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1. WO2016015533 - ORGANIC SMALL MOLECULAR SEMICONDUCTOR MATERIAL, AND SYNTHETIC METHOD AND USE THEREOF

Publication Number WO/2016/015533
Publication Date 04.02.2016
International Application No. PCT/CN2015/082416
International Filing Date 26.06.2015
IPC
C07D 495/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
C07D 495/14 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
12in which the condensed system contains three hetero rings
14Ortho-condensed systems
C07F 7/10 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC, OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
7Compounds containing elements of Groups 4 or 14 of the Periodic System
02Silicon compounds
08Compounds having one or more C-Si linkages
10containing nitrogen
C08G 61/12 2006.01
CCHEMISTRY; METALLURGY
08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
61Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
12Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
C08L 65/00 2006.01
CCHEMISTRY; METALLURGY
08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
65Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
H01L 51/46 2006.01
HELECTRICITY
01BASIC ELECTRIC ELEMENTS
LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
51Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
42specially adapted for sensing infra-red radiation, light, electromagnetic radiation of shorter wavelength, or corpuscular radiation; 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
46Selection of materials
CPC
C07D 495/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
C07D 495/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
12in which the condensed system contains three hetero rings
14Ortho-condensed systems
C07F 7/10
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
7Compounds containing elements of Groups 4 or 14 of the Periodic System
02Silicon compounds
08Compounds having one or more C—Si linkages
10containing nitrogen ; having a Si-N linkage
C08G 61/12
CCHEMISTRY; METALLURGY
08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
61Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
12Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
C08L 65/00
CCHEMISTRY; METALLURGY
08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
65Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain
Applicants
  • 深圳市博世知识产权运营有限公司 SHENZHEN BOSCH INTELLECTUAL PROPERTY OPERATION CO., LTD [CN]/[CN]
Inventors
  • 武建昌 WU, Jianchang
  • 马玉超 MA, Yuchao
  • 王立磊 WANG, Lilei
  • 马昌期 MA, Changqi
Agents
  • 深圳市铭粤知识产权代理有限公司 MING & YUE INTELLECTUAL PROPERTY LAW FIRM
Priority Data
201410374771.701.08.2014CN
Publication Language Chinese (ZH)
Filing Language Chinese (ZH)
Designated States
Title
(EN) ORGANIC SMALL MOLECULAR SEMICONDUCTOR MATERIAL, AND SYNTHETIC METHOD AND USE THEREOF
(FR) MATÉRIAU SEMI-CONDUCTEUR ORGANIQUE À PETITES MOLÉCULES
(ZH) 有机小分子半导体材料、其合成方法及应用
Abstract
(EN)
Disclosed are an organic small molecular semiconductor material, and a synthetic method therefor. The semiconductor material comprises a diaromatic ring pentalene π-conjugate unit and an aromatic group, and has the following structural formula (I), wherein X1 and X2 are independently selected from O, S or Se; X3 is selected from O, S, Se, NR2, C(R2)2 or Si(R2)2; R2 is selected from a linear or branched alkyl group comprising 1-20 carbon atoms, and a linear or branched modified alkaryl or heterocyclic aryl comprising 7-20 carbon atoms; R1 is selected from a hydrogen atom, a linear or branched alkyl group comprising 1-20 carbon atoms, and a linear or branched modified alkaryl or heterocyclic aryl comprising 7-20 carbon atoms; and A is an electron-withdrawing unit. The semiconductor material can be synthesised by a transition metal catalysed condensation reaction. The semiconductor material of the present invention has a small spectrum band gap, a long spectrum absorption wavelength, a relatively low highest occupied molecular orbital and lowest unoccupied molecular orbital energy level, and can be used as a photoelectric material, especially as a receptor material in an organic photovoltaic device, and it also has advantages such as a simple preparation process, a low cost, etc.
(FR)
Cette invention concerne un matériau semi-conducteur organique à petites molécules, et son procédé de synthèse. Le matériau semi-conducteur comprend un motif pentalène à cycle diaromatique conjugué à π et un groupe aromatique, et répond à la formule structurale suivante (I), dans laquelle X1 et X2 sont indépendamment choisis parmi O, S ou Se ; X3 est choisi parmi O, S, Se, NR2, C(R2)2 ou Si(R2)2 ; R2 est choisi parmi un groupe alkyle linéaire ou ramifié comprenant de 1 à 20 atomes de carbone, et un alkaryle modifié linéaire ou ramifié ou un aryle hétérocyclique comprenant de 7 à 20 atomes de carbone ; R1 est choisi parmi un atome d'hydrogène, un groupe alkyle linéaire ou ramifié comprenant de 1 à 20 atomes de carbone, et un alkaryle modifié linéaire ou ramifié ou un aryle hétérocyclique comprenant de 7 à 20 atomes de carbone ; et A est un motif électro-attracteur. Le matériau semi-conducteur peut être synthétisé par une réaction de condensation catalysée par un métal de transition. Le matériau semi-conducteur selon l'invention a une petite bande interdite de spectre, une longue longueur d'onde d'absorption de spectre, une orbitale moléculaire occupée la plus élevée et un niveau d'énergie orbitale moléculaire non occupée la plus basse relativement basses, et peut être utilisé à titre de matériau photoélectrique, notamment à titre de matériau récepteur dans un dispositif photovoltaïque organique, et il présente également des avantages tels qu'un procédé de préparation simple, un faible coût, etc
(ZH)
本发明公开了一种有机小分子半导体材料及其合成方法。该半导体材料包含二芳环并环戊二烯类π共轭单元及芳香基团,并具有如下结构式 (I) ,其中X1、X2独立地选自O、S或Se,X3选自O、S、Se、NR2、C(R2)2或Si(R2)2,R2选自含C数为1-20的直链或支链烷基、含C数为7-20的直链或支链修饰的烷芳基或杂环芳基,R1选自氢原子、含C数为1-20的直链或支链烷基、含C数为7-20的直链或支链修饰的烷芳基或杂环芳基,A为吸电子单元。该半导体材料可通过过渡金属催化缩合反应合成。本发明的具有小的光谱带隙,长的光谱吸收波长,较低的最高占据轨道及最低空轨道能级,可作为光电材料,尤其是有机光伏器件中的受体材料,且其还具有制备工艺简单、成本低廉等优点。
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