Polymers based on naphthodiones

Patent metadata

Field	Value
Publication number	US-9748487-B2
Application number	US-201314435619-A
Country	US
Kind code	B2
Filing date	Nov 5, 2013
Priority date	Nov 7, 2012
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

The present invention relates to polymers comprising one or more (repeating) unit(s) of the formula (I), and compounds of formula (III), wherein Y, Y 15 , Y 16 and Y 17 are independently of each other a group of formula 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 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.

First claim

The invention claimed is:

1. A polymer, comprising a unit of formula (I):

wherein
Y is a group of formula

a is 1, 2, or 3;
a′ is 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;
U 1 is O, S, or NR 1 ;
U 2 is O, S, or NR 2 ;
T 1 , T 2 , T 3 and T 4 are independently hydrogen, halogen, hydroxyl, 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 , C 1 -C 25 alkyl, which is optionally substituted by E and/or interrupted by D, C 5 -C 12 cycloalkyl, which is optionally substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy; 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 1 and R 2 are independently selected from the group consisting of hydrogen, a C 1 -C 100 alkyl group which is optionally 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 is optionally interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 CO—, —COO—, —CO— or —OCO—,
a C 2 -C 100 alkenyl group which is optionally 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 is optionally interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 CO—, —COO—, —CO— or —OCO—,
a C 3 -C 100 alkinyl group which is optionally 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 is optionally interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 CO—, —COO—, —CO— or —OCO—,
a C 3 -C 12 cycloalkyl group which is optionally 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 is optionally interrupted by —O—, —S—, —NR 39 —, CONR 39 —, NR 39 CO—, —COO—, —CO— or —OCO—,
a C 6 -C 24 aryl group which is optionally 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 C 2 -C 20 heteroaryl group which is optionally 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 —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

 such as, for example,

 which optionally is

 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′ )—,

 which optionally is

 which optionally is

 wherein
X 1 is S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 106 )(R 109 )—, —C(═O)—, —C(═CR 104 R 104′ )—,

R 3 and R 3′ are independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, 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 25 alkoxy;
R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, 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 25 alkoxy;
R 7 , R 7′ , R 9 and R 9′ are independently hydrogen, C 1 -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 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 is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 11 and R 11′ are independently C 1 -C 25 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which is optionally 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 hydrogen, halogen, cyano, C 1 -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 103 and R 103′ are independently C 1 -C 100 alkyl, C 1 -C 25 alkyl 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 hydrogen, C 1 -C 18 alkyl, cyano, COOR 103 , C 6 -C 10 aryl, which is optionally substituted by G, or C 2 -C 8 heteroaryl, which is optionally substituted by G,
R 105 , R 105′ , R 106 and R 106′ are independently 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; which is optionally interrupted by —O—, or —S—; or —COOR 103 ;
R 108 and R 109 are independently 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

Assignees

• Basf Se

Inventors

• Hayoz Pascal
• Tieke Bernd
• Zhang Haichang

Classifications

• C08G2261/59

  Stability · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08G61/125

  with a five-membered ring containing one oxygen atom in the ring · CPC title

• H01L51/0043

  Electricity · mapped topic

• H01L51/0035 Primary

  Electricity · mapped topic