CN102892807A - 用于有机半导体器件的二酮基吡咯并吡咯聚合物 - Google Patents
用于有机半导体器件的二酮基吡咯并吡咯聚合物 Download PDFInfo
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- CN102892807A CN102892807A CN2011800246345A CN201180024634A CN102892807A CN 102892807 A CN102892807 A CN 102892807A CN 2011800246345 A CN2011800246345 A CN 2011800246345A CN 201180024634 A CN201180024634 A CN 201180024634A CN 102892807 A CN102892807 A CN 102892807A
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 29
- 229920000642 polymer Polymers 0.000 title abstract description 23
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title 1
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- MNALLGNMYJQSHP-UHFFFAOYSA-N 1,4-bis(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound CCCCCCCCC(CCCCCC)CN1C(=O)C2=C(C=3SC(Br)=CC=3)N(CC(CCCCCC)CCCCCCCC)C(=O)C2=C1C1=CC=C(Br)S1 MNALLGNMYJQSHP-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/125—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one oxygen atom in the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
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Abstract
本发明涉及包含一个或多个式(I)的(重复)单元的聚合物或式(II)或(III)的聚合物及其作为有机器件中的有机半导体的用途,尤其是用于有机光伏器件(太阳能电池)及光电二极管或用于含有二极管和/或有机场效应晶体管的器件中。本发明聚合物在有机溶剂中具有优良溶解性且具有优良成膜性能。此外,在本发明聚合物用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时,可观察到高能量转换效率、优良场效应迁移率、良好开/关电流比和/或优良稳定性。
Description
本发明涉及包含一个或多个式的(重复)单元的聚合物或式的聚合物,及其作为有机半导体在有机器件,尤其是有机光伏器件(太阳能电池)和光电二极管或含有二极管和/或有机场效应晶体管的器件中的用途。本发明聚合物在有机溶剂中具有优良溶解性且具有优良成膜性能。此外,在本发明聚合物用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时,可观察到高能量转换效率、优良场效应迁移率、良好开/关电流比和/或优良稳定性。
WO 05/049695公开基于二酮基吡咯并吡咯(DPP)的聚合物及其在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)或有机激光二极管中的用途,但未公开式I的基于DPP的特定聚合物。
优选聚合物包含下式重复单元
R1和R2彼此独立地为可被一个或多个氧原子间隔的C1-C25烷基,尤其是C4-C12烷基,且Ar1和Ar2彼此独立地为下式的基团:
R6为氢、C1-C18烷基或C1-C18烷氧基,且R32为甲基、Cl或OMe,且R8为H、C1-C18烷基或由E取代和/或被D间隔的C1-C18烷基,尤其是被-O-间隔的C1-C18烷基。
EP2034537A2涉及包含半导体层的薄膜晶体管器件,该半导体层包含含有由下式表示的化学结构的化合物:其中X各自独立地选自S、Se、O和NR″,R″各自独立地选自氢、任选地经取代的烃和含杂原子的基团,Z各自独立地为任选地经取代的烃、含杂原子的基团和卤素中的一个,d为至少为1的数,e为0-2的数;a代表至少为1的数;b代表0-20的数;且
n代表至少为1的数。
其中,明确公开下列均聚物:
其中n为重复单元的数量且可为约2至约5000,R″′、R″″和R″″′可为相同或不同取代基,且其中该取代基独立地选自任选地经取代的烃基团和含杂原子的基团。
本发明不涉及均聚物,尤其是式(22)、(23)、(24)、(25)、(34)、(35)、(36)、(37)、(44)、(45)、(46)和(47)的均聚物,其明确公开于EP2034537A2中。
EP2075274A1公开含有高度共面重复单元的可溶性聚噻吩衍生物。TPT(噻吩-亚苯基-噻吩)单元的共面特性改进分子内结合和分子间π-π相互作用的程度。
本发明目的为提供如下聚合物,在用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时,该聚合物显示高能量转换效率、优良场效应迁移率、良好开/关电流比和/或优良稳定性。
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1。r=0.985-0.005,s=0.005-0.985,t=0.005-0.985,u=0.005-0.985,且其中r+s+t+u=1,
A为式的基团,其中
a'为整数1或2,
b为整数1或2,
c为0或整数1或2,
d为0或整数1或2,
e为0或整数1或2,
f为0或整数1或2,
R1和R2可相同或不同且选自氢、C1-C100烷基、-COOR203;C1-C100烷基,其经一个或多个卤原子、羟基、硝基、-CN或C6-C18芳基取代和/或被-O-、-COO-、-OCO-或-S-间隔;C7-C100芳基烷基、氨基甲酰基;C5-C12环烷基,其可经C1-C8烷基和/或C1-C8烷氧基取代1-3次;C6-C24芳基,尤其是苯基或1-或2-萘基,其可经C1-C8烷基、C1-C8硫代烷氧基和/或C1-C8烷氧基取代1-3次;或五氟苯基,R203为C1-C50烷基,尤其是C4-C25烷基;
Ar1和Ar1'彼此独立地为
R99、R104和R104'彼此独立地为氢、卤素,尤其是F;或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;C7-C25芳基烷基或C1-C25烷氧基,
R105、R105′、R106和R106'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳基烷基或C1-C18烷氧基;
R107为C7-C25芳基烷基、C6-C18芳基;经C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C25烷基;被-O-或-S-间隔的C1-C25烷基;或-COOR119;
R116为氢、C7-C25芳基烷基、C6-C18芳基;经C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C25烷基;被-O-或-S-间隔的C1-C25烷基;或-COOR119;
R119为C1-C25烷基、经E'取代和/或被D'间隔的C1-C25烷基、C7-C25芳基烷基、C6-C24芳基、经G取代的C6-C24芳基或C7-C25芳烷基,
R108和R109彼此独立地为H、C1-C25烷基、经E'取代和/或被D'间隔的C1-C25烷基、C7-C25芳基烷基、C6-C24芳基、经G取代的C6-C24芳基、C2-C20杂芳基、经G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、经E'取代和/或被D'间隔的C1-C18烷氧基或C7-C25芳烷基,或R108与R109一起形成式=CR110R111的基团,其中
R110和R111彼此独立地为H、C1-C18烷基、经E'取代和/或被D'间隔的C1-C18烷基、C6-C24芳基、经G取代的C6-C24芳基或C2-C20杂芳基或经G取代的C2-C20杂芳基,或
R108与R109一起形成5或6员环,其可任选地经以下基团取代:C1-C18烷基、经E'取代和/或被D'间隔的C1-C18烷基、C6-C24芳基、经G取代的C6-C24芳基、C2-C20杂芳基、经G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、经E'取代和/或被D'间隔的C1-C18烷氧基或C7-C25芳烷基,
D'为-CO-、-COO-、-S-、-O-或-NR112-,
E'为C1-C8硫代烷氧基、C1-C8烷氧基、CN、-NR112R113、-CONR112R113或卤素,
G为E'或C1-C18烷基,且
R112和R113彼此独立地为H;C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或被-O-间隔的C1-C18烷基,
B、D和E彼此独立地为下式的基团:
或式IV,条件为若B、D和E为式IV的基团,则其不同于A,其中
k为1,
l为0或1,
r为0或1,
z为0或1,
a为整数1-5,尤其是1-3,
g为整数1或2,
h为整数1或2,
i为0或整数1或2,
j为0或整数1或2,
k为0或整数1或2,
l为0或整数1或2,
R1′和R2'彼此独立地具有R1的含义,
Ar8、Ar8′、Ar9、Ar9′、Ar10和Ar10'彼此独立地具有Ar2的含义,Ar4、Ar5、Ar6和Ar7彼此独立地为下式的基团:
Ar20为亚芳基或亚杂芳基,其各自可任选地经取代,
R118具有R116的含义,
R13为C1-C10烷基或三(C1-C8烷基)甲硅烷基,
R14、R14'、R15、R15'、R17和R17'彼此独立地为氢;或可任选地被一个或多个氧原子间隔的C1-C25烷基,尤其是C6-C25烷基;
R18和R18'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;C7-C25芳烷基或C1-C25烷氧基;
R19为氢、C7-C25芳烷基、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;
R20和R20′彼此独立地为氢、C7-C25芳烷基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基,
X8为-O-或-NR115-;
R100和R100′彼此独立地为H、F、C1-C18烷基、被O间隔的C1-C18烷基、C1-C18烷氧基、被O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R303、R304、R305和R306彼此独立地为H、F、C1-C18烷基、被O间隔的C1-C18烷基、C1-C18烷氧基、被O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R307和R308彼此独立地为H或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;
R309、R310、R311和R312彼此独立地为H、C1-C25烷氧基或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;
R101和R101′彼此独立地为H、F、C1-C18烷基、被O间隔的C1-C18烷基、C1-C18烷氧基、被O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R102和R102'彼此独立地为H、卤素、可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳基烷基或C1-C25烷氧基;
R103和R103'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基;C7-C25芳基烷基、CN或C1-C25烷氧基;或
R103和R103′一起形成环,
R115和R115'彼此独立地为氢、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;或C7-C25芳基烷基,
R117和R117'彼此独立地为C1-C35烷基、C7-C25芳基烷基或任选地可经C1-C8烷基和/或C1-C8烷氧基取代1-3次的苯基,
R120和R120′彼此独立地为氢、可任选地被一个或多个氧或硫原子间隔的C1-C35烷基或C7-C25芳基烷基,
R121为H、可任选地被一个或多个氧或硫原子间隔的C1-C18烷基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基;可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;或CN,
在式(Vy)和(Vz)基团的情形下,X7优选为-O-、-S-、-NR115-、-C(R120)(R120')-、-Si(R117)(R117')-、-C(=O)-、 更优选-C(R120)(R120')-、最优选式的基团。
本发明聚合物可有利地用于有机光伏(PV)器件(太阳能电池)中。
有利地,本发明聚合物或包含本发明聚合物的有机半导体材料、层或组件可用于有机光伏器件(太阳能电池)和光电二极管或有机场效应晶体管(OFET)中。
本发明聚合物为共聚物。共聚物为衍生自一种以上单体的聚合物,例如二聚物、三聚物、四聚物等。
术语聚合物包含低聚物以及聚合物。本发明低聚物的重均分子量<4,000道尔顿。本发明聚合物的重均分子量优选为4,000道尔顿或更高,尤其是4,000-2,000,000道尔顿,更优选10,000-1,000,000,最优选10,000-100,000道尔顿。根据高温凝胶渗透色谱法(HT-GPC)使用聚苯乙烯标样来测定分子量。本发明聚合物的多分散性优选为1.01-10,更优选1.1-3.0,最优选1.5-2.5。聚合物比低聚物更优选。
R1和R2可为氢,但优选地与氢不同。
R1和R2可不同,但优选相同。优选地,R1和R2彼此独立地代表C1-C100烷基、可经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C5-C12环烷基、可经C1-C8烷基和/或C1-C8烷氧基取代1-3次的苯基或1-或2-萘基或-CR301R302-(CH2)u-A3,其中R301和R302代表氢或C1-C4烷基,A3代表可经C1-C8烷基和/或C1-C8烷氧基取代1-3次的苯基或1-或2-萘基,且u代表0、1、2或3。R1和R2更优选为C1-C36烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基,尤其是正十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、2-乙基己基、2-丁基己基、2-丁基辛基、2-己基癸基、2-癸基十四烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基或二十四烷基。在本发明尤其优选的实施方案中,R1和R2为2-己基癸基或2-癸基十四烷基。
R1′和R2'分别具有与R1和R2相同的优先性。
其他基团同样适用,其可以不同方式排列于单体和/或聚合物中。
若a'和c为1,e为0且Ar1和Ar2具有相同含义;或若a'、c和e为1且Ar1和Ar2以及Ar3具有相同含义;则D优选不同于Ar1。
A优选为式(IVa)、(IVb)、(IVc)、(IVd)、(IVe)、(IVf)、(IVg)、(IVh)、(IVi)、(IVj)或(IVk)的基团,如本申请的权利要求3所定义。更优选式IVa、IVc、IVe、IVg、IVh、IVi和IVk的基团。最优选式IVa、IVc、IVe、IVg、IVh和Ivi的基团。
优选地,B、D和E彼此独立地为如权利要求4中所定义的式(Va)、(Vb)、(Vc)、(Vd)、(Ve)、(Vf)、(Vg)、(Vh)、(Vi)、(Vj)、(Vk)、(Vl)、(Vm)、(Vn)、(Vo)、(Vp)、(Vq)、(Vr)、(Vs)、(Vt)、(Vu)、(Vv)、(Vw)、(Vx)、(Vy)、(Vz)或(Va')的基团。更优选式Va、Vb、Vc、Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx、Vy、Vz和Va'的基团。最优选式Va、Vc、Vf、Vh、Vi、Vk、Vo、Vp、Vq、Vr、Vs、Vu、Vw、Vx和Va'的基团。在式Vx的基团中,最优选式Vx′′的基团。
A为式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
D为式Va、Vb、Vc,尤其是Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx,尤其是Vy、Vz或Va'的基团。在所述实施方案中,更优选式的聚合物,其中n为4(尤其是10)-1000,尤其是4-200,非常特别是5(尤其是20)-100。当前最优选为如下聚合物,其中A为式IVa的基团且D为式Vx,尤其是Vx″的基团,例如该聚合物的实例为式的聚合物,其中n为4(尤其是10)-1000,尤其是4-200,非常特别是5(尤其是20)-100且R1为C1-C35烷基,尤其是C8-C35烷基。所述聚合物在用于太阳能电池中时显示高能量转换效率。
在另一实施方案中,本发明涉及式I,尤其是式Ia的聚合物,其中A为式IVa的基团且D为式Vo,尤其是的基团,例如该聚合物的实例为式的聚合物,其中n为4(尤其是10)-1000,尤其是4-200,非常特别是5(尤其是20)-100且R1为C1-C35烷基,尤其是C8-C35烷基。所述聚合物在用于太阳能电池中时显示高能量转换效率。
在优选实施方案中,本发明涉及包含下式的重复单元的聚合物:
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1;
A为式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
B和D彼此独立地为式Va、Vb、Vc,尤其是Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx,尤其是Vy、Vz或Va'的基团。式IIa聚合物的重均分子量尤其是为10,000-1,000,000道尔顿,非常特别是10,000-100,000道尔顿。
在另一优选实施方案中,本发明涉及包含下式的重复单元的聚合物:
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1;A为如权利要求3中所定义的式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
r=0.985-0.005,s=0.005-0.985,t=0.005-0.985,u=0.005-0.985,且其中r+s+t+u=1,
A为式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
B、D和E彼此独立地为式Va、Vb、Vc,尤其是Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx,尤其是Vy、Vz或Va'的基团。式IIIa聚合物的重均分子量尤其是为10,000-1,000,000道尔顿,非常特别是10,000-100,000道尔顿。
在上述实施方案中,最优选式IVa、IVc、IVe、IVg、IVh和IVi的基团作为基团A。
由式表示的聚合物结构为经由例如Suzuki聚合程序获得的聚合物产物的理想化代表。单体A、B、D和E同时聚合产生由随机排序的单元 构成的统计共聚物(聚(AD-stat-BD-stat-AE-stat-BE)。
当前最优选式(Ia)、(Ib)、(Ic)、(Id)、(If)、(Ig)、(Ih)、(Ii)、(Ij)、(Ik)、(Il)、(Im)、(In)、(Io)、(Ip)、(Iq)、(Ir)、(Is)、(It)、(Iu)、(Iv)、(Ix)、(Iy)、(Iz)、(Ia')、(Ib')、(Ic')、(Id')、(Ie')、(If′)、(Ig')、(Ih')、(Ii')、(Ij')、(IIa)、(IIb)、(IIc)、(IId)、(IIe)、(IIf)、(IIg)、(IIh)、(IIi)和(IIj)的聚合物。参照权利要求8。
R104优选为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔。
R15、R15'、R17和R17'优选彼此独立地为H;或可任选地被一个或多个氧原子间隔的C1-C25烷基,尤其是C6-C25烷基。
R20和R20′优选彼此独立地为氢、C7-C25芳烷基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基。
R100和R100'优选为H。
R101和R101'优选为H、C1-C25烷基或C1-C25烷氧基。
R102和R102'优选为H或C1-C25烷基。
R103优选为H或C1-C25烷基。
R116优选为H或C1-C25烷基。
R120和R120'优选为C1-C35烷基。
对式II聚合物更详细阐释本发明聚合物的制备。式I和III聚合物可使用对式II聚合物的制备所述的方法制备。
式II的共聚物例如可以通过Suzuki反应而得到。芳族硼酸盐和卤化物,尤其是溴化物的缩合反应通常称为“Suzuki反应”,其如N.Miyaura和A.Suzuki在Chemical Reviews,第95卷,第457-2483页(1995)所报道的那样耐受各种有机官能团的存在。优选的催化剂是2-二环己基膦基-2',6'-二烷氧基联苯/乙酸钯(II)、三烷基盐/钯(0)衍生物和三烷基膦/钯(0)衍生物。尤其优选的催化剂是2-二环己基膦基-2',6'-二甲氧基联苯(sPhos)/乙酸钯(II)、三叔丁基四氟硼酸盐((t-Bu)3P*HBF4)/三(二亚苄基丙酮)二钯(0)(Pd2(dba)3)和三叔丁基膦(t-Bu)3P/三(二亚苄基丙酮)二钯(0)(Pd2(dba)3)。该反应可以用于制备高分子量聚合物和共聚物。
为制备对应于式II的聚合物,在Pd和三苯基膦的催化作用下使式X10-A-X10和X10-B-X10的二卤化物与(等摩尔)量对应于式的二硼酸或二硼酸盐反应;或使式的二卤化物与(等摩尔)量对应于式X11-A-X11和X11-B-X11的二硼酸或二硼酸盐反应,其中X10为卤素,尤其是Cl、Br或I,非常特别是Br,且X11在每次出现时独立地为
-B(OH)2、-B(OY1)2、其中Y1在每次出现时独立地为C1-C10烷基且Y2在每次出现时独立地为C2-C10亚烷基,例如-CY3Y4-CY5Y6-或-CY7Y8-CY9Y10-CY11Y12-,其中Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11和Y12彼此独立地为氢或C1-C10烷基,尤其是-C(CH3)2C(CH3)2-、-CH2C(CH3)2CH2-或-C(CH3)2CH2C(CH3)2-,且Y13和Y14彼此独立地为氢或C1-C10烷基。该反应通常在约0-180°C下在芳族烃溶剂如甲苯或二甲苯中进行。其他溶剂如二甲基甲酰胺、二烷、二甲氧基乙烷和四氢呋喃也可以单独使用或以与芳族烃的混合物使用。将含水碱,优选碳酸钠或碳酸氢钠、磷酸钾、碳酸钾或碳酸氢钾用作硼酸、硼酸盐的活化剂以及用作HBr清除剂。聚合反应可以进行0.2-100小时。有机碱如氢氧化四烷基铵和相转移催化剂如TBAB可以促进硼的活性(例如参见Leadbeater&Marco;Angew.Chem.Int.Ed.Eng.42(2003)1407及其中所引用的文献)。反应条件的其他变化由T.I.Wallow和B.M.Novak给于J.Org.Chem.59(1994)5034-5037中;并由M.Remmers,M.Schulze和G.Wegner给于Macromol.Rapid Commun.17(1996)239-252中。分子量的控制可以通过使用过量二溴化物、二硼酸或二硼酸酯或链终止剂而进行。
根据WO2010/136352(欧洲专利申请no.09176497.7)中所述的方法,该聚合在在如下组分存在下进行:
b)碱,
c)溶剂或溶剂混合物,其特征在于
所述有机膦为下式的经三取代膦:
或其盐,其中X独立于Y地代表氮原子或C-R2″基团且Y独立于X地代表氮原子或C-R9″基团,两个R1″基团中每一个的R1″独立于另一个代表选自以下基团的基团:C1-C24烷基、C3-C20环烷基(其尤其包括单环以及双环和三环环烷基)、C5-Cl4芳基(其尤其包括苯基、萘基、芴基)、C2-C13杂芳基(其中选自N、O、S的杂原子的数目可为1-2),其中两个R1″基团还可彼此连接,
且其中上述基团R1″本身可各自彼此独立地经选自以下基团的取代基单取代或多取代:氢、C1-C20烷基、C2-C20链烯基、C3-C8环烷基、C2-C9杂烷基、C5-C10芳基、C2-C9杂芳基(其中来自N、O、S的杂原子的数目可为1-4)、C1-C20烷氧基、C1-C10卤代烷基、羟基、NH-(C1-C20烷基)、NH-(C5-C10芳基)、N(C1-C20烷基)2、N(C1-C20烷基)(C5-C10芳基)、N(C5-C10芳基)2、N(C1-C20烷基/C5-C10芳基3)3 +、NH-CO-C1-C20烷基、NH-CO-C5-C10芳基形式的氨基、COOH和COOQ形式的羧酸根基(其中Q代表单价阳离子或C1-C8烷基)、C1-C6酰氧基、亚磺酸根基、SO3H和SO3Q'形式的磺酸根基(其中Q'代表单价阳离子、C1-C20烷基或C5-C10芳基)、三-C1-C6烷基甲硅烷基,其中两个所述取代基还可彼此桥接,R2″-R9″代表氢、烷基、链烯基、环烷基、芳族或杂芳族芳基、O-烷基、NH-烷基、N-(烷基)2、O-(芳基)、NH-(芳基)、N-(烷基)(芳基)、O-CO-烷基、O-CO-芳基、F、Si(烷基)3、CF3、CN、CO2H、COH、SO3H、CONH2、CONH(烷基)、CON(烷基)2、SO2(烷基)、SO(烷基)、SO(芳基)、SO2(芳基)、SO3(烷基)、SO3(芳基)、S-烷基、S-芳基、NH-CO(烷基)、CO2(烷基)、CONH2、CO(烷基)、NHCOH、NHCO2(烷基)、CO(芳基)、CO2(芳基)基团,其中两个或更多个彼此独立的相邻基团还可彼此连接从而产生稠合的环系统,且其中在R2″-R9″中,烷基代表可在每一情形下为直链或支化且具有1-20个碳原子的烃基团,链烯基代表可在每一情形下为直链或支化且具有2-20个碳原子的单-或多不饱和烃基团,环烷基代表具有3-20个碳原子的烃,芳基代表5-14员芳族基团,其中芳基中的1-4个碳原子还可由来自基团氮、氧和硫的杂原子代替从而产生5-14员杂芳族基团,其中基团R2″-R9″还可具有对R1″所定义的其他取代基。
有机膦及其合成阐述于WO2004101581中。
优选的有机膦选自下式的经三取代膦:
优选催化剂的实例包含下列化合物:
乙酰丙酮钯(II)、二亚苄基丙酮钯(0)配合物、丙酸钯(II),
Pd2(dba)3:[三(二亚苄基丙酮)二钯(0)],
Pd(dba)2:[二(二亚苄基丙酮)钯(0)],
Pd(PR3)2,其中PR3为式VI的经三取代膦,
Pd(OAc)2:[乙酸钯(II)]、氯化钯(II)、溴化钯(II)、四氯钯酸锂(II),
PdCl2(PR3)2:其中PR3为式VI的经三取代膦;钯(0)二烯丙基醚配合物、硝酸钯(II),
PdCl2(PhCN)2:[二氯二(苄腈)钯(II)],
PdCl2(CH3CN):[二氯二(乙腈)钯(II)],和
PdCl2(COD):[二氯(1,5-环辛二烯)钯(II)]。
尤其优选为PdCl2、Pd2(dba)3、Pd(dba)2、Pd(OAc)2或Pd(PR3)2。最优选为Pd2(dba)3和Pd(OAc)2。
钯催化剂以催化量存在于反应混合物中。术语“催化量”为指显著低于1当量(杂)芳族化合物的量,基于所用(杂)芳族化合物的当量,优选为0.001-5mol%,最优选为0.001-1mol%。
碱可选自所有水性和非水性碱且可为无机或有机碱。优选地,反应混合物中存在至少1.5当量的所述碱/硼官能团。合适的碱为例如碱金属和碱土金属的氢氧化物、羧酸盐、碳酸盐、氟化物和磷酸盐(例如钠和钾的氢氧化物、乙酸盐、碳酸盐、氟化物和磷酸盐)或还金属醇盐。还可使用碱的混合物。碱优选为锂盐,例如,锂醇盐(例如甲醇锂和乙醇锂)、氢氧化锂、羧酸锂、碳酸锂、氟化锂和/或磷酸锂。
当前最优选的碱为水性LiOHxH2O(LiOH的单水合物)和(无水)LiOH。
反应通常为在约0-180℃,优选20-160℃,更优选40-140℃,最优选40-120℃下实施。聚合反应可进行0.1小时,尤其是0.2-100小时。
在本发明的优选实施方案中,溶剂为THF,碱为LiOH*H2O且反应为在THF的回流温度(约65℃)下进行。
溶剂为选自例如甲苯、二甲苯、苯甲醚、THF、2-甲基四氢呋喃、二恶烷、氯苯、氟苯或包含一种或多种溶剂的溶剂(例如THF/甲苯)和任选地水的混合物。最优选为THF或THF/水。
有利地,在以下物质存在下进行聚合:
a)乙酸钯(II)或Pd2(dba)3(三(二亚苄基丙酮)二钯(0))和有机膦A-1至A-13,
b)LiOH或LiOHxH2O;和
c)THF、和任选地水。若使用LiOH的单水合物,则无需添加水。
最优选地,在以下物质存在下进行聚合:
a)乙酸钯(II)或Pd2(dba)3(三(二亚苄基丙酮)二钯(0))和
b)LiOHxH2O;和
c)THF。基于所用(杂)芳族化合物的当量,钯催化剂的存在量优选为约0.5mol%。基于所用(杂)芳族化合物的当量,反应混合物中膦或盐的量优选为约2mol%。Pd:膦的优选比率为约1:4。
优选地,在不存在氧的惰性条件下进行聚合反应。使用氮气和(更优选)氩气作为惰性气体。
欧洲专利申请号09176497.7中所述的方法适用于大规模应用,易于获得且可以高产率、高纯度和高选择性将原料转化成相应聚合物。该方法可提供重均分子量为至少10,000道尔顿,更优选至少20,000道尔顿,最优选至少30,000道尔顿的聚合物。目前最优选的聚合物的重均分子量为30,000-80,000道尔顿。根据高温凝胶渗透色谱法(HT-GPC)使用聚苯乙烯标样来测定分子量。聚合物的多分散性优选为1.01-10,更优选1.1-3.0,最优选1.5-2.5。
若需要,可使用单官能芳基卤或硼酸芳基酯作为该反应中的链终止剂,其导致形成末端芳基。
在Suzuki反应中,可通过控制单体进料的顺序和组成来控制所得共聚物中单体单元的定序。
本发明聚合物还可通过Stille偶联来合成(例如,参见Babudri等,J.Mater.Chem.,2004,14,11-34;J.K.Stille,Angew.Chemie Int.Ed.Engl.1986,25,508)。为制备对应于式II的聚合物,在0-200℃的温度下和含钯催化剂存在下在惰性溶剂中使式X10-A-X10和X10-B-X10的二卤化物与式X21-D-X21的化合物反应,或使式X10-D-X10的二卤化物与式X21-A-X21和X21B-X21的化合物反应,其中X21为基团-SnR207R208R209且X10如上文所定义,其中R207、R208和R209相同或不同且为H或C1-C6烷基,其中两个基团任选地形成共同环且该基团任选地支化或未支化。此处必须确保所用所有单体的总体中有机锡官能团与卤素官能团的比率高度平衡。此外,可以证实,在反应结束时通过使用单官能试剂进行封端来去除任何过量的反应性基团为有利的。为进行该方法,优选地将锡化合物和卤素化合物引入一种或多种惰性有机溶剂中,且在0-200℃,优选30-170℃的温度下搅拌1-200小时,优选5-150小时。可通过本领域熟练技术人员所已知且适用于各种聚合物的方法来纯化粗产物,例如重复进行的再沉淀或甚至通过透析来纯化。
适用于所述方法的有机溶剂为例如醚,例如二乙醚、二甲氧基乙烷、二甘醇二甲基醚、四氢呋喃、二烷、二氧戊环、二异丙基醚和叔丁基甲基醚,烃,例如己烷、异己烷、庚烷、环己烷、苯、甲苯和二甲苯,醇,例如甲醇、乙醇、1-丙醇、2-丙醇、乙二醇、1-丁醇、2-丁醇和叔丁醇,酮,例如丙酮、乙基甲基酮和异丁基甲基酮,酰胺,例如二甲基甲酰胺(DMF)、二甲基乙酰胺和N-甲基吡咯啶酮,腈,例如乙腈、丙腈和丁腈,及其混合物。
应以类似于对Suzuki变化形式所述的方式来选择钯和膦组分。
或者,本发明聚合物还可通过Negishi反应使用锌试剂A-(ZnX22)2和B-(ZnX22)2(其中X22为卤素和卤化物)、和D-(X23)2(其中X23为卤素或三氟甲磺酸盐)或使用A-(X22)2、B-(X22)2和D-(ZnX23)2来合成。例如,参见E.Negishi等,Heterocycles 18(1982)117-22。
或者,本发明聚合物还可通过Hiyama反应使用有机硅试剂A-(SiR210R211R212)2和B-(SiR210R211R212)2(其中R210、R211和R212相同或不同且为卤素或C1-C6烷基)和D-(X23)2(其中X23为卤素或三氟甲磺酸盐)或使用A-(X23)2、B-(X23)2和D-(SiR210R211R212)2来合成。例如,参见T.Hiyama等,Pure Appl.Chem.66(1994)1471-1478和T.Hiyama等,Synlett(1991)845-853。
式的化合物为本发明聚合物生产中的中间体,其中a、b、c、d、e、f、R1、R2、Ar1、Ar1′、Ar2、Ar2′、Ar3和Ar3'如上文所定义且X11'在每次出现时独立地为卤原子,非常特别为I或Br;或具有X11的含义。
式的化合物为新化合物且为本申请的另一目的,其中
a、b、c、d、e、f、R1、R2、Ar1、Ar1′、Ar2、Ar2′、Ar3和Ar3'如权利要求1中所定义且X11在每次出现时独立地为ZnX12、-SnR207R208R209,其中R207、R208和R209相同或不同且为H或C1-C6烷基,其中两个基团任选地形成共同环且该基团任选地支化或未支化;X12为卤原子,非常特别为I或Br;-OS(O)2CF3、-OS(O)2-芳基,尤其是-OS(O)2CH3、-B(OH)2、-B(OH)3 -、-BF3、
-B(OY1)2、其中Y1在每次出现时独立地为C1-C10烷基且Y2在每次出现时独立地为C2-C10亚烷基,例如-CY3Y4-CY5Y6-或-CY7Y8-CY9Y10-CY11Y12-,其中Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11和Y12彼此独立地为氢或C1-C10烷基,尤其是-C(CH3)2C(CH3)2-或-C(CH3)2CH2C(CH3)2-、-CH2C(CH3)2CH2-,且Y13和Y14彼此独立地为氢或C1-C10烷基。
下文展示式X化合物的实例:
X11'、R1、R2、R116、R104和R104'如上文所定义。
R1和R2优选为C1-C36烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基,尤其是正十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、2-乙基己基、2-丁基己基、2-丁基辛基、2-己基癸基、2-辛基十二烷基、2-癸基十四烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基或二十四烷基。
R104和R104'可相同或不同且优选为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
R116优选为H或C1-C25烷基。
可通过使用可在聚合后去除的保护基团来获得其中R1和/或R2为氢的聚合物(例如,参见,EP-A-0648770、EP-A-0648817、EP-A-0742255、EP-A-0761772、WO 98/32802、WO 98/45757、WO 98/58027、WO99/01511、WO 00/17275、WO 00/39221、WO 00/63297和EP-A-1086984)。借助以下方式将颜料前体转化成其颜料形式:在已知条件(例如热条件)下、任选地在额外催化剂(例如WO 00/36210中所述的催化剂)存在下裂解。
L优选为式、 的基团,其中Z1、Z2和Z3彼此独立地为C1-C6烷基,
Z4和Z8彼此独立地为C1-C6烷基,被氧、硫或N(Z12)2间隔的C1-C6烷基,或未经取代或经C1-C6烷基、C1-C6烷氧基、卤基、氰基或硝基取代的苯基或联苯,
Z5、Z6和Z7彼此独立地为氢或C1-C6烷基,
Z10和Z11彼此独立地为氢、C1-C6烷基、C1-C6烷氧基、卤素、氰基、硝基、N(Z12)2或未经取代或经卤基、氰基、硝基、C1-C6烷基或C1-C6烷氧基取代的苯基,
Z12和Z13为C1-C6烷基,Z14为氢或C1-C6烷基,且Z15为氢、C1-C6烷基或未经取代或经C1-C6烷基取代的苯基,
Q为未经取代或经C1-C6烷氧基、C1-C6烷硫基或C2-C12二烷基氨基单取代或多取代的p,q-C2-C6亚烷基,其中p和q为不同的位置编号,
X为选自氮、氧及硫的杂原子,m'在X为氧或硫时为数字0且m在X为氮时为数字1,且
L1和L2彼此独立地为未经取代或经C1-C12烷氧基-、-C1-C12烷硫基-、-C2-C24二烷基氨基-、-C6-C12芳基氧基-、-C6-C12芳硫基-、-C7-C24烷基芳基氨基-或-C12-C24二芳基氨基单-或多取代的C1-C6烷基或[-(p',q'-C2-C6亚烷基)-Z-]n'-C1-C6烷基,n'为1-1000的数字,p'和q'为不同的位置编号,Z各自独立地为杂原子氧、硫或C1-C12烷基取代氮,且[-C2-C6亚烷基-Z-]重复单元中的C2-C6亚烷基可相同或不同,
且L1和L2可为饱和的或具有1-10的不饱和度,可未被间隔或在任一位置被1-10个选自-(C=O)-和-C6H4-的基团间隔,且可不具有其他取代基或具有1-10个选自卤素、氰基和硝基的其他取代基。最优选地,L为式的基团。
式Br-A-Br化合物的合成阐述于WO 08/000664和WO 09/047104中,或可以类似于本文所述的方法来合成。式Br-A-Br的N-芳基取代化合物可以类似于US-A-5,354,869和WO 03/022848中所述的方法来合成。
卤素为氟、氯、溴和碘。
若可能,C1-C25烷基(C1-C18烷基)通常为直链或支化烷基。实例为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基或二十五烷基。C1-C8烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、正己基、正庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基。C1-C4烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基。
C2-C18链烯基为直链或支化烯基,例如乙烯基、烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基丁-2-烯基、正辛-2-烯基、正十二-2-烯基、异十二烯基、正十二-2-烯基或正十八-4-烯基。
C2-18炔基为直链或支化且优选为可未经取代或经取代的C2-8炔基,例如,乙炔基、1-丙炔-3-基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1,4-戊二炔-3-基、1,3-戊二炔-5-基、1-己炔-6-基、顺式-3-甲基-2-戊烯-4-炔-1-基、反式-3-甲基-2-戊烯-4-炔-1-基、1,3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基或1-二十四炔-24-基。
C1-C25烷氧基(C1-C18烷氧基)为直链或支化烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基和十八烷氧基。C1-C8烷氧基的实例为甲氧基、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、2-戊氧基、3-戊氧基、2,2-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1,3,3-四甲基丁氧基和2-乙基己氧基,优选为C1-C4烷氧基,例如通常为甲氧基、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。术语“烷硫基”意指与烷氧基相同的基团,不同的是醚键的氧原子由硫原子代替。
C1-C18全氟烷基,尤其是C1-C4全氟烷基为支化或未支化基团,例如-CF3、-CF2CF3、-CF2CF2CF3、-CF(CF3)2、-(CF2)3CF3和-C(CF3)3。
术语“氨基甲酰基”通常为可未经取代或经取代的C1-18氨基甲酰基,优选C1-8氨基甲酰基,例如,氨基甲酰基、甲基氨基甲酰基、乙基氨基甲酰基、正丁基氨基甲酰基、叔丁基氨基甲酰基、二甲基氨基甲酰基氧基、吗啉基氨基甲酰基或吡咯烷基氨基甲酰基。
C5-C12环烷基通常为环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十一烷基、环十二烷基,优选为可未经取代或经取代的环戊基、环己基、环庚基或环辛基。环烷基,尤其是环己基可由可经C1-C4烷基、卤素和氰基取代1-3次的苯基稠合一次或两次。该稠合环己基的实例为:
C6-C24芳基(C6-C18芳基)通常为可未经取代或经取代的苯基、茚基、甘菊环基、萘基、联苯、as-indacenyl、s-indacenyl、苊基、芴基、菲基、荧葸基、苯并菲基、基、并四苯基、苉基、苝基、戊芬基(pentaphenyl)、并六苯基、芘基或蒽基,优选为苯基、1-萘基、2-萘基、4-联苯基、9-菲基、2-或9-芴基、3-或4-联苯基。C6-C12芳基的实例为可未经取代或经取代的苯基、1-萘基、2-萘基、3-或4-联苯基、2-或9-芴基或9-菲基。
C7-C25芳烷基通常为苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基、ω-苯基十八烷基、ω-苯基二十烷基或ω-苯基二十二烷基,优选为C7-C18芳烷基,例如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基或ω-苯基十八烷基,尤其优选为C7-C12芳烷基,例如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基或ω,ω-二甲基-ω-苯基丁基,其中脂肪烃基团和芳族烃基团均可未经取代或经取代。优选实例为苄基、2-苯乙基、3-苯丙基、萘基乙基、萘基甲基和枯基。
杂芳基通常为C2-C20杂芳基,即氮、氧或硫为可能杂原子的具有5-7个环原子的环或稠合环系统,且通常为具有5-30个原子且具有至少6个共轭π-电子的不饱和杂环基团,例如噻吩基、苯并[b]噻吩基、二苯并[b,d]噻吩基、噻蒽基、呋喃基、糠基、2H-吡喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、苯氧基噻吩基、吡咯基、咪唑基、吡唑基、吡啶基、联吡啶基、三嗪基、嘧啶基、吡嗪基、哒嗪基、中氮茚基、异氮杂茚基、吲哚基、吲唑基、嘌呤基、喹嗪基、喹啉基、异喹啉基、2,3-二氮杂萘基、1,5-二氮杂萘基、喹喔啉基、喹唑啉基、肉啉基、喋啶基、咔唑基、咔啉基、苯并三唑基、苯并唑基、菲啶基、吖啶基、嘧啶基、菲咯啉基、吩嗪基、异噻唑基、吩噻嗪基、异唑基、呋咱基或吩嗪基,其可未经取代或经取代。
上述基团的可能取代基为C1-C8烷基、羟基、巯基、C1-C8烷氧基、C1-C8烷硫基、卤素、卤代-C1-C8烷基、氰基、氨基甲酰基、硝基或甲硅烷基,尤其是C1-C8烷基、C1-C8烷氧基、C1-C8烷硫基、卤素、卤代-C1-C8烷基或氰基。
被一个或多个O间隔的C1-C18烷基为(例如)(CH2CH2O)1-9-Rx,其中Rx为H或C1-C10烷基;CH2-CH(ORy')-CH2-O-Ry,其中Ry为C1-C18烷基,且Ry'包含与Ry相同的定义或为H。
若取代基(例如R18)在基团中出现一次以上,则在每次出现时其可不同。
措辞“由G取代”意指可能存在一个或多个,尤其是1-3个取代基G。
如上文所述,上述基团可由E'取代和/或若需要可被D'间隔。当然,仅在含有至少2个由单键彼此连接的碳原子的基团情形下可能间隔;C6-C18芳基未被间隔;经间隔芳基烷基在烷基部分中含有单元D。由一个或多个E'取代和/或被一个或多个单元D间隔的C1-C18烷基为例如(CH2CH2O)1-9-Rx,其中Rx为H或C1-C10烷基或C2-C10烷酰基(例如,CO-CH(C2H5)C4H9)、CH2-CH(ORy')-CH2-O-Ry,其中Ry为C1-C18烷基、C5-C12环烷基、苯基、C7-C15苯基烷基,且Ry'涵盖与Ry相同的定义或为H;C1-C8亚烷基-COO-Rz,例如,CH2COORz、CH(CH3)COORz、C(CH3)2COORz,其中Rz为H、C1-C18烷基、(CH2CH2O)1-9-Rx,且Rx涵盖上述定义;CH2CH2-O-CO-CH=CH2;CH2CH(OH)CH2-O-CO-C(CH3)=CH2。
含有本发明聚合物的混合物产生包含本发明聚合物(通常5-99.9999重量%,尤其是20-85重量%)和至少另一材料的半导体层。该另一材料可为但不限于本发明相同聚合物的具有不同分子量的部分、另一本发明聚合物、半导体聚合物、有机小分子、碳纳米管、富勒烯衍生物、无机颗粒(量子点、量子棒、三脚型量子(quantum tripod)、TiO2、ZnO等)、导电颗粒(Au、Ag等)、绝缘体材料(例如对栅极介电质所述那些)(PET、PS等)。
本发明聚合物可与例如欧洲专利申请号09155919.5、WO 09/047104、US 6,690,029、WO 2007082584和WO 2008107089中所述的小分子共混。WO 2007082584:
WO 2008107089:
其中Y1′和Y2'中的一个表示-CH=或=CH-且另一个表示-X'-,
Y3'和Y4'中的一个表示-CH=或=CH-且另一个表示-X'-,
X'为-O-、-S-、-Se-或-NR″′-,
R″″为具有1-20个C原子的环状、直链或支化烷基或烷氧基,或具有2-30个C原子的芳基,其均任选地经氟化或全氟化,
R'为H、F、Cl、Br、I、CN、具有1-20个C原子且任选地经氟化或全氟化的直链或支化烷基或烷氧基、具有6-30个C原子且任选地经氟化或全氟化的芳基或CO2R″,其中R″为H、具有1-20个C原子且任选地经氟化的烷基或具有2-30个C原子且任选地经氟化的芳基,
R″′为H或具有1-10个C原子的环状、直链或支化烷基,y为0或1,x为0或1。
聚合物可含有一个小分子或两个或更多个小分子化合物的混合物。
因此,本发明还涉及包含本发明聚合物的有机半导体材料、层或组件。
本发明聚合物可作为半导体层用于半导体器件中。因此,本发明还涉及包含本发明聚合物的或有机半导体材料、层或组件的半导体器件。该半导体器件尤其是为有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管。
本发明聚合物可单独或组合用作半导体器件的有机半导体层。可通过任一有用方式来提供层,例如,蒸气沉积(用于分子量相对较低的材料)和印刷技术。本发明化合物可充分地溶于有机溶剂中且可进行溶液沉积和图案化(例如,通过旋涂、浸涂、喷墨印刷、凹版印刷、挠性印刷、胶版印刷、丝网印刷、微接触(波)印刷、滴注或分区浇注或其他已知技术来进行)。
本发明聚合物可用于包含多个OTFT的集成电路以及各种电子制品中。该制品包括例如射频识别(RFID)标签、用于柔性显示器(例如,用于个人计算机、移动电话或手持式器件)的背板、智能卡、内存器件、传感器(例如光传感器、图像传感器、生物传感器、化学传感器、机械传感器或温度传感器),尤其是光电二极管或安全器件等。
本发明另一方面为包含一种或多种本发明聚合物的有机半导体材料、层或组件。另一方面为本发明聚合物或材料在有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管(OFET)中的用途。另一方面为包含本发明聚合物或材料的有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管(OFET)。
本发明聚合物通常以薄有机层或膜形式用作有机半导体,优选小于30微米厚。通常,本发明的半导体层为至多1微米(=1μm)厚,但若需要其可更厚。对于各种电子器件应用,该厚度还可小于约1微米厚。例如,在用于OFET中时,层厚度通常可为100nm或更小。层的确切厚度取决于例如使用层的电子器件的要求。
例如,OFET中漏电极与源电极之间的活性半导体沟槽可包含本发明的层。
本发明OFET器件优选包含:
-源电极,
-漏电极,
-栅电极,
-半导体层,
-一个或多个栅极绝缘体层,和
-任选地基材,其中半导体层包含一种或多种本发明聚合物。
OFET器件中的栅电极、源电极和漏电极以及绝缘和半导体层可以任何顺序排列,条件为源电极和漏电极通过绝缘层与栅电极分开,栅电极和半导体层均接触绝缘层,且源电极和漏电极均接触半导体层。
优选地,OFET包含具有第一侧和第二侧的绝缘体、位于该绝缘体第一侧上的栅电极、位于该绝缘体第二侧上且包含本发明聚合物的层以及位于该聚合物层上的漏电极和源电极。
OFET器件可为顶部栅极器件或底部栅极器件。
OFET器件的合适结构和制造方法已为本领域熟练技术人员所熟知且阐述于参考文献例如WO 03/052841中。
栅极绝缘体层可包含例如氟聚合物,例如市售的Cytop或Cytop(来自Asahi Glass)。优选地,由包含绝缘体材料和一种或多种具有一个或多个氟原子的溶剂(氟溶剂)(优选全氟溶剂)的配制剂来沉积栅极绝缘体层,例如通过旋涂、刮涂、绕线棒涂覆、喷涂或浸涂或其他已知方法来实施。合适全氟溶剂为例如(购自Acros,目录号12380)。其他合适氟聚合物和氟溶剂在本领域中已知,例如全氟聚合物Teflon1600或2400(来自DuPont)或(来自Cytonix)或全氟溶剂FC(Acros,第12377号)。
包含本发明聚合物的半导体层可另外包含至少另一材料。该另一材料可为但不限于本发明另一聚合物、半导体聚合物、聚合粘合剂、不同于本发明聚合物的有机小分子、碳纳米管、富勒烯衍生物、无机颗粒(量子点、量子棒、三脚型量子、TiO2、ZnO等)、导电颗粒(Au、Ag等)以及绝缘材料(例如对栅极介电质所述那些)(PET、PS等)。如上所述,半导体层还可由一种或多种本发明聚合物和聚合粘合剂的混合物构成。本发明聚合物与聚合粘合剂的比率可在5-95%之间有所变化。优选地,聚合粘合剂为半结晶聚合物,例如聚苯乙烯(PS)、高密度聚乙烯(HDPE)、聚丙烯(PP)和聚甲基丙烯酸甲酯(PMMA)。使用此技术,可避免电性能变差(参见WO2008/001123A1)。
本发明聚合物有利地用于有机光伏(PV)器件(太阳能电池)中。因此,本发明提供包含本发明聚合物的PV器件。具有此构造的器件还具有整流性能,因此还可称作光电二极管。光敏器件可用作由光产生电的太阳能电池并测量或检测光的光检测器。
有机光伏器件(太阳能电池)的结构阐述于(例如)C.Deibel等,Rep.Prog.Phys.73(2010)096401和Christoph Brabec,Energy Environ.Sci 2.(2009)347-303中。
PV器件按以下顺序包含:
(a)阴极(电极),
(b)任选的过渡层,例如碱金属卤化物,尤其是氟化锂,
(c)光活性层,
(d)任选的平滑层,
(e)阳极(电极),
(f)基材。
光活性层包含本发明聚合物。优选地,光活性层为由本发明的共轭聚合物(作为电子供体)和受体材料(例如富勒烯,尤其是官能化富勒烯PCBM)(作为电子受体)构成。如上所述,光活性层还可含有聚合粘合剂。基于本发明聚合物和聚合粘合剂的量,本发明聚合物占聚合粘合剂的量可为0.1-99.9重量%,尤其是1-99重量%,非常特别是5-95重量%。优选地,聚合粘合剂为半结晶聚合物,例如聚苯乙烯(PS)、高密度聚乙烯(HDPE)、聚丙烯(PP)和聚甲基丙烯酸甲酯(PMMA)。
对于异质结太阳能电池而言,活性层优选包含重量比率为1:1-1:3的本发明聚合物与富勒烯的混合物,该富勒烯为例如[60]PCBM(=6,6-苯基-C61-丁酸甲酯)或[70]PCBM。可用于本发明中的富勒烯具有宽范围的大小(碳原子数/分子)。本文所用的术语富勒烯包括纯碳的各种笼状分子,包括巴Buckminster富勒烯(C60)和相关“球形”富勒烯以及碳纳米管。富勒烯可选自本技术中所已知的那些,例如C20-C1000。优选地,富勒烯选自C60-C96。最优选地,富勒烯为C60或C70,例如[60]PCBM或[70]PCBM。还容许使用经化学改性的富勒烯,条件为经改性富勒烯保持受体型和电子迁移率特性。受体材料还可为选自如下的材料:任一半导体聚合物(例如,本发明聚合物,条件为聚合物保持受体型和电子迁移率特性)、有机小分子、碳纳米管、无机颗粒(量子点、量子棒、三脚型量子、TiO2、ZnO等)。
光活性层为自本发明聚合物(作为电子供体)和富勒烯,尤其是官能化富勒烯PCBM(作为电子受体)构成。将该两种组分与溶剂混合并通过例如以下方法以溶液形式施加至平滑层上:旋涂法、滴注法、Langmuir-Blodgett(“LB”)法、喷墨印刷法和滴涂法。还可使用刮擦辊或印刷方法来使用该光活性层涂覆较大表面。优选使用分散剂如氯苯来代替通常所用的甲苯作为溶剂。在该方法中,从操作容易性和成本角度考虑,尤其优选真空沉积法、旋涂法、喷墨印刷法和浇注法。
在使用旋涂法、浇注法和喷墨印刷法形成层的情形下,可使用通过将组合物溶解或分散于合适有机溶剂如苯、甲苯、二甲苯、四氢呋喃、甲基四氢呋喃、N,N-二甲基甲酰胺、丙酮、乙腈、苯甲醚、二氯甲烷、二甲亚砜、氯苯、1,2-二氯苯及其混合物中制得的浓度为0.01-90重量%的溶液和/或分散体来实施涂覆。
光伏(PV)器件还可由多结点太阳能电池构成,该多结点太阳能电池在彼此的顶部经处理以在更大范围内吸收太阳光谱。该结构阐述于例如App.Phys.Let.90,143512(2007)、Adv.Funct.Mater.16,1897-1903(2006)、WO2004/112161和Christoph Brabec,Energy Environ.Sci 2.(2009)347-303中。
所谓的“串级太阳能电池”按以下顺序包含:
(a)阴极(电极),
(b)任选的过渡层,例如碱金属卤化物,尤其是氟化锂,
(c)光活性层,
(d)任选的平滑层,
(e)中部电极(例如Au、Al、ZnO、TiO2等)
(f)任选的用于匹配能级的额外电极,
(g)任选的过渡层,例如碱金属卤化物,尤其是氟化锂,
(h)光活性层,
(i)任选的平滑层,
(j)阳极(电极),
(k)基材。
还可在纤维制品上加工PV器件,例如如US 20070079867和US20060013549中所述。
由于具有优良的自组织性能,包含本发明聚合物的材料或膜还可单独或与其他材料一起用于LCD或OLED器件中或作为对准层用于LCD或OLED器件中,例如如US 2003/0021913中所述。
所包括的下列实施例仅用于阐释本发明而并不限制权利要求书的范畴。除非另有说明,否则所有份数和百分比均以重量计。
重均分子量(Mw)和多分散性(Mw/Mn=PD)通过高温凝胶渗透色谱法(HT-GPC)测得[设备:GPC PL 220,来自Polymer实验室(ChurchStretton,UK;现为Varian),其由折射率(RI)产生反应,色谱条件:柱:3“PLgel Olexis”柱,来自Polymer实验室(Church Stretton,UK);平均粒度为13μm(尺寸为300×8mm I.D.)流动相:1,2,4-三氯苯,通过真空蒸馏纯化且通过丁羟基甲苯(BHT,200mg/l)稳定,色谱温度:150℃;流动相流量:1ml/min;溶质浓度:约1mg/ml;注射体积:200μl;检测:RI,分子量校准程序:使用一组自Polymer实验室(Church Stretton,UK)获得的10份聚苯乙烯校准标样来实施相对校准,该聚苯乙烯的分子量范围跨度为1,930,000-5,050Da,即,PS 1,930,000、PS 1,460,000、PS 1,075,000、PS 560,000、PS 330,000、PS 96,000、PS 52,000、PS 30,300、PS 10,100、PS 5,050Da。使用多项式校准来计算分子量。
下文实施例给出的所有聚合物结构均为经由所述聚合程序获得的聚合物产物的理想化代表。若两种以上组分彼此共聚,则聚合物中的顺序取决于聚合条件可为交替或无规的。
实施例
实施例1
a)将20g[88949-34-2]和25.76g碳酸钾悬浮于300ml无水二甲基甲酰胺中并在氮气下将混合物加热至90℃。随后逐滴添加79g[1044598-79-9]。随后将反应混合物在90℃下搅拌6h。在冷却至室温后,添加乙酸乙酯并用水洗涤混合物。经硫酸镁干燥有机相并蒸发溶剂。通过在二氧化硅上柱层析纯化产物,从而获得式1化合物。1H-NMR数据(ppm,CDCl3):8.332H d,7.602H d,6.682H dxd,4.034H d,1.85-1.752H m,1.45-1.1548H m,0.886H t,0.866H t;
b)将6.44g化合物1溶解于100ml氯仿中。将混合物冷却至-10℃且随后添加1.99g N-溴琥珀酰亚胺(NBS)并将混合物于-10℃下搅拌2小时。将反应混合物用水洗涤,用硫酸镁干燥并蒸发溶剂。通过在二氧化硅上柱层析纯化粗产物,从而获得式2化合物。1H-NMR数据(ppm,苯-D6):8.722H d,6.052H d,4.134H d,2.06-2.022H m,1.65-1.3048H m,1.016H t,1.006H t;
c)在氩气气氛下向三颈反应烧瓶中添加0.5g化合物2、0.188g 1,4-苯二硼酸二频哪醇酯[99770-93-1]和51mg乙酸钯。向反应烧瓶中添加15ml脱气THF并加热混合物以溶解原料。在用氩气进一步脱气后,添加27mg 2-(二叔丁基膦基)-1-苯基-1H-吡咯并加热回流反应混合物。随后添加146mg氢氧化锂水合物并将反应混合物在回流下搅拌2小时。随后将反应混合物冷却至室温并将产物用甲醇沉淀,过滤并用甲醇洗涤。通过Soxhlet萃取获得式3的聚合物。氯仿级分含有Mw为90,100且多分散性为2.69(通过高温GPC测量)的聚合物。
实施例2
以类似于实施例1c)的方式由化合物2和噻吩二硼酸频哪醇酯[175361-81-6]开始合成式4的聚合物。Soxhlet萃取的四氢呋喃级分含有Mw为74,600且多分散性为2.26(通过高温GPC测量)的式4的聚合物。
实施例3
以类似于实施例1c)的方式由化合物2和噻吩并噻吩二硼酸频哪醇酯[924894-85-9]开始合成式5的聚合物。式5的粗制聚合物的Mw为8,300且多分散性为2.06(通过高温GPC测量)。
实施例4
以类似于实施例1c)的方式由化合物2和二噻吩二硼酸频哪醇酯[239075-02-6]开始合成式6的聚合物。式6的粗制聚合物的Mw为6,300且多分散性为1.44(通过高温GPC测量)。
实施例5
a)根据化合物[1220883-00-0]使式2的二溴化物与式[883742-29-8]的硼酸频哪醇酯在Suzuki偶联反应中反应以产生式7化合物。1H-NMR数据(ppm,CDCl3):8.442H bs,7.232H bs,6.942H bs,6.752H d,4.144H d,2.624H t,1.922H m,1.71-1.604H m,1.45-1.1560H m,0.926H t,0.856H t,0.826H t;
b)根据化合物[1220883-03-3]利用N-溴琥珀酰亚胺(NBS)溴化式7的化合物以产生式8化合物。1H-NMR数据(ppm,CDCl3):8.452H bs,7.082H bs,6.732H d,4.094H d,2.574H t,1.932H m,1.70-1.554H m,1.48-1.1560H m,0.906H t,0.846H t,0.836H t;
c)以类似于实施例1c)的方式由化合物8和噻吩二硼酸频哪醇酯[175361-81-6]开始合成式9的聚合物。Soxhlet萃取的四氢呋喃级分含有Mw为36,200且多分散性为1.86(通过高温GPC测量)的式9的聚合物。
实施例6
以类似于实施例1c)的方式由0.8当量化合物8、0.2当量化合物[214493-03-5]和1当量噻吩二硼酸频哪醇酯[175361-81-6]开始合成式10的聚合物。式10的粗制聚合物的Mw为11,500且多分散性为1.90(通过高温GPC测量)。
实施例7
以类似于实施例1c)的方式由0.5当量化合物8、0.5当量化合物[214493-03-5]和1当量噻吩二硼酸频哪醇酯[175361-81-6]开始合成式11的聚合物。式11的粗制聚合物的Mw为9,900且多分散性为1.61(通过高温GPC测量)。
实施例8
以类似于实施例1c)的方式由化合物[1000623-98-2]和呋喃二硼酸频哪醇酯[476004-83-8]开始合成式12的聚合物。Soxhlet萃取的四氢呋喃级分含有Mw为60,500且多分散性为2.28(通过高温GPC测量)的式12的聚合物。
实施例9
a)根据化合物[1220883-00-0]使式[1000623-98-2]的二溴化物和式[883742-29-8]的硼酸频哪醇酯在Suzuki偶联反应中反应以产生式13的化合物。
b)根据化合物[1220883-03-3]利用N-溴琥珀酰亚胺(NBS)溴化式13的化合物以产生式14的化合物。
c)以类似于实施例1c)的方式由化合物14和呋喃二硼酸频哪醇酯[476004-83-8]开始合成式15的聚合物。Soxhlet萃取的四氢呋喃级分含有Mw为40,200且多分散性为2.10(通过高温GPC测量)的式15的聚合物。
实施例10
以类似于实施例1c)的方式由0.8当量化合物14、0.2当量化合物[214493-03-5]和1当量呋喃二硼酸频哪醇酯[476004-83-8]开始合成式16的聚合物。Soxhlet萃取的四氢呋喃级分含有Mw为27,100且多分散性为1.99(通过高温GPC测量)的式16的聚合物。
实施例11
以类似于实施例1c)的方式由0.5当量化合物14、0.5当量化合物[214493-03-5]和1当量呋喃二硼酸频哪醇酯[476004-83-8]开始合成式17的聚合物。Soxhlet萃取的四氢呋喃级分含有Mw为22,600且多分散性为2.00(通过高温GPC测量)的式17的聚合物。
实施例12
以类似于实施例1c)的方式由化合物[1000623-98-2]和吡咯二硼酸频哪醇酯[476004-84-9]开始合成式18的聚合物。式18的粗制聚合物的Mw为8,500且多分散性为2.43(通过高温GPC测量)。
实施例13
以类似于实施例1c)的方式由化合物14和吡咯二硼酸频哪醇酯[476004-84-9]开始合成式19的聚合物。式19的粗制聚合物的Mw为5,000且多分散性为2.15(通过高温GPC测量)。
实施例14
以类似于实施例1c)的方式由0.8当量化合物14、0.2当量化合物[214493-03-5]和1当量吡咯二硼酸频哪醇酯[476004-84-9]开始合成式20的聚合物。式20的粗制聚合物的Mw为5,500且多分散性为1.87(通过高温GPC测量)。
实施例15
以类似于实施例1c)的方式由0.5当量化合物14、0.5当量化合物[214493-03-5]和1当量吡咯二硼酸频哪醇酯[476004-84-9]开始合成式21的聚合物。式21的粗制聚合物的Mw为3,200且多分散性为1.77(通过高温GPC测量)。
应用实施例1:半导体聚合物3的光伏应用
基于聚合物的本体异质结太阳能电池
太阳能电池具有下列结构:Al电极/LiF层/有机层(包含聚合物3)和[70]PCBM/[聚(3,4-亚乙基二氧基噻吩)(PEDOT)与聚(苯乙烯磺酸)(PSS)]/ITO电极/玻璃基材的混合物。通过将PEDOT-PSS层旋涂于玻璃基材上的预图案化ITO上来制造太阳能电池。随后由oDCB(有机层)旋涂聚合物3(1重量%):[70]PCBM(经取代C70富勒烯)的1:1.5混合物。LiF和Al在高真空下经由阴影掩模升华。
太阳能电池性能
在太阳光模拟器下测量太阳能电池。随后利用外部量子效率(EQE)图表在AM1.5条件下估计电流。该测量获得以下值:Jsc=8.5mA/cm2,FF=0.58和Voc=0.82V,且所估计的总效率为4.04%。
实施例16
以类似于实施例1c)的方式由0.96g化合物2、508.6g化合物22开始合成式23的聚合物。使用不同溶剂:四氢呋喃、氯仿和邻二氯苯通过Soxhlet萃取纯化聚合物。720mg邻二氯苯级分含有Mw为100,000且多分散性为2.59(通过高温GPC测量)的式16的聚合物。
应用实施例2:基于聚合物23的有机场效应晶体管
在所有实验中使用具有p-Si栅极(10cm)的底部栅极薄膜晶体管(TFT)结构。将300nm厚的高质量热SiO2层用作栅极绝缘体,Ci=32.6nF/cm2电容/单元面积。通过光刻直接在栅极氧化物上将源电极和漏电极图案化。使用限定具有宽度W=10mm和各种长度L=4m、8m、15m、30m的沟槽的金源电极和漏电极。在沉积有机半导体之前,通过以下方式来得到SiO2表面:在160℃下与六-二甲基硅氮烷(HMDS)一起在饱和硅烷蒸气中暴露2小时,以800rpm(转/分钟)的旋转速度将HMDS旋涂约1分钟,或在60℃下使用甲苯中的十八烷基三氯硅烷(OTS)的0.1M溶液将基材处理20分钟。使用异丙醇冲洗后,将基材干燥。
通过旋涂或滴注在邻二氯苯的0.5%(w/w)溶液中的实施例16中获得的式23的DPP衍生物来制造半导体薄膜。以1000rpm(转/分钟)的旋转速度在环境条件中经约60秒来进行旋涂。在100℃下干燥15分钟后以沉淀后原样评价该器件。
邻二氯苯中的晶体管性能
在自动晶体管探测器(TP-10)上测量晶体管的特征。
根据对饱和传输特性的平方根的线性拟合,在干燥后可测得场效应迁移率为1.1×10-2cm2/Vs且开/关电流比为2.7×105。阈值电压为约2.3V。应用实施例3:基于聚合物23的有机本体异质结太阳能电池
太阳能电池具有下列结构:Al电极/LiF层/有机层(包括本发明化合物)/[聚(3,4-亚乙基二氧基噻吩)(PEDOT):聚(苯乙烯磺酸)(PSS)]/ITO电极/玻璃基材。通过将PEDOT:PSS层旋涂于玻璃基材上的预图案化ITO上来制造太阳能电池。随后旋涂式23化合物(0.8重量%):[60]PCBM或[70]PCBM(经取代C60或C70富勒烯)的1:2混合物(有机层)。LiF和Al在高真空下经由阴影掩模升华。
太阳能电池性能
在太阳光模拟器下测量太阳能电池。随后利用外部量子效率(EQE)图表在AM1.5条件下估计电流。该测量获得以下值:Jsc=14.35mA/cm2,FF=0.61和Voc=0.72V,且所估计的总效率为6.3%。
实施例17:聚合物26的合成
a)向1.05g 24在20ml无水THF中的冷却(-78℃)溶液中添加4.5ml丁基锂(2.5M,在己烷中)。将所得溶液在0℃下搅拌15分钟并冷却至-78℃。逐滴添加5.2g 2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环,在-78℃下保持5分钟,随后将该溶液缓慢温热至室温并继续搅拌30分钟。通过添加50ml HCl(10%)来终止反应且用40ml乙酸乙酯将产物萃取两次。干燥并蒸发合并的有机萃取物以产生粗制25,通过由9:1二异丙醚:甲苯结晶对其进行纯化,以白色粉末获得1.77g标题化合物。
b)在氩气下将0.96g 2、0.5g化合物25、15mg Pd(乙酸酯)2、76mg2-(二叔丁基膦基)-1-苯基吡咯与60ml四氢呋喃混合并温热至40℃。随后向该反应混合物中添加0.29g氢氧化锂溶液。随后使反应混合物回流4小时并冷却至室温。使用甲醇使绿-蓝色混合物沉淀并过滤。将滤液溶解于氯仿中并使用1%NaCN水溶液回流3小时。用水洗涤有机相且随后干燥并蒸发。用甲醇沉淀聚合物并在Soxhlet中利用THF、氯仿和二氯苯分级分离沉淀。二氯苯级分含有610mg所需聚合物26。Mw=31,500,多分散性=1.65(由HT-GPC测量)。
应用实施例4:基于聚合物26的有机本体异质结太阳能电池
太阳能电池具有下列结构:Al电极/LiF层/有机层(包括本发明化合物)/[聚(3,4-亚乙基二氧基噻吩)(PEDOT):聚(苯乙烯磺酸)(PSS)]/ITO电极/玻璃基材。通过将PEDOT:PSS层旋涂于玻璃基材上的预图案化ITO上来制造太阳能电池。然后,旋涂式26化合物(1重量%):[60]PCBM或[70]PCBM(经取代C60或C70富勒烯)的1:1.5混合物(有机层)。LiF和Al在高真空下经由阴影掩模升华。
太阳能电池性能
在AM1.5G条件,使用基于氙灯的太阳能模拟器辐照(100mW/cm2)且器件面积为0.09cm2下测量太阳能电池特性。在该条件下,测得效率为5.07%(其中Jsc=10.90mA/cm2,FF=0.57且Voc=0.82V)。
实施例18:聚合物29的合成
a)以类似于实施例17a)的方式合成化合物28。
b)以类似于实施例17b)的方式合成聚合物29。
实施例19
a)向200ml叔戊醇中添加5.77g钠和12mg FeCl3。随后将混合物加热至90℃直至所有钠金属均反应。随后逐份添加8.34g 2-呋喃腈[617-90-3]且随后逐份添加20g[1224573-55-0]。反应混合物的颜色变为红色。将反应混合物于90℃下搅拌过夜。将反应混合物倾倒于冰水上并过滤沉淀。用水、丙酮和甲醇和水洗涤滤饼且随后干燥以产生式30的化合物。1H-NMR数据(ppm,DMSO-d6):8.211H d,8.061H d,7.961H dxd,7.671H d,7.301H dxd,6.841H d。
b)以类似于实施例1a)的方式用2-己基癸基碘化物[1044598-79-9]烷基化式30化合物以产生式31化合物。化合物31未经进一步纯化即直接用于下一步骤。
c)以类似于实施例1b)的方式用N-溴琥珀酰亚胺(NBS)溴化式31的化合物以产生式32的化合物。1H-NMR数据(ppm,CDCl3):8.541H d,8.261H d,7.141H d,6.551H d,3.922H d,3.852H d,1.801H m,1.721H m,1.35-1.0548H m,0.776H t,0.766H t。
d)以类似于实施例1c)的方式使式32的二溴化物与噻吩二硼酸频哪醇-酯[175361-81-6]以Suzuki偶联反应反应以产生式33的化合物。
实施例20
以类似于实施例1c)的方式使式32的二溴化物与萘二硼酸频哪醇酯[849543-98-2]以Suzuki偶联反应反应以产生式34的化合物。
实施例21
a)以类似于实施例1a)的方式利用2-乙基己基碘化物[1653-16-3]烷基化二呋喃基二酮基吡咯并吡咯[88949-34-2]以产生式35的化合物。1H-NMR数据(ppm,CDCl3):8.332H dxd,7.612H d,6.692H dxd,4.054H d,1.752H m,1.45-1.2516H m,0.906H t,0.876H t。
b)以类似于实施例1b)的方式利用N-溴琥珀酰亚胺(NBS)溴化式35的化合物以产生式36的化合物。1H-NMR数据(ppm,CDCl3):8.302H d,6.622H d,3.994H d,1.742H m,1.45-1.2516H m,0.926H t,0.886H t。
实施例22
a)以类似于实施例1a)的方式利用1-十二烷基碘化物[4292-19-7]烷基化二呋喃基二酮基吡咯并吡咯[88949-34-2]以产生式37的化合物。1H-NMR数据(ppm,CDCl3):8.302H dxd,7.632H d,6.692H dxd,4.114H t,1.694H m,1.45-1.2036H m,0.886H t。
b)以类似于实施例1b)的方式利用N-溴琥珀酰亚胺(NBS)溴化式37的化合物以产生式38的化合物。1H-NMR数据(ppm,CDCl3):8.252H d,6.632H d,4.054H t,1.674H m,1.45-1.2536H m,0.886H t。
实施例23
a)以类似于实施例1a)的方式利用2-丁基辛基碘化物[1256345-37-5]烷基化二呋喃基二酮基吡咯并吡咯[88949-34-2]以产生式39的化合物。1H-NMR数据(ppm,CDCl3):8.332H dxd,7.602H d,6.692H dxd,4.034H d,1.802H m,1.45-1.2032H m,0.866H t,0.846H t。
b)以类似于实施例1b)的方式利用N-溴琥珀酰亚胺(NBS)溴化式39的化合物以产生式40的化合物。1H-NMR数据(ppm,CDCl3):8.292H d,6.622H d,3.984H d,1.782H m,1.45-1.2032H m,0.876H t,0.846H t。
c)以类似于实施例1c)的方式使式40的二溴化物与二噻吩二硼酸频哪醇酯[239075-02-6]以Suzuki偶联反应反应以产生式41的化合物。氯仿级分含有Mw为18,200且多分散性为1.61(通过高温GPC测量)的聚合物。
Claims (15)
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1,r=0.985-0.005,s=0.005-0.985,t=0.985-0.005,u=0.005-0.985,且其中r+s+t+u=1,
a'为整数1或2,
b为整数1或2,
c为0或整数1或2,
d为0或整数1或2,
e为0或整数1或2,
f为0或整数1或2,
R1和R2可相同或不同且为选自氢、C1-C100烷基、-COOR203;C1-C100烷基,其经一个或多个卤原子、羟基、硝基、-CN或C6-C18芳基取代和/或被-O-、-COO-、-OCO-或-S-间隔;C7-C100芳基烷基、氨基甲酰基;C5-C12环烷基,其可经C1-C8烷基和/或C1-C8烷氧基取代1-3次;C6-C24芳基,尤其是苯基或1-或2-萘基,其可经C1-C8烷基、C1-C8硫代烷氧基和/或C1-C8烷氧基取代1-3次;或五氟苯基,R203为C1-C50烷基,尤其是C4-C25烷基;
R99、R104和R104'彼此独立地为氢、卤素,尤其是F;或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;C7-C25芳基烷基或C1-C25烷氧基,
R105、R105′、R106和R106'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳基烷基或C1-C18烷氧基;
R107为C7-C25芳基烷基、C6-C18芳基;经C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C25烷基;被-O-或-S-间隔的C1-C25烷基;或-COOR119;
R116为氢、C7-C25芳基烷基、C6-C18芳基;经C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C25烷基;被-O-或-S-间隔的C1-C25烷基;或-COOR119;
R119为C1-C25烷基、经E'取代和/或被D'间隔的C1-C25烷基、C7-C25芳基烷基、C6-C24芳基、经G取代的C6-C24芳基或C7-C25芳烷基,
R108和R109彼此独立地为H、C1-C25烷基、经E'取代和/或被D'间隔的C1-C25烷基、C7-C25芳基烷基、C6-C24芳基、经G取代的C6-C24芳基、C2-C20杂芳基、经G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、经E'取代和/或被D'间隔的C1-C18烷氧基或C7-C25芳烷基,或R108与R109一起形成式=CR110R111的基团,其中
R110和R111彼此独立地为H、C1-C18烷基、经E'取代和/或被D'间隔的C1-C18烷基、C6-C24芳基、经G取代的C6-C24芳基或C2-C20杂芳基或经G取代的C2-C20杂芳基,或
R108与R109一起形成5或6员环,其可任选地经以下基团取代:C1-C18烷基、经E'取代和/或被D'间隔的C1-C18烷基、C6-C24芳基、经G取代的C6-C24芳基、C2-C20杂芳基、经G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、经E'取代和/或被D'间隔的C1-C18烷氧基或C7-C25芳烷基,
D'为-CO-、-COO-、-S-、-O-或-NR112-,
E'为C1-C8硫代烷氧基、C1-C8烷氧基、CN、-NR112R113、-CONR112R113或卤素,
G为E'或C1-C18烷基,且
R112和R113彼此独立地为H;C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或被-O-间隔的C1-C18烷基,
B、D和E彼此独立地为下式的基团:
(VI)或式IV,条件为若B、D和E为式IV的基团,则其不同于A,其中
k为1,
l为0或1,
r为0或1,
z为0或1,
a为整数1-5,尤其是1-3,
g为整数1或2,
h为整数1或2,
i为0或整数1或2,
j为0或整数1或2,
k为0或整数1或2,
l为0或整数1或2,
R1′和R2'彼此独立地具有R1的含义,
Ar8、Ar8′、Ar9、Ar9′、Ar10和Ar10'彼此独立地具有Ar2的含义,
Ar4、Ar5、Ar6和Ar7彼此独立地为下式的基团:
Ar20为亚芳基或亚杂芳基,其各自可任选地经取代,
R118具有R116的含义,
R12和R12'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;C1-C25烷氧基、C7-C25芳基烷基或
R13为C1-C10烷基或三(C1-C8烷基)甲硅烷基,
R14、R14'、R15、R15'、R17和R17'彼此独立地为H;或可任选地被一个或多个氧原子间隔的C1-C25烷基,尤其是C6-C25烷基;
R18和R18'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;C7-C25芳烷基或C1-C25烷氧基;
R19为氢、C7-C25芳烷基、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;
R20和R20′彼此独立地为氢、C7-C25芳烷基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基,
R100和R100′彼此独立地为H、F、C1-C18烷基、被O间隔的C1-C18烷基、C1-C18烷氧基、被O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R303、R304、R305和R306彼此独立地为H、F、C1-C18烷基、被O间隔的C1-C18烷基、C1-C18烷氧基、被O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R307和R308彼此独立地为H或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;
R309、R310、R311和R312彼此独立地为H、C1-C25烷氧基或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;
R101和R101′彼此独立地为H、F、C1-C18烷基、被O间隔的C1-C18烷基、C1-C18烷氧基、被O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R102和R102'彼此独立地为H、卤素、可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳基烷基或C1-C25烷氧基;
R103和R103'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基;可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基;C7-C25芳基烷基、CN或C1-C25烷氧基;或
R103和R103′一起形成环,
R115和R115'彼此独立地为氢、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;或C7-C25芳基烷基,
R117和R117'彼此独立地为C1-C35烷基、C7-C25芳基烷基或任选地可经C1-C8烷基和/或C1-C8烷氧基取代1-3次的苯基,
R120和R120′彼此独立地为氢、可任选地被一个或多个氧或硫原子间隔的C 1-C35烷基或C7-C25芳基烷基,
R121为H、可任选地被一个或多个氧或硫原子间隔的C1-C18烷基、C1-C18全氟烷基、可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基;可任选地经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;或CN,
4.如权利要求1-3中任一项的聚合物,其中B、D和E彼此独立地为下式的基团
R303、R304、R305、R306、R307、R308、R309、R310、R311、R312、R100、R100′、R101、R101′、R102、R102′、R103、R103′、R120和R120′如权利要求1中所定义,a为整数1-5,尤其是1-3,
X1和X2中的一个为N且另一个为CH,
X5和X6中的一个为N且另一个为CR14,
R114和R114'彼此独立地为氢或C1-C18烷基,
R116为H或C1-C25烷基,R117为C1-C25烷基,
R13为C1-C10烷基或三(C1-C8烷基)甲硅烷基,
R15、R15'、R17和R17'彼此独立地为H;或可任选地被一个或多个氧原子间隔的C1-C25烷基,尤其是C6-C25烷基,
R14为C1-C25烷基,尤其是C6-C25烷基,其可任选地被一个或多个氧原子间隔,
R18和R18'彼此独立地为氢、卤素;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;C7-C25芳烷基或C1-C25烷氧基;
R19为氢、C7-C25芳烷基、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基;且
R20和R20'彼此独立地为氢、C7-C25芳烷基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基。
6.如权利要求1的聚合物,其为包含下式的重复单元的聚合物
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1;
A为如权利要求3中所定义的式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
B和D彼此独立地为如权利要求4中所定义的式Va、Vb、Vc,尤其是Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx,尤其是Vy、Vz或Va'的基团;或
其为包含下式的重复单元的聚合物
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1;A为如权利要求3中所定义的式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
B为式的基团,R1和R2为C1-C35烷基,尤其是C8-C35烷基,
7.如权利要求1的聚合物,其包含下式的重复单元
r=0.985-0.005,s=0.005-0.985,t=0.005-0.985,u=0.005-0.985,且其中r+s+t+u=1,
A为如权利要求3中所定义的式IVa、IVc、IVe、IVg、IVh、IVi、IVj或IVk的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
8.如权利要求1的聚合物,其为下式的聚合物
其中R1、R2、R1′和R2'彼此独立地为C1-C36烷基,尤其是C8-C36烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选地被一个或多个氧或硫原子间隔,
R15、R15'、R17和R17'彼此独立地为H;或可任选地被一个或多个氧原子间隔的C1-C25烷基,尤其是C6-C25烷基,
R20和R20′彼此独立地为氢、C7-C25芳烷基;可任选地被一个或多个氧或硫原子间隔的C1-C25烷基,尤其是C4-C25烷基,
R100和R100'为H,
R101和R101'为H、C1-C25烷基或C1-C25烷氧基,
R102和R102'为H或C1-C25烷基,
R103和R103'为H或C1-C25烷基,
R116为H或C1-C25烷基,
R120和R120'为C1-C35烷基,
n为4-1000,尤其是4-200,非常特别是5-100,且
x=0.995-0.005,y=0.005-0.995,尤其是x=0.2-0.8,y=0.8-0.2,且其中x+y=1。
9.一种有机半导体材料、层或组件,包含如权利要求1-8中任一项的聚合物。
10.一种半导体器件,包含如权利要求1-8中任一项的聚合物或如权利要求9的有机半导体材料、层或组件。
11.如权利要求10的半导体器件,其为有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管。
12.如权利要求10的半导体器件,其中该PV器件依次包含:
(a)阴极(电极),
(b)任选的过渡层,例如碱金属卤化物,尤其是氟化锂,
(c)光活性层,
(d)任选的平滑层,
(e)阳极(电极),和
(f)基材。
13.一种制备有机半导体器件的方法,该方法包含将有机溶剂中的如权利要求1-8中任一项的聚合物的溶液和/或分散体施加至合适基材上,并去除该溶剂。
14.如权利要求1-8中任一项的聚合物或如权利要求9的有机半导体材料、层或组件在PV器件、光电二极管或有机场效应晶体管中的用途。
15.一种下式的化合物
a'、b、c、d、e、f、R1、R2、Ar1、Ar1′、Ar2、Ar2'、Ar3和Ar3′如权利要求1中所定义且X11在每次出现时独立地为ZnX12、-SnR207R208R209,其中R207、R208和R209相同或不同且为H或C1-C6烷基,其中两个基团任选地形成共同环且这些基团任选地支化或未支化;X12为卤原子,非常特别为I或Br;-OS(O)2CF3、-OS(O)2-芳基,尤其是-OS(O)2CH3、-B(OH)2、-B(OH)3 -、-BF3、-B(OY1)2、其中Y1在每次出现时独立地为C1-C10烷基且Y2在每次出现时独立地为C2-C10亚烷基,例如-CY3Y4-CY5Y6-或-CY7Y8-CY9Y10-CY11Y12-,其中Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11和Y12彼此独立地为氢或C1-C10烷基,尤其是-C(CH3)2C(CH3)2-或-C(CH3)2CH2C(CH3)2-、-CH2C(CH3)2CH2-,且Y13和Y14彼此独立地为氢或C1-C10烷基。
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EP (1) | EP2571919B1 (zh) |
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