Polycyclic polymer comprising thiophene units, a method of producing and uses of such polymer

Patent metadata

Field	Value
Publication number	US-10134994-B2
Application number	US-201415100360-A
Country	US
Kind code	B2
Filing date	Oct 29, 2014
Priority date	Nov 28, 2013
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

The present invention relates to a novel polycyclic polymer comprising fused thiophene units. The present invention also relates to a method for producing such polymer as well as the use of such polymer, particularly in organoelectronic applications.

First claim

The invention claimed is:

1. Compound comprising a divalent unit selected from the group consisting of units of the following formula (I)

wherein R 1 and R 2 are independently of each other selected from the group consisting of H, halogen, carbyl and hydrocarbyl, and X is at each occurrence independently selected from the group consisting of CR 3 R 4 , SiR 3 R 4 , GeR 3 R 4 and C═CR 3 R 4 , with R 3 and R 4 being independently of each other selected from the group consisting of hydrogen, carbyl and hydrocarbyl.

2. Compound according to claim 1 , wherein X is CR 3 R 4 or SiR 3 R 4 .

3. Compound according to claim 1 , wherein X is CR 3 R 4 .

4. Compound according to claim 1 comprising a divalent unit of the following formulae (Ia)

wherein Ar comprises an aromatic ring system comprising from 6 to 60 aromatic carbon atoms or a heteroaromatic ring system comprising from 5 to 60 aromatic ring atoms, at least one of which is a heteroatom.

5. Compound according to claim 4 , wherein Ar is selected from the group consisting of formulae (D1) to (132) and (A1) to (A93):

wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are independently of each other selected from the group consisting of hydrogen, F, Br, Cl, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(O)NR 0 R 00 , —C(O)X 0 , —C(O)R 0 , —NH 2 , —NR 0 R 00 , —SH, —SR 0 , —SO 3 H, —SO 2 R 0 , —OH, —NO 2 , —CF 3 , —SF 5 , and optionally substituted silyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, where X 0 is halogen and R 0 and R 00 are, independently of each other, H or optionally substituted C 1-40 carbyl or hydrocarbyl.

6. Compound according to claim 5 , wherein Ar is selected from the group consisting of formulae (D1), (D10), (D19), (A1) and (A19), wherein R 11 and R 12 are independently of each other hydrogen or fluorine.

7. Compound according to claim 1 comprising a group M, which comprises the following structure:
*—U a m1 —Ar a m2 —U b m3 —Ar b m4 —Ar c m5 —*  (III)

wherein
U a and U b are independently of each other selected from the divalent unit selected from the group consisting of formulae (I) of claim 1 ;
Ar a , Ar b and Ar c are independently of each other aryl or heteroaryl different from U a and U b ;
m1, m2, m3 and m4 are independently of each other selected from the group consisting of 0, 1 and 2, with the provision that at least one of m1 and m3 is not 0; and
m5 is 0 or an integer from 1 to 10.

8. Compound according to claim 7 , wherein Ar a , Ar b and Ar c —if present—are independently of each other selected from the group consisting of formulae (D1) to (D132) and (A1) to (A93):

wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are independently of each other selected from the group consisting of hydrogen, F, Br, Cl, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(O)NR 0 R 00 , —C(O)X 0 , —C(O)R 0 , —NH 2 , —NR 0 R 00 , —SH, —SR 0 , —SO 3 H, —SO 2 R 0 , —OH, —NO 2 , —CF 3 , —SF 5 , and optionally substituted silyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, where X 0 is halogen and R 0 and R 00 are, independently of each other, H or optionally substituted C 1-40 carbyl or hydrocarbyl.

9. Compound according to claim 8 , wherein Ar a , Ar b and Ar c —if present—are independently of each other selected from the group consisting of formulae (D1), (D10), (D19), (A1) and (A19), wherein R 11 and R 12 are independently of each other hydrogen or fluorine.

10. Compound according to claim 1 , wherein the compound is selected from the group consisting of small molecule, monomer, oligomer and polymer.

11. A mixture or a blend comprising one or more compounds of claim 1 and

Assignees

• Merck Patent Gmbh

Inventors

• Mitchell William
• D'Lavari Mansoor
• Wang Changsheng
• Sparrowe David

Classifications

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title

• C08G2261/414

  Stille reactions · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C08G2261/411

  Suzuki reactions · CPC title