Azide-based crosslinking agents

Patent metadata

Field	Value
Publication number	US-2016155633-A1
Application number	US-201414903138-A
Country	US
Kind code	A1
Filing date	Jun 30, 2014
Priority date	Jul 8, 2013
Publication date	Jun 2, 2016
Grant date	—

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

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 an aromatic or heteroaromatic moiety, which can be 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 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 can be substituted with one or more substituents R aa at each occurrence 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 can be substituted with one or more substituent R ab at each occurrence 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 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 linking moiety B,

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 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 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 can be substituted with one or more substituents R b at each occurrence 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 33 , and C 6-14 -aryl and 5 to 12 membered heteroaryl can be substituted with one or more substituent R c at each occurrence 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 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 A, and
R 1 and R 2 are independently from each other and at each occurrence 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 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 can be substituted with one or more substituents R d at each occurrence 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 R 33 , OCOR 32 and NR 32 COR 33 , and C 6-14 -aryl and 5 to 12 membered heteroaryl can be substituted with one or more substituent R e at each occurrence 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 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 17 .

3 . The compounds of claim 1 , wherein
Ar 1 and Ar 2 are independently from each other and at each occurrence an aromatic or heteroaromatic moiety, which can be 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 H, C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl or 5 to 12 membered heteroaryl, 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 linking moiety B, and
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 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 H, C 1-20 -alkyl, C 5-8 -cycloalkyl, C 6-14 -aryl or 5 to 12 membered heteroaryl,

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.

4 . The compounds of claim 1 , wherein
L 2 is a linking moiety A, wherein the linking moiety A is 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, which can be 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, and C 1-20 -alkyl and C 5-8 -cycloalkyl can be substituted with one or more substituents R fa at each occurrence 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

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

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• C07D333/20 Primary

  by nitrogen atoms (nitro, nitroso radicals C07D333/12) · CPC title

• C08K5/28

  Azides · CPC title

• C08K5/45

  Heterocyclic compounds having sulfur in the ring · CPC title