IP Library Granted Patent US 12,617,966
Granted Patent B2
US 12,617,966 · App. 18/031,376 · Granted May 5, 2026

Composition

Inventors: Tadashi Kishimoto (Tokyo, JP); Yuki Hirayama (Tokyo, JP); Julian Burschka (Darmstadt, DE); Teruaki Suzuki (Tokyo, JP); Nils Greinert (Darmstadt, DE); Denis Glozman (Jerusalem, IL); Ehud Shaviv (Jerusalem, IL); Yaron Aviv (Jerusalem, IL); Elizaveta Kossoy (Jerusalem, IL)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C09D11/38B41M5/405C09D11/033C09D11/037C09D11/101C09D11/107C09D11/322C09D11/50G02F1/133617H10K59/38
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Quick Facts
Patent No.
US 12,617,966
App. No.
18/031,376
Granted
May 5, 2026
Kind
B2
Abstract

The present invention relates to a composition comprising at least one light emitting moiety.

Claims (64)

1 . A photo-reactive composition comprising at least one light emitting moiety, which is configured to show a haze value of 15% or less in the liquid state; or is configured to show a haze value of more than 15% in the cured state; or is configured to show the ratio of the haze value in cured state to the haze value in liquid state is more than 1;

wherein the composition comprises

a (meth)acrylate monomer of formula (I)

wherein

R 1 is a hydrogen atom, halogen atom of Cl, Br or F, methyl group, alkyl group, aryl group, alkoxy group, ester group or a carboxylic acid group;

R 2 is a hydrogen atom, halogen atom of Cl, Br or F, methyl group, alkyl group, aryl group, alkoxy group, ester group or a carboxylic acid group;

X 1 is

where “*” on the left side of the formula represents the connecting point to the carbon atom of the end group C═CR 1 of the formula (I) and “*” on the right side represents the connecting point to symbol X 2 of the formula (I);

n is 0 or 1;

X 2

where “*” on the left side of the formula represents the connecting point to symbol X 1 of the formula (I) and “*” on the right side represents the connecting point to the end group C═CR 2 of the formula (I);

m is 0 or 1;

R 3 is a straight alkylene chain or alkoxylene chain having 1 to 25 carbon atoms, a cycloalkane having 3 to 25 carbon atoms or an aryl group having 3 to 25 carbon atoms, which may be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , OS, or CONR a , and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ;

R 4 is a straight alkylene chain or alkoxylene chain having 1 to 25 carbon atoms, a cycloalkane having 3 to 25 carbon atoms or an aryl group having 3 to 25 carbon atoms, which may be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , OS, or CONR a , and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ;

R a is at each occurrence, identically or differently, H, D or an alkyl group having 1 to 20 carbon atoms, cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a hetero aromatic ring system having 5 to 60 carbon atoms, wherein H atoms may be replaced by D, F, Cl, Br or I; wherein two or more adjacent substituents R a may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;

and

a (meth)acrylate monomer of formula (II)

wherein

X 3 is

where “*” on the left side of the formula represents the connecting point to the end group C═CR 5 of the formula (I);

I is 0 or 1;

R 5 is a hydrogen atom, halogen atom of Cl, Br or F, methyl group, alkyl group, aryl group, alkoxy group, ester group or a carboxylic acid group;

R 6 is a straight alkylene chain or alkoxylene chain having 1 to 25 carbon atoms, which may be substituted by one or more radicals R a , and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ;

R 7 is a straight alkylene chain or alkoxylene chain having 1 to 25 carbon atoms, which may be substituted by one or more radicals R a , and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ;

R a is at each occurrence, identically or differently, H, D or an alkyl group having 1 to 20 carbon atoms, cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a hetero aromatic ring system having 5 to 60 carbon atoms, wherein H atoms may be replaced by D, F, Cl, Br or I; and wherein two or more adjacent substituents R a may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another.

2 . The photo-reactive composition comprising at least one light emitting moiety according to claim 1 , which is configured to show a haze value of more than 15% in the cured state.

3 . The photo-reactive composition comprising at least one light emitting moiety according to claim 1 , which is configured to show a haze value of 15% or less in the liquid state.

4 . The photo-reactive composition comprising at least one light emitting moiety according to claim 1 , which is configured to show the ratio of the haze value in cured state to the haze value in liquid state is more than 1.

5 . The composition according to claim 1 , wherein the mixing ratio of the (meth)acrylate monomer of formula (I) to the (meth)acrylate monomer of formula (II) is 1:99 to 99:1.

6 . The composition according to claim 5 , wherein the boiling point of the (meth)acrylate monomer of formula (I) and/or of formula (II) is 250° C. or more.

7 . The composition according to claim 1 , wherein the viscosity of the composition is 35 cP or less at room temperature.

8 . The composition according to claim 1 , wherein said light emitting moiety comprises a ligand.

9 . A layer obtained from the composition according to claim 1 , by curing said composition.

10 . A layer obtained from the composition according to claim 1 , by curing said composition, and containing at least a matrix material, one light emitting moiety, and configured to show a haze value of more than 15%.

11 . A layer obtained from the composition according to claim 1 , further containing

scattering particles, wherein the total amount of the scattering particles is 4 wt % or less based on the total amount of the solid contents of the layer;

or

a 1 st phase and a 2 nd phase, wherein the 1 st phase and the 2 nd phase are different from each other, and the 1 st phase has a plurality of aggregates of the at least one light emitting moiety and higher concentration per unit volume in the at least one light emitting moiety than the 2 nd phase.

12 . The layer according to claim 11 containing at least a matrix material, and wherein the layer is configured to show a haze value of more than 15%.

13 . The layer according to claim 11 containing the at least one light emitting moiety, a matrix material and scattering particles, wherein the total amount of the scattering particles is 4 wt % or less based on the total amount of the solid contents of the layer.

14 . The layer according to claim 11 containing at least a matrix material and a plurality of light emitting moieties, contains a 1 st phase and a 2 nd phase, wherein said 1 st phase and said 2 nd phase are different from each other, and said 1 st phase has a plurality of aggregates of said light emitting moieties and higher concentration per unit volume in the light emitting moieties than the 2 nd phase.

15 . The layer according to claim 11 , having a layer thickness of 1 to 50 μm.

16 . A process of fabricating the layer according to claim 11 , comprising at least the following steps;

I) providing a composition onto a substrate,

which composition is a photo-reactive composition comprising at least one light emitting moiety, which is configured to show a haze value of 15% or less in the liquid state;

or

is configured to show a haze value of more than 15% in the cured state;

or

is configured to show the ratio of the haze value in cured state to the haze value in liquid state is more than 1, and

II) curing the composition.

17 . A color conversion device comprising at least a 1 st pixel partly or fully filled with the layer according to claim 11 comprising at least a matrix material containing a light emitting moiety, and a bank comprising at least a polymer material.

18 . A method for fabricating a color conversion device of claim 17 containing at least the following steps;

Xi) providing a bank composition onto a surface of a supporting medium,

Xii) curing the bank composition,

Xiii) applying photo-patterning to the cured composition to fabricate bank and a patterned pixel region,

Xiv) providing a composition to at least one pixel region,

which composition is a photo-reactive composition comprising at least one light emitting moiety, which is configured to show a haze value of 15% or less in the liquid state;

or

is configured to show a haze value of more than 15% in the cured state;

or

is configured to show the ratio of the haze value in cured state to the haze value in liquid state is more than 1, and

Xv) curing the composition.

19 . An optical device containing at least one functional medium configured to modulate a light or configured to emit light, and the color conversion device of claim 17 .

20 . The composition according to claim 8 , wherein the ligand is an alkyl type ligand having carbon atoms 2 to 25.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2025
From: MERCK PATENT GMBH
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 071620/0871 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: GLOZMAN, DENIS; SHAVIV, EHUD; AVIV, YARON; KOSSOY, ELIZAVETA
To: QLIGHT NANOTECH LTD.,
Reel/Frame 070997/0089 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: BURSCHKA, JULIAN; GREINERT, NILS
To: MERCK ELECTRONICS KGAA
Reel/Frame 070997/0125 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: KISHIMOTO, TADASHI; HIRAYAMA, YUKI; SUZUKI, TERUAKI
To: MERCK ELECTRONICS LTD.
Reel/Frame 070996/0975 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: QLIGHT NANOTECH LTD.,
To: MERCK ELECTRONICS KGAA
Reel/Frame 070997/0519 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: MERCK ELECTRONICS KGAA
To: MERCK PATENT GMBH
Reel/Frame 070997/0589 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: MERCK ELECTRONICS LTD.
To: MERCK ELECTRONICS KGAA
Reel/Frame 070997/0489 →
Priority Claims (2)
EP 20201305 · Oct 12, 2020 · regional
EP 21157392 · Feb 16, 2021 · regional
Continuity (1)
Related Publication 20230392033A1 · Dec 7, 2023
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