DIKETOPYRROLOPYRROLE POLYMERS FOR USE IN ORGANIC FIELD EFFECT TRANSISTORS
The present invention relates to polymers comprising a repeating unit of the formula I, or III and their use as organic semiconductor in organic devices, especially an organic field effect transistor (OFET), or a device containing a diode and/or an organic field effect transistor. The polymers according to the invention 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 according to the invention are used in organic field effect transistors.
1 .- 16 . (canceled)
17 . A copolymer comprising repeating units of formula (VII)
wherein
A is a group of formula
COM 1 is a group of formula
a is an integer of 1 to 5,
n is number which results in a molecular weight of 4,000 to 2,000,000 Daltons,
Ar 1 and Ar 1′ are a group of formula
Ar 2 is a group of formula
one of X 1 and X 2 is N and the other is CH, and
R 1 and R 2 are the same or different and are selected from H or a C 1 -C 100 alkyl group.
18 . The copolymer according to claim 17 , wherein a is an integer of 1 to 3.
19 . The copolymer according to claim 17 , wherein R 1 and R 2 are a C 1 -C 100 alkyl group.
20 . The copolymer according to claim 19 , wherein R 1 and R 2 are a C 8 -C 36 alkyl group.
21 . The copolymer according to claim 17 , wherein Ar 2 is a group of formula
22 . A copolymer comprising repeating units of formula (IIa′) or (IIi)
wherein
R 1 and R 2 are the same or different and are selected from a C 8 -C 36 alkyl group.
23 . The copolymer according to claim 17 , which has a weight average molecular weight of 10,000 to 1,000,000 Daltons.
24 . The copolymer according to claim 23 , which has a weight average molecular weight of 10,000 to 100,000 Daltons.
25 . A semiconductor device comprising the copolymer according to claim 17 .
26 . The semiconductor device according to claim 25 is an organic field effect transistor.
27 . A process for preparing an organic semiconductor device, the process comprising:
applying a solution and/or dispersion comprising the copolymer according to claim 17 in an organic solvent to a substrate; and
removing the solvent.
28 . An integrated circuit comprising the organic field effect transistor according to claim 26 .
29 . A process for preparing the copolymer of claim 17 comprising:
reacting a dihalogenide X 10 -A-X 10 with an equimolar amount of a diboronic acid or diboronate corresponding to formula
or
reacting a dihalogenide of formula
with an equimolar amount of a diboronic acid or diboronate corresponding to formula X 11 -A-X 11 ,
wherein X 10 is halogen, and
X 11 is independently in each occurrence —B(OH) 2 , —B(OY 1 ) 2 ,
—BF 3 Na, —BF 3 N(Y 15 ) 4 , or —BF 3 K, wherein Y 1 is independently in each occurrence a C 1 -C 10 alkyl group and Y 2 is independently in each occurrence a C 2 -C 10 alkylene group, Y 13 and Y 14 are independently of each other hydrogen, or a C 1 -C 10 alkyl group, Y 15 is H, or a C 1 -C 25 alkyl group, which may optionally be interrupted by —O—, in a solvent and in the presence of a catalyst; or
reacting a dihalogenide of formula X 10 -A-X 10 with an equimolar amount of an organo tin compound corresponding to formula or
or
reacting a dihalogenide of formula
with an equimolar amount of an organo tin compound corresponding to formula X 11′ -A-X 11′ , wherein
X 11′ is independently in each occurrence —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, or two of the groups R 207 R 208 and R 209 form a ring and these groups are optionally branched.
30 . The process according to claim 29 , wherein X 10 is Br.