IP Library Granted Patent US 9,805,838
Granted Patent B2
US 9,805,838 · App. 14/240,887 · Granted Oct 31, 2017

Organic semiconductor formulation

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Quick Facts
Patent No.
US 9,805,838
App. No.
14/240,887
Granted
Oct 31, 2017
Kind
B2
Abstract

The invention relates to a formulation comprising p-type and n-type organic semiconductors (OSC) and one or more organic solvents, its use for the preparation of organic electronic (OE) devices, especially for bulk heterojunction (BHJ) organic photovoltaic (OPV) devices, to a process for preparing an OE device, especially a BHJ OPV device, using the formulation, and an OE device, especially a BHJ OPV device, prepared using such a process or formulation.

Claims (25)

1. A formulation comprising

at least one p-type organic semiconductor,

at least one n-type organic semiconductor,

at least one first solvent, which is tetralin that is substituted by two or more alkyl groups, and

at least one second solvent which is different from said first solvent and is selected from the group consisting of alkylated benzene, alkoxylated benzene, indane, alkylated indane, alkoxylated indane, tetralin, alkylated tetralin, naphthalene, alkylated naphthalene, anisole, alkylated anisole, linear ketones, cyclic ketones, aromatic ethers, aliphatic ethers, aromatic and aliphatic ethers, aromatic alcohols, optionally substituted thiophenes, benzothiophenes, alkoxylated naphthalene, substituted benzothiazoles, alkyl benzoates and aryl benzoates,

wherein the solubility of the n-type organic semiconductor in the first solvent is higher than in the second solvent, and the solubility of the p-type organic semiconductor in the second solvent is higher than in the first solvent.

2. The formulation according to claim 1 , wherein the concentration of the at least one first solvent is the same as or higher than the concentration of the at least one second solvent.

3. The formulation according to claim 1 , wherein the first solvent has a boiling point ≧150° C.

4. The formulation according to claim 1 , wherein the second solvent has a boiling point ≧100° C.

5. The formulation according to claim 1 , wherein the boiling point of the first solvent is greater than the boiling point of the second solvent.

6. The formulation according to claim 1 , which it is free of chlorinated solvents.

7. The formulation according to claim 1 , wherein the second solvent which is different from said first solvent is selected from the group consisting of xylene, cymene, indane, anisole, veratrol, dimethylanisole, tetralin, 1,5-dimethyltetralin, naphthalene, 1-methylnaphthalene, 1-ethylnaphthalene, 2-ethyl-naphthalene, 1,2-dimethylnaphthalene, 1,3-dimethylnaphthalene, 1,4-dimethylnaphthalene, 2,6-dimethylnaphthalene, 2,7-diisopropyl-naphthalene, cyclopentanone, and cyclohexanone.

8. The formulation according to claim 1 , wherein the second solvent which is different from said first solvent is selected from the group consisting of m-xylene, p-cymene, veratrole, 1,5-dimethyltetralin, 1-methylnaphthalene, 2,4-dimethylanisole and indane.

9. The formulation according to claim 1 , 1,2-dihydronapthalene, decalin, diphenyl ether, cyclohexyl benzene, methyl phenyl acetate, phenyl acetate, benzyl acetate, ethyl benzoate, gamma-terpinene, benzothiophene, thiophene, 1-methoxynaphthalene, benzyl alcohol, cyclohexanol, indene,1,4-dioxane, ethylene glycol monobutyl ether, diethyl ether, N-methylpyrrolidone, diethyl phthalate, benzyl benzoate, ethyl benzoate, acetophenone, propiophenone, 2-heptanone, cyclohexanone, benzothiazole, benzonitrile, bicyclohexyl, and methyl isobutyl ketone.

10. The formulation according to claim 1 , wherein the ratio of the first and the second solvent is 50:50 to 95:5 parts by weight.

11. The formulation according to claim 1 , wherein the p-type organic semiconductor is a conjugated organic polymer.

12. The formulation according to claim 1 , wherein the p-type organic semiconductor is a non-crystalline or semi-crystalline conjugated organic polymer.

13. The formulation according to claim 1 , wherein the p-type organic semiconductor is a conjugated organic polymer with a bandgap below 2.1 eV.

14. The formulation according to claim 1 , wherein the n-type organic semiconductor is a fullerene or fullerene derivative.

15. A formulation comprising

at least one p-type organic semiconductor,

at least one n-type organic semiconductor,

at least one first solvent, which is 1,5-dimethyltetralin, and

at least one second solvent which is different from said first solvent and is selected from the group consisting of alkylated benzene, alkoxylated benzene, indane, alkylated indane, alkoxylated indane, tetralin, alkylated tetralin, naphthalene, alkylated naphthalene, anisole, alkylated anisole, linear ketones, cyclic ketones, aromatic ethers, aliphatic ethers, aromatic and aliphatic ethers, aromatic alcohols, optionally substituted thiophenes, benzothiophenes, alkoxylated naphthalene, substituted benzothiazoles, alkyl benzoates and aryl benzoates,

wherein the solubility of the n-type organic semiconductor in the first solvent is higher than in the second solvent, and the solubility of the p-type organic semiconductor in the second solvent is higher than in the first solvent.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2020
From: MERCK PATENT GMBH
To: RAYNERGY TEK INCORPORATION
Reel/Frame 053283/0990 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2014
From: CULL, TOBY; CARRASCO-OROZCO, MIGUEL
To: MERCK PATENT GMBH
Reel/Frame 032809/0817 →