Polymers and compounds based on dipyrrolo[1,2-B:1',2'-G][2,6]naphthyridine-5,11-dione

1. A compound of formula

R 10 —Ar—Y—Ar′—R 10 ′  (I),

wherein

Ar is a group of formula —[Ar 3 ] c —[Ar 2 ] b —[Ar 1 ] a —**,

Ar′ is a group of formula **—[Ar 1′ ] a′ —[Ar 2′ ] b′ —[Ar 3′ ] c′ —,

Y is a group of formula

wherein

** indicates the bonding to Y,

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;

m1 is 0, 1, or 2;

m2 is 0, 1, or 2;

U 1 is O, or S;

U 2 is O, or S;

T 1 , T 2 , T 3 and T 4 are independently of each other:

a hydrogen, halogen, cyano, —COOR 103 , —OCOR 103 , —NR 112 COR 103 , —CONR 112 R 113 , —OR 103′ , —SR 103′ , —SOR 103′ , —SO 2 R 103′ , —NR 112 SO 2 R 103′ , —NR 112 R 113 , —NO 2 , C 7 -C 25 arylalkyl, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;

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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

a C 2 -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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 ;

a —CO—C 1 -C 18 alkyl group, a —CO—C 5 -C 12 cycloalkyl group, or —COO—C 1 -C 18 alkyl group;

Ar 1 and Ar 1′ are independently of each other

Ar 2 , Ar 2′ , Ar 3 and Ar 3′ have independently of each other the meaning of Ar 1 , or are independently of each other

wherein

X is O, S, Se, Te, or NR 8 ,

X′ is O, or S,

X 1 , X 2 and X 3 are independently of each other S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 108 )(R 109 )—, —C(═O)—, —C(═CR 110 R 111 )—,

X 4 and X 4′ are independently of each other S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 108 )(R 109 )—, —C(═O)—, —C(═CR 110 R 111 )—,

R 3 and R 3′ 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 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ 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 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, or C 1 -C 25 arylalkyl;

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, 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;

R 10 and R 10′ are independently of each other hydrogen, halogen, NO 2 , NR 112 R 113 , cyano, C 1 -C 25 alkyl, C 1 -C 25 alkyl which is substituted one or more times by E and/or interrupted one or more times by D,

 COO—C 1 -C 18 alkyl, C 4 -C 18 cycloalkyl group, C 4 -C 18 cycloalkyl group, which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkylthio, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, C 7 -C 25 aralkyl, which is substituted by G, or a group of formulae IVa to IVk,

wherein X 5 is O, S, Se, Te, or NR 59 ,

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 5 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 is a C 1 -C 8 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group;

R 22 to R 26 and R 29 to R 58 represent independently of each other H, halogen, cyano, NO 2 , NR 112 R 113 , C 1 -C 25 alkyl, C 1 -C 25 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, a C 4 -C 18 cycloalkyl group, a C 4 -C 18 cycloalkyl group, which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 25 alkylthio, C 1 -C 25 alkoxy, C 1 -C 25 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or C 7 -C 25 aralkyl, which is substituted by G,

R 27 and R 28 are independently of each other hydrogen, C 1 -C 25 alkyl, halogen, cyano or C 7 -C 25 aralkyl, or R 27 and R 28 together represent alkylene or alkenylene which may be both bonded via oxygen and/or sulfur to the thienyl residue and which may both have up to 25 carbon atoms,

R 59 is hydrogen, C 6 -C 18 aryl; C 6 -C 15 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,

R 60 is hydrogen, C 1 -C 18 haloalkyl, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 1 -C 18 alkanoyl, or C 7 -C 25 arylalkyl,

R 103 and R 103′ are independently of each other hydrogen, C 1 -C 100 alkyl, C 1 -C 25 alkyl substituted by E and/or interrupted with D, C 2 -C 25 alkenyl, C 2 -C 25 alkenyl substituted by E and/or interrupted with 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, or C 2 -C 20 heteroaryl which is substituted by G,

R 104 and R 104′ are independently of each other hydrogen, CN, C 1 -C 18 alkyl, C 6 -C 10 aryl, which may optionally be substituted by G, or C 2 -C 8 heteroaryl, which may optionally be substituted by G,

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 103 is as defined above;

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 8 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,

wherein

D is —CO—, —COO—, —S—, —O—, or —NR 112 —,

E is C 1 -C 8 alkylthio, 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 is a C 1 -C 8 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, 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; and

E Si is —SiR 161 R 162 R 163 or —O—SiR 161 R 162 R 163 ,

wherein 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 214 and R 215 are independently of each other hydrogen, C 1 -C 18 alkyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, —CN or COOR 216 ; and R 216 is C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, C 7 -C 25 arylalkyl, C 6 -C 24 aryl or C 2 -C 20 heteroaryl.

2. The compound according to claim 1 , which is a compound of formula

3. The compound according to claim 1 , which is a compound of formula

4. The compound according to claim 1 , wherein U 1 and U 2 are O.

5. The compound according to claim 1 , wherein T 1 , T 2 , T 3 and T 4 are H, a C 1 -C 38 alkyl group which can optionally be substituted one or more times with C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, cyano, or E Si ; and/or can optionally be interrupted by —O—, —S—, or —NR 60 —, wherein R 60 is C 1 -C 25 alkyl, or phenylC 1 -C 4 alkyl, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy,

wherein

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 64 R 165 ) d —R 166 , or phenyl;

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, —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; and

d is an integer from 1 to 10.

6. The compound according to claim 1 , wherein

—Ar—R 10 and —Ar′—R 10′ are independently of each other H, F, cyano, C 1 -C 25 alkyl, C 1 -C 25 alkyl substituted with one or more halogen atoms,

wherein

R 3 and R 3′ are independently of each other hydrogen, F, C 1 -C 25 alkyl, or C 1 -C 25 alkoxy,

R 22 , R 23 , R 25 , R 26 , R 27 , R 28 and R 29 to R 33 represent independently of each other H, F, cyano, C 1 -C 25 alkoxy, C 1 -C 25 alkyl substituted with one or more F, or C 1 -C 25 alkyl, and

R 24 is H, F, cyano, NO 2 , NR 112 R 113 , phenyl, C 1 -C 25 alkoxy, C 1 -C 25 alkylthio, C 1 -C 25 alkyl substituted with one or more halogen atoms, or C 1 -C 25 alkyl;

X is O, S, Se, or NR 8 ,

X 5 is O, S, Se, or NR 59 ,

R 58 is H, F, cyano, phenyl, C 1 -C 25 alkoxy, C 1 -C 25 alkylthio, C 1 -C 25 alkyl substituted with one or more halogen atoms, or C 1 -C 25 alkyl;

R 8 and R 59 are hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted one to three times 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 and/or is optionally substituted by one or more F; or C 7 -C 25 arylalkyl, and

R 112 and R 113 are independently of each other hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted one to three times 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 and/or is optionally substituted by one or more F; or C 7 -C 25 arylalkyl.

7. The compound according to claim 1 , which is a compound of formula

wherein

U 1 and U 2 are O,

T 1 and T 2 are H, a C 1 -C 38 alkyl group which can optionally be interrupted by —O—, —S—, or —NR 1 —, wherein R 60 is C 1 -C 25 alkyl, or phenylC 1 -C 4 alkyl, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy,

T 3 and T 4 are H, a C 1 -C 38 alkyl group can optionally be interrupted by —O—, —S—, or —NR 60 —, wherein R 60 is C 1 -C 25 alkyl, or phenylC 1 -C 4 alkyl, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy, and

—Ar—R 10 and —Ar′—R 10′ are independently of each other H, F, cyano, C 1 -C 25 alkyl substituted with one or more fluorine atoms, C 1 -C 25 alkyl,

wherein

R 3 and R 3′ are independently of each other hydrogen, F, C 1 -C 25 alkyl, or C 1 -C 25 alkoxy,

R 22 , R 23 , R 25 , R 26 , R 27 , R 28 and R 29 to R 33 represent independently of each other H, F, cyano, C 1 -C 25 alkoxy, C 1 -C 25 alkyl substituted with one or more F, or C 1 -C 25 alkyl, and

R 24 is H, F, cyano, NO 2 , NR 112 R 113 , CF 3 , phenyl, C 1 -C 25 alkoxy, C 1 -C 25 alkyl substituted with one or more halogen atoms, or C 1 -C 25 alkyl;

X is O, S, Se, or NR 8 ,

X 5 is O, S, Se, or NR 59 ,

R 58 is H, F, cyano, phenyl, C 1 -C 25 alkoxy, C 1 -C 25 alkylthio, C 1 -C 25 alkyl substituted with one or more halogen atoms, or C 1 -C 25 alkyl;

R 8 and R 59 are hydrogen, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted one to three times 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 and/or is optionally substituted by one or more F, or C 7 -C 25 arylalkyl, and

R 112 and R 113 are independently of each other hydrogen, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted one to three times 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 and/or is optionally substituted by one or more F, or C 7 -C 25 arylalkyl.

8. The compound according to claim 1 , which is a compound of formula

9. A polymer comprising a repeating unit of the formula —[(Ar)′—Y—(Ar′) z 2 ]—(V), wherein

z 1 and z 2 are independently of each other 0, or 1,

Y, Ar and Ar′ are defined in claim 1 .

10. The polymer according to claim 9 , comprising a repeating unit of the formula

wherein

z 1 and z 2 are independently of each other 0, or 1.

11. The polymer according to claim 9 , comprising a repeating unit of the formula

12. The polymer according to claim 9 , wherein U 1 and U 2 are O.

13. The polymer according to claim 9 , wherein

T 1 , T 2 , T 3 and T 4 are H, a C 1 -C 38 alkyl group which can optionally be substituted one or more times with C 1 -C 12 alkoxy, halogen, C 5 -C 12 cycloalkyl, or E Si , and/or can optionally be interrupted by —O—, —S—, wherein 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 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 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.

14. The polymer according to claim 9 , wherein —Ar— and —Ar′— are independently of each other a single bond,

wherein

R 3 and R 3′ are independently of each other hydrogen, F, C 1 -C 25 alkoxy, or C 1 -C 25 alkyl,

R 8 is hydrogen, or C 1 -C 25 alkyl, and

R 104 and R 104′ are independently of each other hydrogen, cyano, COOR 103 , or a C 1 -C 25 alkyl group, wherein R 103 is a C 1 -C 25 alkyl group, which can optionally be interrupted by —O—, or —S—.

15. The polymer according to claim 9 , comprising a repeating unit of the formula * A * and a repeating unit * COM 1 *, wherein

A is a repeating unit of formula (V), and

—COM 1 - is a repeating unit, which has the meaning of Ar 2 , or a group of formula

wherein

s is 1,

t is 1,

u is 0 or 1,

v is 0 or 1, and

Ar 4 and Ar 5 are independently of each other a group of formula

wherein

Ar 14 , Ar 15 , Ar 16 and Ar 17 are independently of each other a group of formula

 wherein

one of X 7 and X 8 is N and the other is CR 14 ,

R 14 , R 14′ , R 17 and R 17′ are independently of each other H, F, a C 1 -C 52 alkyl group, or a C 1 -C 25 alkoxy group,

R 200 and R 200′ are independently of each other H, or F,

R 201 and R 202 are independently of each other H, 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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 60 —, CONR 60 —, NR 60 CO—, —COO—, —CO— or —OCO—,

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 , R 60 is hydrogen, C 1 -C 18 haloalkyl, C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; C 1 -C 18 alkanoyl, or C 7 -C 25 arylalkyl,

R 206 is hydrogen, or C 1 -C 25 alkyl, or C 6 -C 18 aryl; C 6 -C 15 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, and

R 304 and R 304′ are independently of each other hydrogen, cyano, COOR 305 , or a C 1 -C 25 alkyl group, wherein R 305 is a C 1 -C 25 alkyl group, which can optionally be interrupted by —O—, or —S—.

16. The polymer according to claim 9 , which is a polymer of the formula

17. An organic semiconductor material, layer or component, comprising a compound according to claim 1 .

18. A semiconductor device, comprising a compound according to claim 1 .

19. The semiconductor device according to claim 18 , which is an organic photovoltaic device, a photodiode, or an organic field effect transistor.

20. A process for the preparation of an organic semiconductor device, which process comprises applying a solution and/or dispersion of a compound according to claim 1 in an organic solvent to a suitable substrate and removing the solvent.

21. A PV device, photodiode, IR absorber, or organic filed effect transistor, comprising the compound according to claim 1 .

22. A compound of formula

X 6 —Ar—Y—Ar′—X 6′   (X),

wherein

Y, Ar and Ar′ are defined in claim 1 , and

X 6 and X 6′ are independently of each other halogen, ZnX 12 , —SnR 207 R 208 R 209 , wherein R 207 , R 208 and R 209 are identical or different and are H or C 1 -C 6 alkyl, wherein two radicals optionally form a common ring and these radicals are optionally branched or unbranched and X 12 is a halogen atom; or —OS(O) 2 CF 3 , —OS(O) 2 -aryl, —OS(O) 2 CH 3 , —B(OH) 2 , —B(OY 1 ) 2 ,

 —BF 4 Na, or —BF 4 K,

wherein

Y 1 is independently in each occurrence a C 1 -C 10 alkyl group, Y 2 is independently in each occurrence a C 2 -C 10 alkylene group, which can optionally be substituted by one, or more C 1 -C 8 alkyl groups, and

Y 13 and Y 14 are independently of each other hydrogen, or a C 1 -C 10 alkyl group.

23. The compound according to claim 22 , which is a compound of formula

24. A process for producing a compound of formula

which process comprises

(a) reacting a compound of formula

with

a compound of formula T 1 COOH (XIIa) and a compound of formula T 2 COOH (XIIb), or

a compound of formula T 1 COOH (XIIa)

in a solvent in the presence of an acid and/or an acid anhydride,

wherein T 1 , T 2 , T 3 , T 4 , U 1 , U 2 , Ar, Ar′, R 10 and R 10′ are defined in claim 1 and when compound of formula (XI) is reacted only with a compound of formula (XIIa), T 2 in formula (Ia) has the meaning of T 1 .