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WO2018032945A1 - Composé photoélectrique contenant une modification du benzothiophène (benzosélénophène), son procédé de préparation et son utilisation - Google Patents

Composé photoélectrique contenant une modification du benzothiophène (benzosélénophène), son procédé de préparation et son utilisation Download PDF

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Publication number
WO2018032945A1
WO2018032945A1 PCT/CN2017/094220 CN2017094220W WO2018032945A1 WO 2018032945 A1 WO2018032945 A1 WO 2018032945A1 CN 2017094220 W CN2017094220 W CN 2017094220W WO 2018032945 A1 WO2018032945 A1 WO 2018032945A1
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WO
WIPO (PCT)
Prior art keywords
halo
halogenated
compound
selenophene
thiophene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2017/094220
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English (en)
Chinese (zh)
Inventor
邓丹
魏志祥
吕琨
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
National Center for Nanosccience and Technology China
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National Center for Nanosccience and Technology China
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Filing date
Publication date
Application filed by National Center for Nanosccience and Technology China filed Critical National Center for Nanosccience and Technology China
Publication of WO2018032945A1 publication Critical patent/WO2018032945A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
    • C07D517/04—Ortho-condensed systems
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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

  • a suitable amount of M1 or M2 is dissolved in chloroform to form a solution of a certain concentration, and a part of the solution is spin-coated on a quartz plate to form a film of a small molecule.
  • the UV-visible absorption spectrum of the compound of M1-M4 measured in a chloroform solution and a film state is shown in Figs. It can be seen from the figure that M1-M4 has a broad absorption in the visible light region, and the film is red-shifted by about 80 nm with respect to the solution, indicating that the two have a good aggregation effect in the film.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Photovoltaic Devices (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un composé photovoltaïque organique pouvant être traité en solution à l'aide de benzothiophène (benzosélénophène) et de thiophène (sélénophène) en tant que pont pi, et son utilisation, la formule structurale du composé étant représentée par la formule I. Par sélection d'un composé photoélectrique organique approprié de D et A unités sur la base du pont pi, le composé de la présente invention présente une faible énergie de liaison d'excitons et est capable de réduire efficacement le niveau le plus élevé d'énergie électronique orbitale de molécules, ce qui permet d'obtenir un matériau à haut rendement pour obtenir une tension de circuit ouvert élevée. En tant que matériau donneur d'une couche active d'une cellule solaire organique, le composé de la présente invention a une tension de circuit ouvert plus élevée que 1 V. Le composé utilise une unité de récepteur fluoré en tant que terminal. Le rendement de conversion d'énergie de cellule d'une structure ordonnée de la cellule solaire dépasse 10 %, et le rendement de conversion d'énergie de cellule d'une structure de dispositif inversé de la cellule solaire atteint 11,5 % sans être soumise à un aucun traitement additif ou thermique et traitement de recuit de solvant. Le composé présente une valeur d'application importante.
PCT/CN2017/094220 2016-08-17 2017-07-25 Composé photoélectrique contenant une modification du benzothiophène (benzosélénophène), son procédé de préparation et son utilisation Ceased WO2018032945A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610682862.6 2016-08-17
CN201610682862.6A CN107759621B (zh) 2016-08-17 2016-08-17 一种含有并噻吩（并硒吩）修饰的光电化合物及其制备方法和用途

Publications (1)

Publication Number Publication Date
WO2018032945A1 true WO2018032945A1 (fr) 2018-02-22

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PCT/CN2017/094220 Ceased WO2018032945A1 (fr) 2016-08-17 2017-07-25 Composé photoélectrique contenant une modification du benzothiophène (benzosélénophène), son procédé de préparation et son utilisation

Country Status (2)

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CN (1) CN107759621B (fr)
WO (1) WO2018032945A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109608475A (zh) * 2019-01-22 2019-04-12 湘潭大学 A′-π-A-π-A′型有机小分子及其制备方法与应用
WO2019164054A1 (fr) * 2018-02-26 2019-08-29 한국화학연구원 Nouveau composé, procédé de fabrication de celui-ci et élément électronique organique l'utilisant
WO2019176488A1 (fr) * 2018-03-15 2019-09-19 Ricoh Company, Ltd. Matériau organique et élément de conversion photoélectrique
CN113461714A (zh) * 2021-07-15 2021-10-01 杭州师范大学 窄带隙非稠环小分子受体及其制备方法和应用
CN114736232A (zh) * 2022-05-11 2022-07-12 江西师范大学 一种双酯基并噻吩非稠环电子受体材料及制备方法和应用
US11398603B2 (en) * 2017-10-23 2022-07-26 Lg Chem, Ltd. Heterocyclic compound and organic electronic device comprising same
CN115612068A (zh) * 2022-09-30 2023-01-17 武汉工程大学 一类卤代噻唑类宽带隙聚合物及其在光电器件中的应用

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114106017B (zh) * 2020-08-31 2023-05-19 中国科学院宁波材料技术与工程研究所 含有并噻吩的小分子给体材料及其制备方法、太阳能电池
CN113943311A (zh) * 2021-11-22 2022-01-18 北京航空航天大学 一种新型非富勒烯小分子的制备与应用
CN114891020B (zh) * 2022-04-22 2024-10-18 国家纳米科学中心 一种寡聚物受体材料、其制备方法和太阳能电池
CN116023633B (zh) * 2022-11-25 2025-01-14 中国人民解放军96901部队25分队 一种供体-受体型电致变色聚合物及其制备方法和一种聚合物薄膜
CN117402177B (zh) * 2023-10-13 2025-07-25 宁波大学 一种有机光电化合物及其制备方法和应用

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CN102803394A (zh) * 2009-06-19 2012-11-28 株式会社东进世美肯 新型有机染料及其制造方法
WO2013129605A1 (fr) * 2012-03-01 2013-09-06 関東天然瓦斯開発株式会社 Composé colorant totalement organique ayant une structure non plane pour des éléments de conversion photoélectrique sensibilisés par un colorant et élément de conversion photoélectrique l'utilisant
CN105315298A (zh) * 2014-08-04 2016-02-10 中国科学院化学研究所 基于七并稠环单元的a-d-a共轭分子及其制备方法和应用

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CN105646559B (zh) * 2014-11-27 2018-09-11 中国科学院苏州纳米技术与纳米仿生研究所 有机π-共轭化合物、其制备方法及应用

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CN102803394A (zh) * 2009-06-19 2012-11-28 株式会社东进世美肯 新型有机染料及其制造方法
WO2013129605A1 (fr) * 2012-03-01 2013-09-06 関東天然瓦斯開発株式会社 Composé colorant totalement organique ayant une structure non plane pour des éléments de conversion photoélectrique sensibilisés par un colorant et élément de conversion photoélectrique l'utilisant
CN105315298A (zh) * 2014-08-04 2016-02-10 中国科学院化学研究所 基于七并稠环单元的a-d-a共轭分子及其制备方法和应用

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ZHU, SHENGBO ET AL.: "Cyclic Thiourea Functionalized Dyes with Binary p-Linkers: Influence of Different p-Conjugation Segments on the Performance of Dye-sensitized Solar Cells", DYES AND PIGMENTS, 4 February 2015 (2015-02-04), XP029200872, ISSN: 0143-7208 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11398603B2 (en) * 2017-10-23 2022-07-26 Lg Chem, Ltd. Heterocyclic compound and organic electronic device comprising same
WO2019164054A1 (fr) * 2018-02-26 2019-08-29 한국화학연구원 Nouveau composé, procédé de fabrication de celui-ci et élément électronique organique l'utilisant
KR20190102622A (ko) * 2018-02-26 2019-09-04 한국화학연구원 신규한 화합물, 이의 제조방법 및 이를 이용하는 유기 전자 소자
KR102114177B1 (ko) * 2018-02-26 2020-05-22 한국화학연구원 신규한 화합물, 이의 제조방법 및 이를 이용하는 유기 전자 소자
WO2019176488A1 (fr) * 2018-03-15 2019-09-19 Ricoh Company, Ltd. Matériau organique et élément de conversion photoélectrique
US11950503B2 (en) 2018-03-15 2024-04-02 Ricoh Company, Ltd. Organic material and photoelectric conversion element
CN109608475A (zh) * 2019-01-22 2019-04-12 湘潭大学 A′-π-A-π-A′型有机小分子及其制备方法与应用
CN109608475B (zh) * 2019-01-22 2021-04-27 湘潭大学 A′-π-A-π-A′型有机小分子及其制备方法与应用
CN113461714A (zh) * 2021-07-15 2021-10-01 杭州师范大学 窄带隙非稠环小分子受体及其制备方法和应用
CN114736232A (zh) * 2022-05-11 2022-07-12 江西师范大学 一种双酯基并噻吩非稠环电子受体材料及制备方法和应用
CN115612068A (zh) * 2022-09-30 2023-01-17 武汉工程大学 一类卤代噻唑类宽带隙聚合物及其在光电器件中的应用

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CN107759621A (zh) 2018-03-06

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