WO2016194717A1 - 固体撮像素子、光電変換膜、電子ブロック層、撮像装置、および電子機器 - Google Patents
固体撮像素子、光電変換膜、電子ブロック層、撮像装置、および電子機器 Download PDFInfo
- Publication number
- WO2016194717A1 WO2016194717A1 PCT/JP2016/065386 JP2016065386W WO2016194717A1 WO 2016194717 A1 WO2016194717 A1 WO 2016194717A1 JP 2016065386 W JP2016065386 W JP 2016065386W WO 2016194717 A1 WO2016194717 A1 WO 2016194717A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- atom
- group
- chemical formula
- coupler
- photoelectric conversion
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 188
- 238000003384 imaging method Methods 0.000 title claims abstract description 100
- 230000000903 blocking effect Effects 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 239000000126 substance Substances 0.000 claims abstract description 115
- 125000004429 atom Chemical group 0.000 claims description 76
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 71
- 125000004437 phosphorous atom Chemical group 0.000 claims description 64
- 229910052698 phosphorus Inorganic materials 0.000 claims description 64
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 55
- 229910052710 silicon Inorganic materials 0.000 claims description 55
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 48
- 125000004434 sulfur atom Chemical group 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 16
- 229910052796 boron Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 abstract description 26
- 230000003595 spectral effect Effects 0.000 abstract description 12
- 239000010410 layer Substances 0.000 description 106
- 238000005516 engineering process Methods 0.000 description 52
- 239000004065 semiconductor Substances 0.000 description 39
- 150000001721 carbon Chemical group 0.000 description 38
- 239000000758 substrate Substances 0.000 description 36
- 238000010521 absorption reaction Methods 0.000 description 12
- 238000000137 annealing Methods 0.000 description 12
- 230000002776 aggregation Effects 0.000 description 11
- 238000004220 aggregation Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 229940125898 compound 5 Drugs 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 238000010586 diagram Methods 0.000 description 6
- -1 polyarylalkane Chemical class 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000004020 conductor Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 0 C*c1c(*C)c(C)c(*)c(C)c1C Chemical compound C*c1c(*C)c(C)c(*)c(C)c1C 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 238000005036 potential barrier Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c2ccccc2c2ccccc12 Chemical compound C[n]1c2ccccc2c2ccccc12 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 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
- KNMCEFKBUOWEAX-UHFFFAOYSA-N b1cbcbc1 Chemical compound b1cbcbc1 KNMCEFKBUOWEAX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- 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
- 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 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- 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 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- ONKCIMOQGCARHN-UHFFFAOYSA-N 3-methyl-n-[4-[4-(3-methylanilino)phenyl]phenyl]aniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C=CC(NC=3C=C(C)C=CC=3)=CC=2)=C1 ONKCIMOQGCARHN-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 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
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000004050 hot filament vapor deposition Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
- H10K39/30—Devices controlled by radiation
- H10K39/32—Organic image sensors
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14665—Imagers using a photoconductor layer
- H01L27/14669—Infrared imagers
- H01L27/1467—Infrared imagers of the hybrid type
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14643—Photodiode arrays; MOS imagers
- H01L27/14645—Colour imagers
- H01L27/14647—Multicolour imagers having a stacked pixel-element structure, e.g. npn, npnpn or MQW elements
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14665—Imagers using a photoconductor layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K19/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00
- H10K19/20—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00 comprising components having an active region that includes an inorganic semiconductor
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
- H10K39/30—Devices controlled by radiation
- H10K39/36—Devices specially adapted for detecting X-ray radiation
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
- H01L31/0256—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by the material
- H01L2031/0344—Organic materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1464—Back illuminated imager structures
-
- 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
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K30/353—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains comprising blocking layers, e.g. exciton blocking layers
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/658—Organoboranes
-
- 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
Definitions
- the present technology relates to a solid-state imaging device, a photoelectric conversion film, an electronic block layer, an imaging device, and an electronic device, and in particular, a solid-state imaging device, a photoelectric conversion film having high spectral characteristics, high photoelectric conversion characteristics, and high heat resistance,
- the present invention relates to an electronic block layer, an imaging device, and an electronic device.
- Patent Document 1 For example, a solid-state imaging device in which organic photoelectric conversion films that respectively absorb blue light, green light, and red light are sequentially stacked is disclosed (see Patent Document 1).
- the solid-state imaging device disclosed in Patent Document 1 light of each color is extracted by photoelectrically converting light corresponding to each color in each organic photoelectric conversion film.
- Patent Document 2 a solid-state imaging device in which an organic photoelectric conversion film that absorbs green light and a silicon photodiode are sequentially stacked is disclosed (see Patent Document 2).
- a green light signal is extracted by an organic photoelectric conversion film, and a blue light signal and a red light signal are separated by using a difference in light penetration depth by a silicon photodiode. Has been removed.
- a heat treatment process of several hours is required under a temperature condition exceeding 150 ° C. For example, if the film quality changes due to this heating, the target function may not be exhibited.
- the present technology has been made in view of such circumstances, and in particular, a photoelectric conversion film having high spectral characteristics and high photoelectric conversion characteristics with respect to light of a specific wavelength, and further having high heat resistance. It is realized.
- a solid-state imaging device is a solid-state imaging device including a compound represented by the following chemical formula (1).
- A is a compound composed of an aryl group or a heteroaryl group, and Y1 and Y2 are linked via one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom.
- X1, X2 represents a coupler connected through one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom, silicon atom, and L1, L2, And any one of L3 and L4 is bonded to each other and connected via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom.
- each of L5 and L6, and L7 and L8 is bonded to each other and selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- R1 to R16 each represents a coupler connected via one atom selected from the group consisting of independent hydrogen atoms or substituents other than hydrogen atoms. .
- the A can have a molecular weight greater than 75.
- the compound represented by the chemical formula (1) can have a molecular weight larger than 620.
- the compound represented by the chemical formula (1) can have a molecular weight smaller than 1000.
- A may include compounds of the following chemical formulas (3) to (6), B in the chemical formula (3) is different from A in the chemical formula (1), and each represents a carbon atom or a nitrogen atom.
- R21 in the chemical formula (6) may be an aryl group or a heteroaryl group.
- the compound represented by the chemical formula (1) can include a compound of the following chemical formula (9), Ax in the chemical formula (9) is represented by the following chemical formula (3): B in the chemical formula (3) is different from A in the chemical formula (1), and can represent that each is a carbon atom or a nitrogen atom.
- any of the layers stacked between the pair of electrodes can be composed of the compound of the chemical formula (1).
- the photoelectric conversion film of one side of this indication is a photoelectric conversion film containing the compound denoted by the following chemical formula (1).
- A is a compound composed of an aryl group or a heteroaryl group, and Y1 and Y2 are linked via one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom.
- X1, X2 represents a coupler connected through one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom, silicon atom, and L1, L2, And any one of L3 and L4 is bonded to each other and connected via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom.
- each of L5 and L6, and L7 and L8 is bonded to each other and selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- R1 to R16 each represents a coupler connected via one atom selected from the group consisting of independent hydrogen atoms or substituents other than hydrogen atoms. .
- the electronic block layer of one side of this indication is an electronic block layer containing the compound denoted by the following chemical formula (1).
- A is a compound composed of an aryl group or a heteroaryl group, and Y1 and Y2 are linked via one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom.
- X1, X2 represents a coupler connected through one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom, silicon atom, and L1, L2, And any one of L3 and L4 is bonded to each other and connected via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom.
- each of L5 and L6, and L7 and L8 is bonded to each other and selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- R1 to R16 each represents a coupler connected via one atom selected from the group consisting of independent hydrogen atoms or substituents other than hydrogen atoms. .
- the imaging device of one side of this indication is an imaging device containing the compound denoted by the following chemical formula (1).
- A is a compound composed of an aryl group or a heteroaryl group, and Y1 and Y2 are linked via one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom.
- X1, X2 represents a coupler connected through one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom, silicon atom, and L1, L2, And any one of L3 and L4 is bonded to each other and connected via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom.
- each of L5 and L6, and L7 and L8 is bonded to each other and selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- R1 to R16 each represents a coupler connected via one atom selected from the group consisting of independent hydrogen atoms or substituents other than hydrogen atoms. .
- An electronic device is an electronic device including a compound represented by the following chemical formula (1).
- A is a compound composed of an aryl group or a heteroaryl group, and Y1 and Y2 are linked via one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom.
- X1, X2 represents a coupler connected through one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom, silicon atom, and L1, L2, And any one of L3 and L4 is bonded to each other and connected via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom.
- each of L5 and L6, and L7 and L8 is bonded to each other and selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- R1 to R16 each represents a coupler connected via one atom selected from the group consisting of independent hydrogen atoms or substituents other than hydrogen atoms. .
- a solid-state imaging device including a photoelectric conversion film that can perform photoelectric conversion with high selectivity with respect to light of a specific wavelength and high photoelectric conversion efficiency and has heat resistance is realized. It becomes possible.
- FIG. 1A is an explanatory diagram illustrating a solid-state imaging device including a photoelectric conversion element of the present technology
- FIG. 1B is an explanatory diagram illustrating a solid-state imaging device according to a comparative example.
- absorbing light of a certain wavelength means absorbing about 70% or more of light of that wavelength.
- transmitting light of a certain wavelength or “not absorbing light of a certain wavelength” means transmitting about 70% or more of light of that wavelength and absorbing less than about 30%. Represents.
- the solid-state imaging device 5 according to the comparative example includes photodiodes 7R, 7G, and 7B, and color filters 6R, 6G, and 6B formed on the photodiodes 7R, 7G, and 7B. Is provided.
- the color filters 6R, 6G, and 6B are films that selectively transmit light having a specific wavelength.
- the color filter 6R selectively transmits red light 2R having a wavelength of 600 nm or more
- the color filter 6G selectively transmits green light 2G having a wavelength of 450 nm or more and less than 600 nm
- the color filter 6B is 400 nm.
- the blue light 2B having a wavelength of less than 450 nm is selectively transmitted.
- the photodiodes 7R, 7G, and 7B are photodetectors that absorb light in a wide wavelength band (for example, the absorption wavelength of a silicon photodiode is 190 nm to 1100 nm). Therefore, it has been difficult to individually extract signals of each color such as red, green, and blue with the photodiodes 7R, 7G, and 7B alone.
- the color filters 6R, 6G, and 6B absorb light other than the light corresponding to each color and perform color separation by selectively transmitting only the light corresponding to each color.
- the signals of each color are taken out by 7R, 7G, and 7B.
- the solid-state imaging device 5 according to the comparative example has a limit in improving the detection sensitivity of each color.
- the solid-state imaging device 1 including the photoelectric conversion device of the present technology will be described.
- the solid-state image sensor 1 containing the photoelectric conversion element of this technique has the green photoelectric conversion element 3G which absorbs green light 2G, the blue photoelectric conversion element 3B which absorbs blue light 2B, and , And a red photoelectric conversion element 3R that absorbs red light 2R are sequentially stacked.
- the green photoelectric conversion element 3G is a photoelectric conversion element that selectively absorbs green light with a wavelength of 450 nm or more and less than 600 nm
- the blue photoelectric conversion element 3B selectively selects blue light with a wavelength of 400 nm or more and less than 450 nm
- the red photoelectric conversion element 3R is a photoelectric conversion element that selectively absorbs red light having a wavelength of 600 nm or more.
- each photoelectric conversion device can selectively absorb light in a specific wavelength band corresponding to red, green, and blue. Therefore, the solid-state imaging device 1 of the present technology does not require a color filter for separating incident light into each color, and can use all incident light for photoelectric conversion. Therefore, since the solid-state imaging device 1 of the present technology can increase the light that can be used for photoelectric conversion about three times that of the solid-state imaging device 5 according to the comparative example, the detection sensitivity of each color can be further improved. Can do.
- the blue photoelectric conversion device 3B and the red photoelectric conversion device 3R are silicon photodiodes that photoelectrically convert light in a wide wavelength band (specifically, 190 nm to 1100 nm, etc.). Also good.
- the blue photoelectric conversion element 3 ⁇ / b> B and the red photoelectric conversion element 3 ⁇ / b> R color-separate the blue light 2 ⁇ / b> B and the red light 2 ⁇ / b> R using the difference in the light penetration depth for each wavelength with respect to the solid-state imaging device 1.
- the red light 2R has a wavelength longer than that of the blue light 2B and is not easily scattered, and enters the depth away from the incident surface.
- the blue light 2B has a shorter wavelength than the red light 2R and is likely to be scattered. Therefore, it only enters to a depth closer to the incident surface. Therefore, by arranging the red photoelectric conversion element 3R at a position away from the incident surface of the solid-state imaging element 1, the red light 2R can be detected separately from the blue light 2R. Therefore, even when silicon photodiodes are used for the blue photoelectric conversion element 3B and the red photoelectric conversion element 3R, the blue light 2B and the red light 2R are separated using the difference in the light penetration depth, and signals of each color are extracted. Can do.
- the photoelectric conversion elements 3G, 3B, and 3R included in the solid-state imaging device 1 of the present technology selectively absorb light in specific wavelength bands corresponding to red, green, and blue, respectively, and other than the absorption wavelength It is required to transmit light having a wavelength.
- the green photoelectric conversion element 3G closest to the incident surface has an absorption spectrum having a steep peak in the green band (for example, a wavelength band of 450 nm to 600 nm), and has a small absorption in a band of 450 nm or less and less than 600 nm. Desired.
- FIG. 2 is a schematic diagram illustrating a configuration of a photoelectric conversion element according to an embodiment of the present technology.
- the photoelectric conversion element 101 includes a substrate 102, a lower electrode 104 disposed on the substrate 102, an electronic block layer 106 disposed on the lower electrode 104, A photoelectric conversion layer 108 disposed on the electron blocking layer 106, a hole blocking layer 110 disposed on the photoelectric conversion layer 108, and an upper electrode 112 disposed on the hole blocking layer 110 are provided.
- the structure of the photoelectric conversion element 101 illustrated in FIG. 2 is merely an example, and the structure of the photoelectric conversion element 101 according to an embodiment of the present technology is not limited to the structure illustrated in FIG. .
- the electron blocking layer 106 and the hole blocking layer 110 may be omitted.
- the substrate 102 is a support on which the layers constituting the photoelectric conversion element 101 are stacked.
- a substrate used in a general photoelectric conversion element can be used.
- the substrate 102 include various glass substrates such as a high strain point glass substrate, a soda glass substrate, and a borosilicate glass substrate, a quartz substrate, a semiconductor substrate, a plastic substrate such as polymethyl methacrylate, polyvinyl alcohol, polyimide, and polycarbonate. It may be.
- the substrate 102 is preferably formed of a transparent material.
- the lower electrode 104 and the upper electrode 112 are made of a conductive material, and at least one of them is made of a transparent conductive material.
- the lower electrode 104 and the upper electrode 112 may be formed of indium tin oxide (ITO), indium zinc oxide (IZO), or the like.
- ITO indium tin oxide
- IZO indium zinc oxide
- the lower electrode 104 and the upper electrode 112 are both made of a transparent conductive material such as ITO. It is preferable.
- a bias voltage is applied to the lower electrode 104 and the upper electrode 112.
- the polarity of the bias voltage is set so that electrons move to the upper electrode 112 and holes move to the lower electrode 104 among the charges generated in the photoelectric conversion layer 108.
- the polarity of the bias voltage may be set so that holes move to the upper electrode 112 and electrons move to the lower electrode 104 among the charges generated in the photoelectric conversion layer 108.
- the positions of the electron blocking layer 106 and the hole blocking layer 110 are switched.
- the electron blocking layer 106 suppresses an increase in dark current due to injection of electrons from the lower electrode 104 into the photoelectric conversion layer 108 when a bias voltage is applied.
- the electron blocking layer 106 is made of an electron donating material, such as arylamine, oxazole, oxadiazole, triazole, imidazole, stilbene, polyarylalkane, porphyrin, anthracene, fluorenone, hydrazone, or these. It may be composed of a derivative or the like.
- the electron blocking layer 106 includes N, N′-bis (3-methylphenyl)-(1,1′-biphenyl) -4,4′-diamine (TPD), 4,4′-bis [ N- (naphthyl) -N-phenyl-amino] biphenyl ( ⁇ -NPD), 4,4 ′, 4 ′′ -tris (N- (3-methylphenyl) N-phenylamino) triphenylamine (m-MTDATA) , Tetraphenylporphyrin copper, phthalocyanine, copper phthalocyanine, and the like.
- TPD N, N′-bis (3-methylphenyl)-(1,1′-biphenyl) -4,4′-diamine
- ⁇ -NPD 4,4′-bis [ N- (naphthyl) -N-phenyl-amino] biphenyl
- m-MTDATA 4,4 ′, 4 ′′ -tris (
- the photoelectric conversion layer 108 selectively absorbs light of a specific wavelength and photoelectrically converts the absorbed light.
- the photoelectric conversion layer 108 is configured by a photoelectric conversion film made of only a compound represented by the following chemical formula (1).
- a in the chemical formula (1) may be a compound having any structure represented by the following chemical formulas (2) to (8), and is an aryl group or a heteroaryl group,
- the molecular weight is preferably 75 or more, and the total molecular weight of the compound represented by the chemical formula (1) is preferably 620 or more and 1000 or less.
- B in the chemical formula (3) is different from A in the chemical formula (1), and each represents a carbon atom or a nitrogen atom.
- R21 in the chemical formula (6) is an aryl group or a heteroaryl group.
- Y1 and Y2 in the chemical formula (1) represent a coupler connected through one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom.
- X1 and X2 in the chemical formula (1) represent a coupler connected through one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom, and silicon atom.
- any one of L1 and L2, and L3 and L4 in the chemical formula (1) is selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom by bonding to each other.
- any one of L5 and L6 and L7 and L8 in the chemical formula (1) is bonded to each other and selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom and a silicon atom.
- R1 to R16 in the chemical formula (1) each represent a coupler connected through one atom selected from the group consisting of independent hydrogen atoms or substituents other than hydrogen atoms.
- the photoelectric conversion layer 108 can selectively absorb green light (for example, light having a wavelength of 450 nm or more and less than 600 nm).
- green light for example, light having a wavelength of 450 nm or more and less than 600 nm.
- a and R1 to R16 in the chemical formula (1) have no alkyl group.
- chemical formula (1) can also be represented by the following chemical formula (9), for example, depending on the configuration of A.
- Ax may be the same as, for example, the chemical formula (3) described above.
- R1 to R24 each represent a coupler that is linked via one independent hydrogen atom or one atom selected from the group consisting of carbon atoms.
- the hole blocking layer 110 suppresses an increase in dark current due to injection of holes from the upper electrode 112 into the photoelectric conversion layer 108 when a bias voltage is applied.
- the hole blocking layer 110 is made of an electron-accepting material such as fullerene, carbon nanotube, oxadiazole, triazole compound, anthraquinodimethane, diphenylquinone, distyrylarylene, silole compound, or these. Or a derivative thereof.
- the hole blocking layer 110 includes 1,3-bis (4-tert-butylphenyl-1,3,4-oxadiazolyl) phenylene (OXD-7), bathocuproine, bathophenanthroline, tris (8-hydroxy (Quinolinato) aluminum (Alq3) or the like.
- the material for forming each layer excluding the photoelectric conversion layer 108 is not particularly limited, and a known material for a photoelectric conversion element is used. It is also possible to do.
- each layer of the photoelectric conversion element 101 according to the embodiment of the present technology described above can be formed by selecting an appropriate film formation method according to the material, such as vacuum deposition, sputtering, or various coating methods. it can.
- the lower electrode 104 and the upper electrode 112 are vapor depositions including, for example, an electron beam vapor deposition method, a hot filament vapor deposition method, and a vacuum vapor deposition method.
- vapor depositions including, for example, an electron beam vapor deposition method, a hot filament vapor deposition method, and a vacuum vapor deposition method.
- Sputtering chemical vapor deposition (CVD)
- combination of ion plating and etching various printing methods such as screen printing, ink jet printing, and metal mask printing
- plating (electroplating) For example, an electroless plating method).
- the electron block layer 106, the photoelectric conversion layer 108, the hole block layer 110, and the like are, for example, a vapor deposition method such as a vacuum vapor deposition method, It can be formed by a printing method such as a screen printing method and an ink jet printing method, a laser transfer method, a coating method such as a spin coating method, or the like.
- the photoelectric conversion layer 108 of the photoelectric conversion element 101 in the solid-state imaging device to which the present technology is applied is configured by the compound of the chemical formula (1) described above.
- the compounds 1 to 9 shown in FIG. 3 will be described.
- the compounds 1 to 9 are compounds represented by the following chemical formulas (10) to (18).
- Compound X is subphthalocyanine chloride, which is a compound represented by the following chemical formula (19).
- ⁇ max absorption peak wavelength
- EQE photoelectric conversion efficiency
- each of the compounds 1 to 9 is a bulk hetero layer as a photoelectric conversion film constituting the photoelectric conversion layer 108, so that the photoelectric conversion efficiency (EQE) is higher than that of the photoelectric conversion layer formed only of the compound X. improves.
- EQE photoelectric conversion efficiency
- the material of the photoelectric conversion film constituting the photoelectric conversion layer 108 is spectroscopic. About a characteristic, a photoelectric conversion characteristic, and heat resistance, it can be said that it is the most suitable thing among seven types of compounds in FIG.
- a photoelectric converting film which comprises the photoelectric converting layer 108 if it is a compound corresponding to Chemical formula (1) mentioned above, by making it a bulk hetero layer, a photoelectric conversion efficiency improves, Specifically, for example, in addition to the compounds 1 to 9 shown in FIG. 3, the compounds 11 to 18 shown in FIG. 4 may be used.
- Compounds 11 to 18 are compounds represented by the following chemical formulas (20) to (27), respectively.
- compounds 1, 4, 11, 17, and 18 are optimized linkers for compound 5, compounds 6 and 12 are heterogeneous to compound 5, and compounds 8 and 9 are compounds. 5 linkers + hetero. Further, compounds 7, 13, and 14 are different in the number of side chains connected to A of compound 5, and compounds 15 and 16 are examples of different arrangements connected to A of compound 5. is there.
- a compound that aggregates is a case where there is no linker or the linker is not an aryl group or a heteroaryl group.
- the compound represented by the chemical formula (1) has a molecular weight of about 620 or less. That is, when there is a linker and the linker is an aryl group or a heteroaryl group, the film quality is not changed by annealing. Therefore, the molecular weight of the compound represented by the chemical formula (1) is desirably larger than about 620.
- the compound represented by the chemical formula (1) will cause material decomposition of the oxygen-crosslinked triallylamine site during vapor deposition when not heated carefully.
- the heat load during vapor deposition generally increases as the molecular weight increases, a compound having a molecular weight exceeding 1000 and the linker being an aryl group or heteroaryl group is accompanied by material decomposition during film formation by vapor deposition. Therefore, the molecular weight of the compound represented by the chemical formula (1) is preferably smaller than 1000.
- the compound of the chemical formula (1) may be applied to the buffer layer constituting the electron blocking layer 106.
- the compound of the chemical formula (1) can be applied to both the electron block layer 106 and the photoelectric conversion layer 108, and by using it as the electron block layer 106, dark current is reduced while maintaining transparency. It is possible to improve spectral characteristics and photoelectric conversion characteristics by using the photoelectric conversion layer 108.
- a P-type semiconductor material having an energy level in the range of 5.3 to 5.8 eV is often used to transport holes.
- transparent electrodes formed using a transparent conductive material formed above and below the green photoelectric conversion element generally have a work function in the range of 4.5 to 5.2 eV.
- the electron block layer 106 described with reference to FIG. 2 contains a compound represented by the chemical formula (1), and this electron block layer 106 has an energy level in the range of 5.2 to 5.7 eV.
- the electron blocking layer 106 having the same value as the energy level of the green photoelectric conversion film and the work function of the transparent electrode, or one of them.
- the photoelectric conversion efficiency (EQE) is achieved while expressing the effect of reducing dark current by introducing an electron blocking layer, which is generally said.
- an important characteristic of the solid-state imaging device such as photoresponsiveness is not impaired.
- a photoelectric conversion film that absorbs green light is often provided with a hole mobility in the range of 1 ⁇ 10 ⁇ 3 to 1 ⁇ 10 ⁇ 6 cm 2 / Vs in order to transport holes.
- the electron blocking layer 106 described with reference to FIG. 2 contains a compound represented by the chemical formula (1), and this hole mobility is in the range of 1 ⁇ 10 ⁇ 2 to 1 ⁇ 10 ⁇ 5 cm 2 / Vs. .
- the hole mobility of the green photoelectric conversion film and the hole mobility of the electron block layer 106 are the same, or the electron block layer 106 has a higher hole mobility.
- a layer can be provided.
- the photoelectric conversion efficiency (EQE) is achieved while expressing the effect of reducing dark current by introducing an electron blocking layer, which is generally said.
- an important characteristic of the solid-state imaging device such as photoresponsiveness is not impaired.
- This transparent electrode is often an inorganic oxide such as ITO or IZO.
- the electron blocking layer 106 described with reference to FIG. 2 includes a compound represented by the chemical formula (1), and these include oxygen atoms in the skeleton.
- This oxygen atom is expected to interact with the transition metal exposed on the outermost surface of the inorganic oxide of the transparent electrode to form a good contact with the electrode.
- This oxygen atom is expected to replace the oxygen atom exposed on the outermost surface of the inorganic oxide of the transparent electrode and form a good contact with the electrode.
- the photoelectric conversion efficiency (EQE) is achieved while expressing the effect of reducing dark current by introducing an electron blocking layer, which is generally said.
- an important characteristic of the solid-state imaging device such as photoresponsiveness is not impaired.
- anisotropy ⁇ In a solid-state imaging device using a photoelectric conversion film that absorbs green light, it is necessary to consider the carrier mobility in the vertical direction and the horizontal direction of the light-receiving surface of the formed organic photoelectric conversion film.
- the carrier mobility in the horizontal direction is higher than that in the vertical direction of the light receiving surface.
- the electron blocking layer 106 described with reference to FIG. 2 includes a compound represented by the chemical formula (1), which is expected to have higher carrier mobility in the horizontal direction of the light receiving surface than that in the vertical direction of the light receiving surface. Is done.
- One of the causes is the property of the electronic block layer 106 in FIG. 2 that it is easy to obtain horizontal orientation with respect to the substrate.
- FIG. 5 is a schematic diagram illustrating a structure of a solid-state imaging element to which the photoelectric conversion element of the present technology is applied.
- pixel areas 201, 211, and 231 are areas in which photoelectric conversion elements including a photoelectric conversion film of the present technology are arranged.
- the control circuits 202, 212, and 242 are arithmetic processing circuits that control each configuration of the solid-state imaging device, and the logic circuits 203, 223, and 243 process signals that are photoelectrically converted by the photoelectric conversion elements in the pixel region. This is a signal processing circuit.
- a solid-state imaging device to which the photoelectric conversion element of the present technology is applied includes a pixel region 201, a control circuit 202, and a logic circuit 203 in one semiconductor chip 200. It may be formed.
- the solid-state imaging device to which the photoelectric conversion element of the present technology is applied includes a pixel region 211 and a control circuit 212 formed in the first semiconductor chip 210, and the second A stacked solid-state imaging device in which a logic circuit 223 is formed in the semiconductor chip 220 may be used.
- the solid-state imaging device to which the photoelectric conversion element of the present technology is applied has a pixel region 231 formed in the first semiconductor chip 230 and is controlled in the second semiconductor chip 240.
- a multilayer solid-state imaging device in which the circuit 242 and the logic circuit 243 are formed may be used.
- the solid-state imaging device shown by configurations B and C in FIG. 5 at least one of the control circuit and the logic circuit is formed in a semiconductor chip different from the semiconductor chip in which the pixel region is formed. Therefore, since the solid-state imaging device shown in the configurations B and C in FIG. 5 can expand the pixel area more than the solid-state imaging device shown in the configuration A in FIG. 5, the number of pixels mounted in the pixel region is increased. The planar resolution can be improved. Therefore, the solid-state imaging device to which the photoelectric conversion element of the present technology is applied is more preferably the stacked solid-state imaging device shown in the configurations B and C of FIG.
- FIG. 6 is a cross-sectional view schematically illustrating a unit pixel of a solid-state imaging element to which the photoelectric conversion element of the present technology is applied.
- the solid-state imaging device 300 illustrated in FIG. 6 is a back-illuminated solid-state imaging device in which light enters from a surface opposite to the surface on which the pixel transistors and the like are formed.
- the upper side of the drawing is a light receiving surface
- the lower side is a circuit forming surface on which pixel transistors and peripheral circuits are formed.
- the solid-state imaging device 300 includes a photoelectric conversion element including a first photodiode PD1 formed on the semiconductor substrate 330 and a second photodiode PD2 formed on the semiconductor substrate 330 in the photoelectric conversion region 320. And a photoelectric conversion element including the organic photoelectric conversion film 310 formed on the back surface side of the semiconductor substrate 330 is stacked in the light incident direction.
- the first photodiode PD1 and the second photodiode PD2 are formed in a well region 331 that is a first conductivity type (for example, p-type) semiconductor region of a semiconductor substrate 330 made of silicon.
- the first photodiode PD1 has an n-type semiconductor region 332 formed of a second conductivity type (for example, n-type) impurity formed on the light receiving surface side of the semiconductor substrate 330 and a part thereof reaching the surface side of the semiconductor substrate 330. And an extension portion 332a formed to extend in the direction. A high-concentration p-type semiconductor region 334 serving as a charge storage layer is formed on the surface of the extension 332a.
- the extension 332a is formed as an extraction layer for extracting signal charges accumulated in the n-type semiconductor region 332 of the first photodiode PD1 to the surface side of the semiconductor substrate 330.
- the second photodiode PD2 includes an n-type semiconductor region 336 formed on the light receiving surface side of the semiconductor substrate 330, a high-concentration p-type semiconductor region 338 formed on the surface side of the semiconductor substrate 330 and serving as a charge storage layer, Consists of.
- the first photodiode PD1 and the second photodiode PD2 by forming a p-type semiconductor region at the interface of the semiconductor substrate 330, dark current generated at the interface of the semiconductor substrate 330 can be suppressed.
- the second photodiode PD2 formed in the region farthest from the light receiving surface is, for example, a red photoelectric conversion element that absorbs red light and performs photoelectric conversion.
- the first photodiode PD1 formed on the light receiving surface side of the second photodiode PD2 is, for example, a blue photoelectric conversion element that absorbs blue light and performs photoelectric conversion.
- the organic photoelectric conversion film 310 is formed on the back surface of the semiconductor substrate 330 with the antireflection film 302 and the insulating film 306 interposed therebetween.
- the organic photoelectric conversion film 310 is sandwiched between the upper electrode 312 and the lower electrode 308 to form a photoelectric conversion element.
- the organic photoelectric conversion film 310 is, for example, an organic film that absorbs green light and performs photoelectric conversion, and is formed of the photoelectric conversion film of the present technology described above.
- the upper electrode 312 and the lower electrode 308 are formed of a transparent conductive material such as indium tin oxide (ITO) or indium zinc oxide (IZO).
- the lower electrode 308 is connected to a vertical transfer path 348 formed from the back surface side to the front surface side of the semiconductor substrate 330 via a contact plug 304 that penetrates the antireflection film 302.
- the vertical transfer path 348 is formed from a back surface side of the semiconductor substrate 330 with a stacked structure of a connection portion 340, a potential barrier layer 342, a charge storage layer 344 and a p-type semiconductor region 346.
- connection portion 340 is formed of an n-type impurity region having a high impurity concentration formed on the back surface side of the semiconductor substrate 330, and is formed for ohmic contact with the contact plug 304.
- the potential barrier layer 342 is made of a low-concentration p-type impurity region, and forms a potential barrier between the connection portion 340 and the charge storage layer 344.
- the charge storage layer 344 stores the signal charge transferred from the organic photoelectric conversion film 310 and is formed of an n-type impurity region having a lower concentration than the connection portion 340.
- a high-concentration p-type semiconductor region 346 is formed on the surface of the semiconductor substrate 330. Such p-type semiconductor region 346 suppresses dark current generated at the interface of the semiconductor substrate 330.
- a multilayer wiring layer 350 including wirings 358 stacked in a plurality of layers via an interlayer insulating layer 351 is formed on the surface side of the semiconductor substrate 330.
- readout circuits 352, 354, and 356 corresponding to the first photodiode PD1, the second photodiode PD2, and the organic photoelectric conversion film 310 are formed in the vicinity of the surface of the semiconductor substrate 330.
- the read circuits 352, 354, and 356 read output signals from the respective photoelectric conversion elements and transfer them to a logic circuit (not shown).
- a support substrate 360 is formed on the surface of the multilayer wiring layer 350.
- a light shielding film 316 is formed on the light receiving surface side of the upper electrode 312 so as to shield the extension 332a of the first photodiode PD1 and the vertical transfer path 348.
- a region divided by the light shielding films 316 is a photoelectric conversion region 320.
- An on-chip lens 318 is formed on the light shielding film 316 with a planarizing film 314 interposed therebetween.
- the solid-state imaging device 300 to which the photoelectric conversion device of the present technology is applied has been described above.
- color separation or the like is not formed in the unit pixel because color separation is performed in the vertical direction.
- FIG. 7 is a block diagram illustrating a configuration of an electronic device to which the photoelectric conversion element of the present technology is applied.
- the electronic apparatus 400 includes an optical system 402, a solid-state imaging device 404, a DSP (Digital SignalssProcessor) circuit 406, a control unit 408, an output unit 412, an input unit 414, and a frame memory. 416, a recording unit 418, and a power supply unit 420.
- DSP Digital SignalssProcessor
- the DSP circuit 406, the control unit 408, the output unit 412, the input unit 414, the frame memory 416, the recording unit 418, and the power supply unit 420 are connected to each other via the bus line 410.
- the optical system 402 takes in incident light from a subject and forms an image on the imaging surface of the solid-state imaging device 404.
- the solid-state imaging device 404 includes a photoelectric conversion device of the present technology, converts the amount of incident light imaged on the imaging surface by the optical system 402 into an electrical signal in units of pixels, and outputs the electrical signal.
- the DSP circuit 406 processes the pixel signal transferred from the solid-state image sensor 404 and outputs it to the output unit 412, the frame memory 416, the recording unit 418, and the like.
- the control unit 408 includes, for example, an arithmetic processing circuit and the like, and controls the operation of each component of the electronic device 400.
- the output unit 412 is a panel type display device such as a liquid crystal display or an organic electroluminescence display, and displays a moving image or a still image captured by the solid-state imaging device 404. Note that the output unit 412 may include an audio output device such as a speaker and headphones.
- the input unit 414 is a device for a user to input an operation, such as a touch panel or a button, and issues operation commands for various functions of the electronic device 400 according to the user's operation.
- the frame memory 416 temporarily stores a moving image or a still image captured by the solid-state imaging device 404.
- the recording unit 418 records a moving image or a still image captured by the solid-state imaging device 404 on a removable storage medium such as a magnetic disk, an optical disk, a magneto-optical disk, or a semiconductor memory.
- the power source unit 420 appropriately supplies various power sources serving as operation power sources for the DSP circuit 406, the control unit 408, the output unit 412, the input unit 414, the frame memory 416, and the recording unit 418 to these supply targets.
- the electronic device 400 to which the photoelectric conversion element of the present technology is applied has been described above.
- the electronic device 400 to which the photoelectric conversion element of the present technology is applied may be, for example, an imaging device.
- a solid-state imaging device containing a compound represented by the following chemical formula (1) A is a compound consisting of an aryl group or a heteroaryl group, Y1 and Y2 represent a coupler that is connected through one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom; X1 and X2 each represent a coupler that is connected via one atom selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom; Each of L1 and L2, and L3 and L4 is bonded to each other and linked via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom Represents a coupler Each of L5 and L6, and L7 and L8 is
- the solid-state imaging device according to ⁇ 1>, wherein A has a molecular weight greater than 75.
- ⁇ 3> The solid-state imaging device according to ⁇ 1> or ⁇ 2>, wherein the compound represented by the chemical formula (1) has a molecular weight greater than 620.
- ⁇ 4> The solid-state imaging device according to any one of ⁇ 1> to ⁇ 3>, wherein the compound represented by the chemical formula (1) has a molecular weight of less than 1000.
- the A includes compounds of the following chemical formulas (3) to (6), B in the chemical formula (3) is different from A in the chemical formula (1), and each represents a carbon atom or a nitrogen atom.
- R21 in the chemical formula (6) is an aryl group or a heteroaryl group.
- the compound represented by the chemical formula (1) includes a compound of the following chemical formula (9), Ax in the chemical formula (9) is represented by the following chemical formula (3):
- A is a compound consisting of an aryl group or a heteroaryl group
- Y1 and Y2 represent a coupler that is connected through one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom
- X1 and X2 each represent a coupler that is connected via one atom selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- Each of L1 and L2, and L3 and L4 is bonded to each other and linked via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom
- Each of L5 and L6, and L7 and L8 is bonded to each other and linked via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom,
- A is a compound consisting of an aryl group or a heteroaryl group
- Y1 and Y2 represent a coupler that is connected through one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom
- X1 and X2 each represent a coupler that is connected via one atom selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- Each of L1 and L2, and L3 and L4 is bonded to each other and linked via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom
- Each of L5 and L6, and L7 and L8 is bonded to each other and linked via one atom selected from the group
- A is a compound consisting of an aryl group or a heteroaryl group
- Y1 and Y2 represent a coupler that is connected through one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom
- X1 and X2 each represent a coupler that is connected via one atom selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- Each of L1 and L2, and L3 and L4 is bonded to each other and linked via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom
- Each of L5 and L6, and L7 and L8 is bonded to each other and linked via one atom selected from the group consisting
- A is a compound consisting of an aryl group or a heteroaryl group
- Y1 and Y2 represent a coupler that is connected through one atom selected from the group consisting of a nitrogen atom, a boron atom, and a phosphorus atom
- X1 and X2 each represent a coupler that is connected via one atom selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom, and a silicon atom
- Each of L1 and L2, and L3 and L4 is bonded to each other and linked via one atom selected from the group consisting of oxygen atom, sulfur atom, carbon atom, nitrogen atom, phosphorus atom and silicon atom
- Each of L5 and L6, and L7 and L8 is bonded to each other and linked via one atom selected from the group consisting
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electromagnetism (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Solid State Image Pick-Up Elements (AREA)
- Light Receiving Elements (AREA)
Abstract
Description
図1を参照して、本技術の光電変換素子の概略について説明する。図1の(A)は、本技術の光電変換素子を含む固体撮像素子を説明する説明図であり、図1の(B)は、比較例に係る固体撮像素子を説明する説明図である。
次に、図2を参照して、本技術の一実施の形態に係る光電変換素子の構成について説明する。図2は、本技術の一実施の形態に係る光電変換素子の構成を示す概略図である。
本技術を適用した固体撮像素子における光電変換素子101の光電変換層108は、上述した化学式(1)の化合物により構成される。このうち、例えば、図3で示される化合物1乃至9について説明する。この化合物1乃至9は、以下の化学式(10)乃至化学式(18)で表される化合物である。
以上においては、光電変換層108の光電変換膜として、上述の化学式(1)の化合物を使用する例について説明してきたが、化学式(1)の化合物は、透明性を保ちつつ耐熱性を備えており、さらに、暗電流を低減させることがわかっている。
さらに、化学式(1)の化合物を電子ブロック層106に適用する場合、緑色光電変換膜として使用することで高い効果を得ることができる。以下に、化学式(1)の化合物を電子ブロック層106に適用する場合、緑色光電変換膜として適用することで高い効果が得られる理由について説明する。
緑色光を吸収する光電変換膜では、一般的に、ホールを輸送するために5.3乃至5.8eVの範囲のエネルギー凖位を持つP型半導体材料が用いられることが多い。
緑色光を吸収する光電変換膜では、一般的に、ホールを輸送するために1×10-3乃至1×10-6cm2/Vsの範囲のホール移動度が設けられることが多い。
緑色光を吸収する光電変換膜を用いた固体撮像素子においては、緑色光電変換膜の上下に透明電極を形成する。
緑色光を吸収する光電変換膜を用いた固体撮像素子では、形成された有機光電変換膜の、受光面垂直方向と水平方向のキャリア移動度を考慮する必要がある。
次に、図5および6を参照して、本技術の光電変換素子が適用される固体撮像素子の構成について説明する。図5は、本技術の光電変換素子が適用される固体撮像素子の構造を示す概略図である。
続いて、図7を参照して、本技術の光電変換素子が適用される電子機器の構成について説明する。図7は、本技術の光電変換素子が適用される電子機器の構成を説明するブロック図である。
<1> 下記化学式(1)で表される化合物を含む固体撮像素子。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。
<2> 前記Aは、分子量が75より大きい
<1>に記載の固体撮像素子。
<3> 前記化学式(1)で表される化合物は分子量が620より大きい
<1>または<2>に記載の固体撮像素子。
<4> 前記化学式(1)で表される化合物は分子量が1000より小さい
<1>乃至<3>のいずれかに記載の固体撮像素子。
<5> 前記Aは以下の化学式(3)乃至化学式(6)の化合物を含み、
前記化学式(4)におけるnは、n=1乃至5であり、
前記化学式(6)のR21は、アリール基、または、ヘテロアリール基である
<1>乃至<4>のいずれかに記載の固体撮像素子。
<6> 前記化学式(1)で表される化合物は、以下の化学式(9)の化合物を含み、
<1>に記載の固体撮像素子。
<7> 一対の電極の間に積層されるいずれかの層が、前記化学式(1)の化合物より構成される
<1>乃至<6>のいずれかに記載の固体撮像素子。
<8> 前記一対の電極の間に、
入射光を光電変換する光電変換層と、
前記光電変換層に対して電子をブロッキングする電子ブロッキング層とをさらに含み、
前記電子ブロッキング層が、前記化学式(1)の化合物より構成される
<7>に記載の固体撮像素子。
<9> 前記光電変換層は、緑色光を光電変換する
<8>に記載の固体撮像素子。
<10> 下記化学式(1)で表される化合物を含む光電変換膜。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。
<11> 下記化学式(1)で表される化合物を含む電子ブロック層。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。
<12> 下記化学式(1)で表される化合物を含む撮像装置。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。
<13> 下記化学式(1)で表される化合物を含む電子機器。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。
Claims (13)
- 下記化学式(1)で表される化合物を含む固体撮像素子。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。 - 前記Aは、分子量が75より大きい
請求項1に記載の固体撮像素子。 - 前記化学式(1)で表される化合物は分子量が620より大きい
請求項1に記載の固体撮像素子。 - 前記化学式(1)で表される化合物は分子量が1000より小さい
請求項1に記載の固体撮像素子。 - 一対の電極の間に積層されるいずれかの層が、前記化学式(1)の化合物より構成される
請求項1に記載の固体撮像素子。 - 前記一対の電極の間に、
入射光を光電変換する光電変換層と、
前記光電変換層に対して電子をブロッキングする電子ブロッキング層とをさらに含み、
前記電子ブロッキング層が、前記化学式(1)の化合物より構成される
請求項7に記載の固体撮像素子。 - 前記光電変換層は、緑色光を光電変換する
請求項8に記載の固体撮像素子。 - 下記化学式(1)で表される化合物を含む光電変換膜。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。 - 下記化学式(1)で表される化合物を含む電子ブロック層。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。 - 下記化学式(1)で表される化合物を含む撮像装置。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。 - 下記化学式(1)で表される化合物を含む電子機器。
Aは、アリール基、またはヘテロアリール基からなる化合物であり、
Y1、Y2は窒素原子、ホウ素原子、リン原子からなる群より選択される1つの原子を介して連結する連結器を表し、
X1、X2は酸素原子、硫黄原子、炭素原子、窒素原子、りん原子、ケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L1およびL2、並びにL3およびL4のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
L5およびL6、並びにL7およびL8のそれぞれのいずれか一方は互いに結合して酸素原子、硫黄原子、炭素原子、窒素原子、リン原子およびケイ素原子からなる群より選択される1つの原子を介して連結する連結器を表し、
R1乃至R16は、それぞれ独立した水素原子、または、水素原子以外の置換基からなる群より選択される1つの原子を介して連結する連結器を表す。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/577,319 US11088207B2 (en) | 2015-06-05 | 2016-05-25 | Solid-state image sensor, photoelectric conversion film, electron blocking layer, imaging apparatus, and electronic device |
CN201680030989.8A CN107636830B (zh) | 2015-06-05 | 2016-05-25 | 固态成像元件、光电转换膜、电子阻挡层、摄像装置及电子设备 |
KR1020177033778A KR102607472B1 (ko) | 2015-06-05 | 2016-05-25 | 고체 촬상 소자, 광전 변환막, 전자 블록층, 촬상 장치 및 전자 기기 |
JP2017521848A JP6749900B2 (ja) | 2015-06-05 | 2016-05-25 | 固体撮像素子、光電変換膜、電子ブロック層、撮像装置、および電子機器 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015114526 | 2015-06-05 | ||
JP2015-114526 | 2015-06-05 | ||
JP2016098292 | 2016-05-16 | ||
JP2016-098292 | 2016-05-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2016194717A1 true WO2016194717A1 (ja) | 2016-12-08 |
Family
ID=57442389
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2016/065386 WO2016194717A1 (ja) | 2015-06-05 | 2016-05-25 | 固体撮像素子、光電変換膜、電子ブロック層、撮像装置、および電子機器 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11088207B2 (ja) |
JP (1) | JP6749900B2 (ja) |
KR (1) | KR102607472B1 (ja) |
CN (1) | CN107636830B (ja) |
WO (1) | WO2016194717A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018155275A1 (ja) * | 2017-02-21 | 2018-08-30 | 東ソー株式会社 | 酸素架橋型トリアリールアミン化合物及びその前駆体ならびに発光材料 |
JP2019069932A (ja) * | 2017-02-21 | 2019-05-09 | 東ソー株式会社 | 酸素架橋型トリアリールアミン化合物及びその前駆体ならびに発光材料 |
CN110573515A (zh) * | 2017-04-25 | 2019-12-13 | 默克专利有限公司 | 用于电子器件的化合物 |
US10566547B2 (en) | 2016-07-11 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2020174972A1 (ja) * | 2019-02-27 | 2020-09-03 | 株式会社カネカ | 光電変換素子および光電変換素子の製造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7007088B2 (ja) * | 2016-12-07 | 2022-01-24 | ソニーセミコンダクタソリューションズ株式会社 | 受光素子、撮像素子および電子機器 |
JP2021044310A (ja) * | 2019-09-09 | 2021-03-18 | キヤノン株式会社 | 半導体装置 |
CN114133385B (zh) * | 2021-10-27 | 2023-05-23 | 华南师范大学 | 一种以咔唑为核心、以噻吩嗪或吩恶嗪为端基的空穴传输材料及其合成方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007335760A (ja) * | 2006-06-16 | 2007-12-27 | Fujifilm Corp | 光電変換膜、並びに、該光電変換膜を含む太陽電池、光電変換素子、又は撮像素子 |
JP2012116794A (ja) * | 2010-12-01 | 2012-06-21 | Canon Inc | キノリノ[3,2,1−kl]フェノキサジン化合物及びこれを用いた有機発光素子 |
JP2013118335A (ja) * | 2011-12-05 | 2013-06-13 | Sony Corp | 有機光電変換材料、光電変換素子、撮像装置、太陽電池 |
WO2014111365A1 (en) * | 2013-01-15 | 2014-07-24 | Basf Se | Triangulene oligomers and polymers and their use as hole conducting material |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5683823A (en) * | 1996-01-26 | 1997-11-04 | Eastman Kodak Company | White light-emitting organic electroluminescent devices |
EP1033731B1 (en) * | 1999-03-01 | 2006-07-05 | Fuji Photo Film Co., Ltd. | Photo-electrochemical cell containing an electrolyte comprising a liquid crystal compound |
JP2003234460A (ja) | 2002-02-12 | 2003-08-22 | Nippon Hoso Kyokai <Nhk> | 積層型光導電膜および固体撮像装置 |
JP2005303266A (ja) | 2004-03-19 | 2005-10-27 | Fuji Photo Film Co Ltd | 撮像素子、その電場印加方法および印加した素子 |
JP5460118B2 (ja) * | 2008-05-14 | 2014-04-02 | 富士フイルム株式会社 | 光電変換素子、及び撮像素子 |
TWI481954B (zh) * | 2009-06-10 | 2015-04-21 | Fujifilm Corp | 著色硬化組成物、彩色光阻、噴墨印墨、彩色濾光片及其製造方法、固態攝影裝置、影像顯示裝置、液晶顯示器、有機電致發光顯示器及著色劑化合物以及其互變異構物 |
KR20140013001A (ko) * | 2011-03-03 | 2014-02-04 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 신규 화합물, 전하 수송 재료 및 유기 디바이스 |
US9193727B2 (en) * | 2011-03-10 | 2015-11-24 | Cryscade Solar Limited | Organic compound and photovoltaic device comprising the same |
JP5814044B2 (ja) * | 2011-08-16 | 2015-11-17 | 富士フイルム株式会社 | 光電変換素子およびその使用方法、撮像素子、光センサ |
JP5780402B2 (ja) * | 2011-12-27 | 2015-09-16 | ソニー株式会社 | 半導体素子、半導体素子の製造方法、固体撮像装置および電子機器 |
US10336772B2 (en) * | 2015-12-28 | 2019-07-02 | Samsung Electronics Co., Ltd. | Bicarbazole compound, material for organic light-emitting device including bicarbazole compound, and organic light-emitting device including bicarbazole compound |
-
2016
- 2016-05-25 KR KR1020177033778A patent/KR102607472B1/ko active IP Right Grant
- 2016-05-25 WO PCT/JP2016/065386 patent/WO2016194717A1/ja active Application Filing
- 2016-05-25 JP JP2017521848A patent/JP6749900B2/ja active Active
- 2016-05-25 CN CN201680030989.8A patent/CN107636830B/zh active Active
- 2016-05-25 US US15/577,319 patent/US11088207B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007335760A (ja) * | 2006-06-16 | 2007-12-27 | Fujifilm Corp | 光電変換膜、並びに、該光電変換膜を含む太陽電池、光電変換素子、又は撮像素子 |
JP2012116794A (ja) * | 2010-12-01 | 2012-06-21 | Canon Inc | キノリノ[3,2,1−kl]フェノキサジン化合物及びこれを用いた有機発光素子 |
JP2013118335A (ja) * | 2011-12-05 | 2013-06-13 | Sony Corp | 有機光電変換材料、光電変換素子、撮像装置、太陽電池 |
WO2014111365A1 (en) * | 2013-01-15 | 2014-07-24 | Basf Se | Triangulene oligomers and polymers and their use as hole conducting material |
Non-Patent Citations (1)
Title |
---|
NISHIMURA, HIDETAKA; ET AL.: "Hole- Transporting Materials with a Two-Dimensionally Expanded n-System around an Azulene Core for Efficient Perovskite Solar Cells", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 137, no. 50, pages 15656 - 15659, XP055332301 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10566547B2 (en) | 2016-07-11 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680184B2 (en) | 2016-07-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2018155275A1 (ja) * | 2017-02-21 | 2018-08-30 | 東ソー株式会社 | 酸素架橋型トリアリールアミン化合物及びその前駆体ならびに発光材料 |
JP2019069932A (ja) * | 2017-02-21 | 2019-05-09 | 東ソー株式会社 | 酸素架橋型トリアリールアミン化合物及びその前駆体ならびに発光材料 |
JP7176195B2 (ja) | 2017-02-21 | 2022-11-22 | 東ソー株式会社 | 酸素架橋型トリアリールアミン化合物及びその前駆体ならびに発光材料 |
CN110573515A (zh) * | 2017-04-25 | 2019-12-13 | 默克专利有限公司 | 用于电子器件的化合物 |
US11649249B2 (en) | 2017-04-25 | 2023-05-16 | Merck Patent Gmbh | Compounds for electronic devices |
WO2020174972A1 (ja) * | 2019-02-27 | 2020-09-03 | 株式会社カネカ | 光電変換素子および光電変換素子の製造方法 |
JPWO2020174972A1 (ja) * | 2019-02-27 | 2021-12-02 | 株式会社カネカ | 光電変換素子および光電変換素子の製造方法 |
JP7244031B2 (ja) | 2019-02-27 | 2023-03-22 | 株式会社カネカ | 光電変換素子および光電変換素子の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20180015132A (ko) | 2018-02-12 |
CN107636830B (zh) | 2021-11-16 |
JP6749900B2 (ja) | 2020-09-02 |
JPWO2016194717A1 (ja) | 2018-03-22 |
CN107636830A (zh) | 2018-01-26 |
US20180151625A1 (en) | 2018-05-31 |
US11088207B2 (en) | 2021-08-10 |
KR102607472B1 (ko) | 2023-11-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6749900B2 (ja) | 固体撮像素子、光電変換膜、電子ブロック層、撮像装置、および電子機器 | |
CN107078216B (zh) | 光电转换膜、光电转换元件和电子设备 | |
JP6754156B2 (ja) | 固体撮像素子および固体撮像素子の製造方法、光電変換素子、撮像装置、電子機器、並びに光電変換素子。 | |
US11309498B2 (en) | Photoelectric conversion film, solid-state image sensor, and electronic device | |
US20220149304A1 (en) | Photoelectric conversion element, method of manufacturing the same, solid state image sensor, electronic device, and solar cell | |
JP2015103735A (ja) | 固体撮像素子および電子機器 | |
JP6659597B2 (ja) | 光電変換膜、固体撮像素子、および電子機器 | |
JP2012191222A (ja) | 光電変換素子の製造方法 | |
TW201704240A (zh) | 縮合多環芳香族化合物 | |
JP2022017302A (ja) | 固体撮像素子および電子機器 | |
JP2017073426A (ja) | 撮像素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16803152 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2017521848 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20177033778 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15577319 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 16803152 Country of ref document: EP Kind code of ref document: A1 |