CN110467628B - 一种半导体材料及其制备方法与应用 - Google Patents
一种半导体材料及其制备方法与应用 Download PDFInfo
- Publication number
- CN110467628B CN110467628B CN201810440306.7A CN201810440306A CN110467628B CN 110467628 B CN110467628 B CN 110467628B CN 201810440306 A CN201810440306 A CN 201810440306A CN 110467628 B CN110467628 B CN 110467628B
- Authority
- CN
- China
- Prior art keywords
- intermediate product
- structural formula
- reacting
- mixing
- molecular structural
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 90
- 239000004065 semiconductor Substances 0.000 title claims abstract description 86
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000013067 intermediate product Substances 0.000 claims description 163
- 238000002156 mixing Methods 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 96
- 239000000243 solution Substances 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- 239000012467 final product Substances 0.000 claims description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 16
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 229960000583 acetic acid Drugs 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 8
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012362 glacial acetic acid Substances 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 claims description 8
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- BPARGYSSDVENMT-UHFFFAOYSA-N ethyl 3-sulfanylprop-2-enoate Chemical compound CCOC(=O)C=CS BPARGYSSDVENMT-UHFFFAOYSA-N 0.000 claims description 6
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 claims description 6
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 5
- RQXGHBYRZRBUQC-UHFFFAOYSA-N 1,5-dimethylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=CC2=C1C RQXGHBYRZRBUQC-UHFFFAOYSA-N 0.000 claims description 4
- FXEGEEUPPGLIIC-UHFFFAOYSA-N 1-bromo-3-fluoro-2-iodobenzene Chemical compound FC1=CC=CC(Br)=C1I FXEGEEUPPGLIIC-UHFFFAOYSA-N 0.000 claims description 4
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- TVWZZZGXVSUJSE-UHFFFAOYSA-N 5,6-dibromo-5-methylcyclohexa-1,3-diene Chemical compound CC1(Br)C=CC=CC1Br TVWZZZGXVSUJSE-UHFFFAOYSA-N 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000013086 organic photovoltaic Methods 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZCXOSDRICFIHTA-UHFFFAOYSA-N n-methylaniline;hydrochloride Chemical compound [Cl-].C[NH2+]C1=CC=CC=C1 ZCXOSDRICFIHTA-UHFFFAOYSA-N 0.000 claims 1
- 238000012986 modification Methods 0.000 abstract description 6
- 230000004048 modification Effects 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 4
- 125000005462 imide group Chemical group 0.000 abstract description 4
- 150000003949 imides Chemical class 0.000 abstract description 4
- 238000009825 accumulation Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 35
- 238000001035 drying Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 17
- 238000001816 cooling Methods 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 238000010791 quenching Methods 0.000 description 9
- 230000000171 quenching effect Effects 0.000 description 9
- 238000002390 rotary evaporation Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- HZSATSWHBKSURR-UHFFFAOYSA-N chloro(trioctyl)silane Chemical compound CCCCCCCC[Si](Cl)(CCCCCCCC)CCCCCCCC HZSATSWHBKSURR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- -1 phenylamine compound Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electromagnetism (AREA)
- Optics & Photonics (AREA)
- Indole Compounds (AREA)
- Thin Film Transistor (AREA)
Abstract
Description
技术领域
本发明涉及有机材料领域,尤其涉及一种半导体材料及其制备方法与应用。
背景技术
自从有机场效应晶体管问世以来,由于其具有溶液加工、工艺简单、可大面积生产等优点,因而在集成电路、射频识别、智能卡等电子电路中有着较为广泛的应用。目前,已经出现了一系列具有高的空穴迁移率和电子迁移率的小分子半导体材料,其中,p型材料如BTBT,蒽,并五苯衍生物等,其中BTBT的衍生物的迁移率已经超过25cm2/V/S,红荧烯的单晶器件效率超过40cm2/V/S。n型材料如NDI,PDI衍生物以及其他一些杂环体系衍生物等,n型材料的迁移率已经有报道超过10cm2/V/S。
与p型半导体材料相比,n型半导体材料的迁移率相对较低,并且由于电子对于氧气和水的敏感性,n型有机半导体的稳定性比较低,其材料种类也比较有限,因而其发展与p型有机半导体的相比较为落后,使得有机半导体的实际应用受到了一定的限制。
因此,现有技术还有待于改进和发展。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种半导体材料及其制备方法与应用,旨在解决现有n型半导体材料载流子迁移率较低以及稳定性较差的问题。
本发明的技术方案如下:
一种半导体材料,其中,所述半导体材料的分子结构通式为
所述的半导体材料,其中,所述烷基为碳原子数为1-18的直链烷基、支链烷基或氟烷基。
所述的半导体材料,其中,所述芳香基团为苯基、噻吩基、芴、吡啶基、吡咯、咔唑、噻二唑或哌啶中的一种。
所述的半导体材料,其中,所述半导体材料的分子结构式包括:
一种半导体材料的制备方法,其中,包括步骤:
一种半导体材料的制备方法,其中,包括步骤:
一种半导体材料的制备方法,其中,包括步骤:
一种半导体材料,其中,包括步骤:
一种半导体材料的应用,其中,将所述的半导体材料用于制备有机薄膜晶体管、有机发光二极管和有机光伏器件
有益效果:本发明提供的半导体材料为酰亚胺衍生物,其中,酰亚胺基团可以有效降低半导体分子材料的能级,从而提高材料的稳定性,对胺进行不同取代基修饰,可以有效的调整材料的能级、溶解度及分子堆积方式,进而得到迁移率较高、稳定性较高、可溶液加工的n型半导体材料。
具体实施方式
本发明提供一种半导体材料及其制备方法与应用,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
与P型半导体材料相比,现有的n型半导体材料的载流子迁移率相对交底,并且由于电子对氧气和水的敏感性,所述n型半导体的稳定性也比价低。现有n型半导体材料的种类也较少,其发展与P型油价半导体相比比较落后,导致有机半导体的实际应用受到一定限制。
为解决现有n型半导体所存在的问题,本发明提供一种n型半导体材料,其分子结构通式为: 中的一种,其中,所述R1、R2独立选自烷基或烷基取代的芳香基团中的一种,所述X、Y独立选自F、Cl、Br、CN、含氧烷基链或者含氟烷基链中的一种,所述M、P独立选自O、S或Se中的一种。
优选地,所述烷基为碳原子数为1-18的直链烷基、支链烷基或氟烷基,所述芳香基团为苯基、噻吩基、芴、吡啶基、吡咯、咔唑、噻二唑或哌啶中的一种。
本发明提供的半导体材料为酰亚胺衍生物,其中,酰亚胺基团可以有效降低半导体分子材料的能级,从而提高材料的稳定性,对胺进行不同取代基修饰,可以有效的调整材料的能级、溶解度及分子堆积方式,进而得到迁移率较高、稳定性较高、可溶液加工的n型半导体材料。
本发明中的烷基为碳原子数为1-18的直链烷基、支链烷基或氟烷基,所述芳香基团为苯基、噻吩基、芴、吡啶基、吡咯、咔唑、噻二唑或哌啶中的一种。通过改变取代基烷基链的长短,可优化分子堆积方式,减小分子间的间距,增大π-π共轭面重叠,从而提高载流子在分子间的传递效率;进一步地,通过改变取代基的供/吸电子特性,可以调控分子的LUMO/HOMO能级,通过引入吸电子基团来降低能级,供电子基团来升高能级,进一步对轨道能级进行微调,保证载流子在器件中的稳定传输,从而改善载流子迁移率和器件稳定性。
基于上述材料,本发明还提供了一种半导体材料的制备方法,其中,包括步骤:
作为其中一实施方式,本发明还提供了另一种半导体材料的制备方法,其中,包括步骤:
作为其中一实施方式,本发明还提供了另一种半导体材料的制备方法,其中,包括步骤:
作为其中一实施方式,本发明还提供了另一种半导体材料,其中,包括步骤:
本发明还提供一种半导体材料的应用,其中,将所述的半导体材料用于制备有机薄膜晶体管(OTFT)、有机发光二极管(OLED)和有机光伏器件(OPV),具体地,所述半导体材料可用于制备发光二极管的发光层或电子传输层或电子注入层。
下面通过具体实施例对本发明一种半导体材料的制备方法做进一步的解释说明:
a、氮气氛围下,将30g 1-溴-3-氟-碘苯溶解于400ml无水乙醚中,在-78℃下逐滴加入40ml 2.5M的正丁基锂溶液,加完后,再加入24g溴化铜,低温下搅拌一个小时,再加入14g硝基苯,室温下搅拌过夜,加水淬灭反应,分液,有机相用无水硫酸钠干燥,旋蒸除去溶剂,过柱纯化,得到7.83g分子结构式为的白色固体B1,产率45%;
b、氮气氛围中,将3.48g化合物B1溶于100ml无水甲苯中,加入3.4g3-巯基丙烯酸乙酯,0.17g三(二亚苄基丙酮)二钯和8.65g无水碳酸钾,110℃加热20h,冷却,用100ml的5%醋酸溶液淬灭,乙酸乙酯萃取,无水硫酸钠干燥,旋蒸除去溶剂,过柱纯化,得到3.5g分子结构式为的白色固体C1,产率77%;
c、将4.5g C1加入100ml无水四氢呋喃中,加入3.3g叔丁醇钾,室温下下搅拌1h,用40ml的5%醋酸溶液淬灭酸化,乙酸乙酯萃取,用无水硫酸钠干燥有机相,旋蒸除去溶剂,过柱纯化,得到2.2g分子结构式为的白色固体D1,产率87%;
d、取5.08g D1溶解在120ml无水二甲基亚砜中,加入16.3g碳酸铯,氮气氛围下加热回流过夜,冷却,水洗除去盐,乙酸乙酯萃取,有机相用无水硫酸钠干燥,旋蒸除去溶剂,过柱纯化得到3.1g分子结构式为白色固体E1,产率72%;
e、取4.28g E1溶解在50ml氯仿溶液中,将8g液溴逐滴加入,加热回流过夜,用50ml的10%硫代硫酸钠溶液除去多余的溴,用乙酸乙酯萃取分液,无水硫酸钠干燥有机相,旋干,过柱,得到6.1g分子结构式为的白色固体F1,产率60%;
a、将17.4g氯代邻二甲苯溶解在250ml二氯甲烷中,加入0.5TMBAC,50ml九水合硫化钠(36g)溶液逐滴加入到二氯甲烷溶液中,加热回流过夜,冷却,水洗,有机相用无水硫酸钠干燥,旋干,柱层析纯化,得到7.48g分子结构式为的透明液体B2,产率55%;
b、取5.44g化合物B2溶于100ml氯仿,0℃下逐滴加入NaIO4(8.56g)溶液,搅拌过夜,抽滤除去无机盐,旋干,用乙酸乙酯和石油醚重结晶,得到4.5g分子结构式为的白色固体C2,产率75%;
d、-20℃情况下,将2.6gD2溶于100ml无水二氯甲烷中,加入5.34g无水氯化铝,逐滴加入2.52g草酰氯,低温下搅拌一个小时,升至室温搅拌过夜,加水淬灭,乙酸乙酯萃取,有机相用无水硫酸钠干燥,旋蒸除去溶剂,柱层析纯化,得到2.5g分子结构式为的白色固体E2,产率52%;
e、将4.8g化合物E2溶解在100ml二氧六环中,加入10ml氢氧化钠(3.2g)水溶液,搅拌,升温到60℃,逐滴加入3.6ml双氧水(30%,31.5mmol),继续搅拌2h,冰水浴中,加入50%硫酸溶液调制PH=1,有固体析出,抽滤,烘干,得到3.42g分子结构式为的白色固体F2,产率55%;
a、将17.1g3-溴邻二溴带甲苯溶于200mlDCM中,加入0.5gTEMBAC,100ml(18g)九水合硫化钠溶液逐滴加入,搅拌回流过夜,冷却,水洗,分液,有机相用无水硫酸钠干燥,旋干,柱层析纯化,得到6.1g分子结构式为的白色固体B3,产率57%;
b、氮气氛围下,将0.6gNiCl2和1.45g2,2’-联吡啶加入到15ml无水DMF中,加热到70℃,20分钟后,逐滴加入10ml B3(1g)的DMF溶液,70℃下搅拌12小时,冷却,减压蒸馏除去DMF,水洗固体,DCM萃取,无水硫酸钠干燥有机相,浓缩、纯化,得到0.26g分子结构式为的黄色固体C3,产率41%;
c、将1.6gC3溶解在100mlTHF中,加入35ml(2.7g)高碘酸钠水溶液,室温搅拌过夜,二氯甲烷萃取,无水硫酸铵干燥二氯甲烷溶液,旋干,粗产品用柱层析纯化,得到1.7g分子结构式为的黄色固体D3,产率91%;
d、氮气氛围下,将2gD3溶解在200ml无水THF下,冷却至-80℃,逐滴加入24ml正丁基锂(2.5M)溶液,搅拌1小时后,逐滴加入20mlN,N’-二甲基甲酰氯(5.31g)的THF溶液,升至室温,搅拌过夜,加水淬灭,乙酸乙酯萃取,干燥浓缩有机相,柱层析纯化,得到2.7g分子结构式为的黄色固体E3,产率40%;
e、将1gE3溶解到50ml无水甲苯中,逐滴加入20ml氯化铁(7.5g)的硝基甲烷溶液,暗处室温搅拌2h,加水淬灭,乙酸乙酯萃取,浓缩,柱层析纯化,得到0.4g分子结构式为的深蓝色固体F3,产率40%;
h、将0.91gH3加入到50ml(V:V=1:1)的硫酸和冰乙酸混合溶液中,80℃加热回流过夜,冷却,加水稀释,调制PH=7,有固体析出,水洗至中性,真空干燥,得到0.6g分子结构式为的白色固体I3,产物直接投入下一步;
i、将0.6g I3溶解在100ml甲苯溶液中,加入34mg醋酸钯,336mg叔丁醇钾,40mg三叔丁基膦,加入0.5g溴苯,氮气氛围下加热回流2d,冷却,冰水浴下加入50ml水,抽滤,固体升华纯化,得到0.42g的目标产物产率51%。
a、将10.3g 1,5-二甲基蒽溶解在600ml氯仿中,滴加19.2ml液溴,室温下搅拌过夜,用饱和硫代硫酸钠溶液水洗,萃取,浓缩,用氯仿、乙醇重结晶,得到14.3g分子结构式为的黄色固体B4,产率78.6%;
c、氮气氛围中,将3.48g化合物B1溶于100ml无水甲苯中,加入3.4g3-巯基丙烯酸乙酯,0.17g三(二亚苄基丙酮)二钯和8.65g无水碳酸钾,110℃加热20h,冷却,用100ml的5%醋酸溶液淬灭,乙酸乙酯萃取,无水硫酸钠干燥,旋蒸除去溶剂,过柱纯化,得到3.5g分子结构式为白色固体D4,产率77%;
d、将4.5g D4加入100ml无水四氢呋喃中,加入3.3g叔丁醇钾,室温下下搅拌1h,用40ml的5%醋酸溶液淬灭酸化,乙酸乙酯萃取,用无水硫酸钠干燥有机相,旋蒸除去溶剂,过柱纯化,得到2.2g分子结构式为的白色固体E4,产率87%;
e、取5.08g E4溶解在120ml无水二甲基亚砜中,加入16.3g碳酸铯,氮气氛围下加热回流过夜,冷却,水洗除去盐,乙酸乙酯萃取,有机相用无水硫酸钠干燥,旋蒸除去溶剂,过柱纯化得到3.1g分子结构式为的白色固体F4,产率72%;
f、将1.6g F4溶解在100mlTHF中,加入35ml(2.7g)高碘酸钠水溶液,室温搅拌过夜,二氯甲烷萃取,无水硫酸铵干燥二氯甲烷溶液,旋干,粗产品用柱层析纯化,得到1.7g分子结构式为的黄色固体G4,产率91%;;
g、氮气氛围下,将2g G4溶解在200ml无水THF下,冷却至-80℃,逐滴加入24ml正丁基锂(2.5M)溶液,搅拌1小时后,逐滴加入20mlN,N’-二甲基甲酰氯(5.31g)的THF溶液,升至室温,搅拌过夜,加水淬灭,乙酸乙酯萃取,干燥浓缩有机相,柱层析纯化,得到2.7g分子结构式为的黄色固体H4,产率40%;
j、将0.91g J4加入到50ml(V:V=1:1)的硫酸和冰乙酸混合溶液中,80℃加热回流过夜,冷却,加水稀释,调制PH=7,有固体析出,水洗至中性,真空干燥,得到0.6g分子结构式为的白色固体K4,产物直接投入下一步;
k、将0.6g K4溶解在100ml甲苯溶液中,加入34mg醋酸钯,336mg叔丁醇钾,40mg三叔丁基膦,加入0.5g溴苯,氮气氛围下加热回流2d,冷却,冰水浴下加入50ml水,抽滤,固体升华纯化,得到0.42g的目标产物
进一步地,本发明还将实施例1-4中制备的半导体材料进行了OTFT(有机薄膜晶体管)器件制备与表征,具体制备方法为:
将Si片相继在异丙醇、去离子水和丙酮中以超声波清洗30分钟,真空干燥2小时;紫外UV照射半小时,用0.5M/L的三辛基氯化硅的甲苯溶液在60℃加热2h,甲苯洗去残留三辛基氯化硅,通过真空蒸镀的方法实施例1-4中的半导体材料分别沉积在Si片基底上,再真空蒸镀Au电极,制得4个不同半导体材料制备的OTFT器件。
将所述4个OTFT器件暴露在空气中运行,结果发现,所述4个OTFT器件均能够在空气环境中长期、稳定地运行,并且显示出了较为优异的半导体性能,载流子迁移率达到了4~5cm2/V/S。
综上所述,本发明提供的半导体材料为酰亚胺衍生物,其中,酰亚胺基团可以有效降低半导体分子材料的能级,从而提高材料的稳定性,对胺进行不同取代基修饰,可以有效的调整材料的能级、溶解度及分子堆积方式,进而得到迁移率较高、稳定性较高、可溶液加工的n型半导体材料。
应当理解的是,本发明的应用不限于上述的举例,对本领域普通技术人员来说,可以根据上述说明加以改进或变换,所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (9)
2.根据权利要求1所述的半导体材料,其特征在于,所述烷基为碳原子数为1-18的直链烷基、支链烷基或氟烷基。
3.根据权利要求1所述的半导体材料,其特征在于,所述芳香基团为苯基、噻吩基、芴、吡啶基、吡咯、咔唑、噻二唑中的一种。
5.一种半导体材料的制备方法,其特征在于,包括步骤:
6.一种半导体材料的制备方法,其特征在于,包括步骤:
7.一种半导体材料的制备方法,其特征在于,包括步骤:
8.一种半导体材料,其特征在于,包括步骤:
9.一种半导体材料的应用,其特征在于,将权利要求1-4任一所述的半导体材料用于制备有机薄膜晶体管、有机发光二极管和有机光伏器件。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810440306.7A CN110467628B (zh) | 2018-05-10 | 2018-05-10 | 一种半导体材料及其制备方法与应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810440306.7A CN110467628B (zh) | 2018-05-10 | 2018-05-10 | 一种半导体材料及其制备方法与应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110467628A CN110467628A (zh) | 2019-11-19 |
CN110467628B true CN110467628B (zh) | 2021-12-28 |
Family
ID=68503763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810440306.7A Active CN110467628B (zh) | 2018-05-10 | 2018-05-10 | 一种半导体材料及其制备方法与应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110467628B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115093430A (zh) * | 2022-04-02 | 2022-09-23 | 武汉工程大学 | 一种异硫茚二酰亚胺衍生物及其制备方法与应用 |
CN116546824A (zh) * | 2022-05-07 | 2023-08-04 | 浙江大学 | 一种有机场效应晶体管及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101468493B1 (ko) * | 2012-10-10 | 2014-12-03 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
WO2017022735A1 (ja) * | 2015-08-04 | 2017-02-09 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機薄膜トランジスタの製造方法、有機薄膜トランジスタ用材料、有機薄膜トランジスタ用組成物、有機半導体膜、化合物 |
-
2018
- 2018-05-10 CN CN201810440306.7A patent/CN110467628B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101468493B1 (ko) * | 2012-10-10 | 2014-12-03 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
WO2017022735A1 (ja) * | 2015-08-04 | 2017-02-09 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機薄膜トランジスタの製造方法、有機薄膜トランジスタ用材料、有機薄膜トランジスタ用組成物、有機半導体膜、化合物 |
Non-Patent Citations (1)
Title |
---|
有机半导体的分子设计及有机电子应用;孟鸿;《光学与光电技术》;20180228;第16卷(第1期);1-4 * |
Also Published As
Publication number | Publication date |
---|---|
CN110467628A (zh) | 2019-11-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107586261B (zh) | 一种含有螺二苯并环庚烯芴的有机化合物及其应用 | |
JP6025748B2 (ja) | チオシアネート又はイソチオシアネートで置換したナフタレンジイミド及びリレンジイミド化合物、並びにn−タイプ半導体としてのそれらの使用 | |
EP2132213A1 (en) | Silylethynylated heteroacenes and electronic devices made therewith | |
JP5438363B2 (ja) | バンドギャップが広いことを特徴とする有機半導体材料 | |
CN110467628B (zh) | 一种半导体材料及其制备方法与应用 | |
CN110885334A (zh) | 一种以苯并[1,2-b:3,4-b’]二苯并呋喃为核心的有机化合物及其应用 | |
CN111362813A (zh) | 一种以三芳胺为核心的化合物及其应用 | |
CN110526825B (zh) | 一种以异屈与三芳胺结构为核心的化合物及其应用 | |
CA2977170C (en) | Thienothiophenes and dithienothiophenes, incorporating triphenylamine, tetraphenylethylene and their varying compositions for organic light emitting diodes | |
CN111718280A (zh) | 一种p型掺杂空穴注入化合物及其应用 | |
CN112479978A (zh) | 一种以咔唑衍生物为核心的有机化合物及其应用 | |
CN113372289A (zh) | 一种含有菲并唑类化合物的有机电子材料及其制备方法和应用 | |
CN109020978B (zh) | 一类星型荧光分子及其制备方法与应用 | |
CN112661771B (zh) | 一种基于咔唑不对称稠环的星型荧光材料及其制备方法与应用 | |
CN109897055B (zh) | 一种基于联二咔唑和苝二酰亚胺的有机化合物及其制备方法和应用 | |
CN114685533A (zh) | 一种吲哚[3,2,1-kl]吩噻嗪5,5-二氧化物衍生物及其应用和电子器件 | |
CN109134494B (zh) | 一类含极性取代基团蒽衍生物的电致发光材料及其制备方法与应用 | |
CN110343049B (zh) | 一种以螺二苯并环庚烯芴为骨架的有机化合物及其应用 | |
CN108863871B (zh) | 一类芘衍生物的电致发光材料及其制备方法与应用 | |
CN114685534A (zh) | 一种吲哚并[3,2,1-kl]吩噻嗪衍生物光电材料及其应用和电子器件 | |
CN111848624A (zh) | 一种苯并二咪唑类的化合物、空穴注入材料、oled器件及其制备方法和应用 | |
CN111233675A (zh) | 一种含苯并蒽的有机化合物及其应用 | |
CN112480002A (zh) | 一种含苯并蒽的有机化合物及其应用 | |
CN113087720B (zh) | 一类基于苯并噻吩并[3,2-b]苯并噻吩的n型有机半导体材料及其制备方法和应用 | |
CN113527330B (zh) | 一种化合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |