IP Library Granted Patent US 11,314,007
Granted Patent B2
US 11,314,007 · App. 16/629,545 · Granted Apr 26, 2022

Circularly polarizing plate

Inventors: Sun Kug Kim (Daejeon, KR); Moon Soo Park (Daejeon, KR); Sin Young Kim (Daejeon, KR); Hyuk Yoon (Daejeon, KR); Eun Soo Huh (Daejeon, KR); Jong Hyun Jung (Daejeon, KR)
Assignee: LG CHEM, LTD.
G02B5/305C09K19/24C09K19/3497G02B5/3016H01L51/5293C09K2019/0448C09K2323/03C09K2323/031C09K2323/035H01L51/5281
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Quick Facts
Patent No.
US 11,314,007
App. No.
16/629,545
Granted
Apr 26, 2022
Kind
B2
Abstract

Provided is a circularly polarizing plate and a display device that includes the circularly polarizing plate. The circularly polarizing plate can be applied to a display device such as an organic light emitting display device to minimize blocking of light in the visible light region affecting image quality while blocking harmful ultraviolet rays appropriately and also has excellent durability.

Claims (109)

1. A circularly polarizing plate comprising

a polarizer; and

a phase difference layer formed on one side of the polarizer,

wherein the phase difference layer comprises a polymerized unit of a normal dispersion polymerizable liquid crystal compound and a polymerization unit of a reverse dispersion polymerizable liquid crystal compound in a ratio of 5:95 to 10:90 (normal: reverse),

the phase difference layer has ultraviolet absorptivity that transmittance for light having a wavelength of 385 nm is 3% or less and transmittance of 2% or more for light having a wavelength of 390 nm,

the phase difference layer has an absolute value of a phase difference change ratio according to Equation A below of 17% or less,

wherein the normal dispersion polymerizable liquid crystal compound is a compound of Formula 6, and

wherein the reverse dispersion polymerizable liquid crystal compound is a compound of Formula 1:

Phase difference change ratio=100×( Ra−Ri )/ Ri   [Equation A]

wherein, Ri is the initial in-plane phase difference of the phase difference layer for a wavelength of 550 nm, and Ra is the in-plane phase difference of the phase difference layer for a wavelength of 550 nm after an endurance condition, where the endurance condition is a condition that the phase difference layer is allowed to stand at a temperature of 85° C. for 50 hours or more,

wherein:

A is a single bond, —C(═O)O— or —OC(═O)—;

R 2 and R 3 or R 3 and R 4 are bonded to each other to constitute a benzene ring substituted with -L-A-P, where L is —OC(═O)O—, A is an alkylene group and P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group; any one of R 7 to R 9 is Formula 7 below; the remaining substituents are each independently hydrogen, halogen, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group or a nitro group;

wherein:

B is a single bond, —C(═O)O— or —OC(═O)—; and

two neighboring substituents of R 11 to R 15 are bonded to each other to constitute a benzene ring substituted with -L-A-P, where L is —OC(═O)O—, A is an alkylene group and P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group; the remaining substituents are each independently hydrogen, halogen, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group or a nitro group;

wherein:

R 1 is a substituent of Formula 2 or 3 below; and

R 2 to R 6 are each independently hydrogen, an alkyl group, an alkoxy group, a cyano group, a substituent of Formula 4 below or a substituent of Formula 5 below where at least two or more of R 2 to R 6 are substituents of Formula 4 below or substituents of Formula 5 below:

-A 1 -L 1 -Cyc-A 2 -L 2 -P   [Formula 2]

wherein:

A 1 and A 2 are each independently an oxygen atom or a single bond;

L 1 and L 2 are each independently —C(═O)—O—, —O—C(═O)— or an alkylene group;

Cyc is an arylene group or a cycloalkylene group; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group;

wherein:

L 3 and L 4 are each an alkylene group;

n is a number in a range of 1 to 4; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group or a hydrogen atom;

-A 3 -L 5 -Cyc-A 4 -L 6 -P   [Formula 4]

wherein:

A 3 and A 4 are an oxygen atom, an alkylene group or a single bond;

L 5 and L 6 are each independently —C(═O)—O—, —O—C(═O)— or an alkylene group;

Cyc is an arylene group; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group;

-A 5 -L 7 -Cy 1 -A 6 -L 8 -Cy 2 -A 7 -L 9 -P   [Formula 5]

wherein:

A 5 , A 6 and A 7 are each independently an oxygen atom or a single bond;

L 7 , L 8 and L 9 are each independently —C(═O)—O—, —O—C(═O) — or an alkylene group;

Cy1is a cycloalkylene group;

Cy2 is an arylene group; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group.

2. A circularly polarizing plate comprising

a polarizer; and

a phase difference layer formed on one side of the polarizer,

wherein the phase difference layer comprises a polymerized unit of a normal dispersion polymerizable liquid crystal compound and a polymerization unit of a reverse dispersion polymerizable liquid crystal compound in a ratio of 5:95 to 10:90 (normal: reverse), and

the phase difference layer has ultraviolet absorptivity that transmittance for light having a wavelength of 385 nm is 3% or less, and transmittance of 2% or more for light having a wavelength of 390 nm, and does not comprise an ultraviolet absorber having a maximum absorption wavelength in a range of 385 nm to 400 nm,

wherein the normal dispersion polymerizable liquid crystal compound is a compound of Formula 6, and

wherein the reverse dispersion polymerizable liquid crystal compound is a compound of Formula 1:

wherein:

A is a single bond, —C(═O)O— or —OC(═O)—;

R 2 and R 3 or R 3 and R 4 are bonded to each other to constitute a benzene ring substituted with -L-A-P, where L is —OC(═O)O—, A is an alkylene group and P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group; any one of R 7 to R 9 is Formula 7 below; the remaining substituents are each independently hydrogen, halogen, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group or a nitro group;

wherein:

B is a single bond, —C(═O)O— or —OC(═O)—; and

two neighboring substituents of R 11 to R 15 are bonded to each other to constitute a benzene ring substituted with -L-A-P, where L is —OC(═O)O—, A is an alkylene group and P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group, and the remaining substituents are each independently hydrogen, halogen, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group or a nitro group;

wherein:

R 1 is a substituent of Formula 2 or 3 below; and

R 2 to R 6 are each independently hydrogen, an alkyl group, an alkoxy group, a cyano group, a substituent of Formula 4 below or a substituent of Formula 5 below where at least two or more of R 2 to R 6 are substituents of Formula 4 below or substituents of Formula 5 below:

-A 1 -L 1 -Cyc-A 2 -L 2 -P   [Formula 2]

wherein:

A 1 and A 2 are each independently an oxygen atom or a single bond;

L 1 and L 2 are each independently —C(═O)—O—, —O—C(═O)— or an alkylene group;

Cyc is an arylene group or a cycloalkylene group; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group;

wherein:

L 3 and L 4 are each an alkylene group;

n is a number in a range of 1 to 4; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group or a hydrogen atom;

-A 3 -L 5 -Cyc-A 4 -L 6 -P   [Formula 4]

wherein:

A 3 and A 4 are an oxygen atom, an alkylene group or a single bond;

L 5 and L 6 are each independently —C(═O)—O—, —O—C(═O)— or an alkylene group;

Cyc is an arylene group; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group;

-A 5 -L 7 -Cy 1 -A 6 -L 8 -Cy 2 -A 7 -L 9 -P   [Formula 5]

wherein:

A 5 , A 6 and A 7 are each independently an oxygen atom or a single bond;

L 7 , L 8 and L 9 are each independently —C(═O)—O—, —O—C(═O)— or an alkylene group;

Cy1 is a cycloalkylene group;

Cy2 is an arylene group; and

P is an acryloyl group, a methacryloyl group, an acryloyloxy group or a methacryloyloxy group.

3. The circularly polarizing plate according to claim 1 , wherein the phase difference layer has a transmittance of 25% or less for light having a wavelength of 395 nm.

4. The circularly polarizing plate according to claim 1 , wherein the phase difference layer has a transmittance of 40% or less for light having a wavelength of 400 nm.

5. The circularly polarizing plate according to claim 1 , wherein the phase difference layer comprises 40 wt % or more of polymerized units of the reverse wavelength polymerizable liquid crystal compound in polymerized units of the entire polymerizable liquid crystal compound.

6. The circularly polarizing plate according to claim 1 , wherein the phase difference layer comprises 30 wt % or more of polymerized units of the polymerizable liquid crystal compound having tri-functionality or more in polymerized units of the entire polymerizable liquid crystal compound.

7. The circularly polarizing plate according to claim 1 , further comprising an optical film laminated on an opposite surface of the polarizer facing the phase difference layer and having a planar phase difference for light having a wavelength of 550 nm in a range of 90 nm to 300 nm.

8. The circularly polarizing plate according to claim 1 , further comprising an optical film present between the polarizer and the phase difference layer, and having a planar phase difference of 10 nm or less for light having a wavelength of 550 nm and a thickness direction phase difference for light having a wavelength of 550 nm in a range of 40 nm to 400 nm.

9. The circularly polarizing plate according to claim 1 , further comprising an optical film present on the lower part of the phase difference layer and having a thickness direction phase difference in a range of 10 to 400 nm.

10. An organic light emitting display device, comprising:

a reflective electrode;

a transparent electrode;

an organic layer interposed between the reflective electrode and the transparent electrode and having a light emitting layer; and

the circularly polarizing plate of claim 1 ,

wherein:

the circularly polarizing plate is present outside the reflective or transparent electrode, and

the phase difference layer is disposed closer to the reflective or transparent electrode than the polarizer.

11. An organic light emitting display device, comprising:

a reflective electrode;

a transparent electrode;

an organic layer interposed between the reflective electrode and the transparent electrode and having a light emitting layer; and

the circularly polarizing plate of claim 2 ,

wherein:

the circularly polarizing plate is present outside the reflective or transparent electrode, and

the phase difference layer is disposed closer to the reflective or transparent electrode than the polarizer.

12. The circularly polarizing plate according to claim 2 , wherein the phase difference layer has a transmittance of 25% or less for light having a wavelength of 395 nm.

13. The circularly polarizing plate according to claim 2 , wherein the phase difference layer has a transmittance of 40% or less for light having a wavelength of 400 nm.

14. The circularly polarizing plate according to claim 2 , further comprising an optical film laminated on an opposite surface of the polarizer facing the phase difference layer and having a planar phase difference for light having a wavelength of 550 nm in a range of 90 nm to 300 nm.

15. The circularly polarizing plate according to claim 2 , further comprising an optical film present between the polarizer and the phase difference layer, and having a planar phase difference of 10 nm or less for light having a wavelength of 550 nm and a thickness direction phase difference for light having a wavelength of 550 nm in a range of 40 nm to 400 nm.

16. The circularly polarizing plate according to claim 2 , further comprising an optical film present on the lower part of the phase difference layer and having a thickness direction phase difference in a range of 10 to 400 nm.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2025
From: LG CHEM LTD.
To: SHANJIN OPTOELECTRONICS (SUZHOU) CO., LTD.
Reel/Frame 070629/0273 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2020
From: KIM, SUN KUG; PARK, MOON SOO; KIM, SIN YOUNG; YOON, HYUK; HUH, EUN SOO; JUNG, JONG HYUN
To: LG CHEM, LTD.
Reel/Frame 051456/0363 →
Priority Claims (1)
KR 10-2017-0087122 · Jul 10, 2017 · national
Continuity (1)
Related Publication 20210011210A1 · Jan 14, 2021