Non-aqueous ink compositions containing metallic nanoparticles suitable for use in organic electronics

Patent metadata

Field	Value
Publication number	US-2018201799-A1
Application number	US-201615743557-A
Country	US
Kind code	A1
Filing date	Jul 6, 2016
Priority date	Jul 17, 2015
Publication date	Jul 19, 2018
Grant date	—

Abstract

Described herein are non-aqueous ink compositions containing a polythiophene having a repeating unit complying with formula (I) described herein, one or more metallic nanoparticles, and a liquid carrier having one or more organic solvents. The present disclosure also concerns the uses of such non-aqueous ink compositions, for example, in organic electronic devices.

First claim

What is claimed is:

1 . A non-aqueous ink composition comprising:
(a) a polythiophene comprising a repeating unit complying with formula (I)

wherein R 1 and R 2 are each, independently, H, alkyl, fluoroalkyl, alkoxy, aryloxy, or —O—[Z—O] p —R e ;
wherein
Z is an optionally halogenated hydrocarbylene group,
p is equal to or greater than 1, and
R e is H, alkyl, fluoroalkyl, or aryl;

(b) one or more metallic nanoparticles; and
(c) a liquid carrier comprising one or more organic solvents.

2 . The non-aqueous ink composition according to claim 1 , 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 f ; wherein each occurrence of R a , R b , R c , and R d , are each, independently, H, halogen, alkyl, fluoroalkyl, or aryl; R e is H, alkyl, fluoroalkyl, or aryl; p is 1, 2, or 3; and R f is alkyl, fluoroalkyl, or aryl.

3 . The non-aqueous ink composition according to claim 1 or 2 , wherein R 1 is H and R 2 is other than H.

4 . The non-aqueous ink composition according to claim 1 or 2 , wherein R 1 and R 2 are both other than H.

5 . The non-aqueous ink composition according to claim 4 , 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 .

6 . The non-aqueous ink composition according to claim 5 , wherein R 1 and R 2 are both —O[C(R a R b )—C(R c R d )—O] p —R e .

7 . The non-aqueous ink composition according to any one of claims 2 - 6 , 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.

8 . The non-aqueous ink composition according to any one of claims 1 - 7 , wherein the polythiophene comprises a repeating unit selected from the group consisting of

and combinations thereof.

9 . The non-aqueous ink composition according to any one of claims 1 - 8 , wherein the polythiophene is sulfonated.

10 . The non-aqueous ink composition according to any one of claims 1 - 9 , 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, based on the total weight of the repeating units.

11 . The non-aqueous ink composition according to any one of claims 1 - 10 , wherein the polythiophene comprising a repeating unit complying with formula (I) is doped with a dopant.

12 . The non-aqueous ink composition according to claim 11 , wherein the dopant comprises a tetraarylborate.

13 . The non-aqueous ink composition according to claim 12 , wherein the dopant comprises tetrakis(pentafluorophenyl)borate (TPFB).

14 . The non-aqueous ink composition according to any one of claims 1 - 13 , wherein the one or more metallic nanoparticles comprise a transition metal oxide.

15 . The non-aqueous ink composition according to claim 14 , wherein the one or more metallic nanoparticles comprise zirconium oxide (ZrO 2 ), titanium dioxide (TiO 2 ), zinc oxide (ZnO), vanadium(V) oxide (V 2 O 5 ), molybdenum trioxide (MoO 3 ), tungsten trioxide (WO 3 ), or mixtures thereof.

16 . The non-aqueous ink composition according to claim 14 or 15 , wherein the metallic nanoparticles comprise one or more organic capping groups.

17 . The non-aqueous ink composition according to any one of claims 1 - 16 , wherein the amount of the metallic nanoparticles is from 1 wt. % to 90 wt. %, typically from about 2 wt. to about 80 wt. %, more typically from about 5 wt. % to about 70 wt. %, still more typically about 10 wt. % to about 60 wt. %, relative to the combined weight of the metallic nanoparticles and the doped or undoped polythiophene.

18 . A process for forming a hole-carrying film, the process comprising:
1) coating a substrate with a non-aqueous ink composition according to any one of claims 1 - 17 ; and 2) annealing the coating on the substrate, thereby forming the hole-carrying film.

19 . A hole-carrying film formed by the process according to claim 18 .

20 . The hole-carrying film according to claim 19 , wherein the film has transmittance of at least 85%, typically at least 90%, of light having a wavelength of about 380-800 nm.

21 . The hole-carrying film according to claim 19 or 20 , wherein the film has a thickness of from about 5 nm to about 500 nm, typically from about 5 nm to about 150 nm, more typically from about 50 nm to 120 nm.

22 . The hole-carrying film according to any one of claims 19 - 21 , wherein the film has a refractive index from about 1.500 to about 1.700, typically from about 1.510 to about 1.690, more typically from about 1.520 to about 1.660, when measured with light having a wavelength of about 380-800 nm.

23 . A device comprising the hole-carrying film according to any one of claims 19 - 22 , 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

• Wang Jing
• Li Sergey B
• Difalco Laura
• Decampo Floryan
• Chen Shilei

Classifications

• C08K2003/2296

  of zinc · CPC title

• C08K3/22

  of metals · CPC title

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C09D11/106

  containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C08G2261/92

  TFT applications · CPC title