CN108137444A - 三联苯并环戊二烯类化合物、高聚物、混合物、组合物以及有机电子器件 - Google Patents
三联苯并环戊二烯类化合物、高聚物、混合物、组合物以及有机电子器件 Download PDFInfo
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- CN108137444A CN108137444A CN201680059905.3A CN201680059905A CN108137444A CN 108137444 A CN108137444 A CN 108137444A CN 201680059905 A CN201680059905 A CN 201680059905A CN 108137444 A CN108137444 A CN 108137444A
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- CN
- China
- Prior art keywords
- pentalene
- terphenyl
- group
- class compound
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 Terphenyl pentalene class compound Chemical class 0.000 title claims abstract description 106
- 229920000642 polymer Polymers 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 239000000463 material Substances 0.000 claims abstract description 94
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- BFRDBSBKJUVSNP-UHFFFAOYSA-N 9h-fluorene;silicon Chemical compound [Si].C1=CC=C2CC3=CC=CC=C3C2=C1 BFRDBSBKJUVSNP-UHFFFAOYSA-N 0.000 claims description 10
- 230000005540 biological transmission Effects 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000004575 stone Substances 0.000 claims description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002220 fluorenes Chemical class 0.000 claims description 9
- 150000002240 furans Chemical class 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 230000005669 field effect Effects 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 230000004888 barrier function Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 230000003252 repetitive effect Effects 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000013086 organic photovoltaic Methods 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 238000007639 printing Methods 0.000 abstract description 25
- 238000000034 method Methods 0.000 abstract description 15
- CDTRJYSYYSRJIL-UHFFFAOYSA-N indene Chemical group C1=CC=C2C=C=CC2=C1 CDTRJYSYYSRJIL-UHFFFAOYSA-N 0.000 abstract description 5
- 238000005424 photoluminescence Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 33
- 239000002096 quantum dot Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000004065 semiconductor Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000004982 aromatic amines Chemical class 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical group [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 4
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 239000013110 organic ligand Substances 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000005504 styryl group Chemical group 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- YBNMDCCMCLUHBL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-pyren-1-ylbutanoate Chemical group C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1CCCC(=O)ON1C(=O)CCC1=O YBNMDCCMCLUHBL-UHFFFAOYSA-N 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910004613 CdTe Inorganic materials 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Natural products CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000004054 semiconductor nanocrystal Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 2
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical group CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
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- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- JRRDISHSXWGFRF-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOC JRRDISHSXWGFRF-UHFFFAOYSA-N 0.000 description 2
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- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 2
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- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 2
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- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-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
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 2
- LIWRTHVZRZXVFX-UHFFFAOYSA-N 1-phenyl-3-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC(C=2C=CC=CC=2)=C1 LIWRTHVZRZXVFX-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- GFWVDQCGGDBTBS-UHFFFAOYSA-N 2,6,8-trimethylnonan-4-one Chemical compound CC(C)CC(C)CC(=O)CC(C)C GFWVDQCGGDBTBS-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- HJKGBRPNSJADMB-UHFFFAOYSA-N 3-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1 HJKGBRPNSJADMB-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 2
- YNMZZHPSYMOGCI-UHFFFAOYSA-N Aethyl-octyl-keton Natural products CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 description 2
- 229910017115 AlSb Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000009854 Cucurbita moschata Nutrition 0.000 description 2
- 240000001980 Cucurbita pepo Species 0.000 description 2
- 235000009852 Cucurbita pepo Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 2
- 229910005540 GaP Inorganic materials 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明公开了一种溶解性和成膜性较好的三联苯并环戊二烯类化合物,包含其的高聚物、混合物、组合物以及有机电子器件。这种三联苯并环戊二烯类化合物中含有苯并环戊二烯结构,能级的匹配、结构的对称性,为提高三联苯并环戊二烯类化合物及光电器件的化学/环境稳定性提供了可能。这种三联苯并环戊二烯类化合物在有机溶剂里的溶解性较好,同时分子量较高,便于通过印刷的方法形成高质量的薄膜。这种三联苯并环戊二烯类化合物用于OLED中,特别是作为发光层材料,能提供较高的量子效率、发光稳定性和器件寿命。
Description
本发明涉及有机光电材料领域,尤其涉及一种三联苯并环戊二烯类化合物,包含其的高聚物、混合物、组合物以及有机电子器件。
有机半导体材料具有结构多样性、制造成本相对较低、光电性能优越等特性,在发光二极管(OLED)等光电器件(例如平板显示器和照明)方面的应用具有巨大的潜力。
为了提高有机发光二极管的发光性能,推进有机发光二极管大范围产业化进程,各类新型结构的有机光电性能材料体系已被广泛地开发。其中,苯并环戊二烯类结构化合物,如芴,螺芴,吲哚芴类等等,由于具有优异的光电响应和载流子传输性能,在光电器件中得到了广泛的应用。但目前报道的苯并环戊二烯类结构化合物在稳定性方面仍存在着一定的局限性,为了进一步挖掘这类材料的光电性能,新型结构的苯并环戊二烯类结构仍有待开发。
另外,为了降低生产成本,实现大面积的OLED器件,印刷OLED正在成为一个最有希望的技术选项。对此,印刷OLED材料是关键。然而目前开发的基于蒸镀技术的小分子OLED材料,由于其较低的分子量和刚性的芳香性分子结构使得溶解性和成膜性都比较差,特别是难以形成形貌规整的无空洞的非晶薄膜。因此,目前,对印刷OLED尚缺乏相应的材料解决方案,高性能的小分子有机发光二极管仍是通过真空蒸镀的方法制备。因此,设计合成具有好的溶解性和成膜性的有机小分子功能化合物对实现高性能溶液加工有机发光二极管显得尤为重要。
发明内容
基于此,有必要提供一种溶解性和成膜性较好的三联苯并环戊二烯类化合物,包含其的高聚物、混合物、组合物以及有机电子器件。
一种三联苯并环戊二烯类化合物,具有如下通式(1):
其中,L为连接单元,L选自碳原子数为6~40的芳香基团或碳原子数为3~40的杂芳基团;
A1、A2或A3选自碳原子数为6~30的芳香基团或碳原子数为3~30的杂芳基团;
R1、R2或R3选自H、D、F、CN、碳原子数为1~30的烷基、碳原子数为3~30的环烷基、碳原子数为6~60芳香族烃基、碳原子数为3~60的芳香族杂环基,并且R1、R2或R3上的一个或多个位置可以被H、D、F、CN、烷基、芳烷基、烯基、炔基、腈基、胺基、硝基、酰基、烷氧基、羰基、砜基、环烷基或羟基取代。
一种高聚物,所述高聚物至少包含一个如上述的三联苯并环戊二烯类化合物所包括的通式(1)所示的重复单元。
一种混合物,包括上述的三联苯并环戊二烯类化合物或上述的高聚物;
所述混合物还包括有机功能材料。
一种组合物,包括上述的三联苯并环戊二烯类化合物、上述的高聚物或如上述的混合物;
所述组合物还包括有机溶剂。
一种有机电子器件,包括上述的三联苯并环戊二烯类化合物或上述的高聚物。
这种三联苯并环戊二烯类化合物中含有苯并环戊二烯结构,能级的匹配、结构的对称性,为提高三联苯并环戊二烯类化合物及光电器件的化学/环境稳定性提供了可能。这种三联苯并环戊二烯类化合物在有机溶剂里的溶解性较好,同时分子量较高,便于通过印刷的方法形成高质量的薄膜。这种三联苯并环戊二烯类化合物用于OLED中,特别是作为发光层材料,能提供较高的量子效率、发光稳定性和器件寿命。
为使本发明的上述目的、特征和优点能够更加明显易懂,下面结合附图和具体实施例对本发明的具体实施方式做详细的说明。在下面的描述中阐述了很多具体细节以便于充分理解本发明。但是本发明能够以很多不同于在此描述的其它方式来实施,本领域技术人员可以在不违背本发明内涵的情况下做类似改进,因此本发明不受下面公开的具体实施的限制。
在本发明中,组合物和印刷油墨,或油墨具有相同的含义,它们之间可以互换。
在本发明中,主体材料,基质材料,Host或Matrix材料具有相同的含义,它们之间可以互换。
在本发明中,金属有机络合物,金属有机配合物,有机金属配合物具有相同的含义,可以互换。
在本发明中,聚合物,高聚物,高分子材料具有相同的含义,可以互换。
本发明公开了一种三联苯并环戊二烯类化合物,具有如下通式(1):
其中,L为连接单元,L选自碳原子数为6~40的芳香基团或碳原子数为3~40的杂芳基团;
A1、A2或A3选自碳原子数为6~30的芳香基团或碳原子数为3~30的杂芳基团;
R1、R2或R3选自H、D、F、CN、碳原子数为1~30的烷基、碳原子数为3~30的环烷基、碳原子数为6~60芳香族烃基、碳原子数为3~60的芳香族杂环基,并且R1、R2或R3上的一个或多个位置可以被H、D、F、CN、烷基、芳烷基、烯基、炔基、腈基、胺基、硝基、酰基、烷氧基、羰基、砜基、环烷基或羟基取代。
优选的,L为碳原子数为6~30的芳香基团或碳原子数为3~30的芳杂基团。
更优选的,L为碳原子数为6~25的芳香基团或碳原子数为3~25的芳杂基团。
特别优选的,L为碳原子数为6~20的芳香基团或碳原子数为3~20的芳杂基团。
芳族基团指至少包含一个芳环的烃基,包括单环基团和多环的环系统。杂芳族基团指包含至少一个杂芳环的烃基(含有杂原子),包括单环基团和多环的环系统。这些多环的环可以具有两个或多个环,其中两个碳原子被两个相邻的环共用,即稠环。多环的这些环中,至少一个是杂芳族的。
本发明中,芳香族或杂芳香族环系不仅包括芳香基或杂芳香基的体系,而且,其中多个芳基或杂芳基也可以被短的非芳族单元间断(<10%的非H原子,优选小于5%的非H原子,比如C、N或O原子)。因此,比如9,9'-螺二芴,9,9-二芳基芴,三芳胺,二芳基醚等体系,也同样认为是芳香族环系。
具体地,芳族基团包括:苯、萘、蒽、菲、二萘嵌苯、并四苯、芘、苯并芘、三亚苯、苊、芴及其衍生物。
具体地,杂芳族基团包括:呋喃、苯并呋喃、噻吩、苯并噻吩、吡咯、吡唑、三唑、咪唑、噁唑、噁二唑、噻唑、四唑、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、吡啶、吡嗪、哒嗪、嘧啶、三嗪、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、及其衍生物。
优选的,L选自苯、萘、蒽、菲、芘、吡啶、嘧啶、三嗪、芴、硫芴、硅芴、咔唑、噻吩、呋喃、噻唑、三苯胺、三苯基氧磷、四苯基硅、螺芴、螺硅芴等基团。
更优选的,L选自苯、吡啶、嘧啶、三嗪、咔唑等基团。
优选的,R1、R2或R3选自甲基、苯、萘、蒽、菲、芘、吡啶、嘧啶、三嗪、芴、硫芴、硅芴、咔唑、噻吩、呋喃、噻唑、三苯胺、三苯基氧磷,四苯基硅、螺芴、螺硅芴等基团。
更优选的,R1、R2或R3选自苯、吡啶、嘧啶、三嗪、咔唑等基团。
特别优选的,L选自如下结构单元或如下结构单元进一步被取代形成的取代单元:
优选的,A1、A2或A3选自碳原子数为6~25的芳香基团或碳原子数为3~25的芳杂基团。
更优选的,A1、A2或A3选自碳原子数为6~22的芳香基团或碳原子数为3~22的芳杂基团。
特别优选的,A1、A2或A3选自如下结构基团中的一种:
其中,X选自CR1或N;
Y选自CR2R3、SiR2R3、NR2、C(=O)、S或O;
R1、R2或R3选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链的烷基、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基或硫代烷氧基基团、具有3至20个C原子的是甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团(-CN)、氨基甲酰基基团(-C(=O)NH2)、卤甲酰基基团(-C(=O)-A其中A代表卤素原子)、甲酰基基团(-C(=O)-H)、异氰基基团、异氰酸酯基团、硫氰酸酯基团、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、Br、F、可交联的基团、具有5至40个环原子的芳族环系、具有5至40个环原子的杂芳族环系、具有5至40个环原子的取代的芳族环系、具有5至40个环原子的取代的杂芳族环系、具有5至40个环原子的芳氧基基团和具有5至40个环原子的杂芳氧基基团中的一种或一种以上的组合,其中一个或多个基团R1、R2和R3可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
在一个具体的实施例中,A1、A2或A3选自如下结构基团或如下结构基团进一步被取代形成的取代基团中的一种:
其中,X选自N(R)、B(R)、C(R)2、Si(R)2、O、S、C=N(R)、C=C(R)2、P(R)、P(=O)R、S=O、SO2或无,X优选为N(R)、C(R)2、O或S;
R选自碳原子数为1~30的烷基、碳原子数为3~30的环烷基、碳原子数为6~60芳香族烃基或碳原子数为3~60的芳香族杂环基,并且R上的一个或多个位置可以被H、D、F、CN、烷基、芳烷基、烯基、炔基、腈基、胺基、硝基、酰基、烷氧基、羰基、砜基、环烷基或羟基取代。
在一些特别优选的实施例中,A1、A2或A3选自如下结构基团或如下结构基团进一步被取代形成的取代基团中的一种:
优选的,R1、R2、R3或R选自甲基、苯、萘、蒽、菲、芘、吡啶、嘧啶、三嗪、芴、硫芴、硅芴、咔唑、噻吩、呋喃、噻唑、三苯胺、三苯基氧磷,四苯基硅、螺芴、螺硅芴等基团。
更优选的,R1、R2、R3或R选自苯、吡啶、嘧啶、三嗪、咔唑等基团。
优选的,本发明公开的三联苯并环戊二烯类化合物选自如下结构式的化合物中的一个:
其中L、R1、R2和R3的含义如上所述。
更优选的,本发明公开的三联苯并环戊二烯类化合物选自如下结构式的化合物中的一个:
其中A1、A2、A3、R1、R2和R3的含义如上所述。
本发明公开的三联苯并环戊二烯类化合物可以作为功能材料用于电子器件中。有机功能材料包括空穴注入材料(HIM)、空穴传输材料(HTM)、电子传输材料(ETM)、电子注入材料(EIM)、电子阻挡材料(EBM)、空穴阻挡材料(HBM)、发光体(Emitter)、主体材料(Host)和有机染料。
优选的,本发明公开的三联苯并环戊二烯类化合物可以作为主体材料、电子传输材料或空穴传输材料。
更优选的,本发明公开的三联苯并环戊二烯类化合物可以作为磷光主体材料。
作为磷光主体材料必须有适当的三线态能级,即T1。优选的,本发明公开的三联苯并环戊二烯类化合物,其T1≥2.2eV,较好是≥2.4eV,更好是≥2.6eV,更更好≥2.65eV,最好是≥2.7eV。
通常,有机化合物的三线态能级T1取决于化合物中具有最大共轭体系的分结构。一般地,T1随共轭体系的增大而递减。
优选的,通式(1)中,如通式(1a)所示的分结构中的一个具有最大的共轭体系:
优选的,按照通式(1a)的分结构在去除取代基的情况下,其环原子数不超过36个,较好为不超过30个,更好为不超过26个,最好为不超过20个。
优选的,按照通式(1a)的分结构,其T1≥2.3eV,较好是≥2.5eV,更好是≥2.7eV,最好是≥2.75eV。
作为磷光主体材料希望有好的热稳定性。
一般的,本发明公开的三联苯并环戊二烯类化合物的玻璃化温度Tg≥100℃。
优选的,本发明公开的三联苯并环戊二烯类化合物的玻璃化温度Tg≥120℃。
较优选的,本发明公开的三联苯并环戊二烯类化合物的玻璃化温度Tg≥140℃。
更优选的,本发明公开的三联苯并环戊二烯类化合物的玻璃化温度Tg≥160℃。
最优选的,本发明公开的三联苯并环戊二烯类化合物的玻璃化温度Tg≥180℃。
该类化合物的合成,一般可以把中心基团L做成带三个酰氯基团的中间体,再用傅克反应上带苯-Rx的侧基;把中心基团做好之后,再SP3碳原子的上部基团做成锂盐或格式试剂,进攻中心基团上的羰基,然后再进行关环反应,就可以得到目标化合物。
具体的,本发明公开的三联苯并环戊二烯类化合物选自如下结构式中的一个:
优选的,本发明公开的三联苯并环戊二烯类化合物是一种小分子材料。
本文中所定义的术语“小分子”是指不是聚合物,低聚物,树枝状聚合物,或共混物的分子。特别是,小分子中没有重复结构。小分子的分子量≤3000克/摩尔,较好是≤2000克/摩尔,最好是≤1500克/摩尔。
高聚物,即Polymer,包括均聚物(homopolymer),共聚物(copolymer),镶嵌共聚物(block copolymer)。另外在本发明中,高聚物也包括树状物(dendrimer),有关树状物的合成及应用请参见[Dendrimers and Dendrons,Wiley-VCH Verlag GmbH&Co.KGaA,2002,Ed.George R.Newkome,Charles N.Moorefield,Fritz Vogtle.]。
共轭高聚物(conjugated polymer)是一种高聚物,共轭高聚物的主链backbone主要是由C
原子的sp2杂化轨道构成,著名的例子有:聚乙炔polyacetylene和poly(phenylene vinylene),其主链上的C原子的也可以被其他非C原子取代,而且当主链上的sp2杂化被一些自然的缺陷打断时,仍然被认为是共轭高聚物。另外在本发明中共轭高聚物也包括主链上包含有芳基胺(aryl amine)、芳基磷化氢(aryl phosphine)及其他杂环芳烃(heteroarmotics)、有机金属络合物(organometallic complexes)等。
本发明还涉及一种高聚物,至少包含上述具有通式(1)所示的重复单元。
优选的,高聚物为非共轭高聚物,具有通式(1)的三联苯并环戊二烯类结构单元在高聚物的侧链上。
优选的,高聚物是共轭高聚物。
本发明还涉及一种混合物,包括上述三联苯并环戊二烯类化合物或上述高聚物,以及有机功能材料。
有机功能材料包括:空穴(也称电洞)注入或传输材料(HIM/HTM)、空穴阻挡材料(HBM)、电子注入或传输材料(EIM/ETM)、电子阻挡材料(EBM)、有机主体材料(Host)、单重态发光体(荧光发光体)、重态发光体(磷光发光体),特别是发光有机金属络合物和有机染料。例如在WO2010135519A1、US20090134784A1和WO 2011110277A1中对各种有机功能材料有详细的描述,特此将此3专利文件中的全部内容并入本文作为参考。
有机功能材料可以选自小分子和高聚物材料。
混合物中,三联苯并环戊二烯类化合物的含量为50~99.9wt%,优选为60~97wt%,更优选为70至95wt%,最优选为70至90wt%。
优选的,混合物包括上述三联苯并环戊二烯类化合物或上述高聚物,以及磷光发光材料。
优选的,混合物包括上述三联苯并环戊二烯类化合物或上述高聚物,以及TADF材料。
优选的,混合物包括上述三联苯并环戊二烯类化合物或上述高聚物,以及磷光发光材料和TADF材料。
优选的,混合物包括上述三联苯并环戊二烯类化合物或上述高聚物,以及荧光发光材料。
优选的,混合物包括上述三联苯并环戊二烯类化合物或上述高聚物,以及发光量子点。
下面对荧光发光材料或单重态发光体,磷光发光材料或三重态发光体,TADF材料和发光量子点作一些较详细的描述(但不限于此)。
1、单重态发光体(Singlet Emitter)
单重态发光体往往有较长的共轭π电子系统。迄今,已有许多例子,例如在JP2913116B和WO2001021729A1中公开的苯乙烯胺及其衍生物,和在WO2008/006449和WO2007/140847中公开的茚并芴及其衍生物。
优选的,单重态发光体可选自一元苯乙烯胺、二元苯乙烯胺、三元苯乙烯胺、四元苯
乙烯胺、苯乙烯膦、苯乙烯醚和芳胺。
一元苯乙烯胺为一种化合物,它包含一个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。
二元苯乙烯胺为一种化合物,它包含二个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。
三元苯乙烯胺为一种化合物,它包含三个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。
四元苯乙烯胺为一种化合物,它包含四个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。
优选的,苯乙烯是二苯乙烯,其可能会进一步被取代。
相应的膦类和醚类的定义与胺类相似。
芳基胺或芳香胺为一种化合物,包含三个直接联接氮的无取代或取代的芳香环或杂环系统。这些芳香族或杂环的环系统中至少有一个优选于稠环系统,并最好有至少14个芳香环原子。其中优选的例子有芳香蒽胺,芳香蒽二胺,芳香芘胺,芳香芘二胺,芳香屈胺和芳香屈二胺。
芳香蒽胺为一种化合物,其中一个二元芳基胺基团直接联到蒽上,最好是在9的位置上。
芳香蒽二胺为一种化合物,其中二个二元芳基胺基团直接联到蒽上,最好是在9,10的位置上。
芳香芘胺、芳香芘二胺、芳香屈胺和芳香屈二胺的定义类似,其中二元芳基胺基团最好联到芘的1或1,6位置上。
基于乙烯胺及芳胺的单重态发光体的例子,也是优选的例子,可在下述专利文件中找到:WO2006/000388,WO2006/058737,WO2006/000389,WO2007/065549,WO2007/115610,US7250532 B2,DE102005058557 A1,CN1583691 A,JP08053397 A,US6251531 B1,US2006/210830 A,EP1957606 A1和US2008/0113101 A1,特此上述列出的专利文件中的全部内容并入本文作为参考。
基于均二苯乙烯极其衍生物的单重态发光体的例子有US 5121029。
进一步的优选的单重态发光体可选于茚并芴-胺和茚并芴-二胺,如WO 2006/122630所公开的,苯并茚并芴-胺和苯并茚并芴-二胺,如WO 2008/006449所公开的,二苯并茚并芴-胺和二苯并茚并芴-二胺,如WO2007/140847所公开的。
其他可用作单重态发光体的材料还包括多环芳烃化合物,特别是如下化合物的衍生物:蒽如9,10-二(2-萘并蒽),萘,四苯,氧杂蒽,菲,芘(如2,5,8,11-四-t-丁基苝),茚并芘,苯撑如(4,4’-双(9-乙基-3-咔唑乙烯基)-1,1’-联苯),二茚并芘,十环烯,六苯并苯,芴,螺二芴,芳基芘(如US20060222886),亚芳香基乙烯(如US5121029,US5130603),环戊二烯如四苯基环戊二烯,红荧烯,香豆素,若丹明,喹吖啶酮,吡喃如4(二氰基亚甲基)-6-(4-对二
甲氨基苯乙烯基-2-甲基)-4H-吡喃(DCM),噻喃,双(吖嗪基)亚胺硼化合物(US 2007/0092753 A1),双(吖嗪基)亚甲基化合物,carbostyryl化合物,噁嗪酮,苯并恶唑,苯并噻唑,苯并咪唑及吡咯并吡咯二酮。一些单重态发光体的材料可在下述专利文件中找到:US 20070252517 A1,US 4769292,US 6020078,US 2007/0252517 A1,US 2007/0252517 A1。特此将上述列出的专利文件中的全部内容并入本文作为参考。
在下面的表中列出一些合适的单重态发光体的例子:
2、热激活延迟荧光发光材料(TADF):
传统有机荧光材料只能利用电激发形成的25%单线态激子发光,器件的内量子效率较低(最高为25%)。尽管磷光材料由于重原子中心强的自旋-轨道耦合增强了系间穿越,可以有效利用电激发形成的单线态激子和三线态激子发光,使器件的内量子效率达到100%。但磷光材料昂贵,材料稳定性差,器件效率滚降严重等问题限制了其在OLED中的应用。热激活延迟荧光发光材料是继有机荧光材料和有机磷光材料之后发展的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(ΔEst),三线态激子可以通过反系间穿越转变成单线态激子发光。这可以充分利用电激发下形成的单线态激子和三线态激子。器件内量子效率可达到100%。
TADF材料需要具有较小的单线态-三线态能级差,一般是ΔEst<0.3eV,较好是ΔEst<0.2eV,更好是ΔEst<0.1eV,最好是ΔEst<0.05eV。在一个优先的实施方案中,TADF有较好
的荧光量子效率。一些TADF发光的材料可在下述专利文件中找到:CN103483332(A),TW201309696(A),TW201309778(A),TW201343874(A),TW201350558(A),US20120217869(A1),WO2013133359(A1),WO2013154064(A1),Adachi,et.al.Adv.Mater.,21,2009,4802,Adachi,et.al.Appl.Phys.Lett.,98,2011,083302,Adachi,et.al.Appl.Phys.Lett.,101,2012,093306,Adachi,et.al.Chem.Commun.,48,2012,11392,Adachi,et.al.Nature Photonics,6,2012,253,Adachi,et.al.Nature,492,2012,234,Adachi,et.al.J.Am.Chem.Soc,134,2012,14706,Adachi,et.al.Angew.Chem.Int.Ed,51,2012,11311,Adachi,et.al.Chem.Commun.,48,2012,9580,Adachi,et.al.Chem.Commun.,48,2013,10385,Adachi,et.al.Adv.Mater.,25,2013,3319,Adachi,et.al.Adv.Mater.,25,2013,3707,Adachi,et.al.Chem.Mater.,25,2013,3038,Adachi,et.al.Chem.Mater.,25,2013,3766,Adachi,et.al.J.Mater.Chem.C.,1,2013,4599,Adachi,et.al.J.Phys.Chem.A.,117,2013,5607,特此将上述列出的专利或文章文件中的全部内容并入本文作为参考。
在下面的表中列出一些合适的TADF发光材料的例子:
3、三重态发光体(Triplet Emitter)
三重态发光体也称磷光发光体。
优选的,三重态发光体是有通式M(L)n的金属络合物,其中M是金属原子,L是有机
配体,L通过一个或多个位置键接或配位连接到M上,n为正整数,n优选为1、2、3、4、5或6。
优选的,这些金属络合物通过一个或多个位置联接到一个聚合物上,最好是通过有机配体。
优选的,M选自过渡金属元素、镧系元素或锕系元素。
更优选的,M选自Ir,Pt,Pd,Au,Rh,Ru,Os,Sm,Eu,Gd,Tb,Dy,Re,Cu或Ag。
特别优选的,M选自Os,Ir,Ru,Rh,Re,Pd或Pt。
优选的,三重态发光体包含有螯合配体(即配体),通过至少两个结合点与金属配位。
更优选的,三重态发光体包含有两个或三个相同或不同的双齿或多齿配体。螯合配体有利于提高金属络合物的稳定性。
有机配体可选自苯基吡啶衍生物、7,8-苯并喹啉衍生物、2(2-噻吩基)吡啶衍生物、2(1-萘基)吡啶衍生物或2苯基喹啉衍生物。有机配体可以被取代,例如被含氟或三氟甲基取代。
辅助配体可选自乙酸丙酮或苦味酸。
优选的,可用作三重态发光体的金属络合物有如下形式:
其中,M为金属,M选自过渡金属元素、镧系元素或锕系元素;
Ar1每次出现时可以是相同或不同,Ar1是一个环状基团,Ar1中至少包含有一个施主原子(即有一孤对电子的原子,如氮或磷),Ar1通过施主原子与M配位连接;
Ar2每次出现时可以是相同或不同,Ar2是一个环状基团,Ar2中至少包含有一个C原子,Ar2通过C原子与M连接;
Ar1和Ar2由共价键联接在一起,Ar1和Ar2可各自携带一个或多个取代基团,它们也可再通过取代基团联接在一起;
L每次出现时可以是相同或不同,L是一个辅助配体,L优选为双齿螯合配体,最好是单阴离子双齿螯合配体;
M为1、2或3,M优选为2或3,M特别优选为3;
n为0、1或2,n优选为0或1,n特别优选为0。
一些三重态发光体的材料极其应用的例子可在下述专利文件和文献中找到:WO 200070655,WO 200141512,WO 200202714,WO 200215645,EP 1191613,EP 1191612,EP 1191614,WO 2005033244,WO 2005019373,US 2005/0258742,WO 2009146770,WO 2010015307,WO 2010031485,WO 2010054731,WO 2010054728,WO 2010086089,WO 2010099852,WO 2010102709,US 20070087219 A1,US 20090061681 A1,US 20010053462 A1,Baldo,Thompson et al.Nature 403,(2000),750-753,US 20090061681 A1,US 20090061681 A1,Adachi et al.Appl.Phys.Lett.78(2001),1622-1624,J.Kido et al.Appl.Phys.Lett.65(1994),2124,Kido et al.Chem.Lett.657,1990,US 2007/0252517 A1,Johnson et al.,JACS 105,1983,1795,Wrighton,JACS 96,1974,998,Ma et al.,Synth.Metals 94,1998,245,US 6824895,US
7029766,US 6835469,US 6830828,US 20010053462 A1,WO 2007095118 A1,US 2012004407A1,WO 2012007088A1,WO2012007087A1,WO 2012007086A1,US 2008027220A1,WO 2011157339A1,CN 102282150A,WO 2009118087A1。特此将上述列出的专利文件和文献中的全部内容并入本文作为参考。
在下面的表中列出一些合适的三重态发光体的例子:
4、发光量子点
一般地,发光量子点可以在波长380纳米到2500纳米之间发光。例如,已发现,具有CdS核的量子点的发光波长位于约400纳米到560纳米范围;具有CdSe核的量子点的发光波长位于约490纳米到620纳米范围;具有CdTe核的量子点的发光波长位于约620纳米到680纳米范围;具有InGaP核的量子点的发光波长位于约600纳米到700纳米范围;具有PbS核的量子点的发光波长位于约800纳米到2500纳米范围;具有PbSe核的量子点的发光波长位于约1200纳米到2500纳米范围;具有CuInGaS核的量子点的发光波长位于约600纳米到680纳米范围;具有ZnCuInGaS核的量子点的发光波长位于约500纳米到620纳米范围;具有CuInGaSe核的量子点的发光波长位于约700纳米到1000纳米范围。
在一个优选的实施例中,量子点材料包括能够发出发光峰值波长位于450nm~460nm的蓝光量子点、发光峰值波长位于520nm~540nm的绿光量子点和发光峰值波长位于615nm~630nm的红光量子点中的一种或一种以上的混合物。
量子点可以选自特殊的化学组成、形貌结构和/或大小尺寸,以获得在电刺激下发出所需波长的光。关于量子点的发光性质与其化学组成、形貌结构和/或大小尺寸的关系可以参见Annual Review of Material Sci.,2000,30,545-610;Optical Materials Express.,2012,2,594-628;Nano Res,2009,2,425-447。特此将上述列出的专利文件中的全部内容并入本文作为参考。
量子点的窄的粒径分布能使量子点具有更窄的发光光谱(J.Am.Chem.Soc.,1993,115,8706;US 20150108405)。此外,根据所采用的化学组成和结构的不同,量子点的尺寸需在上述的尺寸范围内做相应调节,以获得所需波长的发光性质。
优选的,发光量子点是半导体纳米晶体。在一个实施例中,半导体纳米晶体的尺寸为约5纳米到约15纳米的范围内。此外,根据所采用的化学组成和结构的不同,量子点的尺寸需在上述的尺寸范围内做相应调节,以获得所需波长的发光性质。
半导体纳米晶体包括至少一种半导体材料,其中半导体材料可选为元素周期表IV族、II-VI族、II-V族、III-V族、III-VI族、IV-VI族、I-III-VI族、II-IV-VI族、II-IV-V族二元或多元半导体化合物或他们的混合物。
具体的,半导体材料的实例包括,但不限制于:IV族半导体化合物,由单质Si、Ge和二元化合物SiC、SiGe组成;II-VI族半导体化合物,由二元化合物包括CdSe、CdTe、CdO、CdS、CdSe、ZnS、ZnSe、ZnTe、ZnO、HgO、HgS、HgSe、HgTe,三元化合物包括CdSeS、CdSeTe、CdSTe、CdZnS、CdZnSe、CdZnTe、CgHgS、CdHgSe、ZnSeS、ZnSeTe、ZnSTe、HgSeS、HgSeTe、HgSTe、HgZnS、HgSeSe及四元化合物包括CgHgSeS、CdHgSeTe、CgHgSTe、CdZnSeS、CdZnSeTe、HgZnSeTe、HgZnSTe、CdZnSTe、HgZnSeS、组成;III-V族半导体化合物,由二元化合物包括AlN、AlP、AlAs、AlSb、GaN、GaP、GaAs、GaSb、InN、InP、InAs、InSb,三元化合物包括AlNP、AlNAs、AlNSb、AlPAs、AlPSb、GaNP、GaNAs、GaNSb、GaPAs、GaPSb、InNP、InNAs、InNSb、InPAs、InPSb、和四元化合物包括GaAlNAs、GaAlNSb、GaAlPAs、GaInNP、GaInNAs、GaInNSb、GaInPAs、GaInPSb、InAlNP、InAlNAs、InAlNSb、InAlPAs、InAlPSb组成;IV-VI族半导体化合物,由二元化合物包括SnS、SnSe、SnTe、PbSe、PbS、PbTe,三元化合物包括SnSeS、SnSeTe、SnSTe、SnPbS、SnPbSe、SnPbTe、PbSTe、PbSeS、PbSeTe和四元化合物包括SnPbSSe、SnPbSeTe、SnPbSTe组成。
优选的,发光量子点包含有II-VI族半导体化合物,更优选包括CdSe,CdS,CdTe,ZnO,ZnSe,ZnS,ZnTe,HgS,HgSe,HgTe,CdZnSe及它们的任何组合。在合适的实施方案中,由于CdSe,CdS的合成相对成熟而将此材料用作用于可见光的发光量子点。
优选的,发光量子点包含有III-V族半导体化合物,更优选包括InAs,InP,InN,GaN,InSb,InAsP,InGaAs,GaAs,GaP,GaSb,AlP,AlN,AlAs,AlSb,CdSeTe,ZnCdSe及它们的任何组合。
优选的,发光量子点包含有IV-VI族半导体化合物,更优选包括PbSe,PbTe,PbS,PbSnTe,Tl2SnTe5及它们的任何组合。
优选的,量子点为核壳结构,核与壳分别相同或不同地包括一种或多种半导体材料。
更有选的,具有核壳结构的量子点中,壳可以包括单层或多层的结构。壳包括一种或多种与核相同或不同的半导体材料。较优选的,壳具有约1到20层的厚度。更优选的,壳具有约5到10层的厚度。在某些实施例中,在量子点核的表面生长两种或两种以上的壳。
优选的,用于壳的半导体材料具有比核更大的带隙。特别优选的,壳核具有I型的半导体异质结结构。
优选的,用于壳的半导体材料具有比核更小的带隙。
优选的,用于壳的半导体材料具有与核相同或接近的原子晶体结构。这样的选择有利于减小核壳间的应力,使量子点更为稳定。
合适的采用核壳结构的发光量子点的例子(但不限制于)有:
红光:CdSe/CdS,CdSe/CdS/ZnS,CdSe/CdZnS等
绿光:CdZnSe/CdZnS,CdSe/ZnS等
蓝光:CdS/CdZnS,CdZnS/ZnS等
本发明的另一个目的是为印刷OLED提供材料解决方案。
优选的,本发明公开的三联苯并环戊二烯类化合物的分子量≥700mol/kg,优选≥900mol/kg,很优选≥900mol/kg,更优选≥1000mol/kg,最优选≥1100mol/kg。
优选的,在25℃时,本发明公开的三联苯并环戊二烯类化合物在甲苯中的溶解度≥10mg/mL,优选≥15mg/mL,最优选≥20mg/mL。
本发明进一步涉及一种组合物或油墨,包含上述三联苯并环戊二烯类化合物、上述高聚物或上述混合物,以及有机溶剂。
本发明进一步提供一种从溶液中制备包含有按照本发明的化合物或高聚物的薄膜。
用于印刷工艺时,油墨的粘度,表面张力是重要的参数。合适的油墨的表面张力参数适合于特定的基板和特定的印刷方法。
优选的,油墨在工作温度或在25℃下的表面张力约在19dyne/cm到50dyne/cm范围,更优选在22dyne/cm到35dyne/cm范围,最优选在25dyne/cm到33dyne/cm范围。
优选的,油墨在工作温度或25℃下的粘度约在1cps到100cps范围,较优选在1cps到50cps范围,更优选在1.5cps到20cps范围,最优选在4.0cps到20cps范围。如此配制的组合物将适合于喷墨印刷。
粘度可以通过不同的方法调节,如通过合适的溶剂选取和油墨中功能材料的浓度。按照本发明的包含有所述地化合物或高聚物的油墨可方便人们将印刷油墨按照所用的印刷方法在适当的范围调节。
一般地,组合物中三联苯并环戊二烯类化合物或高聚物的重量比为0.3%~30wt%范围,较好的为0.5%~20wt%范围,更好的为0.5%~15wt%范围,更更好的为0.5%~10wt%范围,最好的为1%~5wt%范围。
优选的,有机溶剂选自基于芳族或杂芳族的溶剂,特别是脂肪族链/环取代的芳族溶剂、芳族酮溶剂或芳族醚溶剂。
较优选的,有机溶剂选自基于芳族或杂芳族的溶剂,具体包括:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二甲苯、间二甲苯、对二甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、1-甲氧基萘、环己基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-
三氯苯、1,3-二丙氧基苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、二苄醚等;基于酮的溶剂:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮,异佛尔酮、2,6,8-三甲基-4-壬酮、葑酮、2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、佛尔酮、二正戊基酮;芳族醚溶剂:3-苯氧基甲苯、丁氧基苯、苄基丁基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚、戊醚c己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚;酯溶剂:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。
更优选的,有机溶剂选自脂肪族酮,具体包括:2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、佛尔酮、二正戊基酮等;或脂肪族醚,例如,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚等。
优选的,油墨还包含有另一种有机溶剂。另一种有机溶剂的例子,包含(但不限于):甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
优选的,组合物为溶液。
优选的,组合物为悬浮液。
本发明还涉及组合物作为印刷油墨在制备有机电子器件时的用途,优选的是通过打印或涂布的制备方法。
其中,适合的打印或涂布技术包含(但不限于)喷墨打印,喷印(Nozzle Printing),活版印刷,丝网印刷,浸涂,旋转涂布,刮刀涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印,喷印刷(Nozzle printing),狭缝型挤压式涂布等。首选的是喷墨印刷,狭缝型挤压式涂布,喷印刷及凹版印刷。溶液或悬浮液可以另外包含一个或多个组份例如表面活性化合物,润滑剂,润湿剂,分散剂,疏水剂,粘接剂等,用于调
节粘度,成膜性能,提高附着性等。有关打印技术,及其对有关溶液的相关要求,如溶剂及浓度,粘度等,的详细信息请参见Helmut Kipphan主编的《印刷媒体手册:技术和生产方法》(Handbook of Print Media:Technologies and Production Methods),ISBN 3-540-67326-1。
基于上述化合物,本发明还提供一种上述三联苯并环戊二烯类化合物或上述高聚物在有机电子器件的应用。
有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode)等,特别是OLED。
优选的,上述三联苯并环戊二烯类化合物或上述高聚物用于OLED器件的发光层中。
本发明进一步涉及一种有机电子器件,包含上述三联苯并环戊二烯类化合物或上述高聚物。
一般的,有机电子器件包含阴极、阳极及位于阴极和阳极之间的功能层,其中,功能层包含上述三联苯并环戊二烯类化合物或上述高聚物。
有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode)。
较优选的,有机电子器件为电致发光器件,特别是OLED,有机电子器件包括基片、阳极、发光层和阴极,有机电子器件择性的还可包含空穴传输层和/或电子传输层。
优选的,空穴传输层中包含上述三联苯并环戊二烯类化合物或上述高聚物。
优选的,电子传输层中包含上述三联苯并环戊二烯类化合物或上述高聚物。
优选的,发光层中包含上述三联苯并环戊二烯类化合物或上述高聚物。
更优选的,发光层中包含上述三联苯并环戊二烯类化合物或上述高聚物,以及发光材料,发光材料可选于荧光发光体、磷光发光体、TADF材料或发光量子点。
下面对电致发光器件的器件结构做简单描述,但并不限定。
基片可以是不透明或透明。一个透明的基板可以用来制造一个透明的发光元器件。例如可参见,Bulovic等Nature 1996,380,p29,和Gu等,Appl.Phys.Lett.1996,68,p2606。基片可以是刚性的或弹性的。基片可以是塑料、金属、半导体晶片或玻璃。最好是基片有一个平滑的表面。无表面缺陷的基板是特别理想的选择。在一个优选的实施例中,基片是柔性的,可选于聚合物薄膜或塑料,其玻璃化温度Tg为150℃以上,较好是超过200℃,更好是超过250℃,最好是超过300℃。合适的柔性基板的例子有聚(对苯二甲酸乙二醇酯)(PET)和聚乙二醇(2,6-萘)(PEN)。
阳极可包含导电金属、金属氧化物或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个实施例中,阳极的功函数和发光层中的
发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包含但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的,本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包含射频磁控溅射,真空热蒸发,电子束(e-beam)等。在某些实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本发明的器件。
阴极可包含导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。原则上,所有可用作OLED的阴极的材料都可能作为本发明器件的阴极材料。阴极材料的例子包含但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包含射频磁控溅射,真空热蒸发,电子束(e-beam)等。
OLED还可以包含其他功能层,如空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)。适合用于这些功能层中的材料在前面有详细的描述。
在一个优选的实施例中,电致发光器件的发光层包含上述三联苯并环戊二烯类化合物或上述高聚物,并且通过溶液加工的方法制备而成。
电致发光器件的发光波长在300到1000nm之间,较好的是在350到900nm之间,更好的是在400到800nm之间。
本发明还涉及上述有机电子器件在各种电子设备中的应用,包含,但不限于,显示设备、照明设备、光源、传感器等等。
下面将结合优选实施例对本发明进行了说明,但本发明并不局限于下述实施例,应当理解,所附权利要求概括了本发明的范围在本发明构思的引导下本领域的技术人员应意识到,对本发明的各实施例进行的一定的改变,都将被本发明的权利要求书的精神和范围所覆盖。下面对本发明的化合物的合成方法举例,但本发明并不局限于下述实施例。
实施例1、化合物(2-2)的合成
1)
将(26.5g,100mmol)的1,3,5-苯三甲酰氯和(62.8g,400mmol)的溴苯加入500mL两口瓶中,搅拌下分批加入(66.5g,500mmol)无水氯℃化铝,加毕,常温搅拌反应0.5小时,加热90℃反应两个小时,结束反应,将反应产物慢慢加入到盐酸水溶液中,抽滤,滤渣用二氯甲烷/乙醇混合溶液重结晶,产率90%。
2)
将预先制备好的(45mmol)2-溴化镁联苯的四氢呋喃溶液,加入到(18.8g,20mmol)的化合物2-2-4的THF溶液中,加热到60℃,反应12小时,再缓慢加入60mL的去离子水,维持温度反应0.5小时,结束反应,旋转蒸发掉大部分反应液中的THF,用二氯甲烷萃取,盐酸水溶液洗一次,水洗两次,有机相用无水硫酸镁干燥,旋干,无需进一步纯化,直接用于下一步的反应。
3)
将上一步得到的(27.2g,25mmol)的化合物2-2-7,氢溴酸20mL和乙酸40mL加入到150mL的单口瓶中,搅拌加热120℃反应两个小时,结束反应,有固体析出,将反应液中的上层液体倒掉,往固体中加入甲醇,抽滤,滤渣用二氯甲烷/乙醇混合溶液重结晶,产率90%。
4)
将(15.5g,15mmol)的化合物2-2-9,(7.3g,60mmol)的苯硼酸,(15.9g,150mmol)碳酸钠,(0.48g,1.5mmol)四丁基溴化铵,(0.52g,0.45mmol)四(三苯基膦)钯,60mL1,4-二氧六环和10mL水加入150mL两口瓶中,加热90℃搅拌反应12个小时,结束反应,将反应液加入到400mL水中,抽滤,滤渣用二氯甲烷/石油醚混合溶液重结晶,产率90%。
实施例2、化合物(2-6)的合成
1)
将(12.78g,30mmol)的化合物(2-2-8)、(25.4g,100mmol)的联硼酸频那醇酯,(1.5mmol)Pd(dppf)Cl2、(100mmol)醋酸钾和150mL 1,4-二氧六环加入300mL两口瓶中,加热110℃搅拌反应12个小时,结束反应,将反应液加入到500mL水中,抽滤,收集滤渣拌硅胶过柱进行纯化,产率80%。
2)
氮气环境下,将(11.77g,10mmol)的化合物(2-6-1)、(9.38g,35mmol)的化合物(2-6-2)、(4.24g,40mmol)碳酸钠、(1.6g,5mmol)四丁基溴化铵,(0.52g,0.45mmol)四(三苯基膦)钯,100mL 1,4-二氧六环和20mL水加入250mL两口瓶中,加热90℃搅拌反应12个小时,结束反应,将反应液加入到400mL水中,用二氯甲烷萃取溶解水洗3遍,收集有机液拌硅胶过柱进行纯化,产率85%。
实施例3、有机化合物的能量结构
有机材料的能级可通过量子计算得到,比如利用TD-DFT(含时密度泛函理论)通过Gaussian03W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。首先用半经验方法“Ground State/Semi-empirical/Default Spin/AM1”(Charge 0/Spin Singlet)来优化分子几何结构,然后有机分子的能量结构由TD-DFT(含时密度泛函理论)方法算得“TD-SCF/DFT/Default Spin/B3PW91”与基组“6-31G(d)”(Charge 0/Spin Singlet)。HOMO和LUMO能级按照下面的校准公式计算,S1和T1直接使用。
HOMO(eV)=((HOMO(G)×27.212)-0.9899)/1.1206
LUMO(eV)=((LUMO(G)×27.212)-2.0041)/1.385
其中HOMO(G)和LUMO(G)是Gaussian 03W的直接计算结果,单位为Hartree。结果如表一所示:
表一
实施例4、溶液加工OLED器件的制备及表征
溶液加工OLED器件的结构如下:为ITO/PEDOT(80nm)/TFB(20nm)/主体材料:Emitter(15wt%)(45nm)/B3PYMPM(35)/LiF(1nm)/Al(100nn)。其中可溶Emitter如下式所示,
空穴传输材料TFB(H.W.SandsCorp.)为
PEDOT、TFB和发光层都通过旋涂而成。空穴传输层TFB用的是TFB在甲苯中的溶液,溶度为6mg/mL。发光层用的是混合物,主体材料:Emitter(15wt%)在甲苯中的溶液,溶度为20mg/mL。B3PYMPM(40nm),LiF(1nm),Al(100nm)在高真空(1×10-6毫巴)中热蒸镀而成;最后器件在氮气手套箱中用紫外线硬化树脂封装。
表二
OLED器件 | 主体材料 | 最大外部量子效率% |
OLED1 | (2-2) | 15.2% |
OLED2 | (2-6) | 13.7% |
OLED3 | Ref1 | 6% |
常用的蒸镀型主体材料CBP,由于在通常溶剂如甲苯中的溶解性很差,没法制成OLED器件。主体材料Ref1溶于甲苯,但可能由于分子量太小,成膜性能不好。而用本发明的主体材料(2-2)和(2-6)在甲苯中的溶解性很好,且具有非常好的成膜性能。
各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及外部量子效率。如表二所示,OLED1和OLED2的发光效率大大高于OLED。同时,OLED1和OLED2的寿命分别是OELD3的30倍和25倍以上。可见,采用本发明的有机化合物作为可溶主体制备的OLED器件,其效率和寿命得到大大提高。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对本发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (19)
- 一种三联苯并环戊二烯类化合物,其特征在于,具有如下通式(1):其中,L为连接单元,L选自碳原子数为6~40的芳香基团或碳原子数为3~40的杂芳基团;A1、A2或A3选自碳原子数为6~30的芳香基团或碳原子数为3~30的杂芳基团;R1、R2或R3选自H、D、F、CN、碳原子数为1~30的烷基、碳原子数为3~30的环烷基、碳原子数为6~60芳香族烃基、碳原子数为3~60的芳香族杂环基,并且R1、R2或R3上的一个或多个位置可以被H、D、F、CN、烷基、芳烷基、烯基、炔基、腈基、胺基、硝基、酰基、烷氧基、羰基、砜基、环烷基或羟基取代。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,所述三联苯并环戊二烯类化合物的玻璃化温度Tg≥100℃。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,L选自苯、萘、蒽、菲、芘、吡啶、嘧啶、三嗪、芴、硫芴、硅芴、咔唑、噻吩、呋喃、噻唑、三苯胺、三苯基氧磷、四苯基硅、螺芴或螺硅芴。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,L选自如下任一结构单元或如下任一结构单元进一步被取代形成的取代单元:
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,A1、A2或A3选自如下结构基团中的一种:其中,X选自CR1或N;Y选自CR2R3、SiR2R3、NR2、C(=O)、S或O;R1、R2或R3选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链的烷基、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基或硫代烷氧基基团、具有3至20个C原子的是甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团、氨基甲酰基基团、卤甲酰基基团、甲酰基基团、异氰基基团、异氰酸酯基团、硫氰酸酯基团、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、Br、F、可交联的基团、具有5至40个环原子的芳族环系、具有5至40个环原子的杂芳族环系、具有5至40个环原子的取代的芳族环系、具有5至40个环原子的取代的杂芳族环系、具有5至40个环原子的芳氧基基团和具有5至40个环原子的杂芳氧基基团中的一种或一种以上的组合。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,A1、A2或A3选自如下结构基团或如下结构基团进一步被取代形成的取代基团中的一种:其中,X选自N(R)、B(R)、C(R)2、Si(R)2、O、S、C=N(R)、C=C(R)2、P(R)、P(=O)R、S=O、SO2或无,X优选为N(R)、C(R)2、O或S;R选自碳原子数为1~30的烷基、碳原子数为3~30的环烷基、碳原子数为6~60芳香族烃基或碳原子数为3~60的芳香族杂环基,并且R上的一个或多个位置可以被H、D、F、CN、烷基、芳烷基、烯基、炔基、腈基、胺基、硝基、酰基、烷氧基、羰基、砜基、环烷基或羟基取代。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,A1、A2或A3选自如下结构基团或如下结构基团进一步被取代形成的取代基团中的一种:
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,R1、R2或R3选 自甲基、苯、萘、蒽、菲、芘、吡啶、嘧啶、三嗪、芴、硫芴、硅芴、咔唑、噻吩、呋喃、噻唑、三苯胺、三苯基氧磷,四苯基硅、螺芴或螺硅芴。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,所述三联苯并环戊二烯类化合物选自具有如下结构式的化合物中的一种:其中,L、R1、R2和R3的含义如上所述。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,所述三联苯并环戊二烯类化合物选自具有如下结构式的化合物中的一种:其中A1、A2、A3、R1、R2和R3的含义如上所述。
- 根据权利要求1所述的三联苯并环戊二烯类化合物,其特征在于,所述三联苯并环戊二烯类化合物选自具有如下结构式的化合物中的一种:
- 一种高聚物,其特征在于,所述高聚物至少包含一个如权利要求1~10中任一项所述的三联苯并环戊二烯类化合物所包括的如通式(1)所示的重复单元。
- 一种混合物,其特征在于,包括一种如权利要求1~11中任一项所述的三联苯并环戊二烯类化合物或如权利要求12所述的高聚物,及另一种有机功能材料。
- 根据权利要求13所述的混合物,其特征在于,所述的另一种有机功能材料选自空穴注入材料、空穴传输材料、电子注入材料、电子传输材料、空穴阻挡材料、电子阻挡材料、有机主体材料、单重态发光体、重态发光体、发光有机金属络合物和有机染料中的至少一种。
- 一种组合物,其特征在于,包括一种如权利要求1~11中任一项所述的三联苯并环戊二烯类化合物或如权利要求12所述的高聚物,及一种有机溶剂。
- 一种有机电子器件,其特征在于,包括如权利要求1~11中任一项所述的三联苯并环戊二烯类化合物或如权利要求12所述的高聚物。
- 根据权利要求16所述的有机电子器件,其特征在于,所述有机电子器件选自有机发光二极管、有机光伏电池、有机发光电池、有机场效应管、有机发光场效应管、有机传感器和有机等离激元发射二极管中的一种。
- 根据权利要求16所述的有机电子器件,其特征在于,该有机电子器件是一电致发光器件,该电致发光器件包含有一发光层,所述发光层中包含有一如权利要求1~11中任一项所述的三联苯并环戊二烯类化合物或如权利要求12所述的高聚物。
- 根据权利要求16所述的有机电子器件,其特征在于,该有机电子器件是一电致发光器件,该电致发光器件包含有一空穴传输层和电子传输层中的一种或两种;所述空穴传输层中包含有一如权利要求1~11中任一项所述的三联苯并环戊二烯类化合物或如权利要求12所述的高聚物;所述电子传输层中包含有一如权利要求1~11中任一项所述的三联苯并环戊二烯类化合物或如权利要求12所述的高聚物。
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