Compositions containing hole carrier materials and fluoropolymers, and uses thereof

Patent metadata

Field	Value
Publication number	US-2017369727-A1
Application number	US-201515535355-A
Country	US
Kind code	A1
Filing date	Dec 15, 2015
Priority date	Dec 15, 2014
Publication date	Dec 28, 2017
Grant date	—

Abstract

Described herein are compositions comprising hole carrier materials, typically conjugated polymers, and fluoropolymers ink compositions comprising hole carrier materials and fluoropolymers, and uses thereof, for example, in organic electronic devices.

First claim

What is claimed is:

1 . A composition comprising:
(a) at least one hole carrier material, and (b) at least one fluoropolymer.

2 . The composition according to claim 1 , wherein the at least one hole carrier material is a polymer.

3 . The composition according to claim 1 or 2 , wherein the at least one hole carrier material is a conjugated polymer.

4 . The composition according to any one of claims 1 - 3 , wherein the at least one hole carrier material is a polythiophene.

5 . The composition according to claim 4 , wherein the polythiophene comprises a repeating unit complying with formula (I)

wherein R 1 and R 2 are each, independently, H, fluoroalkyl, —O[C(R a R b )—C(R c R d )—O] p —R e , or —OR f ; wherein each occurrence of R a , R b , R c , and R d , are each, independently, H, alkyl, fluoroalkyl, or aryl; R e is alkyl, fluoroalkyl, or aryl; p is 1, 2, or 3; and R f is alkyl, fluoroalkyl, or aryl.

6 . The composition according to claim 5 , wherein R 1 is H and R 2 is other than H.

7 . The composition according to any one of claims 5 - 6 , wherein R 1 is H and R 2 is —O[C(R a R b )—C(R c R d )—O] p —R e , or —OR f .

8 . The composition according to any one of claims 5 - 7 , wherein R 1 is H and R 2 is —O[C(R a R b )—C(R c R d )—O] p —R e .

9 . The composition according to any one of claims 6 - 8 , wherein the polythiophene is regioregular.

10 . The composition according to claim 9 , wherein the degree of regioregularity is about 0 to 100%, or about 25 to 99.9%, or about 50 to 98%.

11 . The composition according to claim 5 , wherein R 1 and R 2 are both other than H.

12 . The composition according to claim 11 , wherein R 1 and R 2 are each, independently, —O[C(R a R b )—C(R c R d )—O] p —R e , or —OR f .

13 . The composition according to any one of claims 11 - 12 , wherein R 1 and R 2 are both —O[C(R a R b )—C(R c R d )—O] p —R e .

14 . The composition according to any one of claims 11 - 13 , wherein R 1 and R 2 are each —O[CH 2 —CH 2 —O] p —R e .

15 . The composition according to any one of claims 11 - 13 , wherein R 1 and R 2 are each —O[CH(CH 3 )—CH 2 —O] p —R e .

16 . The composition according to any one of claims 5 - 13 , wherein each occurrence of R a , R b , R c , and R d , are each, independently, H, (C 1 -C 8 )alkyl, (C 1 -C 8 )fluoroalkyl, or phenyl; and R e is (C 1 -C 8 )alkyl, (C 1 -C 8 )fluoroalkyl, or phenyl.

17 . The composition according to any one of claims 5 - 16 , wherein R e is methyl, propyl, or butyl.

18 . The composition according to any one of claims 5 - 17 , wherein the polythiophene comprises a repeating unit selected from the group consisting of

and combinations thereof.

19 . The composition according to any one of claims 5 - 18 , wherein the polythiophene comprises repeating units complying with formula (I) in an amount of greater than 70% by weight, typically greater than 80% by weight, more typically greater than 90% by weight, even more typically greater than 95% by weight, of the conjugated polymer.

20 . The composition according to any one of claims 5 - 19 , wherein the polythiophene is a homopolymer.

21 . The composition according to any one of claims 1 - 20 , wherein the conjugated polymer typically has a number average molecular weight between about 1,000 and 1,000,000 g/mol, more typically, between about 5,000 and 100,000 g/mol, even more typically about 10,000 to about 50,000 g/mol.

22 . The composition according to any one of claims 1 - 21 , wherein the at least one hole carrier material is doped with a dopant.

23 . The composition according to claim 22 , wherein the dopant comprises a tetraarylborate.

24 . The composition according to claim 23 , wherein the dopant comprises tetrakis(pentafluorophenyl)borate.

25 . The composition according to claim 24 , wherein the dopant is silver tetrakis(pentafluorophenyl)borate.

26 . The composition according to any one of claims 1 - 25 , wherein the fluoropolymer is a partially fluorinated polymer.

27 . The composition of claim 26 , wherein the partially fluorinated polymer comprises repeating units derived from vinylidene fluoride monomers.

28 . The composition of according to any one of claims 26 - 27 , wherein the partially fluorinated polymer is a PVDF copolymer.

29 . The composition of according to any one of claims 28 , wherein the PVDF copolymer is a copolymer of vinylidene fluoride with at least one monomer selected from the group consisting of trifluoroethylene, tetrafluoroethylene, pentafluoropropene, 3,3,3-trifluoropropene, hexafluoropropylene, and chlorotrifluoroethylene.

30 . The composition according to any one of claims 28 - 29 , wherein the PVDF copolymer is PVDF-hexafluoropropylene (PVDF-HPF) copolymer.

31 . The composition according to any one of claims 28 - 30 , wherein the PVDF copolymer comprises repeating units derived from vinylidene fluoride in an amount of greater than 70% by weight of the copolymer.

32 . The composition according to any one of claims 28 - 31 , wherein the PVDF copolymer does not comprise —OM, —SO 3 M, and/or —CO 2 M, wherein M is H + , an alkali metal ion, or ammonium ion.

33 . The composition according to any one of claims 28 - 32 , wherein the PVDF copolymer does not comprise sulfonimide, phosphonic acid, and/or phosphoric acid groups.

34 . The composition according claim 27 , wherein the partially fluorinated polymer comprising repeating units derived from vinylidene fluoride monomers is PVDF homopolymer.

35 . The composition according to any one of claims 1 - 34 , wherein the ratio of hole carrier material-to-fluoropolymer (hole carrier material:fluoropolymer ratio), by weight, is from 10:1 to 1:10.

36 . The composition according to any one of claims 1 - 35 , further comprising one or more matrix materials.

37 . An ink composition comprising the composition according to any one of claims 1 - 36 and a liquid carrier.

38 . A device comprising the composition according to any one of claims 1 - 36 , wherein the device is an OLED, OPV, transistor, capacitor, sensor, transducer, drug release device, electrochromic device, or battery device.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• De Campo Floryan
• Swisher Robert
• Sheina Elena

Classifications

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C08G2261/90

  Applications · CPC title

• C08G2261/92

  TFT applications · CPC title

• C08G2261/792

  with low-molecular weight dopants · CPC title