Organic electroluminescent device and organic electroluminescent compound therefor
By using a specific combination of compounds as the main material of the electron barrier layer and the light emitting layer in the organic electroluminescent device, the shortcomings of the organic electroluminescent device in the prior art in terms of high luminescence efficiency and long life are solved, and high efficiency and long life luminescent performance is achieved.
Patent Information
- Application Number
- CN202411734831.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-11-01
- Filing Date
- 2024-11-29
- Publication Date
- 2025-05-30
AI Technical Summary
Existing organic electroluminescent devices have shortcomings in high luminescence efficiency and long life, especially in applications with long-term use and high display resolution.
By using a specific combination of compounds as the host material of the electron barrier layer and the light emitting layer in an organic electroluminescent device, the luminescent efficiency and lifetime of the device are improved. Specifically, the electron barrier layer comprises a compound represented by Formula 1, the light emitting layer comprises at least two compounds, and at least one electron barrier layer is provided between the first electrode and the light emitting layer.
It realizes high luminous efficiency and long life of organic electroluminescent devices, and is suitable for long-term use and high display resolution applications.
Smart Images

Figure BDA0005161222910000021 
Figure BDA0005161222910000121 
Figure BDA0005161222910000131
Abstract
Description
Technical Field
[0001] The present disclosure relates to an organic electroluminescent device and an organic electroluminescent compound for the organic electroluminescent device. Background Art
[0002] A double-layer small molecule organic electroluminescent device (OLED) having green light emission composed of a light emitting layer and a charge transport layer 3 was first developed by Tang et al. of Eastman Kodak in 1987. Since then, research on organic electroluminescent devices has been rapidly carried out, and OLEDs have since been commercialized. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel implementations. Therefore, for long-term use and high display resolution, OLEDs with high luminous efficiency and / or long lifetime characteristics are required.
[0003] Korean Patent No. 10-2306966 discloses an organic electroluminescent device including a compound having phenanthrooxazole or phenanthrothiazole as a main core and a phenanthrene derivative as a host material, but does not specifically disclose an organic electroluminescent device having improved properties (such as high luminous efficiency and / or long lifetime characteristics) by using a specific combination of compounds as an electron blocking layer and a host material for a light emitting layer as in the present disclosure. Summary of the Invention
[0004] Technical Problem
[0005] An object of the present disclosure is to provide a compound that is effectively used for producing an organic electroluminescent device having high luminous efficiency and / or long lifetime characteristics, and an organic electroluminescent material including the compound.
[0006] Solution to the Problem
[0007] As a result of in-depth research to solve the above technical problems, the inventors of the present invention found that the above object can be achieved by an organic electroluminescent device including: a first electrode; a second electrode; a light emitting layer between the first electrode and the second electrode; and at least one electron blocking layer between the first electrode and the light emitting layer, wherein the electron blocking layer includes a compound represented by Formula 1, and the light emitting layer includes at least two compounds, thereby completing the present invention.
[0008]
[0009] In Formula 1,
[0010] R 1 to R 10Each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a (C3-C30) aliphatic ring and a substituted or unsubstituted fused ring of (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, or *-L 1 -N(Ar 1 )(Ar 2 ) provided that at least one of R 1 to R 10 is *-L 1 -N(Ar 1 )(Ar 2 );
[0011] L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; and
[0012] Ar 1 and Ar 2 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group.
[0013] Advantages of the present invention
[0014] By including a compound according to the present disclosure and / or an organic electroluminescent material containing the compound, an organic electroluminescent device having high luminous efficiency and / or long-life characteristics can be provided. Detailed embodiments
[0015] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and does not mean to limit the scope of the present disclosure in any way.
[0016] The organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; a light-emitting layer between the first electrode and the second electrode; and at least one electron blocking layer between the first electrode and the light-emitting layer, wherein the electron blocking layer contains a compound represented by Formula 1, and the light-emitting layer contains at least two compounds.
[0017] The organic electroluminescent device according to the present disclosure includes at least one hole assisting layer between the first electrode and the electron blocking layer.
[0018] The light-emitting layer according to the present disclosure contains at least one compound represented by Formula 2 and at least one compound represented by Formula 3.
[0019] The present disclosure provides an organic electroluminescent compound represented by Formula 1-1 as a compound for an organic electroluminescent device, and an organic electroluminescent device including the compound.
[0020] The present disclosure provides an organic electroluminescent compound represented by Formula 3' as a compound for an organic electroluminescent device, and an organic electroluminescent device including the compound.
[0021] As used herein, the term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any material layer constituting the organic electroluminescent device.
[0022] As used herein, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and that can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a light-emitting assisting 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, or an electron injection material, etc.
[0023] The term "plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material containing a combination of at least two compounds, which can be included in any layer constituting the organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of organic electroluminescent materials can be a combination of at least two compounds, and these at least two compounds can be included in at least one of the following layers: a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting assisting layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Therefore, the at least two compounds can be included in the same layer or different layers, and can be co-evaporated or co-evaporated, or can be evaporated individually.
[0024] In this text, the term "multiple host materials" means an organic electroluminescent material containing a combination of at least two host materials. It can mean both the material before being incorporated into an organic electroluminescent device (e.g., before vapor deposition) and the material after being incorporated into an organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of the present disclosure can be incorporated into any light-emitting layer constituting an organic electroluminescent device. At least two compounds contained in the multiple host materials can be contained together in one light-emitting layer, or can be contained separately in individual light-emitting layers. When at least two compounds are contained in one light-emitting layer, the at least two compounds can be co-evaporated by mixing to form a layer, or can be co-evaporated separately and simultaneously to form a layer.
[0025] In this text, "(C1-C30)(sub)alkyl" means a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. The above alkyl can include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. In this text, "(C3-C30)(sub)cycloalkyl" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. The above cycloalkyl can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In the present disclosure, "(3- to 7-membered)heterocycloalkyl" means a cycloalkyl having 3 to 7 ring skeleton atoms, preferably 5 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The "(C6-C30)(sub)aryl" in the present disclosure means a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15. The above aryl can be partially saturated and can contain a spiro structure. Specific examples of the aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthryl, benzoanthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, group, benzo groups, naphthacenyl, fluoranthenyl, benzo[a]fluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzo[a]fluorene]yl, azulyl, tetramethyl-dihydrophenanthrenyl, and the like. More specifically, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1- group, 2- group, 3- group, 4- group, 5- group, 6- group, benzo[c]phenanthryl, benzo[g] Base, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzo[a]fluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, etc. The "(3- to 30-membered)(hetero)aryl" in the present disclosure is an aryl group having 3 to 30 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, wherein the number of ring skeleton atoms is preferably 5 to 25. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above heteroaryl can be monocyclic or a fused ring condensed with at least one benzene ring and can be partially saturated. In addition, herein, the above heteroaryl can be a heteroaryl formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds. Specific examples of the heteroaryl can specifically include monocyclic ring-type heteroaryls, including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused ring-type heteroaryls, including benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienquinolinyl, benzothienquinazolinyl, benzothiennaphthyridinyl, benzothienpyrimidinyl, naphthothienpyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, silafluorene, germafluorene, benzotriazolyl, phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indacarbazolyl, etc. More specifically, the heteroaryl can be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-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, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-iso-benzofuryl, 3-iso-benzofuryl, 4-iso-benzofuryl, 5-iso-benzofuryl, 6-iso-benzofuryl, 7-iso-benzofuryl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-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-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothienyl, 2-naphtho-[1,2-b]-benzothienyl, 3-naphtho-[1,2-b]-benzothienyl, 4-naphtho-[1,2-b]-benzothienyl, 5-naphtho-[1,2-b]-benzothienyl, 6-naphtho-[1,2-b]-benzothienyl, 7-naphtho-[1,2-b]-benzothienyl, 8-naphtho-[1,2-b]-benzothienyl, 9-naphtho-[1,2-b]-benzothienyl, 10-naphtho-[1,2-b]-benzothienyl, 1-naphtho-[2,3-b]-benzothienyl, 2-naphtho-[2,3-b]-benzothienyl, 3-naphtho-[2,3-b]-benzothienyl, 4-naphtho-[2,3-b]-benzothienyl, 5-naphtho-[2,3-b]-benzothienyl, 1-naphtho-[2,1-b]-benzothienyl, 2-naphtho-[2,1-b]-benzothienyl, 3-naphtho-[2,1-b]-benzothienyl, 4-naphtho-[2,1-b]-benzothienyl, 5-naphtho-[2,1-b]-benzothienyl, 6-naphtho-[2,1-b]-benzothienyl, 7-naphtho-[2,1-b]-benzothienyl, 8-naphtho-[2,1-b]-benzothienyl, 9-naphtho-[2,1-b]-benzothienyl, 10-naphtho-[2,1-b]-benzothienyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothieno[3,2-d]pyrimidinyl, 6-benzothieno[3,2-d]pyrimidinyl, 7-benzothieno[3,2-d]pyrimidinyl, 8-benzothieno[3,2-d]pyrimidinyl, 9-benzothieno[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 2-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 82-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafuorenyl, 2-germafuorenyl, 3-germafuorenyl, 4-germafuorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. In addition, the “(hetero)aryl” can be classified into a (hetero)aryl having electron characteristics or a (hetero)aryl having hole characteristics. The (hetero)aryl having electron characteristics is a substituent having relatively rich electrons in the parent nucleus, and for example, it can be a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinolinyl, etc. The (hetero)aryl having hole characteristics is a substituent having relatively scarce electrons in the parent nucleus, and for example, it can be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl. In this document, the “fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring” means a ring formed by fusing at least one aliphatic ring having 3 to 30 ring backbone carbon atoms (where the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18) and at least one aromatic ring having 6 to 30 ring backbone carbon atoms (where the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18). For example, the fused ring can be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane, etc. In this document, the carbon atoms in the fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring can be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The “halogen” in the present disclosure includes F, Cl, Br, and I.,
[0026] In addition, “ortho-(o-)”, “meta-(m-)”, and “para-(p-)” mean to indicate the substitution positions of all substituents. The ortho-configuration describes a compound having substituents adjacent to each other, for example, at the 1-position and 2-position on benzene. The meta-configuration indicates the next substitution position adjacent to the substitution position, for example, the compound has substituents at the 1-position and 3-position on benzene. The para-configuration indicates the next substitution position to the meta-position, for example, the compound has substituents at the 1-position and 4-position on benzene.
[0027] As used herein, "a ring formed by connection with adjacent substituents" means a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by connecting or fusing two or more adjacent substituents, and preferably, it may be a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. Additionally, the formed ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 20; according to another embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 15. In one embodiment, the fused ring may be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, etc.
[0028] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., a substituent). Unless otherwise specified, at the position where the substituent can be substituted, the substituent is not limited to hydrogen, and when two or more hydrogen atoms in the functional group are each replaced by a substituent, the substituents can be the same or different from each other. It also includes the replacement of a hydrogen atom by a group formed by connecting two or more of the above substituents. For example, the "group formed by connecting two or more substituents" can be pyridine-triazine. That is to say, pyridine-triazine can be a heteroaryl group, or can be interpreted as a substituent in which two heteroaryl groups are connected. For example, in the present disclosure, "phenylnaphthyl" means naphthalene substituted by a phenyl group, and "naphthylphenyl" means benzene substituted by a naphthyl group.Preferably, the substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted (sub)aryl, substituted (sub)heteroaryl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted monoalkylamino or dialkylamino, substituted monoarylamino or diarylamino, substituted alkylarylamino, and substituted fused rings of aliphatic and aromatic rings in the formula of the present disclosure may each independently be substituted with at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with at least one (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and (3- to 30-membered)heteroaryl; tris(C1-C30)alkylsilyl; tris(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; tris(C6-C30)arylgeranyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; unsubstituted or mono- or di-(C6-C30)arylamino substituted with (C1-C30)alkyl; 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; (C2-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)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, etc. For example, the substituent may be substituted with deuterium, cyano, methyl, phenyl, naphthyl, triphenylsilyl, pyridyl, dibenzofuranyl, or dibenzothiophenyl, etc.
[0029] When a substituent is not shown in the chemical formula or compound structure of the present disclosure, this may mean that all positions where a substituent can appear are hydrogen or deuterium. That is, in the case of deuterium (an isotope of hydrogen), some hydrogen atoms can be deuterium, which is an isotope; and in this case, the content of deuterium can be from 0% to 100%. When a substituent is not shown in the chemical formula or compound structure of the present disclosure, when deuterium is not explicitly excluded (such as when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen), hydrogen and deuterium can be mixed and used in the compound. Deuterium is an element having a deuteron composed of one proton and one neutron as the atomic nucleus. Deuterium is one of the isotopes of hydrogen and can be represented by hydrogen-2, and the element symbol can be D or 2 H. Isotopes having the same atomic number (Z) and different mass numbers (A) can also be interpreted as elements having the same number of protons and different numbers of neutrons.
[0030] As used herein, "a combination thereof" means that one or more components of the corresponding list are combined to form a known or chemically stable arrangement, which can be conceived by those skilled in the art from the corresponding list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent; and a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl. For example, a preferred combination of substituents can include up to 50 atoms other than hydrogen and deuterium, or include up to 40 atoms other than hydrogen and deuterium, or include up to 30 atoms other than hydrogen and deuterium, or in many cases, a preferred combination of substituents can include up to 20 atoms other than hydrogen and deuterium.
[0031] In the formula of the present disclosure, when multiple substituents are represented by the same symbol, each of these substituents represented by the same symbol can be the same as or different from each other.
[0032] Hereinafter, an organic electroluminescent device according to an embodiment will be described in detail.
[0033] The organic electroluminescent device according to the present disclosure includes: a first electrode; a second electrode; a light-emitting layer between the first electrode and the second electrode; and at least one electron blocking layer between the first electrode and the light-emitting layer, wherein the electron blocking layer contains a compound represented by Formula 1, and the light-emitting layer contains at least two compounds.
[0034]
[0035] In Formula 1,
[0036] R 1 to R 10Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, (C3-C30) aliphatic ring and substituted or unsubstituted fused ring of (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tris(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 tris(C6-C30)arylsilyl, or *-L 1 -N(Ar 1 )(Ar 2 ) provided that at least one of R 1 to R 10 is *-L 1 -N(Ar 1 )(Ar 2 );
[0037] L 1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; and
[0038] Ar 1 and Ar 2 each independently represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.
[0039] In one embodiment, R 1 to R 1 which are not -L 2 -N(Ar 1 )(Ar 10 ) may each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R 1 to R 10Each independently may be hydrogen, deuterium, an unsubstituted or non-cyano-substituted phenyl group, an unsubstituted or non-phenyl-substituted naphthyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted dibenzofuranyl group. In one embodiment, L 1 may be a single bond, or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond, or a substituted or unsubstituted (C6-C25) arylene group, more preferably a single bond, or a substituted or unsubstituted (C6-C18) arylene group. For example, L 1 may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted p-biphenylene group, a substituted or unsubstituted m-biphenylene group, or a substituted or unsubstituted o-biphenylene group.
[0040] In one embodiment, Ar 1 and Ar 2 each independently may be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-membered to 18-membered) heteroaryl group. For example, Ar 1 and Ar 2 each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diethylfluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted benzonaphthothiophenyl group. Among them, the substituents may be substituted by at least one of deuterium, tert-butyl, amino, phenyl, p-biphenyl, m-terphenyl, fluorenyl, triphenylsilyl, naphthyl, phenanthryl, an unsubstituted or phenyl-substituted pyridyl group, dibenzothiophenyl, dibenzofuranyl, and carbazolyl.
[0041] According to one embodiment, the compound represented by Formula 1 may be more specifically illustrated by the following compounds, but not limited thereto:
[0042]
[0043]
[0044]
[0045]
[0046]
[0047]
[0048]
[0049] The compound represented by Formula 1 according to the present disclosure can be manufactured by referring to synthesis methods known to those skilled in the art, for example, the synthesis methods disclosed in Korean Patent Application Publication No. 2019-0101739, US Patent Application Publication No. US2017 / 0025609A1, etc., but not limited thereto.
[0050] According to one embodiment, the light-emitting layer includes at least one compound represented by Formula 2 and at least one compound represented by Formula 3.
[0051]
[0052] In Formula 2,
[0053] L 3 to L 5 each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene;
[0054] Ar 3 to Ar 5 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tris(C6-C30) arylsilyl, or -N(Ar 11 )(Ar 12 ); and
[0055] Ar 11 and Ar 12each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;
[0056] provided that in Formula 2, the case where L 3 to L 5 are all single bonds and Ar 3 to Ar 5 are all hydrogen is excluded.
[0057] In one embodiment, L 3 to L 5 each independently may be a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5- to 25-membered) heteroarylene group, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene group, or a substituted or unsubstituted (5- to 18-membered) heteroarylene group. For example, L 3 to L 5 each independently may be a single bond, or a phenylene group that is unsubstituted or substituted with a phenyl group or a pyridyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted o-biphenylene group, a substituted or unsubstituted m-biphenylene group, a substituted or unsubstituted p-biphenylene group, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted carbazolylene group.
[0058] In one embodiment, Ar 3 to Ar 5 each independently may be a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5- to 30-membered) heteroaryl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, or -N(Ar 11 )(Ar 12 ), preferably a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5- to 25-membered) heteroaryl group, a substituted or unsubstituted tris(C6-C25)arylsilyl group, or -N(Ar 11 )(Ar 12 ), more preferably a substituted or unsubstituted (C1-C4) alkyl group, a substituted or unsubstituted (C6-C18) aryl group, a substituted or unsubstituted (5- to 18-membered) heteroaryl group, a substituted or unsubstituted tris(C6-C18)arylsilyl group, or -N(Ar 11 )(Ar 12 ). Among them, Ar 11 and Ar12 Each independently may be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5-membered to 18-membered) heteroaryl. For example, Ar 3 to Ar 5 Each independently may be an unsubstituted phenyl or a phenyl substituted with deuterium or cyano, an unsubstituted isopropyl or an isopropyl substituted with phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted o-quaterphenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted group, an unsubstituted fluorenyl or a fluorenyl substituted with at least one methyl, an unsubstituted fluorenyl or a fluorenyl substituted with at least one phenyl, a substituted or unsubstituted 9,9,10,10-tetramethylphenanthryl, a substituted or unsubstituted triphenylsilyl, a substituted or unsubstituted pyridyl, a carbazolyl, an unsubstituted or deuterium-substituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted phenanthrolinyl, a substituted or unsubstituted dibenzoselenophenyl, or a substituted or unsubstituted naphthobenzoselenophenyl. Among them, the substituent may be further substituted with at least one of deuterium, methyl and phenyl.
[0059] For example, Ar 11 and Ar 12 Each independently may be an unsubstituted phenyl or a phenyl substituted with diphenylamino, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl.
[0060] According to one embodiment, at least one of Ar 3 to Ar 5 may be represented by any one of the following formulas 2-1 to 2-3.
[0061]
[0062] In formula 2-1,
[0063] X 1 and Y 1 Each independently represents -N=, -NR 25-, -O-, or -S-; provided that X 1 and Y 1 is any one of -N=, and X 1 and Y 1 the other of which is -NR 25 -, -O-, or -S-;
[0064] R 21 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl;
[0065] R 22 to R 25 each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to adjacent substituents to form one or more rings;
[0066] a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 3;
[0067] and when a to c are integers of 2 or greater, each R 22 to each R 24 may be the same as or different from each other; and
[0068] * represents the linking position to L in Formula 2 3 to L 5 ;
[0069]
[0070] In Formula 2-2,
[0071] Y represents -O-, -S-, or -NR 39 ;
[0072] R 39 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; and
[0073] R 31 to R 38 each independently represents a connection position to L in Formula 2 3 to L 5 ; or 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 tris(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 tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to adjacent substituents to form one or more rings.
[0074]
[0075] In Formulas 2-3,
[0076] T represents -O-, -S-, -CR 45 R 46 , -NR 47 , or -Se-;
[0077] R 45 to R 47 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl;
[0078] R 41 to R 44 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -N(Ar 21 )(Ar 22 ); or may be connected to adjacent substituents to form one or more rings;
[0079] Ar 21 and Ar 22each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;
[0080] d and g each independently represent an integer from 1 to 4, and e and f each independently represent an integer of 1 or 2;
[0081] When d to g are integers of 2 or greater, each R 41 to each R 44 can be the same as or different from each other; and
[0082] * represents the connection position to L in Formula 2 3 to L 5 of.
[0083] According to one embodiment, the compound represented by Formula 2-3 can be represented by the following Formula 2-3-1 or 2-3-2.
[0084]
[0085] In Formulas 2-3-1 and 2-3-2,
[0086] T, R 41 to R 44 and d to g are as defined in Formula 2-3.
[0087] In Formula 2-1, R 21 can be a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (5- to 30-membered) heteroaryl group, for example, an unsubstituted or deuterium-substituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted p-biphenyl group, or a substituted or unsubstituted pyridyl group.
[0088] In Formula 2-1, R 22 to R 25 each independently can be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group, preferably hydrogen, deuterium, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group, more preferably hydrogen, deuterium, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5- to 18-membered) heteroaryl group. For example, R 22 to R 25Each independently may be hydrogen, deuterium, phenyl which is unsubstituted or substituted with naphthyl or triphenylsilyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted p-terphenyl, fluorenyl which is unsubstituted or substituted with at least one methyl group, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.
[0089] In Formula 2-2, one of R 31 to R 38 may be the connecting position connected to L 3 to L 5 in Formula 2.
[0090] In Formula 2-3, T may be -O- or -S-.
[0091] In Formula 2-3, R 41 to R 44 each independently may be hydrogen or deuterium, substituted or unsubstituted (C6-C30) aryl, or -N(Ar 21 )(Ar 22 ), for example, hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted diphenylamine. For example, Ar 21 and Ar 22 each independently may be substituted or unsubstituted phenyl.
[0092] According to one embodiment, the compound represented by Formula 2 may be more specifically illustrated by the following compounds, but is not limited thereto:
[0093]
[0094]
[0095]
[0096]
[0097]
[0098]
[0099]
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106]
[0107]
[0108]
[0109]
[0110]
[0111]
[0112]
[0113]
[0114]
[0115]
[0116]
[0117]
[0118]
[0119]
[0120]
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129] In the above compounds, D n means that n number of hydrogens are replaced by deuterium, where n is an integer of 1 or greater, and the upper limit of n is determined according to the number of hydrogens that can be substituted in each compound.
[0130] The compounds represented by Formula 2 according to the present disclosure can be prepared by referring to synthetic methods known to those skilled in the art, for example, the synthetic methods disclosed in Korean Patent Application Publication Nos. 2018-0099487, 2021-0098316, 2022-0051794, etc., but not limited thereto.
[0131]
[0132] In Formula 3,
[0133] X 1 to X 3 each independently represents N or CR 11 ; provided that at least one of X 1 to X 3 is N;
[0134] L 7 to L 9 each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene;
[0135] R 11 represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;
[0136] Ar 7 to Ar 9Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C3-C30) aliphatic ring and a substituted or unsubstituted (C6-C30) aromatic ring fused ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, or -L 21 -N(Ar 21 )(Ar 22 );
[0137] L 21 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; and
[0138] Ar 21 and Ar 22 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group.
[0139] In one embodiment, at least two of X 1 to X 3 can be N.
[0140] In one embodiment, all of X 1 to X 3 can be N.
[0141] In one embodiment, each of L 7 to L 9 independently can be a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5- to 25-membered) heteroarylene group, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene group, or a substituted or unsubstituted (5- to 18-membered) heteroarylene group. For example, each of L 7 to L 9Each independently represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthophenylene, a substituted or unsubstituted phenylnaphthylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl, wherein the substituent may be substituted by at least one deuterium, for example.
[0142] In one embodiment, Ar 7 to Ar 9 Each independently may be a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-membered to 18-membered) heteroaryl.
[0143] In one embodiment, at least one of Ar 7 to Ar 9 may be a substituted or unsubstituted (5-membered to 30-membered) heteroaryl, preferably at least two of Ar 7 to Ar 9 may be a substituted or unsubstituted (5-membered to 30-membered) heteroaryl. For example, Ar 7 to Ar 9 Each independently may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylsilyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted benzophenanthryl, a substituted or unsubstituted group, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluoranthenyl, or a substituted or unsubstituted benzonaphthofuranyl. Among them, the substituent may be substituted by at least one of deuterium, cyano, phenyl, and naphthyl, for example.
[0144] According to one embodiment, at least one of Ar 7 to Ar 9 in Formula 3 may be represented by any one of the following Formulas 2-2, 3-1, and 3-2.
[0145]
[0146] In Formula 2-2,
[0147] Y represents -O-, -S-, or -NR 39 ;
[0148] R 39 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl; and
[0149] R 31 to R 38 each independently represents a linking position connected to L in Formula 3 7 to L 9 ; or 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 tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to adjacent substituents to form one or more rings.
[0150]
[0151] In Formulas 3-1 and 3-2
[0152] R 51 to R 64 each independently represents a linking position connected to L in Formula 3 7 to L 9a connecting position; or a hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (3- to 30-membered) heteroaryl group, substituted or unsubstituted tris(C1-C30)alkylsilyl group, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, substituted or unsubstituted tris(C6-C30)arylsilyl group, substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino group, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino group, substituted or unsubstituted mono- or di-(C6-C30)arylamino group, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino group, substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered) heteroarylamino group, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino group, substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered) heteroarylamino group, or substituted or unsubstituted (C6-C30)aryl(3- to 30-membered) heteroarylamino group.
[0153] In Formula 2-2, one of R 31 to R 38 may be a connecting position connected to L 7 to L 9 in Formula 3.
[0154] In Formula 3-1, one of R 51 to R 60 may be a connecting position connected to L 7 to L 9 in Formula 3.
[0155] In Formula 3-2, one of R 51 to R 58 and one of R 61 to R 64 may be a connecting position connected to L 7 to L 9 in Formula 3.
[0156] According to one embodiment, the compound represented by Formula 3 may be more specifically illustrated by the following compounds, but is not limited thereto:
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172] In the above compounds, D n means that n number of hydrogens are replaced by deuterium, where n is an integer of 1 or greater, and the upper limit of n is determined according to the number of hydrogens that can be substituted in each compound.
[0173] The compounds represented by Formula 3 according to the present disclosure can be prepared by referring to synthesis methods known to those skilled in the art. For example, the synthesis methods disclosed in Korean Patent Application Publication Nos. 2022-0051794, 2021-0124018, 2021-010943, etc., but not limited thereto.
[0174] According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by Formula 1-1 below.
[0175]
[0176] In Formula 1-1,
[0177] R 1 to R 10Each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a (C3-C30) aliphatic ring and a substituted or unsubstituted fused ring of a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, or *-L 1 -N(Ar 1 )(Ar 2 ) provided that at least one of R 1 to R 10 is *-L 1 -N(Ar 1 )(Ar 2 );
[0178] L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; and
[0179] Ar 1 and Ar 2 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;
[0180] provided that if R 1 , R 2 , R 4 , R 5 , R 8 , or R 9 is *-L 1 -N(Ar 1 )(Ar 2 ), then the following conditions are satisfied.
[0181] (1) If R 5 or R 8 is *-L 1 -N(Ar 1 )(Ar 2 ), then at least one of Ar 1 and Ar 2 is an unsubstituted or deuterium-substituted phenyl group;
[0182] (2) If R 1 or R 2 is *-L 1 -N(Ar 1 )(Ar 2 ), then at least one of Ar 1 and Ar 2 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group; or Ar 1 and Ar 2 are all substituted or unsubstituted (3- to 30-membered) heteroaryl groups; and
[0183] (3) If R 4 or R 9 is *-L 1 -N(Ar 1 )(Ar 2 ), then Ar 1 and Ar 2 are all substituted or unsubstituted (3- to 30-membered) heteroaryl groups; or at least one of Ar 1 and Ar 2 is a substituted or unsubstituted carbazolyl group.
[0184] According to one embodiment, the organic electroluminescent compound represented by Formula 1-1 can be more specifically illustrated by the following compounds, but is not limited thereto:
[0185]
[0186]
[0187]
[0188] According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by Formula 3'.
[0189]
[0190] In Formula 3',
[0191] X 1 to X 3 each independently represents N or CR 11 ; provided that at least one of X 1 to X 3 is N;
[0192] R 11represents 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 tris(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 tris(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;
[0193] L 7 to L 9 each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; and
[0194] Ar 7 to Ar 9 each independently represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tris(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 tris(C6-C30)arylsilyl, or -L 21 -N(Ar 21 )(Ar 22 );
[0195] provided that at least one of Ar 7 to Ar 9 is of formula 2-2.
[0196]
[0197] In formula 2-2,
[0198] Y represents -O- or -S-; and
[0199] R 31 to R 38 each independently represents attached to L in formula 3 7 to L 9the connecting position; or 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 tris(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 tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to adjacent substituents to form one or more rings;
[0200] provided that if L 7 to L 9 one of which is an unsubstituted or deuterium- or cyano-substituted phenylene, then at least one of Ar 7 to Ar 9 is an unsubstituted or deuterium- or cyano-substituted binaphthyl, and if L 7 to L 9 one of which is an unsubstituted or deuterium- or cyano-substituted naphthylene, then at least one of Ar 7 to Ar 9 is an unsubstituted or deuterium- or cyano-substituted phenylnaphthyl.
[0201] In one embodiment, in Formula 3', if L 7 to L 9 one of which is an unsubstituted or deuterium- or cyano-substituted phenyl, then at least one of Ar 7 to Ar 9 may be an unsubstituted or deuterium- or cyano-substituted substituent, as shown below.
[0202]
[0203] where * represents the connecting position to one of L 7 to L 9
[0204] In one embodiment, in Formula 3', if L 7 to L 9 one of which is an unsubstituted or deuterium- or cyano-substituted naphthylene, then at least one of Ar 7 to Ar 9 may be an unsubstituted or deuterium- or cyano-substituted substituent, as shown below.
[0205]
[0206] where * indicates a connection position connected to one of L 7 to L 9 in the connection position.
[0207] According to one embodiment, the compound represented by Formula 3' can be more specifically exemplified by the following compounds, but is not limited thereto:
[0208]
[0209]
[0210]
[0211]
[0212]
[0213] In the above compounds, D n means that n number of hydrogens are replaced by deuterium, where n is an integer of 1 or greater, and the upper limit of n is determined according to the number of hydrogens that can be substituted in each compound.
[0214] Hereinafter, an organic electroluminescent device including the compounds represented by the above Formulas 1 to 3, 1-1, and 3' will be described.
[0215] An organic electroluminescent device according to one embodiment includes a first electrode and a second electrode facing each other on a substrate, at least one light-emitting layer located between the first electrode and the second electrode, and at least one electron blocking layer located between the first electrode and the light-emitting layer.
[0216] According to one embodiment, the first electrode may be an anode, and the second electrode may be a cathode. Among them, the first electrode and the second electrode may 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 electrode and the second electrode, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.
[0217] The electron blocking layer is located between the first electrode and the light-emitting layer, preferably between the hole transport layer and the light-emitting layer, and more preferably, the electron blocking layer is in contact with the light-emitting layer. The electron blocking layer according to an example can improve the efficiency of the organic electroluminescent device by suppressing the transfer of electrons injected from the cathode to the anode without recombination in the light-emitting layer. In addition, it can prevent emission leakage by blocking the overflow of electrons from the light-emitting layer and confining excitons within the light-emitting layer.
[0218] According to one embodiment, the electron blocking layer contains a compound represented by Formula 1, and the light emitting layer may contain a compound represented by Formula 2 as a first host compound and a compound represented by Formula 3 as a second host compound, respectively. Among them, the weight ratio of the first host compound to the second host compound contained in the light emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50.
[0219] According to one embodiment, the organic electroluminescent device includes at least one compound selected from Compounds H1-1 to H1-161 as an electron blocking layer material, and at least one compound selected from Compounds H3-1 to H3-743 and at least one compound selected from Compounds H4-1 to H4-484, and at least one compound selected from Compounds H5-1 to H5-402 as host materials for the light emitting layer, where these host materials may be included in the same light emitting layer and may be included in different light emitting layers, respectively.
[0220] According to one embodiment, the present invention provides an organic electroluminescent device including an organic electroluminescent compound represented by Formula 1-1.
[0221] According to one embodiment, the present invention provides an organic electroluminescent device including an organic electroluminescent compound represented by Formula 3'.
[0222] An organic electroluminescent device according to an embodiment includes, in addition to an electron blocking layer and a light emitting layer, a hole injection layer, a hole transport layer, a hole assisting layer, an electron transport layer, and an electron injection layer as organic layers disposed between a first electrode and a second electrode, and may further include one or more layers selected from a light emitting assisting layer, an intermediate layer, a hole blocking layer, and an electron buffer layer. In addition to the light emitting materials of the present disclosure, the organic layers may further contain an amine-based compound and / or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole assisting layer, the light emitting layer, the light emitting assisting layer, or the electron blocking layer may contain an amine-based compound (e.g., an arylamine-based compound, a styrylarylamine-based compound, etc.) as a hole injection material, a hole transport material, a hole assisting material, a light emitting material, a light emitting assisting material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may contain an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layers may further contain at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organometals of d-transition elements, or at least one complex compound containing such a metal.
[0223] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each of the multilayer may use two compounds simultaneously. In addition, the hole injection layer may be doped with a p-type dopant.
[0224] The hole transport layer or the electron blocking layer according to an embodiment may be multilayered, and each layer may use a plurality of compounds.
[0225] The hole assisting layer is located between the hole transport layer and the electron blocking layer (or the light emitting layer), and may exhibit an effect of promoting or blocking the hole transport speed (or injection speed), thereby controlling the charge balance to effectively reduce the driving voltage of the organic electroluminescent device. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer may also serve as a hole assisting layer or an electron blocking layer.
[0226] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be a multi-layer to control the injection of electrons and improve the interfacial characteristics between the light-emitting layer and the electron injection layer, and each of the multi-layers may use two compounds simultaneously. The hole blocking layer may be placed between the electron transport layer (or electron injection layer) and the light-emitting layer, and block holes from reaching the cathode, thereby increasing the probability of recombination of electrons and holes in the light-emitting layer. The hole blocking layer or the electron transport layer may also be multi-layers, and each layer may use multiple compounds. In addition, the electron injection layer may be doped with an n-type dopant.
[0227] The organic electroluminescent device of the present disclosure may further include a light-emitting auxiliary layer placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it may be used to facilitate hole injection and / or hole transport, or to prevent electron spillage. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to facilitate electron injection and / or electron transport, or to prevent hole spillage. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have the effect of improving the efficiency and / or lifespan of the organic electroluminescent device.
[0228] The organic electroluminescent material according to one embodiment may be used as a light-emitting material for a white organic light-emitting device. Depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units, white organic light-emitting devices have various proposed structures, such as a parallel side-by-side arrangement method, a stacked arrangement method, or a CCM (color conversion material) method, etc. In addition, the compound or organic electroluminescent material according to one embodiment may also be applied to an organic electroluminescent device containing QD (quantum dots).
[0229] In the organic electroluminescent device of the present disclosure, preferably at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "surface layer") may be placed on one or more inner surfaces of one of the pair of electrodes or both electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The operating stability of the organic electroluminescent device can be obtained through the surface layer. Preferably, the chalcogenide includes SiO X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF 2 , CaF 2 , rare earth metal fluorides, etc.; and the metal oxide includes Cs 2 O, Li2 O, MgO, SrO, BaO, CaO, etc.
[0230] The organic electroluminescent device according to an embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to an embodiment, a single light-emitting unit (light-emitting unit) may be formed in a structure in which two or more units are connected through a charge generation layer. The organic electroluminescent device may include a plurality of two or more light-emitting units. For example, a plurality of three or more light-emitting units, the light-emitting unit having a first electrode and a second electrode opposite to each other on a substrate and a light-emitting layer stacked between the first electrode and the second electrode and emitting light in a specific wavelength range. According to an embodiment, the organic electroluminescent device may include a plurality of light-emitting units, and each of these light-emitting units may include a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region may include a hole injection layer and a hole transport layer, and the electron transport region may include an electron transport layer and an electron injection layer. According to an embodiment, three or more light-emitting layers may be included in the light-emitting unit. The plurality of light-emitting units may emit the same color or different colors. In addition, one light-emitting unit may include one or more light-emitting layers, and the plurality of light-emitting layers may be light-emitting layers of the same or different colors. It may include one or more charge generation layers located between each light-emitting unit. The charge generation layer is a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer may be located between the respective light-emitting units. Here, the plurality of charge generation layers may be the same as or different from each other. By providing a charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit increases, and the charge can be evenly distributed. Specifically, the charge generation layer is provided between two adjacent stacked layers and can be used to drive a tandem organic electroluminescent device using only a pair of anodes and cathodes without the need for a separate internal electrode located between the stacked layers.
[0231] The charge generation layer may be composed of an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The p-type charge generation layer may be made of a metal or an organic material doped with a p-type dopant. For example, the metal may be made of an alloy of one or two or more selected from the group consisting of: Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials may be used as the p-type dopant and the host material used in the p-type doped organic material.
[0232] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant, may be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to a cation; thus, it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, the reducing dopant layer may be used as a charge generation layer to fabricate an organic electroluminescent device having two or more light-emitting layers and emitting white light.
[0233] The organic electroluminescent device according to one embodiment may further include at least one dopant in the light-emitting layer.
[0234] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be one or more metalated complex compounds of one or more metal atoms selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more ortho-metalated complex compounds of one or more metal atoms selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably one or more ortho-metalated iridium complex compounds.
[0235] The dopant included in the organic electroluminescent device of the present disclosure may use the compound represented by Formula 101, but is not limited thereto.
[0236]
[0237] In Formula 101,
[0238] L is any one selected from the following Structures 1 to 3:
[0239]
[0240] In Structures 1 to 3,
[0241] R 100 to R 103Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or deuterium- and / or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a cyano group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to adjacent substituents to form one or more rings, such as forming one or more rings with pyridine, for example, a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indolopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indoloquinoline;
[0242] R 104 to R 107 Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or deuterium- and / or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a cyano group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to one or more adjacent substituents to form one or more substituted or unsubstituted rings, such as forming one or more substituted or unsubstituted rings with benzene, for example, a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indolopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothienopyridine;
[0243] R 201 to R 220 Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or deuterium- and / or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be linked to one or more adjacent substituents to form one or more substituted or unsubstituted rings; and
[0244] s represents an integer from 1 to 3.
[0245] Specifically, specific examples of the dopant compound include the following, but are not limited thereto.
[0246]
[0247]
[0248]
[0249]
[0250]
[0251] The organic electroluminescent device of the present disclosure can be manufactured as follows: forming a first electrode or a second electrode on a substrate; and then forming an organic layer using either a dry film-forming method (such as vacuum deposition, sputtering, plasma, or ion plating) or a wet film-forming method (such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, or flow coating); and then forming a second electrode or a first electrode thereon. When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material for forming each layer can be dissolved or diffused and which has no problem in film-forming ability.
[0252] When forming a layer with an organic electroluminescent material according to an embodiment, the layer can be formed by the methods listed above and can generally be formed by co-deposition or mixed deposition. Co-deposition is a mixed deposition method in which two or more materials are placed in corresponding individual crucible sources and current is applied to two chambers simultaneously to evaporate the materials; and mixed deposition is a mixed deposition method in which two or more materials are mixed in one crucible source before deposition and then current is applied to one chamber to evaporate the materials.
[0253] According to an embodiment, the present disclosure can provide a display device including a compound represented by Formulas 1 to 3 as an organic electroluminescent material. In addition, the organic electroluminescent device of the present disclosure can be used to manufacture display devices such as smartphones, tablets, laptop computers, PCs, TVs, or display devices of vehicles, or lighting devices such as outdoor or indoor lighting.
[0254] [Example 1] Synthesis of Compound H1-149
[0255]
[0256] Compound 1-1 (6.6 g, 25.91 mmol), Compound 1-2 (10 g, 23.56 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3(1.07 g, 1.178 mmol), sodium tert-butoxide (NaOt-Bu) (3.4 g, 35.34 mmol), and s-phos (0.96 g, 2.356 mmol) were added to 120 mL of o-xylene, and then stirred at 120 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, filtered through diatomaceous earth, and distilled under reduced pressure. Next, it was separated by column chromatography to obtain compound H1-149 (7.1 g, yield: 50%).
[0257] MW M.P H1-149 600.7 165.3℃
[0258] [Example 2] Synthesis of Compound H1-146
[0259]
[0260] Compound 2-1 (2.4 g, 8.482 mmol), compound 1-2 (3 g, 7.068 mmol), Pd 2 (dba) 3 (0.32 g, 0.353 mmol), NaOt-Bu (1 g, 10.60 mmol), and s-phos (0.29 g, 0.706 mmol) were added to 35 mL of o-xylene, and then stirred at 120 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, filtered through diatomaceous earth, and distilled under reduced pressure.
[0261] Next, it was separated by column chromatography to obtain compound H1-146 (4.2 g, yield: 87%).
[0262] MW M.P H1-146 676.8 268.8℃
[0263] [Example 3] Synthesis of Compound H1-161
[0264]
[0265] Compound 3-1 (10.0 g, 30.0 mmol), compound 3-2 (10.53 g, 31.5 mmol), Pd 2 (dba) 3 (1.4 g, 1.5 mmol), S-phos (1.2 g, 3.0 mmol), and NaOtBu (4.3 g, 45.0 mmol) were added to 150 mL of o-xylene, and then refluxed and stirred at 120 °C for 1 h. After the reaction was completed, the mixture was cooled to room temperature and separated into layers (EA / H 2O). Next, filter with diatomaceous earth and then filter with silica to produce a solid. Next, filter it to obtain Compound H1-161 (2.4 g, yield: 14%).
[0266] MW M.P H1-161 586.7 208℃
[0267] [Example 4] Synthesis of Compound H1-147
[0268]
[0269] Add Compound 4-1 (3.3 g, 11.4 mmol), Compound 1-2 (4.65 g, 11.4 mmol), NaOtBu (1.64 g, 17.1 mmol), S-Phos (374 mg, 0.912 mmol), Pd 2 (dba) 3 (522 mg, 0.57 mmol), and 57 mL of xylene into a flask and then dissolve, and reflux and stir at 160 °C for 30 minutes. After the reaction is completed, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain Compound H1-147 (4 g, yield: 51%).
[0270] MW M.P H1-147 676.82 275.3℃
[0271] Hereinafter, a method for preparing an organic electroluminescent device including a compound according to the present disclosure and an organic electroluminescent material including the compound, and device characteristics thereof will be explained in order to understand the present disclosure in detail.
[0272] [Device Example 1] Preparation of an OLED Containing a Compound According to the Present Disclosure
[0273] Fabricate an OLED according to the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) serving as a transparent electrode on a glass substrate for the OLED is subjected to ultrasonic washing successively with acetone and isopropyl alcohol, and thereafter stored in isopropyl alcohol and then used. Thereafter, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, compound HI-1 is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-1 to form a hole injection layer with a thickness of 10 nm. Then, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Then, compound HT2-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a second hole transport layer with a thickness of 55 nm on the first hole transport layer. Then, compound H1-42 is introduced as an electron blocking layer material, and an electron blocking layer with a thickness of 5 nm is deposited on the second hole transport layer. The first host compound and the second host compound described in Table 1 below as hosts are respectively introduced into two chambers of the vacuum vapor deposition apparatus, and compound D-39 is introduced as a dopant into another chamber, and then the two host materials are evaporated at a rate of 1:1, and the dopant material is evaporated simultaneously at a different rate, and the dopant material is deposited with a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the electron blocking layer. Next, compound ETL-1 and compound EIL-1 are evaporated as electron transport materials at a weight ratio of 50:50 to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. Next, compound EIL-1 is deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode with a thickness of 80 nm is deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED is produced. Each compound used for all materials is purified by vacuum sublimation at 10 -6 torr.
[0274] [Device Examples 2 to 22] Preparation of an OLED Containing a Compound According to the Present Disclosure
[0275] Except for using the compounds shown in Tables 1 to 4 below as the second hole transport layer material and as the host material of the light-emitting layer, an OLED is fabricated in the same manner as in Device Example 1.
[0276] [Comparative Examples 1 to 22] Preparation of an OLED Excluding an Electron Blocking Layer
[0277] Except for using the compounds shown in Tables 1 to 4 below as the second hole transport layer material and as the host material of the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 1, excluding the electron blocking layer, and a second hole transport layer with a thickness of 60 nm was deposited.
[0278] The driving voltage, luminous efficiency, and emission color of the OLEDs of Device Examples 1 to 22 and Comparative Examples 1 to 22 produced as described above were measured at a brightness of 5,000 nits, and the time taken for the brightness to decrease from 100% to 95% at a brightness of 10,000 nits (lifetime: T95), and the results are shown in Tables 1 to 4 below.
[0279] Table 1
[0280]
[0281]
[0282] Table 2
[0283]
[0284]
[0285] Table 3
[0286]
[0287] Table 4
[0288]
[0289] It can be confirmed from Tables 1 to 4 above that the organic electroluminescent devices (Device Examples 1 to 22) containing the compounds according to the present disclosure as the electron blocking layer material and containing a specific combination of the compounds according to the present disclosure as the host material exhibit a luminous efficiency equal to or greater than that of the organic electroluminescent devices excluding the electron blocking layer (Comparative Examples 1 to 22), and in particular, have significantly improved lifetime characteristics.
[0290] [Device Examples 23 to 28] Preparation of OLEDs Containing Compounds According to the Present Disclosure
[0291] Except for using the compounds shown in Table 5 below as the second hole transport layer material and as the host material of the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 1, excluding the electron blocking layer, and a second hole transport layer with a thickness of 60 nm was deposited.
[0292] [Comparative Example 23] Preparation of an OLED Excluding the Electron Blocking Layer
[0293] Except for using the compounds shown in Table 5 below as the second hole transport layer material and as the host material of the light-emitting layer, an OLED was fabricated in the same manner as in Device Example 1, excluding the electron blocking layer, and a second hole transport layer with a thickness of 60 nm was deposited; in addition, the second host compound described in Table 5 was introduced into one chamber in the vacuum vapor deposition equipment, and Compound D-39 was introduced as a dopant into another chamber, and then 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 with a thickness of 40 nm on the second hole transport layer.
[0294] The driving voltage, luminous efficiency, and emission color of the OLEDs of Device Examples 23 to 28 and Comparative Example 23 produced as described above were measured at a brightness of 5,000 nits, and the time taken for the brightness to decrease from 100% to 95% at a brightness of 10,000 nits (lifetime: T95), and the results are shown in Table 5 below.
[0295] Table 5
[0296]
[0297] It can be confirmed from Table 5 above that, compared with Comparative Example 23, the organic electroluminescent devices (Device Examples 23 to 28) containing a specific combination of the compounds according to the present disclosure as the light-emitting layer material exhibit a lower driving voltage and a higher luminous efficiency, and in particular, significantly improved lifetime characteristics.
[0298] The compounds used in the device examples and comparative examples are specifically shown in Table 6 below.
[0299] Table 6
[0300]
[0301]
[0302]
Claims
1. An organic electroluminescent device, comprising: a first electrode; a second electrode; a light emitting layer between the first electrode and the second electrode; as well as at least one electron blocking layer between the first electrode and the light emitting layer, The electron blocking layer comprises a compound represented by the following Formula 1, and the light emitting layer comprises at least two compounds: in, R1 to R 10 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) )heteroaryl, 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, or *-L1-N(Ar1)(Ar2); provided that R1 to R 10 At least one of them is *-L1-N(Ar1)(Ar2); L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group.
2. The organic electroluminescent device according to claim 1, wherein: The organic electroluminescent device includes at least one hole auxiliary layer between the first electrode and the electron blocking layer.
3. The organic electroluminescent device according to claim 1, wherein: The light-emitting layer includes at least one compound represented by the following formula 2 and at least one compound represented by the following formula 3: in L3 to L5 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene group, a substituted or unsubstituted (C6-C30)arylene group, a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group, or a substituted or unsubstituted (C3-C30)cycloalkylene group; Ar3 to Ar5 each independently represent 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, or -N(Ar 11 )(Ar 12 );and Ar 11 and Ar 12 each independently represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group; Provided that, in Formula 2, excluding the case where all of L3 to L5 are single bonds and all of Ar3 to Ar5 are hydrogen, in, X1 to X3 each independently represent N or CR 11 ; Provided that at least one of X1 to X3 is N; R 11 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 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, or a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; L7 to L9 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group; Ar7 to Ar9 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted tri(C1-C30) alkylsilyl group, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30) arylsilyl group, or -L 21 -N(Ar 21 )(Ar 22 ); L 21 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and Ar 21 and Ar 22 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group.
4. The organic electroluminescent device according to claim 3, wherein: At least one of Ar3 to Ar5 in Formula 2 is represented by any one of the following Formulas 2-1 to 2-3: in X1 and Y1 each independently represent -N=, -NR 25 -, -O-, or -S-; provided that either one of X1 and Y1 is -N=, and the other of X1 and Y1 is -NR 25 -, -O-, or -S-; R 21 represents a connection position to L3 to L5 in Formula 2, or a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group; R 22 To R 25 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 (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) aryl Silyl, 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, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to adjacent substituents to form one or more rings; a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 3; And when a to c are integers of 2 or more, each R 22 To each R 24 can be the same as or different from one another; * indicates the connection position to L3 to L5 in Formula 2; in Y represents -O-, -S-, or -NR 39 ; R 39 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and R 31 To R 38 Each independently represents a connection position to L3 to L5 in Formula 2; or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C 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, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to adjacent substituents to form one or more rings; in T stands for -O-, -S-, -CR 45 R 46 、-NR 47 , or -Se-; R 45 To R 47 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; R 41 To R 44 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -N(Ar 21 )(Ar 22 ) or may be connected to adjacent substituents to form one or more rings; Ar 21 and Ar 22 each independently represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group; d and g each independently represent an integer of 1 to 4, and e and f each independently represent 1 or integer of 2; When d to g are integers of 2 or more, each R 41 To each R 44 may be the same as or different from each other; and * indicates the connection position to L3 to L5 in Formula 2.
5. The organic electroluminescent device according to claim 3, wherein: At least one of Ar7 to Ar9 in Formula 3 is represented by any one of the following Formulas 2-2, 3-1, and 3-2: in Y represents -O-, -S-, or -NR 39 ; R 39 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and R 31 To R 38 Each independently represents a connection position to L7 to L9 in Formula 3; or 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(C 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, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to adjacent substituents to form one or more rings; in R 51 To R 64 Each independently represents a connection position to L7 to L9 in Formula 3; or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted tri(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted substituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, 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.
6. The organic electroluminescent device according to claim 1, wherein: The compound represented by Formula 1 is selected from the following compounds:
7. The organic electroluminescent device according to claim 3, wherein: The compound represented by Formula 2 is selected from the following compounds: In the above compounds, D n It means that n number of hydrogens are replaced by deuterium, wherein n is an integer of 1 or more, and the upper limit of n is determined according to the number of hydrogens that can be replaced in each compound.
8. The organic electroluminescent device according to claim 3, wherein: The compound represented by Formula 3 is selected from the following compounds: In the above compounds, D n It means that n number of hydrogens are replaced by deuterium, wherein n is an integer of 1 or more, and the upper limit of n is determined according to the number of hydrogens that can be replaced in each compound.
9. An organic electroluminescent compound, which is represented by the following formula 1-1: in R1 to R 10 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) )heteroaryl, 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, or *-L1-N(Ar1)(Ar2); provided that R1 to R 10 At least one of them is *-L1-N(Ar1)(Ar2); L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Provided that if R1, R2, R4, R5, R8, or R9 is *-L1-N(Ar1)(Ar2), then the following conditions are met: (1) If R5 or R8 is *-L1-N(Ar1)(Ar2), at least one of Ar1 and Ar2 is unsubstituted or deuterium-substituted phenyl; (2) if R1 or R2 is *-L1-N(Ar1)(Ar2), at least one of Ar1 and Ar2 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group; or both Ar1 and Ar2 are substituted or unsubstituted (3- to 30-membered) heteroaryl groups; and (3) If R4 or R9 is *-L1-N(Ar1)(Ar2), then Ar1 and Ar2 are both substituted or unsubstituted (3- to 30-membered) heteroaryl groups; or at least one of Ar1 and Ar2 is a substituted or unsubstituted carbazolyl group.
10. The organic electroluminescent compound according to claim 9, wherein The organic electroluminescent compound represented by Formula 1-1 is selected from the following compounds: 11 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 9 .
12. An organic electroluminescent compound represented by the following formula 3': in X1 to X3 each independently represent N or CR 11 ; Provided that at least one of X1 to X3 is N; R 11 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 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, or a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; L7 to L9 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group; and Ar7 to Ar9 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted tri(C1-C30) alkylsilyl group, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30) arylsilyl group, or -L 21 -N(Ar 21 )(Ar 22 ); Provided that at least one of Ar7 to Ar9 is of formula 2-2; in, Y represents -O- or -S-; and R 31 To R 38 Each independently represents a connection position to L7 to L9 in Formula 3; or 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(C 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, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to adjacent substituents to form one or more rings; Provided that if one of L7 to L9 is a phenylene group which is unsubstituted or substituted by deuterium or cyano, at least one of Ar7 to Ar9 is a binaphthyl group which is unsubstituted or substituted by deuterium or cyano, and if one of L7 to L9 is a naphthylene group which is unsubstituted or substituted by deuterium or cyano, at least one of Ar7 to Ar9 is a phenylnaphthyl group which is unsubstituted or substituted by deuterium or cyano.
13. The organic electroluminescent compound according to claim 12, wherein The organic electroluminescent compound represented by formula 3' is selected from the following compounds: In the above compounds, D n It means that n number of hydrogens are replaced by deuterium, wherein n is an integer of 1 or more, and the upper limit of n is determined according to the number of hydrogens that can be replaced in each compound.
14. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 12.
Citation Information
Patent Citations
Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
KR102306966B1
Electroactive materials
US20170025609A1