CN111362947A - Benzimidazole-containing organic compound and application thereof - Google Patents
Benzimidazole-containing organic compound and application thereof Download PDFInfo
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- CN111362947A CN111362947A CN201811600930.5A CN201811600930A CN111362947A CN 111362947 A CN111362947 A CN 111362947A CN 201811600930 A CN201811600930 A CN 201811600930A CN 111362947 A CN111362947 A CN 111362947A
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 239000010410 layer Substances 0.000 claims description 66
- -1 dibenzofuranyl Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 10
- 241000720974 Protium Species 0.000 claims description 10
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052722 tritium Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000005551 pyridylene group Chemical group 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000006836 terphenylene group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 28
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 15
- 230000009477 glass transition Effects 0.000 abstract description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 4
- 238000005457 optimization Methods 0.000 abstract description 4
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- 239000000463 material Substances 0.000 description 84
- 239000007858 starting material Substances 0.000 description 38
- 239000000543 intermediate Substances 0.000 description 36
- 238000012360 testing method Methods 0.000 description 27
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- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Substances [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
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- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 150000001556 benzimidazoles Chemical class 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 2
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 2
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 2
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 2
- 102100024954 5-hydroxytryptamine receptor 3A Human genes 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 2
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101150017422 HTR1 gene Proteins 0.000 description 2
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
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- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
The invention discloses an organic compound containing benzimidazole and application thereof, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (I):
the invention also discloses a preparation method and application of the organic compound containing benzimidazole. The compound contains benzimidazole parent nucleus and arylamine derivative structure, has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
Description
Technical Field
The invention relates to an organic compound containing benzimidazole and application thereof, belonging to the technical field of semiconductors.
Background
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
An object of the present invention is to provide an organic compound containing benzimidazole. The compound contains benzimidazole derivatives and triarylamine derivatives, has higher glass transition temperature and molecular thermal stability and proper HOMO energy level, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme for solving the technical problems is as follows: an organic compound containing benzimidazole, the structure of the compound is shown as general formula (1):
in the general formula (1), L represents one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl and substituted or unsubstituted naphthylene;
Ar1、Ar2each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted 5-30 membered heteroarylene containing one or more heteroatoms;
R1、R2each independently represents substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
said substitutable groupThe substituents of the group are optionally selected from protium, deuterium, tritium, cyano, halogen, C1-20Alkyl radical, C6-30One or more of aryl and 5-30 membered heteroaryl;
the heteroatom is selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the invention, R is1、R2Each independently represents a substituted or substituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted pyrenyl group, a structure represented by the general formula (2) or the general formula (3);
said X1、X2、X3Each independently represents an oxygen atom, a sulfur atom, -C (R)3)(R4) -or-N (R)5) -, and X1、X3May also represent a single bond;
said L1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranylene group;
z represents a nitrogen atom or C (R)6) (ii) a Z at the attachment site is represented as a carbon atom;
the R is3～R5Are each independently represented by C1-10Alkyl, substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; wherein R is1And R2Can also be connected with each other to form a ring;
the R is6Represented by a hydrogen atom,Protium, deuterium, tritium, cyano, halogen atom, C1-10Alkyl radical, C2-10Alkylene, substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; two adjacent R6Can be connected with each other to form a ring;
the substituents which may be substituted are optionally selected from protium, deuterium, tritium, cyano, halogen, C1-20Alkyl radical, C2-20Alkenyl radical, C6-30One or more of aryl and 5-30 membered heteroaryl;
the heteroatom is selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the invention, Ar is1、Ar2Each independently represents one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolyl and substituted or unsubstituted naphthyridinylene;
the R is3～R5Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyridinyl;
the R is6Represented by a hydrogen atom, protium, deuterium, tritium, cyano group, fluorine atom, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted terphenylyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group;
the substituent of the substitutable group is one or more selected from protium, deuterium, tritium, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuryl, carbazolyl or pyridyl.
As a further improvement of the present invention, the specific structure of the compound is:
any one of the above.
Another object of the present invention is to provide a process for producing the above benzimidazole-containing organic compound. The preparation method is simple, has wide market prospect and is suitable for large-scale popularization and application.
The technical scheme for solving the technical problems is as follows: the preparation method of the organic compound containing benzimidazole relates to the following reaction equation:
the specific process of the reaction of equation 1-1 is: weighing the intermediate I and the raw material II, and dissolving the intermediate I and the raw material II by using toluene; then adding Pd2(dba)3、P(t-Bu)3Sodium tert-butoxide; reacting the mixed solution of the reactants at 95-110 ℃ for 10-24 hours under inert atmosphere, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain the target product; the molar ratio of the intermediate I to the amino compound is 1 (1.2-3.0), and Pd2(dba)3The molar ratio of the intermediate I to the tri-tert-butylphosphine is (0.006-0.02):1, the molar ratio of the tri-tert-butylphosphine to the intermediate I is (0.006-0.02):1, and the molar ratio of the sodium tert-butoxide to the intermediate I is (1.0-3.0): 1;
it is a further object of the present invention to provide an organic electroluminescent device. When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved, and the compound has good application effect and industrialization prospect.
The technical scheme for solving the technical problems is as follows: an organic electroluminescent element, at least one functional layer of which comprises the above benzimidazole-containing organic compound.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the functional layer is a hole transport layer and/or an electron blocking layer and/or a light emitting layer.
The fourth objective of the present invention is to provide an illumination or display device. The organic electroluminescent device can be applied to lighting or display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
The technical scheme for solving the technical problems is as follows: a lighting or display element includes the above organic electroluminescent device.
The invention has the beneficial effects that:
1. the compound of the invention takes benzimidazole derivatives as a framework and is connected with triarylamine derivative branched chains, and the structure has stronger rigidity, large steric hindrance and difficult rotation, so that the three-dimensional structure of the compound material of the invention is more stable. When the compound is used as a hole transport layer or an electron blocking material of an OLED, the hole transport can be effectively realized by the proper HOMO energy level; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, improves the recombination efficiency of excitons in the luminescent layer, reduces energy loss, and enables the energy of the main material of the luminescent layer to be fully transferred to the doping material, thereby improving the luminous efficiency of the material after being applied to a device.
2. The structure of the compound enables the distribution of electrons and holes in the luminescent layer to be more balanced, and under the proper HOMO energy level, the hole injection and transmission performance is improved; when the benzimidazole derivative serving as a light-emitting functional layer material of an OLED light-emitting device is used, the benzimidazole derivative serving as a parent nucleus of a framework and the branched chain within the range of the benzimidazole derivative can effectively improve the exciton utilization rate and the high fluorescence radiation efficiency, reduce the efficiency roll-off under high current density, reduce the voltage of the device, improve the current efficiency of the device and prolong the service life of the device.
3. The compound is subjected to ring merging design on a benzimidazole group, and after a substituent group is added, the Tg temperature of the material is raised, and an active C-H bond is passivated, so that the stability of the material is improved; the addition of the substituent group increases the molecular weight of the material, but in the practical application process, the evaporation temperature of the material is reduced, the temperature interval between the processing temperature and the decomposition temperature of the material is widened, and the use and processing window of the material is improved.
4. When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved, and the compound has good application effect and industrialization prospect.
Drawings
Fig. 1 is a schematic structural diagram of the application of the materials enumerated in the present invention to an OLED device, wherein the components represented by the respective reference numerals are as follows:
1. transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, hole transport layer, 5, electron blocking layer, 6, luminescent layer, 7, hole blocking/electron transport layer, 8, electron injection layer, 9, cathode reflection electrode layer.
FIG. 2 is a graph of current efficiency measured at different temperatures for OLED devices prepared with the compounds of the present invention.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
Preparation of intermediate I-1
Adding 0.01mol of raw material A-1, 0.012mol of raw material B-1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, then adding 0.03mol of sodium tert-butoxide, 5 × 10-5molPd2(dba)3，5×10-5Heating the mol tri-tert-butylphosphine to 105 ℃, carrying out reflux reaction for 24 hours, sampling a point plate, and indicating that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain a target product, wherein the HPLC purity is 98.4%, and the yield is 89.2%; elemental analysis Structure (molecular formula C)25H16BrN3): theoretical value C, 68.50; h, 3.68; br, 18.23; n,959; test values are: c, 68.51; h, 3.68; br, 18.23; and N, 9.58. ESI-MS (M/z) (M +): theoretical value is 437.05, found 437.11.
Other intermediates I were prepared in a similar manner to intermediate I-1, and the specific structure of intermediate I used in the present invention is shown in Table 1.
TABLE 1
EXAMPLE 1 preparation of Compound 2
Adding 0.01mol of intermediate I-1, 0.012mol of raw material II-1, 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, then adding 0.03mol of sodium tert-butoxide, 5 × 10 mol-5molPd2(dba)3，5×10-5Heating the mol tri-tert-butylphosphine to 105 ℃, carrying out reflux reaction for 24 hours, sampling a point plate, and indicating that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain a target product, wherein the HPLC purity is 95.7%, and the yield is 84.9%;
elemental analysis Structure (molecular formula C)52H38N4): theoretical value C, 86.88; h, 5.33; n, 7.79; test values are: c, 86.88; h, 5.34; n, 7.78. HPLC-MS: the molecular weight of the material is 718.31, and the measured molecular weight is 718.26.
EXAMPLE 2 preparation of Compound 14
Compound 14 was prepared as in example 1, except that starting material II-2 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)55H42N4): theoretical value C, 87.04; h, 5.58; n, 7.38; test values are: c, 87.05; h, 5.58; n, 7.37. HPLC-MS: the molecular weight of the material is 758.34, and the measured molecular weight is 758.42.
EXAMPLE 3 preparation of Compound 26
Compound 26 was prepared as in example 1, except that starting material II-3 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)62H42N4): theoretical value C, 88.33; h, 5.02; n, 6.65; test values are: c, 88.32; h, 5.02; and N, 6.66. HPLC-MS: the molecular weight of the material is 842.34, and the measured molecular weight is 843.39.
EXAMPLE 4 preparation of Compound 33
Compound 33 was prepared as in example 1, except that starting material II-4 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)54H37N5): theoretical value C, 85.80; h, 4.93; n, 9.26; test values are: c, 85.80; h, 4.94; and N, 9.25. HPLC-MS: the molecular weight of the material is 755.30, and the measured molecular weight is 755.27.
EXAMPLE 5 preparation of Compound 51
Compound 51 was prepared as in example 1, except that starting material II-5 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)55H36N4O): theoretical value C, 85.91; h, 4.72; n, 7.29; o, 2.08; test values are: c, 85.91; h, 4.72; n, 7.28; and O, 2.09. HPLC-MS: the molecular weight of the material is 768.29, and the measured molecular weight is 768.36.
EXAMPLE 6 preparation of Compound 61
Compound 61 was prepared as in example 1, except that starting material II-6 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)61H40N4O): theoretical value C, 86.70; h, 4.77; n, 6.63; o, 1.89; test values are: 86.70, respectively; h, 4.77; n, 6.64; o, 1.88. HPLC-MS: the molecular weight of the material is 844.32, and the measured molecular weight is 844.42.
EXAMPLE 7 preparation of Compound 77
Compound 77 was prepared as in example 1, except that starting material II-7 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)53H36N4): theoretical value C, 87.33; h, 4.98; n, 7.69; test values are: c, 87.34; h, 4.98; and N, 7.68. HPLC-MS: the molecular weight of the material is 728.29, and the measured molecular weight is 728.34.
EXAMPLE 8 preparation of Compound 84
Compound 84 was prepared as in example 1, except that starting material II-8 was used in place of starting material II-1. Elemental analysis Structure (molecular formula C)58H42N4): theoretical value C, 87.63; h, 5.33; n, 7.05; test values are: c, 87.63; h, 5.34; and N, 7.04. HPLC-MS: the molecular weight of the material is 794.34, and the measured molecular weight is 794.25.
EXAMPLE 9 preparation of Compound 91
Compound 91 was prepared as in example 1, except that intermediate I-2 was used in place of intermediate I-1. YuanElemental analysis Structure (molecular formula C)52H38N4): theoretical value: c, 86.88; h, 5.33; n, 7.79; test values are: c, 86.89; h, 5.33; n, 7.78. HPLC-MS: the molecular weight of the material is 718.31, and the measured molecular weight is 718.26.
EXAMPLE 10 preparation of Compound 100
Compound 100 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-2 and starting material II-1 is replaced with starting material II-2. Elemental analysis Structure (molecular formula C)55H42N4): theoretical value: c, 87.04; h, 5.58; n, 7.38; test values are: c, 87.05; h, 5.58; n, 7.37. HPLC-MS: the molecular weight of the material is 758.34, and the measured molecular weight is 758.26.
EXAMPLE 11 preparation of Compound 112
Compound 112 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-2 and starting material II-1 is replaced with starting material II-9. Elemental analysis Structure (molecular formula C)62H44N4): theoretical value: c, 88.12; h, 5.25; n, 6.63; test values are: c, 88.11; h, 5.26; and N, 6.63. HPLC-MS: the molecular weight of the material is 844.36, and the measured molecular weight is 844.28.
EXAMPLE 12 preparation of Compound 132
Compound 132 was prepared as in example 1, except that intermediate I-1 was replaced with intermediate I-2 and starting material II-1 was replaced with starting material II-10. Elemental analysis Structure (molecular formula C)59H40N4): theoretical value: c, 88.03; h, 5.01; n, 6.96; test values are: c, 88.03; h, 5.00; and N, 6.97. HPLC-MS: molecular weight of materialA molecular weight of 804.50 was found to be 804.33.
EXAMPLE 13 preparation of Compound 141
Compound 141 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-3 and starting material II-1 is replaced with starting material II-11. Elemental analysis Structure (molecular formula C)49H34N4): theoretical value: c, 86.70; h, 5.05; n, 8.25; test values are: c, 86.70; h, 5.04; and N, 8.26. HPLC-MS: the molecular weight of the material is 678.28, and the measured molecular weight is 678.35.
EXAMPLE 14 preparation of Compound 165
Compound 165 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-3 and starting material II-1 is replaced with starting material II-12. Elemental analysis Structure (molecular formula C)55H36N4O): theoretical value: c, 85.91; h, 4.72; n, 7.29; o, 2.08; test values are: c, 85.90; h, 4.73; n, 7.29; and O, 2.08. HPLC-MS: the molecular weight of the material is 768.29, and the measured molecular weight is 768.25.
EXAMPLE 15 preparation of Compound 195
Compound 195 is prepared as in example 1, except that intermediate I-4 is used instead of intermediate I-1 and starting material II-2 is used instead of starting material II-1. Elemental analysis Structure (molecular formula C)48H37N5): theoretical value: c, 84.31; h, 5.45; n, 10.24; test values are: c, 84.32; h, 5.45; n, 10.23. HPLC-MS: the molecular weight of the material is 683.30, and the measured molecular weight is 683.28.
EXAMPLE 16 preparation of Compound 205
Compound 205 was prepared as in example 1, except that intermediate I-1 was replaced with intermediate I-5 and starting material II-1 was replaced with starting material II-13. Elemental analysis Structure (molecular formula C)55H38N4): theoretical value: c, 87.50; h, 5.07; n, 7.42; test values are: c, 87.50; h, 5.06; and N, 7.43. HPLC-MS: the molecular weight of the material is 754.31, and the measured molecular weight is 754.42.
EXAMPLE 17 preparation of Compound 215
Compound 215 is prepared as in example 1, except that intermediate I-5 is used in place of intermediate I-1. Elemental analysis Structure (molecular formula C)58H42N4): theoretical value: c, 87.63; h, 5.33; n, 7.05; test values are: c, 87.63; h, 5.34; and N, 7.04. HPLC-MS: the molecular weight of the material is 794.34, and the measured molecular weight is 794.26.
EXAMPLE 18 preparation of Compound 234
Compound 234 was prepared as in example 1, except that intermediate I-1 was replaced with intermediate I-5 and starting material II-1 was replaced with starting material II-14. Elemental analysis Structure (molecular formula C)70H50N4): theoretical value: c, 88.76; h, 5.32; n, 5.92; test values are: c, 88.75; h, 5.32; and N, 5.93. HPLC-MS: the molecular weight of the material is 946.40, and the measured molecular weight is 946.52.
EXAMPLE 19 preparation of Compound 250
Compound 250 was prepared as in example 1, except thatThe intermediate I-6 is used for replacing the intermediate I-1, and the raw material II-15 is used for replacing the raw material II-1. Elemental analysis Structure (molecular formula C)53H36N4): theoretical value: c, 87.33; h, 4.98; n, 7.69; test values are: c, 87.34; h, 4.99; and N, 7.67. HPLC-MS: the molecular weight of the material is 728.29, and the measured molecular weight is 728.32.
EXAMPLE 20 preparation of Compound 262
Compound 262 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-6 and starting material II-1 is replaced with starting material II-2. Elemental analysis Structure (molecular formula C)53H40N4): theoretical value: c, 86.85; h, 5.50; n, 7.64; test values are: c, 86.85; h, 5.49; and N, 7.65. HPLC-MS: the molecular weight of the material is 732.33, and the measured molecular weight is 732.19.
EXAMPLE 21 preparation of Compound 271
Compound 271 was prepared as in example 1, except that intermediate I-7 was used in place of intermediate I-1. Elemental analysis Structure (molecular formula C)58H42N4): theoretical value: c, 87.63; h, 5.33; n, 7.05; test values are: c, 87.62; h, 5.33; and N, 7.06. HPLC-MS: the molecular weight of the material is 794.34, and the measured molecular weight is 794.41.
EXAMPLE 22 preparation of Compound 274
Compound 274 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-7 and starting material II-1 is replaced with starting material II-16. Elemental analysis Structure (molecular formula C)61H40N4O): theoretical value: c, 86.70; h, 4.77; n, 6.63; o, 1.89; measuringTest values are as follows: c, 86.70; h, 4.78; n, 6.63; o, 1.88. HPLC-MS: the molecular weight of the material is 844.32, and the measured molecular weight is 844.26.
EXAMPLE 23 preparation of Compound 285
Compound 285 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-8 and starting material II-1 is replaced with starting material II-17. Elemental analysis Structure (molecular formula C)55H36N4O): theoretical value: c, 85.91; h, 4.72; n, 7.29; o, 2.08; test values are: c, 85.91; h, 4.73; n, 7.29; and O, 2.07. HPLC-MS: the molecular weight of the material is 768.29, and the measured molecular weight is 768.18.
EXAMPLE 24 preparation of Compound 298
Compound 298 is prepared as in example 1, except that intermediate I-1 is replaced with intermediate I-9 and starting material II-1 is replaced with starting material II-18. Elemental analysis Structure (molecular formula C)41H28N4): theoretical value: c, 84.09; h, 4.70; n, 8.72; test values are: c, 84.09; h, 4.71; and N, 8.72. HPLC-MS: the molecular weight of the material is 576.23, and the measured molecular weight is 576.17.
The compound is used in a light-emitting device, has high glass transition temperature (Tg) and triplet state energy level (T1), and suitable HOMO and LUMO energy levels, and can be used as hole transport, electron blocking and light-emitting layer materials. The compounds prepared in the above examples of the present invention and the prior art materials HTR1, HTR2, HTR3 were tested for thermal properties, T1 energy level, and HOMO energy level, respectively, and the results are shown in table 2.
TABLE 2
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10- 5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy test system (IPS-3), which is an atmospheric environment.
The data in the table show that the compound has high glass transition temperature, can improve the phase stability of the material film, and further improves the service life of the device; the compound contains an electron donor and an electron acceptor, so that electrons and holes of an OLED device applying the compound reach a balanced state, the recombination rate of the electrons and the holes is ensured, the efficiency and the service life of the OLED device are improved, and the material has a high triplet state energy level, can block energy loss of a light-emitting layer, and improves the light-emitting efficiency of the device. Meanwhile, the material has a proper HOMO energy level, so that the problem of carrier injection can be solved, and the voltage of a device can be reduced; therefore, after the organic material is applied to different functional layers of an OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
The compounds HTR1, HTR2 and HTR3 are structures in patent CN106565720A, which is a comparative structure in this patent. The HOMO of the comparative compound is distributed on the benzimidazole segment, so that the HOMO energy level is deepened, when the compound is used as a hole transport material, a hole injection potential barrier is enlarged, excitons are easy to combine at the interface close to a light emitting layer, and the light emitting efficiency is reduced; the compound HOMO is distributed on the triarylamine fragment, the HOMO energy level is moderate, and the compound HOMO can be used as a hole transport material or an electron blocking material, is beneficial to injecting holes into a light-emitting layer and improves the light-emitting efficiency; the T1 energy level of the compound is larger than 2.60, and the higher T1 energy level is beneficial to blocking the energy loss of a light-emitting layer, so that the light-emitting efficiency of the device is improved, and therefore the device containing the compound has higher device efficiency. The calculated and measured physical properties of the comparative materials are shown in Table 3.
TABLE 3
Note: the simulation calculation uses Gaussian 16 software, and adopts B3LYP/6-31G (d) method and base group.
The compound of the present invention has high carrier mobility, both as a hole transport layer/electron blocking layer and as a host material for a light emitting layer, and has high carrier mobility as compared to a comparative compound. The high carrier mobility is beneficial to the transfer of holes or electrons in the device, and the transmission performance of the device is improved, so that the exciton utilization rate and the high-efficiency fluorescence radiation efficiency are improved, the efficiency roll-off under high current density is reduced, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged. Table 4 lists the results of mobility tests for the comparative structures and compounds of the invention:
TABLE 4
And (3) mobility determination: the material was fabricated into single charge devices and tested by the SCLC method.
The effect of the compounds of the present invention in the application of OLED devices will now be illustrated by the device examples. Device examples 2 to 27 and device comparative examples 1 to 4 were completely the same as device example 1 in terms of the manufacturing process, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept the same, except that the hole transport, electron blocking layer material or light emitting layer material in the devices were changed, the composition of each layer of each device is shown in table 5, and the performance test results of each device are shown in tables 6 and 7.
Device example 1
As shown in fig. 1, an electroluminescent device is prepared by the following steps:
a) cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes;
b) evaporating HAT-CN as a hole injection layer 3 on the ITO anode layer 2 in a vacuum evaporation mode, wherein the evaporation thickness is 10 nm;
c) evaporating a compound HT-1 on the hole injection layer 3 in a vacuum evaporation mode to form a hole transport layer 4, wherein the evaporation thickness is 60 nm; evaporating the compound 2 of the invention as an electron blocking layer 5 on the hole transport layer 4 in a vacuum evaporation mode, wherein the evaporation thickness is 20 nm;
d) a light-emitting layer 6 is vapor-plated on the electron blocking layer 5, the main material of the light-emitting layer 6 is GH-1 and GH-2, the doping material is GD-1, the mass ratio of GH-1, GH-2 and GD-1 is 45:45:10, and the thickness is 30 nm;
e) evaporating ET-1 and Liq on the light-emitting layer 6 in a vacuum evaporation mode according to the mass ratio of 1:1, wherein the thickness of the light-emitting layer is 35nm, the light-emitting layer is used as a hole blocking/electron transporting layer 7, and the evaporation thickness is 40 nm;
f) vacuum evaporation of an electron injection layer LiF serving as an electron injection layer 8 is carried out on the hole blocking/electron transport layer 7, and the evaporation thickness is 1 nm;
g) and vacuum evaporating cathode Al on the electron injection layer 8 to form a cathode reflection electrode layer 9, wherein the evaporation thickness is 100nm, and thus the electroluminescent device is obtained.
The composition of each layer of each device is shown in table 5, the performance test results of each device are shown in tables 6 and 7, and the structural formula of the material used by each device is as follows:
TABLE 5
TABLE 6
Note: LT97 refers to a current density of 10mA/cm2In the case, the time taken for the luminance of the device to decay to 97%;
the life test system is a Korean pulse science M600 type OLED device life tester.
From the results in table 6, it can be seen that the benzimidazole-containing organic compound prepared by the present invention can be applied to the fabrication of OLED light emitting devices, and compared with comparative device examples, the efficiency and lifetime of the compound are greatly improved compared with those of known OLED materials, and especially, the lifetime decay of the device is greatly improved.
In order to compare the efficiency attenuation conditions of different devices under high current density, the efficiency attenuation coefficient phi of each device is defined, wherein phi represents that the driving current is 100mA/cm2The larger the phi value is, the more serious the efficiency roll-off of the device is, and otherwise, the problem of rapid attenuation of the device under high current density is controlled. The efficiency attenuation coefficient phi of the devices obtained in device examples 1-27 and device comparative examples 1-4 was determined, and the results are shown in Table 7:
TABLE 7
| Device embodiments | Coefficient of attenuation of efficiency phi | Device embodiments | Coefficient of attenuation of efficiency phi |
| 1 | 0.26 | 17 | 0.23 |
| 2 | 0.28 | 18 | 0.25 |
| 3 | 0.25 | 19 | 0.24 |
| 4 | 0.22 | 20 | 0.26 |
| 5 | 0.23 | 21 | 0.27 |
| 6 | 0.25 | 22 | 0.22 |
| 7 | 0.25 | 23 | 0.23 |
| 8 | 0.24 | 24 | 0.25 |
| 9 | 0.25 | 25 | 0.19 |
| 10 | 0.23 | 26 | 0.24 |
| 11 | 0.28 | 27 | 0.21 |
| 12 | 0.25 | ||
| 13 | 0.26 | Comparative example 1 | 0.41 |
| 14 | 0.27 | Comparative example 2 | 0.43 |
| 15 | 0.22 | Comparative example 3 | 0.39 |
| 16 | 0.21 | Comparative example 4 | 0.46 |
As can be seen from the data in table 7, the organic light emitting device prepared by using the compound of the present invention has a smaller efficiency decay coefficient, which indicates that the organic light emitting device prepared by using the compound of the present invention can effectively reduce the efficiency roll-off.
The efficiency of the OLED device prepared by the compound is stable when the OLED device works at low temperature, the efficiency of the devices obtained in device examples 1, 5 and 9 and device comparative example 1 is tested at the temperature of-10-80 ℃, and the obtained results are shown in Table 8 and FIG. 2.
TABLE 8
As can be seen from the data in table 8 and fig. 2, device examples 1, 5, and 9 are device structures in which the compound of the present invention and known materials are combined, and compared to device comparative example 1, the efficiency is high at low temperature, and the efficiency is smoothly increased during the temperature increase.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. An organic compound containing benzimidazole, wherein the structure of the compound is shown as a general formula (1):
in the general formula (1), L represents one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl and substituted or unsubstituted naphthylene;
Ar1、Ar2each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted 5-30 membered heteroarylene containing one or more heteroatoms;
R1、R2each independently represents substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
the substituents which may be substituted are optionally selected from protium, deuterium, tritium, cyano, halogen, C1-20Alkyl radical, C6-30One or more of aryl and 5-30 membered heteroaryl;
the heteroatom is selected from oxygen atom, sulfur atom or nitrogen atom.
2. The benzimidazole-containing organic compound of claim 1, wherein R is1、R2Each independently represents a substituted or substituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted pyrenyl group, a structure represented by the general formula (2) or the general formula (3);
said X1、X2、X3Each independently represents an oxygen atom, a sulfur atom, -C (R)3)(R4) -or-N (R)5) -, and X1、X3May also represent a single bond;
said L1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranylene group;
z represents a nitrogen atom or C (R)6) (ii) a Z at the attachment site is represented as a carbon atom;
the R is3～R5Are each independently represented by C1-10Alkyl, substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; wherein R is1And R2Can also be connected with each other to form a ring;
the R is6Represented by hydrogen atom, protium, deuterium, tritium, cyano group, halogen atom, C1-10Alkyl radical, C2-10Alkylene, substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; two adjacent R6Can be connected with each other to form a ring;
the substituents which may be substituted are optionally selected from protium, deuterium, tritium, cyano, halogen, C1-20Alkyl radical, C2-20Alkenyl radical, C6-30One or more of aryl and 5-30 membered heteroaryl;
the heteroatom is selected from oxygen atom, sulfur atom or nitrogen atom.
3. The benzimidazole-containing organic compound of claim 1, wherein Ar is selected from the group consisting of1、Ar2Each independently representIs one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolyl and substituted or unsubstituted naphthyridinylene;
the R is3～R5Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyridinyl;
the R is6Represented by a hydrogen atom, protium, deuterium, tritium, cyano group, fluorine atom, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted terphenylyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group;
the substituent of the substitutable group is one or more selected from protium, deuterium, tritium, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuryl, carbazolyl or pyridyl.
4. The benzimidazole-containing organic compound according to claim 1, wherein the compound has a specific structure:
5. An organic electroluminescent element, characterized in that at least one functional layer in the organic electroluminescent element comprises the organic benzimidazole-containing compound according to any one of claims 1 to 4.
6. An organic electroluminescent device according to claim 5, comprising an electron-blocking or hole-transporting layer, wherein the hole-transporting or electron-blocking layer comprises the benzimidazole-containing organic compound according to any one of claims 1 to 4.
7. An organic electroluminescent device according to claim 5, comprising a light-emitting layer, wherein the light-emitting layer contains the benzimidazole-containing organic compound according to any one of claims 1 to 4.
8. A lighting or display element comprising an organic electroluminescent device as claimed in claims 5 to 7.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111801332A (en) * | 2018-03-09 | 2020-10-20 | 默克专利有限公司 | Compounds for electronic devices |
| CN113956260A (en) * | 2021-11-10 | 2022-01-21 | 上海和辉光电股份有限公司 | Novel arylamine compound and synthesis method and application thereof |
| CN114539260A (en) * | 2020-11-19 | 2022-05-27 | 上海和辉光电股份有限公司 | Compound and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106467549A (en) * | 2016-08-03 | 2017-03-01 | 江苏三月光电科技有限公司 | A kind of compound containing benzimidazole and its application on organic electroluminescence device |
| CN111801332A (en) * | 2018-03-09 | 2020-10-20 | 默克专利有限公司 | Compounds for electronic devices |
-
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106467549A (en) * | 2016-08-03 | 2017-03-01 | 江苏三月光电科技有限公司 | A kind of compound containing benzimidazole and its application on organic electroluminescence device |
| CN111801332A (en) * | 2018-03-09 | 2020-10-20 | 默克专利有限公司 | Compounds for electronic devices |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111801332A (en) * | 2018-03-09 | 2020-10-20 | 默克专利有限公司 | Compounds for electronic devices |
| CN114539260A (en) * | 2020-11-19 | 2022-05-27 | 上海和辉光电股份有限公司 | Compound and application thereof |
| CN114539260B (en) * | 2020-11-19 | 2023-09-29 | 上海和辉光电股份有限公司 | Compound and application thereof |
| CN113956260A (en) * | 2021-11-10 | 2022-01-21 | 上海和辉光电股份有限公司 | Novel arylamine compound and synthesis method and application thereof |
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