Preparation of polymers comprising at least one benzo[c][1,2,5]thiadiazol-5,6-dicarbonitrile-unit

Patent metadata

Field	Value
Publication number	US-10059797-B2
Application number	US-201515528897-A
Country	US
Kind code	B2
Filing date	Nov 23, 2015
Priority date	Nov 24, 2014
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

A polymer containing at least one unit of formula

is prepared by treating a compound of formula

wherein Y 2 is I, Br, Cl or O—S(O) 2 CF 3 ,

with an S-donor agent, in order to obtain the compound of formula

wherein Y 2 is as defined for the compound of formula (5).

First claim

The invention claimed is:

1. A process for the preparation of a polymer comprising at least one unit of formula

wherein
Ar 1 and Ar 2 are independently from each other and at each occurrence C 6-14 -arylene or a 5 to 15 membered heteroarylene,
wherein Ar 1 and Ar 2 can be substituted with one to four substituents selected from the group consisting of C 1-30 -alkyl, CN and C 6-14 -aryl, and
wherein at least two adjacent Ar 1 , respectively, at least two adjacent Ar 2 can be connected via an -(L) m - linker,
wherein L is at each occurrence selected from the group consisting of CR 1 R 2 , C═CR 1 R 2 , C═O and SiR 1 R 2 , wherein R 1 and R 2 are individually from each other and at each occurrence H or C 1-20 -alkyl, and m is 1 or 2,
o is an integer from 1 to 8, and
n is an integer from 1 to 8,
said process comprising
(i) treating a compound of formula

wherein
Y 2 is I, Br, Cl or O—S(O) 2 CF 3 ,
with an S-donor agent, in order to obtain the compound of formula

wherein Y 2 is as defined for the compound of formula (5).

2. The process of claim 1 , wherein in the polymer comprising at least one unit of formula (1)
Ar 1 and Ar 2 are independently from each other and at each occurrence C 6-10 -arylene or a 5 to 9 membered heteroarylene,
wherein Ar 1 and Ar 2 can be substituted with one to four substituents selected from the group consisting of C 1-30 -alkyl, CN and C 6-14 -aryl, and
wherein at least two adjacent Ar 1 , respectively, at least two adjacent Ar 2 can be connected via an -(L) m - linker,
wherein L is at each occurrence selected from the group consisting of CR 1 R 2 , C═CR 1 R 2 , C═O and SiR 1 R 2 , wherein R 1 and R 2 are individually from each other and at each occurrence H or C 1-20 -alkyl, and m is 1 or 2.

3. The process of claim 2 , wherein in the polymer comprising at least one unit of formula (1)
Ar 1 and Ar 2 are independently from each other and at each occurrence a 5 to 9 membered heteroarylene,
wherein Ar 1 and Ar 2 can be substituted with one to four substituents selected from the group consisting of C 1-30 -alkyl, CN and C 6-14 -aryl, and
wherein at least two adjacent Ar 1 , respectively, at least two adjacent Ar 2 can be connected via an -(L) m - linker,
wherein L is at each occurrence selected from the group consisting of CR 1 R 2 , C═CR 1 R 2 , C═O and SiR 1 R 2 , wherein R 1 and R 2 are individually from each other and at each occurrence H or C 1-20 -alkyl, and m is 1 or 2.

4. The process of claim 3 , wherein in the polymer comprising at least one unit of formula (1)
Ar 1 and Ar 2 are independently from each other and at each occurrence a 5 membered heteroarylene,
wherein Ar 1 and Ar 2 can be substituted with one to four substituents selected from the group consisting of C 1-30 -alkyl, CN and C 6-14 -aryl.

5. The process of claim 4 , wherein in the polymer comprising at least one unit of formula (1)
o is an integer from 1 to 6, and
n is an integer from 1 to 6.

6. The process of claim 5 , wherein in the polymer comprising at least one unit of formula (1)
o is an integer from 1 to 4, and
n is an integer from 1 to 4.

7. The process of claim 1 , further comprising
(ii) treating the compound of formula (4) as obtained in step (i)
with a compound of formula

wherein
Ar 1 and o are as defined for the polymer comprising at least one unit of formula (1), and
Z b is selected from the group consisting of B(OZ 1 )(OZ 2 ), SnZ 1 Z 2 Z 3 ,

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are independently from each other and at each occurrence H or C 1-6 -alkyl,
in the presence of catalyst II,
in order to obtain a compound of formula

wherein
Ar 1 and o are as defined for the polymer comprising at least one unit of formula (1), and
(iii) treating a compound of formula (3) as obtained in step (ii) with a Y 1 -donor agent, wherein Y 1 is I, Br, Cl or O—S(O) 2 CF 3 , in order to obtain the compound of formula

wherein
Ar 1 and o are as defined for the polymer comprising at least one unit of formula (1), and
Y 1 is at each occurrence I, Br, Cl or O—S(O) 2 CF 3 ,
(iv) treating a compound of formula (2) as obtained in step (iii) with a compound of formula

wherein
Ar 2 and n are as defined for the polymer comprising at least one unit of formula (1), and
Z a is at each occurrence selected from the group consisting of B(OZ 1 )(OZ 2 ), SnZ 1 Z 2 Z 3 ,

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are independently from each other and at each occurrence H or C 1-6 -alkyl,
in the presence of catalyst I,
in order to obtain the polymer comprising at least one unit of formula (1).

8. A process for the preparation of a compound of

wherein Y 2 is I, Br, Cl or O—S(O) 2 CF 3 ,
said process comprising
treating a compound of formula

wherein
Y 2 is as defined for the compound of formula (4)
with an S-donor agent.

9. The compound of

wherein Y 2 is I, Br, Cl or O—S(O) 2 CF 3 .

Assignees

• Basf Se
• Max Planck Gesellschaft

Inventors

• Gessner Thomas
• Reichelt Helmut
• Wudarczyk Jakob Jacek
• Hinkel Felix Peter
• Marszalek Tomasz
• Baumgarten Martin
• Muellen Klaus

Classifications

• C08G2261/92

  TFT applications · CPC title

• C08G2261/143

  Side-chains containing nitrogen · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title

• H01L51/0043

  Electricity · mapped topic

• H01L51/0036

  Electricity · mapped topic