IP Library Granted Patent US 11,069,856
Granted Patent B2
US 11,069,856 · App. 15/696,549 · Granted Jul 20, 2021

Solution for organic EL, method of producing organic EL device and organic EL device

Inventors: Tomohiko Oda (Tokyo, JP); Shinichiro Ishino (Tokyo, JP); Koyo Sakamoto (Tokyo, JP); Yasuhiro Yamauchi (Tokyo, JP)
Assignee: JOLED INC.
H01L51/0007C09K11/02C09K11/06H01L51/005H01L51/0052C09K2211/1011H01L27/3211
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Quick Facts
Patent No.
US 11,069,856
App. No.
15/696,549
Granted
Jul 20, 2021
Kind
B2
Abstract

According to one embodiment, a solution for organic EL contains a mixed solvent of two or more kinds of organic solvents which contain at least a first organic solvent and a second organic solvent, and an organic EL contributing material dissolved into the mixed solvent. The coordinates (HSP coordinates) specified by Hansen solubility parameters of the first organic solvent are Hd in a range of 17.5 to 19.5 (J/cm 3 ) 1/2 , Hp in a range of 3.5 to 5.5 (J/cm 3 ) 1/2 and Hh in a range of 3.5 to 5.5 (J/cm 3 ) 1/2 . The HSP coordinates of the second organic solvent are Hd in a range of 17.5 to 19.5 (J/cm 3 ) 1/2 , Hp in a range of 0 to 2.0 (J/cm 3 ) 1/2 , and Hh in a range of 0.5 to 2.5 (J/cm 3 ) 1/2 .

Claims (21)

1. An organic EL ink suitable for a printing apparatus, comprising:

a mixed solvent of two or more kinds of organic solvents which contain at least a first organic solvent and a second organic solvent; and

an organic EL contributing material dissolved into the mixed solvent,

wherein the first organic solvent comprises benzyl butyrate, wherein HSP coordinates of the second organic solvent are Hd in a range of 17.5 to 19.5 (J/cm3) 1/2 , Hp in a range of 0 to 2.0 (J/cm3) 1/2 , and Hh in a range of 0.5 to 2.5 (J/cm3) 1/2 , and

wherein the second organic solvent comprises mesitylene, cyclohexylbenzene, toluene, benzene, p-diethylbenzene, ethylbenzene, o-n-butyltoluene, 1,2-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,1-diphenylpentane, 1,1-diphenylhexane, 3-(1-methylethenyl)toluene, 1-methyl-3-propylbenzene, 1-methyl-4-methylethyl)-2-(1-propenyl)benzene, pentamethylbenzene, isopropylbenzene, 1,2,4-trimethylbenzene, 2,2-diphenylpropane, 2-ethyldiphenylmethane, 1,4-dimethyltetraline, calamenene, 1-butyl-1,2,3,4-tetrahydronaphthalene, 3-ethyldiphenylmethane, 1,1-diphenylpropane, 3-ethylbiphenyl, 3-methyldiphenylmethane, 1,1-diphenylbutane, 3,3′-dimethylbiphenyl, 3,3′,4,4′-tetramethylbiphenyl, 3,3′,5,5′-tetramethylbiphenyl, diethylbiphenyl, (S)-1,2-dihydro-4,7-dimethyl-1-isopropylnaphthalene, and/or(S)-1,2-dihydro-1,6-dimethyl-4-isopropylnaphthalene.

2. The organic EL ink claim 1 , wherein the organic EL contributing material is one of a light-emitting material, a carrier transport material, a carrier injection material and a carrier blocking material.

3. The organic EL ink of claim 1 , wherein the organic EL contributing material comprises an anthracene-based light-emitting material.

4. A method of manufacturing an organic EL device comprising a structure in which an organic layer containing a light-omitting layer is sandwiched between two sheets of electrodes; the method comprising:

applying the organic EL ink of claim 1 ; and

drying the solution, thereby forming the organic layer.

5. The organic EL ink suitable for a printing apparatus, comprising:

a mixed solvent of two or more kinds of organic solvents which contain at least a first organic solvent and a second organic solvent; and

an organic EL contributing material dissolved into the mixed solvent,

wherein HSP coordinates of the first organic solvent are Hd in a range of 17.5 to 19.5 (J/cm3) 1/2 , Hp in a range of 3.5 to 5.5 (J/cm3) 1/2 and Hh in a range of 3.5 to 5.5 (J/cm3) 1/2 ,

wherein the first organic solvent comprises ethyl phenylacetate, m-tolyl acetate, o-tolyl acetate, o-methylbenzyl acetate, propyl phenylacetate, propyl 2-phenylacetate, styralyl acetate, methyl phenylacetate, methylphenyl carbonyl acetate, methylbenzyl acetate, propyl 3-phenylacetate, allyl phenylacetate, benzyl butyrate, o-cresyl isobutyrate, cresyl butyrate, p-cresyl isobutyrate, p-anisyl isobutyrate, methyl 4-phenylbutyrate, benzyl propionate, phenethyl propionate, styralyl propionate, cinnamyl propionate, p-cresyl propionate, p-methylanisole, m-methylanisole, o-methylanisole, 2,4-dimethylanisole, o-vinylanisole, 4-ethylanisole, phenylacetaldehyde ethylene acetal, benzaldehyde propylene acetal, 2-(a-methylbenzyl)-1,3-dioxolane, cinnamaldehyde dimethyl acetal, o-diethoxybenzene, p-methoxystyrene 2-ethoxynaphthalene, 4-allylanisole, 3,4-dimethoxystyrene, 1-ethoxynaphthalene, octyl methoxycinnamate, 2,5-dimethoxystyrene, 2,6-dimethoxystyrene, 1-methoxy-4-propoxybenzene, benzyl methylether, butyl phenyl ether, ethyl phenyl ether, benzyl ethyl ether, phenyl isopropyl ether, phenyl propyl ether, allyl phenyl ether phenylvinyl ether, anethole, dihydroanethole, benzalacetone, phenyl ethylidene acetone, 2-(4-isopropylphenyl)propanal, and/or 3-(4-isopropylphenyl)propanal, and

wherein the second organic solvent comprises diphenylpropane.

6. The organic EL ink claim 5 , wherein the organic EL contributing material is one of a light-emitting material, a carrier transport material, a carrier injection material and a carrier blocking material.

7. The organic EL ink of claim 5 , wherein the organic EL contributing material comprises an anthracene-based light-emitting material.

8. A method of manufacturing an organic EL device comprising a structure in which an organic layer containing a light-emitting layer is sandwiched between two sheets of electrodes; the method comprising:

applying the organic EL ink of claim 5 ; and

drying the solution, thereby forming the organic layer.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2025
From: JDI DESIGN AND DEVELOPMENT G.K.
To: MAGNOLIA BLUE CORPORATION
Reel/Frame 072039/0656 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2024
From: JOLED, INC.
To: JDI DESIGN AND DEVELOPMENT G.K.
Reel/Frame 066382/0619 →
CORRECTION BY AFFIDAVIT FILED AGAINST REEL/FRAME 063396/0671 Recorded Jun 12, 2023
From: JOLED, INC.
To: JOLED, INC.
Reel/Frame 064067/0723 →
SECURITY INTEREST Recorded Apr 20, 2023
From: JOLED, INC.
To: INCJ, LTD.
Reel/Frame 063396/0671 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2017
From: ODA, TOMOHIKO; ISHINO, SHINICHIRO; SAKAMOTO, KOYO; YAMAUCHI, YASUHIRO
To: JOLED INC.
Reel/Frame 043502/0182 →