Polymers and oligomers with functionalized side groups

Patent metadata

Field	Value
Publication number	US-9246103-B2
Application number	US-201214234825-A
Country	US
Kind code	B2
Filing date	Jun 28, 2012
Priority date	Jul 25, 2011
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

Abstract

The present invention relates inter alia to oligomers and/or polymers with functionalized side groups which are bound to the backbone of the polymer via spacer.

First claim

The invention claimed is:

1. A conjugated oligomer or polymer comprising at least one unit of Formula (192)

where A is a spacer that is not N-substituted;
A e is an electron transporting group,
A h is an hole transporting group,
A em is an emissive group,
B is a backbone group,
0<n1<1,
0<n2<1,
0<n3<1 and
0≦n4<1.

2. The oligomer or polymer according to claim 1 , wherein the difference between the LUMOs of the said A e and the main chain is less than 0.2 eV.

3. The oligomer or polymer according to claim 1 , wherein the difference between the LUMOs of the said A h and the main chain isles than 0.2 eV.

4. The oligomer or polymer according to claim 1 , wherein the HOMO of the said B is at least 0.3 eV higher that of the main chain.

5. The oligomer or polymer according to claim 1 , wherein A is saturated unsubstituted or substituted alkyl, alkylsilyl, silyl, alkyloxyalkyl or alkylthioalkyl with 1 to 12 C atoms, wherein the substitution pattern is hydrogen, halogen, alkyl, heteroalkyl or cycloalkyl.

6. The oligomer or polymer according to claim 1 , wherein there are at least two adjacent single bonds along the main chain of A.

7. The oligomer or polymer according to claim 1 , wherein A is fluorinated, linear or branched alkylene or alkyleneoxy with 1 to 12 C atoms.

8. The oligomer or polymer according to claim 1 , wherein A e is selected from one of the following electron transporting groups: imidazoles, pyridines, pyrimidines, pyridazines, pyrazines, chinolines, chinoxalines, anthracenes, benzanthracenes, pyrenes, perylenes, benzimidazoles, triazines, ketones, phosphinoxides, phenazines, phenanthrolines, triarylboranes, phenanthrenes, fluorenes, indenofluorenes, isomers and derivatives thereof.

9. The oligomer or polymer according to claim 1 , wherein A h is selected from amines, triarylamines, thiophenes, carbazoles, indolocarbazoles, phthalocyanines, porphyrines, isomers and derivatives thereof.

10. The oligomer or polymer according to claim 1 , wherein B is selected from identical or different groups of Formula (6)

wherein
D, E and E′ are independently of each other, and in case of multiple occurrence independently of one another, a divalent group, selected from —CR 1 R 2 —, —NR 1 —, —PR 1 —, —O—, —S—, —SO—, —SO 2 —, —CO—, —CS—, —CSe—, —P(═S)R 1 — and —SiR 1 R 2 —,
R 1 and R 2 are independently of each other identical or different groups selected from H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —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, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, and optionally the groups R 1 and R 2 form a Spiro group with the fluorene moiety to which they are attached,
X is halogen,
R 0 and R 00 are independently of each other hydrogen, a substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
each g is independently 0 or 1 and each corresponding h in the same subunit is the opposite of 0 and 1,
m is an integer larger than or equal to 1,
Ar 4 and Ar 5 are independently of each other mono- or polynuclear aryl or heteroaryl that is unsubstituted or substituted and optionally fused to the 7,8-positions or 8,9-positions of the indenofluorene group,
a and b are independently of each other 0 or 1.

11. The oligomer or polymer according to claim 1 , wherein A h is selected from one or more identical or different groups of Formula (47)

wherein
Y is N, P, B, P═O, PF 2 , P═S, As, As═O, As═S, Sb, Sb═O or Sb═S, Si—R 1 , Ge—R 1 ,
R 1 is H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X, —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, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, and optionally the groups R 1 and R 2 form a spiro group with the fluorene moiety to which they are attached,
X is halogen,
R 0 and R 00 are independently of each other hydrogen, a substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
Ar 11 which may be the same or different, denote, independently if in different repeat units, a single bond or an optionally substituted mononuclear or polynuclear aryl group,
Ar 12 which may be the same or different, denote, independently if in different repeat units, an optionally substituted mononuclear or polynuclear aryl group,
Ar 13 which may be the same or different, denote, independently if in different repeat units, an optionally substituted mononuclear or polynuclear aryl group, which may be optionally substituted by a bridging group linking different chain residues of formula II, and
m is 1, 2 or 3.

12. The oligomer or polymer according to claim 1 , wherein B is selected from one or more identical or different groups of Formula (18)

wherein
R 1 and R 2 are independently of each other identical or different groups selected from H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —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, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, and optionally the groups R 1 and R 2 form a spiro group with the fluorene moiety to which they are attached,
X is halogen,
R 0 and R 00 are independently of each other hydrogen, a substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
X 1 and X 2 are independently of each other —CR 1 ═CR 1 —, —C≡C— or —N—Ar 8 —,
Ar 6-8 are in case of multiple occurrence independently of one another a bivalent aromatic or heteroaromatic ring system having from 2 to 40 C atoms, which is optionally substituted by one or more groups R 1 ,
g is in each occurrence independently of one another 0 or 1, and
h is in each occurrence independently of one another 0, 1 or 2.

13. The oligomer or polymer according to claim 1 , wherein B is selected from one or more identical or different groups of Formula (24):

wherein X 1 and X 2 are independently of each other —CR 1 ═CR 1 —, —C≡C— or —N—Ar 8 —,
Ar 6-7 are in case of multiple occurrence independently of one another a bivalent aromatic or heteroaromatic ring system having from 2 to 40 C atoms, which is optionally substituted by one or more groups R 1 ,
g is in each occurrence independently of one another 0 or 1, and
h is in each occurrence independently of one another 0, 1 or 2
X is in each occurrence independently of one another CH, CR 1 or N,
Z is in each occurrence independently of one another a single bond, CR

Assignees

• Pan Junyou
• Meyer Frank Egon
• Schulte Niels
• Scheurich René Peter
• Merck Patent Gmbh

Inventors

• Pan Junyou
• Meyer Frank Egon
• Schulte Niels
• Scheurich René Peter

Classifications

• H01L51/5012

  Electricity · mapped topic

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0039

  Electricity · mapped topic

• H01L51/0043 Primary

  Electricity · mapped topic

• H01L51/0035

  Electricity · mapped topic