JP5939573B2 - ドナー―π―アクセプター型化合物及び色素増感太陽電池用色素 - Google Patents
ドナー―π―アクセプター型化合物及び色素増感太陽電池用色素 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims description 48
- 229940126214 compound 3 Drugs 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000370 acceptor Substances 0.000 description 37
- 229910044991 metal oxide Inorganic materials 0.000 description 30
- 150000004706 metal oxides Chemical class 0.000 description 30
- 239000000975 dye Substances 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 125000000962 organic group Chemical group 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 18
- 238000001179 sorption measurement Methods 0.000 description 17
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000005556 thienylene group Chemical group 0.000 description 5
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 125000005551 pyridylene group Chemical group 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 238000004873 anchoring Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910021419 crystalline silicon Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- -1 furylene group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MXLZUALXSYVAIV-UHFFFAOYSA-N 1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C MXLZUALXSYVAIV-UHFFFAOYSA-N 0.000 description 1
- QPTWWBLGJZWRAV-UHFFFAOYSA-N 2,7-dibromo-9-H-carbazole Natural products BrC1=CC=C2C3=CC=C(Br)C=C3NC2=C1 QPTWWBLGJZWRAV-UHFFFAOYSA-N 0.000 description 1
- GZBJRMVGNVDUCO-UHFFFAOYSA-N 3,6-dibromo-9-ethylcarbazole Chemical compound BrC1=CC=C2N(CC)C3=CC=C(Br)C=C3C2=C1 GZBJRMVGNVDUCO-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 206010010947 Coordination abnormal Diseases 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- CQQKQXCFZKZFGU-UHFFFAOYSA-N S1C([Sn](CCCC)(CCCC)CCCC)=CC=C1C1=CC=NC=C1 Chemical compound S1C([Sn](CCCC)(CCCC)CCCC)=CC=C1C1=CC=NC=C1 CQQKQXCFZKZFGU-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 208000028756 lack of coordination Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
Landscapes
- Hybrid Cells (AREA)
- Plural Heterocyclic Compounds (AREA)
- Photovoltaic Devices (AREA)
Description
式31で表される、
(式31中、Dはアルキル基、nは0〜3の整数を表す。)
ことを特徴とする。
本発明の第一の観点に係るドナー―π―アクセプター型化合物を含有する、
ことを特徴とする。
本実施の形態に係るドナー−π−アクセプター型化合物(以下、D−π−A型化合物ともいう)は、金属酸化物への吸着能を有するアクセプターを一分子中に二つ有している。そして、図1に示すように、ドナー及びπを共有し、π共役構造が分岐していないドナー−π−アクセプター構造を二つ備えている。
本実施の形態に係る色素増感太陽電池用色素化合物は上述のD―π―A型化合物からなる。D―π―A型化合物においては、ドナー及びπを共有する二つのD−π−A構造であり、いずれのD−π−A構造においてもπ共役構造が構造上分岐しておらず直線状であるので、ドナーからアクセプター方向に効率よく電子が流れるとともに、アクセプター中の窒素により金属酸化物に容易且つ強固に吸着することができる。このため、D―π―A型化合物は色素増感太陽電池用色素化合物として好適に使用できる。
下記反応式に示すようにして化合物1を合成した。
反応溶液を乾燥後、ジクロロメタンと水で有機層を抽出した。カラムクロマトグラフィー(展開溶媒 ジクロロメタン:MeOH=4:1)、再沈殿(良溶媒:ジクロロメタン、貧溶媒:ヘキサン)、再結晶(良溶媒:ジクロロメタン、貧溶媒:ヘキサン)の順に精製を行った。
薄黄色の針状結晶80mg(収率16%)を得た。1HNMR、HRMSスペクトルより、化合物1であることを確認した。
1H-NMR スペクトル(500MHz) Acetone-d6 / TMS
σ=8.82(2H, d, J=1.9 Hz), σ=8.65(4H, dd, J1=4.4 Hz, J2=1.7 Hz), σ=7.95 (2H, dd, J1=8.6 Hz, J2=1.9 Hz),σ=7.82 Hz (4H, dd, J1=4.4 Hz, J2=1.7 Hz), σ=7.78 (2H, d, J=8.6 Hz), σ=4.61 (2H, q, J=7.20 Hz), σ=1.49 (3H, t, J=7.20 Hz)
HRMS スペクトル:HRMS(ESI) : m/z=350.1653 [M+H]+ ; calcd. For C24H20N3: 350.1652
mp. 243-244℃
下記反応式に示すように、化合物2の合成を経由し、化合物3を合成した。
3,6−ジブロモカルバゾール(500mg,1.42mmol)をDMF(10ml)に溶解させ、水素化ナトリウム(102mg,4.25mmol)を少量ずつ加えていくと溶液が透明から黄色へと変化した。
次に1−ヨードブタン(0.8ml,7.08mmol)を加えると溶液の色はしだいに透明になった。
2時間後、反応を終了し、溶媒をロータリーエバポレーターで除去した。
その後、0.1M NaOH水溶液、ジクロロメタンを加え、有機層を抽出した。
有機層を濃縮、乾燥後、透明で粘性のある固体(765mg)を得た。
1HNMR、HRMSスペクトルより、化合物2であることを確認した。なお、化合物2の精製は行わずに、化合物3の合成に用いた。
1H-NMR スペクトル(500MHz)
Acetone-d6 / TMS
σ=8.20 (2H, s), σ=7.44 (2H, d, J=8.7 Hz), σ=7.36 (2H, d, J=8.7 Hz), σ=4.20 (2H, t, J=7.0 Hz), σ=1.65 (2H, m), σ=1.21 (2H, m), σ=0.77 (3H, t, J=7.5 Hz)
MS スペクトル:MS(APCI) : m/z=378.9567 [M+H]+; calcd. For C16H15Br2N1: 378.9566
化合物2(1.00g,2.62mmol)、4−(5−トリブチルスタニル−2−チオフェニル)ピリジン(2.50g,5.55mmol)およびテトラキス(トリフェニルフォスフィン)パラジウムPd(PPh3)4(151mg,0.13mmol)をDMF(30ml)に溶解させ、90°C、Ar雰囲気下で2時間攪拌した。
反応終了後、反応溶液を水(200ml)に注ぎ、析出した固体をろ過した。
ろ物を乾燥後、シリカゲルカラムクロマトグラフィー(展開溶媒 CH2Cl2:MeOH=20:1)により分離精製し、その後にジクロロメタンで再結晶を行った。
1HNMR、HRMSスペクトルより、化合物3であることを確認した。収量は537mg(収率38%)であった。
1H-NMR スペクトル(500MHz) Dimethyl Sulfoxide-d6 / TMS
σ=8.27 (2H, d J=1.8 Hz), σ=8.15 (4H, dd, J1=4.5 Hz, J2=1.6 Hz), σ=4.44 (2H, d, J=3.9 Hz), σ=7.42(2H, dd, J1=8.8 Hz, J2=1.8 Hz), σ=7.27 (2H, d, J=8.8 Hz), σ=7.24 (4H, dd, J1=4.5 Hz, J2=1.6 Hz), σ=7.23 (2H, d, J=3.9 Hz), σ=4.01 (2H, t, J=7.0 Hz), σ=1.34 (2H, m), σ=0.87(2H, m), σ=0.44 (3H, t,J=7.4 Hz)
MS スペクトル:HRMS (ESI) : m/z= 542.1716 [M+H]+ ; calcd. For C34H28N3S2: 542.1719
mp. 236-237℃
2 第2電極
3 電解質溶液層
11 ガラス基板
12 透明導電膜
13 金属酸化物層
Claims (3)
- 式31で表される、
(式31中、Dはアルキル基、nは0〜3の整数を表す。)
ことを特徴とするドナー―π―アクセプター型化合物。 - 下記化合物3で表される、
ことを特徴とする請求項1に記載のドナー―π―アクセプター型化合物。 - 請求項1又は2に記載のドナー―π―アクセプター型化合物を含有する、
ことを特徴とする色素増感太陽電池用色素。
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JP2014022079A JP2014022079A (ja) | 2014-02-03 |
JP5939573B2 true JP5939573B2 (ja) | 2016-06-22 |
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JP5760779B2 (ja) * | 2010-08-06 | 2015-08-12 | 株式会社リコー | 発光素子及び表示装置 |
JP5621405B2 (ja) * | 2010-08-19 | 2014-11-12 | コニカミノルタ株式会社 | 光電変換素子、光電変換素子の製造方法および太陽電池 |
CN102372693B (zh) * | 2010-08-20 | 2015-03-11 | 清华大学 | 一种咔唑类化合物及其应用 |
TWI504722B (zh) * | 2010-12-03 | 2015-10-21 | Jnc Corp | 具有含吡啶取代基的苯并[c]咔唑化合物及有機電激發光元件 |
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