Polymers based on fused diketopyrrolopyrroles

Patent metadata

Field	Value
Publication number	US-2016181534-A1
Application number	US-201414899757-A
Country	US
Kind code	A1
Filing date	Jun 19, 2014
Priority date	Jun 24, 2013
Publication date	Jun 23, 2016
Grant date	—

Abstract

The present invention relates to polymers comprising one or more (repeating) unit(s) of the formula (I), wherein Y is a group of formula (II); and their use as IR absorber, 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 according to the invention can have excellent solubility in organic solvents 10 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, organic photovoltaics and photodiodes.

First claim

1 . A polymer, comprising one or more (repeating) unit(s) of formula

wherein Y is of formula

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; and c′ is 0, 1, 2, or 3;
Ar and Ar′ denote a homo- or heteroaromatic system, which may be substituted, or unsubstituted;
R 1 , R 1′ , R 2 and R 2′ may be the same or different and are selected from hydrogen,
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, a silyl group, or a siloxanyl group; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 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, a silyl group, or a siloxanyl group; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 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, a silyl group, or a siloxanyl group; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 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, a silyl group, or a siloxanyl group; and/or can optionally be interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 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, a silyl group, or a siloxanyl group;
a C2-C20heteroaryl group which can optionally be substituted one or more times with C1-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, a silyl group, or a siloxanyl group;
a —CO—C 1 -C 18 alkyl group, a —CO—C 5 -C 12 cycloalkyl group, or —COO—C 1 -C 18 alkyl group; 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

such as, for example,

wherein
X is —O—, —S—, —NR 8 —, —Si(R 11 )(R 11′ )—, —Ge(R 11 )(R 11′ )—, —C(R 7 )(R 7 )—, —C(═O)—,

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)—,

R 3 and R 3′ are independently of each other hydrogen, halogen, halogenated C 1 -C 25 alkyl, CF 3 , cyano, C 1 -C 25 alkyl, C 3 -C 25 alkyl, which is optionally 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, especially CF 3 , cyano, C 1 -C 25 alkyl, especially C 3 -C 25 alkyl, which is optionally 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, C 3 -C 25 alkyl, which is optionally interrupted by one, or more oxygen, or sulphur atoms; or C 7 -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, especially C 3 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 11 and R 11′ are independently of each other C 1 -C 25 alkyl group, especially a C 1 -C 8 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, especially C 3 -C 25 alkyl, which is optionally interrupted by one, or more oxygen, or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or , wherein R 13 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group;
R 104 and R 104′ are independently of each other hydrogen, C 1 -C 18 alkyl, cyano, COOR 103 , C 6 -C 10 aryl, which may optionally be substituted by G, or C 2 -C 8 heteroaryl, which is optionally substituted by G,
R 103 and R 103′ are independently of each other C 1 -C 100 alkyl, especially C 3 -C 25 alkyl, C 1 -C 25 alkyl 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, or C 2 -C 20 heteroaryl which is 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 is optionally 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; C 3 -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 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

Assignees

• Basf Se

Inventors

• Hayoz Pascal
• Grzybowski Marek
• Gryko Daniel T
• Jezewski Artur

Classifications

• C08G2261/92

  TFT applications · CPC title

• C08G2261/414

  Stille reactions · CPC title

• C08G2261/1424

  containing ether groups, including alkoxy · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C08G2261/3327

  alkene-based · CPC title