IP Library › Granted Patent US 11,377,570
Granted Patent B2
US 11,377,570 · App. 16/765,579 · Granted Jul 5, 2022

Ink composition for organic light emitting device

Inventors: Mi Kyoung Kim (Daejeon, KR); Ji Young Jung (Daejeon, KR)
C09D11/50C09D11/033C09D11/037C09D11/322C09D11/36C09D11/52H01L51/005H01L51/006H01L51/008H01L51/0061H01L51/0058H01L51/0065H01L51/5012
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Quick Facts
Patent No.
US 11,377,570
App. No.
16/765,579
Granted
Jul 5, 2022
Kind
B2
Abstract

The present invention relates to an ink composition for an organic light emitting device that can be applied to an inkjet process. When the inkjet process is applied using this, it is possible to form a film having smooth and flat surfaces when dried after forming an ink film.

Claims (52)

1. An ink composition for an organic light emitting device comprising:

a compound represented by the following Chemical Formula 1,

a compound represented by the following Chemical Formula 2, and

a solvent:

in Chemical Formula 1,

L and L 1 to L 4 are each independently a substituted or unsubstituted C 6-60 arylene,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl,

R 1 to R 4 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1-60 alkyl, a substituted or unsubstituted C 1-60 alkoxy, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S,

Y 1 to Y 4 are each independently hydrogen, or —X-A, with the proviso that two or more of Y 1 to Y 4 are —X-A,

X is O or S,

A is a functional group which can be crosslinked by heat or light,

n1 and n4 are each an integer of 0 to 4,

n2 and n3 are each an integer of 0 to 3,

in Chemical Formula 2,

R is C 3-60 alkyl; C 3-60 alkenyl; or phenyl substituted with C 3-60 alkyl, and

n is an integer of 4 to 20.

2. The ink composition according to claim 1 ,

wherein A is any one selected from the group consisting of the following:

wherein,

T 1 is hydrogen; or a substituted or unsubstituted C 1-60 alkyl, and

T 2 to T 4 are each independently a substituted or unsubstituted C 1-6 alkyl.

3. The ink composition according to claim 1 ,

wherein the Chemical Formula 1 is represented by any one of the following Formulas 1-1 to 1-4:

in Chemical Formulas 1-1 to 1-4,

R 1 to R 4 , n1 to n4, Ar 1 , Ar 2 and L are as defined in Chemical Formula 1 of claim 1 ,

X 1 to X 4 are each independently O or S,

A 1 to A 4 are each independently a functional group that can be crosslinked by heat or light,

R 21 to R 26 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1-60 alkyl, a substituted or unsubstituted C 1-60 alkoxy, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S, and

p1 and p2 are each an integer of 0 to 5,

p3 and p4 are each an integer of 0 to 4, and

p5 and p6 are each an integer of 0 to 7.

4. The ink composition according to claim 1 ,

wherein L is the following Chemical Formula 1-A or 1-B:

in Chemical Formulas 1-A and 1-B,

R 11 to R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1-60 alkyl, a substituted or unsubstituted C 1-60 alkoxy, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S, and

m1 to m3 are each an integer of 0 to 4.

5. The ink composition according to claim 1 ,

wherein the Chemical Formula 1 is any one selected from the group consisting of the following:

6. The ink composition according to claim 1 ,

wherein R is C 10-20 alkyl; C 10-20 alkenyl; or phenyl substituted with C 10-20 alkyl.

7. The ink composition according to claim 1 ,

wherein the compound represented by Chemical Formula 2 is included in an amount of 0.05 to 1% by weight relative to the total weight of the ink composition.

8. The ink composition according to claim 1 ,

wherein the solvent has a boiling point of 180° C. or more.

9. The ink composition according to claim 1 ,

wherein the solvent is aliphatic esters, aromatic esters, aliphatic ethers, aromatic ethers, aliphatic hydrocarbons, aromatic hydrocarbons, aliphatic alcohols, aromatic alcohols, or glycol ethers.

10. The ink composition according to claim 1 ,

wherein the solvent is triethylene glycol monobutyl ether, diethylene glycol dibutyl ether, tetraethylene glycol dimethyl ether, tetraethylene glycol n-butyl ether, triethylene glycol monoisopropyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monoisobutyl ether, dipropylene glycol n-butyl ether, 3-phenoxytoluene, dibenzyl ether, bis(methoxymethyl)benzene, isoamylbenzoate, isoamyl octanoate, decylbenzene, 1-methoxynaphthalene, phenethyl octanoate, 1,3-dimethoxybenzene, ethyl 4-methoxybenzoate, hexyl benzoate, 1-ethylnaphthalene, cyclohexylbenzene, octylbenzene, 2-ethylnaphthalene, benzyl butyrate, p-anisaldehyde dimethyl acetal, 3-phenyl-1-propanol, p-propylanisole, ethyl benzoate, butyl phenyl ether, 3,4-dimethylanisole, ethylene glycol monobenzyl ether, diethylene glycol monophenyl ether, dibutyl oxalate, or 3-phenoxybenzyl alcohol.

11. The ink composition according to claim 1 ,

further comprising a p-type doping material.

12. The ink composition according to claim 11 ,

wherein the p-type doping material is represented by any one of the following Chemical Formulas A to H:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2020
From: KIM, MI KYOUNG; JUNG, JI YOUNG
To: LG CHEM, LTD.
Reel/Frame 052724/0682 →
Priority Claims (1)
KR 10-2018-0103831 · Aug 31, 2018 · national
Continuity (1)
Related Publication 20200308435A1 · Oct 1, 2020