IP Library › Granted Patent US 10,781,373

Granted Patent B2

US 10,781,373 · App. 15/892,472 · Granted Sep 22, 2020

Photoalignment film forming composition and LCD devices derived therefrom

Inventor: Brian F Knapp (Brecksville, OH)

Assignee: PROMERUS, LLC

C09K19/56 C08G61/08 C09D165/00 G02F1/1339 G02F1/1341 G02F1/133711 G02F1/133788 C08G2261/149 C08G2261/228 C08G2261/3221 C08G2261/3324 C08G2261/90 G02F2202/022 Y10T428/10 Y10T428/1005

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Quick Facts

Patent No.: US 10,781,373
App. No.: 15/892,472
Granted: Sep 22, 2020
Kind: B2

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Abstract

Embodiments in accordance with the present invention provides for the photoalignment layer for liquid crystal displays, a liquid crystal display device using the photoalignment layer and a manufacturing method. The photoalignment layer encompasses polynorbornene (PNB) polymers among other additives. More specifically, embodiments of this invention include a method for the fabrication of a liquid crystal display and the photoalignment layer encompassing the PNB polymers.

Claims (111)

1. A photoalignment layer comprising a polymer, said polymer comprising one or more repeating units distinct from each other and each represented by formula (IA), said repeating unit is derived from a corresponding monomer of formula (I):

wherein:

represents a position at which the bonding takes place with another repeat unit;

Z and Z′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

m is an integer from 0 to 5;

at least one of R 1 , R 2 , R 3 or R 4 is selected from the group consisting of:

wherein:

a is an integer from 1 to 12;

b is an integer from 1 to 4;

R 5 and R 6 are each independently of one another selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C 3 -C 4 )alkyl; or

R 5 and R 6 taken together with the carbon atoms to which they are attached form a substituted or unsubstituted (C 5 -C 8 )cyclic ring;

R 7 is selected from the group consisting of methyl, ethyl, linear or branched (C 3 -C 4 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 4 )alkoxy, (C 6 -C 10 )aryl and (C 6 -C 10 )aryloxy;

the remaining R 1 , R 2 , R 3 and R 4 are the same or different and independently of each other selected from the group consisting of hydrogen, halogen, methyl, ethyl, a fluorinated or perfluorinated methyl or ethyl, linear or branched substituted or unsubstituted (C 3 -C 12 )alkyl, substituted or unsubstituted (C 1 -C 6 )alkoxy, substituted or unsubstituted (C 3 -C 8 )cycloalkyl, substituted or unsubstituted (C 7 -C 12 )bicycloalkyl and substituted or unsubstituted (C 7 -C 12 )tricycloalkyl, substituted or unsubstituted (C 1 -C 12 )alkyl(C 3 -C 8 )cycloalkyl, substituted or unsubstituted (C 6 -C 10 )aryl and substituted or unsubstituted (C 1 -C 12 )alkyl(C 6 -C 16 )aryl where said substituents are selected from halogen, hydroxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 2 -C 6 )alkenyl, (C 3 -C 8 )cycloalkyl, (C 7 -C 12 )bicycloalkyl, (C 1 -C 6 )alkoxy(C 3 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 3 -C 8 )cycloalkyl or (C 1 -C 6 )alkoxy(C 7 -C 12 )bicycloalkyl; and

said photoalignment layer further comprising a photosensitizer of the formula:

2. The photoalignment layer of claim 1 , wherein the polymer further comprising one or more repeating units distinct from each other and each represented by formula (IIA), said repeating unit is derived from a corresponding monomer of formula (II):

wherein

represents a position at which the bonding takes place with another repeat unit;

n is an integer from 0 to 3;

Y and Y′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

R 8 , R 9 , R 10 and R 11 are the same or different and independently of each other selected from the group consisting of hydrogen, methyl, ethyl, a fluorinated or perfluorinated methyl or ethyl, a linear or branched substituted or unsubstituted (C 3 -C 25 )hydrocarbyl group, substituted or unsubstituted (C 1 -C 25 )heterohydrocarbyl group, substituted or unsubstituted (C 3 -C 25 )cyclic hydrocarbyl group, substituted or unsubstituted (C 6 -C 25 )polycyclic hydrocarbyl group, substituted or unsubstituted (C 3 -C 25 )cyclic heterohydrocarbyl group and substituted or unsubstituted (C 6 -C 25 )polycyclic heterohydrocarbyl group.

3. The photoalignment layer of claim 1 , wherein m is 0 or 1.

4. The photoalignment layer of claim 1 , wherein said repeating unit is derived from a monomer of the formula (IA 1 ):

wherein:

a is an integer from 1 to 12; and

R 5 and R 6 are each independently of one another selected from the group consisting of hydrogen, methyl and ethyl.

5. The photoalignment layer of claim 1 , wherein said repeating unit is derived from a monomer selected from the group consisting of:

6. The photoalignment layer of claim 2 , wherein said repeating unit is derived from any one of the monomers selected from the group consisting of:

7. The photoalignment layer of claim 1 , wherein the polymer is a homopolymer derived from a monomer of formula:

8. A method for preparing a photoalignment layer for liquid crystal displays comprising:

coating a surface of a substrate with a composition comprising a polymer, said polymer as defined in claim 1 , and a photosensitizer as defined in claim 1 ; and

exposing the polymer coated substrate to a polarized electromagnetic radiation so as to form a photoaligned polymer layer.

9. The method of claim 8 , wherein said polymer further comprising one or more repeating units distinct from each other and each represented by formula (IIA), said repeating unit is derived from a corresponding monomer of formula (II):

wherein

represents a position at which the bonding takes place with another repeat unit;

n is an integer from 0 to 3;

Y and Y′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

10. A method for preparing a photoalignment layer for liquid crystal displays comprising:

coating separately a surface of a first substrate and a surface of a second substrate with a composition comprising a polymer, said polymer comprising one or more repeating units distinct from each other and each represented by formula (IA), said repeating unit is derived from a corresponding monomer of formula (I):

wherein:

represents a position at which the bonding takes place with another repeat unit;

Z and Z′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

m is an integer from 0 to 5;

at least one of R 1 , R 2 , R 3 or R 4 is selected from the group consisting of:

wherein:

a is an integer from 1 to 12;

b is an integer from 1 to 4;

R 5 and R 6 are each independently of one another selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C 3 -C 4 )alkyl; or

R 5 and R 6 taken together with the carbon atoms to which they are attached form a substituted or unsubstituted (C 5 -C 8 )cyclic ring;

R 7 is selected from the group consisting of methyl, ethyl, line r or branched (C 3 -C 4 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 4 )alkoxy, (C 6 -C 10 )aryl and (C 6 -C 10 )aryloxy;

said composition further comprising a photosensitizer of the formula:

and

exposing separately the polymer coated first substrate and the polymer coated second substrate to a polarized electromagnetic radiation so as to form a photoaligned polymer layer.

11. The method of claim 10 , wherein said polymer further comprising one or more repeating units distinct from each other and each represented by formula (IIA), said repeating unit is derived from a corresponding monomer of formula (II):

wherein

represents a position at which the bonding takes place with another repeat unit;

n is an integer from 0 to 3;

Y and Y′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

12. The method of claim 10 , wherein the polymer is a homopolymer derived from a monomer of formula:

13. The method of claim 10 , wherein said substrate is glass coated with indium-tin oxide.

14. The method of claim 10 , which further comprises:

depositing along the long edges of the polymer coated first substrate a strip of glass beads and an adhesive layer;

placing the second polymer coated substrate over the first substrate such that the second substrate is directly in contact with the adhesive layer on the long edges, and the polymer coated surface of first substrate and the polymer coated surface of the second substrate are directly facing each other so as to form a gap between said polymer coated first substrate and said polymer coated second substrate;

masking the gap between said first substrate and said second substrate; and

exposing the first and second substrates to an electromagnetic radiation in order to cure the adhesive and to fix the gap between the first and the second substrate.

15. The method of claim 14 , which further comprises filling the gap between the first and the second substrate with a liquid crystal.

16. The method of claim 15 , wherein the liquid crystal is filled in such a manner that the liquid crystal is placed parallel to the photoaligned polymeric layer.

17. The method of claim 15 , wherein the liquid crystal is filled at a temperature from 40° C. to 60° C.

18. A method for preparing a photoalignment layer for liquid crystal displays comprising:

wherein:

represents a position at which the bonding takes place with another repeat unit;

Z and Z′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

m is an integer from 0 to 5;

at least one of R 1 , R 2 , R 3 or R 4 is selected from the group consisting of:

wherein:

a is an integer from 1 to 12;

b is an integer from 1 to 4;

R 5 and R 6 are each independently of one another selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C 3 -C 4 )alkyl; or

R 5 and R 6 taken together with the carbon atoms to which they are attached form a substituted or unsubstituted (C 5 -C 8 )cyclic ring;

R 7 is selected from the group consisting of methyl, ethyl, linear or branched (C 3 -C 4 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 4 )alkoxy, (C 6 -C 10 )aryl and (C 6 -C 10 )aryloxy;

said composition further comprising a photosensitizer of the formula:

and

exposing separately the polymer coated first substrate and the polymer coated second substrate to a polarized electromagnetic radiation so as to form a photoaligned polymer layer;

depositing along the long edges of the polymer coated first substrate a strip of glass beads and an adhesive layer;

masking the gap between said first substrate and said second substrate; and

exposing the first and second substrates to an electromagnetic radiation in order to cure the adhesive and to fix the gap between the first and the second substrate; and

filling the gap between the first and the second substrate with a liquid crystal in such a manner that the liquid crystal is placed parallel to the photoaligned polymeric layer.

19. A liquid crystal display device comprising:

a first and a second substrate coated with a photoaligned polymer layer, wherein said photoaligned polymer comprising one or more repeating units distinct from each other and each represented by formula (IA), said repeating unit is derived from a corresponding monomer of formula (I):

wherein:

represents a position at which the bonding takes place with another repeat unit;

Z and Z′ are the same or different and independently of each other selected from the group consisting of —CH 2 —, —CH 2 —CH 2 — and —O—;

m is an integer from 0 to 5;

at least one of R 1 , R 2 , R 3 or R 4 is selected from the group consisting of:

wherein:

a is an integer from 1 to 12;

b is an integer from 1 to 4;

R 5 and R 6 are each independently of one another selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C 3 -C 4 )alkyl; or

R 5 and R 6 taken together with the carbon atoms to which they are attached form a substituted or unsubstituted (C 5 -C 8 )cyclic ring;

R 7 is selected from the group consisting of methyl, ethyl, linear or branched (C 3 -C 4 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 4 )alkoxy, (C 6 -C 10 )aryl and (C 6 -C 10 )aryloxy;

said photoaligned polymer layer further comprising a photosensitizer of the formula:

and

a liquid crystal disposed between, said first and second substrate directly in contact with said photoaligned polymer layers.

20. The liquid crystal display device of claim 19 , wherein the polymer is a homopolymer derived from a monomer of formula:

21. The liquid crystal display device of claim 19 , wherein the thickness of said first and second photoaligned polymer layer is at least 3 nm.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2024

From: PROMERUS, LLC

To: SUMITOMO BAKELITE CO., LTD.

Reel/Frame 069364/0733 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2018

From: KNAPP, BRIAN

To: PROMERUS, LLC

Reel/Frame 044942/0304 →

Continuity (2)

Provisional Application 62456747 · Feb 9, 2017

Related Publication 20180223190A1 · Aug 9, 2018