CN105367544B - 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 - Google Patents
含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 Download PDFInfo
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- CN105367544B CN105367544B CN201510646336.XA CN201510646336A CN105367544B CN 105367544 B CN105367544 B CN 105367544B CN 201510646336 A CN201510646336 A CN 201510646336A CN 105367544 B CN105367544 B CN 105367544B
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- benzo
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- luxuriant
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- 125000005605 benzo group Chemical group 0.000 title claims abstract description 103
- 239000003205 fragrance Substances 0.000 title abstract description 58
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title abstract description 49
- 229930192474 thiophene Natural products 0.000 title abstract description 26
- -1 furan compound Chemical class 0.000 title abstract description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 239000010410 layer Substances 0.000 claims description 99
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 90
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 47
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 32
- 239000012044 organic layer Substances 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 22
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 18
- 239000004305 biphenyl Substances 0.000 claims description 17
- 235000010290 biphenyl Nutrition 0.000 claims description 16
- 125000005561 phenanthryl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 69
- 239000000203 mixture Substances 0.000 description 114
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 106
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 47
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 41
- 239000007787 solid Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 36
- 239000000376 reactant Substances 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000012299 nitrogen atmosphere Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000004327 boric acid Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 16
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000012265 solid product Substances 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 150000003384 small molecules Chemical class 0.000 description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 150000002240 furans Chemical class 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 6
- 229920000736 dendritic polymer Polymers 0.000 description 6
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000027756 respiratory electron transport chain Effects 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 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 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229940049706 benzodiazepine Drugs 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 235000019798 tripotassium phosphate Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 150000008648 triflates Chemical class 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 0 *C1=C(C=CC#C2)C2=C(*)*1 Chemical compound *C1=C(C=CC#C2)C2=C(*)*1 0.000 description 3
- JESBGFNZNSEZMR-UHFFFAOYSA-N 1-bromodibenzothiophene Chemical class S1C2=CC=CC=C2C2=C1C=CC=C2Br JESBGFNZNSEZMR-UHFFFAOYSA-N 0.000 description 3
- KQMIWCAOEFUBQK-UHFFFAOYSA-N 1-methoxy-3-phenylbenzene Chemical group COC1=CC=CC(C=2C=CC=CC=2)=C1 KQMIWCAOEFUBQK-UHFFFAOYSA-N 0.000 description 3
- FWMOBNBMZSAAJV-UHFFFAOYSA-N 2,8-diphenyldibenzothiophene Chemical class C1=CC=CC=C1C1=CC=C(SC=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 FWMOBNBMZSAAJV-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000005137 deposition process Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 230000004807 localization Effects 0.000 description 3
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical class COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 2
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 2
- GBRJZKUMODPNGR-UHFFFAOYSA-N 1-methoxy-3-(3-methoxyphenyl)-2-phenylbenzene Chemical group COC1=CC=CC(C=2C(=C(OC)C=CC=2)C=2C=CC=CC=2)=C1 GBRJZKUMODPNGR-UHFFFAOYSA-N 0.000 description 2
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical class ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 2
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 2
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical class C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BLDFKEFDGIYYFJ-UHFFFAOYSA-N [2-(2,6-dimethoxyphenyl)phenyl]phosphonic acid Chemical group P(=O)(O)(O)C1=C(C=CC=C1)C1=C(C=CC=C1OC)OC BLDFKEFDGIYYFJ-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 150000004826 dibenzofurans Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- UEOCICLWNYTZBO-UHFFFAOYSA-N (3-methoxyphenoxy)boronic acid Chemical compound COC1=CC=CC(OB(O)O)=C1 UEOCICLWNYTZBO-UHFFFAOYSA-N 0.000 description 1
- AXNMOBHBEFVSCR-UHFFFAOYSA-N (3-methoxyphenyl)boron Chemical compound [B]C1=CC=CC(OC)=C1 AXNMOBHBEFVSCR-UHFFFAOYSA-N 0.000 description 1
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical class COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KOIFEEYSNGPXPP-UHFFFAOYSA-N 1,2,3-triphenyldibenzothiophene Chemical class C1(=CC=CC=C1)C=1C(=C(C2=C(SC3=C2C=CC=C3)C=1)C1=CC=CC=C1)C1=CC=CC=C1 KOIFEEYSNGPXPP-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical class BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- RPJHLMLHDZFHHY-UHFFFAOYSA-N 2,4,8-triphenyldibenzothiophene Chemical class C1=CC=CC=C1C1=CC=C(SC=2C3=CC(=CC=2C=2C=CC=CC=2)C=2C=CC=CC=2)C3=C1 RPJHLMLHDZFHHY-UHFFFAOYSA-N 0.000 description 1
- DCGQVDFBDSTUML-AWEZNQCLSA-N 2-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidine-1-carbonyl]chromen-4-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1OC2=CC=CC=C2C(C=1)=O DCGQVDFBDSTUML-AWEZNQCLSA-N 0.000 description 1
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- FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明提供了含苯并[9,10]菲的苯并稠合的噻吩化合物。另外，本发明提供了含苯并[9,10]菲的苯并稠合的呋喃化合物。所述化合物可以用于有机发光器件，特别是用作这样的器件的发射层中的主体，或用作这样的器件中的增进层材料，或用作二者。
Description
本申请是申请日为2008年8月7日、申请号为200880106949.2、发明名称为“含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合”的中国发明专利申请(PCT/US2008/072499)的分案申请。
母案申请要求2007年8月8日提交的美国临时申请序列号60/963,944，2007年12月28日提交的美国临时申请序列号61/017,506和2007年12月28日提交的美国临时申请序列号61/017,391的优先权权益，它们的内容通过引用整体明确结合到本申请中。本申请还涉及2007年12月28日提交的国际申请序列号PCT/US07/89131。
所要求保护的发明是由一个或多个如下联合的大学公司研究协议当事人、代表这些当事人和/或与这些当事人相关而完成的：密歇根大学理事会，普林斯顿大学，南加州大学和Universal Display Corporation。所述协议在所要求保护的发明完成日和之前是有效的，并且所要求保护的发明是作为在所述协议的范围内采取的行动的结果而完成的。
发明领域
本发明涉及具有苯并稠合的噻吩和/或苯并稠合的呋喃以及苯并[9,10]菲的新型有机材料。特别地，所述材料具有二苯并噻吩和/或苯并呋喃以及苯并[9,10]菲。所述材料可以被用于发光器件(OLED)。
背景技术
利用有机材料的光电器件由于许多理由越来越为人们所需求。用于制造此类器件的许多材料是相对便宜的，因此有机光电器件具有在成本上比无机器件有优势的可能。另外，有机材料的固有性能如它们的柔性可以使得它们非常适合于特殊应用，如在柔性基材上制造。有机光电器件的例子包括有机发光器件(OLED)、有机光敏晶体管、有机光生伏打电池和有机光检测器。对于OLED，有机材料可以比常规材料有性能优势。例如，有机发射层发光的波长一般可以容易地用合适的掺杂剂调节。
OLED利用薄的有机膜，当对器件施加电压时所述有机膜会发光。OLED正在成为人们越来越感兴趣的技术，用于诸如平板显示器、照明和逆光照明之类的应用中。几种OLED材料和构造已被描述在美国专利5,844,363、6,303,238和5,707,745中，它们的全部内容通过引用结合在本文中。
磷光发射分子的一个应用是全色显示器。这样的显示器的工业标准要求适合发射被称为“饱和”色的特定颜色的像素。特别地，这些标准要求饱和的红、绿和蓝色像素。颜色可以使用本领域中公知的CIE坐标度量。
绿色发射分子的一个实例是三(2-苯基吡啶)合铱，表示为Ir(ppy)3，其具有如下结构:
在该图和本文中后面的图中，我们将由氮至金属(在这里为Ir)的配价键描绘为直线。
在这里使用的术语“有机”包括可用来制造有机光电器件的聚合物材料以及小分子有机材料。“小分子”指不是聚合物的任何有机材料，并且“小分子”实际上可以是相当大的。在一些情况下小分子可以包括重复单元。例如，使用长链烷基作为取代基不会将一个分子从“小分子”类型中排除。小分子也可以被引入聚合物中，例如作为在聚合物骨架上的侧基或作为骨架的一部分。小分子也可以用作树状分子的芯结构部分，该树状分子由在芯结构部分上构建的一系列化学壳组成。树状分子的芯结构部分可以是荧光或磷光小分子发射体。树状分子可以是“小分子”，并且据信目前在OLED领域中使用的所有树状分子是小分子。
在这里使用的“顶部”指最远离基材，而“底部”指最接近基材。当第一层被描述为“布置在”第二层上，所述第一层远离基材来设置。在所述第一和第二层之间可以有其它层，除非规定所述第一层与所述第二层“接触”。例如，阴极可以被描述为“布置在”阳极上，即使在两者之间有各种有机层。
在这里使用的“可溶液处理的”是指能够在液体介质中溶解、分散或输送和/或从液体介质中沉积，无论呈溶液或悬浮液的形式。
当据信一个配位体对发光材料的光活性性能有贡献时，该配位体被称为“光活性的”。
关于OLED和上述定义的更多细节可以见美国专利7,279,704号，该专利的全部内容通过引用结合在本文中。
发明概述
本发明提供了含苯并[9,10]菲的苯并稠合的噻吩化合物。所述化合物可以用于有机发光器件。所述化合物特别可以用作有机发光器件的发射层的主体，用作增进层(enhancement layer)材料，或用作二者。
含苯并[9,10]菲的苯并稠合的噻吩的实例包括具有式(I)、式(II)和式(III)的结构的化合物:
R1、R2和R3独立地选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基、杂芳基和氢。R1、R2和R3各自可以表示多个取代基。R1、R2和R3中至少一个包括苯并[9,10]菲基团。所述苯并[9,10]菲基团可以直接连接到式(I)、(II)或(III)的结构上，但是在所述苯并[9,10]菲基团和所述式(I)、(II)或(III)的结构之间也可以有“间隔基”。
含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃的实例包括具有以下结构的化合物:
X是S或O。优选地，R1、R2和R3是非稠合的取代基，其独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或者无取代。R1、R2和R3各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
有用的含苯并[9,10]菲的苯并稠合的噻吩化合物和含苯并[9,10]菲的苯并稠合的呋喃化合物的更具体的实例包括本文中公开的化合物1G-48G和化合物1-48。所述化合物可以用作有机发光器件的发射层的主体，这样的器件的增进层材料，或二者。
附图简要说明
图1显示了一种有机发光器件。
图2显示了一种不具有单独的电子传输层的颠倒的有机发光器件。
图3显示了含苯并[9,10]菲的苯并稠合的噻吩和/或苯并稠合的呋喃化合物。
详细描述
一般地，OLED包括布置在阳极和阴极之间并且电连接到阳极和阴极上的至少一个有机层。当施加电流时，阳极注入空穴和阴极注入电子到所述有机层中。注入的空穴和电子各自向着带相反电荷的电极迁移。当电子和空穴定域在同一分子上时，形成了“激子”，所述激子是具有激发能态的定域的电子-空穴对。当激子通过光发射机理松驰时，光被发射。在一些情况下，所述激子可以定域在受激准分子或激态复合物上。非辐射机理如热弛豫也可能发生，但一般被认为是不希望的。
最初的OLED采用从发射分子的单线态发光(“荧光”)的发射分子，例如在美国专利4,769,292号中公开的，该专利全部内容通过引用结合到本文中。荧光发射通常在小于10毫微秒的时间范围内发生。
最近，已经证实了具有从三重态发光(“磷光”)的发射材料的OLED。Baldo等人，“Highly Efficient Phosphorescent Emission from Organic ElectroluminescentDevices”，Nature，395卷，151-154，1998(“Baldo-I”)；和Baldo等人，“Very high-efficiency green organic light-emitting devices based onelectrophosphorescence”，Appl.Phys.Lett.，75卷，第3期，4-6(1999)(“Baldo-II”)，它们的全部内容通过引用结合在本文中。磷光被更详细地描述在美国专利7,279,704号5-6栏中，所述内容通过引用结合在本文中。
图1显示了有机发光器件100。所述附图不一定按比例画出。器件100可包括基材110，阳极115，空穴注入层120，空穴传输层125，电子封闭层130，发射层135，空穴封闭层140，电子传输层145，电子注入层150，保护层155，和阴极160。阴极160是具有第一导电层162和第二导电层164的复合阴极。器件100可以通过按照顺序沉积所述层来制造。这些不同层的性能和功能以及实例材料被更详细地描述在US 7,279,704的6-10栏中，所述内容通过引用结合在本文中。
用于这些层中的每个层的更多实例是可获得的。例如，一种柔性和透明的基材-阳极组合被公开在美国专利5,844,363号中，该专利的全部内容通过引用结合在本文中。p-掺杂的空穴传输层的一个例子是按照50:1的摩尔比率掺杂了F4-TCNQ的m-MTDATA，如在美国专利申请出版物2003/0230980中所公开的，该文献的全部内容通过引用结合在本文中。发射和主体材料的实例被公开在Thompson等人的美国专利6,303,238号中，该专利的全部内容通过引用结合在本文中。n-掺杂的电子传输层的一个例子是按照1:1的摩尔比率掺杂了Li的BPhen，如在美国专利申请出版物2003/0230980号中所公开的，该文献的全部内容通过引用结合在本文中。美国专利5,703,436号和5,707,745号(它们的全部内容通过引用结合在本文中)公开了包括复合阴极在内的阴极的例子，所述复合阴极具有金属如Mg:Ag的薄层，在所述金属薄层上具有层叠的透明的、导电的、溅射沉积的ITO层。封闭层的理论和使用更详细地描述在美国专利6,097,147和美国专利申请出版物2003/0230980号中，它们的全部内容通过引用结合在本文中。在美国专利申请出版物2004/0174116中提供了注入层的实例，所述文献的全部内容通过引用结合在本文中。对保护层的描述可以在美国专利申请出版物2004/0174116中找到，它的全部内容通过引用结合在本文中。“增进层”在器件中与上述封闭层占相同的位置,并且可以具有封闭功能或改进器件性能的其它功能。
图2显示了颠倒的OLED 200。该器件包括基材210，阴极215，发射层220，空穴传输层225，和阳极230。器件200可以通过按照顺序沉积所述层来制造。因为最常见的OLED构型具有布置在阳极上的阴极，并且器件200具有布置在阳极230下的阴极215，因此器件200可以被称为“颠倒的”OLED。与讨论器件100时所描述的那些材料类似的材料可用于器件200的相应层中。图2提供了如何从器件100的结构中省略掉一些层的一个实例。
在图1和2中示出的简单层状结构是作为非限制性例子提供的，并且可以理解，本发明的实施方案可以与各种其它结构相结合使用。所述的特定材料和结构是举例性质的，并且其它材料和结构可以被使用。功能化的OLED可以通过以不同的方式组合所述的各种层来实现，或者某些层可以被完全省略，基于设计、性能和成本因素。没有具体描述的其它层也可以被包括。可以使用除了具体描述的那些材料之外的材料。虽然在这里提供的许多实施例将各种层描述为包括单一一种材料，但是可以理解，可以使用材料的组合，如主体和掺杂剂的混合物，或更一般地混合物。还有，这些层可具有各种亚层。在这里给予各种层的名称并不是意图严格限制的。例如，在器件200中，空穴传输层225传输空穴并将空穴注入到发射层220中，因此可以被描述为空穴传输层或空穴注入层。在一个实施方案中，OLED可以被描述为具有设置在阴极和阳极之间的“有机层”。该有机层可以包括单个层，或者可以进一步包括例如讨论图1和2时所述的不同有机材料的多个层。
没有具体描述的结构和材料也可以使用，例如由聚合物材料组成的OLED(PLED)，如公开在美国专利5,247,190(Friend等人)中的PLED，该专利的全部内容通过引用结合在本文中。作为另一个例子，可以使用具有单个有机层的OLED。OLED可以堆叠，例如如在美国专利5,707,745(Forrest等人)中所述，该专利的全部内容通过引用结合在本文中。OLED结构可以背离在图1和2中图示说明的简单层状结构。例如，基材可以包括有角度的反射面以改进外偶联，如在Forrest等人的美国专利6,091,195中所述的台式结构，和/或在Bulovic等人的美国专利5,834,893中描述的坑形结构，所述专利的全部内容通过引用结合在本文中。
除非另作说明，各种实施方案的这些层中的任何一层可以通过任何合适的方法沉积。对于有机层，优选的方法包括热蒸发，墨喷(如在美国专利6,013,982和6,087,196中所述的，所述专利的全部内容通过引用结合在本文中)，有机气相沉积(OVPD)(如在Forrest等人的美国专利6,337,102中所述的，该专利的全部内容通过引用结合在本文中)，和通过有机蒸气喷印(OVJP)的沉积(如在美国专利申请序列号10/233,470中所述的，该专利申请的全部内容通过引用结合在本文中)。其它合适的沉积方法包括旋涂和其它溶液型工艺。溶液型工艺优选在氮或惰性气氛中进行。对于其它层，优选的方法包括热蒸发。优选的图案化方法包括通过掩模的沉积，冷焊(如在美国专利6,294,398和6,468,819中描述的方法，所述专利的全部内容通过引用结合在本文中)，和与某些沉积方法如墨喷和OVJD联合的图案化。其它方法也可以使用。被沉积的材料可以被改性，以使得它们与具体的沉积方法相容。例如，取代基如支化或未支化的并优选含有至少3个碳的烷基和芳基可以用于小分子中，以提高它们经历溶液加工的能力。可以使用具有20个碳或更多个碳的取代基，而3-20个碳是优选的范围。具有不对称结构的材料可以比具有对称结构的那些材料有更好的溶液加工性，因为不对称材料可以有更低的重结晶倾向。树状分子取代基可用来提高小分子经历溶液加工的能力。
根据本发明的实施方案制造的器件可以结合到各种各样的消费产品中，包括平板显示器，计算机显示器，电视，广告牌，内部或外部照明和/或发信号的光源，平视显示器(heads up display)，全透明显示器，柔性显示器，激光打印机，电话，移动电话，个人数字助理(PDA)，膝上型计算机，数字式摄象机，摄像放像机，取景器，微型显示器，车辆，大面积幕墙，戏院或露天运动场屏幕，或标牌。各种控制机构可用来控制根据本发明制造的器件，包括无源矩阵和有源矩阵。许多的器件预计在人感觉舒适的温度范围如18℃到30℃的范围中使用，更优选在室温(20-25℃)使用。
在这里描述的材料和结构可以应用在不同于OLED的器件中。例如，其它光电器件如有机太阳能电池和有机光检测器可以使用所述材料和结构。更一般地，有机器件如有机晶体管可以使用所述材料和结构。
术语卤、卤素、烷基、环烷基、烯基、炔基、芳烷基、杂环基、芳基和杂芳基是本领域已知的,并且被在US 7,279,704的31-32栏中定义，所述定义通过引用结合在本文中。
本发明提供了化合物，所述化合物包含含苯并[9,10]菲的苯并稠合的噻吩。苯并[9,10]菲是具有高三重态能量，但还具有高的π-共轭和相对小的第一单线态和第一三重态能级间能量差的聚芳族烃。这将预示，与具有类似三重态能量的其它芳族化合物(例如联苯)相比，苯并[9,10]菲具有相当容易被利用的HOMO和LUMO能级。使用苯并[9,10]菲和其衍生物作为主体的优点在于，它能够容纳红、绿和甚至蓝色磷光掺杂剂以给出高的效率，而没有能量猝灭。苯并[9,10]菲主体可以被用于提供高效和稳定的PHOLED。参见Kwong andAlleyene,TriphenyleneHosts in Phosphorescent Light Emitting Diodes,2006,60pp,US 2006/0280965 A1。苯并稠合的噻吩可以被用作空穴传输有机介质。另外，苯并噻吩类，即二苯并[b,d]噻吩(在本文中称为“二苯并噻吩”)，苯并[b]噻吩和苯并[c]噻吩的三重态能量是相当高的。苯并稠合的噻吩和苯并[9,10]菲的组合作为PHOLED中的主体可能是有益的。更具体地说，苯并稠合的噻吩通常更倾向于传输空穴而不是传输电子,而苯并[9,10]菲更倾向于传输电子而不是传输空穴。因此，在一个分子中组合这两个结构部分可以提供改进的电荷平衡，这可以改善器件的寿命、效率和低电压性能。所述两个结构部分的不同化学连接可以被用于调节所得到的化合物的性能，以使得该化合物最适合特定的磷光发射体、器件结构和/或制造方法。例如，间亚苯基连接预期导致较高的三重态能量和较高的溶解性，而对亚苯基连接预期导致较低的三重态能量和较低的溶解性。
类似于对苯并稠合的噻吩的描述，苯并稠合的呋喃也通常是具有相当高三重态能量的空穴传输材料。苯并稠合的呋喃的实例包括苯并呋喃和二苯并呋喃。因此，含苯并[9,10]菲和苯并呋喃二者的材料可以被有利地用作PHOLED中的主体或空穴封闭材料。含这两个基团二者的化合物可以提供改善的电子稳定作用，这可以改善器件稳定性和效率，同时具有低电压。通过使用不同的化学连接来连接所述苯并[9,10]菲和所述苯并呋喃，所述含苯并[9,10]菲的苯并呋喃化合物的性能可以根据需要调节。
所述化合物可以用不必是苯并[9,10]菲、苯并稠合的噻吩和苯并稠合的呋喃的基团取代。优选地，用作所述化合物的取代基的任何基团具有足够高的三重态能量以维持具有苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃的益处(即，所述取代基的三重态能量维持苯并稠合的噻吩、苯并稠合的呋喃和苯并[9,10]菲的高三重态能量)。可以用作所述化合物的取代基的这样的基团的实例可以包括选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1或无取代的任何取代基，其中n是1，2，3，4，5，6，7，8，9或10,和其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。本文中描述的所述化合物具有适合用在具有磷光性蓝色发射材料的器件的足够高的三重态能量。
本文中描述的所述化合物的取代基是非稠合的，使得所述取代基不稠合到所述化合物的苯并[9,10]菲、苯并稠合的呋喃或苯并稠合的噻吩结构部分上。所述取代基任选地可以互相稠合(即彼此稠合)。
本文中提供的材料除了提供改进的器件稳定性和效率外，当器件通过气相沉积和溶液加工方法制造时，本文中提供的材料还可以提供改进的器件中膜形成。特别地，提供改进的制造的材料具有中间吡啶环，所述苯并稠合的噻吩和苯并[9,10]菲(或苯并呋喃和苯并[9,10]菲)连接到所述中间吡啶环上。所述改进的膜形成据信是由于所述化合物中极性和非极性环的组合导致的。
含苯并[9,10]菲的苯并稠合的噻吩的实例包括具有式(I)、式(II)和式(III)的结构的化合物:
R1、R2和R3独立地选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基、杂芳基和氢。R1、R2和R3各自可以表示多个取代基。R1、R2和R3中至少一个包括苯并[9,10]菲基团。所述苯并[9,10]菲基团可以直接连接在式(I)、(II)或(III)的结构上，但是在所述苯并[9,10]菲基团和所述式(I)、(II)或(III)的结构之间可以有“间隔基”。
含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃的实例包括具有以下结构的化合物:
X是S或O。优选地，R1、R2和R3是非稠合的取代基，所述取代基独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1、R2和R3各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
具有式(I)的结构的化合物的实例包括:
R1－Rn独立地表示单、二、三或四取代，其选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基和杂芳基，或无取代。
具有式(IV)的结构的化合物的实例包括:
X是S或O。优选地，X是S。R1－Rn独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1－Rn各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
具有式(II)的结构的化合物的实例包括:
R1－Rn独立地表示单、二、三或四取代，其选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基和杂芳基，或无取代。
具有式(V)的结构的化合物的实例包括:
X是S或O。优选地，X是S。R1－Rn独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1－Rn各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
具有式(III)的结构的化合物的实例包括:
R1－Rn独立地表示单、二、三或四取代，其选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基和杂芳基，或无取代。
具有式(VI)的结构的化合物的实例包括:
X是S或O。优选地，X是S。R1－Rn独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1－Rn各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2,和R3中至少一个包括苯并[9,10]菲基团。
上面公开的每种含苯并[9,10]菲的苯并稠合的噻吩都可以有利地用在有机发光器件中。所述化合物特别可用作有机发光器件的发射层中的主体，这样的器件中的增进层材料，或二者。
实验
化合物实施例
实施例1 4-(苯并[9,10]菲-2-基)二苯并噻吩(化合物1S)
1.2-溴代苯并[9,10]菲的合成
上述化合物的合成被描述在US20060280965中。
2.4-(苯并[9,10]菲-2-基)二苯并噻吩的合成
将4.4g(14.6mmol)2-溴代苯并[9,10]菲，4.0g(17.5mmol)4-二苯并噻吩硼酸，0.51g(0.44mmol)四(三苯基膦)合钯和4.0g(43.4mmol)碳酸钾加入到含有溶剂90mL甲苯和10mL水的250mL圆底烧瓶中。将反应混合物用氮气吹扫30分钟，并且然后将其在氮气氛下在搅拌的同时加热回流过夜。冷却反应混合物，并且将有机萃取物通过柱层析和使用甲苯的重结晶纯化。得到5.1g(86％)白色固体产物，该产物通过1H NMR证实。
实施例2 4-(3-(苯并[9,10]菲-2-基)苯基)二苯并噻吩(化合物2S)
1.三氟甲磺酸3-(2-苯并[9,10]菲)苯基酯的合成
上述化合物的合成被描述在临时申请序列号60/963,944中。
2.4-(3-(苯并[9,10]菲-2-基)苯基)二苯并噻吩的合成
将4.52g(10.0mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，3.0g(13.0mmol)4-二苯并噻吩硼酸，0.46g(0.5mmol)Pd2(dba)3，0.82g(2.0mmol)2-二环己基膦酰基-2’,6’-二甲氧基联苯，12.7g(60.0mmol)K3PO4以及150mL甲苯和15mL水加入到一个250mL圆底烧瓶中。将反应混合物在氮气氛下加热回流过夜。冷却反应混合物，并且将有机萃取物通过柱层析和重结晶纯化。得到4.3g(88％)白色固体产物，该产物通过1H NMR证实。
实施例3 2,8-二(苯并[9,10]菲-2-基)二苯并噻吩(化合物5S)
1.4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷的合成
该化合物的合成被描述在US2006/0280965中。
1.2,8-二(苯并[9,10]菲-2-基)二苯并噻吩的合成
将2.25g(6.3mmol)4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷，0.92g(2.7mmol)2,8-二溴代二苯并噻吩，0.12g(0.14mmol)Pd2(dba)3，0.22g(0.53mmol)2-二环己基膦酰基-2′，6′-二甲氧基联苯，3.4g(16.0mmol)K3PO4，100mL甲苯和10mL水加入到一个250mL的圆底烧瓶中。将反应混合物用氮气吹扫20分钟，然后在搅拌下加热回流过夜。将反应混合物冷却和过滤。将白色固体用甲醇洗涤3次(3x100mL)和用二氯甲烷洗涤(2x100mL)。得到1.6g固体产物(94％收率)，该产物通过用甲苯重结晶和升华进一步纯化。所述产物由固体探针MS证实。
实施例4化合物20S
1.2-溴代二苯并噻吩的合成
将15g(79.9mmol)二苯并噻吩溶解在1.5升氯仿中。向该溶液中滴加12.76g(79.9mmol)溴。将反应混合物在室温下剧烈搅拌2天，然后用亚硫酸钠水溶液处理。将有机相蒸发，给出白色固体，其具有48％未反应的二苯并噻吩，50％2-溴代二苯并噻吩和约小于2％2,8-二溴代二苯并噻吩，基于GC-MS和HPLC结果。将该混合物用乙酸乙酯反复重结晶，得到纯的2-溴代二苯并噻吩。
2.硼酯产物的合成
将8g(17.5mmol)三氟甲磺酸3-(2-苯并[9,10]菲)苯基酯，9.1g(35.2mmol)双(频哪醇根)二硼(bis(pinacolato)diboron)，290mg(0.35mmol)Pd(dffp)2Cl2，5.2g(52.5mmol)KOAc和150mL无水二噁烷加入到一个250mL的三口烧瓶中。将反应混合物在氮气氛下加热至90℃维持20小时。在柱层析后得到7.0g白色固体，所述柱层析使用在己烷中的30％乙酸乙酯作为洗脱剂。产物由1H NMR证实。
3.化合物20S的合成
将2g(7.1mmol)2-溴代二苯并噻吩，4.0g(9.3mmol)步骤2中的硼酯产物，325mg(0.355mmol)Pd2(dba)3，582g(1.4mmol)S-phose，9g(42mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将反应混合物在氮气氛下加热回流过夜。将反应混合物用二氯甲烷萃取，并且有机萃取物通过硅胶柱层析和重结晶纯化。得到约2.9g(85％)白色固体产物，该产物通过1H NMR证实。
实施例5化合物10S
1.4,4’-二甲氧基邻三联苯的合成
制备1,2-二溴代苯(50g，212mmol)，4-甲氧基苯基硼酸(78g，513mmol)，三苯基膦(11.12g，42.2mmol)，碳酸钾(73.25g，530mmol)，二甲氧基乙烷(290mL)和水(290mL)的混合物。将氮气直接鼓泡到所述混合物中20分钟。添加乙酸钯(4.76g，21.2mmol)，并且将所述混合物在氮气氛下加热回流过夜。冷却所述反应混合物，并且添加水和二氯甲烷。分离各层，并且水层用二氯甲烷萃取。合并的有机层通过塞力特硅藻土过滤，并且用盐水洗涤，用硫酸镁干燥，过滤，蒸发，得到黑色油状物。将所述粗材料通过柱层析纯化，使用在己烷中的0梯度变化至100％的二氯甲烷洗脱剂洗脱。将主要的级分通过使用Kugelrohr在200－220℃进行的蒸馏纯化。得到49g(80％)纯净的产物。
2.2,11-二甲氧基苯并[9,10]菲的合成
将12.4g(42.7mmol)4,4’-二甲氧基-邻三联苯和16g(63.0mmol)碘屑放置在一个250mL的反应容器中。添加200mL甲苯，接着添加30mL环氧丙烷。向所述光反应器提供一个通过循环冷却剂冷却的冷凝器。使用400W中压汞灯作为光源。将所述反应容器放在通风橱中。打开所述灯，并且设定冷却剂的温度使得离开所述反应器的水维持在20℃和25℃之间(通过连接到出口物流的热电偶监测)。使所述反应持续18小时。过滤出固体并用己烷洗涤，仅回收2.2g材料。将滤液用甲苯稀释并用硫酸钠溶液洗涤。水层用甲苯反萃取，并且有机层用硫酸镁干燥，过滤，和蒸发。将材料溶解在甲苯中，并添加亚硫酸钠溶液和搅拌。分离各层，水层用甲苯萃取，并且合并的有机层用硫酸镁干燥，过滤，和蒸发。残余物通过柱层析纯化，使用0-100％乙酸乙酯/己烷洗脱。得到8.8g材料(72％)。
3.苯并[9,10]菲-2,11-二酚的合成
将2,11-二甲氧基苯并[9,10]菲(8.8g，30.5mmol)和吡啶盐酸盐(31.73g，274.6mmol)的混合物加热到220℃，维持2小时。冷却所述混合物并添加水。过滤出产生的固体物，用水洗涤，和在高真空下干燥。得到7.45g(94％)期望的产物。
4.苯并[9,10]菲-2,11-二基双(三氟甲磺酸酯)的合成
将苯并[9,10]菲-2,11-二酚(7.45g，28.62mmol)加到100mL二氯甲烷和13mL吡啶中，并且将所述溶液在冰盐浴中冷却。在氮气氛下向所述溶液中滴加三氟甲磺酸酐(19mL，114.49mmol)在70mL二氯甲烷中的溶液。允许所述反应进行2小时，并且通过添加甲醇和水来猝灭该反应，接着用二氯甲烷稀释。过滤出棕褐色固体物，并用二氯甲烷和水洗涤。分离在滤液中的各层，并且水层用二氯甲烷萃取。将有机萃取液用硫酸镁干燥，过滤，和蒸发，得到棕色固体物。所述棕色固体物通过柱层析纯化，用0－100％二氯甲烷/己烷洗脱，然后在170℃升华，和然后从300mL沸腾甲苯中重结晶两次。得到11.4g产物(76％)。
5.化合物10S的合成
制备苯并[9,10]菲-2,11-二基双(三氟甲磺酸酯)(1.5g，2.9mmol)，二苯并噻吩-4-硼酸(2.6g，11.4mmol)，氟化钾(1.1g，19mmol)和THF 50mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加乙酸钾(13mg，0.06mmol)和三环己基膦(19mg，0.07mmol),并且然后再将氮气鼓泡到所述混合物中30分钟。将所述混合物在50℃加热过夜。然后将反应冷却到室温。通过过滤收集沉淀物。将白色固体物放在一个索格利特萃取器中，并且通过回流THF过夜来洗涤。收集在所述萃取器中的固体物，给出0.9克白色固体(收率53％)。
实施例6化合物9S
1.2-(3'-甲氧基联苯-3-基)苯并[9,10]菲的合成
将12.9g(28.5mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，6.5g(42.8mmol)3-甲氧基苯基硼酸，0.47g(1.1mmol)2-二环己基膦酰基-2’,6’-二甲氧基联苯(SPhos)和18.2g(85.5mmol)磷酸三钾(K3PO4)称量到一个圆底烧瓶中。向所述烧瓶中添加150mL甲苯和80mL水作为溶剂。用氮气吹扫所述溶液，并且添加0.26g(0.28mmol)三(二亚苄基丙酮)二钯(0)[Pd2(dba)3]。将所述溶液加热至回流，维持12小时。在冷却后，分离有机层并用硫酸镁干燥。所述产物通过使用己烷/二氯甲烷作为洗脱剂(1/0梯度变化至3/2)的柱层析容易地分离。通过旋转蒸发除去溶剂，得到11.7g(28mmol)产物2-(3'-甲氧基联苯-3-基)苯并[9,10]菲。
2.3'-(苯并[9,10]菲-2-基)联苯-3-酚的合成
在一个圆底烧瓶中，在氮气氛下，将11.5g(28mmol)2-(3'-甲氧基联苯-3-基)苯并[9,10]菲和21.1g(183mmol)吡啶盐酸盐加热到204℃。在冷却后，添加水并用二氯甲烷萃取。合并的有机部分用另外的水洗涤，并且通过旋转蒸发除去溶剂。将固体物干填充在塞力特硅藻土上，并且通过柱层析纯化所述产物，使用己烷:二氯甲烷(1:4)作为洗脱剂。通过旋转蒸发除去溶剂，得到8.6g(22mmol)产物3'-(苯并[9,10]菲-2-基)联苯-3-酚。
3.三氟甲磺酸3'-(苯并[9,10]菲-2-基)联苯-3-基酯的合成
在氮气氛下，将8.6g(22mmol)3'-(苯并[9,10]菲-2-基)联苯-3-酚添加到含3.4g(43.4mmol)无水吡啶和450mL无水二氯甲烷的烧瓶中。将所述溶液在冰浴中冷却，并通过注射器缓慢添加12.2g(43.4mmol)三氟甲磺酸酐(Tf2O)。将所述溶液温热至室温并搅拌过夜。将所述溶液用水洗涤，用硫酸镁干燥，并且通过旋转蒸发除去溶剂。产物三氟甲磺酸3'-(苯并[9,10]菲-2-基)联苯-3-基酯通过柱层析纯化，使用己烷/二氯甲烷作为洗脱剂(1/0梯度变化至1/1)，得到10.7g(20.2mmol)。
4.化合物9S的合成
将5.5g(10.4mmol)上述步骤3的产物，3.0g(13.5mmol)4-硼酸二苯并噻吩，458mg(0.5mmol)Pd2(dba)3，820mg(2mmol)S-phose，12.7g(60mmol)磷酸钾和150mL甲苯加入到一个250烧瓶中。将反应混合物在氮气氛下加热回流过夜。然后将其冷却和后处理。在硅胶柱层析(使用在己烷中的20％二氯甲烷作为洗脱剂)和然后用甲醇洗涤后得到约5g白色产物。产物由1H NMR证实。
实施例7化合物19S
1.3,3’-二甲氧基-邻三联苯的合成
在一个装有搅拌棒、回流冷凝器和氮气入口的2000mL圆底烧瓶中，将1,2-二溴代苯(50.0g，0.212mol)，3-甲氧基苯基硼酸(77.3g，0.509mol)，乙酸钯(1.2g，5.33mmol)，三苯基膦(21.4mmol)，碳酸钠(78.9g，0.744mol)与二甲氧基乙烷(430mL)和水(290mL)合并，并且将它们加热回流4天。添加乙酸乙酯(500mL)，并且分离有机层，将其用硫酸镁干燥和蒸发至干，得到61.3g(99.7％)3,3’-二甲氧基-邻三联苯白色固体。
2.2,9-二甲氧基苯并[9,10]菲的合成
在一个装有氮气入口和搅拌棒的2000mL圆底烧瓶中，将3,3’-二甲氧基-邻三联苯(61.3g，0.211mol)溶解在无水二氯甲烷(1000mL)中。然后添加氯化铁(III)(68.6g，0.423mol),并且将所述混合物搅拌过夜。在第二天早晨，添加另外的2当量氯化铁(III),并且在1小时内反应完全。向所述混合物中添加甲醇和水，并且分离有机层，用硫酸镁干燥和蒸发至干。粗产物通过硅胶柱层析纯化，使用60/40二氯甲烷/己烷作为洗脱剂，给出50.7g浅黄色固体。将该固体从700mL乙腈中重结晶，得到49.1g 2,9-二甲氧基苯并[9,10]菲。
3.2,9-二羟基苯并[9,10]菲的合成
将2,9-二甲氧基苯并[9,10]菲(49.1g，0.170mol)和吡啶盐酸盐(200g，1.70mol)放在一个装有搅拌棒、回流冷凝器和氮气入口的500mL圆底烧瓶中，并在220℃加热90分钟。冷却该溶液，并且添加水，导致形成白色沉淀物。通过真空过滤收集该白色沉淀物，用水洗涤和真空干燥，得到43.7g(96％)2,9-二羟基苯并[9,10]菲。
4.苯并[9,10]菲-2,7-二基双(三氟甲磺酸酯)的合成
向在装有搅拌棒和氮气入口的1000mL圆底烧瓶中的2,9-二羟基苯并[9,10]菲(17.5g，65mmol)和吡啶(300mL)的冷溶液(0℃)中滴加三氟甲磺酸酐(38.7g，137mmol)。将反应混合物在室温搅拌过夜。在蒸发掉吡啶后，将得到的固体与甲醇(500mL)在一起搅拌，并且通过真空过滤收集，给出32g白色粉末。将该白色粉末从500mL庚烷/二氯乙烷的30/70混合物中重结晶，得到28.3g(82％)2,9-双(三氟甲磺酰基)苯并[9,10]菲。
5.化合物19S的合成
制备苯并[9,10]菲-2,7-二基双(三氟甲磺酸酯)(2g，3.8mmol)，二苯并噻吩-4-硼酸(3.5g，15mmol)，氟化钾(1.5g，25mmol)和THF 100mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加乙酸钾(17mg，0.08mmol)和三环己基膦(26mg，0.09mmol)，并且然后再将氮气鼓泡到所述混合物中30分钟。将该混合物在室温搅拌2天。然后将反应冷却到室温。通过过滤收集沉淀物。添加乙酸钾(17mg，0.08mmol)和三环己基膦(26mg，0.09mmol)，然后再将氮气鼓泡到所述混合物中15分钟。将该混合物在室温再搅拌2天。将灰色固体物放在一个索格利特萃取器中，并且通过回流THF过夜来洗涤。收集在所述萃取器中的固体物，给出2.1克白色固体(收率92％)。
实施例8化合物22S
步骤1
制备2,6-二氯吡啶(13g，88mmol)，二苯并噻吩-4-硼酸(5g，22mmol)，磷酸三钾(28g，132mmol)，甲苯300mL和水30mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加三(二亚苄基丙酮)(0.54g，1.3mmol),并且然后将氮气再鼓泡到该混合物中20分钟。将所述混合物在室温下搅拌2天。然后收集有机层，并且水层用二氯甲烷萃取。合并的有机层用硫酸镁干燥和浓缩。粗产物通过硅胶快速层析纯化，使用最高达10％乙酸乙酯/己烷洗脱，给出5克黄色固体物。将该黄色固体物进一步从二氯乙烷/庚烷中重结晶，得到2.5克白色固体物(39％)。
2.化合物22S的合成
制备4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷(2.2g，6.1mmol)，2-氯-6-(二苯并噻吩-4-基)吡啶(1.5g，5.1mmol)，磷酸三钾(3.3g，15.3mmol)，甲苯150mL和水15mL的混合物。将氮气直接鼓泡到所述混合物中40分钟。然后添加三(二亚苄基丙酮)二钯(56mg，0.06mmol)和双(环己基)-2-联苯基膦(100mg，0.24mmol),并且然后再将氮气鼓泡到所述混合物中17分钟。将反应混合物在氮气氛下回流过夜。通过过滤收集沉淀物，并且用甲苯、二氯甲烷和甲醇洗涤。然后，将所述产物溶解在250mL沸腾二甲苯中，过滤通过一个小的硫酸镁柱。将滤液加热至回流以溶解所有的固体，并且允许其慢慢冷却下来。得到重结晶过的产物，为2.3克白色固体(93％)。
实施例9化合物21S
1.2-氯-6-(3-甲氧基苯基)吡啶的合成
制备间甲氧基苯基硼酸(10g，65.8mmol)，2,6-二氯吡啶(9.7g，65.8mmol)，碳酸钾(27.3g，197.4mmol)，三苯基膦(2.07g，7.9mmol)，二甲氧基乙烷250mL和水80mL的混合物。将氮气直接鼓泡到所述混合物中20分钟。然后添加乙酸钯(0.44g，2.0mmol)。将氮气再鼓泡到所述混合物中10分钟。将所述混合物在氮气氛下加热回流过夜。将反应混合物冷却到室温。分离有机层，并且水层用二氯甲烷萃取。合并的有机层用硫酸镁干燥，过滤和蒸发。将混合物通过硅胶柱纯化，使用最高达10％乙酸乙酯/己烷洗脱，得到6.5g无色油状物(45％)。
2.2-(二苯并[b,d]噻吩-4-基)-6-(3-甲氧基苯基)吡啶的合成
制备2-氯-6-(3-甲氧基苯基)吡啶(3.5g，16mmol)，二苯并噻吩-4-硼酸(4g，17.5mmol)，磷酸钾(10.2g，48mmol)，二甲氧基乙烷500mL和水50mL的混合物。将氮气直接鼓泡到所述混合物中15分钟。然后添加三(二亚苄基丙酮)二钯(147mg，0.16mmol)和2-二环己基膦酰基-2',6'-二甲氧基联苯(263mg，0.64mmol)，并且然后再将氮气鼓泡到所述混合物中15分钟。将反应混合物在氮气氛下加热回流过夜。在第二天，将反应混合物冷却到室温。分离有机层，并且水层用二氯甲烷萃取。合并的有机层用硫酸镁干燥，过滤和蒸发。将混合物通过硅胶柱纯化，使用最高达10％乙酸乙酯/己烷洗脱，得到3.8g黄色固体(65％)。
3.3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯酚的合成
将2-(二苯并[b,d]噻吩-4-基)-6-(3-甲氧基苯基)吡啶(3.8g，10.3mmol)溶解在120mL二氯甲烷中。将该溶液在氮气氛下冷却到0℃。在0℃向该溶液中慢慢添加BBr3(22.8mL，1M的己烷溶液)，然后将该溶液缓慢升温至室温。将该混合物在室温下搅拌过夜。观察到形成了棕色固体物。通过缓慢添加100mL水猝灭该反应。通过旋转蒸发除去二氯甲烷。然后将该混合物回流3小时。添加饱和碳酸氢钠溶液以中和该混合物，然后将该混合物用二氯甲烷和乙酸乙酯萃取。合并的有机层用硫酸镁干燥，过滤和在减压下浓缩，得到4克玻璃状茶褐色固体。该产物直接用于后面的步骤而不用进一步纯化。
4.三氟甲磺酸3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯基酯的合成
将3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯酚(4g，11.3mmol)悬浮在100mL吡啶中，用丙酮/冰浴冷却至-10℃。在氮气氛下缓慢添加三氟甲磺酸酐(2.29mL，13.6mmol)。将该混合物在0℃搅拌2小时，然后倾倒入200mL饱和碳酸氢钠溶液中。将该混合物用乙酸乙酯萃取。合并的有机层用硫酸镁干燥，过滤和蒸发。混合物通过硅胶柱纯化两次，使用最高达15％乙酸乙酯/己烷洗脱。然后，通过添加己烷使产物从其二氯甲烷溶液中沉淀出来，得到1.8克白色固体(最后两步的总收率为36％)。
5.化合物21S的合成
制备三氟甲磺酸3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯基酯(1.65g，3.4mmol)，4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷(1.32g，3.7mmol)，磷酸钾(2.16g，10.2mmol)，甲苯100mL和水10mL的混合物。将氮气直接鼓泡到所述混合物中25分钟。然后添加三(二亚苄基丙酮)二钯(31mg，0.034mmol)和2-二环己基膦酰基-2',6'-二甲氧基联苯(55mg，0.14mmol)，并且然后再将氮气鼓泡到所述混合物中15分钟。将反应混合物在氮气氛下加热回流8小时。在第二天，将反应混合物冷却到室温。通过过滤收集残余物，用甲苯、二氯甲烷和甲醇充分洗涤，得到1.8克灰色固体。在用于器件制造前，将该灰色固体在260℃升华两次。
实施例10化合物4S
1.2,11-双(3-甲氧基苯基)苯并[9,10]菲的合成
制备苯并[9,10]菲-2,11-二基双(三氟甲磺酸酯)(2g，3.8mmol)，3-甲氧基苯基硼酸(2.3g，15mmol)，磷酸三钾(4.8g，23mmol)，甲苯100mL和水10mL的混合物。将氮气直接鼓泡到所述混合物中30分钟。然后添加三(二亚苄基丙酮)二钯(70mg，0.076mmol)和双(环己基)-2-联苯基膦(125mg，0.30mmol)，并且然后再将氮气鼓泡到所述混合物中15分钟。将反应在氮气氛下回流3小时。在冷却到室温后，收集反应混合物的有机层，用硫酸镁干燥，和在减压下浓缩。粗产物通过硅胶快速层析纯化，给出1.6g白色固体(收率95％)。
2.3,3'-(苯并[9,10]菲-2,11-二基)二苯酚的合成
将2,11-双(3-甲氧基苯基)苯并[9,10]菲(1.6g，3.7mmol)和吡啶盐酸盐(4.3g，37mmol)的混合物在氮气氛下在220℃加热2.5小时。将反应物冷却到室温，并且用水洗涤。通过过滤收集到1.6g棕色残余物，将其在真空下干燥，并且不用进一步纯化用于下一步骤。
3.3,3'-(苯并[9,10]菲-2,11-二基)双(3,1-亚苯基)双(三氟甲磺酸酯)的合成
将3,3'-(苯并[9,10]菲-2,11-二基)二苯酚(1.6g，3.9mmol)悬浮在50mL二氯甲烷和5mL吡啶的混合物中。将该混合物用冰/水浴冷却到0℃。将三氟甲磺酸酐(1.44mL，8.5mmol)溶解在30mL二氯甲烷中，并在氮气氛下在0℃缓慢添加到所述反应混合物中。然后将反应在室温在氮气氛下搅拌过夜。向反应中添加20mL甲醇。通过旋转蒸发浓缩所述混合物。将残余物悬浮在水中，然后通过过滤收集。在用水洗涤后，将残余物在真空下干燥。粗产物通过硅胶快速层析纯化，使用在己烷中的最高达30％二氯甲烷洗脱，给出白色固体1.6克(最后两步的总收率:65％)。
4.化合物4S的合成
制备3,3'-(苯并[9,10]菲-2,11-二基)双(3,1-亚苯基)双(三氟甲磺酸酯)(1.6g，2.4mmol)，二苯并噻吩-4-硼酸(2.7g，12mmol)，磷酸三钾(3.4mmol，16mmol)，甲苯100mL和水50mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加三(二亚苄基丙酮)二钯(44mg，0.048mmol)和双(环己基)-2-联苯基膦(78mg，0.19mmol)，并且然后再将氮气鼓泡到所述混合物中30分钟。将反应回流过夜。在将反应冷却到室温后，通过过滤收集残余物，并且用甲醇和二氯甲烷洗涤，给出最终产物。
实施例11化合物23S
1.4-苯基二苯并噻吩的合成
将10g(41.6mmol)4-二苯并噻吩硼酸，6.25g(39.6mmol)溴代苯，366mg(0.39mmol)Pd2(dba)3，656mg(1.6mmol)S-phose，25.4g(120mmol)K3PO4，180mL甲苯和20mL水加入到一个500mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物通过硅胶柱层析纯化，使用纯己烷作为洗脱剂。得到约8.5g(83％)白色固体产物，其由MS证实。
2.4-苯基二苯并噻吩-6-硼酸的合成
在一个250mL三口烧瓶中，将3.5g(13.4mmol)4-苯基二苯并噻吩溶解在约30mL无水THF中，并将其冷却到-78℃。向该混合物中添加17mL(27mmol)1.6M的BuLi在己烷中的溶液，并且搅拌30分钟。移开冷却浴，并且将反应保持搅拌过夜。将反应混合物再冷却到-78℃，添加4.5mL(40mmol)硼酸三甲酯，并在室温下搅拌4小时。添加约1001M HCl，并保持搅拌1小时。将混合物用乙酸乙酯萃取，并且合并有机萃取物。蒸干溶剂。将固体物添加到约100mL 20％乙酸乙酯/己烷中，并搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤数次。得到约2.5g白色固体产物，该产物由1H NMR证实。
3.化合物23S的合成
将2.4g(7.89mmol)上述硼酸，3.3g(7.2mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，67mg(0.08mmol)Pd2(dba)3，120mg(0.3mmol)S-phose，4.6g(21.7mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流6.5小时。用分液漏斗分离反应混合物，有机相通过使用在己烷中的20％二氯甲烷作为洗脱剂的硅胶柱层析和从甲苯-己烷混合物中重结晶来纯化。得到约3.8g(94％)白色固体产物，该产物通过1HNMR证实。
实施例12化合物24S
1.2,8-二苯基苯并噻吩的合成
将7.0g(20.4mmol)2,8-二溴代二苯并噻吩，6.4g(51.1mmol)苯基硼酸，187mg(0.2mmol)Pd2(dba)3，335mg(0.8mmol)S-phose，13g(61.2mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流4小时。用分液漏斗分离反应混合物，并且有机相通过硅胶柱层析纯化，使用在己烷中的20％二氯甲烷作为洗脱剂。得到约6.6g(96％)白色固体产物，该产物由GC-MS证实。
2.2,8-二苯基二苯并噻吩-4-硼酸的合成
在一个250mL三口烧瓶中，将3.8g(11.3mmol)2,8-二苯基苯并噻吩溶解在约30mL无水THF中。在-78℃，在氮气氛下，向该混合物中添加约18mL(28.3mmol)1.6M的BuLi在己烷中的溶液。将该混合物温热至室温并保持搅拌18小时。将反应混合物再冷却到-78℃，并且添加3.8mL(34mmol)硼酸三甲酯。在室温下搅拌该混合物4小时，然后添加约60mL 1M HCl，同时搅拌1小时。用乙酸乙酯萃取该混合物，并且合并有机相。将溶剂蒸干。向固体中添加约100mL 20％乙酸乙酯/己烷。搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤3次。得到约2.2g白色固体产物，该产物由1H NMR证实。
3.化合物24S的合成
将2.0g(5.26mmol)2,8-二苯基二苯并噻吩-4-硼酸，2.18g(4.78mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，45mg(0.05mmol)Pd2(dba)3，80mg(0.19mmol)S-phose，3.2g(14mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流过夜。用分液漏斗分离反应混合物，并且有机相通过使用在己烷中的20％二氯甲烷作为洗脱剂的硅胶柱层析和从甲苯和己烷混合物中重结晶来纯化。得到约2.52g(84％)白色固体产物，该产物通过1HNMR证实。
实施例13化合物25S
1. 2,8-二苯基苯并噻吩的合成
将7.0g(20.4mmol)2,8-二溴代二苯并噻吩，6.4g(51.1mmol)苯基硼酸，187mg(0.2mmol)Pd2(dba)3，335mg(0.8mmol)S-phose，13g(61.2mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流4小时。反应混合物用分液漏斗分离，并且有机相通过硅胶柱层析纯化，使用在己烷中的20％二氯甲烷作为洗脱剂。得到约6.6g(96％)白色固体产物，该产物由GC-MS证实。
2. 2,8-二苯基二苯并噻吩-4-硼酸的合成
[UDC，请核实我们给上述中间体指定的名称]
在一个250mL三口烧瓶中，将3.8g(11.3mmol)2,8-二苯基苯并噻吩溶解在约30mL无水THF中。在-78℃，在氮气氛下，向该混合物中添加约18mL(28.3mmol)1.6M的BuLi在己烷中的溶液。将该混合物温热至室温并保持搅拌18小时。将反应混合物再冷却到-78℃，并且添加3.8mL(34mmol)硼酸三甲酯。在室温下搅拌该混合物4小时。然后添加约60mL 1M HCl，同时继续搅拌1小时。用乙酸乙酯萃取该混合物，并且合并有机相。将溶剂蒸干。向固体中添加约100mL 20％乙酸乙酯/己烷。搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤。得到约2.2g白色固体产物，该产物由1H NMR证实。
3. 2,4,8-三苯基苯并噻吩的合成
将5.5g(14.5mmol)2,8-二苯基二苯并噻吩-4-硼酸，2.3g(14.5mmol)溴代苯，135mg(0.15mmol)Pd2(dba)3，238mg(0.58mmol)S-phose，9.2g(43.2mmol)K3PO4，180mL甲苯和20mL水加入到一个500mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物用分液漏斗分离，并且有机相通过硅胶柱层析纯化，使用在己烷中的20％乙酸乙酯作为洗脱剂。得到约5.1g 2,4,8-三苯基苯并噻吩白色固体产物，该产物通过1H NMR证实。
4. 2,4,8-三苯基二苯并噻吩-6-硼酸的合成
在一个250mL三口烧瓶中，将5.0g(12.13mmol)2,4,8-三苯基苯并噻吩溶解在约100mL无水THF中。在-78℃，在氮气氛下，向该混合物中添加约19mL(30.3mmol)1.6M的BuLi在己烷中的溶液。将该混合物温热至室温并保持搅拌18小时。将反应混合物再冷却到-78℃，并且添加3.8mL(34mmol)硼酸三甲酯。在室温下搅拌该混合物4小时，然后添加约100mL1M HCl，同时搅拌1.5小时。用乙酸乙酯萃取该混合物，并且合并有机相。将溶剂蒸干。向固体中添加约150mL 20％乙酸乙酯/己烷。将该混合物搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤3次。得到约4.5g白色固体产物，该产物由1H NMR证实。
5.化合物25S的合成
将3.5g(7.67mmol)2,4,8-三苯基二苯并噻吩-6-硼酸，3.2g(6.98mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，64mg(0.077mmol)Pd2(dba)3，115mg(0.30mmol)S-phose，4.5g(22mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物用分液漏斗分离，并且有机相通过使用25％二氯甲烷/己烷作为洗脱剂的硅胶柱层析和从甲苯和己烷混合物中重结晶来纯化。得到约4.5g(92％)白色固体产物，该产物通过1H NMR证实。
实施例14化合物2O
将3.9g(18.4mmol)二苯并呋喃-4-硼酸，7.0g(15.4mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，141mg(0.154mmol)Pd2(dba)3，252mg(0.46mmol)S-phose，9.8g(46mmol)K3PO4，180mL甲苯和20mL水加入到一个500mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物用分液漏斗分离，并且有机相通过硅胶柱层析纯化，使用20％二氯甲烷/己烷作为洗脱剂。得到约6.2g(87％)白色固体产物，该产物通过1H NMR证实。
器件实施例
所有实施例器件通过高真空(<10－7托)热蒸发来制备。阳极电极是约800或1200埃的氧化铟锡(ITO)。阴极由10埃的LiF和后面的1,000埃的Al组成。所有器件在制造之后马上在氮气手套箱(<1ppm的H2O和O2)中用玻璃盖子盖上并用环氧树脂密封，并且在包装内引入吸湿气剂。
表1和2中的器件实施例1-30的有机堆叠物由如下物质组成：从ITO表面开始依次地，作为空穴注入层(HIL)的的化合物A，作为空穴传输层(HTL)的的4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)，作为发射层(EML)的的用10或15wt％Ir磷光性化合物掺杂的本发明化合物，作为ETL2的50或的HPT或本发明化合物，和作为ETL1的400或的Alq3(三(8-羟基喹啉)铝)。
对比例1和2类似于所述器件实施例制造，但是使用CBP作为主体。
器件结构和数据总结在表1－5中。表1显示了器件结构，表2显示了这些器件的相应的测量结果，而表3－5各自显示了器件结构和测量的实验结果。在这里使用的化合物A、化合物B、NPD和HPT具有如下结构:
表1
表2
从器件实施例1-30可以看到，化合物1S、2S、20S、9S、23S、24S和2O作为绿色磷光OLED中的主体给出了高的器件效率(在1000cd/m2下LE>40cd/A)，表明苯并[9,10]菲和苯并噻吩的组合(无论直接连接或由间亚苯基连接)具有对于有效的绿色场致磷光来说足够高的三重态能量。
可以注意到结合有作为主体的化合物1S、2S、21S、23S和2O的器件的高稳定性。器件实施例1和对比例2仅主体不同。器件实施例1使用化合物1作为主体，而对比例2使用通常使用的主体CBP。寿命T80％(定义为在室温下在40mA/cm2的恒定电流密度下初始发光度L0衰减到其值的80％时所要求的时间)分别为270小时和105小时，而器件实施例1具有略高的L0。这相当于几乎3倍的器件稳定性改进。类似地，使用化合物2S作为主体的器件实施例5比对比例2稳定至少1.5倍。使用化合物2S作为主体的器件实施例9比使用CBP作为主体的对比例1稳定至少2倍。还可以注意到，所述化合物可以很好地用作增进层材料(ETL2)。器件实施例10和器件实施例9都含有化合物2S作为主体，但是分别含有化合物2和HPT作为增进层。器件实施例10和器件实施例9分别具有450和380小时的T0.8，表明了化合物2S作为增进层材料的好的性能。器件实施例21具有620小时的T0.8，该数值显著高于使用CBP的对比例1或2器件的寿命。
所述数据表明，含苯并[9,10]菲的苯并噻吩类，特别是含苯并[9,10]菲的二苯并噻吩类，是优异的磷光OLED的主体和增进层材料，与通常使用的作为主体的CBP相比，它们提供了至少相当的效率和多倍的稳定性改进。含苯并[9,10]菲的苯并噻吩类的更共轭的变体，例如通过对亚苯基(例如4,4'-联苯基)连接的苯并[9,10]菲和苯并噻吩单元，可能非常适合较低能量(黄－红)的磷光OLED。
表3显示了某些器件的器件结构和测量的实验结果，所述器件具有在第一有机层和第二有机层间具有界面的发射层，其中在两个层中主体和掺杂剂(即非发射材料)是相同的材料，并且在两个层中磷光材料是相同的材料，但是浓度不同。表3中的所有器件具有的化合物A组成的空穴注入层，的不同材料(取决于具体的器件)组成的增进层(ETL2)，的电子传输层(ETL1),和LiF/Al阴极。所述发射层包括第一有机层和第二有机层，在所述两层间有界面，其中第一有机层是浓度为70wt％的非发射材料(表3中的“主体”)和浓度为30wt％的磷光材料(表3中的“掺杂剂”)组成的的层,并且第二有机层是相同但浓度为90wt％的非发射材料(表3中的“主体”)和相同但浓度为10wt％的磷光材料(表3中的“掺杂剂”)组成的的层。每个器件的具体的主体和掺杂剂在表3中指明。因此，表3的器件的通用器件结构为:ITO/化合物/主体(70wt％):掺杂剂(30wt％)/主体(90wt％):掺杂剂(10wt％)/ETL2/Alq3 /LiF/Al。
表3
使用化合物2S作为主体和化合物2S或HPT作为增进层材料的表3中器件显示了高的效率(在1000cd/m2下>46cd/A)。甚至更值得注意的是1000小时(器件实施例A、B和D)或甚至2000小时(器件实施例C)的LT80％的稳定性，这样的稳定性使得这些器件属于迄今为止最长寿命的绿色磷光OLED。
含有苯并[9,10]菲-苯并噻吩杂化体的器件的好的性能和高的稳定性据信是苯并[9,10]菲和苯并噻吩电荷传输单元所提供的好的电荷平衡以及由于苯并噻吩和苯并[9,10]菲单元所提供的π-共轭导致的分子氧化/还原态的稳定化的结果。
表4和表5显示了一些器件的器件结构和测量的实验结果，所述器件具有含有连接到中心吡啶的苯并[9,10]菲和苯并稠合的噻吩的发射层。
表4中所有的器件具有的由化合物A组成的空穴注入层，的由NPD组成的空穴传输层，的含有化合物21S作为主体和化合物A作为掺杂剂的发射层，具有表4中指明的材料和厚度的封闭层(BL)，具有表4中指明的厚度的、由Alq组成的电子传输层(ETL),和LiF/Al阴极。特别地，BL厚度和ETL厚度的总和为所述发射层是包括主体和掺杂剂的单一层。每个器件中掺杂剂的具体百分比在表4中指明。因此，表4的通用器件结构为:ITO/化合物A/NPD/化合物21S:化合物A x％)/BL/Alq(-BL)/LiF(10)/Al(1000)。
表4
表5中所有的器件具有的由化合物A组成的空穴注入层，的具有表5中指明的材料的空穴传输层，的含有化合物22S作为主体和化合物A作为掺杂剂的发射层，具有表5中指明的材料和厚度的封闭层(BL)，具有减去封闭层(BL)厚度的厚度的电子传输层,和LiF/Al阴极。特别地，所述BL厚度和ETL厚度的总和为所述发射层是包括主体和掺杂剂的单一层。每个器件中具体百分比在表5中指明。因此，表5的通用器件结构为:ITO/化合物A100/HTL/化合物22S:化合物Ax％/BL/Alq(-BL)/LiF(10)/Al(1000)。
表5
*外推的数据
应该理解，本文中描述的各种实施方案仅是为了举例说明，并且不是意图限制本发明的范围。例如，在不脱离本发明的精神的情况下，在这里描述的许多材料和结构可以被其它材料和结构取代。因此，要求保护的本发明可以包括本文中描述的特定实施例和优选实施方案的变例，这一点对于本领域技术人员来说是显而易见的。特别地，所述含苯并[9,10]菲的基团可以连接到苯并噻吩或苯并呋喃的任何位置。应该理解，关于本发明为什么发挥作用的各种理论并不是意图是限制性的。
Claims (20)
1.由式(IV)或式(V)的结构表示的化合物:
其中X是S或O；
其中R2表示单、二、三、四或非取代；
其中R1’表示单、二或非取代；
其中R1、R1’、R2和R3各自是非稠合的取代基，所述取代基独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，其中n是1，2，3，4，5，6，7，8，9或者10，
其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑；和
其中R1、R1’、R2和R3中至少一个包括苯并[9,10]菲基团。
2.权利要求1的化合物，其中所述化合物由式(IV)的结构表示:
3.权利要求2的化合物，其中X是S。
4.权利要求2的化合物，其中X是O。
5.权利要求2的化合物，其中所述化合物由如下结构表示:
其中R4、R5、R8和R9独立地表示单、二、三、四或非取代；
其中R6和R7独立地表示单、二、三或非取代；和
其中R4、R5、R6、R7、R8和R9各自独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1。
6.权利要求5的化合物，其中X是S。
7.权利要求5的化合物，其中X是O。
8.权利要求1的化合物，其中所述化合物由式(V)的结构表示:
9.权利要求8的化合物，其中X是S。
10.权利要求8的化合物，其中X是O。
11.权利要求8的化合物，其中所述化合物选自下组:
其中R1”和R2’各自是非稠合的取代基，所述取代基独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1；
其中R4和R5独立地表示单、二、三、四或非取代；
其中R6和R2’独立地表示单、二、三或非取代；和
其中R4、R5和R6各自独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1。
12.权利要求11的化合物，其中X是S。
13.权利要求11的化合物，其中X是O。
14.权利要求1的化合物，其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲和咔唑。
15.有机发光器件，其包含:
阳极；
阴极；
布置在所述阳极和所述阴极之间的有机层，其中所述有机层包含由式(IV)或式(V)的结构表示的化合物:
其中X是S或O；
其中R2表示单、二、三、四或非取代；
其中R1’表示单、二或非取代；
其中R1、R1’、R2和R3各自是非稠合的取代基，所述取代基独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，其中n是1，2，3，4，5，6，7，8，9或者10，
其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑；和
其中R1、R1’、R2和R3中至少一个包括苯并[9,10]菲基团。
16.权利要求15的器件，其中所述有机层是发射层。
17.权利要求16的器件，其中所述有机层还包含磷光性发射体。
18.权利要求17的器件，其中所述磷光性发射体是铱络合物。
19.权利要求15的器件，其中所述有机层包含化合物2S和铱络合物
20.权利要求15的器件，其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲和咔唑。
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| US96394407P | 2007-08-08 | 2007-08-08 | |
| US60/963,944 | 2007-08-08 | ||
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| US1739107P | 2007-12-28 | 2007-12-28 | |
| US61/017,506 | 2007-12-28 | ||
| US61/017,391 | 2007-12-28 | ||
| CN200880106949.2A CN101827834B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9，10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
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| CN201510646336.XA Active CN105367544B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
| CN201410503620.7A Active CN104311533B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
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