Cleaning composition for liquid crystal alignment layer and manufacturing method of liquid crystal alignment layer using the same

Patent metadata

Field	Value
Publication number	US-11008537-B2
Application number	US-201716067784-A
Country	US
Kind code	B2
Filing date	Jan 26, 2017
Priority date	Mar 3, 2016
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

The present invention relates to a cleaning composition for a liquid crystal alignment layer, a manufacturing method of a liquid crystal alignment layer using the same, and a liquid crystal display device including the liquid crystal alignment layer manufactured by the manufacturing method. More specifically, the present invention relates to a cleaning composition for a liquid crystal alignment layer that is capable of solving a non-uniformity problem of the liquid crystal alignment layer and effectively removing an ionic byproduct on a polymer surface to increase anisotropy of the liquid crystal alignment layer, by using a cleaning composition including a specific solvent in a cleaning process after a UV alignment process, and a manufacturing method of a liquid crystal alignment layer.

First claim

The invention claimed is:

1. A cleaning composition for a liquid crystal alignment layer comprising:
tetrahydrofurfuryl alcohol or methyl 2-hydroxyisobutyrate,
wherein the cleaning composition for a liquid crystal alignment layer is for cleaning a UV-aligned liquid crystal alignment layer including polyimide or a polyimide precursor,
wherein the cleaning composition includes 20 to 1-50 wt % of the tetrahydrofurfuryl alcohol or the methyl 2-hydroxyisobutyrate, and 50 to 80 wt % of at least one compound selected from the group consisting of an alkylene glycol-based compound and a polar solvent based on the total weight of the composition, and
wherein the alkylene glycol-based compound has a viscosity of 10 cP or less and a boiling point of at least 150° C. or more and the polar solvent has a viscosity of 5 cP or less and a boiling point of at least 100° C. or more.

2. The cleaning composition for a liquid crystal alignment layer of claim 1 , further comprising:
1 to 70 wt % of deionized water.

3. The cleaning composition for a liquid crystal alignment layer of claim 1 , wherein:
the alkylene glycol-based compound is at least one selected from the group consisting of diethyleneglycol tertbutyl ether, diethyleneglycol monomethyl ether, diethyleneglycol monoethyl ether, diethyleneglycol monobutyl ether, dipropyleneglycol monomethyl ether, dipropyleneglycol monoethyl ether, ethyleneglycol monomethyl ether, ethyleneglycol monobutyl ether, ethyleneglycol monoethyl ether, propyleneglycol monomethyl ether, and propyleneglycol monomethyl ether acetate.

4. The cleaning composition for a liquid crystal alignment layer of claim 1 , wherein:
the polar solvent is at least one selected from the group consisting of ethyl lactate, butyl lactate, hydroxyl acid ester, N-methyl pyrrolidone, N-ethyl pyrrolidone, N-methyl formamide, 1,3-dimethyl-2-imidazolidinone, dimethylsulfoxide, dimethylacetamide, dimethylformamide, and tetramethylenesulfone.

5. The cleaning composition for a liquid crystal alignment layer of claim 1 , wherein:
the liquid crystal alignment layer is obtained by a method including:
forming a polyimide layer by coating and firing a liquid crystal alignment agent containing at least one polymer selected from the group consisting of a polyimide and a polyimide precursor on a substrate; and performing a UV alignment process by irradiating polarized radiation to the substrate on which the polyimide layer is formed.

6. The cleaning composition for a liquid crystal alignment layer of claim 5 , wherein:
the polyimide precursor includes a repeating unit represented by Chemical Formula 1 below, and a repeating unit represented by Chemical Formula 2 below:

in Chemical Formulas 1 and 2,
X 1 and X 2 are each independently a quadrivalent organic group derived from a C4-C20 hydrocarbon, or a quadrivalent organic group in which at least one H is substituted with a halogen or at least one —CH 2 — is replaced with —O—, —S—, —CO— or —SO— so that oxygen atoms are not directly connected, in the quadrivalent organic group,
R 1 to R 4 are each independently hydrogen or a C1-C10 alkyl group,
R 5 to R 7 are each independently a halogen, a cyano group, a C2-C10 alkenyl group, a C1-C10 alkyl group, a C1-C10 alkoxy group, or a C1-C10 fluoroalkyl group,
L 1 is —O—, —O—CH 2 —O—, —O—CH 2 CH 2 —O—, or —O—CH 2 CH 2 CH 2 —O—,
p, q and r are each independently an integer of 0 to 4, and
n is an integer of 1 or 2.

7. A manufacturing method of a liquid crystal alignment layer, the manufacturing method comprising:
forming a polyimide layer by coating and firing a liquid crystal alignment agent containing at least one polymer selected from the group consisting of a polyimide and a polyimide precursor on a substrate;
performing a UV alignment process by irradiating polarized radiation to the substrate on which the polyimide layer is formed;
cleaning a polymer surface on the substrate in which the UV alignment process is completed, using a cleaning composition; and
drying the cleaned substrate,
wherein the cleaning composition includes tetrahydrofurfuryl alcohol or methyl 2-hydroxyisobutyrate, and
in the cleaning, an ionic byproduct including a UV decomposition product of the polyimide layer is washed and removed from the polymer surface of the polyimide layer by the cleaning composition.

8. The manufacturing method of claim 7 , wherein:
the cleaning composition further includes at least one compound selected from the group consisting of an alkylene glycol-based compound having a viscosity of 10 cP or less and a boiling point of at least 150° C. or more and a polar solvent having a viscosity of 5 cP or less and a boiling point of at least 100° C. or more.

9. The manufacturing method of claim 7 , wherein:
the cleaning composition includes
a) 100 wt % of the tetrahydrofurfuryl alcohol or the methyl 2-hydroxyisobutyrate, or
b) 1 to 99 wt % of the compound a); and 0.1 to 99 wt % of at least one compound selected from the group consisting of an alkylene glycol-based compound and a polar solvent.

10. The manufacturing method of claim 7 , wherein:
the cleaning composition further includes 1 to 70 wt % of deionized water.

11. The manufacturing method of claim 8 , wherein:
the alkylene glycol-based compound is at least one selected from the group consisting of diethyleneglycol tertbutyl ether, diethyleneglycol monomethyl ether, diethyleneglycol monoethyl ether, diethyleneglycol monobutyl ether, dipropyleneglycol monomethyl ether, dipropyleneglycol monoethyl ether, ethyleneglycol monomethyl ether, ethyleneglycol monobutyl ether, ethyleneglycol monoethyl ether, propyleneglycol monomethyl ether, and propyleneglycol monomethyl ether acetate.

12. The manufacturing method of claim 8 , wherein:
the polar solvent is at least one selected from the group consisting of ethyl lactate, butyl lactate, hydroxyl acid ester, N-methyl pyrrolidone, N-ethyl pyrrolidone, N-methyl formamide, 1,3-dimethyl-2-imidazolidinone, dimethylsulfoxide, dimethylacetamide, dimethylformamide, and tetramethylenesulfone.

13. The manufacturing method of claim 7 , wherein:
the firing in the forming of the polyimide layer includes a soft baking process or a hard baking process.

14. The manufacturing method of claim 7 , wherein:
the polyimide precursor includes a repeating unit represented by Chemical Formula 1 below, and a repeating unit represented by Chemical Formula 2 below:

in Chemical Formulas 1 and 2,
X 1 and X 2 are each independently a quadrivalent organic group derived from a C4-C20 hydrocarbon, or a quadrivalent organic group in which at least one H is substituted with a halogen or at least one —CH 2 — is replaced with —O—, —S—, —CO— or —SO— so that oxygen atoms are not directly connected, in the quadrivalent organic group,
R 1 to R 4 are each independently hydrogen or a C1-C10 alkyl group,
R 5 to R 7 are each independently a halogen, a cyano group, a C2-C10 alkenyl group, a C1-C10 alkyl group, a C1-C10 alkoxy group, or a C1-C10 fluoroalkyl group,
L 1 is —O—, —O—CH 2 —O—, —O—CH 2 CH 2 —O—, or —O—CH 2 CH 2 CH 2 —O—,
p, q and r are each independently an integer of 0 to 4, and
n is an integer of 1 or 2.

15. The manufacturing method of claim 7 , wherein:
the polyimide precursor has a weight average molecular weight of

Assignees

• Lg Chemical Ltd

Inventors

• Han Hee
• Yoon Jun Young
• Jo Jung Ho
• Park Hang Ah
• Kwon Soon Ho
• Yun Hyeong Seuk

Classifications

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• G02F1/133723 Primary

  Polyimide, polyamide-imide · CPC title

• C08G73/1042

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title

• C09K19/56

  Aligning agents · CPC title

• C11D7/26

  containing oxygen · CPC title