KR20220002858A - 인데노카르바졸 고리를 갖는 화합물로 이루어지는 유기 박막을 구비하는 광전 변환 소자 - Google Patents
인데노카르바졸 고리를 갖는 화합물로 이루어지는 유기 박막을 구비하는 광전 변환 소자 Download PDFInfo
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- KR20220002858A KR20220002858A KR1020217022043A KR20217022043A KR20220002858A KR 20220002858 A KR20220002858 A KR 20220002858A KR 1020217022043 A KR1020217022043 A KR 1020217022043A KR 20217022043 A KR20217022043 A KR 20217022043A KR 20220002858 A KR20220002858 A KR 20220002858A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 85
- 150000001875 compounds Chemical class 0.000 title claims abstract description 77
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical group C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000010409 thin film Substances 0.000 title claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 113
- 125000001424 substituent group Chemical group 0.000 claims abstract description 95
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 239000000872 buffer Substances 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000004434 sulfur atom Chemical group 0.000 claims description 20
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- 238000003384 imaging method Methods 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004431 deuterium atom Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 123
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- 239000010410 layer Substances 0.000 description 47
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- 239000000843 powder Substances 0.000 description 40
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- 238000001914 filtration Methods 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 35
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 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 description 25
- -1 biphenylyl group Chemical group 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 24
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- 229910052757 nitrogen Inorganic materials 0.000 description 19
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 229910001873 dinitrogen Inorganic materials 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000004065 semiconductor Substances 0.000 description 15
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
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- 239000000463 material Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 150000002894 organic compounds Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000001678 irradiating effect Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002184 metal Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 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 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
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- 239000012046 mixed solvent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IFJKCEPOUBWFFD-UHFFFAOYSA-N 12-chloro-2,11,13,22,30,31-hexaza-12-boraoctacyclo[21.6.1.110,14.03,11.04,9.013,21.015,20.024,29]hentriaconta-1,3,5,7,9,14(31),15,17,19,21,23(30),24,26,28-tetradecaene Chemical compound N12B(Cl)N3C4=C(C=CC=C5)C5=C3N=C1C1=CC=CC=C1C2=NC(C1=CC=CC=C11)=NC1=N4 IFJKCEPOUBWFFD-UHFFFAOYSA-N 0.000 description 4
- VSIHMCNNUMIHKD-UHFFFAOYSA-N 7-bromo-12,12-dimethyl-10-phenyl-10h-indeno[2,1-b]carbazole Chemical compound C1=C2N=C3C=CC=CC3=C2C(C)(C)C(C2=C3)=C1C(Br)=C2C=CC3C1=CC=CC=C1 VSIHMCNNUMIHKD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 4
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- YZSBOFITLUNUHC-UHFFFAOYSA-N 12,12-dimethyl-10h-indeno[2,1-b]carbazole Chemical compound C1=C2N=C3C=CC=CC3=C2C(C)(C)C2=C1C=C1C2=CCC=C1 YZSBOFITLUNUHC-UHFFFAOYSA-N 0.000 description 3
- DJCMIYLUCGKDQX-UHFFFAOYSA-N 2-bromo-5,7,7-triphenylindeno[2,1-b]carbazole Chemical compound BrC=1C=C2C=3C=C4C(=CC=3N(C2=CC=1)C1=CC=CC=C1)C(C1=CC=CC=C14)(C1=CC=CC=C1)C1=CC=CC=C1 DJCMIYLUCGKDQX-UHFFFAOYSA-N 0.000 description 3
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- AIDQRXUWQFRMAQ-UHFFFAOYSA-N (6,9-diphenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 AIDQRXUWQFRMAQ-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QRMUUHGMRZMBDQ-UHFFFAOYSA-N 12,12-dimethyl-10-(4-phenylphenyl)-10h-indeno[2,1-b]carbazole Chemical compound C1=C2N=C3C=CC=CC3=C2C(C)(C)C(C2=C3)=C1C=C2C=CC3C(C=C1)=CC=C1C1=CC=CC=C1 QRMUUHGMRZMBDQ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ZWMKCBPAUHHTMR-UHFFFAOYSA-N 5,7,7-triphenylindeno[2,1-b]carbazole Chemical compound C1=CC=CC=C1N1C2=CC(C(C3=CC=CC=C33)(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3C=C2C2=CC=CC=C21 ZWMKCBPAUHHTMR-UHFFFAOYSA-N 0.000 description 2
- RREJCBICPNWJRE-UHFFFAOYSA-N 7-bromo-12,12-dimethyl-10-(4-phenylphenyl)-10h-indeno[2,1-b]carbazole Chemical compound C1=C2N=C3C=CC=CC3=C2C(C)(C)C(C2=C3)=C1C(Br)=C2C=CC3C(C=C1)=CC=C1C1=CC=CC=C1 RREJCBICPNWJRE-UHFFFAOYSA-N 0.000 description 2
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- UBASCOPZFCGGAV-UHFFFAOYSA-N 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 UBASCOPZFCGGAV-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- 238000010521 absorption reaction Methods 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
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
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- 125000004623 carbolinyl group Chemical group 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
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- 229910003472 fullerene Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
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- 229910010272 inorganic material Inorganic materials 0.000 description 2
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- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
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| JP2019081340 | 2019-04-22 | ||
| JPJP-P-2019-081340 | 2019-04-22 | ||
| PCT/JP2020/017107 WO2020218264A1 (ja) | 2019-04-22 | 2020-04-20 | インデノカルバゾール環を有する化合物からなる有機薄膜を備える光電変換素子 |
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| JP (1) | JP7655850B2 (https=) |
| KR (1) | KR20220002858A (https=) |
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| TW202404063A (zh) * | 2022-05-25 | 2024-01-16 | 日商日鐵化學材料股份有限公司 | 攝像用的光電轉換元件用材料及光電轉換元件 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007234651A (ja) | 2006-02-27 | 2007-09-13 | Fujifilm Corp | 光電変換素子及び固体撮像素子 |
| US9085537B2 (en) | 2010-02-09 | 2015-07-21 | Fujifilm Corporation | Photoelectric element and imaging device and driving methods therefor |
| US9196837B2 (en) | 2010-07-30 | 2015-11-24 | Hodogaya Chemical Co., Ltd. | Compound having indenocarbazole ring structure, and organic electroluminescent device |
| JP2018170487A (ja) | 2016-09-13 | 2018-11-01 | 日本化薬株式会社 | 撮像素子用光電変換素子 |
| US20190081251A1 (en) | 2016-03-15 | 2019-03-14 | Sony Corporation | Photoelectric conversion element and solid-state imaging device |
| US20190288040A1 (en) | 2016-11-22 | 2019-09-19 | Sony Corporation | Imaging element, stacked-type imaging element, imaging apparatus and electronic apparatus |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005250351A (ja) * | 2004-03-08 | 2005-09-15 | Konica Minolta Medical & Graphic Inc | 放射線画像検出器及び放射線画像検出器の残留電荷除去方法 |
| KR101408515B1 (ko) * | 2009-07-01 | 2014-06-17 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
| DE102009043348B4 (de) * | 2009-09-29 | 2012-12-13 | Siemens Aktiengesellschaft | Material für eine photoaktive Schicht in organischen Photodioden, Verwendung dazu, sowie eine organische Photodiode |
| KR20130112342A (ko) * | 2012-04-03 | 2013-10-14 | 롬엔드하스전자재료코리아유한회사 | 신규한 카바졸 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| WO2015154843A1 (de) * | 2014-04-11 | 2015-10-15 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
| CN107851652A (zh) * | 2015-11-12 | 2018-03-27 | 松下知识产权经营株式会社 | 光传感器 |
| US11476426B2 (en) * | 2016-02-03 | 2022-10-18 | Sfc Co., Ltd. | Organic light emitting compounds and organic light emitting devices including the same |
| JP2017174954A (ja) * | 2016-03-23 | 2017-09-28 | キヤノン株式会社 | 光電変換装置、及び撮像装置 |
| KR102639854B1 (ko) * | 2016-10-31 | 2024-02-22 | 엘지디스플레이 주식회사 | 유기 화합물과 이를 이용한 발광다이오드 및 유기발광다이오드 표시장치 |
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2020
- 2020-04-20 WO PCT/JP2020/017107 patent/WO2020218264A1/ja not_active Ceased
- 2020-04-20 JP JP2021516113A patent/JP7655850B2/ja active Active
- 2020-04-20 KR KR1020217022043A patent/KR20220002858A/ko not_active Ceased
- 2020-04-21 TW TW109113345A patent/TWI871314B/zh active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007234651A (ja) | 2006-02-27 | 2007-09-13 | Fujifilm Corp | 光電変換素子及び固体撮像素子 |
| US9085537B2 (en) | 2010-02-09 | 2015-07-21 | Fujifilm Corporation | Photoelectric element and imaging device and driving methods therefor |
| US9196837B2 (en) | 2010-07-30 | 2015-11-24 | Hodogaya Chemical Co., Ltd. | Compound having indenocarbazole ring structure, and organic electroluminescent device |
| US20190081251A1 (en) | 2016-03-15 | 2019-03-14 | Sony Corporation | Photoelectric conversion element and solid-state imaging device |
| JP2018170487A (ja) | 2016-09-13 | 2018-11-01 | 日本化薬株式会社 | 撮像素子用光電変換素子 |
| US20190288040A1 (en) | 2016-11-22 | 2019-09-19 | Sony Corporation | Imaging element, stacked-type imaging element, imaging apparatus and electronic apparatus |
Non-Patent Citations (2)
| Title |
|---|
| Adv. Mater. 28, 4766 (2016) |
| 영상 정보학회 미디어 협회지, 60, 3, 291 (2006) |
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| JPWO2020218264A1 (https=) | 2020-10-29 |
| TW202104183A (zh) | 2021-02-01 |
| TWI871314B (zh) | 2025-02-01 |
| WO2020218264A1 (ja) | 2020-10-29 |
| JP7655850B2 (ja) | 2025-04-02 |
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