CN117720529A - Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same - Google Patents
Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Download PDFInfo
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- CN117720529A CN117720529A CN202311022511.9A CN202311022511A CN117720529A CN 117720529 A CN117720529 A CN 117720529A CN 202311022511 A CN202311022511 A CN 202311022511A CN 117720529 A CN117720529 A CN 117720529A
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- organic electroluminescent
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same. By including a specific combination of host compounds and/or organic electroluminescent compounds according to the present disclosure as an organic electroluminescent material, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long life characteristics can be provided.
Description
Technical Field
The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same.
Background
The TPD/Alq composed of a light-emitting layer and a charge-transporting layer was first developed by Tang et al from Eastman Kodak, 1987 3 Since a double-layer low-molecular green organic electroluminescent device (OLED), research on the organic electroluminescent device has been rapidly conducted and commercialization has been now achieved. Currently, organic electroluminescent devices mainly use phosphorescent materials having excellent luminous efficiency in panel realization. For long-term use and high resolution displays, OLEDs with high luminous efficiency and/or long lifetime are required.
In order to improve the light emitting efficiency, the driving voltage and/or the lifetime, various materials or concepts for the organic layer of the organic electroluminescent device have been proposed, but they are not satisfactory in practical use. Accordingly, there is a continuing need to develop an organic electroluminescent device having more improved performance, such as improved driving voltage, luminous efficiency, power efficiency, and/or lifetime characteristics, compared to previously disclosed organic electroluminescent devices.
KR 2016-0078218A discloses an organic light emitting device comprising an organic selenium compound as a host material; CN 111333611A discloses examples of devices comprising amino-substituted dibenzoselenophene compounds as materials for electron blocking layers; KR 2021-0128363A discloses amino-substituted naphtho [1,2-b ] [1] benzoselenophene as a compound for a coating layer. However, the prior art document does not specifically disclose various host materials comprising a specific combination of the present disclosure, organic electroluminescent devices comprising a naphthoselenophene compound as a light-emitting layer material. There is still a need to develop organic electroluminescent materials to improve the performance of OLEDs.
Disclosure of Invention
Technical problem
The object of the present disclosure is, first, to provide various host materials capable of producing an organic electroluminescent device having high luminous efficiency and/or long life characteristics, and, next, to provide an organic electroluminescent compound having a novel structure suitable for use as an organic electroluminescent material. Further, it is another object of the present disclosure to provide an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long life characteristics by including a plurality of host materials having a specific combination of compounds and/or electroluminescent compounds according to the present disclosure.
Solution to the problem
As a result of intensive studies to solve the above technical problems, the present inventors have found that the above object can be achieved by a variety of host materials including at least one first host material represented by the following formula 1 and at least one second host material represented by the following formula 2, so as to complete the present invention.
In the formula (1) of the present invention,
x represents O, S, se, CR 13 R 14 Or NR 15 ；
R 11 And R is 12 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, or-SiR 16 R 17 R 18 ；
R 13 To R 18 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl;
L 2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
HAr represents a substituted or unsubstituted (3-to 30-membered) heteroaryl group containing at least one nitrogen atom;
a represents an integer of 1 to 4, and b represents an integer of 1 to 3;
when a and b are 2 or more, each R 11 And each R 12 May be the same or different;
in the formula (2) of the present invention,
R 1 to R 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or formula a below; provided that R 1 To R 10 At least one of which is of the formula a;
in the formula (a) of the formula (a),
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;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-L 3 -NAr 3 Ar 4 ；
L 3 Represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 3 And Ar is a group 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
The beneficial effects of the invention are that
By using various host materials and/or organic electroluminescent compounds according to the present disclosure, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long life characteristics can be provided.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention and is not meant to limit the scope of the invention in any way.
The present disclosure relates to a plurality of host materials including a first host material including at least one compound represented by formula 1 and a second host material including at least one compound represented by formula 2, and an organic electroluminescent device including the same.
The present disclosure relates to an organic electroluminescent compound represented by formula 3, an organic electroluminescent material including the same, and an organic electroluminescent device.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any material layer constituting the organic electroluminescent device if necessary.
Herein, the term "organic electroluminescent material" means a material that may be used in an organic electroluminescent device and may comprise at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
The term "plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material comprising a combination of at least two compounds, which may be contained in any layer constituting an organic electroluminescent device. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Such at least two compounds may be contained in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.
Herein, the term "multiple host materials" means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. The various host materials of the present disclosure may be included in any light emitting layer constituting an organic electroluminescent device. At least two compounds contained in a plurality of host materials may be contained together in one light-emitting layer, or may be contained in separate light-emitting layers each. When at least two compounds are contained in one light-emitting layer, the at least two compounds may be mixed-evaporated to form a layer, or may be co-evaporated singly and simultaneously to form a layer.
Herein, "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. Herein, the term "(C3-C30) cycloalkyl" means a mono-or polycyclic hydrocarbon having from 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably from 3 to 20, and more preferably from 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. Herein, "(3-to 7-membered) heterocycloalkyl By "group" is meant a cycloalkyl group having 3 to 7 ring backbone atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, si and P, preferably O, S and N, wherein the number of ring backbone carbon atoms is preferably 5 to 7, such as tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiopane), tetrahydropyran, and the like. Herein, "(C6-C30) (arylene)" is a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure. Examples of aryl groups are in particular phenyl, biphenyl, terphenyl, tetrabiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthracenyl, benzanthrenyl, indenyl, triphenylenyl, pyrenyl, naphthacene, perylenyl,Radical, benzo->Radicals, naphthaceneyl (napthoxyl), fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro [ fluorene-fluorene ] ]Base, spiro [ fluorene-benzofluorene ]]A group, azulenyl (azulenyl), tetramethyl-dihydrophenanthryl, 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-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-tetraphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-Dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl, and 9, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1->Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt >Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11-dimethyl-1-benzo [ a ]]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ]]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethylPhenyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ]]Fluorenyl, 11-dimethyl-4-benzo [ c ] ]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl, 11-dimethyl-7-benzo [ c ]]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ]]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ]]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzo [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ]]Fluorenyl, 11-diphenyl-3-benzo [ c ] ]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl, 11-diphenyl-6-benzo [ c ]]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ]]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-2-phenanthryl 9, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like. Herein, "(3-to 30-membered) (ene) heteroaryl" is an aryl group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, si, P, se and Ge, wherein the number of ring backbone carbon atoms is preferably 3 to 30, and more preferably 5 to 20. The above (sub) heteroaromatic compoundsThe groups may be monocyclic or fused rings condensed with at least one benzene ring; and may be partially saturated. Further, the heteroaryl or heteroarylene described above herein may be a heteroaryl or heteroarylene formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds, and may comprise a spiro structure. Examples of heteroaryl groups may specifically be monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like; and a fused-ring type heteroaryl group, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzobenzofuranoquinolinyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthofuranopyrimidinyl, benzothiophenoquinolinyl, benzothiophenoquinazolinyl, benzoquinolinyl, benzopyrimidinyl, benzoquinolinyl, and benzoquinolinyl benzothiophene naphthyridinyl, benzothiophene pyrimidinyl, naphthyridin pyrimidinyl, pyrimidoindolyl, benzopyrimidino indolyl, benzofuranopyrazinyl, naphtofuranopyrazinyl, benzothiophenopyrazinyl, naphthyridin opyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzofuranpyrazinyl, benzofuranyl, benzoimidazolyl, benzoyl, benzoimidazolyl benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolicidinyl (indozidinyl), acridinyl, silafluorenyl (silafluoronyl), germofluorenyl (germofluorenyl), benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenyl, dimethylphenyl, indolocarbazolyl, indenocarbazolyl, and the like. More specifically, the heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-azoxystrobin 1,2, 4-triazin-4-yl, 1,2, 4-triazin-3-yl, 1,3, 5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolicidinyl, 2-indolicidinyl, 3-indolicidinyl, 5-indolicidinyl, 6-indolicidinyl, 7-indolicidinyl, 8-indolicidinyl, 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-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 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-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-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]Benzothia (E) -benzothia (E)Phenoyl, 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, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl, 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. Herein, the term "(C3-C30) aliphatic ring and fused ring of (C6-C30) aromatic ring" means a ring formed by fusing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms and at least one aromatic ring having 6 to 30 ring skeleton carbon atoms, the number of carbon atoms in the aliphatic ring being preferably 3 to 25, more preferably 3 to 18, and the number of carbon atoms in the aromatic ring being preferably 6 to 25, more preferably 6 to 18. For example, the condensed ring may be a condensed ring of at least one benzene and at least one cyclohexane, or a condensed ring of at least one naphthalene and at least one cyclopentane, or the like. Herein, the carbon atoms in the fused rings of the (C3-C30) aliphatic ring and the (C6-C30) aromatic ring may 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 term "halogen" in this disclosure includes F, cl, br and I.
Further, "o", "m", and "p" mean substitution positions of all substituents. Ortho-positions are compounds having substituents adjacent to each other, for example at positions 1 and 2 on benzene. Meta is the next substitution position to the immediately adjacent substitution position, e.g., the compound has substituents at positions 1 and 3 on benzene. Para is the next substitution position in the meta position, e.g., the compound has substituents at positions 1 and 4 on benzene.
Herein, the term "ring formed by attachment to adjacent substituents" means a substituted or unsubstituted (3-to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by attachment or fusion of two or more adjacent substituents, preferably a substituted or unsubstituted (5-to 25-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. Furthermore, the ring formed may comprise at least one heteroatom selected from the group consisting of B, N, O, S, si and P, preferably N, O and S. According to one embodiment of the present disclosure, the number of atoms in the ring backbone is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring backbone is 5 to 15. In one embodiment, the fused ring may be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzofluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, or the like.
Further, the expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or functional group (i.e., substituent), and is substituted with a group to which two or more substituents are attached among the substituents. For example, "a substituent in which two or more substituents are linked" may be pyridine-triazine. That is, the pyridine-triazine may be a heteroaryl group, or may be interpreted as one substituent in which two heteroaryl groups are linked. Preferably, in the formulas of the present disclosure, the substituents of the substituted alkyl group, the substituted alkenyl group, the substituted aryl (ene) group, the substituted heteroaryl (ene) group, the substituted phenyl group, the substituted naphthyl (ene) group, the substituted biphenyl group, the substituted terphenyl group, the substituted dibenzofuranyl group, the substituted dibenzothienyl group, and the substituted carbazolyl group each independently represent at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (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 deuterium-substituted (3-to 30-membered) heteroaryl; (C6-C30) aryl, unsubstituted or substituted with deuterium; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; amino, mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (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; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. For example, the substituent of the above substituted compound may be deuterium, methyl, phenyl, naphthyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl, m-terphenyl, triphenylene, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, and the like.
Hereinafter, a plurality of host materials according to one embodiment will be described.
The plurality of host materials according to one embodiment are a plurality of host materials including at least one first host material and at least one second host material, wherein the first host material is a compound represented by formula 1 and the second host material is a compound represented by formula 2. According to one embodiment, a plurality of host materials may be included in a light emitting layer of an organic electroluminescent device.
According to one embodiment, a first host material as a host material is represented by the following formula 1.
In the formula (1) of the present invention,
x represents O, S, se, CR 13 R 14 Or NR 15 ；
R 11 And R is 12 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, or-SiR 16 R 17 R 18 ；
R 13 To R 18 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl;
L 2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
HAr represents a substituted or unsubstituted (3-to 30-membered) heteroaryl group containing at least one nitrogen atom;
a represents an integer of 1 to 4, and b represents an integer of 1 to 3;
when a and b are 2 or more, each R 11 And each R 12 May be the same or different.
In one embodiment, X may be O, S or Se.
In one embodiment, R 11 And R is 12 Each independently can be hydrogen, deuterium, 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-membered)To 25 membered) heteroaryl, more preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-to 18-membered) heteroaryl. For example, R 11 And R is 12 Each independently may be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted benzothiophenocarbazolyl. For example, the substituent of the above substituted compound may be a phenyl group.
In one embodiment, L 2 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 2 May be a single bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted naphthylene.
In one embodiment, the HAr may be a substituted or unsubstituted (5-to 30-membered) heteroaryl group containing at least one nitrogen atom, preferably a substituted or unsubstituted (5-to 30-membered) heteroaryl group containing at least two nitrogen atoms, more preferably a substituted or unsubstituted (5-to 30-membered) heteroaryl group containing at least three nitrogen atoms. For example, HAr may be a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothiophenopyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted pyridopyrazinyl group. Wherein the substituent of the above substituted compound may be a (C6-C30) aryl group which is unsubstituted or substituted with at least one of deuterium, a tri (C6-C30) arylsilyl group, and a (3-to 30-membered) heteroaryl group, or a (3-to 30-membered) heteroaryl group which is unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group. For example, the substituent of the above substituted compound may be at least one of the following: phenyl which is unsubstituted or substituted with at least one of deuterium, naphthyl, dibenzofuranyl, carbazolyl, and triphenylsilyl, naphthyl which is unsubstituted or substituted with phenyl, p-biphenyl which is substituted or unsubstituted, m-biphenyl which is substituted or unsubstituted, o-biphenyl which is substituted or unsubstituted, p-terphenyl which is substituted or unsubstituted, m-terphenyl which is substituted or unsubstituted, triphenylene which is substituted or unsubstituted, diphenylfluorenyl which is substituted or unsubstituted, spirodibenzofluorenyl which is substituted or unsubstituted, dibenzofuranyl which is substituted or unsubstituted with at least one of deuterium and phenyl, dibenzothiophenyl which is unsubstituted or substituted with at least one of deuterium, and benzocarbazolyl which is substituted or unsubstituted, preferably, the substituent of the above-mentioned substituted compound may be further substituted with at least one of deuterium.
According to one embodiment, the host material represented by formula 1 may be represented by the following formula 1-a.
In the formula (1-A),
x represents as defined in formula 1;
R 19 to R 26 Each independently represents hydrogen, deuterium, a (C6-C18) aryl group which is unsubstituted or substituted with at least one of deuterium, (C1-C6) alkyl group, and (C6-C18) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or the following formula 1-a; provided that R 19 To R 26 At least one of which is of the following formula 1-a;
in the formula (1-a),
L 4 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;
X 1 to X 3 Each independently represents CR or N; provided that X 1 To X 3 At least two of which are N; and is also provided with
Ar a And Ar is a group b Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In one embodiment, L 4 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 4 May be a single bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted naphthylene.
In one embodiment, ar a And Ar is a group b Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group A group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a combination thereof.
According to one embodiment, the host material represented by formula 1 may be represented by the following formula 1-1.
In the case of the formula 1-1,
X、R 11 、R 12 、L 2 a and b are as defined in formula 1;
X' 1 to X' 3 Each independently represents CR' or N; provided that X' 1 To X' 3 At least two of which are N;
r' represents hydrogen or deuterium; and is also provided with
Ar a And Ar is a group b Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In one embodiment, X' 1 To X' 3 May be N.
In one embodiment, L 2 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 2 May be a single bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted naphthylene.
In one embodiment, ar a And Ar is a group b Each independently may be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group, more preferably a (C6-C25) aryl group, which is unsubstituted or substituted with at least one of deuterium, tri (C6-C30) arylsilyl, and a (3-to 30-membered) heteroaryl group, or a (5-to 18-membered) heteroaryl group, which is unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl group. For example, ar a And Ar is a group b Each independently may be: phenyl unsubstituted or substituted with at least one of deuterium, naphthyl, dibenzofuranyl, carbazolyl, and triphenylsilyl, naphthyl unsubstituted or substituted with phenyl, p-biphenyl unsubstituted or substituted with phenyl, m-biphenyl unsubstituted or substituted with o-biphenyl, p-terphenyl unsubstituted or substituted with m-terphenyl, triphenylene unsubstituted or substituted with triphenylfluorenyl, spirodibenzofluorenyl unsubstituted or substituted with at least one of deuterium and phenyl, dibenzothienyl unsubstituted or substituted with at least one of deuterium, carbazolyl unsubstituted or substituted with at least one of deuterium and phenyl, or a substituted with at least one of deuteriumThe substituted or unsubstituted benzocarbazolyl group, preferably, the substituent of the above substituted compound may be further substituted with at least one deuterium.
According to one embodiment, the compound represented by formula 1-1 may be represented by any one of the following formulas 1-1-1 to 1-1-4.
In the formulae 1-1-1 to 1-1-4, X, X' 1 To X' 3 、R 11 、R 12 、L 2 、Ar a 、Ar b A and b are as defined in formula 1-1.
According to one embodiment, the first host material represented by formula 1 may be more specifically described by the following compounds, but is not limited thereto.
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The host material having formula 1 according to the present disclosure may be prepared by the following reaction scheme 1 or 2, but is not limited thereto, and may be produced by synthetic methods known to those skilled in the art.
Reaction scheme 1
Reaction scheme 2
In reaction schemes 1 and 2, the definition of each substituent is as defined in formula 1, and Hal means a halogen atom.
As mentioned above, illustrative synthetic examples of the compounds represented by formula 1 are described, but they are based on Buchwald-Hartmax (Buchwald-Hartwig) cross-coupling reaction, bell wood (Suzuki) cross-coupling reaction, wittig reaction, miyaura boronation reaction, N-arylation reaction, acidified montmorillonite (H-mont) mediated etherification reaction, intramolecular acid induced cyclization reaction, pd (II) catalyzed oxidative cyclization reaction, grignard reaction, heck (Heck) reaction, dehydrative cyclization reaction, SN 1 Substitution reaction, SN 2 Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like. Those skilled in the art will appreciate that the above reaction proceeds even if other substituents defined in formula 1 are bonded in addition to the substituents described in the specific synthetic examples.
According to one embodiment, the second host material as another host material is represented by the following formula 2.
In the formula (2) of the present invention,
R 1 to R 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or formula a below; provided that R 1 To R 10 At least one of which is of the formula a;
in the formula (a) of the formula (a),
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;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-L 3 -NAr 3 Ar 4 ；
L 3 Represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 3 And Ar is a group 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In one embodiment, R 1 To R 10 Each independently can be hydrogen, deuterium, or formula a, and R 1 To R 10 At least one of which is of formula a.
In one embodiment, R 1 To R 10 At least two of which may be formula a.
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 p-biphenylene group, a substituted or unsubstituted m-biphenylene group, or a substituted or unsubstituted o-biphenylene group.
In one embodiment, ar 1 And Ar is a group 2 Each independently may be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group, more preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 18-membered) heteroaryl group. For example, ar 1 And Ar is a group 2 Each independently can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted antithetical coupletPhenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-tetraphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, unsubstituted or methyl-substituted benzofluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothienyl. Wherein the substituent of the above-mentioned substituted compound may be at least one of methyl, phenyl, fluorenyl, and carbazolyl.
In one embodiment, L 3 May be a substituted or unsubstituted (C6-C30) arylene group, preferably a substituted or unsubstituted (C6-C25) arylene group, more preferably a substituted or unsubstituted (C6-C18) arylene group. For example, L 3 May be a substituted or unsubstituted phenylene group.
In one embodiment, ar 3 And Ar is a group 4 Each independently may be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 18-membered) heteroaryl group. For example, ar 3 And Ar is a group 4 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group. Wherein the substituent of the above-mentioned substituted compound may be at least one of methyl, phenyl, and diphenylamino.
According to one embodiment, the host material represented by formula 2 may be represented by the following formula 2-1 or 2-2.
In formulas 2-1 and 2-2,
R 1 to R 10 、L 1 、Ar 1 And Ar 2 As defined in equation 2.
According to one embodiment, the second host material represented by formula 2 may be more specifically described by the following compounds, but is not limited thereto.
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The host material having formula 2 according to the present disclosure may be produced by synthetic methods known to those skilled in the art.
According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by the following formula 3.
In the case of the method of 3,
R 27 to R 36 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or formula b below; provided that R 27 To R 36 At least one of which is of the formula b;
in the formula b of the formula (b),
y represents O, S, CR 37 R 38 Or NR (NR) 39 ；
R 37 To R 39 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group;
L 3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 3 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
Hereinafter, an organic electroluminescent device to which the above-described various host materials and/or organic electroluminescent compounds are applied will be described.
According to one embodiment, an organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode. The organic layer may include a light emitting layer, and the light emitting layer may include a plurality of host materials including at least one first host material represented by formula 1 and at least one second host material represented by formula 2.
According to another embodiment, the light emitting layer may include an organic electroluminescent compound represented by formula 3.
According to one embodiment, the organic electroluminescent material of the present disclosure comprises at least one of compounds H1-1 to H1-392 as a first host material and at least one of compounds H2-1 to H2-333 as a second host material. The plurality of host materials may be contained in the same organic layer, for example, the same light-emitting layer, or may be contained in different light-emitting layers, respectively.
According to another embodiment, the organic electroluminescent material of the present disclosure comprises the organic electroluminescent compound represented by formula 3, alone or in combination of two or more. Such an organic electroluminescent material is contained in an organic layer of an organic electroluminescent device such as a light emitting layer or a hole transporting layer.
The organic layer may further include at least one layer selected from the group consisting of: a hole injection layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. In addition to the luminescent material according to the present disclosure, the organic layer may further comprise an amine-based compound and/or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emitting auxiliary layer, or the electron blocking layer may contain an amine-based compound (for example, an arylamine-based compound, a styrylarylamine-based compound, or the like) as a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, or an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, or the hole blocking layer may contain an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, or a hole blocking material. In addition, the organic layer may further comprise at least one metal selected from the group consisting of: a metal of group 1 of the periodic table, a metal of group 2, a transition metal of group 4, a transition metal of group 5, an organometallic of a lanthanide and a d-transition element, or at least one complex compound comprising such a metal.
According to one embodiment, a variety of host materials may be used as the light emitting material for the white organic light emitting device. Depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light emitting units, a white organic light emitting device has proposed various structures such as a parallel side-by-side arrangement method, a stacked arrangement method, or a CCM (color conversion material) method, or the like. Furthermore, according to one embodiment, a variety of host materials may also be applied to an organic electroluminescent device including QDs (quantum dots).
One of the first electrode and the second electrode may be an anode, and the other may be a cathode. Wherein the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a two-side emission type according to the kind of material forming the first and second electrodes.
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 a multilayer to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer may use two compounds at the same time. In addition, the hole injection layer may be doped with a p-type dopant. Further, an electron blocking layer may be disposed between the hole transporting layer (or hole injecting layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing from the light emitting layer to prevent light emission leakage. The hole transporting layer or the electron blocking layer may be a multilayer, and various compounds may be used for each layer.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be a plurality of layers to control injection of electrons and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the plurality of layers may use two compounds at the same time. A 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 transporting layer may also be a multilayer, wherein each layer may use a plurality of compounds. In addition, the electron injection layer may be doped with an n-type dopant.
The light emitting auxiliary layer may be 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 promote hole injection and/or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to promote electron injection and/or electron transport, or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and the hole transport rate (or hole injection rate) may be effectively promoted or limited, thereby enabling control of charge balance. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer may serve as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving efficiency and/or lifetime of the organic electroluminescent device.
In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a halogenated metal layer, and a metal oxide layer may be preferably placed on an inner surface of one or both of a pair of electrodes. In particular, it is preferable to place a layer of chalcogenides (including oxides) of silicon and aluminum on the anode surface of the electroluminescent medium layer, and to place a layer of a metal halide or metal oxide on the cathode surface of the electroluminescent medium layer. The operational stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide comprises SiO X (1≤X≤2)、AlO X (X is more than or equal to 1 and less than or equal to 1.5), siON, siAlON and the like; the halogenated metal comprises LiF, mgF 2 、CaF 2 Rare earth metal fluorides, etc.; and the metal oxide includes Cs 2 O、Li 2 O, mgO, srO, baO, caO, etc.
Further, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transporting compound and a reducing dopant, or a mixed region of a hole transporting compound and an oxidizing dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus injection and transport of electrons from the mixing region to the electroluminescent medium becomes easier. Furthermore, the hole transporting compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the electroluminescent medium become easier. Preferably, the oxidizing dopants include various lewis acids and acceptor compounds, and the reducing dopants include 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 prepare an organic electroluminescent device having two or more light emitting layers and emitting white light.
The organic electroluminescent device according to one embodiment may further include one or more dopants in the light emitting layer.
The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or a 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 metallized complex compounds of one or more metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more orthometalated complex compounds of one or more metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably is one or more orthometalated iridium complex compounds.
The dopant included in the organic electroluminescent device of the present disclosure may use a compound represented by the following formula 101, but is not limited thereto.
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In the case of the method 101,
l is selected from any one of the following structures 1 to 3;
wherein,
R 100 to R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or R is 100 To R 103 May be attached to adjacent substituents to form one or more rings, for example with benzene to form one or more rings, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothiophenopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothiophenoquinoline, or substituted or unsubstituted indenoquinoline;
R 104 to R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or R is 104 To R 107 May be attached to adjacent substituents to form one or more substituted or unsubstituted rings, for example, with benzene to form one or more substituted or unsubstituted rings, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothiophenopyridine;
R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or R is 201 To R 220 May be attached to one or more adjacent substituents to form one or more substituted or unsubstituted rings; and is also provided with
s represents an integer of 1 to 3.
In particular, specific examples of the dopant compound include the following, but are not limited thereto.
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In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as spin coating, dip coating, flow coating method, or the like may be used. When a wet film forming method is used, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and which has no problem in terms of film forming ability.
When forming a layer by the first host material and the second host material according to one embodiment, the layer may be formed by the methods listed above, and may generally be formed by co-deposition or hybrid deposition. Co-deposition is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and an electric current is applied to both chambers simultaneously to evaporate the materials; and hybrid deposition is a method in which two or more materials are mixed in one crucible source before they are deposited and then an electric current is applied to one cell to evaporate the materials.
According to one embodiment, when the first host material and the second host material are present in the same layer or different layers in the organic electroluminescent device, the layers may be formed separately from the two host compounds. For example, after depositing the first host material, a second host material may be deposited.
According to one embodiment, the present disclosure may provide a display device including a plurality of host materials including a first host material represented by formula 1 and a second host material represented by formula 2. Further, by using the organic electroluminescent device of the present disclosure, a display device such as a smart phone, a tablet computer, a notebook computer, a PC, a TV, or a display device for a vehicle, or a lighting device such as outdoor or indoor lighting may be prepared.
Hereinafter, a preparation method of a host material according to the present disclosure will be explained with reference to a synthesis method of a representative compound or an intermediate compound in order to understand the present disclosure in detail.
EXAMPLE 1 Synthesis of Compound H2-15
Compounds 1-1 (5 g,15.84 mmol), 1-2 (5.3 g,15.99 mmol), tris (dibenzylideneacetone) dipalladium (Pd) 2 dba 3 ) (0.72 g,0.79 mmol), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (S-Phos) (0.65 g,1.58 mmol), sodium t-butoxide (NaOtBu) (3.8 g,39.6 mmol), and 80mL of toluene were added to the flask and dissolved, followed by stirring under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and filtered through silica, followed by drying. Thereafter, it was separated by column chromatography to obtain compound H2-15 (9.2 g, yield: 95%).
| MW | Melting point | |
| H2-15 | 614.6 | 351℃ |
EXAMPLE 2 Synthesis of Compound H2-23
Compound 1-1 (5 g,15.84 mmol), compound 2-1 (5.8 g,15.99 mmol), pd 2 dba 3 (0.72 g,0.79 mmol), S-Phos (0.65 g,1.58 mmol), naOtBu (3.8 g,39.6 mmol), and 80mL of toluene were added to the flask and dissolved, followed by stirring under reflux for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and filtered through silica, followed by drying. Thereafter, it was separated by column chromatography to obtain compound H2-23 (9.8 g, yield: 96%).
| MW | Melting point | |
| H2-23 | 640.7 | 365℃ |
EXAMPLE 3 Synthesis of Compound H2-88
Compound 3-1 (5 g,15.84 mmol), compound 1-2 (5.3 g,15.99 mmol), pd 2 dba 3 (0.72g，0.79mmol)、SPhos (0.65 g,1.58 mmol), naOtBu (3.8 g,39.6 mmol), and 80mL of toluene were added to the flask and dissolved, followed by stirring at reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and filtered through silica, followed by drying. Thereafter, it was separated by column chromatography to obtain compound H2-88 (8.6 g, yield: 88%).
| MW | Melting point | |
| H2-88 | 614.6 | 174℃ |
EXAMPLE 4 Synthesis of Compound H2-73
Compound 3-1 (5 g,15.84 mmol), compound 2-1 (5.8 g,15.99 mmol), pd 2 dba 3 (0.72 g,0.79 mmol), S-Phos (0.65 g,1.58 mmol), naOtBu (3.8 g,39.6 mmol), and 80mL of toluene were added to the flask and dissolved, followed by stirring under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and filtered through silica, followed by drying. After that, it was separated by column chromatography to obtain compound H2-73 (8.4 g, yield: 83%).
| MW | Melting point | |
| H2-73 | 640.7 | 176℃ |
Hereinafter, a method of manufacturing an organic electroluminescent device including various host materials and/or organic electroluminescent compounds according to the present disclosure and device characteristics thereof will be explained in order to understand the present disclosure in detail.
Device examples 1 to 5 preparation of OLEDs by co-deposition of a first host material and a second host material according to the present disclosure
An OLED according to the present disclosure was produced. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (Ji Aoma limited (GEOMATEC co., ltd.), japan) on a glass substrate for OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, and thereafter stored in isopropyl alcohol and then used. Thereafter, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, the compound HI-1 was introduced into one cell of the vacuum vapor deposition apparatus, and the compound HT-1 was introduced into the other cell. The two materials were evaporated at different rates and compound HI-1 was deposited with a doping amount of 3wt% based on the total of compounds HI-1 and HT-1 to form an implanted layer with a thickness of 10 nm. Next, the compound HT-1 was deposited on the hole injection layer as a first hole transport layer having a thickness of 80 nm. Then introducing the compound HT-2 into another cell of the vacuum vapor deposition apparatus, and evaporating the compound by applying a current to the cell to form a film having 60n on the first hole transport layer And a second hole transport layer of m thickness. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the first host material and the second host material described in table 1 below were introduced as hosts into two cells of a vacuum vapor deposition apparatus, respectively, and the compound D-39 was introduced as a dopant into the other cell. The two host materials were evaporated at a rate of 1:1, and the dopant materials were simultaneously evaporated at different rates and deposited at a doping amount of 3wt% based on the total amount of host and dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Next, the compounds ET-1 and EI-1 were deposited as an electron transport material in a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound to be used for all materials was found to be at 10 -6 Purification by vacuum sublimation was performed under the tray.
Device comparative example 1 preparation of OLED comprising comparative compound as host
An OLED was fabricated in the same manner as in device example 1, except that the host compound described in table 1 below was used as the second host material of the light-emitting layer.
The driving voltage, the light emitting efficiency and the light emitting color of the OLEDs of the device examples 1 to 5 and the device comparative example 1 produced as described above at a luminance of 1,000 nit, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nit (lifetime: T95) were measured, and the results thereof are shown in table 1 below.
TABLE 1
From the results shown in table 1 above, it can be confirmed that the organic electroluminescent device using the organic electroluminescent compound according to the present invention as various host materials shows low driving voltage and high luminous efficiency, as well as long life characteristics, compared to the organic electroluminescent device using the conventional host compound.
The compounds used in device examples 1 to 5 and device comparative example 1 are specifically shown in table 2 below.
TABLE 2
Device examples 6 to 10 preparation of OLEDs by deposition of compounds according to the present disclosure as hole transport materials
An OLED according to the present disclosure was produced. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (Ji Aoma limited, japan) on a glass substrate for OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, and thereafter stored in isopropyl alcohol and then used. Thereafter, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, the compound HI-1 was introduced into one cell of the vacuum vapor deposition apparatus, and the compound HT-3 was introduced into the other cell. The two materials were evaporated at different rates and compound HI-1 was deposited with a doping amount of 3wt% based on the total of compounds HI-1 and HT-3 to form an implanted layer with a thickness of 10 nm. Next, the compound HT-3 was deposited on the hole injection layer as a first hole transport layer having a thickness of 80 nm. Next, the compound described in table 3 below was then introduced into another cell of the vacuum vapor deposition apparatus as a material for the second hole transport layer, and the compound was evaporated by applying a current to the cell, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: compounds H1-382 and B1 were introduced as host materials into two cells of a vacuum vapor deposition apparatus, respectively, as a host, and compound D-39 was introduced into the other cell as a dopant. The two host materials were evaporated at a rate of 1:1, and the dopant materials were simultaneously evaporated at different rates and doped at 3wt% based on the total of host and dopant The deposition was performed in an amount to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Next, the compound HBL was deposited as an electron buffer layer of 5nm thickness on the light emitting layer, and then the compounds ET-2 and EI-1 were deposited as electron transport materials in a weight ratio of 50:50 to form an electron transport layer having a thickness of 30nm thereon. After the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound to be used for all materials was found to be at 10 -6 Purification by vacuum sublimation was performed under the tray.
Device comparative examples 2 and 3 preparation of OLED comprising comparative compound as hole transport material
An OLED was fabricated in the same manner as in device example 6, except that the compounds in table 3 below were used as the material for the second hole transport layer.
The driving voltage, power efficiency and emission color of the OLEDs of device examples 6 to 9 and device comparative examples 2 and 3 produced as described above at a luminance of 1,000 nit, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nit (lifetime: T95) were measured, and the results thereof are shown in table 3 below.
TABLE 3 Table 3
From the results shown in table 3 above, it can be confirmed that the organic electroluminescent device using the organic electroluminescent compound according to the present invention as a hole transport layer material shows low driving voltage and high power efficiency, and significantly improved long life characteristics, compared to the organic electroluminescent device comprising the conventional organic electroluminescent compound as a hole transport layer material.
The compounds used in device examples 6 to 9 and device comparative examples 2 and 3 are specifically shown in table 4 below.
TABLE 4 Table 4
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Claims (10)
1. A plurality of host materials comprising at least one first host material represented by the following formula 1 and at least one second host material represented by the following formula 2:
wherein,
x represents O, S, se, CR 13 R 14 Or NR 15 ；
R 11 And R is 12 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, or-SiR 16 R 17 R 18 ；
R 13 To R 18 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl;
L 2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
HAr represents a substituted or unsubstituted (3-to 30-membered) heteroaryl group containing at least one nitrogen atom;
a represents an integer of 1 to 4, and b represents an integer of 1 to 3;
when a and b are 2 or more, each R 11 And each R 12 May be the same or different;
wherein,
R 1 to R 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted(C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or formula a; provided that R 1 To R 10 At least one of which is of the formula a;
wherein,
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;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-L 3 -NAr 3 Ar 4 ；
L 3 Represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 3 And Ar is a group 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
2. The plurality of host materials of claim 1, wherein HAr having formula 1 represents a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothiophenyl pyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted pyridopyrazinyl group.
3. The plurality of host materials of claim 1, wherein the formula 1 is represented by the following formula 1-a:
wherein,
x represents as defined in claim 1;
R 19 to R 26 Each independently represents hydrogen, deuterium, a (C6-C18) aryl group which is unsubstituted or substituted with at least one of deuterium, (C1-C6) alkyl group, and (C6-C18) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or the following formula 1-a; provided that R 19 To R 26 At least one of which is of the following formula 1-a;
wherein,
L 4 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;
X 1 to X 3 Each independently represents CR or N; provided that X 1 To X 3 At least two of which are N; and is also provided with
Ar a And Ar is a group b Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
4. The plurality of host materials of claim 1, wherein the formula 2 is represented by the following formula 2-1 or 2-2:
wherein,
R 1 to R 10 、L 1 、Ar 1 And Ar 2 As defined in claim 1.
5. The plurality of host materials of claim 1, wherein Ar in formula 2 1 And Ar is a group 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-tetraphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, an unsubstituted or methyl-substituted benzofluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.
6. The plurality of host materials of claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
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7. the plurality of host materials of claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
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8. an organic electroluminescent compound represented by the following formula 3:
wherein,
R 27 to R 36 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or formula b below; provided that R 27 To R 36 At least one of which is of the formula b;
wherein,
y represents O, S, CR 37 R 38 Or NR (NR) 39 ；
R 37 To R 39 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group;
L 3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 3 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
9. An organic electroluminescent device comprising a plurality of host materials according to claim 1.
10. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 8.
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| KR1020230081810A KR20240039580A (en) | 2022-09-19 | 2023-06-26 | A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same |
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