CN115141137A - Benzfluorene compound, organic electroluminescent device and display device - Google Patents
Benzfluorene compound, organic electroluminescent device and display device Download PDFInfo
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- CN115141137A CN115141137A CN202110348950.3A CN202110348950A CN115141137A CN 115141137 A CN115141137 A CN 115141137A CN 202110348950 A CN202110348950 A CN 202110348950A CN 115141137 A CN115141137 A CN 115141137A
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- compound
- organic electroluminescent
- electroluminescent device
- benzfluorene
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- -1 Benzfluorene compound Chemical class 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 24
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001514 detection method Methods 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [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
- 239000000243 solution Substances 0.000 description 7
- BXVWLQIKNMFQCS-UHFFFAOYSA-N 9-bromo-11,11-dimethylbenzo[a]fluorene Chemical compound C1=CC=CC2=C3C(C)(C)C4=CC(Br)=CC=C4C3=CC=C21 BXVWLQIKNMFQCS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229940126657 Compound 17 Drugs 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- MQAIWWRJGVSXKV-UHFFFAOYSA-N 2-bromo-11,11-dimethylbenzo[b]fluorene Chemical compound C1=CC=C2C=C3C(C)(C)C4=CC(Br)=CC=C4C3=CC2=C1 MQAIWWRJGVSXKV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-UHFFFAOYSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- PDOQLUHQQRDCES-UHFFFAOYSA-N 4-(9-phenylcarbazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 PDOQLUHQQRDCES-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PWRKEYBSOWAIMY-UHFFFAOYSA-N 3,5-diphenylaniline Chemical group C=1C(N)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 PWRKEYBSOWAIMY-UHFFFAOYSA-N 0.000 description 1
- AZGVZMFTHCOVID-UHFFFAOYSA-N 3-(4-bromophenyl)-9-(4-phenylphenyl)carbazole Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AZGVZMFTHCOVID-UHFFFAOYSA-N 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 239000011799 hole material Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application relates to the field of electroluminescence, and discloses a benzfluorene compound, an organic electroluminescent device and a display device. The structural formula of the benzfluorene compound is shown as a formula (I):
Description
Technical Field
The application relates to the field of electroluminescence, in particular to a benzfluorene compound, an organic electroluminescent device and a display device.
Background
Currently, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to large-size application fields such as televisions. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated by different designs of the device structure and optimization of the device life, efficiency and other properties, so that the OLED is widely applied in the fields of display and illumination.
In order to meet the higher requirements of people on OLED devices, the development of more various and higher-performance OLED materials is urgently needed in the field.
Disclosure of Invention
The application discloses a benzfluorene compound, an organic electroluminescent device and a display device.
In order to achieve the purpose, the application provides the following technical scheme:
a benzfluorene compound is shown as a formula (I),
wherein Ar1 and Ar4 are selected from hydrogen, benzene and biphenyl;
m and n are selected from 0,1,2,3,4,5; and m + n is greater than or equal to 1; and n is selected from 0: m is selected from 2,3,4,5, ar1 is selected from benzene, or m is selected from 1, ar1 is selected from biphenyl;
ar2, ar3 are independently selected from X, Y, Z, and at least one of Ar2, ar3 is selected from one of Y and Z;
r1 and R2 are selected from substituted or unsubstituted alkyl with 1 to 6 carbon atoms and substituted or unsubstituted aryl with 6 to 13 carbon atoms, and R1 and R2 can be connected into a ring through a single bond;
the compound shown in the formula (I) can be substituted by one or more R, wherein R is selected from deuterium, F, CN, substituted or unsubstituted alkyl with 1-6 carbon atoms and substituted or unsubstituted aryl with 6-13 carbon atoms;
the following compounds are excluded:
further, at least one of Ar2 and Ar3 is selected from Y-1, Y-2, Z-1, Z-2:
further, ar2 is selected from Y-1, Y-2, Z-1, Z-2, and Ar3 is selected from X.
Further, ar2 and Ar3 are selected from Y-1, Y-2, Z-1 and Z-2.
Further, ar2 and Ar3 are selected from Y-1, Y-2, Z-1 and Z-2, and Ar2 and Ar3 are different.
Further, m is selected from 0, n is selected from 1.
Further, m is selected from 1, n is selected from 1.
Further, one of m and n is selected from 2, and the other is selected from 0.
Further, R1 and R2 are selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl and biphenyl.
Further, the benzfluorene compound is selected from one of the following structures and isomers thereof:
the isomers refer to:
in the specific structures listed above, the substituent Ar1 of the benzene ring on the N atom of the carbazole ring is bonded at a specific position, ar4 is also bonded at a specific position corresponding to the benzene ring in formula X, and when Ar1, ar4 are selected from biphenyl groups, the two benzene rings of the biphenyl are also bonded at specific positions.
With respect to the above specific structures, any possible connection of Ar1 on the benzene ring and/or any possible connection of Ar4 on the benzene ring and/or any possible connection of the two benzene rings of the biphenyl when Ar1, ar4 are selected from biphenyl groups, defined as isomers of the above compounds 1-60, is also within the scope of the present invention.
Examples are as follows:
compound 3 has the structure:
its isomers include the following two structures:
compound 13 has the structure:
isomers thereof include, but are not limited to, the following structures:
isomers of other compounds can be understood with reference to the above written explanations and specific examples.
An organic electroluminescent device comprising a benzfluorene-based compound as described herein.
Further, the host material of the hole transport layer or the light emitting layer of the organic electroluminescent device is the compound disclosed by the application.
A display device includes the organic electroluminescent device provided by the application.
By adopting the technical scheme of the application, the beneficial effects are as follows:
the compound shown in the formula (I) is a novel compound, can be used for organic electroluminescent devices, and can be used as HTL and Host materials.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
It should be noted that: in the present application, all embodiments and preferred methods mentioned herein can be combined with each other to form new solutions, if not specifically stated. In the present application, all the technical features mentioned herein and preferred features may be combined with each other to form new solutions, if not specifically stated. In the present application, percentages (%) or parts refer to percent by weight or parts by weight relative to the composition, unless otherwise specified. In the present application, the components referred to or the preferred components thereof may be combined with each other to form a new embodiment, if not specifically stated. In this application, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers. For example, a numerical range of "6 to 22" indicates that all real numbers between "6 to 22" have been listed herein, and "6 to 22" is only an abbreviated representation of the combination of these numbers. The "ranges" disclosed herein may be in the form of lower limits and upper limits, and may be one or more lower limits and one or more upper limits, respectively. In the present application, unless otherwise indicated, the individual reactions or process steps may or may not be performed in sequence. Preferably, the reaction processes herein are carried out sequentially.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present application.
Synthesis example 1 Synthesis of Compound 3
The synthetic route for compound 3 is as follows:
a 500 ml three-necked flask was charged with nitrogen, and charged with 350 ml of dried toluene, 4.87 g (0.01 mol) of a compound represented by M-1, 3.55 g (0.011 mol) of 9-bromo-11, 11-dimethyl-11H-benzo [ a ] fluorene, 0.0575 g (0.0001 mol) of Pd (dba) 2 (bis (dibenzylideneacetone palladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% of tri-tert-butylphosphine, 1.44 g (0.015 mol) of sodium tert-butoxide, heated to reflux reaction for 12 hours, cooled, added with water for liquid separation, washed with water to neutrality of the organic layer, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, petroleum ether: ethyl acetate =9:1 (volume ratio) to obtain 4.19 g of the compound represented by the formula 3.
Performing mass spectrum detection on the compound shown in the formula 3, and determining that the molecular m/z is as follows: 728.
the compound shown in 3 was subjected to nuclear magnetic detection, and the data were analyzed as follows:
1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3) < delta > 8.57 (m, 1H), < delta > 8.22 to 8.18 (m, 2H), < delta > 8.13 to 8.04 (m, 2H), < delta > 7.96 (m, 1H), < delta > 7.77 (m, 2H), < delta > 7.72 (d, 1H), < delta > 7.66 to 7.34 (m, 23H), < delta > 7.20 to 7.08 (m, 2H), < delta > 1.83 (s, 6H).
Synthesis example 2 Synthesis of Compound 5
(1) Synthesis of intermediate M-2
A 250 ml three-neck flask, under the protection of nitrogen, 100 ml of dry toluene, 4.74 g of 9- ([ 1,1' -biphenyl ] -4-yl) -3- (4-bromophenyl) -9H-carbazole, 1.69 g of 4-aminobiphenyl, 0.0575 g of Pd (dba) 2 (bis (dibenzylideneacetone palladium), 0.4 g of toluene solution containing 10% tri-tert-butylphosphine and 1.44 g of sodium tert-butoxide, the mixture is heated to 60 ℃ for reaction for 12 hours, cooled, added with water for liquid separation, washed with water to be neutral in an organic layer, dried by magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to be dry, and crystallized by a mixed solvent of toluene and ethanol to obtain 3.8 g of the compound represented by M-2.
Performing mass spectrum detection on the compound shown as M-2, and determining that the molecular M/z is as follows: 562.
(2) Synthesis of Compound 5
Referring to the synthesis of compound 3 in example 1, except for changing the compound represented by M-1 to the compound represented by M-2 and the 9-bromo-11, 11-dimethyl-11H-benzo [ a ] fluorene to 2-bromo-11, 11-dimethyl-11H-benzo [ b ] fluorene, compound 5 was obtained.
Mass spectrum detection is carried out on the compound 5, and the molecule m/z is determined to be: 804.
synthesis example 3 Synthesis of Compound 17
(1) Synthesis of intermediate M-3
Reference example 2 was made to the synthesis of intermediate M-2 except that 4-aminobiphenyl was replaced with 3, 5-diphenylaniline to give M-3.
Performing mass spectrum detection on the compound shown in M-3, and determining that the molecular M/z is as follows: 638.
(2) Synthesis of Compound 17
Referring to the synthesis of compound 3 in example 1, except for changing the compound represented by M-1 to the compound represented by M-3 and changing the 9-bromo-11, 11-dimethyl-11H-benzo [ a ] fluorene to 2-bromo-11, 11-dimethyl-11H-benzo [ b ] fluorene, compound 17 was obtained.
Mass spectrometric detection of compound 17 determined the molecule m/z to be: 880.
synthesis example 4 Synthesis of Compound 41
A 250 ml three-neck flask, protected by nitrogen, added with 50 ml of dried toluene, 3.34 g (0.01 mol) of 4- (9-phenyl-9H-carbazol-3-yl) aniline, 7.1 g (0.022 mol) of 9-bromo-11, 11-dimethyl-11H-benzo [ a ] fluorene, 0.0575 g (0.0001 mol) of Pd (dba) 2 (bis-dibenzylideneacetone palladium), 0.4 g (0.0002 mol) of toluene solution containing 10% of tri-tert-butylphosphine, 1.44 g (0.015 mol) of sodium tert-butoxide, heated to reflux for 18 hours, cooled, filtered after adding water, the obtained solid is washed to neutrality, separated by silica gel column chromatography after drying, petroleum ether: ethyl acetate =9:1 (volume ratio) to obtain 6.5 g of the compound represented by 41.
Performing mass spectrum detection on the compound shown in the formula 41, and determining that the molecular m/z is as follows: 818.
synthesis example 5 Synthesis of Compound 43
(1) Synthesis of intermediate M-4
In a 250 ml three-necked flask, under nitrogen protection, 120 ml of dried toluene, 3.34 g (0.01 mol) of 4- (9-phenyl-9H-carbazol-3-yl) aniline, 3.22 (0.01 mol) of 9-bromo-11, 11-dimethyl-11H-benzo [ a ] fluorene, 0.0575 g (0.0001 mol) of Pd (dba) 2 (palladium bis (dibenzylideneacetone)), 0.4 g (0.0002 mol) of a toluene solution containing 10% of tri-tert-butylphosphine, 1.44 g (0.015 mol) of sodium tert-butoxide, heated to 60 ℃ for reaction for 12 hours, cooled, added with water for liquid separation, washed with an organic layer to neutrality, dried over magnesium sulfate, filtered to remove, concentrated to dryness, and crystallized from a mixed solvent of toluene and ethanol to obtain 3.11 g of a compound represented by M-4.
Performing mass spectrum detection on the compound shown in M-4, and determining that the molecular M/z is as follows: 576.
(2) Synthesis of Compound 43
Referring to the synthesis of compound 3 in example 1, except for changing the compound represented by M-1 to the compound represented by M-4 and the 9-bromo-11, 11-dimethyl-11H-benzo [ a ] fluorene to 2-bromo-11, 11-dimethyl-11H-benzo [ b ] fluorene, compound 43 was obtained.
Mass spectrometric detection of compound 43 determined the molecule m/z to be: 818.
the synthesis of products not shown in the above synthesis examples can be achieved by conventional methods according to methods known in the art.
Device embodiments
Several materials used in this application have the following specific structures:
device example 1
In the examples, the compound of the present application was used as a hole transport material in an organic electroluminescent device, and in the comparative examples, HT-1, HT-2, and HT-3 were used as hole transport materials in an organic electroluminescent device, respectively.
The structure of the organic electroluminescent device is as follows: ITO/hole transport material (20 nm)/GH 1 (30 nm): ir (piq) 3[ 2 ], [5% ]/TPBI (10 nm)/Alq 3 (15 nm)/LiF (0.5 nm)/Al (150 nm). Wherein "Ir (piq) 3 2 ], [5% ]" means the doping proportion of the green red dye, i.e. the weight part ratio of red host materials GH1 to Ir (piq) 3 is 100.
The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, respectively carrying out vacuum evaporation on the anode layer film to obtain a contrast material and the material of the invention as hole transport layers, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20nm;
vacuum evaporation is carried out on the hole transport layer to obtain a red light host material GH1 and a dye Ir (piq) 3 which are used as a light emitting layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, the total evaporation film thickness is 30nm, and the weight part ratio of the red light host material GH1 to the Ir (piq) 3 is 100;
sequentially vacuum evaporating an electron transport layer TPBI and an electron transport layer Alq3 on the light-emitting layer, wherein the evaporation rates are both 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15nm;
and (3) evaporating 0.5nm LiF and 150nm Al on the electron transport layer in vacuum to form an electron injection layer and a cathode.
All the organic electroluminescent devices are prepared by the method, and the difference is only in the selection of the hole transport material, and the details are shown in the following table 1.
And (3) performance testing:
the brightness, driving voltage, current efficiency, and LT95 of the prepared organic electroluminescent device were measured using the hangzhou remote production OLED-1000 multichannel accelerated aging lifetime and photochromic performance analysis system test, and the test results are shown in the following table. The lifetime data LT95 means that the current density at the initial luminance was kept constant at room temperature (25 to 27 ℃ C.) (here, 1000cd/m 2 ) The time (hour) required for the luminance to decrease to 95% of the initial luminance.
TABLE 1
As can be seen from the above table, compared with the comparative compound, the compound provided by the present application, when being used as a hole material for transporting an organic electroluminescent device, can improve the light emitting efficiency, reduce the driving voltage, and improve the lifetime.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.
Device example 2
The compound of the application is selected as a green light host material in an organic electroluminescent device in the embodiment, and GH1 and HT-3 are selected as green light host materials in the comparative example.
The structure of the organic electroluminescent device is as follows: ITO/compound 5 (30 nm)/green host material (30 nm): ir (ppy) 3[ 2 ], [7% ]/TPBI (10 nm)/Alq 3 (15 nm)/LiF (0.5 nm)/Al (150 nm). Wherein 7% in "Ir (ppy) 3 2 ], [7% ]" means the doping proportion of the green dye, i.e. the weight part ratio of green host material to Ir (ppy) 3 is 100.
The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, vacuum evaporating the hole transport layer of the compound 5 of the invention on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30nm;
vacuum evaporation of a green light main material and a dye Ir (ppy) 3 are carried out on the hole transport layer to be used as a light emitting layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, the total film thickness of the evaporation is 30nm, wherein the green light main material is selected from the compound and the comparison materials GH1 and HT-3 respectively;
sequentially vacuum evaporating an electron transport layer TPBI and an electron transport layer Alq3 on the light-emitting layer, wherein the evaporation rates are both 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15nm;
and (3) evaporating LiF with the thickness of 0.5nm and Al with the thickness of 150nm on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
All the organic electroluminescent devices are prepared by the method, and the differences only lie in the selection of green light main body materials, and the details are shown in the following table 2.
And (3) performance testing:
the test of the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced in the hangzhou distance measured the brightness, driving voltage, current efficiency of the prepared organic electroluminescent device, and the test results are shown in table 2 below.
TABLE 2
As can be seen from the data in table 2, compared with the compound of the comparative example, the compound provided by the present application as the green host material of the organic electroluminescent device can significantly improve the current efficiency of the organic electroluminescent device and effectively reduce the driving voltage.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.
Claims (10)
1. A benzfluorene compound is characterized in that the structural formula of the compound is shown as a formula (I),
wherein Ar1 and Ar4 are selected from hydrogen, benzene and biphenyl;
m, n are selected from 0,1,2,3,4,5; and m + n is greater than or equal to 1, and n is selected from 0: m is selected from 2,3,4,5, ar1 is selected from benzene, or m is selected from 1, ar1 is selected from biphenyl;
ar2, ar3 are independently selected from X, Y, Z, and at least one of Ar2, ar3 is selected from one of Y and Z;
r1 and R2 are selected from substituted or unsubstituted alkyl with 1 to 6 carbon atoms and substituted or unsubstituted aryl with 6 to 13 carbon atoms, and R1 and R2 can be connected into a ring through a single bond;
the compound shown in the formula (I) can be substituted by one or more R, wherein R is selected from deuterium, F, CN, substituted or unsubstituted alkyl with 1-6 carbon atoms and substituted or unsubstituted aryl with 6-13 carbon atoms;
the following compounds are excluded:
2. the compound of claim 1, wherein at least one of Ar2 and Ar3 is selected from the group consisting of Y-1, Y-2, Z-1, Z-2:
3. the compound of claim 1, wherein Ar2 is selected from the group consisting of Y-1, Y-2, Z-1, Z-2, and Ar3 is selected from the group consisting of X.
4. The compound of claim 1, wherein Ar2 and Ar3 are selected from the group consisting of Y-1, Y-2, Z-1 and Z-2, and Ar2 and Ar3 are not the same.
5. The compound of claim 1, m is selected from 0, n is selected from 1.
6. The compound of claim 1, wherein m is 1, and n is 1.
7. The compound of claim 1, wherein one of m and n is selected from 2 and the other is selected from 0.
8. The compound of claim 1, wherein R1 and R2 are selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl and biphenyl.
9. The compound of claim 1, selected from the group consisting of compounds 1-62 and isomers of compounds 1-62:
10. an organic electroluminescent device comprising a compound according to any one of claims 1 to 9.
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