CN114907394A - Silafluorene derivative and organic electroluminescent element containing same - Google Patents
Silafluorene derivative and organic electroluminescent element containing same Download PDFInfo
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- CN114907394A CN114907394A CN202210708471.2A CN202210708471A CN114907394A CN 114907394 A CN114907394 A CN 114907394A CN 202210708471 A CN202210708471 A CN 202210708471A CN 114907394 A CN114907394 A CN 114907394A
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- Prior art keywords
- unsubstituted
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- aryl
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- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical class C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 239000000463 material Substances 0.000 claims abstract description 45
- 239000010410 layer Substances 0.000 claims description 155
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 238000002347 injection Methods 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 28
- -1 heterocyclic aryl radicals Chemical class 0.000 claims description 26
- 230000000903 blocking effect Effects 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 150000004832 aryl thioethers Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005597 hydrazone group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011799 hole material Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 238000000151 deposition Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- 229940077398 4-methyl anisole Drugs 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- 238000005092 sublimation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
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- QQTOBDXDQYCGMA-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzoxazole Chemical compound C1=CC=C2C=C3C(N=CO4)=C4C=CC3=CC2=C1 QQTOBDXDQYCGMA-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
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Abstract
The invention relates to the technical field of organic electroluminescent materials, in particular to a silafluorene derivative shown as a formula I and an organic electroluminescent element containing the silafluorene derivative. The compound shown in the formula I improves the thermal stability and the carrier transport capacity of the material, and the material can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life when being applied to an organic electroluminescent element.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a silafluorene derivative and application thereof in an organic electroluminescent element.
Background
In general, the organic light emitting phenomenon refers to a phenomenon in which light is emitted when electric energy is applied to an organic substance. That is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, organic electroluminescent display technology has become mature, some products have entered the market, but in the process of industrialization, many problems still need to be solved. In particular, many problems have not been solved in the carrier injection and transport properties, the electroluminescent properties of the materials, the service life, the color purity, the matching between various materials and between various electrodes, and the like of various organic materials used for manufacturing elements. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and lifetime, which greatly limits the development of OLED technology. The metal complex phosphorescent material utilizing triplet state luminescence has high luminescence efficiency, and green and red materials of the metal complex phosphorescent material meet the use requirements, but the metal complex phosphorescent material requires a phosphorescent material or a hole material with a high triplet state energy level to be matched with the metal complex phosphorescent material, so that the development of the phosphorescent material or the hole material with the high triplet state energy level is an urgent need of the current development of the OLED.
Under the current technological development, improvements are also needed, both for fluorescent materials and for phosphorescent materials, in particular in terms of operating voltage, efficiency and lifetime for use in organic electroluminescent elements and thermal stability during sublimation.
Accordingly, in order to overcome the above-described problems of the conventional techniques and further improve the characteristics of the organic electroluminescent element, development of a more stable and effective substance which can be used as a phosphorescent material or a hole-forming material in the organic electroluminescent element is continuously required.
Disclosure of Invention
The invention aims to provide a silafluorene derivative.
Another object of the present invention is to provide an organic electroluminescent material containing the above silafluorene derivative.
It is a further object of the present invention to provide an organic electroluminescent device and the use of the above silafluorene derivatives in the preparation of organic electroluminescent devices.
In order to achieve the purpose, the invention adopts the following technical scheme:
a silafluorene derivative has a structural formula shown in formula I:
wherein:
R a 、R b each independently selected from hydrogen, C 1 ～C 40 Alkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
each W is independently selected from N or CR 5 Or any two adjacent w are groups shown in formula (II) or formula (III),
a represents, identically or differently on each occurrence, CR 6 Or N, and "^" indicates any adjacent two groups W in formula (I);
g is selected from O, S, NAr 3 Or CR 7 R 8 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl or a group of formula (IV) and at R 1 、R 2 、R 3 、R 4 、R 5 At least two of the groups are groups shown in a formula (IV);
Ar 1 、Ar 2 、A r 3 are each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Group consisting of heterocyclic aryl radicals, Ar 1 And Ar 2 Optionally joined or fused to form a substituted or unsubstituted ring with or without N, O, S, Si, B or CR in the ring 7 R 8 ；
L 1 Selected from the group consisting of single bonds, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heterocyclylene aryl;
R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 each independently selected from the group consisting of: hydrogen, deuterium, fluorine, nitrile group, having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), substituted or unsubstituted C 6 -C 60 Aryl or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl radicals, and optionally two adjacentOr a plurality of substituents may be optionally joined or fused to form a substituted or unsubstituted ring with or without N, O, s, si, P or B;
n is an integer of 0 to 5;
represents L 1 And a bond of formula (I).
In the present invention, the "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in which adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
Preferably, the silafluorene derivative is selected from one or more of the structures shown below:
wherein R is 1 、R 2 、R 3 、R 4 、R 5 At each occurrence is hydrogen or a group of formula (Iv), and at R 1 、R 2 、R 3 、R 4 、R 5 At least two of them are groups of formula (IV), preferably R 1 、R 2 、R 3 、R 4 At each occurrence is a group of formula (IV).
Preferably, G is O, S or CR 7 R 8 。
Preferably, said n is selected from 0, 1 or 2.
Preferably, said R is a 、R b Selected from the group consisting of methyl, ethyl or phenyl.
Preferably, R 5 、R 6 Is hydrogen or deuterium.
Preferably, R 7 、R 8 Each independently selected from the group consisting of hydrogen, methyl, phenyl, fluorenyl.
Preferably, in the above compound, L is 1 Selected from a single bond or from the following III-1 to III-15Group consisting of the groups shown:
wherein the content of the first and second substances,
Z 11 and Z 12 Each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C 1 -C 60 Alkyl radical, C 2 -C 60 Alkenyl radical, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy radical, C 3 -C 60 Cycloalkyl radical, C 3 -C 60 Cycloalkenyl radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 One or more of a heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 2 represents O, s, CR ' R ' or NAr ';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 ～C 60 Alkyl of (C) 1 ～C 60 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine group,Or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 60 Alkyl of (C) 1 ～C 60 Heteroalkyl of (a), C 3 ～C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl or naphthyl;
Aryl in the sense of the present invention contains 6 to 60 carbon atoms and heteroaryl contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5, said heteroatom preferably being selected from N, O or s. The aryl and heteroaryl radicals are in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, sugarcane, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, idobenzene, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridecyl, spirotriindene, spiroisotridecyl, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5, 6] quinoline, benzo [6, 7] quinoline, benzo [7, 8] quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, Quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazahnthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4, 5, 9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1, 2, 3-triazole, 1, 2, 4-triazole, benzotriazole, 1, 2, 3-oxadiazole, 1, 2, 4-oxadiazole, 1, 2, 5-oxadiazole, 1, 3, 4-oxadiazole, 1, 2, 3-thiadiazole, 1, 2, 4-thiadiazole, 1, 2, 5-thiadiazole, 1, 3, 4-thiadiazole, 1, 3, 5-triazine, 1, 2, 4-triazine, 1, 2, 3-triazine, tetrazole, 1, 2, 4, 5-tetrazine, 1, 2, 3, 4-tetrazine, 1, 2, 3, 5-tetrazine, purine, pteridine, indolizine, quinazoline, and benzothiadiazole, or a group derived from a combination of these systems.
The term "substituted or unsubstituted" as used herein means a group selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic acid group or a sulfonate thereof, a phosphoric acid group or a phosphate thereof, and C 1 -C 60 Alkyl radical, C 2 -C 60 Alkenyl radical, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy radical, C 3 -C 60 Cycloalkyl radical, C 3 -C 60 Cycloalkenyl radical, C 6 -C 60 Aryl radical, C 6 -C 60 Aryloxy radical, C 6 -C 60 An arylthioether group and C 2 -C 60 The heterocyclic aryl group may be substituted or unsubstituted with 1 or more substituents, or may be substituted or unsubstituted with substituents formed by connecting 2 or more substituents among the above-exemplified substituents.
Preferably, the silafluorene derivative is selected from the group consisting of C01 to C180:
wherein, T 3 -:
-G-is selected from-O-, S-or one of the following structures:
and-represent a connecting bond.
In one aspect, the present invention provides a method for preparing a silafluorene derivative of formula (I), as shown in scheme 1 below:
scheme 1:
in scheme 1, the symbols used are as defined in formula (I), and X is Cl, Br, I or OTf;
specifically, the compound of formula (I) is prepared from a compound C with a silafluorene mother nucleus structure and a compound D or D' containing an arylamine substituent through palladium catalysis or base catalysis coupling reaction.
As palladium catalysts which can be used for the palladium-catalyzed coupling reaction, there may be selected: pd (P-tBu) 3 ) 2 、Pd(PPh 3 ) 4 、Pd 2 (dba) 3 、Pd 2 (dba) 3 CHCl 3 、PdCl 2 (PPh 3 ) 2 、PdCl 2 (CH 3 CN) 2 、Pd(OAc) 2 、Pd(acac) 2 、Pd/C、PdCl 2 、[Pd(allyl)Cl] 2 And the like, or a mixture of two or more thereof is used.
In addition, the base used in the palladium-catalyzed coupling reaction or base-catalyzed coupling reaction may be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amylate, sodium ethoxide, sodium methoxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, and the like, and mixtures of one or two or more thereof.
The coupling reaction may be carried out in an organic solvent, wherein the organic solvent may be selected from: ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1, 4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ether, diethylene glycol diethyl ether, or anisole, aromatic hydrocarbon solvents such as benzene, toluene, or xylene, chlorobenzene, dichlorobenzene, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and sulfolane, and one or a mixture of two or more thereof may be used.
In addition, the compounds of formula D and D' may be prepared using conventional organic reactions, or may be obtained commercially.
The invention also provides a material, wherein the raw material of the material comprises the silafluorene derivative organic electroluminescent material, and preferably, the material is a hole injection Layer material, a hole transport Layer material, a hole barrier Layer material, a luminescent Layer material, an electron transport Layer material, an electron injection Layer material, a Capping Layer (CPL) material or an electron barrier Layer material. The material containing the compound of the present invention has carrier transporting ability or light extracting ability.
The present invention also provides an organic electroluminescent element comprising a first electrode, a second electrode, a CPL, and one or more organic layers interposed between the first electrode and the second electrode; the material of at least one of the organic layer or CPL comprises the compounds described above.
The organic electroluminescent element includes a cathode, an anode, a CPL, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent element described herein may include one light-emitting layer, or it may include a plurality of light-emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises, according to the invention, a compound according to the invention.
Further, the organic electroluminescent element according to the invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light-emitting layer is directly adjacent to the hole injection layer or the anode and/or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and in the light-emitting layer and in CPL, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10% -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers can also be applied by means of organic vapor deposition methods or by means of carrier gas sublimation, where 10 is -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula I. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
The invention therefore also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to pharmaceutical compositions comprising at least one compound of the invention as indicated above. The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. Processing of the compounds of the invention from the liquid phase, for example by spin coating or by printing processes, requires the processing of formulations of the compounds of the invention which may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchytone, 1, 2, 3, 5-tetramethylbenzene, 1, 2, 4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, 4-methylanisole, toluene, xylene, acetone, xylene, or mixtures of the like, or mixtures of the, Cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or a mixture of these solvents.
Preferably, in the above organic electroluminescent element, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, CPL, an electron transport layer, an electron injection layer, or an electron blocking layer.
The invention also provides application of the compound in preparing an organic electroluminescent element.
In addition, unless otherwise specified, all starting materials for use in the present invention are commercially available, and any range recited herein includes any value between the endpoints and any subrange between the endpoints and any value between the endpoints or any subrange between the endpoints.
The present invention also relates to mixtures comprising at least one compound of the formula (I) or the preferred embodiments described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the further compounds can be fluorescent or phosphorescent emitters. The mixture may then additionally comprise other materials as additional matrix materials. The invention also relates to the use of the compounds according to the invention in electronic components. Preferably, the compounds according to the invention are used in a hole transport layer or as a matrix material in a light-emitting layer, as mentioned above and below. The compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components, differ from the prior art by one or more of the following surprising advantages:
1. the electronic components obtainable using the compounds of the present invention exhibit very high stability and very long lifetime compared to those obtainable using conventional compounds.
2. The electronic components obtainable using the compounds of the invention exhibit high efficiencies, in particular high luminous efficiencies and high external quantum efficiencies.
3. The compounds of the present invention provide low operating voltages.
4. The compounds according to the invention can be processed using conventional methods, whereby cost advantages can also be achieved.
5. The films obtainable using the compounds of the invention exhibit excellent quality, especially with regard to the uniformity of the film.
6. The compounds of the invention can be produced in a very rapid and easy manner using conventional methods, so that cost advantages can also be achieved.
These advantages mentioned above are not accompanied by a weakening of other electronic properties.
It should be noted that variations of the embodiments described in the present invention fall within the scope of the invention. Each feature disclosed in this specification may be replaced by alternative features serving the same, equivalent or similar purpose, unless expressly excluded. Thus, unless expressly stated otherwise, each feature disclosed in this specification is intended to be an example of a generic series of equivalent or similar features.
All features of the invention may be combined with each other in any manner, unless specified features and/or steps are mutually exclusive. This applies in particular to the preferred features of the invention. Also, features that are not necessarily combined may be used separately (and not in combination). It should furthermore be pointed out that many features, in particular features of preferred embodiments of the invention, are inventive per se and should not be considered as only part of an embodiment of the invention. Independent protection may be sought for these features in addition to or in lieu of each and every invention that is presently claimed.
The teachings of the technical actions disclosed in the present invention can be extracted and combined with other embodiments. The present invention is explained in more detail by the following examples, but is not intended to be limited thereby. Based on the description, one skilled in the art will be able to carry out the invention within the full scope of the disclosure and, without inventive effort, be able to prepare and use other compounds of the invention in electronic components or use the methods of the invention.
Drawings
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic diagram of an organic light-emitting device 200 with two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light emitting layer, while device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the scope of the present invention is not limited thereto.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience in describing the present invention and simplifying the description, but do not indicate or imply that the referred devices or elements must have a specific orientation, be constructed and operated in a specific orientation, and thus, should not be construed as limiting the present invention.
The experimental procedures used in the following examples are conventional unless otherwise specified. The experimental raw materials and the relevant equipment used in the following examples are commercially available unless otherwise specified, and the percentages are by mass unless otherwise specified.
The following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Example 1
A process for the preparation of compound C-1 comprising the steps of:
preparation of Compound Int-1:
under the protection of nitrogen, 0.26mol of 2 '-bromo-2, 4-dichloro-1, 1' -biphenyl is dissolved in 600mL of dry THF, the temperature is reduced to-78 ℃, 0.39mol of 2.5M n-butyllithium n-hexane solution is dropwise added, the mixture is stirred and reacted for 20 minutes, 0.40mol of dimethylchlorosilane is dropwise added, the mixture is heated to room temperature and stirred and reacted for 24 hours, 200mL of saturated ammonium chloride aqueous solution is dropwise added, an organic phase is separated, an aqueous phase is extracted by ethyl acetate, the organic phase is collected, dried and filtered, the filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column to obtain a compound Int-1, namely a white solid, and the yield is as follows: 89 percent.
Preparation of Compound C-1:
under nitrogen protection, 18.0mmol of triphenylphosphine and 3.0mmol of [ RhCl (cod) ]] 2 Mixing a catalyst and 450mL of 1, 4-dioxane, stirring at room temperature for reaction for 30 minutes, adding 0.2mol of Int-1, heating to 80 ℃, stirring for reaction for 12 hours, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain white solid C-1, wherein the yield is as follows: 66%, GC-MS (EI): 278.01, 280.01.
Referring to the analogous synthetic procedure described above, the products shown in Table 1 were prepared.
TABLE 1 correspondence table of reactants and synthesis products and yields
Example 2
Preparation of compound C01:
10.0mmol of C-1 was dissolved in 60mL of xylene, and 21.0mmol of phenylbiphenylamine, 25.0mmol of sodium tert-butoxide, 0.2mmol of cuprous iodide and 0.1mmol of Pd were added under nitrogen protection 2 (dba) 3 Adding 0.2mmol of Xantphos into the catalyst, heating to 110 ℃, stirring for reacting for 16 hours, cooling to room temperature, adding 20mL of water for dilution, extracting with toluene, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound C01, wherein the yield is as follows: 78%, after sublimation in vacuo, HPLC: 99.97%, MS (MALDI-TOF): 697.3053[ M + H ] M/z] + ； 1 HNMR(δ、CDCl 3 )：7.85～7.83(1H，m)；7.74～7.68(4H，m)；7.62～7.59(2H，m)；7.54～7.50(4H，m)；7.48～7.43(5H，m)；7.40～7.35(6H，m)；7.25～7.19(4H，m)；7.15(1H，s)；7.11(1H，s)；7.08～7.02(4H，s)；6.99～6.94(2H，m)；0.21(6H，s)。
Referring to the analogous synthetic procedure described above, the products shown in Table 2 were prepared.
TABLE 2 correspondence table of reactants and synthesized products and yields
Example 3
Preparation of compound C163:
under the protection of nitrogen, 10.0mmol of C-11 is dissolved in 40mL of toluene, 22.0mmol of 9-phenylcarbazole-3-boric acid, 50.0mmol of anhydrous potassium carbonate, 0.2mmol of cuprous iodide and 0.01mmol of Pd132 catalyst are added, 20mL of ethanol and 20mL of water are added, the mixture is heated, refluxed and stirred for reaction for 16 hours, the mixture is cooled to room temperature, 50mL of water is added for dilution, extraction is carried out by ethyl acetate, an organic phase is collected, drying and filtration are carried out, filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column, so that the compound C163 is obtained, and the yield: 82%, after sublimation in vacuo, HPLC: 99.95%, MS (MALDI-TOF): 770.3433[ M + H ] M/z] + ； 1 HNMR(6、CDCl 3 )：8.39(1H，s)；8.25～8.21(2H，m)；8.12(1H，s)；8.03～7.95(3H，m)；7.74～7.72(1H，d)；7.69～7.61(8H，m)；7.54～7.46(9H，m)；7.37～7.27(8H，m)；7.23～7.16(6H，m)；7.12～7.08(1H，m)。
Referring to a similar synthetic procedure as described above, the products shown in table 3 were prepared.
TABLE 3 correspondence table of reactants and synthesis products and yields
Example 4
An organic electroluminescent element 200, the structure of which is shown in fig. 2, comprises a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, a light emitting layer 106 disposed on the electron blocking layer 105, an electron transport layer 107 disposed on the light emitting layer 106, an electron injection layer 108 disposed on the electron transport layer 107, a cathode layer 109 disposed on the electron injection layer 108, and a CPL layer 110 disposed on the cathode layer, and is prepared by the following steps:
1) the glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, depositing silver on the ITO film as anode layer to obtain a deposited film with a thickness of
The compound of the present invention is deposited as a hole injection layer to a thickness of
3) Continuously depositing a compound HTM on the hole injection layer to form a hole transport layer, wherein the deposition film has a thickness of
4) Continuously depositing a compound EBL on the hole transport layer to form an electron blocking layer with a thickness of
5) Continuously depositing PHT as main material and GD110 as doping material on the electron blocking layer, wherein GD110 is 3% of PHT mass, and the organic light emitting layer has a deposition film thickness of
6) And continuously evaporating a layer of LiQ and ET06 on the organic light-emitting layer to form an electron transport layer, wherein the mass ratio of LiQ to ET06 is 50: 50, the thickness of the deposition film is
7) Continuously evaporating a layer of LiF on the electron transport layer to form an electron injection layer, wherein the thickness of the evaporated film is
8) Evaporating metal magnesium and silver on the electron injection layer to form a transparent cathode layer, wherein the mass ratio of magnesium to silver is 1: 2, and the thickness of the evaporated film is
9) Depositing a CPL layer as element on the transparent cathode layer by evaporation to a thickness of
The OLED element provided by the invention is obtained.
The structures of the compounds HTM, EBL, PHT, GD110, ET06 and LiQ used in example 4 are as follows:
example 5
An organic electroluminescent element 100 is shown in fig. 1, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, a light emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the light emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, a cathode layer 110 disposed on the electron injection layer 109, and a CPL layer 111 disposed on the cathode layer 110.
Comparative example 1
Following the same procedure as in example 4, the compound of the present invention in step 2) and tertiary step 9) was replaced with H-1 to give comparative element 1;
comparative example 2
Following the same procedure as in example 4, the compound of the present invention in step 2) and tertiary step 9) was replaced with H-2 to give comparative element 2;
the organic electroluminescent element prepared by the above process was subjected to the following performance tests:
the driving voltage and current efficiency of the organic electroluminescent element prepared in example 4 and comparative examples 1 and 2 and the lifetime of the element were measured using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and the current density of the organic electroluminescent element was measured to reach 10mA/cm 2 The voltage is the driving voltage, and the brightness at the moment is measured; the ratio of the brightness to the current density is the current efficiency; the LT 95% lifetime test is as follows: using a luminance meter at 1000cd/m 2 The luminance degradation of the organic electroluminescent element was measured to 950cd/m while maintaining a constant current at luminance 2 The performance test data of the obtained element were normalized with reference to comparative element 1, the results of which are shown in table 4:
TABLE 4 test results of the performance of each element
Ph is phenyl, PhPhPh is biphenyl, Nap is naphthyl, and Me is methyl.
As can be seen from Table 4, the light-emitting device prepared from the silafluorene derivative of the present invention as the hole material and CPL material was also at 10mA/cm 2 Under the condition, the driving voltage is reduced compared with H-1 and H-2, the luminous efficiency is improved, excellent luminous performance is shown, and the LT 95% service life has obvious advantages. It is demonstrated that the disclosed compound achieves more excellent carrier balance capability than the comparative element due to the replacement of the carbon atom at the 9-position of fluorene with a silicon atom. The performance of the compound used as the hole material can prove that the compound is an excellent hole material.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A silafluorene derivative is characterized in that the structural formula of the silafluorene derivative is shown as a formula I:
wherein:
R a 、R b each independently selected from hydrogen, C 1 ～C 40 Alkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
each W is independently selected from N or CR 5 Or any two adjacent W are groups shown in formula (II) or formula (III),
a represents, identically or differently on each occurrence, CR 6 Or N, and "^" indicates any adjacent two groups W in formula (I);
g is selected from O, S, NAr 3 Or CR 7 R 8 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl or a group of formula (IV) and at R 1 、R 2 、R 3 、R 4 、R 5 At least two of which are groups of formula (IV),
Ar 1 、Ar 2 、Ar 3 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Group consisting of heterocyclic aryl radicals, Ar 1 And Ar 2 Optionally joined or fused to form a substituted or unsubstituted ring with or without N, O, S, Si, B or CR in the ring 7 R 8 ；
L 1 Selected from the group consisting of single bonds, substituted or unsubstituted C 6 -C 60 Arylene, substituted or notSubstituted C 2 -C 60 Heterocyclylene aryl;
n is an integer of 0 to 5;
represents L 1 And a bond of formula (I).
2. Silafluorene derivative according to claim 1, wherein the silafluorene derivative is selected from one or more of the following structures:
wherein R is 1 、R 2 、R 3 、R 4 、R 5 At each occurrence is hydrogen or a group of formula (IV) and at R 1 、R 2 、R 3 、R 4 、R 5 At least two of the groups are groups shown in a formula (IV);
g is O, S or CR 7 CR 8 ；
n is selected from 0, 1 or 2.
3. Silafluorene derivative according to claim 1 or 2, wherein R is a 、R b Selected from the group consisting of methyl, ethyl or phenyl;
R 5 、R 6 is hydrogen or deuterium;
R 7 、R 8 each independently selected from the group consisting of hydrogen, methyl, phenyl, fluorenyl.
4. A fluorene derivative according to any one of claims 1 to 3, wherein L is 1 Selected from a single bond or a group consisting of the following groups III-1 to III-15:
wherein the content of the first and second substances,
Z 11 and Z 12 Each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C 1 -C 60 Alkyl radical, C 2 -C 60 Alkenyl radical, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy radical, C 3 -C 60 Cycloalkyl radical, C 3 -C 60 Cycloalkenyl radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 One or more of a heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 2 represents O, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 ～C 60 Alkyl of (C) 1 ～C 60 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 60 Alkyl of (C) 1 ～C 60 Heteroalkyl of (a), C 3 ～C 60 Cycloalkyl ofSubstituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl or naphthyl;
5. The silafluorene derivative of any of claims 1-4, wherein the structural formula of the silafluorene derivative is selected from the group consisting of C01-C180:
wherein, T 3 -:
-G-is selected from-O-, S-or one of the following structures:
and-represent a connecting bond.
6. An organic electroluminescent material, characterized in that a raw material of the organic electroluminescent material comprises the silafluorene derivative according to any one of claims 1 to 5.
7. An organic electroluminescent element comprising a first electrode, a second electrode, CPL, and one or more organic layers interposed between the first electrode and the second electrode; the material of at least one of the organic layers or CPL comprises a silafluorene derivative according to any one of claims 1-5.
8. The organic electroluminescent element according to claim 7, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, CPL, or an electron blocking layer.
9. Use of a compound according to any one of claims 1 to 5 in an organic electroluminescent element, wherein the compound is used in a hole transport layer, a hole blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, CPL or an electron blocking layer of the organic electroluminescent element.
10. A consumer product comprising an organic electroluminescent element, the organic electroluminescent element comprising: a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises a compound comprising the silafluorene derivative of any one of claims 1 to 5.
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