CN117143140A - Triarylamine compound and organic electroluminescent device thereof - Google Patents
Triarylamine compound and organic electroluminescent device thereof Download PDFInfo
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- CN117143140A CN117143140A CN202311146290.6A CN202311146290A CN117143140A CN 117143140 A CN117143140 A CN 117143140A CN 202311146290 A CN202311146290 A CN 202311146290A CN 117143140 A CN117143140 A CN 117143140A
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- -1 Triarylamine compound Chemical class 0.000 title claims abstract description 158
- 238000000034 method Methods 0.000 claims abstract description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 75
- 125000002723 alicyclic group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000001624 naphthyl group Chemical group 0.000 claims description 39
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 39
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 38
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 38
- 235000010290 biphenyl Nutrition 0.000 claims description 38
- 239000004305 biphenyl Substances 0.000 claims description 38
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 37
- 229910052722 tritium Inorganic materials 0.000 claims description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 36
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 36
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 35
- 230000005525 hole transport Effects 0.000 claims description 35
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 35
- 125000005561 phenanthryl group Chemical group 0.000 claims description 33
- 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 32
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 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 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 29
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 27
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 26
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 21
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- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 20
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 18
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- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 18
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 17
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 4
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- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 5
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- DBNYWRKRZTXMCU-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 DBNYWRKRZTXMCU-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 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 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QHOMPCGOCNNMFK-UHFFFAOYSA-N tridec-6-ene Chemical compound CCCCCCC=CCCCCC QHOMPCGOCNNMFK-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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Abstract
The invention provides a triarylamine compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. The triarylamine compound has high hole mobility, and when the triarylamine compound is applied to a hole transmission region in an organic electroluminescent device, the energy barrier in the hole injection process can be reduced, the hole transmission rate is improved, the hole transmission rate and the electron transmission rate are balanced, and the maximum recombination of carriers is realized, so that the luminous efficiency and the service life of the device are improved. In addition, the triarylamine compound has higher refractive index, and can effectively reduce total reflection loss and waveguide loss in the device when being applied to a covering layer in the device, so that light trapped in the device is coupled out, and the light-emitting efficiency of the device is improved. The triarylamine compound provided by the invention can be applied to various fields such as display, illumination, commerce, medicine, traffic and the like.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a triarylamine compound and an organic electroluminescent device thereof.
Background
An Organic Light-Emitting Diode (OLED) has the advantages of high efficiency, high brightness, low driving voltage, good flexibility, wide viewing angle, high resolution, fast response speed, wide material selection range and the like, gradually becomes a research focus of related industries at home and abroad, is widely applied in various fields such as display, illumination and the like, and is a novel display technology which is most developed at present.
The organic electroluminescent device refers to a phenomenon in which light is emitted under excitation of a current or an electric field. The organic electroluminescent device comprises an anode, a cathode and an organic layer, along with the optimization of the structure of the device, the variety of materials is continuously increased, and the organic layer can comprise a hole injection layer, a hole transmission layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transmission layer, an electron injection layer, a covering layer and other functional layers, so that the organic functional layers play an important role in improving the photoelectric performance of the device, and can enable the device to emit light efficiently and stably.
The hole transport material is a key material of the organic electroluminescent device, and has the effects of improving the transport rate of holes in the device, balancing the hole transport rate and the electron transport rate, improving the recombination probability of excitons in the luminescent layer and realizing the maximum recombination of carriers. However, most of the existing hole transport materials have the problems of low hole mobility, poor film forming property, poor thermal stability and the like. The hole transport material with excellent performance has high hole mobility, good thermal stability and good film forming property, can reduce energy barrier in the hole injection process, and improves hole injection efficiency, thereby improving the performance of devices such as efficiency, service life and brightness.
In order to further improve the luminous efficiency of the OLED, it is proposed to provide a coating layer with a higher refractive index on the outer side of the semitransparent electrode with a lower refractive index. The application of the coating layer can reduce total reflection loss and waveguide loss in the device, couple out light trapped in the device, enhance the light extraction efficiency, and further improve the luminous efficiency of the device, but the research on the coating layer material at home and abroad is less at present.
Therefore, there is a need to design materials with excellent performance to improve the luminous efficiency of the device, prolong the service life of the device, and further comprehensively improve the performance of the organic electroluminescent device.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a triarylamine compound and an organic electroluminescent device thereof. When the light-emitting diode is applied to a hole transmission area or a cover layer of an organic electroluminescent device, the light-emitting efficiency of the device can be effectively improved, and the service life of the device can be prolonged. Specifically, the technical scheme of the invention is as follows:
the invention provides a triarylamine compound, which is represented by a structure shown in a formula I:
the Ar is as follows 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group;
The L is selected from any one of the following groups:
the x is selected from CH or N identically or differently;
the Y is 1 Selected from O, S, C (R) 2 R 3 )、N(R 4 ) One of the following;
the Y is 2 Selected from single bonds, O, S, C (R) 7 R 8 )、N(R 9 ) One of the following;
the R is 1 The halogen is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C2-C30 fused ring group of heteroaromatic ring; or two adjacent R 1 May be linked to each other to form a substituted or unsubstituted ring;
the R is 2 、R 3 、R 7 、R 8 Independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring; or said R 2 、R 3 May be linked to each other to form a substituted or unsubstituted ring;
the R is 4 、R 9 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group;
the a 1 Selected from 0, 1, 2 or 3; the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other;
the L is 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C15 alicyclic ring, and a C6-C30 arylene ring;
provided that the Ar is 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Containing one or more groups of formula II:
the R is a 、R b 、R c Independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, and fused ring group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or outside one or more than one of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds.
Advantageous effects
The triarylamine compound has high hole mobility, good thermal stability and good film forming property, and when the triarylamine compound is applied to a hole transmission area in an organic electroluminescent device, the energy barrier in the hole injection process can be reduced, the transmission rate of holes in the device is improved, the balance between the hole transmission rate and the electron transmission rate is realized, the recombination probability of excitons in a luminescent layer is improved, the maximum recombination of carriers is realized, and therefore, the luminous efficiency of the device is improved, and the service life of the device is prolonged. In addition, the triarylamine compound has higher refractive index, and can effectively reduce total reflection loss and waveguide loss in the device when being applied to a cover layer in an organic electroluminescent device, couple light trapped in the device out, enhance light extraction efficiency, and further improve luminous efficiency of the device.
Detailed Description
The following description of the embodiments of the present invention will be made more complete and obvious by the following description of the embodiments of the present invention, wherein the embodiments are described in some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance.
Examples of halogens described herein may include fluorine, chlorine, bromine and iodine.
In the present specification, "-" means a moiety attached to another substituent. "-" may be attached at any optional position of the attached group/fragment.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to any of the two or more rings, in particular to any of the corresponding selectable sites of the rings. For example, the number of the cells to be processed,can indicate-> Can indicate- >And so on.
In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring. For example, the number of the cells to be processed,can indicate-> Can representCan representAnd so on.
In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more, where allowed;
in this specification, "one or more" includes one, two, three, four, five, six or more where allowed.
In the present invention, "connection between two adjacent groups to form a ring" means that the adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring or aliphatic heterocyclic ring. The aliphatic ring and the aliphatic heterocyclic ring can be saturated rings or unsaturated rings, and the ring formed by connection can be a ternary ring, a quaternary ring, a five-membered ring, a six-membered ring, a seven-membered ring, a spiro ring or a condensed ring. Specific examples may include: benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.
"substituted" in "substituted or unsubstituted" as used herein means that at least one hydrogen atom on the group is replaced with a substituent. When a plurality of hydrogens are replaced with a plurality of substituents, the plurality of substituents may be the same or different. The position of the hydrogen substituted with the substituent may be any position. The substituents represented by "substitution" in the above "substituted or unsubstituted" include, but are not limited to, deuterium, tritium, cyano, nitro, halogen, substituted or unsubstituted C1 to C15 alkyl, substituted or unsubstituted C2 to C15 alkenyl, substituted or unsubstituted C3 to C15 alicyclic, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted C3 to C15 condensed ring group of alicyclic and C6 to C30 aromatic ring, substituted or unsubstituted C3 to C15 condensed ring group of alicyclic and C2 to C30 heteroaromatic ring, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C1 to C12 alkylthio, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C6 to C30 arylamino group, and the like. Preferably, it is: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, trifluoromethyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, anthryl, pyrenyl, benzocyclopropenyl, benzocyclobutanyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phenanthroline, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, indolyl, and the like, but not limited thereto. The above substituent may be further substituted with a substituent such as deuterium, alkyl, alicyclic group, alicyclic ring, aryl group, alicyclic ring and condensed ring group of aromatic ring, and condensed ring group of alicyclic ring and aromatic ring, and in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.
The alkyl group according to the present invention is a generic term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group may be substituted or unsubstituted. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like.
The alicyclic group according to the present invention means a generic term for monovalent groups obtained by removing at least one hydrogen atom from an alicyclic hydrocarbon molecule, and may be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, most preferably 3 to 7 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.
Aryl as used herein refers to the generic term for monovalent radicals obtained by removing one hydrogen atom from the aromatic nucleus of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, and most preferably from 6 to 12 carbon atoms. Aryl groups may be substituted or unsubstituted. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, such as phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, for example, but not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylene, triphenylene, fluoranthryl, fluorenyl, and the like.
Heteroaryl according to the present invention refers to the generic term for monovalent radicals obtained by substituting one or more aromatic nucleus carbon atoms in an aryl group with heteroatoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and most preferably 3 to 15 carbon atoms. The heteroaryl group may be substituted or unsubstituted. The attachment site of the heteroaryl group may be located on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, a fused ring heteroaryl group, or the like. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathianyl, spirofluorene oxaanthracyl, spirofluorene thianthrenyl, and the like.
The fused ring group of the alicyclic ring and the aromatic ring refers to the generic name of monovalent groups obtained by removing one hydrogen atom after the aromatic ring and the alicyclic ring are fused together. The aromatic ring is preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, most preferably 6 to 12 carbon atoms, the aliphatic ring is preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, most preferably 3 to 6 carbon atoms, and examples include benzocyclopropane group, benzocyclobutane group, benzocyclopentane group, benzocyclohexen group, benzocycloheptane group, benzocyclobutenyl group, benzocyclopentene group, benzocyclohexen group, benzocycloheptene group, naphthocyclopropane group, naphthocyclobutane group, naphthocyclopentane group, naphthocyclohexen group, naphthocyclopentene group, naphthocyclohexen group, and the like, but are not limited thereto.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the generic name of monovalent groups obtained by fusing the alicyclic ring and the heteroaromatic ring together and removing one hydrogen atom. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 3 to 6 carbon atoms. The heteroaromatic ring preferably has from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 3 to 15 carbon atoms. Examples may include, but are not limited to, pyrido-cyclobutyl, pyrido-cyclopentyl, pyrido-cyclohexyl, pyrido-cycloheptyl, pyrido-cyclopentenyl, pyrido-cyclohexenyl, and the like.
The arylene group refers to a generic term for divalent groups obtained by removing two hydrogen atoms from an aromatic nucleus. These are not only divalent groups but also aryl groups as described above.
The term "heteroarylene" as used herein means a generic term for a divalent group obtained by removing two hydrogen atoms from the nuclear carbon of an aromatic heterocycle composed of carbon and a heteroatom. They may be applied to the above description of heteroaryl groups, in addition to the divalent groups, respectively.
The term "fused ring-sub group" of an alicyclic ring and an aromatic ring as used herein refers to a generic term for divalent groups obtained by fusing an alicyclic ring and an aromatic ring together and then removing two hydrogen atoms. In addition to the divalent groups, the above description of the condensed ring groups of the alicyclic and aromatic rings may be applied.
The invention provides a triarylamine compound, which is represented by a structure shown in a formula I:
the Ar is as follows 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group;
The L is selected from any one of the following groups:
the x is selected from CH or N identically or differently;
the Y is 1 Selected from O, S, C (R) 2 R 3 )、N(R 4 ) One of the following;
the Y is 2 Selected from single bonds, O, S, C (R) 7 R 8 )、N(R 9 ) One of the following;
the R is 1 The halogen is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C2-C30 fused ring group of heteroaromatic ring; or two adjacent R 1 Can be connected with each other to form a substituted or unsubstitutedA ring;
the R is 2 、R 3 、R 7 、R 8 Independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring; or said R 2 、R 3 May be linked to each other to form a substituted or unsubstituted ring;
the R is 4 、R 9 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group;
the a 1 Selected from 0, 1, 2 or 3; the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other;
the L is 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C15 alicyclic ring, and a C6-C30 arylene ring;
provided that the Ar is 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Containing one or more groups of formula II:
the R is a 、R b 、R c Independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, and fused ring group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring.
Preferably, L is selected from any one of the following groups:
the R is 1 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, benzocyclobutenyl, benzocyclopentenyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzamidylOxazolyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, acridinyl, phenanthroline, a group of formula II; or two adjacent R 1 Can be connected with each other to form a substituted or unsubstituted benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring or C3-C8 aliphatic ring;
The R is 2 、R 3 、R 7 、R 8 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or R is 2 、R 3 Any one of them can be directly connected with L a 、L b 、L c Any one of which is bonded;
the R is 4 、R 9 Independently selected from one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, of formula II A group is shown; or R is 4 Can be directly connected with L a 、L b 、L c Any one of which is bonded;
the a 1 Selected from 0, 1, 2 or 3; the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; the a 4 Selected from 0 or 1; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other.
The R is 1 、R 2 、R 3 、R 4 、R 7 、R 8 、R 9 The substituent "substituted or unsubstituted" in (a) is selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, and when two or more substituents are present, the two or more substituents may be the same or different from each other.
Further preferably, the L is selected from any one of the following groups:
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the R is 1 Identically or differently selected from one of the following groups hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, a group of formula II; or two adjacent R 1 Can be connected with each other to form a substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring or C3-C8 aliphatic ring;
the R is 2 、R 3 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, a group of formula II;
the R is 4 Selected from one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene; or R is 4 Can be directly combined with La, L b 、L c Any one of which is bonded.
Preferably, said R a 、R b 、R c Independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, ethylene, propylene, butene, pentene, hexylheptene, cyclopropane, cyclobutane, cyclopentane, cyclohexenyl, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexenyl, cycloheptene, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;
The R is a 、R b 、R c The substituent of the "substituted or unsubstituted" in (a) is selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl and naphthylMore than one, when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, the formula II is selected from any one of the following groups:
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preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Independently selected from one of the following groups:
said y is identically or differently selected from N or CH;
the ring A is selected from a substituted or unsubstituted C3-C10 aliphatic ring;
the Y is 3 、Y 4 Independently selected from single bond, O, S, N (R) d )、C(R e R f ) One of the following;
the Y is 5 Selected from O, S, N (R) g )、C(R h R i ) One of the following; the Y is 6 Selected from N or CH;
the R is 5 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzofuranyl Benzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or two adjacent R 5 May be linked to each other to form a substituted or unsubstituted ring;
the R is d 、R g And is selected from the group consisting of substituted or unsubstituted one of the following groups, identically or differently: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or said R d 、R g Can be directly connected with L 1 、L 2 、L 3 、L 4 、L 5 、L 6 Any one of which is bonded;
the R is e 、R f 、R h 、R i Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or R is e 、R f May be linked to each other to form a substituted or unsubstituted ring; or R is e 、R f Any one of them can be directly connected with L 1 、L 2 、L 3 、L 4 、L 5 、L 6 Any one of which is bonded;
said b 1 Selected from 0, 1, 2, 3, 4 or 5; said b 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 4 Selected from 0, 1, 2, 3 or 4; said b 5 Selected from 0, 1, 2 or 3; when two or more R's are present 5 When two or more R' s 5 Are the same as or different from each other.
Further preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Independently selected from one of the following groups:
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the R is 5 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, a group of formula II; or two adjacent R 5 Can be connected with each other to form a substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring or C3-C8 an aliphatic ring;
the R is d 、R g And is selected from the group consisting of substituted or unsubstituted one of the following groups, identically or differently: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, a group of formula II;
the R is e 、R f 、R h 、R i Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutyl, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, a group of formula II;
The R is m Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl;
said b 1 Selected from 0, 1, 2, 3, 4 or 5; said b 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; by a means ofThe b 4 Selected from 0, 1, 2, 3 or 4; said b 5 Selected from 0, 1, 2 or 3; said b 6 Selected from 0, 1 or 2; said b 7 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said b 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 5 When two or more R' s 5 Are the same as or different from each other;
the R is 5 、R d 、R e 、R f 、R g 、R h 、R i 、R m The substituent "substituted or unsubstituted" in (a) is selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, and when two or more substituents are present, the two or more substituents may be the same or different from each other.
Still more preferably, ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 One, two, three, four, five or six of the following groups independently selected from:
more preferably, ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 One, two, three, four, five or six of the following groups independently selected from:
the remainder are independently selected from one of the following groups:
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preferably, L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Independently selected from a single bond or one of the following groups:
the z is identically or differently selected from N or CH;
the ring B is selected from a substituted or unsubstituted C3-C10 aliphatic ring;
said E is selected from O, S, N (R j )、C(R k R l ) One of the following;
the R is 6 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or two adjacent R 6 May be linked to each other to form a substituted or unsubstituted ring;
the R is j Selected from one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutylA group, a tert-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, an adamantane group, a norbornane group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a benzocyclobutane group, a benzocyclopentane group, a benzocyclohexane group, a fluorenyl group, a benzofuranyl group, a dibenzofuranyl group, a benzothienyl group, a dibenzothiophenyl group, an indolyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, and a quinoxalinyl group; or R is j Can be directly connected with Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Any one of which is bonded;
the R is k 、R l Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, a group of formula II; or R is k 、R l May be linked to each other to form a substituted or unsubstituted ring; or R is k 、R l Any one of them may be directly bonded to Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Any one of which is bonded;
the c 1 Selected from 0, 1, 2, 3 or 4; the c 2 Selected from 0, 1, 2 or 3; the c 3 Selected from 0, 1 or 2; when two or more R's are present 6 When two or more R' s 6 Are the same as or different from each other.
More preferably, the L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Independently selected from single bond or the followingOne of the groups:
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the R is 6 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, carbazolyl, a group of formula II; or two adjacent R 6 Can be connected with each other to form a substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring or C3-C8 aliphatic ring;
The R is j Selected from one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, a group of formula II;
the R is k 、R l Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl,Terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, a group of formula II;
the R is n Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl;
The c 1 Selected from 0, 1, 2, 3 or 4; the c 2 Selected from 0, 1, 2 or 3; the c 3 Selected from 0, 1 or 2; the c 4 Selected from 0, 1, 2, 3, 4, 5 or 6; the c 5 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the c 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 6 When two or more R' s 6 Are the same as or different from each other.
The R is 6 、R j 、R k 、R l 、R n The substituent "substituted or unsubstituted" in (a) is selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, and when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, the structure shown in the formula I contains one or more groups shown in the formula II.
Preferably, the structure shown in the formula I contains one, two, three, four, five, six or more groups shown in the formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Containing one or more groups of formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Containing one or more groups of formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Containing one, two, three or more groups of formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 And contains one, two, three, four, five, six or more groups of formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Each independently comprising one, two, three, four, five or six groups of formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Each independently of the others, one, two, three, four, five or six of which contains one, two or three groups of the formula II.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Each independently comprising a group of formula II.
Preferably, R 5 One, two, three, four, five, six or more of which are independently selected from the group of formula II.
Preferably Ar 1 R of (2) 5 One or both of which are independently selected from the group represented by formula II.
Preferably Ar 2 R of (2) 5 One or both of which are independently selected from the group represented by formula II.
Preferably Ar 3 R of (2) 5 One or both of which are independently selected from the group represented by formula II.
Preferably Ar 4 R of (2) 5 One or both of which are independently selected from the group represented by formula II.
Preferably Ar 5 R of (2) 5 One or both of which are independently selected from the group represented by formula II.
Preferably Ar 6 R of (2) 5 One or both of which are independently selected from the group represented by formula II.
Preferably Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 One, two, three, four, five or six of each R 5 One or both of which are independently selected from the group represented by formula II.
Preferably, the L 1 、L 2 、L 3 、L 4 、L 5 、L 6 Containing one or more groups of formula II.
Preferably, the L, L a 、L b 、L c Containing one or more groups of formula II.
Most preferably, the triarylamine compound is selected from any one of the following structures:
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the triarylamine compounds of formula I of the present invention are shown in the above description in some specific structural forms, but the present invention is not limited to these chemical structures, and substituents are included in the compounds of formula I based on the structures of formula I.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or outside one or more than one of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds.
The organic layer comprises a hole transmission region, a luminescent layer, an electron transmission region and a covering layer, wherein the hole transmission region comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a luminescent auxiliary layer and other functional layers, the electron transmission region comprises a hole blocking layer, an electron transmission layer, an electron injection layer and other functional layers, and the organic functional layers can be correspondingly increased or decreased according to actual needs. As the organic layer according to the present invention, it may have a single-layer structure and a multi-layer structure. The single layer structure includes a single layer containing a single material or includes a single layer containing a plurality of materials; the multi-layer structure includes a plurality of layers comprising a plurality of materials. For example, the hole transport layer may include a first hole transport layer and a second hole transport layer, and the electron transport layer may include a first electron transport layer and a second electron transport layer;
preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region including any one or a combination of at least two of the triarylamine compounds described in the present invention.
Preferably, the hole transport region comprises an electron blocking layer, and the electron blocking layer contains any one or a combination of at least two of the triarylamine compounds disclosed by the invention.
Preferably, the hole transport region comprises a hole transport layer, and the hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.
Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the hole injection layer and the light emitting layer, the second hole transport layer is located between the first hole transport layer and the light emitting layer, and at least one of the first hole transport layer and the second hole transport layer contains any one or a combination of at least two of the triarylamine compounds.
Preferably, the organic layer is located outside one or more of the anode and the cathode, and the organic layer includes a coating layer including any one or a combination of at least two of the triarylamine compounds of the present invention.
Preferably, the cover layer is located outside the cathode.
The material of each layer of thin film in the organic electroluminescent device is not particularly limited, and materials known in the art can be used. The following describes each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device, respectively:
The organic electroluminescent device of the present invention is generally formed on a substrate. As the substrate, a material having good stability is preferable as a connection point between the organic electroluminescent device and the external circuit, and a common substrate material is glass, resin, silicon, metal foil, or the like, but is not limited thereto.
The anode material according to the present invention preferably has a high work function material. Specific examples of the anode material that can be used in the present invention may include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO); combinations of metals and oxides, such as ITO-Ag-ITO; conductive polymers such as poly (3-methylthiophene), polypyrrole, polyaniline, poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), and the like, but are not limited thereto.
The hole injection material of the present invention is preferably a material having a good hole accepting ability. Specific examples of the hole injecting material that can be used in the present invention may include: silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, other metal oxides, phthalocyanine compounds, biphenylamine compounds, phenazine compounds, other materials, such as copper phthalocyanine (CuPc), titanyl phthalocyanine, N ' -diphenyl-N, N ' -di- [4- (N, N-diphenylamine) phenyl ] benzidine (NPNPB), N ' -tetra (4-methoxyphenyl) benzidine (MeO-TPD), and bisquinoxalino [2,3-a:2',3' -c ] phenazine (HATNA), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like, but are not limited thereto.
The hole transport layer material according to the present invention is preferably a material having high hole mobility. The hole transporting material that can be used in the present invention may be selected from materials such as diphenylamine compound, triphenylamine compound, fluorene compound, carbazole compound, etc., for example, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -bis (naphthalen-1-yl) -N, N ' -bis (phenyl) -2,2' -dimethylbenzidine (α -NPD), N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), 4- [1- [4- [ bis (4-methylphenyl) amino ] phenyl ] cyclohexyl ] -N- (3-methylphenyl) -N- (4-methylphenyl) aniline (TAPC), etc., but is not limited thereto.
The luminescent layer material comprises a luminescent layer main body material and a luminescent layer doping material. The mass ratio of the host material to the doping material is preferably (90-99.5): 0.5-10. The host material of the light emitting layer may be selected from 4,4' -bis (9-Carbazole) Biphenyl (CBP), 4' -bis (9-carbazolyl) -2,2' -dimethylbiphenyl (CDBP), 9' - (2, 6-pyridyldiyl-3, 1-phenylene) bis-9H-carbazole (26 DCZPPY), 9' -diphenyl-9H, 9' H-3,3' -bicarbazole (BCzPh), 9- (5- (3- (9H-carbazol-9-yl) phenyl) pyridin-3-yl) -9H-carbazole (CPPyC), 4' -bis (carbazol-9-yl) -2,2' -dimethylbiphenyl (CDBP), 1, 3-bis (N-carbazolyl) benzene (MCP), 9-dimethyl-N, N-diphenyl-7- (4- (1-phenyl-1H benzo [ d ]) ]Imidazol-2-yl) phenyl) -9H-fluoren-2-amine (EFIN), 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-tert-butyl-9, 10-bis (2-naphthyl) anthracene (TBADN), 1- (7- [9,9' -dianthracene]-10-yl-9, 9-dioctyl-9H-fluoren-2-yl) pyrene (BAnF 8 Pye), 9,9,9',9' -tetra (4-methylphenyl) -2,2' -bi-9H-fluorene (BDAF), tris (8-hydroxyquinoline) aluminum (Alq 3), bis (10-hydroxybenzo [ H ]]Quinoline) beryllium (BeBq 2), bis (8-hydroxyquinoline) zinc (Znq 2), and the like, but is not limited thereto. The doping material of the light emitting layer can be selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA) and 4,4' -bis [4- (diphenylamino) styryl)]Biphenyl (BDAVBi), 4' -di [4- (di-p-tolylamino) styryl]Diphenyl (DPAVBi), bis (2-hydroxyphenylpyridine) beryllium (Bepp 2), bis (4, 6-difluorophenylpyridine-C2, N) iridium picolinate (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq) 3 ) Bis (1-phenyliso)Quinoline) (acetylacetonato) iridium (Ir (piq) 2 (acac)) and the like, but is not limited thereto.
The electron transport layer material according to the present invention is preferably a material having high electron mobility. Specific examples of the electron transport material usable in the present invention include: imidazoles, triazoles, phenanthroline derivatives, quinolines and the like, such as 2,9- (dimethyl) -4, 7-biphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris [ (3-pyridyl) -phenyl ] benzene (TmPyPB), 4' -bis (4, 6-diphenyl-1, 3, 5-triazinyl) biphenyl (BTB), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 2- (naphthalen-2-yl) -4,7- (diphenyl) -1, 10-phenanthroline (hnephen), 8-hydroxyquinoline-lithium and the Like (LiQ), and the like, but are not limited thereto.
The electron injection material of the present invention is preferably a material having a good electron injection ability, which can reduce the interface barrier between the cathode and the electron transport layer. Specific examples of the electron injecting material usable in the present invention may include: alkali metal salts (e.g., liF, csF), alkaline earth metal salts (e.g., mgF) 2 ) Metal oxides (such as Al 2 O 3 、MoO 3 ) But is not limited thereto.
The cathode material according to the present invention is preferably a material having a low work function. Specific examples of the cathode material that can be used in the present invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metallic materials, e.g. LiF/Al, mg/Ag, li/Al, liO 2 /Al、BaF 2 Al, etc., but is not limited thereto.
The cover layer material of the present invention preferably has a high glass transition temperature and excellent light extraction performance. The capping material usable in the present invention may be selected from the group consisting of carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, and the like, in addition to the triarylamine-based compounds described in the present invention, but is not limited thereto.
The thickness of each organic layer of the organic electroluminescent device is not particularly limited, and may be any thickness commonly used in the art.
The method for producing the thin films of each layer in the organic electroluminescent device of the present invention is not particularly limited, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, vapor deposition, etc. may be used, but are not limited thereto.
The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, indication boards, signal lamps, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors and the like, but is not limited to the fields.
Synthetic examples
The preparation method of the triarylamine compound shown in the formula I is not particularly limited, and can be adopted by one skilled in the art
Well known methods of preparation. For example, the preparation may be performed using the synthetic route shown below, but the present invention is not limited thereto:
the Xa, xb and Xc are independently selected from any one of I, br and Cl.
Raw materials and reagent description: the starting materials or reagents used in the following synthetic examples are not particularly limited and may be commercially available products or prepared by methods well known to those skilled in the art.
Instrument: g2—si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk); vario EL cube organic element analyzer (Elementar, germany).
Synthesis example 1: preparation of starting materials a-136
I-136 (24.71 g,60 mmol), j-136 (9.38 g,60 mmol), pd (PPh) were added to the flask under nitrogen 3 ) 4 (0.69 g,0.60 mmol) and K 2 CO 3 (24.88g,180 mmol) and 300mL of toluene/ethanol/water (2:1:1) mixed solvent, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 4h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing and separated, the organic layer was collected and dried over anhydrous magnesium sulfate, filtration was performed, the filtrate was concentrated by distillation under reduced pressure, and recrystallization was performed with ethyl acetate, so that raw material a-136 (18.08 g, yield: 76%) was obtained after drying, and the purity of the solid was not less than 99.81% by HPLC detection. Mass spectrum m/z:3393.8771 (theory: 393.8760).
The raw materials a were subjected to corresponding replacement, and the raw materials a-136 were prepared according to the preparation method of the raw materials a-136 of synthetic example 1, and the raw materials are shown in the following table:
synthesis example 2: preparation of raw material b-4
E-4 (10.24 g,110.00 mmol), f-4 (24.99 g,110.00 mmol), sodium tert-butoxide (21.14 g,220.00 mmol), pd (dppf) Cl were added to the flask under nitrogen 2 (0.95 g,1.30 mmol) and 550ml toluene, and the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing and separated, the organic layer was collected and dried over anhydrous magnesium sulfate, filtration was performed, the filtrate was concentrated by distillation under reduced pressure, and recrystallization was performed with ethyl acetate, and the material b-4 (21.85 g, 83%) was obtained after drying, and the purity of the solid was not less than 99.75% by HPLC detection. Mass spectrum m/z:239.1689 (theory: 239.1674).
The raw materials are correspondingly replaced, and the raw materials b/c can be prepared according to the preparation method of the raw material b-1 in the synthesis example 2, wherein the raw materials are shown in the following table:
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synthesis example 3: preparation of Compound 4
Preparation of intermediate A-4:
a-4 (12.82 g,40.00 mmol), b-4 (19.15 g,80.00 mmol), pd (OAc) were added to the flask under nitrogen 2 (0.20g，0.90mmol)、P(t-Bu) 3 (3.20 mL of a 0.5M toluene solution, 1.60 mmol), naOt-Bu (15.38 g,160.00 mmol) and 400mL of toluene solvent, the mixture was stirred, and the mixture of the above reactants was heated under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left to stand, an organic layer was collected, dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, and recrystallized from toluene to give intermediate A-4 (20.14 g, yield 79%) having an HPLC purity of 99.87%. Mass spectrum m/z:636.3281 (theory: 636.3271).
Preparation of Compound 4:
the reaction flask was charged with intermediate A-4 (12.75 g,20.00 mmol), c-4 (4.83 g,20.00 mmol), pd under nitrogen 2 (dba) 3 (0.27 g,0.30 mmol), X-Phos (0.29 g,0.60 mmol), naOt-Bu (3.84 g,40.00 mmol) and 100ml toluene solvent, and the mixture was stirred and the mixed solution of the above reactants was heated under reflux for 7 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, and recrystallizing with toluene to obtain compound 4 (12.63 g, 75%) with HPLC purity of > 99.97%. Mass spectrum m/z:841.4775 (theoretical value: 8) 41.4791). Theoretical element content (%) C 59 H 63 N 3 Si: c,84.14; h,7.54; n,4.99. Measured element content (%): c,84.16; h,7.51; n,5.03.
Synthesis example 4: preparation of Compound 20
A-20 (7.30 g,20.00 mmol), c-20 (14.79 g,60.00 mmol), pd were added to the flask under nitrogen 2 (dba) 3 (0.69 g,0.75 mmol), X-Phos (0.72 g,1.50 mmol), naOt-Bu (11.53 g,120.00 mmol) and 300ml toluene solvent, and the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 6 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, and recrystallizing with toluene to obtain the compound 20 (13.09 g, 76%) with HPLC purity of 99.96%. Mass spectrum m/z:860.4971 (theory: 860.4958). Theoretical element content (%) C 55 H 44 D 15 N 3 Si 3 : c,76.69; h,8.66; n,4.88; . Measured element content (%): c,76.72; h,8.68; n,4.87; .
Synthesis example 5: preparation of Compound 24
Preparation of intermediate B-24:
a-24 (11.60 g,40.00 mmol), c-4 (14.38 g,40.00 mmol), pd (OAc) were added to the flask under nitrogen 2 (0.11g，0.50mmol)、P(t-Bu) 3 (2.00 mL of a 0.5M toluene solution, 1.00 mmol), naOt-Bu (9.61 g,100.00 mmol) and 200mL of toluene solvent, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 5 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for separating liquid, and collecting dry organic layer with anhydrous magnesium sulfate Drying, filtration, distillation under reduced pressure, concentration of the filtrate and recrystallization from toluene gave intermediate B-24 (18.20 g, 80% yield) with HPLC purity ≡ 99.83%. Mass spectrum m/z:567.1902 (theory: 567.1916).
Preparation of compound 24:
the reaction flask was charged with intermediate B-24 (11.37 g,20.00 mmol), B-24 (6.77 g,40.00 mmol), pd under nitrogen 2 (dba) 3 (0.46 g,0.50 mmol), X-Phos (0.48 g,1.00 mmol), naOt-Bu (9.61 g,100.00 mmol) and 200ml toluene solvent, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 6 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, and recrystallizing with toluene to obtain compound 4 (12.51 g, 75%) with HPLC purity of > 99.97%. Mass spectrum m/z:833.4182 (theory: 833.4165). Theoretical element content (%) C 59 H 55 N 3 Si: c,84.95; h,6.65; n,5.04. Measured element content (%): c,85.01; h,6.63; n,5.03.
Synthesis example 6: preparation of Compound 46
According to the preparation method of Synthesis example 3, b-4 was replaced with equimolar b-46 and c-4 was replaced with equimolar c-46 to obtain Compound 46 (13.21 g), with HPLC purity of ≡99.98%. Mass spectrum m/z:929.4175 (theory: 929.4165). Theoretical element content (%) C 67 H 55 N 3 Si: c,86.50; h,5.96; n,4.52. Measured element content (%): c,86.46; h,5.99; n,4.55.
Synthesis example 7: preparation of Compound 64
Following the procedure for the preparation of Synthesis example 3, a-4 was replaced with equimolar onea-64, b-4 was replaced with equimolar c-64, and c-4 was replaced with equimolar b-24 to give compound 64 (13.15 g), with an HPLC purity of ≡99.98%. Mass spectrum m/z:925.4261 theory: 925.4248). Theoretical element content (%) C 64 H 59 N 3 Si 2 : c,82.98; h,6.42; n,4.54. Measured element content (%): c,83.03; h,6.39; n,4.56.
Synthesis example 8: preparation of Compound 72
According to the preparation method of Synthesis example 5, substituting a-24 with equimolar a-72 and substituting c-24 with equimolar c-72, compound 72 (12.47 g) was obtained with HPLC purity of ≡99.98%. Mass spectrum m/z:853.3843 (theory: 853.3852). Theoretical element content (%) C 61 H 51 N 3 Si: c,85.77; h,6.02; n,4.92. Measured element content (%): c,85.73; h,6.05; n,4.96.
Synthesis example 9: preparation of Compound 82
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-82, substituting b-4 with equimolar c-82, and substituting c-4 with equimolar b-24, compound 82 (12.76 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:873.3949 (theory: 873.3935). Theoretical element content (%) C 60 H 55 N 3 Si 2 : c,82.43; h,6.34; n,4.81. Measured element content (%): c,82.46; h,6.32; n,4.79.
Synthesis example 10: preparation of Compound 87
Following the procedure for the preparation of Synthesis example 3, a-4 was substitutedFor equimolar a-87, b-4 was replaced with equimolar b-87 and c-4 was replaced with equimolar c-87 to give compound 87 (12.18 g) with an HPLC purity of ≡99.97%. Mass spectrum m/z:811.4159 (theory: 811.4167). Theoretical element content (%) C 57 H 37 D 10 N 3 Si: c,84.30; h,7.07; n,5.17. Measured element content (%): c,84.27; h,7.11; n,5.20.
Synthesis example 11: preparation of Compound 100
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-100, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-100, compound 100 (12.27 g) was obtained with HPLC purity ≡ 99.98%. Mass spectrum m/z:817.3864 (theory: 817.3852). Theoretical element content (%) C 58 H 51 N 3 Si: c,85.15; h,6.28; n,5.14. Measured element content (%): c,85.16; h,6.32; n,5.11.
Synthesis example 12: preparation of Compound 103
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-103, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-103, compound 103 (13.19 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:941.4181 (theory: 941.4165). Theoretical element content (%) C 68 H 55 N 3 Si: c,86.68; h,5.88; n,4.46. Measured element content (%): c,86.71; h,5.92; n,4.43.
Synthesis example 13: preparation of Compound 104
Preparation of intermediate C-104:
a-104 (22.04 g,60.00 mmol), b-24 (10.15 g,60.00 mmol), pd (dppf) Cl were added to the flask under nitrogen 2 (0.55 g,0.75 mmol), naOt-Bu (11.53 g,120.00 mmol) and 300ml toluene solvent, and the mixture was stirred, and the mixture of the above reactants was heated under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing and separated, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, and recrystallized from toluene to give intermediate C-104 (20.35 g, 83%) having an HPLC purity of ≡ 99.76%. Mass spectrum m/z:407.0087 (theory: 407.0076).
Preparation of intermediate D-104:
into a reaction flask was charged intermediate C-104 (16.35 g,40.00 mmol), C-4 (9.66 g,40.00 mmol), pd (OAc) under nitrogen 2 (0.11g，0.50mmol)、P(t-Bu) 3 (2.00 mL of a 0.5M toluene solution, 1.00 mmol), naOt-Bu (9.61 g,100.00 mmol) and 200mL of toluene solvent, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 5 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, and recrystallizing with toluene to obtain an intermediate D-104 (18.22 g, 80%) with HPLC purity of 99.85%. Mass spectrum m/z:568.2115 (theory: 568.2102).
Preparation of compound 104:
the reaction flask was charged with intermediate D-104 (11.38 g,20.00 mmol), D-104 (8.15 g,20.00 mmol), pd under nitrogen 2 (dba) 3 (0.27 g,0.30 mmol), X-Phos (0.29 g,0.60 mmol), naOt-Bu (3.84 g,40.00 mmol) and 100ml toluene solvent, and the mixture was stirred and the mixed solution of the above reactants was heated under reflux for 7 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added, the mixture was extracted with methylene chloride, the mixture was left standing and separated, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and recrystallized from toluene to give compound 104 (13.16 g, 75%) having an HPLC purity of ∈ 99.94%. Mass spectrum m/z:939.4027 (theoretical value: 939.4009). Theoretical element content (%) C 68 H 53 N 3 Si: c,86.86; h,5.68; n,4.47. Measured element content (%): c,86.88; h,5.71; n,4.45.
Synthesis example 14: preparation of Compound 127
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-127, substituting b-4 with equimolar c-4, and substituting c-4 with equimolar b-127, compound 127 (12.72 g) was obtained with HPLC purity ≡ 99.95%. Mass spectrum m/z:870.4180 (theory: 870.4167). Theoretical element content (%) C 58 H 46 D 7 N 3 OSi 2 : c,79.95; h,6.94; n,4.82. Measured element content (%): c,79.93; h,6.99; n,4.81.
Synthesis example 15: preparation of Compound 136
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-136, substituting b-4 with equimolar c-4, and substituting c-4 with equimolar b-136, compound 136 (13.47 g) was obtained with HPLC purity ≡ 99.95%. Mass spectrum m/z:975.4415 (theory: 975.4404). Theoretical element content (%) C 68 H 61 N 3 Si 2 : c,83.65; h,6.30; n,4.30. Measured element content (%): c,83.70; h,6.26; n,4.27.
Synthesis example 16: preparation of Compound 177
According to the preparation method of Synthesis example 5, substituting a-24 with equimolar a-177 and substituting c-24 with equimolar c-177, compound 177 (12.75 g) was obtained with HPLC purity ≡ 99.96%. Mass spectrum m/z:884.4279 (theory: 884.4292). Theoretical element content (%) C 63 H 44 D 7 N 3 Si: c,85.48; h,6.60; n,4.75. Measured element content (%): c,85.51; h,6.58; n,4.79.
Synthesis example 17: preparation of Compound 212
According to the preparation method of Synthesis example 5, substituting a-24 with equimolar a-212 and substituting c-24 with equimolar c-212, compound 212 (13.02 g) was obtained with an HPLC purity of ≡99.94%. Mass spectrum m/z:903.4017 (theory: 903.4009). Theoretical element content (%) C 65 H 53 N 3 Si: c,86.34; h,5.91; n,4.65. Measured element content (%): c,86.36; h,5.88; n,4.68.
Synthesis example 18: preparation of Compound 223
According to the preparation method of Synthesis example 3, substituting a-20 with equimolar a-223 and substituting c-20 with equimolar c-4, compound 223 (13.25 g) was obtained with an HPLC purity of ≡99.96%. Mass spectrum m/z:945.4345 (theory: 945.4330). Theoretical element content (%) C 63 H 63 N 3 Si 3 : c,79.95; h,6.71; n,4.44. Measured element content (%): c,79.98; h,6.69; n,4.47.
Synthesis example 19: preparation of Compound 233
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-233, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-233, compound 233 (13.18 g) was obtained with an HPLC purity of ≡ 99.96%. Mass spectrum m/z:927.3633 (theory: 927.3645). Theoretical element content (%) C 66 H 49 N 3 OSi: c,85.40; h,5.32; n,4.53. Measured element content (%): c,85.36; h,5.29; n,4.57.
Synthesis example 20: preparation of Compound 267
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-267, substituting b-4 with equimolar c-4, and substituting c-4 with equimolar b-267, compound 267 (13.28 g) was obtained with HPLC purity ≡ 99.98%. Mass spectrum m/z:947.4651 (theory: 947.4666). Theoretical element content (%) C 64 H 65 N 3 OSi 2 : c,81.05; h,6.91; n,4.43. Measured element content (%): c,81.09; h,6.88; n,4.46.
Synthesis example 21: preparation of Compound 279
Following the procedure for the preparation of Synthesis example 3, substituting a-4 with equimolar a-279, substituting b-4 with equimolar b-279, and substituting c-4 with equimolar c-46, compound 279 (13.21 g) was obtained with an HPLC purity of ≡99.98%. Mass spectrum m/z:929.4756 (theory: 929.4740). Theoretical element content (%) C 65 H 63 N 3 OSi: c,83.92; h,6.83; n,4.52. Measured element content (%): c,83.95; h,6.81; n,4.55.
Synthesis example 22: preparation of Compound 282
Following the procedure for the preparation of Synthesis example 3 substituting a-4 with equimolar a-267 and b-4 with equimolar b-282, compound 282 (12.88 g) was obtained,HPLC purity. Mass spectrum m/z:893.3813 (theory: 893.3801). Theoretical element content (%) C 63 H 51 N 3 OSi: c,84.62; h,5.75; n,4.70. Measured element content (%): c,84.65; h,5.77; n,4.69.
Synthesis example 23: preparation of Compound 292
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-233 and b-4 with equimolar b-292, compound 292 (12.70 g) was obtained with HPLC purity of ≡99.98%. Mass spectrum m/z:893.3815 (theory: 893.3801). Theoretical element content (%) C 63 H 51 N 3 OSi: c,84.62; h,5.75; n,4.70. Measured element content (%): c,84.64; h,5.78; n,4.67.
Synthesis example 24: preparation of Compound 318
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-318, substituting b-4 with equimolar b-282, and substituting c-4 with equimolar c-46, compound 318 (13.39 g) was obtained with an HPLC purity of ≡ 99.98%. Mass spectrum m/z:969.4126 (theory: 969.4114). Theoretical element content (%) C 69 H 55 N 3 OSi: c,85.41; h,5.71; n,4.33. Measured element content (%): c,85.38; h,5.69; n,4.37.
Synthesis example 25: preparation of Compound 348
According to the preparation method of Synthesis example 5, substituting a-24 with equimolar a-348 and substituting c-24 with equimolar c-348, compound 348 (13.15 g) was obtained with HPLC purity ≡ 99.94%. Mass spectrum m/z:925.4441 (theory: 925.4427). Theoretical element content (%) C 65 H 59 N 3 OSi: c,84.28; h,6.42; n,4.54. Measured element content (%): c,84.32; h,6.45; n,4.51.
Synthesis example 26: preparation of Compound 361
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-361, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-361, compound 361 (12.93 g) was obtained with HPLC purity ≡ 99.95%. Mass spectrum m/z:909.4104 (theory: 909.4114). Theoretical element content (%) C 64 H 55 N 3 OSi: c,84.45; h,6.09; n,4.62. Measured element content (%): c,84.46; h,6.11; n,4.63.
Synthesis example 27: preparation of Compound 367
According to the production method of Synthesis example 3, a-4 was replaced with equimolar a-267, b-4 was replaced with equimolar b-367, and c-4 was replaced with equimolar c-367, whereby Compound 367 (12.88 g) was obtained, and HPLC purity was. Mass spectrum m/z:893.4214 (theory: 893.4197). Theoretical element content (%) C 60 H 59 N 3 OSi 2 : c,80.58; h,6.65; n,4.70. Measured element content (%): c,80.61; h,6.66; n,4.68.
Synthesis example 28: preparation of Compound 385
According to the preparation method of Synthesis example 3, a-4 was replaced with equimolar a-267, b-4 was replaced with equimolar b-24, and c-4 was replaced with equimolar b-24c-385, compound 385 (13.56 g) was obtained with an HPLC purity of ≡ 99.98%. Mass spectrum m/z:981.4127 (theory: 981.4114). Theoretical element content (%) C 70 H 55 N 3 OSi: c,85.59; h,5.64; n,4.28. Measured element content (%): c,85.61; h,5.66; n,4.27.
Synthesis example 29: preparation of Compound 390
According to the preparation method of Synthesis example 3, A-4 was replaced with equimolar A-233 and c-4 was replaced with equimolar c-390 to obtain compound 390 (13.11 g), with HPLC purity of ≡99.97%. Mass spectrum m/z:949.4415 (theory: 949.4427). Theoretical element content (%) C 67 H 59 N 3 OSi: c,84.68; h,6.26; n,4.42. Measured element content (%): c,84.72; h,6.31; n,4.37.
Synthesis example 30: preparation of Compound 394
Following the procedure for the preparation of synthetic example 3, substituting a-4 with equimolar a-267, substituting b-4 with equimolar c-394 and substituting c-4 with equimolar b-394 gave compound 394 (13.18 g) having an HPLC purity of > 99.96%. Mass spectrum m/z:940.3978 (theory: 940.3993). Theoretical element content (%) C 63 H 56 N 4 OSi 2 : c,80.38; h,6.00; n,5.95. Measured element content (%): c,80.43; h,5.98; n,5.96.
Synthesis example 31: preparation of Compound 399
According to the preparation method of Synthesis example 3, A-4 was replaced with equimolar A-385 and c-4 was replaced with equimolar c-399 to obtainTo compound 399 (12.53 g), HPLC purity was ≡ 99.98%. Mass spectrum m/z:857.3451 (theory: 857.3438). Theoretical element content (%) C 59 H 47 N 3 O 2 Si: c,82.58; h,5.52; n,4.90. Measured element content (%): c,82.61; h,5.56; n,4.87.
Synthesis example 32: preparation of Compound 413
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-233, substituting b-4 with equimolar c-4, and substituting c-4 with equimolar b-413, compound 413 (13.25 g) was obtained with HPLC purity ≡ 99.98%. Mass spectrum m/z:945.3622 (theory: 945.3604). Theoretical element content (%) C 62 H 55 N 3 OSSi 2 : c,78.69; h,5.86; n,4.44. Measured element content (%): c,78.65; h,5.91; n,4.41.
Synthesis example 33: preparation of Compound 425
Following the procedure for the preparation of Synthesis example 13 substituting a-104 with equimolar a-425, c-4 with equimolar c-425 and d-104 with equimolar d-425, compound 425 (13.12 g) was obtained with an HPLC purity of > 99.95%. Mass spectrum m/z:923.3918 (theory: 923.3907). Theoretical element content (%) C 64 H 53 N 3 O 2 Si: c,83.17; h,5.78; n,4.55. Measured element content (%): c,83.20; h,5.81; n,4.53.
Synthesis example 34: preparation of Compound 427
Following the procedure for the preparation of Synthesis example 3, a-4 was replaced with equimolar oneSubstitution of b-4 for equimolar b-427 on molar a-233 gave compound 427 (12.91 g) with an HPLC purity of ≡99.97%. Mass spectrum m/z:921.3371 (theory: 921.3387). Theoretical element content (%) C 63 H 47 N 3 O 3 Si: c,82.06; h,5.14; n,4.56. Measured element content (%): c,82.11; h,5.12; n,4.55.
Synthesis example 35: preparation of Compound 430
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-279, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-430, compound 430 (13.00 g) was obtained with HPLC purity ≡ 99.97%. Mass spectrum m/z:927.3626 (theory: 927.3617). Theoretical element content (%) C 63 H 45 D 4 N 3 OSSi: c,81.52; h,5.75; n,4.53. Measured element content (%): c,81.53; h,5.76; n,4.56.
Synthesis example 36: preparation of Compound 432
According to the preparation method of Synthesis example 3, a-4 was replaced with equimolar a-432, b-4 was replaced with equimolar b-24, and c-4 was replaced with equimolar c-432, to obtain Compound 432 (12.94 g), with HPLC purity ≡ 99.96%. Mass spectrum m/z:910.4025 (theory: 910.4005). Theoretical element content (%) C 63 H 46 D 4 N 4 OSi: c,83.04; h,5.97; n,6.15. Measured element content (%): c,83.06; h,6.01; n,6.12.
Synthesis example 37: preparation of Compound 433
According to synthesisThe procedure for the preparation of example 3, substituting A-4 with equimolar A-233 and substituting c-4 with equimolar c-433, gave compound 433 (13.55 g) with an HPLC purity of > 99.93%. Mass spectrum m/z:995.3921 (theory: 995.3907). Theoretical element content (%) C 70 H 53 N 3 O 2 Si: c,84.39; h,5.36; n,4.22. Measured element content (%): c,84.41; h,5.40; n,4.21.
Synthesis example 38: preparation of Compound 441
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-441, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-441, compound 441 (13.42 g) was obtained with HPLC purity ≡ 99.95%. Mass spectrum m/z:957.3739 (theory: 957.3751). Theoretical element content (%) C 67 H 51 N 3 O 2 Si: c,83.98; h,5.36; n,4.39. Measured element content (%): c,84.01; h,5.32; n,4.42.
Synthesis example 39: preparation of Compound 460
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-460, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-46, compound 460 (13.39 g) is obtained with HPLC purity ≡ 99.96%. Mass spectrum m/z:983.3919 (theory: 983.3907). Theoretical element content (%) C 69 H 53 N 3 O 2 Si: c,84.20; h,5.43; n,4.27. Measured element content (%): c,84.23; h,5.45; n,4.26.
Synthesis example 40: preparation of Compound 560
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-560, substituting b-4 with equimolar b-24, and substituting c-4 with equimolar c-560, compound 560 (13.72 g) was obtained with HPLC purity ≡ 99.94%. Mass spectrum m/z:1007.4655 (theory: 1007.4668). Theoretical element content (%) C 70 H 65 N 3 SSi: c,83.37; h,6.50; n,4.17. Measured element content (%): c,83.41; h,6.47; n,4.21.
Synthesis example 41: preparation of Compound 588
According to the preparation method of Synthesis example 3, a-4 was replaced with equimolar a-588, b-4 was replaced with equimolar b-87, and c-4 was replaced with equimolar c-588, to give compound 588 (13.07 g), and the HPLC purity was > 99.95%. Mass spectrum m/z:932.4162 (theory: 932.4153). Theoretical element content (%) C 63 H 40 D 10 N 4 SSi: c,81.07; h,6.48; n,6.00. Measured element content (%): c,81.05; h,6.51; n,6.01.
Synthesis example 42: preparation of Compound 613
According to the preparation method of Synthesis example 3, substituting a-4 with equimolar a-613, substituting b-4 with equimolar c-4, and substituting c-4 with equimolar b-613, compound 613 (12.90 g) was obtained with HPLC purity ≡ 99.96%. Mass spectrum m/z:920.4732 (theory: 920.4718). Theoretical element content (%) C 63 H 56 D 5 N 3 Si 2 : c,82.12; h,7.22; n,4.56. Measured element content (%): c,82.13; h,7.25; n,4.54.
Synthesis example 43: preparation of Compound 636
According to the preparation method of Synthesis example 5, substituting a-24 with equimolar a-636 and substituting c-24 with equimolar c-4, compound 636 (12.29 g) was obtained with an HPLC purity of ≡99.97%. Mass spectrum m/z:889.3866 (theory: 889.3852). Theoretical element content (%) C 64 H 45 N 3 Si: c,86.35; h,5.77; n,4.72. Measured element content (%): c,86.37; h,5.78; n,4.73.
Synthesis example 44: preparation of Compound 642
According to the preparation method of Synthesis example 4, substituting a-20 with equimolar a-642 and substituting c-20 with equimolar c-4, compound 642 (14.08 g) was obtained with HPLC purity of ≡99.92%. Mass spectrum m/z:1049.4574 (theory: 1049.4592). Theoretical element content (%) C 70 H 67 N 3 OSi 3 : c,80.03; h,6.43; n,4.00. Measured element content (%): c,80.05; h,6.41; n,4.05.
Synthesis example 45: preparation of Compound 656
According to the preparation method of Synthesis example 4, substituting a-20 with equimolar a-656 and substituting c-20 with equimolar c-4, compound 656 (13.27 g) with HPLC purity of > 99.95% is obtained. Mass spectrum m/z:960.4451 (theory: 960.4439). Theoretical element content (%) C 63 H 64 N 4 Si 3 : c,78.70; h,6.71; n,5.83. Measured element content (%): c,78.65; h,6.74; n,5.88.
Synthesis example 46: preparation of Compound 668
Following the procedure for the preparation of Synthesis example 5 substituting a-24 with equimolar a-668 and c-24 with equimolar c-668, compound 668 (12.89 g) was obtained with an HPLC purity of ≡99.96%. Mass spectrum m/z:933.3847 (theory: 933.3863). Theoretical element content (%) C 64 H 51 N 5 OSi: c,82.28; h,5.50; n,7.50. Measured element content (%): c,82.30; h,5.53; n,7.49.
Synthesis example 47: preparation of Compound 713
According to the preparation method of Synthesis example 5, substituting a-24 with equimolar a-713 and substituting c-24 with equimolar c-713, compound 713 (12.45 g) was obtained with an HPLC purity of ≡99.98%. Mass spectrum m/z:840.3743 (theory: 840.3728). Theoretical element content (%) C 60 H 44 D 3 N 3 Si: c,85.67; h,5.99; n,5.00. Measured element content (%): c,85.69; h,6.03; n,4.97.
Comparative example 1 device preparation example: (hole transporting layer)
Comparative example 1: firstly, placing a glass substrate on which ITO/Ag/ITO is evaporated in distilled water for cleaning for 2 times, washing for 30 minutes by ultrasonic waves, repeatedly cleaning for 2 times by using distilled water, washing by ultrasonic waves for 10 minutes, after the distilled water is cleaned, sequentially washing by using isopropanol, acetone and methanol solvents by ultrasonic waves, drying on a hot plate heated to 120 ℃, transferring to a plasma cleaning machine after drying, and transferring the substrate to a vapor deposition machine after washing for 5 minutes.
The method comprises the steps of evaporating HI-1 serving as a hole injection layer on a cleaned ITO/Ag/ITO substrate to obtain an evaporation thickness of 12nm, evaporating a contrast compound 1 serving as a hole transport layer on the hole injection layer to obtain an evaporation thickness of 56nm, evaporating a mixture (mass ratio of 95:5) of BH-1 and BD-1 in vacuum on the hole transport layer to form a light-emitting layer to obtain an evaporation thickness of 40nm, evaporating ET-1 and Liq (mass ratio of 1:1) serving as electron transport layers on the light-emitting layer to obtain an evaporation thickness of 35nm, evaporating LiF serving as the electron injection layer on the electron transport layer to obtain an evaporation thickness of 1nm, evaporating Mg: ag (mass ratio of 1:9) serving as a cathode on the electron injection layer to obtain an evaporation thickness of 15nm, and evaporating CP-1 serving as a cover layer on the cathode in vacuum to obtain an organic electroluminescent device (the material structure of each functional layer in the organic electroluminescent device is shown in the following diagram).
Examples 1 to 30
The hole transporting layer material of the organic electroluminescent device was replaced with the compound 4, the compound 20, the compound 46, the compound 64, the compound 72, the compound 87, the compound 100, the compound 104, the compound 127, the compound 136, the compound 177, the compound 212, the compound 233, the compound 267, the compound 279, the compound 282, the compound 292, the compound 318, the compound 367, the compound 385, the compound 390, the compound 399, the compound 427, the compound 430, the compound 441, the compound 460, the compound 560, the compound 588, the compound 613, the compound 642 in this order, and the other steps were the same as those of comparative example 1.
Test software, a computer, a K2400 digital source list manufactured by Keithley company in U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company in U.S. are combined into a combined IVL test system to test the driving voltage and luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature. Comparative device example 1 of the present invention the results of testing the light emitting characteristics of the organic electroluminescent devices obtained in device examples 1 to 30 are shown in table 1 below.
Table 1 light emission characteristic test data of organic electroluminescent device
As can be seen from the results of table 1, the triarylamine compound of the present invention has higher luminous efficiency and longer service life when used as a hole transport layer material in an organic electroluminescent device, as compared with comparative example 1.
Comparative examples 2-3 device preparation examples: (second hole transporting layer)
Comparative example 2: firstly, placing a glass substrate on which ITO/Ag/ITO is evaporated in distilled water for cleaning for 2 times, washing for 30 minutes by ultrasonic waves, repeatedly cleaning for 2 times by using distilled water, washing by ultrasonic waves for 10 minutes, after the distilled water is cleaned, sequentially washing by using isopropanol, acetone and methanol solvents by ultrasonic waves, drying on a hot plate heated to 120 ℃, transferring to a plasma cleaning machine after drying, and transferring the substrate to a vapor deposition machine after washing for 5 minutes.
The method comprises the steps of evaporating HI-1 serving as a hole injection layer on an ITO/Ag/ITO substrate which is washed, wherein the evaporation thickness is 10nm, evaporating HT1 serving as a first hole transport layer on the hole injection layer, evaporating a contrast compound 2 serving as a second hole transport layer on the first hole transport layer, evaporating the contrast compound 2 serving as a second hole transport layer, wherein the evaporation thickness is 33nm, then evaporating a mixture of GH-1, GH-2 and GD-1 (the mass ratio is 47:47:6) on the hole transport layer in a vacuum manner to form a luminescent layer, evaporating ET-1 and Liq (the mass ratio is 1:1) serving as electron transport layers on the luminescent layer, evaporating the evaporation thickness is 35nm, evaporating LiF serving as an electron injection layer, evaporating the evaporation thickness is 1nm, evaporating Mg: ag (the mass ratio is 1:9) serving as a cathode on the electron injection layer, evaporating CP-1 serving as a cover layer on the cathode, and the thickness is 55nm, so that an organic electroluminescent device (the following functional layer materials in the preparation process of the organic electroluminescent device are prepared).
Comparative example 3: the second hole transport layer material in comparative example 2, comparative compound 2, was changed to comparative compound 3, and the other steps were the same as in comparative example 2.
Examples 31 to 75
The second hole transport layer material of the organic electroluminescent device was replaced with the compound 4, the compound 20, the compound 24, the compound 46, the compound 64, the compound 72, the compound 82, the compound 87, the compound 100, the compound 103, the compound 104, the compound 127, the compound 136, the compound 177, the compound 212, the compound 223, the compound 233, the compound 267, the compound 279, the compound 282, the compound 292, the compound 318, the compound 348, the compound 361, the compound 367, the compound 385, the compound 390, the compound 394, the compound 399, the compound 413, the compound 425, the compound 427, the compound 430, the compound 432, the compound 433, the compound 441, the compound 460, the compound 560, the compound 588, the compound 613, the compound 636, the compound 642, the compound 656, the compound 668, the compound 713 in this order, and the other steps were the same as in comparative example 2. Comparative device examples 2 to 3 of the present invention, the results of testing the light emitting characteristics of the organic electroluminescent devices obtained in device examples 31 to 75 are shown in table 2 below.
Table 2 light emission characteristic test data of organic electroluminescent device
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As can be seen from the results in Table 2, when the triarylamine compound of the present invention is used as a material for a second hole transport layer in an organic electroluminescent device, the luminous efficiency of the device can be significantly improved and the service life of the device can be prolonged, as compared with comparative examples 2 to 3.
Comparative example 4 device preparation example: (cover layer)
Comparative example 4: firstly, placing a glass substrate on which ITO/Ag/ITO is evaporated in distilled water for cleaning for 2 times, washing for 30 minutes by ultrasonic waves, repeatedly cleaning for 2 times by using distilled water, washing by ultrasonic waves for 10 minutes, after the distilled water is cleaned, sequentially washing by using isopropanol, acetone and methanol solvents by ultrasonic waves, drying on a hot plate heated to 120 ℃, transferring to a plasma cleaning machine after drying, and transferring the substrate to a vapor deposition machine after washing for 5 minutes.
The method comprises the steps of evaporating HI-1 serving as a hole injection layer on an ITO/Ag/ITO substrate which is washed, evaporating HT-2 serving as a hole transport layer on the hole injection layer, evaporating 57m in thickness, evaporating a mixture of RH-1 and RD-1 (mass ratio of 97:3) in vacuum on the hole transport layer to form a light-emitting layer, evaporating ET-1 and Liq (mass ratio of 1:1) serving as electron transport layers on the light-emitting layer, evaporating 40nm in thickness, evaporating LiF serving as the electron injection layer on the electron transport layer, evaporating 1nm in thickness, evaporating Mg: ag (mass ratio of 1:9) serving as a cathode on the electron injection layer, evaporating 10nm in thickness, evaporating a contrast compound 4 serving as a covering layer on the cathode in vacuum, and evaporating 60nm in thickness, so as to prepare the organic electroluminescent device (the material structure of each functional layer in the preparation process of the organic electroluminescent device is shown as follows).
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Examples 76 to 90
The other steps of the present invention were the same as those of comparative example 4 except that the capping layer materials of the organic electroluminescent device were replaced with the compound 64, the compound 87, the compound 127, the compound 267, the compound 279, the compound 282, the compound 292, the compound 318, the compound 367, the compound 394, the compound 399, the compound 413, the compound 588, the compound 613, the compound 656 and the compound 668 in this order. Comparative device example 4 of the present invention the results of testing the light emitting characteristics of the organic electroluminescent devices obtained in device examples 76 to 90 are shown in table 3 below.
Table 3 light emission characteristics test data of organic electroluminescent device
As can be seen from the results of table 3, the triarylamine compound of the present invention significantly improves the luminous efficiency and the service life of the device when used as a capping material in an organic electroluminescent device, as compared with comparative example 4.
It should be noted that while the present invention has been specifically described with reference to individual embodiments, it will be apparent to those skilled in the art that numerous modifications and variations can be made without departing from the principles of the present invention, and such modifications and variations fall within the scope of the present invention.
Claims (10)
1. The triarylamine compound is characterized by being represented by a structure shown in a formula I:
the Ar is as follows 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group;
the L is selected from any one of the following groups:
the x is selected from CH or N identically or differently;
the Y is 1 Selected from O, S, C (R) 2 R 3 )、N(R 4 ) One of the following;
the Y is 2 Selected from single bonds, O, S, C (R) 7 R 8 )、N(R 9 ) One of the following;
the R is 1 The halogen is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C2-C30 fused ring group of heteroaromatic ring; or two adjacent R 1 May be linked to each other to form a substituted or unsubstituted ring;
the R is 2 、R 3 、R 7 、R 8 Independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring; or said R 2 、R 3 May be linked to each other to form a substituted or unsubstituted ring;
the R is 4 、R 9 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group;
the a 1 Selected from 0, 1, 2 or 3;the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other;
the L is 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C15 alicyclic ring, and a C6-C30 arylene ring;
provided that the Ar is 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Containing one or more groups of formula II:
the R is a 、R b 、R c Independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, and fused ring group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring.
2. The triarylamine compound of claim 1 wherein L is selected from any one of the following groups:
the R is 1 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, benzocyclobutenyl, benzocyclopentenyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, acridinyl, phenanthrolinyl, a group of formula II; or two adjacent R 1 Can be connected with each other to form a substituted or unsubstituted benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring or C3-C8 aliphatic ring;
the R is 2 、R 3 、R 7 、R 8 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopentane, benzocyclohexane, fluorenyl, phenanthryl, and the like,Benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or R is 2 、R 3 Any one of them can be directly connected with L a 、L b 、L c Any one of which is bonded;
the R is 4 、R 9 Independently selected from one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or R is 4 Can be directly connected with L a 、L b 、L c Any one of which is bonded;
the a 1 Selected from 0, 1, 2 or 3; the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; the a 4 Selected from 0 or 1; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other.
3. The triarylamine compound of claim 1 wherein Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Containing one or more groups of formula II.
4. The triarylamine compound of claim 1 wherein formula II is selected from any one of the following groups:
5. the triarylamine compound of claim 1 wherein Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Independently selected from one of the following groups:
said y is identically or differently selected from N or CH;
the ring A is selected from a substituted or unsubstituted C3-C10 aliphatic ring;
the Y is 3 、Y 4 Independently selected from single bond, O, S, N (R) d )、C(R e R f ) One of the following;
the Y is 5 Selected from O, S, N (R) g )、C(R h R i ) One of the following; the Y is 6 Selected from N or CH;
the R is 5 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, benzocyclobutane, benzocyclopentane, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, benzoxazolyl, benzothiazole A group, benzimidazolyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or two adjacent R 5 May be linked to each other to form a substituted or unsubstituted ring;
the R is d 、R g And is selected from the group consisting of substituted or unsubstituted one of the following groups, identically or differently: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or said R d 、R g Can be directly connected with L 1 、L 2 、L 3 、L 4 、L 5 、L 6 Any one of which is bonded;
the R is e 、R f 、R h 、R i Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II; or R is e 、R f May be linked to each other to form a substituted or unsubstituted ring; or R is e 、R f Any one of them can be directly connected with L 1 、L 2 、L 3 、L 4 、L 5 、L 6 Any one of which is bonded;
said b 1 Selected from 0, 1, 2, 3, 4 or 5; said b 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 4 Selected from 0, 1, 2, 3 or 4; said b 5 Selected from 0, 1, 2 or 3; when two or more R's are present 5 When two or more R' s 5 Are the same as or different from each other.
6. The triarylamine compound of claim 1 wherein L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L a 、L b 、L c Independently selected from a single bond or one of the following groups:
the z is identically or differently selected from N or CH;
the ring B is selected from a substituted or unsubstituted C3-C10 aliphatic ring;
said E is selected from O, S, N (R j )、C(R k R l ) One of the following;
the R is 6 Identically or differently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, a group of formula II The method comprises the steps of carrying out a first treatment on the surface of the Or two adjacent R 6 May be linked to each other to form a substituted or unsubstituted ring;
the R is j Selected from one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; or R is j Can be directly connected with Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Any one of which is bonded;
the R is k 、R l Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, a group of formula II; or R is k 、R l May be linked to each other to form a substituted or unsubstituted ring; or R is k 、R l Any one of them may be directly bonded to Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6 Any one of which is bonded;
the c 1 Selected from 0, 1, 2, 3 or 4; the c 2 Selected from 0, 1, 2 or 3; the c 3 Selected from 0, 1 or 2; when two or more R's are present 6 When two or more R' s 6 Between which are locatedThe same as or different from each other.
7. The triarylamine compound of claim 1 wherein said triarylamine compound is selected from one of the following structures:
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8. an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or outside one or more of the anode and the cathode, wherein the organic layer contains any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 7.
9. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, wherein the organic layer comprises a hole transport region comprising any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 7.
10. An organic electroluminescent device according to claim 8, wherein the organic layer is located outside one or more of the anode and the cathode, and the organic layer comprises a coating layer containing any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 7.
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