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US-12617966-B2 - Composition

US12617966B2US 12617966 B2US12617966 B2US 12617966B2US-12617966-B2

Abstract

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

Inventors

  • Tadashi Kishimoto
  • Yuki Hirayama
  • Julian Burschka
  • Teruaki Suzuki
  • Nils Greinert
  • Denis GLOZMAN
  • Ehud SHAVIV
  • Yaron Aviv
  • Elizaveta KOSSOY

Assignees

  • SAMSUNG ELECTRONICS CO., LTD.

Dates

Publication Date
20260505
Application Date
20211011
Priority Date
20201012

Claims (20)

  1. 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. 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. 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. 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. 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. 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. 7 . The composition according to claim 1 , wherein the viscosity of the composition is 35 cP or less at room temperature.
  8. 8 . The composition according to claim 1 , wherein said light emitting moiety comprises a ligand.
  9. 9 . A layer obtained from the composition according to claim 1 , by curing said composition.
  10. 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. 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. 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. 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. 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. 15 . The layer according to claim 11 , having a layer thickness of 1 to 50 μm.
  16. 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. 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. 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. 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. 20 . The composition according to claim 8 , wherein the ligand is an alkyl type ligand having carbon atoms 2 to 25.

Description

FIELD OF THE INVENTION The present invention relates to a photo-reactive composition comprising at least one light emitting moiety, a layer, a color conversion device, process for fabricating a color conversion device, an optical device containing at least one color conversion device, method for fabricating a color conversion device and use of a composition. BACKGROUND ART WO 2017/054898 A1 describes a composition comprising red emission type nanocrystals, wetting and dispersing agent, propylene glycol monomethyl ether acetate as a solvent, an acryl polymer mixture including an acrylic unit including an acid group and a silane modified acrylic unit. WO 2019/002239 A1 discloses a composition comprising a semiconducting light emitting nanoparticles, a polymer and a (meth)acrylate such as 1.4. cyclohexanedimethanol-monoacrylate having high viscosity around 90 cp. PATENT LITERATURE 1. WO 2017/054898 A12. WO 2019/002239 A1 SUMMARY OF THE INVENTION However, the inventors newly have found that there are still one or more of considerable problems for which improvement is desired, as listed below. TiO2 particles that are typically used as scattering particles in QD inks have a rather high density and combined with the rather large particle size needed for efficient visible light scattering, sedimentation is a common issue. Sedimentation, often caused by aggregation, can lead to issues during ink-jet printing. Hence it is desired to develop an ink that requires less amount of TiO2 or scattering particles in general to achieve high EQE, or better no TiO2 or scattering particles in general to achieve high EQE. Additionally, the addition of TiO2 leads to a significant increase in viscosity. Therefore, it is desired to provide a QD ink with less or without TiO2 or scattering particles in general which would therefore provide more flexibility for the ink design and selection and concentration of the other ink components. The benefit of this invention is achieving higher EQE and lower BL for a QD ink without scattering particles or less amount of scattering particles compared to a reference ink, achieving higher haze value of a cured QD ink without scattering particles or less amount of scattering particles compared to a reference ink, and achieving higher haze value of a cured QD ink without scattering particles or less amount of scattering particles compared to a reference ink and higher EQE at the same time possibly realizing lower blue leakage at the same time, improved optical properties of bank, improved compatibility between a bank and a composition containing a light emitting moiety (e.g. QD ink), improved wetting properties and chemical stability towards a composition containing a light emitting moiety, less degradation of the bank structure upon bringing the composition containing a light emitting moiety into contact with the bank,Such degradation may be (partial or complete) dissolution of the bank structure by the QD ink formulation, delamination of the bank structure and/or intermixing of the bank and the QD ink. This would lead to a loss of integrity of the bank structure and/or a loss of the well-defined pixel structure. realizing adequate chemical resistance of the bank so that no degradation is observed upon filling the wells of the bank structure with QD Ink, realizing low curing temperature (e.g. 100° C.) properties of the bank,providing a bank having high resolution and/or excellent light shielding properties. Providing a bank composition configured to be developed even with a low-concentration alkaline developer other than an organic developer and is excellent also in environmental properties,improved homogeneous dispersion of semiconducting light emitting nanoparticles in the composition, improved homogeneous dispersion of scattering particles in the composition, preferably improved homogeneous dispersion of both semiconducting light emitting nanoparticles and scattering particles, more preferably improved homogeneous dispersion of semiconducting light emitting nanoparticles and/or scattering particles without solvent; composition having lower viscosity suitable for inkjet printing, preferably a composition which can keep lower viscosity even if it is mixed with high loading of semiconducting light emitting nanoparticles and/or scattering particles, even more preferably without solvent; composition having lower vaper pressure for large area uniform printing; improved QY and/or EQE of semiconducting light emitting nanoparticles in the composition, improved QY and/or EQE of semiconducting light emitting nanoparticles after printing; improved thermal stability; easy printing without clogging at a printing nozzle; easy handling of the composition, improved printing properties; simple fabrication process; improved absorbance of blue light; improved solidity of a later made from the composition after inkjet printing. The inventors aimed to solve one or more of the above-mentioned problems. Then it is found