IP Library Granted Patent US 9,673,394
Granted Patent B2
US 9,673,394 · App. 12/738,471 · Granted Jun 6, 2017

Conducting formulation

Inventors: Mark James (Romsey, GB); Iain McCulloch (Southampton, GB); Warren Duffy (Southampton, GB); Philip Edward May (Sidcup, GB); Dan Walker (Southampton, GB); David P. Waller (Lexington, MA); Richard Kendall Childers (Dracut, MA); Sheila E. Rodman (Malden, MA)
Assignee: MERCK PATENT GMBH
H01L51/0003B82Y10/00C09D11/52H01G11/48H01B1/122H01L51/0036H01L51/0046Y02E10/549Y02E60/13
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Quick Facts
Patent No.
US 9,673,394
App. No.
12/738,471
Granted
Jun 6, 2017
Kind
B2
Abstract

The invention relates to novel formulations comprising an organic semiconductor (OSC) and a conductive additive, to their use as conducting inks for the preparation of organic electronic (OE) devices, especially organic photovoltaic (OPV) cells, to methods for preparing OE devices using the novel formulations, and to OE devices and OPV cells prepared from such methods and formulations.

Claims (21)

1. A formulation comprising:

one or more organic semiconducting (OSC) compounds,

one or more organic solvents, and

one or more conductive additives that increase the conductivity of the formulation;

wherein said conductive additives are volatile and/or are not capable of chemically reacting with the OSC compounds and/or wherein the conductive additives are present in a total concentration of less than 0.5% by weight in the formulation; and

wherein the conductive additives comprise one or more non-oxidizing organic salts and the concentration of non-oxidizing salts in the formulation is from 50 ppm to 0.1% by weight, and

wherein the non-oxidizing organic salts are selected from the group consisting of phosphonium salts, imidazolium salts and other heterocyclic salts excluding heterocyclic ammonium salts, wherein the non-oxidizing organic salts have an anion that is selected from the group consisting of halides, sulfates, acetate, formate, tetrafluoroborate, hexafluorophosphate, methanesulfonate, triflate (trifluoromethanesulfonate) and bis(trifluoromethylsulfonyl)imide.

2. The formulation according to claim 1 , wherein the formulation has a conductivity from 10 −6 to 10 −9 S/m.

3. The formulation according to claim 1 , wherein the formulation comprises a first solvent having a good dissolving power for the OSC compounds, and a second carrier solvent being miscible with the first solvent and having a good dissolving power for the conductive additive.

4. The formulation according to claim 3 , wherein the first solvent is selected from the group consisting of toluene, o-, m- or p-xylene, trimethyl benzene, tetralin, anisole, alkyl anisoles, naphthalene and alkyl naphthalene.

5. The formulation according to claim 3 , wherein the carrier solvent is selected from the group consisting of cyclopentanone, acetonitrile, benzonitrile, nitromethane, tetrahydrofuran and acetone.

6. The formulation according to claim 3 , wherein the proportion of the carrier solvent is from 5 to 25 vol. % of the total volume of the formulation.

7. Formulation according to claim 1 , wherein the OSC compounds are selected from the group consisting of substituted polyacenes or poly(3-substituted thiophene).

8. The formulation according to claim 1 , wherein the formulation comprises a p type OSC compound and an n type OSC compound.

9. The formulation according to claim 1 , wherein the formulation comprises a mixture of poly(3-substituted thiophene) with a C 60 or C 70 fullerene or (6,6)phenyl C 61 butyric acid methyl ester.

10. The formulation according to claim 1 , wherein the total concentration of the OSC compounds in the formulation is from 0.1% to 10% by weight.

11. A method for coating or printing which comprises applying a formulation according to claim 1 as a coating or printing ink.

12. A process for preparing an organic electronic (OE) device, comprising the steps of

a) depositing the formulation according to claim 1 onto a substrate to form a film or layer,

b) removing the solvent(s) and any conductive additives that are volatile or capable of chemically reacting with the OSC material.

13. The method of claim 12 , wherein the solvent(s) and any conductive additives that are volatile or capable of chemically reacting with the OSC material are removed by evaporation.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2020
From: MERCK PATENT GMBH
To: RAYNERGY TEK INCORPORATION
Reel/Frame 053283/0990 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY DATA PREVIOUSLY RECORDED ON REEL 024246 FRAME 0383. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT OF ENTIRE INTEREST. Recorded Aug 18, 2014
From: JAMES, MARK; MCCULLOCH, IAIN; DUFFY, WARREN; MAY, PHILIP EDWARD; WALKER, DAN; WALLER, DAVID P.; CHILDERS, RICHARD KENDALL; RODMAN, SHEILA E.
To: MERCK PATENT GESELLSCHAFT MIT BESCHRÄNKTER HAFTUNG; KONARKA TECHNOLOGIES GMBH
Reel/Frame 033558/0304 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2010
From: JAMES, MARK; MCCULLOCH, IAIN; DUFFY, WARREN; MAY, PHILIP EDWARD; WALKER, DAN; WALLER, DAVID P.; CHILDERS, RICHARD KENDALL; RODMAN, SHEILA E.
To: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; KORNAKA TECHNOL., INC.
Reel/Frame 024246/0383 →
Priority Claims (1)
EP 07020363 · Oct 18, 2007 · regional
Continuity (1)
Related Publication 20100213455A1 · Aug 26, 2010