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WO2018133790A1 - Furane et thiophène contenant des émetteurs pi-fonctionnels - Google Patents

Furane et thiophène contenant des émetteurs pi-fonctionnels Download PDF

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Publication number
WO2018133790A1
WO2018133790A1 PCT/CN2018/072934 CN2018072934W WO2018133790A1 WO 2018133790 A1 WO2018133790 A1 WO 2018133790A1 CN 2018072934 W CN2018072934 W CN 2018072934W WO 2018133790 A1 WO2018133790 A1 WO 2018133790A1
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compound
formula
alkyl
hydrogen
group
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PCT/CN2018/072934
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English (en)
Inventor
Benzhong Tang
Zheng Zhao
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Hong Kong University of Science and Technology
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Hong Kong University of Science and Technology
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Priority to CN201880006572.7A priority Critical patent/CN110300748B/zh
Publication of WO2018133790A1 publication Critical patent/WO2018133790A1/fr
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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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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
    • 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

  • Heteroaromatic groups have been introduced in ⁇ -functional materials to tune their stability, charge mobility, absorption and emission properties.
  • the synthesis of these heteroaromatic containing ⁇ -functional materials still heavily relies on traditional transition-metal catalyzed coupling reactions, which can require air sensitive and/or costly organometallic catalysts and expensive coupling starting materials.
  • the synthesis of the coupling starting material can also be tedious and can require the handling of toxic (e.g., organotin reagents) and flammable (e.g., Grignard reagents) compounds.
  • the preparation of the coupling agents of certain heteroaromatic compounds, such as furan, and their subsequent coupling can be challenging due in part to their low reactivity, which has further limited the development of furan containing ⁇ -functional materials.
  • a thin film comprising any one of the aforementioned compounds.
  • the present disclosure provides improved methods for accessing 2, 5-disubstittued furan-and/or thiophene-based compounds, which can be used as organic semiconductors.
  • This methodology permits the efficient synthesis of heteroaromatic containing ⁇ -functional materials that have been hereto unstudied. Accordingly, this disclosure also provides novel ⁇ -functional materials.
  • This new class of heteroaromatic containing ⁇ -functional materials exhibit unique properties that are useful in the preparation of organic semiconductors.
  • heteroatom is art-recognized and refers to an atom of any element other than carbon or hydrogen.
  • Illustrative heteroatoms include boron, nitrogen, oxygen, phosphorus, sulfur and selenium.
  • Heterocyclyl groups include, for example, thiophene, thianthrene, furan, pyran, isobenzofuran, chromene, xanthene, phenoxanthene, pyrrole, imidazole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indolizine, isoindole, indole, indazole, purine, quinolizine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, carboline, phenanthridine, acridine, pyrimidine, phenanthroline, phenazine, phenarsazine, phenothiazine, furazan, phenoxazine, pyrrolidine, o
  • n is 1 and R 3 is independently attached at either the para or ortho position of each of the aryl groups of the moiety of Formula 2.
  • each instance of R 5 is independently selected from the group consisting of diaryl amine
  • terminal alkynes are shown below:
  • n 1 and R 3 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, and amino.
  • n is independently selected between 1, 2, or 3;
  • X is sulfur or oxygen; and each instance of R 3 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, and amino;
  • R 4 is hydrogen, alkyl, cycloalkyl, aryl, or heteroaryl;
  • R 6 is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amino, ketone, nitro, nitrile, halide, ester, or sulfone.
  • TPE-F Compared with TPE-T, the aggregates of TPE-F surprisingly showed a stronger PL.
  • the quantum yields of TPE-F and TPE-T in dilute THF solutions were determined to be 3.5%and 3.7%by a calibrated integrating sphere. In the solid state, their quantum yields were measured to be 50%and 18%.
  • TPE-F and TPE-T were deposited by spin-coating method of their from dichlormethane solutions of TPE-F and TPE-T, which gave an amorphous film.
  • the hole mobility of TPE-F was two orders magnitude higher than TPE-T, thanks to its better charge injection and more compact molecular packing.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés organiques contenant des hétéroaromatiques et des méthodes d'utilisation et de préparation de ceux-ci. Les composés de l'invention peuvent être utilisés en tant que semi-conducteurs organiques.
PCT/CN2018/072934 2017-01-17 2018-01-17 Furane et thiophène contenant des émetteurs pi-fonctionnels Ceased WO2018133790A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880006572.7A CN110300748B (zh) 2017-01-17 2018-01-17 基于呋喃和噻吩的π-功能发光体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762499069P 2017-01-17 2017-01-17
US62/499,069 2017-01-17

Publications (1)

Publication Number Publication Date
WO2018133790A1 true WO2018133790A1 (fr) 2018-07-26

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111808068B (zh) * 2020-06-22 2023-04-07 南京信息工程大学 四苯乙烯功能化的齐聚噻吩衍生物及其制备方法与应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013019A (en) * 1959-07-29 1961-12-12 Nat Distillers Chem Corp Bis(p-benzoylephenyl) thiophenes
JP2003081969A (ja) * 2001-05-30 2003-03-19 Mitsui Chemicals Inc 有機電界発光素子および新規チオフェン化合物
WO2011106990A1 (fr) * 2010-03-01 2011-09-09 The Hong Kong University Of Science And Technology Dérivés de tétraphénylène électroluminescents, leur procédé de préparation et dispositif électroluminescent utilisant ces dérivés
CN104094435A (zh) * 2011-09-02 2014-10-08 巴斯夫欧洲公司 二酮基吡咯并吡咯低聚物和包含二酮基吡咯并吡咯低聚物的组合物
CN105683193A (zh) * 2013-10-28 2016-06-15 株式会社Lg化学 单分子和包含其的太阳能电池

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3777682B2 (ja) * 1996-11-25 2006-05-24 東洋インキ製造株式会社 有機エレクトロルミネッセンス素子材料およびそれを用いた有機エレクトロルミネッセンス素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013019A (en) * 1959-07-29 1961-12-12 Nat Distillers Chem Corp Bis(p-benzoylephenyl) thiophenes
JP2003081969A (ja) * 2001-05-30 2003-03-19 Mitsui Chemicals Inc 有機電界発光素子および新規チオフェン化合物
WO2011106990A1 (fr) * 2010-03-01 2011-09-09 The Hong Kong University Of Science And Technology Dérivés de tétraphénylène électroluminescents, leur procédé de préparation et dispositif électroluminescent utilisant ces dérivés
CN104094435A (zh) * 2011-09-02 2014-10-08 巴斯夫欧洲公司 二酮基吡咯并吡咯低聚物和包含二酮基吡咯并吡咯低聚物的组合物
CN105683193A (zh) * 2013-10-28 2016-06-15 株式会社Lg化学 单分子和包含其的太阳能电池

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HARTNETT PATRICK E ET AL.: "Ring-fusion as a perylenediimide dimer design concept for high- performance non-fullerene organic photovoltaic acceptors", CHEM. SCI., vol. 7, 9 February 2016 (2016-02-09), pages 3543 - 3555, XP055506226 *
T OYATA SHINJI ET AL.: "Synthesis, structures, and properties of 2, 5-dianthrylthiophene derivatives", CAN. J. CHEM., vol. 95, 8 September 2016 (2016-09-08), pages 286 - 291 *
ZHONG HONGLIANG ET AL.: "Rigidifying Nonplanar Perylene Diimides by Ring Fusion Toward Geometry-Tunable Acceptors for High-Performance Fullerene-Free Solar Cells", ADVANCED MATERIALS, vol. 28, 31 December 2016 (2016-12-31), pages 951 - 958, XP055506231 *

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CN110300748B (zh) 2022-08-12

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