公开(公告)号：US08598304B2

公开(公告)日：2013-12-03

申请号：US13002392

申请日：2009-06-25

申请人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Miaoyin Liu ,  Dirk Beckmann ,  Ralph Rieger

发明人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Miaoyin Liu ,  Dirk Beckmann ,  Ralph Rieger

IPC分类号： C08G75/00

CPC分类号： H01L51/0036 ,  C07D495/04 ,  C08G61/126 ,  H01B1/127 ,  H01L51/0043 ,  H01L51/0074 ,  H01L51/0541 ,  H01L51/0545 ,  Y02E10/549

摘要： Poly(5,5′-bis(thiophen-2-yl)-benzo[2,1-b;3,4-b′]dithiophene) comprising as repeating units the group of the formula (I) wherein R is independently selected from a) a C1-20 alkyl group, b) a C2-20 alkenyl group, c) a C2-20 alkynyl group, d) a C1-20 alkoxy group, e) a —Y—C3-10 cycloalkyl group, f) a —Y—C6-14 aryl group, g) a —Y-3-12 membered cycloheteroalkyl group, or h) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 R1 groups, R1 is independently selected from a) a S(O)m—C1-20 alkyl group, b) a S(O)m—OC1-20 alkyl group, c) a S(O)m—OC6-14 aryl group, d) a C(O)—OC1-20 alkyl group, e) a C(O)—OC6-14 aryl group, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C3-10 cycloalkyl group, k) a C6-14 aryl group, l) a 3-12 membered cycloheteroalkyl group, or m) a 5-14 membered heteroaryl group, Y is independently selected from a divalent C1-6 alkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2, and having a number average molecular weight Mn in the range of from 5,000 to 200,000 g/mol.

摘要翻译： 包括作为重复单元的式（I）基团，其中R独立地被选择的聚（5,5'-双（噻吩-2-基） - 苯并[2,1-b; 3,4-b']二噻吩） 从a）C 1-20烷基，b）C 2-20烯基，c）C 2-20炔基，d）C 1-20烷氧基，e）-Y-C 3-10环烷基，f ）-Y-C 6-14芳基，g）a -Y-3-12元环杂烷基，或h）-Y-5-14元杂芳基，其中C 1-20烷基，C 2 -20链烯基，C2-20炔基，C3-10环烷基，C6-14芳基，3-12元环杂烷基和5-14元杂芳基任选被1-4个R1 基团，R 1独立地选自a）S（O）m -C 1-20烷基，b）S（O）m OC 1-7-20烷基，c）S（O）m -C 0-6-14芳基 基团，d）C（O）-OC 1-20烷基，e）C（O）-OC 6-14芳基，f）C 1-20烷基，g）C 2-20烯基，h） C 20-20炔基，i）C 1-20烷氧基，j）C 3-10环烷基，k）C 6-14 芳基，l）3-12元环杂烷基，或m）5-14元杂芳基，Y独立地选自二价C 1-6烷基或共价键; m独立地选自0,1或2，数均分子量Mn在5,000至200,000g / mol的范围内。

公开(公告)号：US20110168264A1

公开(公告)日：2011-07-14

申请号：US13002392

申请日：2009-06-25

申请人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Miaoyin Liu ,  Dirk Beckmann ,  Ralph Rieger

发明人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Miaoyin Liu ,  Dirk Beckmann ,  Ralph Rieger

IPC分类号： H01L51/46 ,  H01L51/30 ,  H01L51/54 ,  C08G75/06 ,  C08L81/02

CPC分类号： H01L51/0036 ,  C07D495/04 ,  C08G61/126 ,  H01B1/127 ,  H01L51/0043 ,  H01L51/0074 ,  H01L51/0541 ,  H01L51/0545 ,  Y02E10/549

摘要： Poly(5,5′-bis(thiophen-2-yl)-benzo[2,1-b;3,4-b′]dithiophene) comprising as repeating units the group of the formula (I) wherein R is independently selected from a) a C1-2O alkyl group, b) a C2-20 alkenyl group, c) a C2-20 alkynyl group, d) a C1-20 alkoxy group, e) a —Y—C3-10 cycloalkyl group, f) a —Y—C6-14 aryl group, g) a —Y-3-12 membered cycloheteroalkyl group, or h) a —Y-5-14 membered het-eroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 R1 groups, R1 is independently selected from a) a S(O)m—C1-20 alkyl group, b) a S(O)m—OC1-20 alkyl group, c) a S(O)m—OC6-14 aryl group, d) a C(O)—OC1-20 alkyl group, e) a C(O)—OC6-14 aryl group, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C3-10 cycloalkyl group, k) a C6-14 aryl group, I) a 3-12 membered cycloheteroalkyl group, or m) a 5-14 membered heteroaryl group, Y is independently selected from a divalent C1-6 alkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2, and having a number average molecular weight Mn in the range of from 5,000 to 200,000 g/mol.

摘要翻译： 包括作为重复单元的式（I）基团，其中R独立地被选择的聚（5,5'-双（噻吩-2-基） - 苯并[2,1-b; 3,4-b']二噻吩） 从a）C1-2O烷基，b）C2-20烯基，c）C2-20炔基，d）C1-20烷氧基，e）-Y-C3-10环烷基，f ）a -Y-C 6-14芳基，g）-Y-3-12元环杂烷基，或h）-Y-5-14元环芳基，其中每个C 1-20烷基， C2-20烯基，C2-20炔基，C3-10环烷基，C6-14芳基，3-12元环杂烷基和5-14元杂芳基任选被1- 4个R 1基团，R 1独立地选自a）S（O）m -C 1-20烷基，b）S（O）m OC 1-7-20烷基，c）S（O）m OC 1-6 - 14芳基，d）C（O）-OC1-20烷基，e）C（O）-OC6-14芳基，f）C1-20烷基，g）C2-20烯基， h）C 20-20炔基，i）C 1-20烷氧基，j）C 3-10环烷基 烷叉基，k）C 6-14芳基，I）3-12元环杂烷基或m）5-14元杂芳基，Y独立地选自二价C 1-6烷基或共价键 ; m独立地选自0,1或2，数均分子量Mn在5,000至200,000g / mol的范围内。

公开(公告)号：US20110155248A1

公开(公告)日：2011-06-30

申请号：US13002208

申请日：2009-06-25

申请人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Peng Gao ,  Dirk Beckmann ,  Xinliang Feng ,  Hoi Nok Tsao

发明人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Peng Gao ,  Dirk Beckmann ,  Xinliang Feng ,  Hoi Nok Tsao

IPC分类号： C07D333/52 ,  H01B1/12 ,  H01L51/30 ,  H01L51/46 ,  H01L51/54

CPC分类号： H01L51/0074 ,  C07D495/22 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1092 ,  G02B2006/12069 ,  H01L51/0545 ,  H01L51/5048 ,  H05B33/10 ,  H05B33/14 ,  Y02E10/549

摘要： Dithienobenzodithiophenes of general formula (I) in which R1 to R6 are each independently selected from a) H, b) halogen, c) —CN, d) —NO2, e) —OH, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C1-20 alkylthio group, k) a C1-20 haloalkyl group, I) a —Y—C3-10 cycloalkyl group, m) a —Y—C6-14 aryl group, n) a —Y-3-12 membered cyclo-heteroalkyl group, or o) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cyc-loheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 R7 groups, wherein R1 and R3 and R2 and R4 may also together form an aliphatic cyclic moiety, Y is independently selected from divalent a C1-6 alkyl group, a divalent C1-6 haloalkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2. The invention also relates to the use of the dithienobenzodithiophenes according to any of claims 1 to 4 as semiconductors or charge transport materials, as thin-film transistors (TFTs), or in semiconductor components for organic light-emitting diodes (OLEDs), for photovoltaic components or in sensors, as an electrode material in batteries, as optical waveguides or for electrophotography applications.

摘要翻译： 通式（I）的二噻吩并苯并二噻吩，其中R 1至R 6各自独立地选自a）H，b）卤素，c）-CN，d）-NO 2，e）-OH，f）C 1-20烷基， ）C2-20烯基，h）C2-20炔基，i）C1-20烷氧基，j）C1-20烷硫基，k）C1-20卤代烷基，I）a -Y- C3-10环烷基，m）-Y-C6-14芳基，n）a -Y-3-12元环杂烷基，或o）-Y-5-14元杂芳基，其中各 C 1-20烷基，C 2-20烯基，C 2-20炔基，C 3-10环烷基，C 6-14芳基，3-12元环 - 卤杂烷基和5-14 任选被1-4个R 7基团取代，其中R 1和R 3以及R 2和R 4也可以一起形成脂族环状部分，Y独立地选自二价C 1-6烷基，二价C 1-6卤代烷基 ，或共价键; 并且m独立地选自0,1或2.本发明还涉及根据权利要求1至4中任一项所述的二噻吩并苯并噻吩作为半导体或电荷传输材料，作为薄膜晶体管（TFT）或半导体 用于有机发光二极管（OLED）的组件，用于光伏组件或传感器，作为电池中的电极材料，作为光波导或电子照相应用。

公开(公告)号：US08367717B2

公开(公告)日：2013-02-05

申请号：US13002208

申请日：2009-06-25

申请人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Peng Gao ,  Dirk Beckmann ,  Xinliang Feng ,  Hoi Nok Tsao

发明人： Marcel Kastler ,  Silke Koehler ,  Klaus Muellen ,  Peng Gao ,  Dirk Beckmann ,  Xinliang Feng ,  Hoi Nok Tsao

IPC分类号： A61K31/38 ,  C07D333/50

CPC分类号： H01L51/0074 ,  C07D495/22 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1092 ,  G02B2006/12069 ,  H01L51/0545 ,  H01L51/5048 ,  H05B33/10 ,  H05B33/14 ,  Y02E10/549

摘要： Dithienobenzodithiophenes of general formula (I) in which R1 to R6 are each independently selected from a) H, b) halogen, c) —CN, d) —NO2, e) —OH, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C1-20 alkylthio group, k) a C1-20 haloalkyl group, I) a —Y—C3-10 cycloalkyl group, m) a —Y—C6-14 aryl group, n) a —Y-3-12 membered cyclo-heteroalkyl group, or o) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cyc-loheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 R7 groups, wherein R1 and R3 and R2 and R4 may also together form an aliphatic cyclic moiety, Y is independently selected from divalent a C1-6 alkyl group, a divalent C1-6 haloalkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2. The invention also relates to the use of the dithienobenzodithiophenes according to any of claims 1 to 4 as semiconductors or charge transport materials, as thin-film transistors (TFTs), or in semiconductor components for organic light-emitting diodes (OLEDs), for photovoltaic components or in sensors, as an electrode material in batteries, as optical waveguides or for electrophotography applications.

摘要翻译： 通式（I）的二噻吩并苯并二噻吩，其中R 1至R 6各自独立地选自a）H，b）卤素，c）-CN，d）-NO 2，e）-OH，f）C 1-20烷基， ）C2-20烯基，h）C2-20炔基，i）C1-20烷氧基，j）C1-20烷硫基，k）C1-20卤代烷基，I）a -Y- C3-10环烷基，m）-Y-C6-14芳基，n）a -Y-3-12元环杂烷基，或o）-Y-5-14元杂芳基，其中各 C 1-20烷基，C 2-20烯基，C 2-20炔基，C 3-10环烷基，C 6-14芳基，3-12元环 - 卤杂烷基和5-14 任选被1-4个R 7基团取代，其中R 1和R 3以及R 2和R 4也可以一起形成脂族环状部分，Y独立地选自二价C 1-6烷基，二价C 1-6卤代烷基 ，或共价键; 并且m独立地选自0,1或2.本发明还涉及根据权利要求1至4中任一项所述的二噻吩并苯并噻吩作为半导体或电荷传输材料，作为薄膜晶体管（TFT）或半导体 用于有机发光二极管（OLED）的组件，用于光伏组件或传感器，作为电池中的电极材料，作为光波导或电子照相应用。

公开(公告)号：US20110240973A1

公开(公告)日：2011-10-06

申请号：US13074725

申请日：2011-03-29

申请人： Mathias Dueggeli ,  Ralph Reiger ,  Klaus Muellen ,  Natalia Chebotareva ,  Dirk Beckmann

发明人： Mathias Dueggeli ,  Ralph Reiger ,  Klaus Muellen ,  Natalia Chebotareva ,  Dirk Beckmann

IPC分类号： H01L51/30 ,  C08G73/06 ,  C08G75/06 ,  H01B1/12 ,  H01L51/40

CPC分类号： H01L51/0036 ,  B82Y10/00 ,  C08G61/123 ,  C08G61/126 ,  C08G73/0688 ,  C08G2261/124 ,  C08G2261/1412 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/334 ,  C08G2261/362 ,  C08G2261/411 ,  H01L51/0047 ,  H01L51/0545 ,  H01L51/4253 ,  Y02E10/549

摘要： Disclosed is an organic semiconductor material, layer or component, comprising a copolymer of the formula wherein v and w each generally are from the range 4 to 1000; A is a benzodithiophene repeating unit of the formula II or III and COM is selected from certain arylene-type repeating units, and combinations thereof, with further symbols as defined in the claims. The present copolymers, as well as composites thereof, may be used as semiconductor in the preparation of electronic devices such as photodiodes, organic field effect transistors and especially organic photovoltaic devices such as solar cells.

摘要翻译： 公开了一种有机半导体材料，层或组分，其包含下式的共聚物，其中v和w各自通常为4至1000; A是式II或III的苯并二噻吩重复单元，并且COM选自某些亚芳基型重复单元及其组合，以及权利要求中定义的其它符号。 本发明的共聚物及其复合材料可用作制备诸如光电二极管，有机场效应晶体管以及特别是有机光伏器件如太阳能电池的电子器件的半导体。

公开(公告)号：US08729220B2

公开(公告)日：2014-05-20

申请号：US13074725

申请日：2011-03-29

申请人： Mathias Dueggeli ,  Ralph Reiger ,  Klaus Muellen ,  Natalia Chebotareva ,  Dirk Beckmann

发明人： Mathias Dueggeli ,  Ralph Reiger ,  Klaus Muellen ,  Natalia Chebotareva ,  Dirk Beckmann

IPC分类号： C08G75/00

CPC分类号： H01L51/0036 ,  B82Y10/00 ,  C08G61/123 ,  C08G61/126 ,  C08G73/0688 ,  C08G2261/124 ,  C08G2261/1412 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/334 ,  C08G2261/362 ,  C08G2261/411 ,  H01L51/0047 ,  H01L51/0545 ,  H01L51/4253 ,  Y02E10/549

摘要： An organic semiconductor material, layer or component, comprising a copolymer of the formula wherein v and w each generally are from the range 4 to 1000; A is a benzodithiophene repeating unit of the formula II or III and COM is selected from certain arylene-type repeating units, and combinations thereof. The present copolymers, as well as composites thereof, may be used as semiconductor in the preparation of electronic devices such as photodiodes, organic field effect transistors and especially organic photovoltaic devices such as solar cells.

摘要翻译： 一种有机半导体材料，层或组分，其包含下式的共聚物，其中v和w各自通常为4至1000; A是式II或III的苯并二噻吩重复单元，COM选自某些亚芳基型重复单元及其组合。 本发明的共聚物及其复合材料可用作制备诸如光电二极管，有机场效应晶体管以及特别是有机光伏器件如太阳能电池的电子器件的半导体。