IP Library › Granted Patent US 10,676,671
Granted Patent B2
US 10,676,671 · App. 15/744,114 · Granted Jun 9, 2020

Method of reducing ODF mura in polymer stabilised liquid crystal displays

Inventors: Leo Weegels (Darmstadt, DE); Roger Chang (Taipei, TW); Ky Lin (Taipei, TW)
Assignee: Merck Patent GmbH
C09K19/542C09K19/062C09K19/3003C09K19/32C09K19/322G02F1/1337G02F1/1339G02F1/1341C09K2019/0448C09K2019/0481C09K2019/122C09K2019/123C09K2019/301C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3425C09K2019/548G02F2001/13415G02F2001/133302
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Quick Facts
Patent No.
US 10,676,671
App. No.
15/744,114
Granted
Jun 9, 2020
Kind
B2
Abstract

The present invention relates to a method of reducing ODF mura in liquid crystal (LC) displays of the polymer sustained alignment (PSA) type and to PSA LC displays made by this method.

Claims (94)

1. A method of reducing the One Drop Filling (ODF) mura in a liquid crystal display (LCD) of the polymer stabilised alignment (PSA) mode, comprising providing or using in the PSA display an LC medium, comprising

a polymerisable component A) comprising 0.005 to 0.02% of a first polymerisable compound and 0.2 to 0.3% of a second polymerisable compound, wherein the first polymerisable compound has faster polymerisation speed than the second polymerisable compound, the first polymerisable compound is one or more compounds of formulae F1-F6, and the second polymerisable compound is one or more compounds of formulae S1-S3, and

a liquid-crystalline component B), comprising one or more mesogenic or liquid-crystalline compounds

in which

P each, independently, is a polymerisable group,

Sp each, independently, is a spacer group or a single bond,

Sp′ is a spacer group,

L each, independently, is F, Cl, CN or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,

R a , R b each, independently, is -Sp-P, -Sp′(P) 2 , H or one of the meanings given for L,

r is 0, 1, 2, 3 or 4,

s is 0, 1, 2 or 3, and

t is 0, 1 or 2.

2. The method of claim 1 , wherein in the one or more compounds of formulae F1-F6 and S1-S3 the group P denotes CH 2 ═CW 1 —CO—O—, wherein W 1 is H, F, CF 3 or alkyl having 1 to 5 C atoms.

3. The method of claim 1 , wherein the one or more compounds of formulae F1-F6 are selected from compounds of the following formulae

wherein

P each, independently, is a polymerisable group,

Sp each, independently, is a spacer group or a single bond,

Sp′ is a spacer group,

L, L′ each, independently, is F, Cl, CN or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,

r is 0, 1, 2, 3 or 4,

s is 0, 1, 2 or 3, and

t is 0, 1 or 2.

4. The method according to claim 1 , wherein the one or more compounds of formulae S1-S3 are selected from compounds of the following formulae

wherein

P each, independently, is a polymerisable group,

Sp′ is a spacer group,

L′ is F, Cl, CN or straight-chain or branched, optionally mono- or poly-fluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms.

5. The method according to claim 1 , wherein in the one or more compounds of formulae F1-F6 and S1-S3 the group Sp′, and those groups Sp that are not a single bond, each independently, denote —(CH 2 ) p1 —, —(CH 2 ) p1 —O—, —(CH 2 ) p1 —O—CO—, —(CH 2 ) p1 —CO—O—, or —(CH 2 ) p1 —O—CO—O—, in which p1 denotes an integer from 1 to 6, and wherein these groups Sp′ and Sp that are not a single bond are linked to the polymerisable group P such that two O-atoms are not directly adjacent to each other.

6. The method according to claim 1 , wherein in the one or more compounds of formula F1-F6 and S1-S3 the group L′ denotes F.

7. The method according to claim 1 , wherein the LC method comprises 0.3% of the second polymerisable compound.

8. The method according to claim 1 , wherein component B) comprises one or more compounds of formulae AN and/or AY:

in which

each, independently, is

R A1 is alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, also one of the meanings of R A2 ,

R A2 is alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,

Z x is —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,

L 1-4 each, independently, is H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,

x 1 or 2, and

z 0 or 1.

9. The method according to claim 1 , wherein component B) comprises one or more compounds of formulae CY and/or PY:

in which

a denotes 1 or 2,

b denotes 0 or 1,

R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,

Z x denotes —CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —O—, —CH 2 —, —CH 2 CH 2 — or a single bond,

L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 .

10. The method according to claim 1 , wherein component B) comprises one or more compounds of formulae ZK and/or DK:

in which

each, independently, denotes

and

R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,

Z y denotes —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond,

R 5 and R 6 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another, and

e denotes 1 or 2.

11. The method according to claim 1 , wherein the polymerisable compounds of component A) are polymerised.

12. A method of manufacturing an LCD of the PSA mode, comprising

a) dispensing an array of droplets ( 2 ) of an LC medium comprising components A) and B) on a first substrate ( 1 ),

wherein component A) is polymerisable and comprises 0.005 to 0.02% of a first polymerisable compound and 0.2 to 0.3% of a second polymerisable compound, wherein the first polymerisable compound has faster polymerisation speed than the second polymerisable compound, the first polymerisable compound is one or more compounds of formulae F 1 -F 6 , and the second polymerisable compound is one or more compounds of formulae S1-S3, and

component B) is liquid-crystalline and comprises one or more mesogenic or liquid-crystalline compounds

in which

P each, independently, is a polymerisable group,

Sp each, independently, is a spacer group or a single bond,

Sp′ is a spacer group,

L each, independently, is F, Cl, CN or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,

R a , R b each, independently, is -Sp-P, -Sp′(P) 2 , H or one of the meanings given for L,

r is 0, 1, 2, 3 or 4,

s is 0, 1, 2 or 3, and

t is 0, 1 or 2;

b) providing a second substrate ( 4 ) on top of the surface of the first substrate ( 1 ) that is covered by the LC medium, optionally under vacuum condition, causing the droplets ( 2 ) of the LC medium to spread and form a continuous layer between the first substrate ( 1 ) and the second substrate ( 4 ), and

c) exposing the LC medium to UV radiation that causes photopolymerisation of the polymerisable compounds of component A).

13. The method according to claim 12 , wherein the first and second substrates ( 1 , 4 ) are glass substrates.

14. The method according to claim 12 , wherein the first substrate ( 1 ) is equipped with a first electrode structure and the second substrate ( 4 ) is equipped with a second electrode structure.

15. The method according to claim 12 , wherein one of the two substrates ( 1 , 4 ) is equipped with a first and a second electrode structure, and the other of the two substrates ( 1 , 4 ) is not equipped with an electrode structure.

16. The method according to claim 12 , wherein the first substrate ( 1 ) and the second substrate ( 4 ) are each equipped with an alignment layer that is in contact with the LC medium ( 2 ).

17. The method according to claim 12 , wherein a sealant material ( 3 ) is provided between the first substrate ( 1 ) and the second substrate ( 4 ), and the first substrate ( 1 ) and second substrate ( 4 ) are glued together by curing the sealant material ( 3 ).

18. The method according to claim 17 , wherein the sealant material ( 3 ) is cured by exposure to photoradiation, wherein the photoradiation is such that it does not cause polymerisation of the polymerisable component A) of the LC medium, and/or the LC medium is protected from the photoradiation for curing the sealant material ( 3 ).

19. The method according to claim 18 , wherein the LC medium is protected from the photoradiation for curing the sealant material ( 3 ) by a photomask.

20. The method according to claim 12 , wherein in step c) a voltage is applied to the first and second electrode.

21. An LC display prepared by a method according to claim 12 .

22. The LC display of claim 21 , which is a PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-posi-VA or PS-TN display.

23. An LC medium comprising components A) and B), wherein

component A) is polymerizable and comprises 0.005 to 0.02% of a first polymerisable compound and 0.2 to 0.3% of a second polymerisable compound, wherein the first polymerisable compound has faster polymerisation speed than the second polymerisable compound, the first polymerisable compound is one or more compounds of formulae F1-F6, and the second polymerisable compound is one or more compounds of formulae S1-S3, and

component B) is a liquid-crystalline and comprises one or more mesogenic or liquid-crystalline compounds

in which

P each, independently, is a polymerisable group,

Sp each, independently, is a spacer group or a single bond,

Sp′ is a spacer group,

L each, independently, is F, Cl, CN or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,

R a , R b each, independently, is -Sp-P, -Sp′(P) 2 , H or one of the meanings given for L,

r is 0, 1, 2, 3 or 4,

s is 0, 1, 2 or 3, and

t is 0, 1 or 2.

24. A process of preparing an LC medium comprising components A) and B) according to claim 23 , comprising mixing component B) with the one or more first and second polymerisable compounds or with polymerisable component A), and optionally with further LC compounds and/or additives.

25. The method of claim 1 , wherein component A) comprises either one or more compounds of formulae F2-F6 and/or one or more compounds of formulae S2-S3.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2018
From: WEEGELS, LEO; CHANG, ROGER; LIN, KY
To: MERCK PATENT GMBH
Reel/Frame 044605/0298 →
Priority Claims (1)
EP 15002093 · Jul 14, 2015 · regional
Continuity (1)
Related Publication 20180201837A1 · Jul 19, 2018