Curable composition, method of preparing curable composition, cured material of curable composition, method of preparing cured material, and electronic device including cured material

Patent metadata

Field	Value
Publication number	US-11512159-B2
Application number	US-202017060702-A
Country	US
Kind code	B2
Filing date	Oct 1, 2020
Priority date	Dec 31, 2019
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

A curable composition for an electronic device, includes a curable material; and an oxide-containing complex; wherein the oxide-containing complex includes i) an oxide core and ii) an organic group chemically bound to an atom on a surface of the oxide core, the organic group includes a) a curable group reactable with the curable material and b) a linking group linking the atom on a surface of the oxide core to the curable group, and the oxide core includes an aluminum oxide, a silicon oxide, or a combination thereof.

First claim

What is claimed is:

1. A curable composition comprising:
a curable material; and
an oxide-containing complex;
wherein the oxide-containing complex comprises i) an oxide core and ii) an organic group chemically bound to an atom on a surface of the oxide core,
the organic group comprises a) a curable group reactable with the curable material and b) a linking group linking the atom on a surface of the oxide core to the curable group,
the oxide core comprises an aluminum oxide, a silicon oxide, or a combination thereof, and
wherein the organic group is of Formula 1:

wherein, in Formula 1,
L 1 is:
*—N(R 11 )—*′, *—O—*′, *—S—*′, or *—C(═O)—*′; or
a C 1 -C 60 alkylene group, a C 1 -C 60 oxyalkylene group, a C 6 -C 60 arylene group, or a C 6 -C 60 oxyarylene group, each optionally substituted with deuterium, a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof;
* and *′ each indicate a binding site to an adjacent atom;
R 11 is hydrogen, deuterium, a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, or a biphenyl group;
a1 is an integer from 1 to 10,000, and when a1 is 2 or greater, at least two L 1 (s) are identical to or different from each other;
T 20 is a curable group;
a2 is an integer from 1 to 10, and when a2 is 2 or greater, at least two T 20 (s) are identical to or different from each other; and
T 1 and T 2 are each, independently from one another, hydrogen, deuterium, a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, an oxygen atom bound to a silicon atom in an adjacent linking group, or a binding site to oxygen disposed between the linking group and an adjacent linking group;
wherein in Formula 1, * indicates a binding site to the atom on a surface of the oxide core.

2. The curable composition of claim 1 , wherein the oxide core has a diameter D15 of about 1 nm to about 50 nm.

3. The curable composition of claim 1 , wherein the oxide core has a refractive index of about 1.2 to about 2.5.

4. The curable composition of claim 1 , wherein the T 20 curable group is a group of Formulae 1-2(1) to 1-2(8):

wherein, in Formulae 1-2(1) to 1-2(8),
R 1 to R 5 are each, independently from one another, hydrogen, deuterium, a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, or a biphenyl group; and
* indicates a binding site to the linking group.

5. The curable composition of claim 1 , wherein the oxide core and the organic group in the oxide-containing complex have a weight ratio between about 10:1 to about 1:10.

6. The curable composition of claim 1 , wherein the curable material has a refractive index of about 1.2 to about 2.0.

7. The curable composition of claim 1 , wherein a difference between a refractive index of the curable material and a refractive index of the oxide core is about 0.01 to about 0.5.

8. A method of preparing a curable composition, the method comprising the steps of:
providing an oxide-containing complex including i) an oxide core and ii) an organic group chemically bound to an atom on a surface of the oxide core; and
mixing the oxide-containing complex with a curable material to provide a curable composition including the oxide-containing complex and the curable material;
wherein the organic group comprises a) a curable group reactable with the curable material and b) a linking group linking the atom on a surface of the oxide core to the curable group;
the oxide core comprises an aluminum oxide, a silicon oxide, or a combination thereof; and:
wherein the organic group is of Formula 2:

wherein, in Formula 2,
L 1 is:
*—N(R 11 )—*′, *—O—*′, *—S—*′, or *—C(═O)—*′; or
a C 1 -C 60 alkylene group, a C 1 -C 60 oxyalkylene group, a C 6 -C 60 arylene group, or a C 6 -C 60 oxyarylene group, each optionally substituted with deuterium, a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof;
* and *′ each indicate a binding site to an adjacent atom;
R 11 is hydrogen, deuterium, a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, or a biphenyl group;
a1 is an integer from 1 to 10,000, and when a1 is 2 or greater, at least two L 1 (s) are identical to or different from each other;
T 20 is a curable group;
a2 is an integer from 1 to 10, and when a2 is 2 or greater, at least two T 20 (s) are identical to or different from each other; and
T 11 to T 13 are each, independently from one another, a hydroxyl group or a C 1 -C 20 alkoxy group.

9. A cured material comprising the curable composition of claim 1 .

10. The cured material of claim 9 , wherein the cured material comprises a matrix material derived from the curable material, and the atom on a surface of the oxide core in the oxide-containing complex is chemically bound to the matrix material via i) a residue group derived from a reaction between the curable group in the oxide-containing complex and the curable material, and ii) the linking group in the oxide-containing complex.

11. The cured material of claim 10 , wherein the matrix material comprises an adhesive material.

12. The cured material of claim 10 , wherein the cured material is in the form of a film.

13. The cured material of claim 12 , wherein the film has a thickness of about 0.1 μm to about 700 μm.

14. The cured material of claim 10 , wherein a light transmittance with respect to light having a maximum emission wavelength of 600 nm is about 96% or higher.

15. A method of preparing a cured material comprising the steps of:
providing the curable composition of claim 1 on a substrate; and
curing the curable composition.

16. The method of claim 15 , wherein the step of curing of the curable composition comprises exposing the curable composition to ultraviolet rays.

17. An electronic device comprising the cured material of claim 10 .

18. The electronic device of claim 17 , wherein the electronic device comprises a flexible, foldable, or rollable electronic device.

Assignees

• Samsung Display Co Ltd
• Myongji Univ Industry And Academia Cooperation Foundation

Inventors

• Lee Sanggu
• Lee Junhyup
• Park Yoongook
• Son Intae
• Kim Onnuri
• Byun Hoyun
• Son Younghye

Classifications

• C08F220/1808 Primary

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title

• C08F292/00 Primary

  Macromolecular compounds obtained by polymerising monomers on to inorganic materials · CPC title

• C08K9/06 Primary

  with silicon-containing compounds · CPC title

• C08K3/36

  Silica · CPC title

• C08J2333/08

  Homopolymers or copolymers of acrylic acid esters · CPC title