CN104961643A - Cavity transmission material for solar cells - Google Patents
Cavity transmission material for solar cells Download PDFInfo
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- CN104961643A CN104961643A CN201510319089.2A CN201510319089A CN104961643A CN 104961643 A CN104961643 A CN 104961643A CN 201510319089 A CN201510319089 A CN 201510319089A CN 104961643 A CN104961643 A CN 104961643A
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- 239000000463 material Substances 0.000 title claims abstract description 32
- 230000005540 biological transmission Effects 0.000 title abstract description 8
- 125000005264 aryl amine group Chemical group 0.000 claims abstract description 12
- 230000002093 peripheral effect Effects 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 150000002220 fluorenes Chemical class 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 11
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 9
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical class NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 6
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 229940125898 compound 5 Drugs 0.000 claims description 5
- 229940117389 dichlorobenzene Drugs 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000005589 1,3-dimethoxybenzenes Chemical class 0.000 claims description 4
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical class NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- 238000006887 Ullmann reaction Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000011698 potassium fluoride Substances 0.000 claims description 4
- 235000003270 potassium fluoride Nutrition 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 101150003085 Pdcl gene Proteins 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 2
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 0 C*=C(C(C)=*N=N1)C1=C(*)I Chemical compound C*=C(C(C)=*N=N1)C1=C(*)I 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- XDXWNHPWWKGTKO-UHFFFAOYSA-N 207739-72-8 Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 XDXWNHPWWKGTKO-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 239000011244 liquid electrolyte Substances 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- OOYDTEGVMRPGRK-UHFFFAOYSA-N (9-octanoyl-8,10-dioxoheptadecan-9-yl)azanium;chloride Chemical compound [Cl-].CCCCCCCC(=O)C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC OOYDTEGVMRPGRK-UHFFFAOYSA-N 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- ZDUYJCKEORTAQE-UHFFFAOYSA-N 1-iodo-2,4-dimethoxybenzene Chemical class COC1=CC=C(I)C(OC)=C1 ZDUYJCKEORTAQE-UHFFFAOYSA-N 0.000 description 1
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BFQSQUAVMNHOEF-UHFFFAOYSA-N 4-bromo-2,6-difluoroaniline Chemical compound NC1=C(F)C=C(Br)C=C1F BFQSQUAVMNHOEF-UHFFFAOYSA-N 0.000 description 1
- ZTYZIFHALFMOEB-UHFFFAOYSA-N Brc(cc1)cc(Cc2cc(Br)ccc2-c(cc2)c(C3)cc2Br)c1-c(cc1)c3cc1Br Chemical compound Brc(cc1)cc(Cc2cc(Br)ccc2-c(cc2)c(C3)cc2Br)c1-c(cc1)c3cc1Br ZTYZIFHALFMOEB-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C Chemical compound CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- FZXHNTCTFRYPRM-UHFFFAOYSA-N CC1(C)OB(c(cc23)ccc2-c2ccc(B4OC(C)(C)C(C)(C)O4)cc2C32c(cc(B3OC(C)(C)C(C)(C)O3)cc3)c3-c3ccc(B4OC(C)(C)C(C)(C)O4)cc23)OC1(C)C Chemical compound CC1(C)OB(c(cc23)ccc2-c2ccc(B4OC(C)(C)C(C)(C)O4)cc2C32c(cc(B3OC(C)(C)C(C)(C)O3)cc3)c3-c3ccc(B4OC(C)(C)C(C)(C)O4)cc23)OC1(C)C FZXHNTCTFRYPRM-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a novel cavity transmission material, the molecular structure of which is expressed as the specification. The cavity transmission material takes the group with a plurality of substitution sites as the core, adopts a conjugated group with different electron withdrawing abilities as the linkage group, and connects a peripheral arylamine group. An electron withdrawing group is introduced between the core and the peripheral arylamine to regulate the molecular energy level, strengthen electron delocalization and improve molecular charge migration rate, so that the material can be applied as a cavity transmission material to electronic devices.
Description
Technical field
The present invention relates to a class hole mobile material and the application in organic electronic devices thereof.Corresponding electron device can be Organic Light Emitting Diode (OLED), organic memory device, organic field effect tube (OTFT), organic solar batteries (OSC), and based on the solar cell of perovskite material.
Background technology
1977, Heeger, MacDiarmid and Hideki Shirakawa found the polyacetylene of high conductivity, and this discovery not only changes the understanding of people to organic materials, had also started this brand-new field of organic electronics.Development is organic semiconductor field the most rapidly.1986, first was that the organic field effect tube (Organic field-effecttransistor, OFET) of active coating comes out with Polythiophene; The same year, Tang reported first based on phthalein Qing with double layer heterojunction organic solar batteries (the Organic photovoltaic of perylene derivative, OPV), next year reports again first electroluminescent diode based on quinolinol derivative (Organic light-emmiting diode, OLED).The successful development of this three class basic organic electronics device has landmark meaning to organic electronics.Hole mobile material is the important component part of organic electro-optic device.Be widely used in all kinds of devices, very large to the performance impact of corresponding device.
For the quick magnificent solar cell of all solid state uhligite.Organic cavity transmission layer substitutes liquid electrolyte in uhligite solar cell device structure, solves the problem of the volatile leakage of ionogen, strengthens cavity transmission ability, improves device efficiency of conversion and increases device lifetime.2012, Kim etc. were based on CH
3nH
3pbI
3solid-state Jie of perovskite-like sees in sensitization solar battery and uses 2,2 ', 7,7 '-four [N, N-bis-(4-p-methoxy-phenyl) is amino]-9,9 '-spiral shell two fluorenes (2,2,7,7-tetrakis (N, N-p-dimethoxy-phenylamino)-9,9 ' spirobifluorene, spiro-OMeTAD) replace liquid electrolyte, cell photoelectric transformation efficiency reaches 9.7%.At present, 19.3% is brought up to based on spiro-OMeTAD as the electricity conversion of the uhligite solar cell of hole transmission layer.The application prospect of this great potential has attracted numerous science to return home to explore novel organic hole transport material, specific examples is found in document (1) Nam JoongJeon, Jaemin Lee, Jun Hong Noh, Mohammad KhajaNazeeruddin, Michael Gratzel, SangSeok, J.Am.Chem.Soc.2013,135,19087-19090; Document (2) Nam Joong, Hag Geun Lee, Young Chan Kim, JangwonSeo, Jun HongNoh, Jaemin Lee, Sang Seok, J.Am.Chem.Soc.2014,136,7837-7840; Document (3) Zonglong Zhu, Yang Bai, Harrison KaHin Lee, Cheng Mu, Teng Zhang, LixiaZhang, Jiannong Wang, He Yan, Shu Kong So, Shihe Yang, Adv.Funct.Mater.2014,24,7357-7365.
Summary of the invention
The invention provides a class novel hole transport material, wherein with the spiral shell two fluorenes dendritic structure that is representative or two dimensional structure for core, there is the conjugation group of different electron-withdrawing power for link group, connect peripheral arylamine group.Compared with traditional organic hole transport material spiro-OMeTAD, new invention material extends the length of pi-conjugated chain, introduces different electrophilics or electron-donating group simultaneously, with the energy level of controlled material, strengthen electron delocalization, improve material transition rate, thus realize the raising of device performance.
Another object of the present invention is to provide the aryl amine derivatives extremely preparation method of a class with fluorine atom.
In order to reach foregoing invention object, present invention employs following technical scheme:
Novel hole transport material is characterized in that this material has the one in following structural formula:
In said structure general formula, core is have two or more core group replacing site; Link group is the link group with different electron-withdrawing power; Periphery is aryl amine derivatives group; N is the quantity (2≤n≤40) of the arm be linked on core.
Described core has dendritic structure that is non-conjugated or conjugated system, comprises the one in following structural unit:
Wherein A=CH
2or NH or O or S or Se or P or CR
2or NR (R=alkane or aromatic hydrocarbon group); 1≤e≤5.
Above-described link group, should have following structural formula:
Wherein X
1, X
2, X
3... X
n=CH or CF or CCl or CCN or CCF
3or N (n=1,2,3 ... 40)
R＝C
mH
2m+1，m＝1、2、3......10。
Above-described arylamine group, should have following general structure:
Y
1, Y
2, Y
3..., Y
n(n=1,2,3......, 10)=H or C
mh
2m-5(m=1,2,3......, 40), or C
mh
2m-3(m=1,2,3......, 40), or C
mh
2m-1(m=1,2,3......, 40), or C
mh
2m+1(m=1,2,3......, 40) or=C
mh
2m-5o (m=1,2,3......, 40), or C
mh
2m-3o (m=1,2,3......, 40), or C
mh
2m-1o (m=1,2,3......, 40), or C
mh
2m+1o (m=1,2,3......, 40).
The preparation process of above-described link group and arylamine group comprises:
Wherein X
1, X
2, X
3... X
n=CH or CF or CCl or CCN or CCF
3or N (n=1,2,3 ... 40)
Y
1, Y
2, Y
3..., Y
n(n=1,2,3......, 10)=H or C
mh
2m-5(m=1,2,3......, 40), or C
mh
2m-3(m=1,2,3......, 40), or C
mh
2m-1(m=1,2,3......, 40), or C
mh
2m+1(m=1,2,3......, 40) or=C
mh
2m-5o (m=1,2,3......, 40), or C
mh
2m-3o (m=1,2,3......, 40), or C
mh
2m-1o (m=1,2,3......, 40), or C
mh
2m+1o (m=1,2,3......, 40).
Group and core chain are bonded into a series of organic hole transport material thus, and wherein a kind of preparation process of four arm configurations is:
Same method can also obtain two arm configurations:
Wherein X
1, X
2, X
3... X
n=CH or CF or CCl or CCN or CCF
3or N (n=1,2,3 ... 40)
Wherein X
1, X
2, X
3... X
n=CH or CF or CCl or CCN or CCF
3or N (n=1,2,3 ... 40)
Wherein Y
1, Y
2, Y
3..., Y
n(n=1,2,3......, 10)=H or C
mh
2m-5(m=1,2,3......, 40), or C
mh
2m-3(m=1,2,3......, 40), or C
mh
2m-1(m=1,2,3......, 40), or C
mh
2m+1(m=1,2,3......, 40) or=C
mh
2m-5o (m=1,2,3......, 40), or C
mh
2m-3o (m=1,2,3......, 40), or C
mh
2m-1o (m=1,2,3......, 40), or C
mh
2m+1o (m=1,2,3......, 40).
A. at normal temperatures and pressures, by 1,3 dimethoxy benzenes add acetonitrile, add hydrogen peroxide, the hydrochloric acid of appropriate iodine and 34%, react to add deionized water and stirring for some time after four hours and can obtain product 1 and 2.
In above-mentioned steps a, the amount of substance ratio of 1,3 dimethoxy benzenes, hydrogen peroxide, hydrochloric acid, iodine is 2: 1: 1: 1.
B. ullmann reaction, under the protection of rare gas element, in above-mentioned a step, product 1 and para-bromoaniline analog derivative are dissolved in and face dichlorobenzene, take cesium carbonate as alkali, and copper powder is catalyzer, can obtain product 3 after 150 DEG C ~ 180 DEG C reaction for some time.
In above-mentioned reactions steps b, in step a, product 1 is 2.5: 1 ~ 4: 1 with the mol ratio of para-bromoaniline analog derivative, and cesium carbonate will keep excessive simultaneously.
C. ullmann reaction, under the protection of rare gas element, in above-mentioned a reactions steps, product 1 and 2 and para-bromoaniline analog derivative are dissolved in and face dichlorobenzene in right amount, add excessive cesium carbonate and appropriate copper powder, and 150 DEG C ~ 180 DEG C reaction some times obtain product 4.
In above-mentioned reactions steps c, in step a, the mol ratio of product 1 and 2 and para-bromoaniline analog derivative is 2.5: 2.5: 1 ~ 4: 4: 1, and cesium carbonate keeps excessive.
D., under the protection of rare gas element, tetrabromo spiral shell two fluorenes and connection boric acid pinacol ester are dissolved in the tetrahydrofuran (THF) of anhydrous and oxygen-free, 1,1 '-bis-Diphenyl phosphino ferrocene palladium chloride is catalyzer, adds acetic acid first, and 80 DEG C of reactions can obtain compound 5 in 3 days.
In above-mentioned reactions steps d, the mol ratio of connection boric acid pinacol ester and tetrabromo spiral shell two fluorenes is 3: 1 ~ 10: 1.
E. suzuki reaction; the product 3 of above-mentioned reactions steps b and the product 5 of reactions steps d; under the protection of rare gas element; take tetrakis triphenylphosphine palladium as catalyzer; toluene is solvent; add the solution of potassium carbonate of 2 moles often liter and the potassium fluoride solution of 2 moles often liter, 80 DEG C ~ 90 DEG C reaction for some time can obtain product 5 simultaneously.
In above-mentioned reaction, the product 3 of step b is 2.5: 1 ~ 15: 1 with the mol ratio of the product 5 of steps d, ensures that in reaction system, organic phase and inorganic phase volume ratio are 1: 1 ~ 2: 1 simultaneously.
F. suzuki reaction; product 4 in above-mentioned reactions steps c and the product 5 of reactions steps d; under the protection of rare gas element; with four (triphenyl phosphorus) palladium for catalyzer; toluene is solvent; add the solution of potassium carbonate of 2 moles often liter and the potassium fluoride solution of 2 moles often liter, 80 DEG C ~ 90 DEG C reaction for some time can obtain product 6 simultaneously.
In above-mentioned reaction, the product 4 of step c is 2.5: 1 ~ 15: 1 with the mol ratio of the product 5 of steps d, ensures that the volume ratio of organic phase and inorganic phase in reaction system is 1: 1 ~ 2: 1 simultaneously.
Further, in described step a, the reaction times is 4 hours to 8 hours; In described step b, the projection time is 12 hours to 48 hours; In described step c, the reaction times is 24 hours to 72 hours.In described step e, f, the reaction times is 12 hours to 48 hours.
Further, the organophosphor ligand in described step e, f is trimethyl-phosphine, triphenylphosphine, tri-butyl phosphine, and palladium catalyst is Pd (PPh
3)
4, PdCl
2(dppf), Pd (OAc)
2.
Accompanying drawing explanation
Fig. 1, Fig. 2 and Fig. 3 are respectively the synthetic route chart of compound in embodiment 1, embodiment 2 and embodiment 3.
Embodiment
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail, it is pointed out that the following stated embodiment is intended to be convenient to the understanding of the present invention, and any restriction effect is not play to it.
Embodiment 1:
In this enforcement, novel hole transport material is with spiral shell two fluorenes for core, and with fluorine-containing triphenylamine derivative for linking four arms (n=4) structure of group and arylamine group, its structural formula is:
The synthesis of compound 10:
Under normal temperature and pressure, 1, 3 and anisole (1.38g, 10mmol) be dissolved in the acetonitrile of 10ml, add iodine (1.27g respectively again, 5mmol), hydrochloric acid (90 μ l, 37%) hydrogen peroxide (340 μ l, 50%), lucifuge stirs four hours, reaction solution is brown to shoal gradually, treat that color no longer changes the deionized water adding 10ml in backward system, stir one hour, now have a small amount of white precipitate to separate out, with dichloromethane extraction, anhydrous sodium sulfate drying, revolve steaming and can obtain 2.6g compound 1 (2, 4 dimethoxy iodobenzenes), productive rate is 98%.。
The synthesis of compound 11:
With the reaction flask of 25ml, add compound 10 (2.18g, 8.25mmol), 4-bromo-2, 6-difluoroaniline (0.686g, 3.30mmol), cesium carbonate (4.30g, 13.2mmol), copper powder (0.680g, 10.7mmol), solvent is made with to phenyl ether, nitrogen protection, logical water of condensation, 220 DEG C of microwave reactions 40 minutes, after question response system cooling suction filtration, use dichloromethane rinse residual solids, methylene dichloride is pumped with Rotary Evaporators, be separated with silicagel column, sherwood oil and methylene dichloride (1: 2) do eluent, obtain white solid 1.08g, productive rate is 45%.
The synthesis of compound 5:
The there-necked flask getting 250ml adds tetrabromo spiral shell diamyl (1.6g, 2.5mmol), connection boric acid pinacol ester (3.8g, 15mmol), 1, 1 '-bis-Diphenyl phosphino ferrocene palladium chloride (0.40g, 0.50mmol), acetic acid first (2.9g, 30mmol), seal a bottle, logical water of condensation, nitrogen protection, the tetrahydrofuran (THF) of the anhydrous and oxygen-free of 150ml is measured again with syringe, 80 DEG C are reacted three days, go out with shrend afterwards, extraction into ethyl acetate (50ml × 3), the saturated sodium chloride solution of organic phase washes three times, anhydrous sodium sulfate drying, be spin-dried for rear solid with methylene chloride and cross silicagel column, obtain tetraboric acid spiral shell two fluorenes 1.71g, productive rate is 61%.
The synthesis of compound 12:
Get the reaction flask of 25ml, add compound 11 (288mg, 0.60mmol), compound 5 (82mg, 0.10mmol), four (triphenyl phosphorus) palladium (23.5mg, 0.02mmol), phase-transfer catalyst aliquat336 mono-, nitrogen protection, logical water of condensation, toluene (8.0ml) is injected with syringe, 2M solution of potassium carbonate (4ml), 2M Potassium monofluoride (4ml), 90 DEG C are reacted 36 hours, with dichloromethane extraction, saturated common salt water washing, anhydrous sodium sulfate drying, be spin-dried for rear solid and cross silicagel column, eluent is done by sherwood oil and ethyl acetate (1: 1), obtain product 61.2mg, productive rate is 32%.
1H NMR(DMSO，300MHz)δ：8.14(d，4H，J＝8.1Hz)，7.82(d，4H，J＝7.8Hz)，7.13(d，8H，J＝10.3Hz)，6.95(d，4H)，6.65(d，8H，J＝8.5Hz)，6.50(d，8H，J＝2.5Hz)，6.36(dd，8H，J＝2.6Hz、2.7Hz)，3.69(s，22H)，3.48(s，22H)。
Embodiment 2:
In this enforcement, novel hole transport material is with spiral shell two fluorenes for core, and with nitrogenous triphenylamine derivative for linking four arms (n=4) structure of group and arylamine group, its structural formula is:
The synthesis of compound 13:
With the reaction flask of 25ml; add compound 10 (1.02g; 3.86mmol), 2-amino-5-bromo pyrimi piperidine (0.287g; 1.65mmol), cesium carbonate (2.15g; 6.60mmol), copper powder (0.34g, 5.35mmol), make solvent with facing dichlorobenzene; nitrogen protection; logical water of condensation, 180 DEG C are refluxed 48 hours, after question response system cooling suction filtration; use dichloromethane rinse residual solids; pump methylene dichloride with Rotary Evaporators, be separated with silicagel column, methylene dichloride does eluent; obtain product 477mg, productive rate is 65%.
The synthesis of compound 14:
Get the reaction flask of 25ml, add compound 13 (222.5mg, 0.50mmol), compound 5 (82mg, 0.10mmol), four (triphenyl phosphorus) palladium (23.5mg, 0.02mmol), phase-transfer catalyst Aliquat336 mono-, nitrogen protection, logical water of condensation, toluene (8.0ml) is injected with syringe, 2M solution of potassium carbonate (4ml), 2M Potassium monofluoride (4ml), 90 DEG C are reacted 36 hours, with dichloromethane extraction, saturated common salt water washing, anhydrous sodium sulfate drying, be spin-dried for rear solid and cross silicagel column, eluent is done by sherwood oil and ethyl acetate (1: 3), obtain product 71mg, productive rate is 39%.
1H NMR(DMSO，300MHz)δ：8.32(s，8H)，8.09(d，4H，J＝7.9Hz)，7.64(d，4H，J＝8.0Hz)，7.08(d，8H，J＝8.8Hz)，6.80(s，4H)，6.57(s，8H)，6.43(d，8H，J＝9.3Hz，3.70(d，48H，J＝17.8)。
Embodiment 3:
In this enforcement, novel hole transport material with spiral shell two fluorenes for core, with nitrogenous triphenylamine derivative for link group and its structural formula of arylamine group be:
The synthesis of compound 15:
The there-necked flask getting 250ml adds dibromo spiral shell diamyl (1.19g, 2.5mmol), connection boric acid pinacol ester (1.9g, 7.5mmol), 1, 1 '-bis-Diphenyl phosphino ferrocene palladium chloride (0.40g, 0.50mmol), acetic acid first (2.9g, 30mmol), seal a bottle, logical water of condensation, nitrogen protection, the tetrahydrofuran (THF) of the anhydrous and oxygen-free of 150ml is measured again with syringe, 80 DEG C are reacted three days, go out with shrend afterwards, extraction into ethyl acetate (50ml × 3), the saturated sodium chloride solution of organic phase washes three times, anhydrous sodium sulfate drying, be spin-dried for rear solid with methylene chloride and cross silicagel column, obtain hypoboric acid spiral shell two fluorenes 1.31g, productive rate is 61%.
The synthesis of compound 8:
Get the reaction flask of 25ml, add compound 13 (111.5mg, 0.25mmol), compound 5 (82mg, 0.10mmol), four (triphenyl phosphorus) palladium (23.5mg, 0.02mmol), phase-transfer catalyst Aliquat336 mono-, nitrogen protection, logical water of condensation, toluene (8.0ml) is injected with syringe, 2M solution of potassium carbonate (4ml), 2M Potassium monofluoride (4ml), 90 DEG C are reacted 36 hours, with dichloromethane extraction, saturated common salt water washing, anhydrous sodium sulfate drying, be spin-dried for rear solid and cross silicagel column, eluent is done by sherwood oil and ethyl acetate (1: 1), obtain product 59mg, productive rate is 38%.
1H NMR(DMSO，300MHz)δ：8.33(s，4H)，7.9(d，2H，J＝8.3Hz)，7.30(d，2H，J＝8.0Hz)，6.81(d，4H，J＝8.8Hz)，6.65(s，2H)，6.46(s，4H)，6.43(d，4H，J＝9.0Hz，3.83(d，28H，J＝13.8)。
Above-mentioned obtained compound, with spiral shell two fluorenes for kernel, whole molecule is made to have three-D space structure, molecular dispersivity is better, introduce electrophilic fluorine atom and pyrimidine group simultaneously, not only increase pi-conjugated chain length and also can strengthen the mobility that electron delocalization improves material, peripheral oxyalkyl chain of introducing carrys out controlled material energy level.These three materials all can be used as hole transmission layer.
Claims (9)
1. a class novel hole transport material, its feature on molecular structure is that it is made up of three parts, wherein its nuclear structure is connected by link group with peripheral arylamine group, and in above-mentioned hole mobile material, core is the core group having two or more polysubstituted sites; Link group is the group with different electron-withdrawing power.
2. the core described in claim 1 has structure that is non-conjugated or conjugated system, comprises the one in following structural unit:
Wherein A=CH
2or NH or O or S or Se or P or CR
2or NR (R=alkane or aromatic hydrocarbon group) wherein one or more substituting groups; 1≤e≤5.
3. the link group described in claim 1, comprises one or several of following structural formula:
Wherein X
1, X
2, X
3... X
n=CH or CF or CCl or CCN or CCF
3or N (n=1,2,3 ... 40)
R＝C
mH
2m+1.m＝1、2、3……10。
4. the arylamine group described in claim 1, has following general structure:
Y
1, Y
2, Y
3..., Y
n(n=1,2,3 ..., 10)=H or C
mh
2m-5(m=1,2,3 ..., 40), or C
mh
2m-3(m=1,2,3 ..., 40), or C
mh
2m-1(m=1,2,3 ..., 40), or C
mh
2m+1(m=1,2,3 ..., 40) or=C
mh
2m-5o (m=1,2,3 ..., 40), or C
mh
2m-3o (m=1,2,3 ..., 40), or C
mh
2m-1o (m=1,2,3 ..., 40), or C
mh
2m+1o (m=1,2,3 ..., 40).
5. the synthesis of hole mobile material in claim 1, it at least comprises arylamine group and generates corresponding hole mobile material to the combination that precursor and precursor compound and core are produced in the combination linking group.
6. the preparation process linking group and arylamine group comprises:
Wherein X
1, X
2, X
3... X
n=CH or CF or CCl or CCN or CCF
3or N (n=1,2,3 ... 40)
R＝C
mH
2m+1，m＝1、2、3……10。
7. be bonded into organic hole transport material by linking group and arylamine group and core chain, its preparation process is:
A. at normal temperatures and pressures, by 1,3 dimethoxy benzenes add acetonitrile, add hydrogen peroxide, the hydrochloric acid of appropriate iodine and 34%, react to add deionized water and stirring for some time after four hours and can obtain product 1 and 2.
In above-mentioned steps a, the amount of substance ratio of 1,3 dimethoxy benzenes, hydrogen peroxide, hydrochloric acid, iodine is 2: 1: 1: 1.
B. ullmann reaction, under the protection of rare gas element, in above-mentioned a step, product 1 and para-bromoaniline analog derivative are dissolved in and face dichlorobenzene, take cesium carbonate as alkali, and copper powder is catalyzer, can obtain product 3 after 150 DEG C ~ 180 DEG C reaction for some time.
In above-mentioned reactions steps b, in step a, product 1 is 2.5: 1 ~ 4: 1 with the mol ratio of para-bromoaniline analog derivative, and cesium carbonate will keep excessive simultaneously.
C. ullmann reaction, under the protection of rare gas element, in above-mentioned a reactions steps, product 1 and 2 and para-bromoaniline analog derivative are dissolved in and face dichlorobenzene in right amount, add excessive cesium carbonate and appropriate copper powder, and 150 DEG C ~ 180 DEG C reaction some times obtain product 4.
In above-mentioned reactions steps c, in step a, the mol ratio of product 1 and 2 and para-bromoaniline analog derivative is 2.5: 2.5: 1 ~ 4: 4: 1, and cesium carbonate keeps excessive.
D., under the protection of rare gas element, tetrabromo spiral shell two fluorenes and connection boric acid pinacol ester are dissolved in the tetrahydrofuran (THF) of anhydrous and oxygen-free, 1,1 '-bis-Diphenyl phosphino ferrocene palladium chloride is catalyzer, adds acetic acid first, and 80 DEG C of reactions can obtain compound 5 in 3 days.
In above-mentioned reactions steps d, the mol ratio of connection boric acid pinacol ester and tetrabromo spiral shell two fluorenes is 3: 1 ~ 10: 1.
E. suzuki reaction; the product 3 of above-mentioned reactions steps b and the product 5 of reactions steps d; under the protection of rare gas element; take tetrakis triphenylphosphine palladium as catalyzer; toluene is solvent; add the solution of potassium carbonate of 2 moles often liter and the potassium fluoride solution of 2 moles often liter, 80 DEG C ~ 90 DEG C reaction for some time can obtain product 5 simultaneously.
In above-mentioned reaction, the product 3 of step b is 2.5: 1 ~ 15: 1 with the mol ratio of the product 5 of steps d, ensures that in reaction system, organic phase and inorganic phase volume ratio are 1: 1 ~ 2: 1 simultaneously.
F. suzuki reaction; product 4 in above-mentioned reactions steps c and the product 5 of reactions steps d; under the protection of rare gas element; with four (triphenyl phosphorus) palladium for catalyzer; toluene is solvent; add the solution of potassium carbonate of 2 moles often liter and the potassium fluoride solution of 2 moles often liter, 80 DEG C ~ 90 DEG C reaction for some time can obtain product 6 simultaneously.
In above-mentioned reaction, the product 4 of step c is 2.5: 1 ~ 15: 1 with the mol ratio of the product 5 of steps d, ensures that the volume ratio of organic phase and inorganic phase in reaction system is 1: 1 ~ 2: 1 simultaneously.
Further, in described step a, the reaction times is 4 hours to 8 hours; In described step b, the projection time is 12 hours to 48 hours; In described step c, the reaction times is 24 hours to 72 hours.In described step e, f, the reaction times is 12 hours to 48 hours.
Further, the organophosphor ligand in described step e, f is trimethyl-phosphine, triphenylphosphine, tri-butyl phosphine, and palladium catalyst is Pd (PPh
3)
4, PdCl
2(dppf), Pd (OAc)
2.
8. it is characterized in that the energy level of its molecule HOMO highest occupied molecular orbital (HOMO) is between-4.0eV and-6.0eV according to organic hole transport material according to claim 1.
9. by materials application according to claim 1 in electron device, comprising Organic Light Emitting Diode, organic field effect tube, organic memory device, organic solar batteries, dye-sensitized cell, and based on the solar cell etc. of perovskite material.
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| CN112778346A (en) * | 2021-01-22 | 2021-05-11 | 南京邮电大学 | Tetraborate intermediate for synthesizing photoelectric material and preparation method thereof |
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