Azide-based crosslinking agents

Patent metadata

Field	Value
Publication number	US-9847220-B2
Application number	US-201414903138-A
Country	US
Kind code	B2
Filing date	Jun 30, 2014
Priority date	Jul 8, 2013
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

The present invention provides compounds of formula

a process for their preparation, a solution comprising these compounds, a process for the preparation of a device using the solution, devices obtainable by the process and the use of the bis-azide-type compounds as cross-linkers.

First claim

The invention claimed is:

1. Compounds of formula

wherein
a is 0, 1 or 2,
b is 1, 2, 3 or 4,
c is 0 or 1,
d is 0, 1, 2, 3 or 4,
e is 0, 1 or 2,
x is 0, 1 or 2,
y is 0, 1 or 2,
z is 0, 1 or 2,
w is 0, 1 or 2,
n is 0 or 1,
Ar 1 and Ar 2 are independently from each other and at each occurrence, selected from an aromatic or heteroaromatic moiety, each of which is optionally substituted with one or more substituent R a selected from the group consisting of C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 12 membered heteroaryl, COOR 10 , CONR 10 R 11 , COR 10 , SO 3 R 10 , CN, NO 2 , halogen, OR 10 , SR 10 , NR 10 R 11 , OCOR 10 and NR 10 COR 11 ,
wherein R 10 and R 11 are independently from each other and at each occurrence, selected from H, C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl or 5 to 12 membered heteroaryl, and C 1-20 -alkyl and C 5-8 -cycloalkyl are each optionally substituted with one or more substituents R aa at each occurrence, R aa selected from the group consisting of phenyl, COOR 12 , CONR 12 R 13 , COR 12 , SO 3 R 12 , CN, NO 2 , halogen, OR 12 , SR 12 , NR 11 R 12 , OCOR 12 and NR 12 COR 13 , and C 6-14 -aryl and 5 to 12 membered heteroaryl are each optionally substituted with one or more substituent R ab at each occurrence, R ab selected from the group consisting of C 1-10 -alkyl, cyclopentyl, cyclohexyl, COOR 12 , CONR 12 R 13 , COR 12 , SO 3 R 12 , CN, NO 2 , halogen, OR 12 , SR 12 , NR 12 R 13 , OCOR 12 and NR 12 COR 13 , wherein R 12 and R 13 are independently from each other and at each occurrence, selected from C 1-10 -alkyl, cyclopentyl, cyclohexyl or phenyl, and

at least two adjacent Ar 1 , at least two adjacent Ar 2 , and/or Ar 1 and Ar 2 , both connected to L 2 or if c=0 to each other, can be additionally linked by one or more L a ,
wherein L a is a C 1-4 -alkylene that is optionally substituted with one or more C 1-10 -alkyl, and one or more CH 2 groups of C 1-4 -alkylene can be replaced by C═O, (C═O)O, (C═O)NR 60 , SO 2 —NR 60 , NR 60 , NR 60 R 61 , O or S,
wherein R 60 and R 61 are independently from each other and at each occurrence a C 1-10 -alkyl,

L 1 and L 3 are independently from each other and at each occurrence

 wherein
R 3 and R 4 are independently from each other and at each occurrence, selected from H, C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 12 membered heteroaryl, COOR 20 , CONR 20 R 21 , COR 20 , SO 3 R 20 , CN, NO 2 , or halogen,
wherein R 20 and R 21 are independently from each other and at each occurrence, selected from H, C 1-20 -alkyl and C 5-8 -cycloalkyl, C 6-14 -aryl or 5 to 12 membered heteroaryl, and C 1-20 -alkyl and C 5-8 -cycloalkyl are each optionally substituted with one or more substituents R b at each occurrence, R b selected from the group consisting of phenyl, COOR 22 , CONR 22 R 23 , COR 22 , SO 3 R 22 , CN, NO 2 , halogen, OR 22 , SR 22 , NR 22 R 23 , OCOR 22 and NR 22 COR 23 , and C 6-14 -aryl and 5 to 12 membered heteroaryl are each optionally substituted with one or more substituent R c at each occurrence, R c selected from the group consisting of C 1-10 -alkyl, cyclopentyl, cyclohexyl, COOR 22 , CONR 22 R 23 , COR 22 , SO 3 R 22 , CN, NO 2 , halogen, OR 22 , SR 22 , NR 22 R 23 , OCOR 22 and NR 22 COR 23 , wherein R 22 and R 23 are independently from each other and at each occurrence, selected from C 1-10 -alkyl, cyclopentyl, cyclohexyl or phenyl,
or, if L 1 or L 3 are

R 3 and R 4 together with the C-atoms to which they are attached form a 5 to 7-membered non-aromatic ring system A,
L 2 is a linking moiety selected from the group consisting of C 1-10 -alkylene, C 2-10 -alkenylene, C 5-8 -cycloalkylene, C 1-4 -alkylene-C 5-8 -cycloalkylene-C 1-4 -alkylene, C 1-4 -alkylene-phenylene-C 1-4 -alkylene, C 2-4 -alkenylene-C 5-8 -cycloalkylene-C 2-4 -alkenylene and C 2-4 -alkenylene-phenylene-C 2-4 -alkenylene, optionally substituted with one or more substituent R f at each occurrence selected from the group consisting of C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 12 membered heteroaryl, COOR 40 , CONR 40 R 41 , COR 40 , SO 3 R 40 , CN, NO 2 , halogen, OR 40 , SR 40 , NR 40 R 41 , OCOR 40 and NR 40 COR 41 ,
wherein R 40 and R 41 are independently from each other and at each occurrence H, C 1-10 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl or 5 to 12 membered heteroaryl, wherein C 1-20 -alkyl and C 5-8 -cycloalkyl are each optionally substituted with one or more substituents R fa at each occurrence, R fa selected from the group consisting of phenyl, COOR 42 , CONR 42 R 43 , COR 42 , SO 3 R 42 , CN, NO 2 , halogen, OR 42 , SR 42 NR 42 R 43 , OCOR 42 and NR 42 COR 43 ,
wherein C 6-14 -aryl and 5 to 12 membered heteroaryl are each optionally substituted with one or more substituent R fb at each occurrence, R fa selected from the group consisting of C 1-10 -alkyl, cyclopentyl, cyclohexyl, COOR 42 , CONR 42 R 43 , COR 42 , SO 3 R 42 , CN, NO 2 , halogen, OR 42 , NR 42 R 43 , OCOR 42 and NR 42 COR 43 ,
wherein R 42 and R 43 are independently from each other and at each occurrence selected from C 1-10 -alkyl, cyclopentyl, cyclohexyl or phenyl, and

wherein one or more CH 2 groups of C 1-10 -alkylene, C 1-4 -alkylene, C 2-10 -alkenylene, C 2-4 -alkenylene and/or C 5-8 -cycloalkylene can be replaced by C═O, (C═O)O, (C═O)NR 50 , SO 2 —NR 50 , NR 50 , NR 50 R 51 , O or S, wherein R 50 and R 51 are independently from each other and at each occurrence C 1-10 -alkyl, and

R 1 and R 2 are independently from each other and at each occurrence, selected from H, C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 12 membered heteroaryl, COOR 30 , CONR 30 R 31 , COR 30 , SO 3 R 30 , CN, NO 2 , halogen, OR 30 , SR 30 , NR 30 R 31 , OCOR 30 or NR 30 COR 31 ,
wherein R 30 and R 31 are independently from each other and at each occurrence, selected from H, C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl or 5 to 12 membered heteroaryl, and C 1-20 -alkyl and C 5-8 -cycloalkyl are each optionally substituted with one or more substituents R d at each occurrence, R d selected from the group consisting of phenyl, COOR 32 , CONR 32 R 33 , COR 32 , SO 3 R 32 , CN, NO 2 , halogen, OR 32 , SR 32 , NR 32 N 33 , OCOR 32 and NR 32 COR 33 , and C 6-14 -aryl and 5 to 12 membered heteroaryl are each optionally substituted with one or more substituent R e at each occurrence, R e selected from the group consisting of C 1-10 -alkyl, cyclopentyl, cyclohexyl, COOR 32 , CONR 32 R 33 , COR 32 , SO 3 R 32 , CN, NO 2 , halogen, OR 32 , SR 32 , NR 32 R 33 , OCOR 32 and NR 32 COR 33 ,
wherein R 32 and R 33 are independently from each other and at each occurrence, selected from C 1-10 -alkyl, cyclopentyl, cyclohexyl or phenyl.

2. Compounds of claim 1 , wherein n=0, and the compound of formula (1) is of formula

wherein R 1 , R 2 , x, y, z, w, L 1 , Ar 1 , L 2 , Ar 2 , L 3 , a, b, c, d and e are as depicted in claim 1 .

3. The compounds of claim 1 , wherein
Ar 1 and Ar 2 are independently from each other and at each occurrence, selected from an aromatic or heteroaromatic moiety, each of which is optionally substituted substituted with one or more substituent R a selected from the group consisting of C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 12 membered hete

Assignees

• Basf Se

Inventors

• Zhou Mi
• Brunetti Fulvio G
• Martin Emmanuel
• Becker Stefan
• Doi Iori
• Santoso Raissa Nathania
• Lam Mei Shan

Classifications

• H10P14/683 Primary

  carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC · CPC title

• C08J3/28

  Treatment by wave energy or particle radiation · CPC title

• H01L51/0545

  Electricity · mapped topic

• C08J2325/06

  Polystyrene · CPC title

• H01L51/052

  Electricity · mapped topic