Charge transporting semi-conducting material and semi-conducting device

Patent metadata

Field	Value
Publication number	US-11322687-B2
Application number	US-201314426698-A
Country	US
Kind code	B2
Filing date	Sep 6, 2013
Priority date	Sep 7, 2012
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

The present invention relates to a charge transporting semi-conducting material comprising: a) optionally at least one electrical dopant, and b) at least one cross-linked charge-transporting polymer comprising 1,2,3-triazole cross-linking units, a method for its preparation and a semiconducting device comprising the charge transporting semi-conducting material.

First claim

The invention claimed is:

1. A charge transporting semi-conducting material comprising:
a cross-linked charge-transporting polymer comprising 1,2,3-triazole cross-linking units of the general formulae Ia and/or Ib,

wherein
aa) Pol 1 -Pol 4 are independently selected from charge-transporting polymers,
bb) X 1 , X 2 , X 3 , and X 4 are independently selected from spacer units having up to 30 multivalent atoms or represent direct bonding of Pol 1 -Pol 4 to the 1,2,3-triazole ring, and
cc) R and R′ are independently selected from the group consisting of

H, halogen, nitrile, C 1 -C 22 saturated or unsaturated alkyl, C 3 -C 22 cycloalkyl, C 6 -C 18 aryl, C 7 -C 22 arylalkyl,
C 2 -C 13 heteroaryl having up to three heteroatoms independently selected from oxygen, nitrogen, or sulphur,
SiR 1 R 2 R 3 , wherein R 1 , R 2 , and R 3 are independently selected from C 1 -C 4 alkyl or phenyl, COR 4 or COOR 5 , wherein R 4 and R 5 are independently selected from C 1 -C 22 alkyl or C 7 -C 22 arylalkyl, and
CR 6 R 7 OR 8 , wherein R 6 and R 7 are independently selected from H, C 1 -C 6 alkyl, C 6 -C 9 aryl, or R 6 and R 7 together form a C 3 -C 7 ring, and R 8 is C 1 -C 6 alkyl, C 7 -C 22 arylalkyl, SiR 9 R 10 R 11 , wherein R 9 , R 10 , and R 11 are independently selected from C 1 -C 4 alkyl or phenyl, or COR 12 , wherein R 12 is H or C 1 -C 21 alkyl; and
wherein

(i) the cross-linked charge-transporting polymer is a continuous infinite network,
(ii) the charge-transporting polymer is capable of transporting an injected charge due to a system of overlapping orbitals along the charge-transporting polymer, and
(iii) the injected charge is an electron injected or withdrawn either by an electrode arranged in contact with the charge-transporting polymer and/or through a reaction with a dopant capable of increasing the conductivity of the charge-transporting polymer.

2. A charge transporting semi-conducting material according to claim 1 , further comprising an electrical dopant, wherein the electrical dopant is selected from a [3]-radialene compound, wherein each of the three carbon atoms connected to a cyclopropyl moiety of the [3]-radialene compound by a double bond is substituted independently with at least one of a nitrile group, C 6 -C 14 perfluorinated aryl, or C 2 -C 14 perfluorinated heteroaryl.

3. The charge transporting semi-conducting material according to claim 2 , wherein one to three fluorine atoms in the perfluorinated substituents are replaced by groups independently selected from nitrile or trifluoromethyl.

4. The charge transporting semi-conducting material according to claim 1 , wherein the groups from which R and R′ are selected comprise at least one substituent selected from alkyl, cycloalkyl, aryl, heteroaryl, or arylalkyl.

5. The charge transporting semi-conducting material according to claim 4 , wherein when at least one of R and R′ comprises the substituent selected from alkyl, cycloalkyl, aryl, heteroaryl, or arylalkyl, the alkyl, cycloalkyl, aryl, heteroaryl, or arylalkyl is partially or fully substituted with halogen atoms.

6. A method for preparing the charge transporting semi-conducting material according to claim 1 , the method comprising:
i) providing a solution containing
a) a first precursor charge transporting polymer comprising at least one covalently attached azide group; and/or a second precursor charge transporting polymer comprising at least one covalently attached acetylenic group,
b) at least one solvent,

ii) depositing the solution on a substrate,
iii) removing the solvent, and
iv) reacting the azide and acetylenic groups to effect crosslinking.

7. The method according to claim 6 , wherein the first precursor charge transporting polymer further comprises at least one acetylenic group, and/or the second precursor charge transporting polymer comprises at least one azide group.

8. The method according to claim 6 , wherein the solution further comprises at least one crosslinking agent comprising at least two functional groups selected from an azide and/or an acetylenic group.

9. A semiconducting device comprising a semi-conducting layer comprising a charge transporting semi-conducting material according to claim 1 .

10. The device of claim 9 , wherein the semiconducting layer is made by a printing process.

Assignees

• Novaled Gmbh

Inventors

• Zoellner Mike
• Lederer Kay
• Kiriy Anton
• Senkovskyy Volodymyr
• Voit Brigitte Isabell

Classifications

• C08G12/28

  with substituted diazines, diazoles or triazoles · CPC title

• C08G2261/146

  Side-chains containing halogens · CPC title

• C08G2261/12

  Copolymers · CPC title

• C08G2261/1422

  containing OH groups · CPC title

• C08G61/123

  derived from five-membered heterocyclic compounds · CPC title