Printing ink formulations, preparation methods and uses thereof

Patent metadata

Field	Value
Publication number	US-11248138-B2
Application number	US-201716463526-A
Country	US
Kind code	B2
Filing date	Nov 23, 2017
Priority date	Nov 23, 2016
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

A printing ink formulation includes a functional material and a solvent being evaporable from the printing ink formulation to form a functional material thin film. The solvent is formed by mixing at least two organic solvents including a first solvent and a second solvent. The solvent system containing at least two solvents can effectively dissolve the functional material without the need of adding an additive, and can also effectively prevent the occurrence of a “coffee-ring effect”, and accordingly, the thin film containing a uniform thickness and a strong electron transmission capability can be obtained.

First claim

The invention claimed is:

1. A printing ink formulation, comprising a functional material and a solvent, the solvent could be evaporable from the printing ink formulation to form a functional film;
wherein the solvent is formed by mixing at least two organic solvents including a first solvent and a second solvent, the first solvent and the second solvent are miscible, and at least one of the first solvent and the second solvent has a boiling point greater than or equal to 160° C., the second solvent has a surface tension less than that of the first solvent and a viscosity greater than that of the first solvent, and the difference in surface tension between the first solvent and the second solvent is at least 2 dyne/cm, and the difference in viscosity between the second solvent and the first solvent is at least 2 cPs,
wherein the functional material is an inorganic nanomaterial or an organic functional material, and wherein the organic functional material is selected from the group consisting of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, emitters, host materials, and organic dyes.

2. The printing ink formulation according to claim 1 , wherein at least one of the first solvent and the second solvent has a surface tension between 19 dyne/cm and 50 dyne/cm at 25° C.

3. The printing ink formulation according to claim 1 , wherein at least one of the first solvent and the second solvent has a viscosity between 1 cPs and 100 cPs at 25° C.

4. The printing ink formulation according to claim 1 , wherein the first solvent is present in an amount between 30 wt % and 90 wt % based on the total weight of the solvent, and the second solvent is present in an amount between 10 wt % and 70 wt % based on the total weight of the solvent.

5. The printing ink formulation according to claim 1 , wherein the first solvent or the second solvent is each independently selected from the group consisting of a substituted or unsubstituted aromatic solvent, a substituted or unsubstituted heteroaromatic solvent, an aromatic ketone solvent, an aromatic ether solvent, ester solvent, a linear aliphatic solvent, an alicyclic solvent, an aliphatic ketone solvent, an aliphatic ether solvent, an alcohol solvent, and an inorganic ester solvent.

6. The printing ink formulation according to claim 5 , wherein the substituted or unsubstituted aromatic solvent is selected from the group consisting of p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene 1-methylnaphthalene, 1,2,4-trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, and 2-isopropyl naphthalene;
the substituted or unsubstituted heteroaromatic solvent is selected from the group consisting of 2-phenylpyridine, 3-phenylpyridine, 4-(3-phenylpropyl)pyridine, quinoline, isoquinoline, 8-hydroxyquinoline, methyl 2-furancarboxylate, and ethyl 2-furancarboxylate;
the aromatic ketone solvent is selected from the group consisting of: 1-tetralone, 2-tetralone, acetophenone, propiophenone or benzophenone, the 1-tetralone or 2-tetralone is each independently, optionally substituted by a substituent of an aliphatic group, an aryl group, a heteroaryl group or a halogen; the acetophenone, propiophenone or benzophenone is each independently, optionally substituted by a methyl group;
the aromatic ether solvent is selected from the group consisting of 3-phenoxytoluene, butoxybenzene, benzyl butylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylphenetole, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenyl anisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether;
the ester solvent is selected from the group consisting of alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, and alkyl oleate;
the cycloaliphatic solvent is selected from the group consisting of tetrahydronaphthalene, cyclohexylbenzene, decahydronaphthalene, 2-phenoxytetrahydrofuran, 1,1′-bicyclohexane, butylcyclohexane, ethyl rosinate, benzyl rosinate, ethylene glycol carbonate, styrene oxide, isophorone, 3,3,5-trimethylcyclohexanone, cycloheptanone, fenchone, 1-tetralone, 2-tetralone, 2-(phenyl epoxy)tetralone, 6-(m ethoxy)tetralone, γ-butyrolactone, γ-valerolactone, 6-caprolactone, N,N-diethyl cyclohexylamine, sulfolane, and 2,4-dimethylsulfolane;
the aliphatic ketone solvent is selected from the group consisting of 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, di-n-pentyl ketone, phorone, isophorone, 2,6,8-trimethyl-4-nonanone, camphor, and fenchone;
the aliphatic ether solvent is selected from the group consisting of pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether;
the inorganic ester solvent is selected from the group consisting of tributyl borate, tripentyl borate, trimethyl phosphate, triethyl phosphate, tributyl phosphate, tris(2-ethylhexyl) phosphate, triphenyl phosphate, diethyl phosphate, dibutyl phosphate, and di(2-ethylhexyl)phosphate.

7. The printing ink formulation according to claim 6 , wherein the second solvent is 1-tetralone and the first solvent is quinolone or isoquinolone;
or, the second solvent is 3-phenoxytoluene and the first solvent is selected from the group consisting of chlorophthalene, styrene oxide, quinoline and isoquinoline;
or, the second solvent is 3-isopropylbiphenyl, and the first solvent is selected from the group consisting of 3-phenoxytoluene, acetophenone, tetrahydronaphthalene, chloronaphthalene, 1,4-dimethylnaphthalene, 1-methylnaphthalene, diphenyl ether, diphenylmethane, 2-isopropylnaphthalene, styrene oxide, quinoline and isoquinoline;
or, the second solvent is isononyl isononanoate, the first solvent is selected from the group consisting of 3-phenoxytoluene, acetophenone, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, o-diethylbenzene, dodecylbenzene, diphenyl ether, diphenylmethane, 2-isopropylbenzene, octyl octanoate, 1,1-bicyclohexane, butyrolactone, isophorone, cycloheptanone and triethyl phosphate;
or, the second solvent is sulfolane, and the first solvent is selected from the group consisting of 3-phenoxytoluene, acetophenone, chloronaphthalene, 1,4-dimethylnaphthalene, 1-methylnaphthalene, diphenyl ether, ethylene glycol carbonate, quinoline and isoquinoline;
or, the second solvent is dodecylbenzene, and the first solvent is selected from the group consisting of acetophenone, tetrahydronaphthalene, chloronaphthalene, 1-methylnaphthalene, diphenylmethane, butyrolactone, isophorone and isoquinoline;
or, the second solvent is 2,4-dimethyl sulfolane, and

Assignees

• Guangzhou Chinaray Optoelectronic Mat Ltd

Inventors

• Pan Junyou
• Yang Xi
• Yan Xiaolin

Classifications

• C09D11/50 Primary

  Sympathetic, colour changing or similar inks · CPC title

• C09D11/033 Primary

  characterised by the solvent · CPC title

• H10H20/823

  comprising only Group II-VI materials, e.g. ZnO · CPC title

• H10H20/811

  having quantum effect structures or superlattices, e.g. tunnel junctions · CPC title

• C09D11/36

  based on non-aqueous solvents · CPC title