Semiconducting polymers

Patent metadata

Field	Value
Publication number	US-10155774-B2
Application number	US-201514829698-A
Country	US
Kind code	B2
Filing date	Aug 19, 2015
Priority date	Feb 15, 2010
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

The invention relates to novel polymers containing repeating units based on benzodithiophene or derivatives thereof, monomers and methods for their preparation, their use as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers.

First claim

The invention claimed is:

1. Monomer of formula Ia
R 2 -A-R 3   Ia

wherein
A is a unit of formula I

wherein
one of X 1 and X 2 is selected from S, Se and O, and the other is selected from CH, CR x , and N,
one of X 3 and X 4 is selected from S, Se and O, and the other is selected from CH, CR x , and N,

R on each occurrence identically or differently denotes
primary alkyl with 1 to 30 C atoms, wherein one or more H atoms are optionally replaced by F;
secondary alkyl with 3 to 30 C atoms, wherein one or more H atoms are optionally replaced by F;
tertiary alkyl with 4 to 30 C atoms, wherein one or more H atoms are optionally replaced by F;
—CO—R y ;
—CO—O—R y or
—O—CO—R y ,

R y is straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —CR 0 ═CR 00 — or —C≡C— and in which one or more H atoms are optionally replaced by F,
or
aryl or hetaryl having 2 to 30 C atoms that is unsubstituted or substituted by one or more non-aromatic groups R 1 ,

R x is on each occurrence identically or differently straight-chain, branched or cyclic alkyl with 1 to 15 C atoms, in which one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—O—, —CR 0 ═CR 00 — or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN,
R 0 and R 00 are independently of each other H or optionally substituted carbyl or hydrocarbyl optionally comprising one or more hetero atoms, and
R 2 and R 3 independently of each other denote Cl, Br, I, —B(OZ 2 ) 2 , —CZ 3 ═C(Z 4 ) 2 or Sn(Z 4 ) 3 , wherein Z 2-4 are selected from the group consisting of alkyl and aryl, each being optionally substituted, and two Z 2 groups may also form a cyclic group
R 1 is on each occurrence identically or differently H, halogen, —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 , optionally substituted silyl, carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms,
X 0 is halogen.

2. A monomer according to claim 1 , wherein in the unit of formula I, X 1 and X 3 are S, and X 2 and X 4 are CH.

3. A monomer according to claim 1 wherein R or R y on each occurrence identically or differently denotes
primary alkyl with 1 to 30 C atoms, wherein one or more H atoms are optionally replaced by F;
secondary alkyl with 3 to 30 C atoms, wherein one or more H atoms are optionally replaced by F; or
tertiary alkyl with 4 to 30 C atoms, wherein one or more H atoms are optionally replaced by F.

4. A monomer according to claim 1 wherein R on each occurrence identically or differently denotes
—CO—R y ;
—CO—O—R y or
—O—CO—R y
and R y on each occurrence identically or differently denotes primary alkyl with 1 to 30 C atoms, wherein one or more H atoms are optionally replaced by F;
secondary alkyl with 3 to 30 C atoms, wherein one or more H atoms are optionally replaced by F; or
tertiary alkyl with 4 to 30 C atoms, wherein one or more H atoms are optionally replaced by F.

Assignees

• Merck Patent Gmbh

Inventors

• Mitchell William
• Tierney Steven
• Wang Changsheng
• Blouin Nicolas

Classifications

• C09K19/3497

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• C09K19/3477

  the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom · CPC title

• C09K19/3491

  having sulfur as hetero atom · CPC title

• C09K19/38

  Polymers · CPC title