Diketopyrrolopyrrole polymers and small molecules
The present invention relates to polymers, comprising a repeating unit of the formula (I), and compounds of formula (II), wherein Y, Y 15 , Y 16 and Y 17 are independently of each other a group of formula (a) characterized in that the polymers and compounds comprise silicon-containing solubilizing side chains and their use as organic semiconductor in organic devices, especially in organic photovoltaics and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers and compounds according to the invention can have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers and compounds according to the invention are used in organic field effect transistors, organic photovoltaics and photodiodes.
1. A polymer comprising a repeating unit of the formula
wherein
a is 0, 1, 2, or 3, a′ is 0, 1, 2, or 3; b is 0, 1, 2, or 3; b′ is 0, 1, 2, or 3; c is 0, 1, 2, or 3; c′ is 0, 1, 2, or 3;
R 1 and R 2 may be the same or different and are selected from the group consisting of a C 1 -C 100 alkyl group, which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, —COO—, —CO—, —OCO—, C 6 -C 24 arylene, C 2 -C 20 heteroarylene, C 3 -C 12 cycloalkylene, or D Si ,
a C 2 -C 100 alkenyl group, which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, —COO—, —CO—, —OCO—, C 6 -C 24 arylene, C 2 -C 20 heteroarylene, C 3 -C 12 cycloalkylene, or D Si ,
a C 3 -C 100 alkinyl group, which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, —COO—, —CO—, —OCO—, C 6 -C 24 arylene, C 2 -C 20 heteroarylene, C 3 -C 12 cycloalkylene, or D Si ,
a C 3 -C 12 cycloalkyl group, which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, —COO—, —CO—, —OCO—, C 6 -C 24 arylene, C 2 -C 20 heteroarylene, C 3 -C 12 cycloalkylene, or D Si ,
a C 6 -C 24 aryl group, which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ;
a C 2 -C 20 heteroaryl group, which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ; and
—CO—C 1 -C 18 alkyl, —CO—C 5 -C 12 cycloalkyl, —COO—C 1 -C 18 alkyl which can optionally be substituted one or more times with C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, nitro, cyano, vinyl, allyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, or E Si ; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, —COO—, —CO—, —OCO—, C 6 -C 24 arylene, C 2 -C 20 heteroarylene, C 3 -C 12 cycloalkylene, or D Si ; wherein
E Si is —SiR 161 R 162 R 163 or —O—SiR 161 R 162 R 163 ,
D Si is —SiR 161 R 162 —, —SiR 161 R 162 —(O—SiR 161 R 162 ) d — or —O—SiR 161 R 162 —,
R 161 , R 162 and R 163 are independently of each other hydrogen, C 1 -C 25 alkyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, —O—SiR 164 R 165 R 166 , —(O—SiR 164 R 165 ) d —R 166 , C 1 -C 25 alkoxy, C 3 -C 24 (hetero)aryloxy, NR 167 R 168 , halogen, C 1 -C 25 acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C 1 -C 24 alkyl, halogen, cyano or C 1 -C 25 alkoxy;
R 164 , R 165 and R 166 are independently of each other hydrogen, C 1 -C 25 alkyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, —O—SiR 169 R 170 R 171 , —(O—SiR 169 R 170 ) d —R 171 , C 1 -C 25 alkoxy, C 3 -C 24 (hetero)aryloxy, NR 167 R 168 , halogen, C 1 -C 25 acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C 1 -C 24 alkyl, halogen, cyano or C 1 -C 25 alkoxy;
R 169 , R 170 and R 171 are independently of each other hydrogen, C 1 -C 25 alkyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, —O—Si(CH 3 ) 3 , C 1 -C 25 alkoxy, C 3 -C 24 (hetero)aryloxy, NR 167 R 168 , halogen, C 1 -C 25 acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C 1 -C 24 alkyl, halogen, cyano or C 1 -C 25 alkoxy;
R 167 and R 168 are independently of each other hydrogen, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy, or C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or C 7 -C 25 arylalkyl;
d is an integer from 1 to 50;
R 39 is hydrogen, C 1 -C 18 alkyl, C 1 -C 18 haloalkyl, C 7 -C 25 arylalkyl, or C 1 -C 18 alkanoyl,
Ar 1 , Ar 1′ , Ar 2 , Ar 2′ , Ar 3 and Ar 3′ are independently of each other
wherein
X is —O—, —S—, —NR 8 —, —Si(R 11 )(R 11′ )—, —Ge(R 11 )(R 11′ )—, —C(R 7 )(R 7′ )—, —C(═O)—, —C(═CR 104 R 104′ )—,
R 3 and R 3′ are independently of each other hydrogen, halogen, E Si , halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 arylalkyl, C 1 -C 25 alkyl substituted with one or more E Si , or C 1 -C 25 alkoxy;
R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are independently of each other hydrogen, halogen, E Si , halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 arylalkyl, C 1 -C 25 alkyl substituted with one or more E Si , or C 1 -C 25 alkoxy;
R 7 , R 7′ , R 9 and R 9′ are independently of each other hydrogen, C 1 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C 1 -C 25 alkyl substituted with one or more E Si , or C 7 -C 25 arylalkyl, or R 7 and R 7′ , or R 9 and R 9′ are together ═CR 104 R 104′ ;
R 8 and R 8′ are independently of each other hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkyl substituted with one or more E Si , or C 7 -C 25 arylalkyl,
R 11 and R 11′ are independently of each other C 1 -C 25 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 12 and R 12′ are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or —≡—R 13 , wherein R 13 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group;
Ar 1 , Ar 1′ , Ar 2 , Ar 2′ , Ar 3 and Ar 3′ are independently of each other
wherein
X 1′ is S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 108 )(R 109 )—, —C(═O)—, —C(═CR 104 R 104′ )—,
R 104 and R 104′ are independently of each other hydrogen, cyano, COOR 103 , a C 1 -C 25 alkyl group, a C 6 -C 24 aryl or C 2 -C 20 heteroaryl;
R 103 is C 1 -C 25 alkyl, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or is C 7 -C 25 arylalkyl;
R 105 , R 105′ , R 106 and R 106′ are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 arylalkyl, or C 1 -C 18 alkoxy,
R 107 is hydrogen, C 7 -C 25 arylalkyl, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy, C 1 -C 18 perfluoroalkyl, C 1 -C 25 alkyl, which may be interrupted by —O—, or —S—; or —COOR 103 ;
R 108 and R 109 are independently of each other H, C 1 -C 25 alkyl, C 1 -C 25 alkyl which is substituted by E and/or interrupted by D, C 7 -C 25 arylalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
R 108 and R 109 together form a group of formula ═CR 110 R 111 , wherein
R 110 and R 111 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 108 and R 109 together form a five or six membered ring, which optionally can be substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl,
D is —CO—, —COO—, —S—, —O—, or —NR 112 —,
E is C 1 -C 8 thioalkoxy, C 1 -C 8 alkoxy, CN, —NR 112 R 113 , —CONR 112 R 113 , or halogen,
G is E, or C 1 -C 18 alkyl, and
R 112 and R 113 are independently of each other H, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by —O—,
R 114 is C 1 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms,
R 115 and R 115′ are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or —≡—R 116 , wherein R 116 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group;
R 117 and R 117′ are independently of each other C 1 -C 25 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 118 , R 119 , R 120 and R 121 are independently of each other hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 122 and R 122′ are independently of each other hydrogen, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy, or C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or C 7 -C 25 arylalkyl,
with the proviso that at least one of the groups R 1 , R 2 , R 3 , R 3′ , R 4 , R 4′ , R 5 , R 5′ , R 6 , R 6′ , R 7 , R 7′ , R 8 , R 8′ , R 9 and R 9′ comprise E Si and/or D Si ;
and wherein the polymer comprises at least one unit of the formula Ia to Ie,
wherein
R 1 and R 2 may be the same or different and are selected from C 1 -C 8 alkyl which is substituted with E Si ,
E Si is —SiR 161 R 162 R 163 ;
R 161 , R 162 and R 163 are independently of each other C 1 -C 8 alkyl, C 5 -C 6 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, —O—SiR 164 R 165 R 166 , —(O—SiR 164 R 165 ) d —R 166 , or phenyl;
R 164 , R 165 , R 166 are independently of each other C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, —O—SiR 169 R 170 R 171 , —(O—SiR 169 R 170 ) d —R 171 , or phenyl;
R 169 , R 170 , R 171 are independently of each other C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, —O—Si(CH 3 ) 3 , or phenyl;
d is an integer from 1 to 10;
R 3 and R 3′ are independently of each other hydrogen, or C 1 -C 25 alkyl; and
R 8 and R 8′ are independently of each other hydrogen, or C 1 -C 25 alkyl.
2. A polymer comprising a repeating unit of the formula
wherein
R 1 and R 2 may be the same or different and are selected from C 1 -C 25 alkyl, which is substituted one or more times with E Si and/or interrupted one or more times with D Si , C 1 -C 25 haloalkyl, which is substituted one or more times with E Si and/or interrupted one or more times with D Si , C 7 -C 25 arylalkyl, which is substituted one or more times with E Si and/or interrupted one or more times with D Si , C 2 -C 25 alkenyl, which is substituted one or more times with E Si and/or interrupted one or more times with D Si , C 2 -C 25 haloalkenyl, which is substituted one or more times with E Si and/or interrupted one or more times with D Si , C 5 -C 12 cycloalkyl, which is substituted one or more times with E Si and/or interrupted one or more times with D Si , phenyl, or naphthyl which are substituted one or more times with E Si , and
a is 1, 2, or 3,
a′ is 1, 2, or 3,
wherein
E Si is —SiR 161 R 162 R 163 or —O—SiR 161 R 162 R 163 ,
D Si is —SiR 161 R 162 —, —SiR 161 R 162 —(O—SiR 161 R 162 ) d — or —O—SiR 161 R 162 —,
R 161 , R 162 and R 163 are independently of each other hydrogen, C 1 -C 25 alkyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, —O—SiR 164 R 165 R 166 , —(O—SiR 164 R 165 ) d —R 166 , C 1 -C 25 alkoxy, C 3 -C 24 (hetero)aryloxy, NR 167 R 168 , halogen, C 1 -C 25 acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C 1 -C 24 alkyl, halogen, cyano or C 1 -C 25 alkoxy;
R 164 , R 165 and R 166 are independently of each other hydrogen, C 1 -C 25 alkyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, —O—SiR 169 R 170 R 171 , —(O—SiR 169 R 170 ) d —R 171 , C 1 -C 25 alkoxy, C 3 -C 24 (hetero)aryloxy, NR 167 R 168 , halogen, C 1 -C 25 acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C 1 -C 24 alkyl, halogen, cyano or C 1 -C 25 alkoxy;
R 169 , R 170 and R 171 are independently of each other hydrogen, C 1 -C 25 alkyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, —O—Si(CH 3 ) 3 , C 1 -C 25 alkoxy, C 3 -C 24 (hetero)aryloxy, NR 167 R 168 , halogen, C 1 -C 25 acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C 1 -C 24 alkyl, halogen, cyano or C 1 -C 25 alkoxy;
R 167 and R 168 are independently of each other hydrogen, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy, or C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or C 7 -C 25 arylalkyl; and
d is an integer from 1 to 50;
Ar 1 and Ar 1′ are independently of each other
wherein
X is —O—, —S—, —NR 8 —, —Si(R 11 )(R 11′ )—, —Ge(R 11 )(R 11′ )—, —C(R 7 )(R 7′ )—, —C(═O)—, —C(═CR 104 R 104′ )—,
R 3 and R 3′ are independently of each other hydrogen, halogen, E Si , halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 arylalkyl, C 1 -C 25 alkyl substituted with one or more E Si , or C 1 -C 25 alkoxy;
R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are independently of each other hydrogen, halogen, E Si , halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 arylalkyl, C 1 -C 25 alkyl substituted with one or more E Si , or C 1 -C 25 alkoxy;
R 7 , R 7′ , R 9 and R 9′ are independently of each other hydrogen, C 1 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C 1 -C 25 alkyl substituted with one or more E Si , or C 7 -C 25 arylalkyl, or R 7 and R 7′ , or R 9 and R 9′ are together ═CR 104 R 104′ ;
R 8 and R 8′ are independently of each other hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkyl substituted with one or more E Si , or C 7 -C 25 arylalkyl,
R 11 and R 11′ are independently of each other C 1 -C 25 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 12 and R 12′ are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or —≡—R 13 , wherein R 13 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group.
3. A polymer, which is a polymer of the formula Ia1 to Ia7,
wherein
n is from 4 to 1000,
R 1 and R 2 may be the same or different and are a C 1 -C 8 alkyl which is substituted with E Si ,
R 3 and R 3′ are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl or C 1 -C 25 alkoxy;
E Si is —SiR 161 R 162 R 163 ;
R 161 , R 162 and R 163 are independently of each other C 1 -C 8 alkyl, C 5 -C 6 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, —O—SiR 164 R 165 R 166 , —(O—SiR 164 R 165 ) d —R 166 , or phenyl;
R 164 , R 165 and R 166 are independently of each other C 1 -C 5 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, —O—SiR 169 R 170 R 171 , —(O—SiR 169 R 170 ) d —R 171 , or phenyl;
R 169 , R 170 and R 171 are independently of each other C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, —O—Si(CH 3 ) 3 , or phenyl;
d is an integer from 1 to 10;
R 3″ and R 3 * are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl or C 1 -C 25 alkoxy;
R 104 and R 104′ are independently of each other hydrogen, cyano, COOR 103 , C 1 -C 25 alkyl, wherein R 103 is C 1 -C 8 alkyl; and
R 105 and R 105′ are independently of each other hydrogen, halogen, cyano, C 1 -C 25 alkyl or C 1 -C 25 alkoxy.
4. An organic semiconductor material, layer or component, comprising the polymer according to claim 1 .
5. An electronic device, comprising the polymer according to claim 1 .
6. The electronic device according to claim 5 , wherein said device is an organic photovoltaic device, a photodiode, or an organic field effect transistor.
7. A method for the preparation of an electronic device, said method comprises
applying a solution and/or dispersion of the polymer according to claim 1 in an organic solvent to a suitable substrate, and
removing the solvent.
8. An organic semiconductor material, layer or component, comprising the polymer according to claim 2 .
9. An electronic device, comprising the polymer according to claim 2 .
10. The electronic device according to claim 9 , wherein said device is an organic photovoltaic device, a photodiode, or an organic field effect transistor.
11. A method for the preparation of an electronic device, said method comprises
applying a solution and/or dispersion of the polymer according to claim 2 in an organic solvent to a suitable substrate, and
removing the solvent.
12. An organic semiconductor material, layer or component, comprising the polymer according to claim 3 .
13. An electronic device, comprising the polymer according to claim 3 .
14. The electronic device according to claim 13 , wherein said device is an organic photovoltaic device, a photodiode, or an organic field effect transistor.
15. A method for the preparation of an electronic device, said method comprises
applying a solution and/or dispersion of the polymer according to claim 3 in an organic solvent to a suitable substrate, and
removing the solvent.
16. The polymer according to claim 1 , wherein R 1 and R 2 are C 1 -C 25 alkyl which is substituted one or more times with E Si and/or interrupted one or more times with D Si .
17. The polymer according to claim 1 , wherein E Si is —SiR 161 R 162 R 163 , wherein R 161 , R 162 and R 163 are independently of each other C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl; phenyl, —O—SiR 164 R 165 R 166 , or —(O—SiR 164 R 165 ) d —R 166 , wherein R 164 , R 165 and R 166 are independently of each other C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, or phenyl, and in case of a group —(O—SiR 164 R 165 ) d —R 166 R 164 and R 165 are independently of each other C 1 -C 8 alkyl, R 166 is C 1 -C 8 alkyl, or phenyl and d is an integer of 2 to 5.
18. The polymer according to claim 1 , wherein D Si is —SiR 161 R 162 —, wherein R 161 and R 162 are independently of each other C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, or phenyl, or —SiR 161 R 162 —(O—SiR 161 R 162 ) d —, wherein d is 2 to 5 and R 161 and R 162 are C 1 -C 25 alkyl.
19. The polymer according to claim 1 , wherein Ar 1 and Ar 1′ are independently of each other a group of formula XIa, XIb, XIc, XIe, XIf, XII, XIp, XIr, XIs, XIx, XIIf, XIIg, XIIIa, XIIId, or XIIIl.
20. The polymer according to claim 2 , wherein R 1 and R 2 are C 1 -C 25 alkyl which is substituted one or more times with E Si and/or interrupted one or more times with D Si .
21. The polymer according to claim 2 , E Si is —SiR 161 R 162 R 163 , wherein R 161 , R 162 and R 163 are independently of each other C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, C 3 -C 12 cycloalkyl, which might optionally be substituted with C 1 -C 4 alkyl; phenyl, —O—SiR 164 R 165 R 166 , or —(O—SiR 164 R 165 ) d —R 166 , wherein R 164 , R 165 and R 166 are independently of each other C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, or phenyl, and in case of a group —(O—SiR 164 R 165 ) d —R 166 R 164 and R 165 are independently of each other C 1 -C 8 alkyl, R 166 is C 1 -C 8 alkyl, or phenyl and d is an integer of 2 to 5.
22. The polymer according to claim 2 , wherein D Si is —SiR 161 R 162 —, wherein R 161 and R 162 are independently of each other C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, C 2 -C 25 alkenyl, or phenyl, or —SiR 161 R 162 —(O—SiR 161 R 162 ) d —, wherein d is 2 to 5 and R 161 and R 162 are C 1 -C 25 alkyl.
23. The polymer according to claim 2 , wherein Ar 1 and Ar 1′ are independently of each other a group of formula XIa, XIb, XIc, XIe, XIf, XII, XIp, XIr, XIs, XIx, XIIf, XIIg, XIIIa, XIIId, or XIIIl.