represents an unsubstituted (C6-C12) aryl group. Specifically, Ar1 can represent phenyl, naphthyl, etc.

[0057] In Formula 1, R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-membered to 30-membered) heteroaryl. According to one embodiment of this disclosure, R1 and R2 each independently represent hydrogen.

[0058] In Formulas 1-1 and 1-2, R3 to R9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-membered to 30-membered) heteroaryl, or may be connected to L2. According to one embodiment of this disclosure, R3 to R9 each independently represent hydrogen or may be connected to L2.

[0059] In equations 1-1 and 1-2, X represents O, S, or NR. 11 .

[0060] In this article, R 11 It indicates a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5- to 30-membered) heteroaryl, or may be linked with L2.

[0061] In Equations 1, 1-1, and 1-2, a, b, d, h, and i each independently represent integers from 1 to 4, c represents integers from 1 to 5, e and f each independently represent integers from 1 to 3, and g represents integers from 1 to 2, wherein if a to i are integers of 2 or greater, each R1 to each R9 may be the same or different.

[0062] The compound represented by Formula 1 may be selected from, but is not limited to, the following compounds.

[0063]

[0064]

[0065] The compounds represented by Formula 1 of this disclosure can be produced by synthetic methods known to those skilled in the art, and, for example, according to reaction schemes 1 to 4 below, but are not limited thereto:

[0066] [Reaction Scheme 1]

[0067]

[0068] [Reaction Scheme 2]

[0069]

[0070] [Reaction Scheme 3]

[0071]

[0072] [Reaction Scheme 4]

[0073]

[0074] In reaction schemes 1 to 4, L1, L2, Ar1, R1 to R9, X, and a to i are as defined in Equations 1, 1-1, and 1-2.

[0075] Although illustrative synthetic examples of compounds represented by Formula 1 have been described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II) catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cycloclic dehydration reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that the above reactions are carried out even when substituents defined in Formula 1 above but not specified in the specific synthetic examples are bonded.

[0076] This disclosure provides an organic electroluminescent material comprising a compound represented by Formula 1, and an organic electroluminescent device comprising said organic electroluminescent material. The organic electroluminescent material may consist solely of the compound according to this disclosure, or may further comprise conventional materials included in the organic electroluminescent material.

[0077] If necessary, the organic electroluminescent compound of Formula 1 disclosed herein can be used as a co-host material. That is, the luminescent layer may further comprise an organic electroluminescent compound other than the organic electroluminescent compound of Formula 1 of this disclosure (the first host material) as a second host material. In this case, the weight ratio between the first host material and the second host material is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and more preferably about 30:70 to about 70:30. Moreover, the first host material and the second host material can be combined in the desired ratio by placing them in a vibrator and then mixing them; placing them in a glass tube, dissolving them by heating and then collecting the product; or dissolving them in a solvent, etc. When a layer contains two or more materials, a mixed deposition can be performed to form the layer, or co-deposition can be performed simultaneously and separately to form the layer.

[0078] The dopant included in the organic electroluminescent device of this disclosure is at least one phosphorescent dopant or fluorescent dopant, and preferably a fluorescent dopant. The fluorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited.

[0079] The organic electroluminescent device according to this disclosure may include a first electrode; a second electrode; and a plurality of organic layers, said organic layers including a light-emitting layer between the first electrode and the second electrode. The organic layers may include a light-emitting layer, a light-emitting auxiliary layer between the light-emitting layer and the first electrode, a hole transport layer between the light-emitting auxiliary layer and the first electrode, an electron transport auxiliary layer between the light-emitting layer and the second electrode, and an electron transport layer between the electron transport auxiliary layer and the second electrode. At least two of the organic layers may contain one or more compounds represented by formulas 3-1 and 3-2:

[0080]

[0081]

[0082] in

[0083] R3' to R9' independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3- to 60-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, one or more substituted or unsubstituted (C3-C30) aliphatic rings and one or more substituted or unsubstituted (C6-C30) aromatic rings, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkoxy, substituted or unsubstituted (C1-C30) aryloxy, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, and substituted or unsubstituted mono- or di-(C1-C30) alkylamino. 2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino, or may be connected with adjacent substituents to form one or more rings;

[0084] X' represents O, S, or NR 11 ';

[0085] R 11 'Indicates -L 11 -Ar3;

[0086] L 11 Indicates a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-arylene) heteroarylene;

[0087] Ar3 represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted mono- or di- (C6-C60) arylamino, substituted or unsubstituted mono- or di- (3- to 60-membered) heteroarylamino, or substituted or unsubstituted (C6-C60) aryl (3- to 60-membered) heteroarylamino; and

[0088] c' represents an integer from 1 to 5, d', h', and i' each independently represent an integer from 1 to 4, e' and f' each independently represent an integer from 1 to 3, and g' represents an integer from 1 to 2. If c' to i' are integers of 2 or greater, then each R3' to each R9' can be the same or different.

[0089] According to one embodiment of this disclosure, the compound represented by formula 3-1 or 3-2 may be included in at least the luminescent layer.

[0090] Furthermore, according to one embodiment of this disclosure, the compound represented by formula 3-1 or 3-2 may be contained in at least one of the organic layers between the first electrode and the light-emitting layer. For example, the compound may be contained in one or more of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (including a host and a dopant), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and is preferably contained in one or more of a hole transport layer, an electron transport layer, and an electron transport auxiliary layer, but is not limited thereto.

[0091] According to one embodiment of this disclosure, the compound represented by formula 3-1 or 3-2 may be included, individually or together, in at least two of the following layers of an organic electroluminescent device: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, and a light emission layer (including a host and a dopant); or may be included, individually or together, in at least two of the following layers: a light emission layer (including a host and a dopant), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer.

[0092] The compounds represented by formula 3-1 or 3-2 disclosed herein can be produced by synthetic methods known to those skilled in the art, and by methods disclosed, for example, according to Korean Patent Application Publication Nos. 2018-0099510 (published on September 5, 2018) and 2018-0012709 (published on February 6, 2018), but are not limited thereto.

[0093] As a specific embodiment, a compound having formula 3-1 or 3-2 contained in at least one organic layer is represented by formula 1, and a compound having formula 3-1 or 3-2 contained in at least another organic layer is represented by formula 4.

[0094]

[0095] in

[0096] L1 and L2 independently represent single-bonded, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;

[0097] Ar1 represents substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl;

[0098] Ar2 represents the following formula 1-1 or 1-2;

[0099]

[0100] in

[0101] Ar 21 To Ar 23 At least one of them independently represents either equation 1-1 or 1-2 below, and Ar 21 To Ar 23 The other one or more in the group independently represent substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl;

[0102] L 21 To L 23 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;

[0103]

[0104]

[0105] R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-membered to 30-membered) heteroaryl.

[0106] R3 to R9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-membered to 30-membered) heteroaryl, or may be connected to L2, or may also be connected to L 21To L 23 One or more connections in;

[0107] X represents O, S, or NR. 11 ;

[0108] R 11 This indicates a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group, or may be linked to L2, or may also be linked to L. 21 To L 23 One or more connections in; and

[0109] a, b, d, h, and i each independently represent integers from 1 to 4, c represents integers from 1 to 5, e and f each independently represent integers from 1 to 3, and g represents integers from 1 to 2. If a to i are integers of 2 or greater, then each R1 to each R9 can be the same or different.

[0110] According to one embodiment of this disclosure, in formula 4, Ar 21 To Ar 23 At least one of them is independently represented by expression 1-1 or 1-2, and Ar 21 To Ar 23 The other one or more in the group independently represent substituted or unsubstituted (C6-C20) aryl groups, or substituted or unsubstituted (5-membered to 15-membered) heteroaryl groups. According to another embodiment of this disclosure, Ar 21 To Ar 23 At least one of them is independently represented by expression 1-1 or 1-2, and Ar 21 To Ar 23 The other one or more in the text independently represent unsubstituted or (C6-C20) aryl groups substituted with one or more (C1-C6) alkyl groups and / or one or more (C6-C12) aryl groups, or unsubstituted (5- to 15-membered) heteroaryl groups. Specifically, Ar 21 To Ar 23 At least one of them can be independently expressed as equation 1-1 or 1-2, and Ar 21 To Ar 23 The other one or more in the group can independently represent phenyl, naphthyl, biphenyl, naphthylphenyl, dimethylfluorenyl, dibenzofuranyl, etc.

[0111] According to one embodiment of this disclosure, in formula 4, L 21 To L 23 Each independently represents a single bond, or a substituted or unsubstituted (C6-C15) aryl group. According to another embodiment of this disclosure, L 21 To L23 Each independently represents a single bond or an unsubstituted (C6-C15) aryl group. Specifically, L 21 To L 23 Each can independently represent a single bond, phenylene, biphenylene, etc.

[0112] The compound represented by Formula 4 may be selected from, but is not limited to, the following compounds.

[0113]

[0114]

[0115]

[0116] The compounds represented by Formula 4 of this disclosure can be produced by synthetic methods known to those skilled in the art, and, for example, according to reaction schemes 5 to 8 below, but are not limited thereto:

[0117] [Reaction Scheme 5]

[0118]

[0119] [Reaction Scheme 6]

[0120]

[0121] [Reaction Scheme 7]

[0122]

[0123] [Reaction Scheme 8]

[0124]

[0125] In reaction schemes 5 to 8, Ar 22 Ar 23 L 21 To L 23 R3 to R9, X, and c to i are defined as in Equation 4, Equation 1-1, and Equation 1-2.

[0126] Although illustrative synthetic examples of compounds represented by Formula 4 have been described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II) catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that the above reactions are carried out even when substituents defined in Formula 4 above but not specified in the specific synthetic examples are bonded.

[0127] The compound represented by Formula 1 may be selected from compounds 1-1 to 1-16, but is not limited thereto.

[0128] In the organic electroluminescent device according to this disclosure, the first electrode and the second electrode can each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first and second electrodes, the organic electroluminescent device can be a top-emitting, bottom-emitting, or side-emitting type. Furthermore, the hole injection layer can be further doped with a p-type dopant, and the electron injection layer can be further doped with an n-type dopant.

[0129] In the organic electroluminescent device according to this disclosure, the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. Additionally, in the organic electroluminescent device according to this disclosure, the organic layer may further comprise at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, organometallic compounds of lanthanides and d-transition elements, or at least one complex compound comprising said metal.

[0130] In addition to the compounds disclosed herein, the organic electroluminescent device of this disclosure may emit white light by further comprising at least one light-emitting layer containing a compound known in the art that emits blue, red, or green light. Additionally, if necessary, it may further comprise a yellow or orange light-emitting layer.

[0131] In the organic electroluminescent device disclosed herein, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") is preferably placed on one or more inner surfaces of one or two electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably placed on the anode surface of the electroluminescent dielectric layer, and a metal halide layer or metal oxide layer is preferably placed on the cathode surface of the electroluminescent dielectric layer. The surface layer can provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide includes SiO₂. X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0132] A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, can be used between the anode and the light-emitting layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein each of the multilayers can use two compounds simultaneously. The hole transport layer or electron blocking layer can also be multilayered.

[0133] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, or an electron injection layer, or a combination thereof, can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers can use two compounds simultaneously. The hole blocking layer or electron transport layer can also be multilayered, wherein each of the multilayers can use multiple compounds.

[0134] A light-emitting auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can promote hole injection and / or hole transport, or prevent electron overflow. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole overflow. Alternatively, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, effectively promoting or limiting the hole transport rate (or hole injection rate), thereby enabling charge balance control. Furthermore, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, blocking overflowing electrons from the light-emitting layer and confining excitons within the light-emitting layer to prevent light leakage. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. Hole auxiliary layers and electron blocking layers can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0135] In the organic electroluminescent device of this disclosure, it is preferable to place a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to produce an organic electroluminescent device having two or more light-emitting layers that emit white light.

[0136] According to one embodiment of this disclosure, organic electroluminescent materials can be used as luminescent materials for white organic light-emitting devices. Various structures for white organic light-emitting devices have been proposed, such as parallel arrangement (side-by-side) methods, stacking methods, or color conversion material (CCM) methods, depending on the arrangement of R (red), G (green), B (blue), or YG (yellow-green) luminescent units. Furthermore, the organic electroluminescent material according to one embodiment of this disclosure can also be applied to organic electroluminescent devices containing quantum dots (QDs).

[0137] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as spin coating, dip coating, flow coating, etc., can be used. The first and second host compounds of this disclosure can be co-evaporated or mixed-evaporated to form films.

[0138] When using a wet film-forming method, a thin film can be formed by dissolving or dispersing the materials forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. There are no particular restrictions on the solvent, as long as the materials constituting each layer are soluble or dispersible in the solvent, which will not cause any problems during film formation.

[0139] Display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be produced using the organic electroluminescent devices disclosed herein; or lighting systems, such as outdoor or indoor lighting systems.

[0140] The preparation methods of the compounds of this disclosure and the properties of the compounds will be explained in detail below with reference to representative compounds of this disclosure. However, this disclosure is not limited to the following examples.

[0141] Example 1: Preparation of compounds 1-3

[0142]

[0143] Synthesis of compound 1-3-2

[0144] Compound 1-3-3 (10 g, 34.3 mmol), 1-bromo-4-iodobenzene (24.3 g, 85.8 mmol), cuprous iodide (I) (3.27 g, 17.2 mmol), ethylenediamine (2.06 g, 34.3 mmol), and potassium phosphate (21.9 g, 103 mmol) were introduced into a flask containing toluene (170 mL) and dissolved. The mixture was refluxed for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and distilled water was added. After extraction with ethyl acetate, the residue was dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound 1-3-2 (13.2 g, yield: 86.2%).

[0145] Synthesis of compound 1-3-1

[0146] Compound 1-3-2 (13.2 g, 29.6 mmol), bis(pinacol)diboron (9.76 g, 38.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (830 mg, 1.18 mmol), and potassium acetate (12.8 g, 130 mmol) were introduced into a flask containing 295 mL of 1,4-dioxane and dissolved. The mixture was refluxed at 120 °C for 24 hours. After the reaction was complete, the organic layer was separated with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was separated by column chromatography to obtain compound 1-3-1 (9.4 g, yield: 64.4%).

[0147] Synthesis of compounds 1-3

[0148] Compound 1-3-1 (9.4 g, 19.1 mmol), compound A (6.35 g, 19.1 mmol), tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.953 mmol), and potassium carbonate (7.9 g, 57.2 mmol) were introduced into a flask containing toluene (78 mL), ethanol (23.5 mL), and water (23.5 mL) and dissolved. The mixture was refluxed at 120 °C for 24 hours. After the reaction was complete, the organic layer was separated with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was separated by column chromatography to obtain compound 1-3 (2.7 g, 4.36 mmol).

[0149] compound MW Tg MP 1-3 619.77 169.72℃ 319.6℃

[0150] Example 2: Preparation of compound 2-2

[0151]

[0152] Synthesis of compound 2-2-1

[0153] Compound 1-3-3 (15.0 g, 51.5 mmol), 1-bromo-3-iodobenzene (29.3 g, 103 mmol), cuprous iodide (I) (4.9 g, 25.8 mmol), ethylenediamine (7.0 mL, 103 mmol), and potassium phosphate (27.5 g, 129 mmol) were introduced into a flask containing toluene (250 mL) and dissolved. The mixture was stirred under reflux for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and filtered through silica gel. The organic layer was concentrated and recrystallized from ethyl acetate to obtain compound 2-2-1 (14.2 g, yield: 62%).

[0154] Synthesis of compound 2-2

[0155] Compound 2-2-1 (5.0 g, 11.2 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (3.0 g, 12.3 mmol), tris(dibenzylacetone)dipalladium(0) (0.5 g, 0.56 mmol), s-phos (0.46 g, 1.12 mmol), and sodium tert-butoxide (2.7 g, 28 mmol) were introduced into a flask containing toluene (60 mL) and dissolved. The mixture was stirred under reflux for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, stirred at room temperature, and methanol was added. The obtained solid was filtered under reduced pressure and separated by column chromatography to obtain compound 2-2 (2.3 g, yield: 34%).

[0156] compound MW Tg MP 2-2 610.8 112.31℃ 132℃

[0157] Example 3: Preparation of compounds 2-3

[0158]

[0159] Compound 2-2-1 (14.0 g, 31.4 mmol), N-phenyl-[1,1'-biphenyl]-3-amine (7.78 g, 31.7 mmol), tris(dibenzylacetone)dipalladium(0) (1.44 g, 1.57 mmol), tri-tert-butylphosphine (635 mg, 3.14 mmol), and sodium tert-butoxide (6.04 g, 62.8 mmol) were introduced into a flask containing toluene (160 mL) and dissolved. The mixture was stirred under reflux for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was distilled under reduced pressure and separated by column chromatography to obtain compound 2-3 (14.6 g, yield: 76%).

[0160] compound MW Tg MP 2-3 610.7 103.6℃ 141℃

[0161] Apparatus Example 1: Production of OLEDs deposited with organic electroluminescent compounds according to the present disclosure

[0162] OLEDs according to this disclosure are produced. A transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (GEOMATEC CO.,LTD., Japan) on a glass substrate for the OLED is sequentially ultrasonically washed with acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HT is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HI is introduced into another chamber. The two materials are evaporated at different rates, and compound HI is deposited at a doping amount of 3 wt% based on the total amount of compounds HT and HI to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT is deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Compound HT is deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm. After forming the hole injection layer and hole transport layer, the light-emitting layer is formed thereon as follows: Compounds 1-3 are introduced as the host of the light-emitting layer into one chamber of a vacuum vapor deposition apparatus, and compound BD is introduced into another chamber. The two materials are evaporated at different rates and deposited with a doping amount of 2 wt% based on the total amount of the host and dopant, respectively, to form a light-emitting layer with a thickness of 20 nm on the second hole transport layer. Subsequently, compound ET-1 is deposited as a hole blocking layer with a thickness of 5 nm. Next, compounds ET-2 and EI-1 are evaporated in two other chambers at a 1:1 ratio (by weight) to deposit an electron transport layer with a thickness of 30 nm on the hole blocking layer. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm, an Al cathode with a thickness of 80 nm is deposited using another vacuum vapor deposition apparatus to produce an OLED.

[0163] The results showed that the driving voltage was 3.2V and the power efficiency was 5.9lm / W at a brightness of 1,000 nits, and the shortest time to reduce the brightness from 100% to 95% was 31.1 hours.

[0164] Comparative Example: Production of OLEDs Containing Conventional Compounds

[0165] The OLED was produced in the same manner as in Device Example 1, except that compound BH-2 was used as the main body of the light-emitting layer.

[0166] The results showed that a driving voltage of 4.1V and a power efficiency of 5.9lm / W were achieved at a brightness of 1,000 nits, and the shortest time to reduce the brightness from 100% to 95% was 14.6 hours.

[0167] As can be seen from the above results, it is confirmed that compared with OLEDs using conventional compounds, OLEDs containing organic electroluminescent compounds according to this disclosure as the host material can significantly reduce the driving voltage and have significantly improved lifetime characteristics.

[0168] Apparatus Example 2: Production of OLEDs deposited with organic electroluminescent compounds according to the present disclosure

[0169] The OLED was produced in the same manner as in Device Example 1, except that compound 2-2 was used instead of compound HT as the second hole transport material.

[0170] The result is a driving voltage of 3.2V and a power efficiency of 6.9lm / W at a brightness of 1,000 nits.

[0171] Apparatus Example 3: Production of OLEDs deposited with organic electroluminescent compounds according to the present disclosure

[0172] The OLED was produced in the same manner as in Device Example 1, except that compounds 2-3 were used instead of compound HT as the second hole transport material.

[0173] The result is a driving voltage of 3.2V and a power efficiency of 6.9lm / W at a brightness of 1,000 nits.

[0174] As can be seen from the above results, OLEDs containing the organic electroluminescent compound according to this disclosure as both a second hole transport material and a host material can significantly reduce the driving voltage and exhibit significantly improved power efficiency characteristics compared to OLEDs using conventional compounds. By realizing an organic electroluminescent device with low power consumption, high power efficiency in the display implementation can represent a higher-performance display.

[0175] [Table 3]

[0176]

Claims

1. An organic electroluminescent compound, represented by the following formula 2-4: ----- (2-4) in L1 represents a single bond; L2 represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene; Ar1 represents substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted triphenyl; R1 to R5 each independently represent hydrogen, deuterium, deuterated or unsubstituted methyl, deuterated or unsubstituted ethyl, deuterated or unsubstituted n-propyl, deuterated or unsubstituted isopropyl, deuterated or unsubstituted n-butyl, deuterated or unsubstituted isobutyl, or deuterated or unsubstituted tert-butyl. The substituents of the substituted phenylene, substituted biphenylene, and substituted terphenylene in L2 and the substituted phenyl, substituted naphthyl, substituted biphenyl, and substituted terphenyl in Ar1 are at least one selected from the group consisting of: deuterium, deuterated or unsubstituted methyl, deuterated or unsubstituted ethyl, deuterated or unsubstituted n-propyl, deuterated or unsubstituted isopropyl, deuterated or unsubstituted n-butyl, deuterated or unsubstituted isobutyl, and deuterated or unsubstituted tert-butyl. a, b, and d each independently represent integers from 1 to 4, c represents integers from 1 to 5, and e represents integers from 1 to 3. If a to e are integers of 2 or greater, then each R1 to each R5 can be the same or different.

2. The organic electroluminescent compound according to claim 1, wherein, Ar1 indicates a substituted or unsubstituted phenyl group; L2 represents a single bond, or a substituted or unsubstituted phenylene; R1 to R5 each independently represent hydrogen or deuterium; The substituents of the substituted phenyl and substituted phenylene are deuterium.

3. The organic electroluminescent compound according to claim 1, wherein, The compounds represented by formula 2-4 are selected from the following compounds: 。 4. An organic electroluminescent device comprising a first electrode; a second electrode; and a plurality of organic layers, said organic layers including a light-emitting layer between the first electrode and the second electrode, wherein at least one of said organic layers comprises a compound represented by formulas 2-4: ----- (2-4) The definitions of Ar1, R1 to R5, L1, L2, and a to e are the same as in claim 1. At least one of the organic layers contains a compound represented by Formula 4: ----- (4) in Ar 21 To Ar 23 At least one of them independently represents the following equation 1-1, and Ar 21 To Ar 23 The other one or more in the group independently represent substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted 5- to 30-membered heteroaryl groups; L 21 To L 23 Each can be used independently to represent a single bond, or a substituted or unsubstituted C6-C30 aryl group; Among them, Ar 21 To Ar 23 The substituted or unsubstituted C6-C30 aryl group mentioned therein is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted fluorenyl. Where L 21 To L 23 The substituted or unsubstituted C6-C30 arylene group mentioned therein is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted fluorene. Among them, Ar 21 To Ar 23 The substituted or unsubstituted 5- to 30-membered heteroaryl groups mentioned herein are substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiopheneyl. The substituents of the substituted phenyl, substituted phenylene, substituted biphenyl, substituted biphenylene, substituted terphenyl, substituted terphenylene, substituted naphthyl, substituted naphthylene, substituted fluorenyl, substituted fluoreneylene, substituted dibenzofuranyl and substituted dibenzothiophene are at least one selected from the group consisting of: deuterium, deuterated or unsubstituted methyl, deuterated or unsubstituted ethyl, deuterated or unsubstituted n-propyl, deuterated or unsubstituted isopropyl, deuterated or unsubstituted n-butyl, deuterated or unsubstituted isobutyl and deuterated or unsubstituted tert-butyl; ----- (1-1) R3 to R5 each independently represent hydrogen, deuterium, deuterated or unsubstituted methyl, deuterated or unsubstituted ethyl, deuterated or unsubstituted n-propyl, deuterated or unsubstituted isopropyl, deuterated or unsubstituted n-butyl, deuterated or unsubstituted isobutyl, or deuterated or unsubstituted tert-butyl. X represents NR 11 ; R 11 With L 21 To L 23 One of the connections; and d represents an integer from 1 to 4, c represents an integer from 1 to 5, and e represents an integer from 1 to 3. If a to e are integers of 2 or greater, then each R3 to each R5 can be the same or different.

5. The organic electroluminescent device according to claim 4, wherein, The compound represented by formula 2-4 or 4 is contained in at least the light-emitting layer.

6. The organic electroluminescent device according to claim 4, wherein, The compound represented by formula 2-4 or 4 is contained in at least one layer of the organic layer between the first electrode and the light-emitting layer.

7. The organic electroluminescent device according to claim 4, wherein, Ar1 represents a deuterated or unsubstituted phenyl group; R1 to R5 each independently represent hydrogen or deuterium; The Ar 21 To Ar 23 The other one or more in the text each independently represent a deuterated or unsubstituted phenyl, or a deuterated or unsubstituted biphenyl; L 21 To L 23 Each represents a single key independently.

8. The organic electroluminescent device according to claim 4, wherein, The compound represented by Formula 4 is selected from the following compounds: 。 9. The organic electroluminescent device according to claim 4, wherein, The compounds represented by formula 2-4 are selected from the following compounds: 。

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