Ether-based polymers as photo-crosslinkable dielectrics

Patent metadata

Field	Value
Publication number	US-10020456-B2
Application number	US-201515514180-A
Country	US
Kind code	B2
Filing date	Aug 13, 2015
Priority date	Sep 25, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

Polymers comprising at least one unit of formula (1) wherein n is 0 or 1, m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6, provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time, Ar 1 and Ar 2 are independently from each other C 6-14 -arylene or C 6-14 -aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl and 5 to 14 membered heteroaryl, and X 1 , X 2 and X 3 are independently from each other and at each occurrence O or S, compositions comprising these polymers, and electronic devices comprising a layer formed from the compositions. Preferably, the electronic device is an organic field effect transistor and the layer is the dielectric layer.

First claim

The invention claimed is:

1. A polymer, comprising:
at least one unit of formula (1):

wherein:
n is 0 or 1;
m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6,
provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time;
Ar 1 and Ar 2 are independently from each other a C 6-14 -arylene or a C 6-14 -aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;
X 1 , X 2 and X 3 are independently from each other and at each occurrence O or S;
R 1 and R 2 are independently from each other and at each occurrence selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;
C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl;
C 5-8 -cycloalkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, a C 1-10 -alkyl, CN, a C 2-10 -alkenyl, a C 2-10 -alkynyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and
C 6-14 -aryl and 5 to 14 membered heteroaryl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6 -cycloalkyl.

2. The polymer of claim 1 , wherein:
n is 0 or 1; and
m and p are independently from each other 0, 1, 2, 3 or 4,
provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time.

3. The polymer of claim 1 , wherein:
n is 0 or 1; and
m and p are independently from each other 0, 1, 2, 3 or 4,
provided that the sum of n and p is at least 2.

4. The polymer of claim 1 , wherein:
n is 0 or 1; and
m and p are independently from each other 0, 1, 2, 3 or 4,
provided that the sum of n and p is at least 3.

5. The polymer of claim 1 , wherein:
Ar 1 and Ar 2 are independently from each other a phenylene or phenyl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;
C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl, and a 5 to 10 membered heteroaryl;
C 5-8 -cycloalkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and
C 6-14 -aryl and 5 to 14 membered heteroaryl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6- cycloalkyl.

6. The polymer of claim 1 , wherein:
Ar 1 and Ar 2 are independently from each other a phenylene or phenyl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-20 -alkyl, a C 2-20 -alkenyl and a C 2-20 -alkynyl; and
C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl.

7. The polymer of claim 1 , wherein Ar 1 and Ar 2 are independently from each other an unsubstituted phenylene or phenyl.

8. The polymer of claim 1 , wherein:
at least one of n, m and p is not 0, and
X 1 , X 2 and X 3 are 0.

9. The polymer of claim 1 , wherein:
R 1 and R 2 are independently from each other and at each occurrence selected from the group consisting of a C 1-20 -alkyl, a C 2-20 -alkenyl, a C 2-20 -alkynyl and phenyl;
C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and
phenyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6 -cycloalkyl.

10. The polymer of claim 1 , wherein:
R 1 and R 2 are independently from each other and at each occurrence selected from the group consisting of a C 1-10 -alkyl and phenyl;
C 1-10 -alkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen and phenyl; and
phenyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen and C 1-6 -alkyl.

11. The polymer of claim 1 , wherein:
at least one of m and p is not 0;
R 1 and R 2 area C 1-6 -alkyl; and
C 1-6 -alkyl can be substituted with 1 to 3 of a halogen.

12. The polymer of claim 1 , which is a copolymer comprising:
at least one unit of formula (1):

and at least one unit of formula (10):

wherein:
n is 0 or 1;
m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6,
provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time;
q is 0, 1, 2, 3, 4, 5 or 6;
Ar 1 , Ar 2 and Ar 3 are independently from each other a C 6-14 -arylene or a C 6-14 -aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;
X 1 , X 2 , X 3 , and X 4 are independently from each other and at each occurrence O or S;
R 1 , R 2 and R 3 are independently from each other and at each occurrence selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;
C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl;
C 5-8 -cycloalkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and
C 6-14 -aryl and 5 to 14 membered heteroaryl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6 -cycloalkyl.

13. A composition, comprising:
the polymer of claim 1 and a solvent.

14. The composition of claim 13 , further comprising:
a crosslinker.

15. A process for preparing an electronic device containing a layer formed from

Assignees

• Basf Se

Inventors

• Martin Emmanuel
• Brunetti Fulvio G
• Zhou Mi
• Becker Stefan
• Kaelblein Daniel
• Wu Chao
• Praptana Raimond
• Knoll Konrad
• Kopping Jordan Thomas

Classifications

• C08F212/32

  containing two or more rings · CPC title

• C08F212/22

  Oxygen · CPC title

• C08F112/32

  containing two or more rings · CPC title

• C08F112/22

  Oxygen · CPC title

• C09D125/18 Primary

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title