KR100969675B1 - 신규한 엔-아릴카바졸 잔기-함유 유기염료 및 이의제조방법 - Google Patents
신규한 엔-아릴카바졸 잔기-함유 유기염료 및 이의제조방법 Download PDFInfo
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- KR100969675B1 KR100969675B1 KR1020070050698A KR20070050698A KR100969675B1 KR 100969675 B1 KR100969675 B1 KR 100969675B1 KR 1020070050698 A KR1020070050698 A KR 1020070050698A KR 20070050698 A KR20070050698 A KR 20070050698A KR 100969675 B1 KR100969675 B1 KR 100969675B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- dye
- arylcarbazole
- photoelectric conversion
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 239000000975 dye Substances 0.000 claims abstract description 92
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004065 semiconductor Substances 0.000 claims description 46
- 239000010419 fine particle Substances 0.000 claims description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 25
- 239000010409 thin film Substances 0.000 claims description 22
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000003792 electrolyte Substances 0.000 claims description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 18
- -1 9,9-dimethylfluorenyl Chemical group 0.000 claims description 17
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 14
- 239000010408 film Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 11
- OYIGWMXXIFYAGD-UHFFFAOYSA-N 3-iodo-9h-carbazole Chemical compound C1=CC=C2C3=CC(I)=CC=C3NC2=C1 OYIGWMXXIFYAGD-UHFFFAOYSA-N 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 7
- JGRMXPSUZIYDRR-UHFFFAOYSA-N 2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid Chemical group OC(=O)CN1C(=O)CSC1=S JGRMXPSUZIYDRR-UHFFFAOYSA-N 0.000 claims description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B49/00—Sulfur dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B49/00—Sulfur dyes
- C09B49/12—Sulfur dyes from other compounds, e.g. other heterocyclic compounds
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- 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
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- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
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- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
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- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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| KR1020070050698A KR100969675B1 (ko) | 2007-05-25 | 2007-05-25 | 신규한 엔-아릴카바졸 잔기-함유 유기염료 및 이의제조방법 |
| PCT/KR2007/003206 WO2008146975A1 (fr) | 2007-05-25 | 2007-07-03 | Nouveau colorant organique contenant un fragment n-arylcarbazole et sa préparation |
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| KR1020070050698A KR100969675B1 (ko) | 2007-05-25 | 2007-05-25 | 신규한 엔-아릴카바졸 잔기-함유 유기염료 및 이의제조방법 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102167913A (zh) * | 2011-02-25 | 2011-08-31 | 中国科学院上海有机化学研究所 | 含多联咔唑的有机染料及其制备方法和应用 |
| KR101150507B1 (ko) | 2009-05-21 | 2012-05-31 | 고려대학교 산학협력단 | 엑스모양 공액형 유기 화합물, 이를 이용한 염료감응 광전변환소자 및 염료감응 태양전지 |
| KR101749379B1 (ko) | 2014-06-12 | 2017-06-20 | 주식회사 엘지화학 | 공중합체, 이의 제조방법 및 상기 공중합체를 포함하는 유기 태양 전지 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5875988B2 (ja) * | 2009-12-30 | 2016-03-02 | ドンジン セミケム カンパニー リミテッド | 新規な有機染料およびその製造方法 |
| KR101882394B1 (ko) * | 2009-12-31 | 2018-07-26 | 주식회사 동진쎄미켐 | 신규한 유기염료 및 이의 제조방법 |
| WO2011081357A2 (fr) * | 2009-12-30 | 2011-07-07 | 주식회사 동진쎄미켐 | Nouveau colorant organique et son procédé de préparation |
| JP5700937B2 (ja) * | 2010-02-09 | 2015-04-15 | 保土谷化学工業株式会社 | 光電変換用増感色素及びそれを用いた光電変換素子及び色素増感太陽電池 |
| KR101311584B1 (ko) * | 2010-06-29 | 2013-09-26 | 고려대학교 산학협력단 | 정공전도성을 갖는 화합물, 그의 공흡착체로서의 용도, 및 그를 포함하는 염료감응 태양전지 |
| WO2012078005A2 (fr) * | 2010-12-10 | 2012-06-14 | 고려대학교 산학협력단 | Composés dotés de la propriété de conduction par trous, corps co-adsorbant en contenant et photopile sensibilisée par un colorant intégrant ledit corps co-adsorbant |
| JP5771092B2 (ja) * | 2011-03-31 | 2015-08-26 | 富士フイルム株式会社 | 色素、光電変換素子及び光電気化学電池 |
| CN102604412B (zh) * | 2012-01-17 | 2014-03-26 | 北京师范大学 | 用于染料敏化太阳能电池的含双并咔唑基团的染料及制备 |
| KR102191154B1 (ko) * | 2012-06-26 | 2021-01-15 | 동진홀딩스 주식회사 | 신규한 화합물 및 이를 포함하는 발광소자 |
| WO2014003405A1 (fr) * | 2012-06-26 | 2014-01-03 | 주식회사 제이앤드제이 캐미칼 | Nouveau composé et dispositif émettant de la lumière le comprenant |
| KR101465454B1 (ko) * | 2012-11-13 | 2014-12-02 | 재단법인대구경북과학기술원 | 염료감응 태양전지용 유기염료 및 이를 포함하는 염료감응 태양전지 |
| KR102394380B1 (ko) * | 2013-12-03 | 2022-05-06 | 주식회사 동진쎄미켐 | 신규한 발광 화합물 및 이를 포함하는 유기발광소자 |
| CN110372719B (zh) * | 2019-08-09 | 2020-08-11 | 浙江工业大学 | N-芴基苯并咔唑类化合物、制备方法及其应用 |
| CN110498793B (zh) * | 2019-08-12 | 2022-12-16 | 常州大学 | 基于罗丹宁的小分子光伏体相材料及其应用 |
| CN111875599A (zh) * | 2020-08-12 | 2020-11-03 | 陕西理工大学 | 一种罗丹宁乙酸为受体的y型共敏剂及其制备方法 |
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| US4908435A (en) | 1987-02-27 | 1990-03-13 | Imperial Chemical Industries Plc | Aromatic disazo compounds having strong infra-red absorption |
| JPH06104471A (ja) * | 1992-09-22 | 1994-04-15 | Mita Ind Co Ltd | 有機太陽電池 |
| US6313288B1 (en) | 1998-11-18 | 2001-11-06 | Ricoh Company, Ltd. | Mixture of titanyltetraazaporphyrin compounds and electrophotographic photoconductor using the same |
| JP2004146733A (ja) | 2002-10-28 | 2004-05-20 | Konica Minolta Holdings Inc | 有機半導体及びそれを用いる有機薄膜トランジスタ素子 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1628356B1 (fr) * | 2003-03-14 | 2012-08-15 | Nippon Kayaku Kabushiki Kaisha | Dispositif de conversion photoelectrique sensibilise par colorant |
-
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- 2007-05-25 KR KR1020070050698A patent/KR100969675B1/ko not_active IP Right Cessation
- 2007-07-03 WO PCT/KR2007/003206 patent/WO2008146975A1/fr active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4908435A (en) | 1987-02-27 | 1990-03-13 | Imperial Chemical Industries Plc | Aromatic disazo compounds having strong infra-red absorption |
| JPH06104471A (ja) * | 1992-09-22 | 1994-04-15 | Mita Ind Co Ltd | 有機太陽電池 |
| US6313288B1 (en) | 1998-11-18 | 2001-11-06 | Ricoh Company, Ltd. | Mixture of titanyltetraazaporphyrin compounds and electrophotographic photoconductor using the same |
| JP2004146733A (ja) | 2002-10-28 | 2004-05-20 | Konica Minolta Holdings Inc | 有機半導体及びそれを用いる有機薄膜トランジスタ素子 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101150507B1 (ko) | 2009-05-21 | 2012-05-31 | 고려대학교 산학협력단 | 엑스모양 공액형 유기 화합물, 이를 이용한 염료감응 광전변환소자 및 염료감응 태양전지 |
| CN102167913A (zh) * | 2011-02-25 | 2011-08-31 | 中国科学院上海有机化学研究所 | 含多联咔唑的有机染料及其制备方法和应用 |
| KR101749379B1 (ko) | 2014-06-12 | 2017-06-20 | 주식회사 엘지화학 | 공중합체, 이의 제조방법 및 상기 공중합체를 포함하는 유기 태양 전지 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008146975A1 (fr) | 2008-12-04 |
| KR20080103680A (ko) | 2008-11-28 |
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