CN105073945A - 半导体聚合物 - Google Patents
半导体聚合物 Download PDFInfo
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- CN105073945A CN105073945A CN201480013929.6A CN201480013929A CN105073945A CN 105073945 A CN105073945 A CN 105073945A CN 201480013929 A CN201480013929 A CN 201480013929A CN 105073945 A CN105073945 A CN 105073945A
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- polymkeric substance
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 18
- 229920000642 polymer Polymers 0.000 title claims abstract description 16
- 239000000126 substance Substances 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- -1 2-ethylhexyl Chemical group 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 26
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
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- 239000001257 hydrogen Substances 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 125000005647 linker group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
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- 150000003624 transition metals Chemical class 0.000 claims description 8
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052789 astatine Inorganic materials 0.000 claims description 7
- RYXHOMYVWAEKHL-UHFFFAOYSA-N astatine atom Chemical compound [At] RYXHOMYVWAEKHL-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052794 bromium Inorganic materials 0.000 claims description 7
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- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- WEMQMWWWCBYPOV-UHFFFAOYSA-N s-indacene Chemical compound C=1C2=CC=CC2=CC2=CC=CC2=1 WEMQMWWWCBYPOV-UHFFFAOYSA-N 0.000 description 1
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- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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Abstract
公开了具有如下结构的半导体聚合物(I)。
Description
相关申请的交叉引用
本申请要求2013年3月13日申请的美国临时专利申请第61/779786号的权益。所参照申请的内容以引用方式并入本申请中。
发明背景
A.技术领域
本发明一般性涉及可用于有机光伏电池的半导体聚合物的用途。特别地,本发明的聚合物是通过1,4二乙烯基苯连接体连接在一起的基于苝酰亚胺的n型半导体聚合物。
B.相关技术描述
上涨的能量价格及与因燃烧化石燃料导致的全球变暖相关的问题已导致对更成本有效且可更有效再生的能源的探寻。一种已认定的这种再生能源是太阳能。相关于将太阳能转换成电的问题在很大程度上归因于能量转换过程的低效性。例如,已研发出可将太阳能转化成可用能量的光伏电池(例如,太阳能电池),但是关于转化的成本阻碍将此技术广泛应用于市场。
近年来,涉及聚合物在有机光伏电池的光活性层中的用途的研究愈来愈多。使用聚合物的独特方面之一是其允许通过例如旋涂、浸涂或喷墨印刷等成本有效的溶液处理技术制造有机电子器件。与用于制造无机薄膜器件的依赖于真空沉积技术的蒸发技术相比,溶液处理可以更廉价且以更大的规模实施。
然而,许多目前所用的聚合物遇到低载流子迁移率(电导)、较低光吸收性能的问题,且合成复杂。此问题的一个解决方案是从聚合物转换为基于非聚合物的n型材料,例如[6,6]-苯基C71丁酸甲酯(PC71BM)。PC71BM是在太阳能电池应用中现今所用的最普遍的n型材料之一。其具有以下通式结构:
尽管此材料为充分的n型半导体,但其并非聚合物且可改良其光吸收及带隙性能。
发明内容
已发现由利用1,4二乙烯基苯连接体连接在一起的苝酰亚胺基团制得的聚合物是与例如PC71BM等已知n型材料相比具有改良的光吸收及较低带隙特性的n型半导体聚合物。此外,这些聚合物可通过生成高产率的聚合物的可规模化方法来制得。本发明的聚合物可用于有机光伏电池的光活性层(例如,该聚合物可用作n型半导体聚合物)。
在本发明的至少一个方面中,公开了可用于有机光伏电池中的光活性层的具有以下结构的聚合物:
其中
R1和R2各自独立地选自H、C1-30烷基、C2-30烯基、C2-30炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基,
R3、R4、R9和R10各自独立地为氢或-CN,
R5、R6、R7和R8各自独立地为氢、卤素、-CN、-NO2、-OH、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C3-10环烷基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基,其中卤素选自氟、氯、溴、碘和砹;满足如下条件:R5、R6、R7及R8中的任一个均非烷氧基(-OX1)或R5、R6、R7及R8中的至少三个或所有四个均为烷氧基,
其中
X1和X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基,且
n是大于2或2至1000、或2至500、或2至100、或2至50、或2至25、或2至20或2至15的整数。
在某些方面中,R1和R2可各自独立地为氢、带支链或不带支链的C1-30烷基、C2-30烯基或C2-30炔基。在其他情况下,R1和R2可各自独立地为氢、带支链或不带支链的C3-10环烷基、C5-10环烯基或3元至14元环杂烷基。在另外的实施方案中,R1和R2可各自独立地为氢、带支链或不带支链的C6-14芳基或5元至14元杂芳基。这些基团中的任一个可未经取代或经独立地选自以下的1个至6个基团取代:卤素(例如,氟、氯、溴、碘及砹)、-CN、-NO2、-OH、C1-10烷氧基(例如,甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、正戊氧基、新戊氧基、异戊氧基、己氧基、正庚氧基、正辛氧基、正壬氧基及正癸氧基)、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基,其中X1和X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基。
C1-30烷基的非限制性实例是C1-10烷基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基及正二十烷基(C20)、正二十二烷基(C22)、正二十四烷基(C24)、正二十六烷基(C26)、正二十八烷基(C28)及正三十烷基(C30)。C1-10烷基的非限制性实例是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、新戊基、异戊基、正-(1-乙基)丙基、正己基、正庚基、正辛基、正-(2-乙基)己基、正壬基及正癸基。C3-8烷基的非限制性实例是正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、新戊基、异戊基、正-(1-乙基)丙基、正己基、正庚基、正辛基及正-(2-乙基)己基。
C2-30烯基的非限制性实例是C2-10烯基及亚油烯基(C18)、亚麻烯基(C18)、油烯基(C18)、花生四烯基(C20)及瓢儿菜基(C22)。C2-10烯基的非限制性实例是乙烯基、丙烯基、顺式-2-丁烯基、反式-2-丁烯基、3-丁烯基、顺式-2-戊烯基、反式-2-戊烯基、顺式-3-戊烯基、反式-3-戊烯基、4-戊烯基、2-甲基-3-丁烯基、己烯基、庚烯基、辛烯基、壬烯基及癸烯基。
C2-30炔基的非限制性实例是C2-10炔基、十一炔基、十二炔基、十一炔基、十二炔基、十三炔基、十四炔基、十五炔基、十六炔基、十七炔基、十八炔基、十九炔基及二十炔基(C20)。C2-10炔基的非限制性实例是乙炔基、2-丙炔基、2-丁炔基、3-丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基及癸炔基。
C3-10环烷基的非限制性实例是单环C3-10环烷基,例如环丙基、环丁基、环戊基、环己基、环庚基及环辛基,但是也包括多环C3-10环烷基,例如十氢萘基、降莰基及金刚烷基。
C5-10环烯基的非限制性实例包括单环C5-10环烯基、例如环戊烯基、环己烯基、环己二烯基及环庚三烯基,以及多环C5-10环烯基。
3元至14元环杂烷基的非限制性实例包括单环3元至8元环杂烷基及多环(例如,二环7元至12元环杂烷基)。单环3元至8元环杂烷基的非限制性实例包括含有一个杂原子的单环5元环杂烷基(例如吡咯烷基、1-吡咯啉基、2-吡咯啉基、3-吡咯啉基、四氢呋喃基、2,3-二氢呋喃基、四氢苯硫基及2,3-二氢苯硫基)、含有两个杂原子的单环5元环杂烷基(例如咪唑烷基、咪唑啉基、吡唑烷基、吡唑啉基、唑烷基、唑啉基、异唑烷基、异唑啉基、噻唑烷基、噻唑啉基、异噻唑烷基及异噻唑啉基)、含有三个杂原子的单环5元环杂烷基(例如1,2,3-***基、1,2,4-***基及1,4,2-二噻唑基)、含有一个杂原子的单环6元环杂烷基(例如哌啶基(piperidyl)、哌啶子基(piperidino)、四氢吡喃基、吡喃基(pyranyl)、四氢噻喃基(thianyl)及噻喃基)、含有两个杂原子的单环6元环杂烷基(例如哌嗪基、吗啉基(morpholinyl)、吗啉代基(morpholino)及噻嗪基)、含有一个杂原子的单环7元环杂烷基(例如氮杂环庚烷基、氮杂卓基、氧杂环庚烷基、硫杂环庚烷基、噻环庚烷基(thiapanyl)、硫杂卓基(thiepinyl))及含有两个杂原子的单环7元环杂烷基(例如1,2-二氮杂卓基及1,3-硫氮杂卓基)。二环7元至12元环杂烷基的一个实例是十氢萘基。
C6-14芳基的非限制性实例包括单环或多环芳基。这样的实例包括单环C6芳基(例如苯基)、二环C6-10芳基(例如1-萘基、2-萘基、茚基、二氢茚基及四氢萘基)及三环C12-14芳基(例如蒽基、菲基、芴基及对称引达省基(s-indacenyl))。
5元至14元杂芳基的非限制性实例可以是单环5元至8元杂芳基或多环7元至14元杂芳基(例如,二环7元至12元或三环9元至14元杂芳基)。单环5元至8元杂芳基的实例包括含有一个杂原子的单环5元杂芳基(例如吡咯基、呋喃基及苯硫基)、含有两个杂原子的单环5元杂芳基(例如咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基)、含有三个杂原子的单环5元杂芳基(例如1,2,3-***基、1,2,4-***基及二唑基)、含有四个杂原子的单环5元杂芳基(例如四唑基)、含有一个杂原子的单环6元杂芳基(例如吡啶基)、含有两个杂原子的单环6元杂芳基(例如吡嗪基、嘧啶基及哒嗪基)、含有三个杂原子的单环6元杂芳基(例如1,2,3-三嗪基、1,2,4-三嗪基及1,3,5-三嗪基)、含有一个杂原子的单环7元杂芳基(例如氮杂卓基)及含有两个杂原子的单环7元杂芳基(例如1,2-氮杂卓基)。二环7元至12元杂芳基的实例是含有一个杂原子的二环9元杂芳基(例如吲哚基、异吲哚基、吲嗪基、吲哚啉基、苯并呋喃基、异苯并呋喃基、苯并噻吩基及异苯并噻吩基)、含有两个杂原子的二环9元杂芳基(例如吲唑基、苯并咪唑基、苯并咪唑啉基、苯并唑基、苯并异唑基、苯并噻唑基、苯并异噻唑基、呋喃并吡啶基及噻吩并吡啶基)、含有三个杂原子的二环9元杂芳基(例如苯并***基、苯并二唑基、唑并吡啶基、异唑并吡啶基、噻唑并吡啶基、异噻唑并吡啶基及咪唑并吡啶基)、含有四个杂原子的二环9元杂芳基(例如嘌呤基)、含有一个杂原子的二环10元杂芳基(例如喹啉基、异喹啉基、苯并吡喃基及苯并二氢吡喃基)、含有两个杂原子的二环10元杂芳基(例如喹喔啉基、喹唑啉基、噌啉基、酞嗪基、1,5-萘啶基及1,8-萘啶基)、含有三个杂原子的二环10元杂芳基(例如吡啶并吡嗪基、吡啶并嘧啶基及吡啶并哒嗪基)及含有四个杂原子的二环10元杂芳基(例如喋啶基)。三环9元至14元杂芳基的实例是二苯并呋喃基、吖啶基、吩嗪基、7H-环戊并[1,2-b:3,4-b’]二噻吩基及4H-环戊并[2,1-b:3,4-b’]二噻吩基。
在特定情况下,R1和R2可以是2-乙基己基,2-辛基十二烷基或2-癸基十四烷基。在一种情况下,R1和R2二者均为具有下式的带支链烷基:
此外,在此实施方案中R3、R4、R9及R10中的每一个均可以是氢且R5、R6、R7及R8中的每一个均可以是氢。
本发明的聚合物可以是式(I)与式(II)的反应产物:
其中,R11为选自氟、氯、溴、碘及砹的卤素,且
R12和R13各自独立地为连接基团。
连接基团可以是经取代或未经取代的C2-6烷基或C2-6亚烷基。C2-6烷基的实例包括正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、新戊基、异戊基、正(1-乙基)丙基、正己基或己烷、2-甲基戊烷、3-甲基戊烷、2,3-二甲基丁烷及2,2-二甲基丁烷。C2-6亚烷基的实例包括亚乙基、亚丙基、亚丁基、亚戊基或亚己基。在特定情况下,连接体可以是2,3-二甲基丁烷。在另一方面中,本发明的聚合物可通过使式(I)与式(II)在含有过渡金属的催化剂(例如,Pd(PPh3)4)的存在下反应来制备。该方法可进一步包括将式(I)、式(II)和将含有过渡金属的催化剂混合或组合在一起以形成混合物,并加热该混合物(例如,50℃、60℃、70℃、80℃、90℃或最多100℃或更高)足够的时间(例如,1小时、2小时、3小时、4小时、5小时、6小时、7小时、8小时、9小时、15小时、20小时或最多24小时或更久)以制备该聚合物。该混合物可进一步包括溶剂,例如说明书中所公开的那些溶剂(两个非限制性实例包括THF及氯仿)。
本发明中还公开了包括光活性层的有机光伏电池。光活性层可包括本发明的聚合物中的任一种。光伏电池可包括透明或半透明基材、透明或半透明电极、光活性层及第二电极。光活性层可设置于透明/半透明电极与第二电极之间。透明/半透明电极可以是阴极且第二电极可以是阳极,或透明/半透明电极可以是阳极且第二电极可以是阴极。在某些情况下,第二电极为不透明/非透明的。例如,光伏电池可以是本体异质结光伏电池或双层光伏电池。
在另一实施方案中,公开了包括本发明的光伏电池或聚合物中的任一种的有机电子器件。有机电子器件的非限制性实例包括聚合物有机发光二极管(PLED)、有机集成电路(O-IC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机太阳能电池(O-SC)、有机发光二极管(OLED)或有机激光二极管(O-激光器)。
在再一实施方案中,公开了包括本发明的聚合物中的至少一种的光活性层。光活性层可以包括于光伏电池中或有机电子器件中。光活性层可以包括另外的材料例如p型材料(例如,聚合物或小分子)。
在本发明的再一方面中,公开了一种溶液,该溶液包含溶解于其中的本发明聚合物中的任一种。所用溶剂可以是有效溶解聚合物的溶剂。溶剂的非限制性实例包括甲苯、二甲苯、四氢萘、十氢萘、均三甲苯、正丁基苯、仲丁基丁基苯及叔丁基苯;基于芳香族卤代烃的溶剂,例如氯苯、二氯苯及三氯苯;基于饱和卤代烃的溶剂,例如四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、氯己烷、溴己烷及氯环己烷;以及醚,例如四氢呋喃及四氢吡喃。该溶液可通过以下方式沉积:刮涂、旋涂、弯液面涂覆、转印、喷墨印刷、平版印刷、丝网印刷法、浸涂、浇铸、棒涂、辊涂、线棒式涂覆、喷雾、丝网印刷、凹版印刷、柔版印刷、平版印刷、凹版印刷、点胶机涂覆、喷嘴涂覆、毛细管涂覆等。
还公开了本发明的实施方案1至38。实施方案1是聚合物,具有以下结构:
其中R1和R2各自独立地选自H、C1-30烷基、C2-30烯基、C2-30炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基,R3、R4、R9和R10各自独立地为氢或-CN,R5、R6、R7和R8各自独立地为氢、卤素、-CN、-NO2、-OH、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C3-10环烷基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基,其中卤素选自氟、氯、溴、碘和砹;满足以下条件:R5、R6、R7及R8中的任一个均非烷氧基(-OX1)或R5、R6、R7及R8中的至少三个或所有四个均为烷氧基,其中X1及X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基,且n是2至1000的整数。实施方案2是根据实施方案1所述的聚合物,其中R1及R2各自独立地为C1-30烷基、C2-30烯基或C2-30炔基。实施方案3是根据实施方案2所述的聚合物,其中C1-30烷基、C2-30烯基或C2-30炔基经独立地选自以下的1个至6个基团取代:卤素、-CN、-NO2、-OH、C1-10烷氧基、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C3-10环烷基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基,其中X1及X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基。实施方案4是根据实施方案1所述的聚合物,其中R1和R2各自独立地为C3-10环烷基、C5-10环烯基或3元至14元环杂烷基。实施方案5是根据实施方案4所述的聚合物,其中C3-10环烷基、C5-10环烯基或3元至14元环杂烷基经独立地选自以下的1个至6个基团取代:卤素、-CN、-NO2、-OH、C1-10烷氧基、-O-CH2CH2O-C1-10烷基、-O-COR7、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C1-10烷基、C2-10烯基、C2-10炔基、C6-14芳基或5元至14元杂芳基,其中X1及X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基。实施方案6是根据实施方案1所述的聚合物,其中R1和R2各自独立地为C6-14芳基或5元至14元杂芳基。实施方案7是根据实施方案6所述的聚合物,其中C6-14芳基或5元至14元杂芳基经独立地选自以下的1个至6个基团取代:卤素、-CN、-NO2、-OH、C1-10烷氧基、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基或3元至14元环杂烷基,其中X1及X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基。实施方案8是根据实施方案1所述的聚合物,其中R1及R2二者均为选自2-乙基己基、2-辛基十二烷基或2-癸基十四烷基的带支链烷基,或其中R1及R2均为具有下式的带支链烷基:
实施方案9是根据实施方案8所述的聚合物,其中R3、R4、R9和R10中的每一个都各自为氢。实施方案10是根据实施方案1至8中任一项所述的聚合物,其中R5、R6、R7和R8中的每一个都各自为氢。实施方案11是根据实施方案1至10中任一项所述的聚合物,其中n是2至100的整数。实施方案12是根据实施方案11的聚合物,其中n是2至20的整数。实施方案13是根据实施方案1至12中任一项所述的聚合物,其中所述聚合物是n型半导体聚合物。实施方案14是根据实施方案13所述的聚合物,其中所述聚合物是经掺杂剂改性的,以增强其n型性能。实施方案15是根据实施方案1至14中任一项所述的聚合物,其中所述聚合物是式(I)与式(II)的反应产物:
其中R11为选自氟、氯、溴、碘及砹的卤素,且R12和R13各自独立地为连接基团。实施方案16是根据实施方案15所述的聚合物,其中所述连接基团是C2-6烷基或亚烷基。实施方案17是根据实施方案16所述的聚合物,其中所述连接基团是2,3-二甲基丁烷。实施方案18是光伏电池,其包含光活性层,所述光活性层包含根据实施方案1至16中任一项所述的聚合物。实施方案19是根据实施方案18所述的光伏电池,其包含透明基材、透明电极、所述光活性层及第二电极,其中所述光活性层设置于所述透明电极与所述第二电极之间。实施方案20是根据实施方案19所述的光伏电池,其中所述透明电极是阴极且所述第二电极是阳极。实施方案21是根据实施方案19所述的光伏电池,其中所述透明电极是阳极且所述第二电极是阴极。实施方案22是根据实施方案18至21中任一项所述的光伏电池,其中所述第二电极不是透明的。实施方案23是根据实施方案18至22中任一项所述的光伏电池,其中光伏电池是本体异质结光伏电池。实施方案24是根据实施方案18至22中任一项所述的光伏电池,其中光伏电池是双层光伏电池。实施方案25是根据实施方案18至24中任一项所述的光伏电池,其中所述光伏电池包含在有机电子器件中。实施方案26是根据实施方案25所述的光伏电池,其中所述有机电子器件是聚合物有机发光二极管(PLED)、有机集成电路(O-IC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机太阳能电池(O-SC)或有机激光二极管(O-激光器)。实施方案27是根据实施方案18至26中任一项所述的光伏电池,其中,进一步包含p型半导体材料。实施方案28是根据实施方案27所述的光伏电池,其中所述p型半导体材料是聚合物或小分子。实施方案29是一种溶液,包含根据实施方案1至17所述的聚合物中的任一种,其中所述聚合物溶解于所述溶液中。实施方案30是一种用于在基材上制造光活性层的方法,其中所述光活性层包含根据实施方案1至17所述的聚合物中的任一种,所述方法包括将根据实施方案28所述的溶液设置于所述基材上并干燥所述溶液以形成所述光活性层。实施方案31是根据实施方案30所述的方法,其中所述溶液是通过刮涂、旋涂、弯液面涂覆、转印、喷墨印刷、平版印刷或丝网印刷方法设置于所述基材层上。实施方案32是用于制造根据实施方案1至17所述的聚合物中的任一种的方法,其包括使式(I)与式(II)在含有过渡金属的催化剂的存在下反应,其中式(I)及式(II)具有以下结构:
实施方案33是根据实施方案32所述的方法,其中将式(I)、式(II)及含有过渡金属的催化剂混合在一起以形成混合物,其中加热所述混合物,且其中产生根据实施方案1至17中任一项所述的聚合物。实施方案34是根据实施方案33所述的方法,其中所述混合物进一步包含溶解式(I)及(II)的溶剂。实施方案35是根据实施方案34所述的方法,其中所述溶剂是THF或氯仿。实施方案36是根据实施方案32至35中任一项所述的方法,其中所述含有过渡金属的催化剂是Pd(PPh3)4。实施方案37是一种电子器件,其包含根据实施方案1至17所述的聚合物中的任一种。实施方案38是根据实施方案37所述的电子器件,其中所述电子器件是聚合物有机发光二极管(PLED)、有机集成电路(O-IC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机太阳能电池(O-SC)、有机发光二极管(OLED)或有机激光二极管(O-激光器)。
术语“约”或“大约”按照本领域技术人员的理解定义为接近于,在一非限制性实施方案中,这些术语定义为在10%内、优选为在5%内、更优选在1%内且最优选在0.5%内。
在权利要求或说明书中,单数词语在与术语“包含/包括”共同使用时可能指“一个”,但也符合“一个或更多个”、“至少一个”及“一个或一个以上”的含义。
词语“包含”、“具有”、“包括”或“含有”均为包括性或开放式,且并不排除另外的未列出要素或方法步骤。
本发明的聚合物、光活性层、光伏电池及有机电子器件可“包含”整个说明书中所公开的特定成份、组份、组成等,“基本上由其组成”或“由其组成”。关于过渡词组“基本上由......组成”,在一非限制性方面中,本发明的聚合物的基本且新颖的特征为其n型半导体性能。
本发明的其他目的、特性及优势将由以下各图、详细说明及实例而变得明显。然而,应理解,这些图、详细说明及实例尽管指示本发明的具体实施方案,但仅是以图解说明方式给出而非意为具有限制性。另外,可以预期,由此详细说明,本发明精神及范畴内的变化及修改对于本领域技术人员是显见的。
附图说明
图1是纳入本发明的聚合物的有机光伏电池的图解说明。
图2是本发明的聚合物的1H-NMR。
图3是本发明的聚合物的薄膜吸光度曲线。
图4是本发明的聚合物的循环伏安图。
图5是本发明的聚合物及PC71BM的HOMO-LUMO能级。
具体实施方式
已发现新的半导体聚合物解决来自光伏电池中所用的现有有机材料的缺点。在以下部分中进一步详细论述本发明的这些及其他非限制性方面。
A.半导体聚合物
本发明的半导体聚合物基于重复的苝酰亚胺的单体单元。未经取代的苝酰亚胺的通式结构为:
已发现对乙烯基苯乙烯(或1,4二乙烯基苯)可用作连接体以使苝酰亚胺单体单元聚合,且同时制备本发明的稳定且有效的n型半导体聚合物。对乙烯基苯乙烯具有以下通式结构:
在一个非限制性方面中,这些聚合物可通过使用以下化合物(1)及(2)来制备:
化合物(1)可通过使用Heck交叉偶联技术将对乙烯基苯乙烯与含硼连接基团反应而获得(参照Dadvand,A.、Moiseev,A.G.、Sawabe,K.、Sun,W.-H.、Djukic,B.、Chung,I.、Takenobu,T.、Rosei,F.及Perepichka,D.F.(2012),MaximizingField-EffectMobilityandSolid-StateLuminescenceinOrganicSemiconductors.Angew.Chem.Int.Ed.,51:3837-3841.doi:10.1002/anie.201108184,其以引用方式并入本文中)。化合物(2)是按照类似文献程序从苝-3,4,9,10-四甲酸二酐制备(Huo,L.、Zhou,Y.及Li,Y.(2008),SynthesisandAbsorptionSpectraofn-TypeConjugatedPolymersBasedonPeryleneDiimide.Macromol.RapidCommun.,29:1444-1448.doi:10.1002/marc.200800268,其以引用方式并入本文中)。然后可以使用Suzuki交叉偶联技术将化合物(1)及(2)在一起反应(参照Zhou,E.、Cong,J.、Wei,Q.、Tajima,K.、Yang,C.及Hashimoto,K.(2011),All-PolymerSolarCellsfromPeryleneDiimideBasedCopolymers:MaterialDesignandPhaseSeparationControl.Angew.Chem.Int.Ed.,50:2799-2803.doi:10.1002/anie.201005408,其以引用方式并入本文中)以制备本发明的特定聚合物(P-2)。可以使用以下反应方案1:
反应方案1
如本发明的其他部分(例如,本发明的发明内容及权利要求,其以引用方式并入本文中)中所解释的,可以使用以上反应方案来制备具有各种R基团的另外的聚合物。举例来说,可以使用以下通式反应方案2,其中R基团为如先前所定义的那些基团:
反应方案2
B.有机光伏电池
本发明的半导体聚合物可用于有机光伏电池。图1是可纳入本发明的聚合物的非限制性有机光伏电池的截面图。有机光伏电池(1)可包括透明基材(10)、前电极(11)、光活性层(12)及背电极(13)。本领域技术人员已知的另外的材料、层及涂层(未显示)可与光伏电池(1)一起使用,其中一些在下文描述。
一般而言,有机光伏电池(1)可通过以下方式将光转化成可用能量:(a)光子吸收以产生激子;(b)激子扩散;(c)电荷转移;及(d)电荷传输至电极。关于(a),激子是通过光活性层(12)的光子吸收产生的,光活性层(12)可以是p型有机半导体材料和n型有机半导体材料的混合物(例如,本体异质结)或可以是彼此相邻的单独的p型层和n型层(即双层异质结)。对于(b),所生成的激子扩散至p-n结。然后在(c)中,激子分离为电子及空穴。对于(d),电子及空穴传输至电极(11)及(13)并用于电路。
1.基材(10)
基材(10)可用作载体。对于有机光伏电池,其通常为透明或半透明的,其可让光有效地进入电池中。它通常由不容易被热或有机溶剂改变或降解的材料制得,且如上所述地,具有优良的光学透明度。这些材料的非限制性实例包括无机材料(例如无碱玻璃及石英玻璃)、聚合物(例如聚乙烯、聚对苯二甲酸乙二酯、聚对萘二甲酸乙二酯、聚酰亚胺、聚酰胺、聚醚酰亚胺、聚酰胺酰亚胺、液晶聚合物及环烯烃聚合物)、硅以及金属。
2.前电极(11)及背电极(13)
前电极(11)根据电路的设定可用作阴极或阳极。其堆叠于基材(10)上。前电极(11)是由透明或半透明导电材料制得。通常,前电极(11)是通过使用这样的材料形成膜(例如,真空沉积、溅镀、离子镀覆、镀覆、涂覆等)而获得。透明或半透明导电材料的非限制性实例包括金属氧化物膜、金属膜及导电聚合物。可用于形成膜的金属氧化物的非限制性实例包括氧化铟、氧化锌、氧化锡、及其复合物例如铟掺杂的氧化锡(ITO)、氟掺杂的氧化锡(FTO)及氧化铟锌的膜。可用于形成膜的金属的非限制性实例包括金、铂、银及铜。导电聚合物的非限制性实例包括聚苯胺及聚噻吩。前电极(11)的膜的厚度通常在30nm与300nm之间。若膜厚度小于30nm,则可能减小导电性并增加电阻,这会导致光电转化效率降低。若膜厚度大于300nm,则透光率可能降低。而且,前电极(11)的薄层电阻通常为10Ω/□或低于10Ω/□。此外,前电极(11)可以是单层或由各自具有不同功函数的材料形成的层合层。
背电极(13)根据电路的设定可用作阴极或阳极。此电极(13)可堆叠于光活性层(12)上。用于背电极(13)的材料是导电的。这些材料的非限制性实例包括金属、金属氧化物及导电聚合物(例如,聚苯胺、聚噻吩等),例如上文在前电极(11)的上下文中所论述的那些。当使用具有高功函数的材料形成前电极(11)时,则可由具有低功函数的材料制得背电极(13)。具有低功函数的材料的非限制性实例包括Li、In、Al、Ca、Mg、Sm、Tb、Yb、Zr、Na、K、Rb、Cs、Ba及其合金。背电极(13)可以是单层或由各自具有不同功函数的材料形成的层合层。此外,其可以是具有低功函数的材料中的一种或一种以上的合金,且至少一种选自金、银、铂、铜、锰、钛、钴、镍、钨及锡。该合金的实例包括锂-铝合金、锂-镁合金、锂-铟合金、镁-银合金、镁-铟合金、镁-铝合金、铟-银合金及钙-铝合金。背电极(13)的膜厚度可以是1nm至1000nm或10nm至500nm。若膜厚度过小,则电阻可能极大且所生成的电荷可能不能充分传送至外电路。
在一些实施例中,前电极(11)及背电极(13)可进一步涂覆有空穴传输层或电子传输层(图1中未显示)以增加效率并防止有机光伏电池(1)的短路。空穴传输层及电子传输层可***电极与光活性层(12)之间。可用于空穴传输层的材料的非限制性实例包括基于聚噻吩的聚合物例如PEDOT/PSS(聚(3,4-亚乙基二氧噻吩)-聚(苯乙烯磺酸))、及有机导电聚合物例如聚苯胺及聚吡咯。空穴传输层的膜厚度可以是20nm至100nm。若膜厚度过薄,则电极短路更容易发生。若膜厚度过厚,则膜电阻大,所生成的电流可能受限,且可能降低光学转化效率。至于电子传输层,其可通过阻挡空穴并更有效地传输电子而起作用。可制得电子传输层的材料类型的非限制性实例包括金属氧化物(例如,非晶氧化钛)。当使用氧化钛时,膜厚度的范围可在5nm至20nm。若膜厚度过薄,则可降低空穴阻挡效应并因此使所生成的激子在激子解离成电子及空穴之前失活。相比之下,当膜厚度过厚时,膜电阻大,所生成的电流受限,从而导致光学转化效率降低。
3.光活性层(12)
光活性层(12)可***前电极(11)与背电极(13)之间。在一种情况下,光活性层(12)可以是本体异质结型层,则本发明的聚合物被与第二半导体材料(例如,第二聚合物或小分子)混合且在该层(12)内发生微相分离。可选地,光活性层(12)可以是双层异质结型层,则本发明的聚合物形成一层而第二光活性层与其相邻。在任一情况下,层(12)都将包括p型及n型有机半导体二者,从而可让电子流动。此外,用于指定的光伏电池,可以存在多个光活性层(例如,2个、3个、4个或更多个)。由于本发明的聚合物为n型聚合物,故可添加p型材料,例如p型聚合物及p型小分子,这两者均为本领域技术人员所已知。这些材料的非限制性实例包括聚苯撑乙烯、聚-3-烷基噻吩、并五苯及铜酞菁。
光活性层可通过获得包括溶剂及溶解于其中的本发明的聚合物的溶液来沉积。这些溶剂的非限制性实例包括基于不饱和烃的溶剂,例如甲苯、二甲苯、四氢萘、十氢萘、均三甲苯、正丁基苯、仲丁基丁基苯及叔丁基苯;基于芳香族卤代烃的溶剂,例如氯苯、二氯苯及三氯苯;基于饱和卤代烃的溶剂,例如四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、氯己烷、溴己烷及氯环己烷;及醚,例如四氢呋喃及四氢吡喃。该溶液可通过以下方式沉积:刮刀涂覆、旋涂、弯液面涂覆、转印、喷墨印刷、平版印刷、丝网印刷方法、浸涂、浇铸、棒涂、辊涂、线棒式涂覆、喷雾、丝网印刷、凹版印刷、柔版印刷、平版印刷、凹版印刷、点胶机涂覆、喷嘴涂覆、毛细管涂覆等。
实施例
将通过具体实施例更详细地阐述本发明。提出以下实施例仅用于说明性目的,而非意为以任何方式限制本发明。本领域技术人员能够容易地识别各种非关键参数,可以对这些参数进行改变或修改以获得基本上相同的结果。
实施例1
(利用反应方案1合成P-2)
使用反应方案1合成P-2:将Pd(PPh3)4(3.8mg,0.00329mmol)、2.0MNa2CO3(aq)(3.79mL)、1,4-双((E)-2-(4,4,5,5-四甲基-1,3,2-二氧杂环硼戊烷-2-基)乙烯基)苯1(30mg,0.0785mmol)(通过1,4-二碘苯的Heck偶联以定量产率制备;光谱性质与先前所报导的一致(参照T.Lee、C.Baik、I.Jung、K.H.Song、S.Kim、D.Kim、S.O.Kang及J.Ko,Organometallics2004,23,4569)),及PDI单体2(96mg,0.0786mmol)的混合物在90℃、氩气气氛下于THF(6.28mL)中搅拌。该反应进行24h,此时添加另外的Pd(PPh3)4(8.0mg,0.00693mmol)及氩气鼓泡的THF(5.00mL)。该反应再继续进行24h。在冷却至室温后将该混合物与水(100mL)合并。将沉淀物通过过滤分离,并用蒸馏水洗涤,然后通过索氏萃取(Soxhletextraction)使用甲醇、己烷及THF纯化。浓缩THF部分,从而得到呈深紫色固体的P-2(55mg,60%)。在这些条件下合成的P-2具有Mw=9.9kDa、Mn=5.6kDa及Mn/Mw=1.77。图2显示1H-NMR(400MHz,CDCl3):δ8.66(m,6H),7.68(m,8H),4.15(br,4H),2.02(br,2H),1.48-1.03(m,80H),0.78(br,12H)。Mn=5600Da,PDI=1.77。以薄膜形式分析P-2的吸光度曲线,该薄膜通过将聚合物旋涂至玻璃表面上所获得。P-2是在可见光谱内的强光吸收剂,吸光度在约709nm处开始且最大值在389nm及550nm处(图3)。以薄膜形式分析P-2的电化学性质,该薄膜通过将聚合物旋涂至ITO表面上所获得。电化学分析证实P-2是稳定的电子受体(图4)。
实施例2
(HOMO及LUMO分析)
将聚合物P-2的薄膜旋涂至ITO电极的表面上,并在0.1MN(C4H9)4PF6乙腈溶液中进行研究。除了在0.67V处开始的氧化外,观测到在-1.11V(相对于fc/fc+)处开始的可逆还原。所获得的氧化及还原值分别对应于-5.50eV及-3.79eV的HOMO及LUMO值,HOMO-LUMO间隙为1.78eV。P-2是太阳能电池材料的优良候选。与已经市售的最普遍的n型太阳能电池材料之一PC71BM相比,P-2具有较低的带隙且在可见光谱范围更强地吸收光(参照表1)(图5)。此外,P-2高度溶于常见有机溶剂(例如THF或氯仿),是可溶液处理的物质。
表1
(P-2与PC71BM之间的比较分析)
*PC71BM的数据获得自网页http://www.sigmaaldrich.com/catalog/product/aldrich/684465?lang=en®ion=US
Claims (38)
1.一种聚合物,具有以下结构:
其中
R1及R2各自独立地选自H、C1-30烷基、C2-30烯基、C2-30炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基,
R3、R4、R9和R10各自独立地为氢或-CN,
R5、R6、R7和R8各自独立地为氢、卤素、-CN、-NO2、-OH、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C3-10环烷基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基,其中卤素选自氟、氯、溴、碘和砹;满足如下条件:R5、R6、R7和R8中的任一个均非烷氧基(-OX1),或R5、R6、R7和R8中的至少三个或所有四个均为烷氧基,
其中
X1及X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基,且
n是2至1000的整数。
2.根据权利要求1所述的聚合物,其中R1和R2各自独立地为C1-30烷基、C2-30烯基或C2-30炔基。
3.根据权利要求2所述的聚合物,其中C1-30烷基、C2-30烯基或C2-30炔基经独立地选自以下的1个至6个基团取代:卤素、-CN、-NO2、-OH、C1-10烷氧基、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C3-10环烷基、3元至14元环杂烷基、C6-14芳基或5元至14元杂芳基,
其中
X1和X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基。
4.根据权利要求1所述的聚合物,其中R1和R2各自独立地为C3-10环烷基、C5-10环烯基或3元至14元环杂烷基。
5.根据权利要求4所述的聚合物,其中C3-10环烷基、C5-10环烯基或3元至14元环杂烷基经独立地选自以下的1个至6个基团取代:卤素、-CN、-NO2、-OH、C1-10烷氧基、-O-CH2CH2O-C1-10烷基、-O-COR7、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C1-10烷基、C2-10烯基、C2-10炔基、C6-14芳基或5元至14元杂芳基,
其中
X1和X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基。
6.根据权利要求1所述的聚合物,其中R1和R2各自独立地为C6-14芳基或5元至14元杂芳基。
7.根据权利要求6所述的聚合物,其中,C6-14芳基或5元至14元杂芳基经独立地选自以下的1个至6个基团取代:卤素、-CN、-NO2、-OH、C1-10烷氧基、-O-CH2CH2O-C1-10烷基、-O-COX1、-S-C1-10烷基、-NH2、-NHX1、-NX1X2、-NH-COX1、-COOH、-COORS、-CONH2、-CONHX1、-CONX1X2、-CO-H、-COX1、C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基或3元至14元环杂烷基,
其中
X1和X2各自独立地为C1-10烷基、C2-10烯基、C2-10炔基、C3-10环烷基、C5-10环烯基、3元至14元环杂烷基、C6-14芳基及5元至14元杂芳基。
8.根据权利要求1所述的聚合物,其中R1和R2二者均为选自2-乙基己基、2-辛基十二烷基或2-癸基十四烷基的带支链烷基,或者其中R1和R2均为具有下式的带支链烷基:
9.根据权利要求8所述的聚合物,其中R3、R4、R9和R10中的每一个都各自为氢。
10.根据权利要求1至8中任一项所述的聚合物,其中R5、R6、R7和R8中的每一个都各自为氢。
11.根据权利要求1至10中任一项所述的聚合物,其中n是2至100的整数。
12.根据权利要求11所述的聚合物,其中n是2至20的整数。
13.根据权利要求1至12中任一项所述的聚合物,其中所述聚合物是n型半导体聚合物。
14.根据权利要求13所述的聚合物,其中所述聚合物是用掺杂剂改性的,以增强其n型性能。
15.根据权利要求1至14中任一项所述的聚合物,其中所述聚合物是式(I)与式(II)的反应产物:
其中
R11为选自氟、氯、溴、碘和砹的卤素,且
R12和R13各自独立地为连接基团。
16.根据权利要求15所述的聚合物,其中所述连接基团是C2-6烷基或亚烷基。
17.根据权利要求16所述的聚合物,其中所述连接基团是2,3-二甲基丁烷。
18.一种光伏电池,其包含光活性层,所述光活性层包含根据权利要求1至16中任一项所述的聚合物。
19.根据权利要求18所述的光伏电池,其包含透明基材、透明电极、所述光活性层和第二电极,其中所述光活性层设置于所述透明电极与所述第二电极之间。
20.根据权利要求19所述的光伏电池,其中所述透明电极是阴极且所述第二电极是阳极。
21.根据权利要求19所述的光伏电池,其中所述透明电极是阳极且所述第二电极是阴极。
22.根据权利要求18至21中任一项所述的光伏电池,其中所述第二电极不是透明的。
23.根据权利要求18至22中任一项所述的光伏电池,其中光伏电池是本体异质结光伏电池。
24.根据权利要求18至22中任一项所述的光伏电池,其中光伏电池是双层光伏电池。
25.根据权利要求18至24中任一项所述的光伏电池,其中所述光伏电池包含在有机电子器件中。
26.根据权利要求25所述的光伏电池,其中所述有机电子器件是聚合物有机发光二极管(PLED)、有机集成电路(O-IC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机太阳能电池(O-SC)或有机激光二极管(O-激光器)。
27.根据权利要求18至26中任一项所述的光伏电池,其还包含p型半导体材料。
28.根据权利要求27所述的光伏电池,其中所述p型半导体材料是聚合物或小分子。
29.一种溶液,其包含根据权利要求1至17所述的聚合物中的任一种,其中所述聚合物溶解于所述溶液中。
30.一种用于在基材上制造光活性层的方法,其中所述光活性层包含根据权利要求1至17所述的聚合物中的任一种,所述方法包括将根据权利要求28所述的溶液设置于所述基材上并干燥所述溶液以形成所述光活性层。
31.根据权利要求30所述的方法,其中所述溶液是通过刮刀涂覆、旋涂、弯液面涂覆、转印、喷墨印刷、平版印刷或丝网印刷方法设置于基材层上的。
32.一种用于制造根据权利要求1至17所述的聚合物中的任一种的方法,其包括使式(I)与式(II)在含有过渡金属的催化剂的存在下反应,其中式(I)及式(II)具有以下结构:
33.根据权利要求32所述的方法,其中将式(I)、式(II)及所述含有过渡金属的催化剂混合在一起以形成混合物,其中加热所述混合物,且其中产生根据权利要求1至17中任一项所述的聚合物。
34.根据权利要求33所述的方法,其中所述混合物还包含溶解式(I)和(II)的溶剂。
35.根据权利要求34所述的方法,其中所述溶剂是THF或氯仿。
36.根据权利要求32至35中任一项所述的方法,其中所述含有过渡金属的催化剂是Pd(PPh3)4。
37.一种电子器件,其包含根据权利要求1至17所述的聚合物中的任一种。
38.根据权利要求37所述的电子器件,其中所述电子器件是聚合物有机发光二极管(PLED)、有机集成电路(O-IC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机太阳能电池(O-SC)、有机发光二极管(OLED)或有机激光二极管(O-激光器)。
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BRIAN A. GREGG等: "Doping Molecular Semiconductors: n-Type Doping of a Liquid Crystal Perylene Diimide", 《J. AM. CHEM. SOC.》 * |
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