IP Library Granted Patent US 9,811,192
Granted Patent B2
US 9,811,192 · App. 14/951,328 · Granted Nov 7, 2017

Composition for window film, flexible window film manufactured using the same and flexible display including the same

Inventors: Chang Soo Woo (Uiwang-si, KR); Kyoung Ku Kang (Uiwang-si, KR); Min Hye Kim (Uiwang-si, KR); Ji Sun Im (Uiwang-si, KR); Seung Woo Jang (Uiwang-si, KR); Dong Il Han (Uiwang-si, KR)
Assignee: SAMSUNG SDI CO., LTD.
G06F3/0412B32B27/283C08G77/14C09D183/06G02B1/04G02B1/14G02B5/3033G06F1/1652G06F3/044B32B2307/40B32B2307/536B32B2307/71C08L2312/06G06F2203/04102
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Quick Facts
Patent No.
US 9,811,192
App. No.
14/951,328
Granted
Nov 7, 2017
Kind
B2
Abstract

A composition for a window film includes a siloxane resin represented by Formula 1, 4 or 7, or a mixture thereof, and an initiator. A flexible window film is manufactured using the same, and has a pencil hardness of about 7H or higher, a radius of curvature of about 5.0 mm or less, and a difference in yellow index before and after irradiation (ΔY.I.) of about 5.0 or less. A flexible display includes the flexible window film. (R 1 SiO 3/2 ) x (R 2 R 3 SiO 2/2 ) y   Formula 1 (R 1 SiO 3/2 ) x (R 9 SiO 3/2 ) z   Formula 4 (R 1 SiO 3/2 ) x (R 2 R 3 SiO 2/2 ) y (R 9 SiO 3/2 ) z   Formula 7

Claims (147)

1. A composition for a window film, comprising:

a siloxane resin represented by Formula, 4 or 7, or a mixture thereof; and

an initiator:

(R 1 SiO 3/2 ) x (R 9 SiO 3/2 ) z   Formula 4

wherein:

R 1 is a crosslinkable functional group;

R 9 is a UV absorbing functional group, or a UV absorbing functional group-containing group;

0<x<1;

0<z<1; and

x+z=1;

(R 1 SiO 3/2 ) x (R 2 R 3 SiO 2/2 ) y (R 9 SiO 3/2 ) z   Formula 7

wherein:

R 1 is a crosslinkable functional group;

R 2 and R 3 are each independently hydrogen, a crosslinkable functional group, an unsubstituted or substituted C 1 to C 20 alkyl group, or an unsubstituted or substituted C 5 to C 20 cycloalkyl group;

at least one of R 2 and R 3 is an unsubstituted or substituted C 1 to C 20 alkyl group;

R 9 is a UV absorbing functional group, or a UV absorbing functional group-containing group and R 9 in Formula 4 and Formula 7 is an unsubstituted or substituted hydroxybenzophenone group, an unsubstituted or substituted hydroxyphenyltriazine croup, or a group represented by Formula 5,

*—(R x ) n1 -M-(R x ) n2 —R y   Formula 5

wherein in Formula 5:

* represents a binding site for Si, R x is an unsubstituted or substituted C 1 to C 20 alkylene group, an unsubstituted or substituted C 1 to C 20 alkyleneoxy group, an unsubstituted or substituted C 1 to C 20 alkylene group having a urethane bond therein or at an end thereof, an unsubstituted or substituted C 1 to C 20 alkyleneoxy group having a urethane bond therein or at an end thereof, an unsubstituted or substituted C 6 to C 20 arylene group, or a combination thereof;

n1 and n2 are each independently 0 or 1;

M is a single bond, oxygen (O), sulfur (S), NR where R is hydrogen or a C 1 to C 20 alkyl group, —CONH—, —OCONH—, —C═O—, or —C═S—;

R y is an unsubstituted or substituted benzotriazole group, an unsubstituted or substituted benzophenone group, an unsubstituted or substituted hydroxybenzophenone group, an unsubstituted or substituted triazine group, an unsubstituted or substituted salicylate group, an unsubstituted or substituted cyanoacrylate group, an unsubstituted or substituted oxanilide group, an unsubstituted or substituted hydroxyphenyltriazine group, an unsubstituted or substituted hydroxyphenylbenzotriazole group, or an unsubstituted or substituted hydroxyphenylbenzophenone group;

0<x<1;

0<y<1;

0<z<1; and

x+y+z=1.

2. The composition for a window film according to claim 1 , wherein the siloxane resin comprises a compound represented by any one of Formulae 4-1 to 4-12:

(EcSiO 3/2 ) x (RaSiO 3/2 ) z   Formula 4-1

(EcSiO 3/2 ) x (RbSiO 3/2 ) z   Formula 4-2

(EcSiO 3/2 ) x (RcSiO 3/2 ) z   Formula 4-3

(EcSiO 3/2 ) x (RdSiO 3/2 ) z   Formula 4-4

(GpSiO 3/2 ) x (RaSiO 3/2 ) z   Formula 4-5

(GpSiO 3/2 ) x (RbSiO 3/2 ) z   Formula 4-6

(GpSiO 3/2 ) x (RcSiO 3/2 ) z   Formula 4-7

(GpSiO 3/2 ) x (RdSiO 3/2 ) z   Formula 4-8

(OpSiO 3/2 ) x (RaSiO 3/2 ) z   Formula 4-9

(OpSiO 3/2 ) x (RbSiO 3/2 ) z   Formula 4-10

(OpSiO 3/2 ) x (RcSiO 3/2 ) z   Formula 4-11

(OpSiO 3/2 ) x (RdSiO 3/2 ) z   Formula 4-12

wherein:

Ec is a (3,4-epoxycyclohexyl)ethyl group;

Gp is a 3-glycidoxypropyl group;

Op is a 3-oxetanylpropyl group;

Ra is a group represented by Formula i);

Rb is a group represented by Formula ii);

Rc is a group represented by Formula iii);

Rd is a group represented by Formula iv);

0<x<1;

0<z<1; and

x+z=1;

wherein * represents a binding site.

3. The composition for a window film according to claim 1 , wherein the siloxane resin comprises a compound represented by any one of Formulae 7-1 to 7-36:

(EcSiO 3/2 ) x (EcMeSiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-1

(EcSiO 3/2 ) x (EcMeSiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-2

(EcSiO 3/2 ) x (EcMeSiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-3

(EcSiO 3/2 ) x (EcMeSiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-4

(EcSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-5

(EcSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-6

(EcSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-7

(EcSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-8

(EcSiO 3/2 ) x (GpMeSiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-9

(EcSiO 3/2 ) x (GpMeSiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-10

(EcSiO 3/2 ) x (GpMeSiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-11

(EcSiO 3/2 ) x (GpMeSiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-12

(GpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-13

(GpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-14

(GpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-15

(GpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-16

(GpSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-17

(GpSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-18

(GpSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-19

(GpSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-20

(GpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-21

(GpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-22

(GpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-23

(GpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-24

(OpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-25

(OpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-26

(OpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-27

(OpSiO 3/2 ) x (EcMeSiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-28

(OpSiO 3/2 ) X ((Me) 2 SiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-29

(OpSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-30

(OpSiO 3/2 ) X ((Me) 2 SiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-31

(OpSiO 3/2 ) x ((Me) 2 SiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-32

(OpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RaSiO 3/2 ) z   Formula 7-33

(OpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RbSiO 3/2 ) z   Formula 7-34

(OpSiO 3/2 ) X (GpMeSiO 2/2 ) y (RcSiO 3/2 ) z   Formula 7-35

(OpSiO 3/2 ) x (GpMeSiO 2/2 ) y (RdSiO 3/2 ) z   Formula 7-36

wherein:

Ec is a (3,4-epoxycyclohexyl)ethyl group;

Me is a methyl group;

Gp is a 3-glycidoxypropyl group;

Op is a 3-oxetanylpropyl group;

Ra is a group represented by Formula i);

Rb is a group represented by Formula ii);

Rc is a group represented by Formula iii);

Rd is a group represented by Formula iv);

0<x<1;

0<y<1;

0<z<1; and

x+y+z=1;

wherein * represents a binding site.

4. The composition for a window film according to claim 1 , further comprising a crosslinking agent.

5. The composition for a window film according to claim 4 , wherein the crosslinking agent comprises at least one of a non-cyclic aliphatic epoxy monomer, a cyclic aliphatic epoxy monomer, an aromatic epoxy monomer, a hydrogenated aromatic epoxy monomer, or an oxetane monomer.

6. A flexible window film, comprising:

a base layer; and

a coating layer on a surface of the base layer,

wherein the flexible window film has a pencil hardness of about 7H or higher, a radius of curvature of about 5.0 mm or less, and a difference in yellow index before and after irradiation (ΔY.I.) of about 5.0 or less, and the coating layer is formed from a composition for a window film the composition for a window film comprising:

a siloxane resin represented by Formula, 4 or 7, or a mixture thereof; and

an initiator:

(R 1 SiO 3/2 ) x (R 9 SiO 3/2 ) z   Formula 4

wherein:

R 1 is a crosslinkable functional group;

R 9 is a UV absorbing functional group, or a UV absorbing functional group-containing group;

0<x<1;

0<z<1; and

x+z=1;

(R 1 SiO 3/2 ) x (R 2 R 3 SiO 2/2 ) y (R 9 SiO 3/2 ) z   Formula 7

wherein:

R 1 is a crosslinkable functional group;

R 2 and R 3 are each independently hydrogen, a crosslinkable functional group, an unsubstituted or substituted C 1 to C 20 alkyl group, or an unsubstituted or substituted C 5 to C 20 cycloalkyl group;

at least one of R 2 and R 3 is an unsubstituted or substituted C 1 to C 20 alkyl group;

R 9 is a UV absorbing functional group, or a UV absorbing functional group-containing group;

0<x<1;

0<y<1;

0<z<1; and

x+y+z=1.

7. The flexible window film according to claim 6 , further comprising:

an adhesive layer on an other surface of the base layer.

8. A flexible display comprising the flexible window film according to claim 6 .

9. The flexible display according to claim 8 , comprising:

a display unit;

an adhesive layer on the display unit;

a polarizing plate on the adhesive layer;

a touchscreen panel on the polarizing plate; and

the flexible window film on the touchscreen panel.

10. The flexible display according to claim 8 , comprising:

a display unit;

a touchscreen panel on the display unit;

a polarizing plate on the touchscreen panel; and

the flexible window film on the polarizing plate.

11. The flexible display according to claim 8 , comprising:

a display unit;

an adhesive layer on the display unit; and

the flexible window film on the adhesive layer.

12. The flexible display according to claim 11 , further comprising:

a polarizing plate on an upper or lower side of the display unit.

Assignments (3)
LICENSE Recorded Aug 12, 2021
From: SOLIP TECH CO., LTD.
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 057178/0682 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2021
From: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
To: SOLIP TECH CO., LTD.
Reel/Frame 056611/0890 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2016
From: WOO, CHANG SOO; KANG, KYOUNG KU; KIM, MIN HYE; IM, JI SUN; JANG, SEUNG WOO; HAN, DONG IL
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 037600/0360 →
Priority Claims (1)
KR 10-2014-0169211 · Nov 28, 2014 · national
Continuity (1)
Related Publication 20160154436A1 · Jun 2, 2016