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KR-102962013-B1 - CURABLE COMPOSITION, CURED LAYER USING THE COMPOSITION AND DISPLAY DEVICE INCLUDING THE CURED LAYER

KR102962013B1KR 102962013 B1KR102962013 B1KR 102962013B1KR-102962013-B1

Abstract

(A) a quantum dot; and (B) a polymerizable compound, wherein the polymerizable compound comprises a compound containing a structural unit represented by the following chemical formula 1, a curable composition, a curable film prepared using the curable composition, and a display device including the curable film are provided. [Chemical Formula 1] (In the above Chemical Formula 1, each substituent is as defined in the specification.)

Inventors

  • 강용희
  • 김소현
  • 임지현
  • 김철규
  • 이범진

Assignees

  • 삼성에스디아이 주식회사

Dates

Publication Date
20260507
Application Date
20240604

Claims (19)

  1. (A) Quantum dots; and (B) Polymerizable compounds Includes, The above polymerizable compound is a curable composition comprising a compound containing a structural unit represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is a sulfur atom or a single bond, and R1 is a monovalent functional group containing a carbon-carbon double bond, and R2 and R3 are each independently a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, and L1 is a substituted or unsubstituted C1 to C20 alkylene group, and L2 and L3 are each independently single-bonded, substituted, or unsubstituted C1 to C20 alkylene groups, and n and m are each independently 1 to 100, and p is an integer from 0 to 20.
  2. In paragraph 1, The above n : m is a curable composition having an equivalent ratio of 1 : 1 to 1 : 9.
  3. In paragraph 1, The above R1 is a monovalent cyclic functional group in which a carbon-carbon double bond is included in the ring structure, or a curable composition represented by the following chemical formula R-1: [Chemical Formula R-1] In the above chemical formula R-1, R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group, and L a is a single bond, an ester group (-C(=O)O- or -OC(=O)-), a substituted or unsubstituted C3 to C20 cycloalkylene group, or a fused ring of C3 to C20 cycloalkane rings.
  4. In Paragraph 3, A curable composition in which the monovalent cyclic functional group having a carbon-carbon double bond in a ring structure is a monovalent fused cyclic functional group having a carbon-carbon double bond in a fused ring structure.
  5. In paragraph 1, The above polymerizable compound is a curable composition further comprising a compound represented by the following chemical formula 2. [Chemical Formula 2] In the above chemical formula 2, R6 and R7 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group, and L6 and L8 are each independently single-bonded, substituted, or unsubstituted C1 to C10 alkylene groups, and L 7 is a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or an ether group (-O-).
  6. In paragraph 5, The compound represented by the above chemical formula 2 is a curable composition represented by the following chemical formula 2-1 or 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2]
  7. In paragraph 5, A curable composition in which the compound represented by Chemical Formula 2 is included in a smaller amount than the compound containing the structural unit represented by Chemical Formula 1.
  8. In paragraph 1, The above curable composition is a solvent-free curable composition.
  9. In paragraph 8, The above solvent-free curable composition, with respect to the total amount of the above solvent-free curable composition, 5% to 60% by weight of the above quantum dots; and 40% to 95% by weight of the above polymerizable compound A solvent-free curable composition comprising
  10. In paragraph 1, The above curable composition is a curable composition further comprising a polymerization initiator, a light diffusing agent, a polymerization inhibitor, or a combination thereof.
  11. In Paragraph 10, The light diffusing agent is a curable composition comprising barium sulfate, calcium carbonate, titanium dioxide, zirconia, or a combination thereof.
  12. In paragraph 1, The above curable composition is a curable composition further comprising a solvent.
  13. In Paragraph 12, The above curable composition comprises, based on the total weight of the above curable composition, 1% to 40% by weight of the quantum dots; 1% to 20% by weight of the polymerizable compound; and 40% to 80% by weight of the solvent.
  14. In paragraph 1, The above curable composition further comprises malonic acid; 3-amino-1,2-propanediol; a silane-based coupling agent; a leveling agent; a fluorine-based surfactant; or a combination thereof.
  15. In paragraph 1, The above quantum dots are a curable composition comprising a non-cadmium light-emitting material.
  16. In paragraph 15, The above quantum dots are a curable composition having an InP/ZnS core/shell structure or an InP/ZeSe/ZnS core/first shell/second shell structure.
  17. In paragraph 1, The above quantum dots comprise a core including Ag, In, Ga and S; and a shell including at least two selected from the group consisting of Ag, Ga, Zn and S, in a curable composition.
  18. A cured film manufactured using a curable composition according to any one of claims 1 to 17.
  19. A display device comprising the cured film of claim 18.

Description

Curable composition, cured film manufactured using said composition, display device including said cured film {CURABLE COMPOSITION, CURED LAYER USING THE COMPOSITION AND DISPLAY DEVICE INCLUDING THE CURED LAYER} The present invention relates to a curable composition, a cured film manufactured using the said composition, and a display device comprising the said cured film. In the case of conventional quantum dots, the solvents in which they can be dispersed are limited due to their hydrophobic surface characteristics, and consequently, it is true that there are significant difficulties in introducing them into polar systems such as binders or curable monomers. For example, even in the case of quantum dot ink compositions that are being actively researched, in the initial stages, they were only dispersed to a degree that could be used in solvents for curable compositions with relatively low polarity and high hydrophobicity. Because of this, it was difficult to include more than 20 weight percent of quantum dots relative to the total amount of the composition, so the light efficiency of the ink could not be increased beyond a certain level. Even if quantum dots were forcibly added and dispersed to increase light efficiency, the viscosity exceeded the range where ink-jetting is possible, and thus processability could not be satisfied. In addition, to achieve a viscosity range suitable for ink-jetting, a method has been used to lower the ink solid content by including more than 50% by weight of solvent relative to the total amount of the composition. Although this method also provides somewhat satisfactory results in terms of viscosity, it has the disadvantage of being difficult to apply to actual processes due to problems such as nozzle drying and clogging caused by solvent volatilization during ink-jetting, and a decrease in film thickness over time after ink-jetting, as well as severe thickness variation after curing. Therefore, a solvent-free type of quantum dot ink is the most desirable form for actual process application, and it is assessed that the current technology of applying quantum dots themselves to solvent-based compositions has now reached its limits. Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below. Unless otherwise specifically stated in this specification, "alkyl group" means a C1 to C20 alkyl group, "alkenyl group" means a C2 to C20 alkenyl group, "cycloalkenyl group" means a C3 to C20 cycloalkenyl group, "heterocycloalkenyl group" means a C3 to C20 heterocycloalkenyl group, "aryl group" means a C6 to C20 aryl group, "arylalkyl group" means a C6 to C20 arylalkyl group, "alkylene group" means a C1 to C20 alkylene group, "arylene group" means a C6 to C20 arylene group, "alkylarylene group" means a C6 to C20 alkylarylene group, "heteroarylene group" means a C3 to C20 heteroarylene group, and "alkoxylene group" means C1 to C20 It refers to the alkoxylene group. Unless specifically stated in this specification, "substitution" means that at least one hydrogen atom is a halogen atom (F, Cl, Br, I), a hydroxyl group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C20 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkenyl group, a C2 to C20 It means substituted with a heterocycloalkynyl group, a C3 to C20 heteroaryl group, or a combination thereof. Additionally, unless otherwise specifically stated in this specification, "hetero" means that the chemical formula contains at least one heteroatom among N, O, S, and P. Additionally, unless otherwise specifically stated in this specification, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" means that both "acrylic acid" and "methacrylic acid" are possible. Unless otherwise specified herein, "combination" means mixing or copolymerization. Unless otherwise defined in the chemical formulas within this specification, if a chemical bond is not drawn at a position where a chemical bond should be drawn, it means that a hydrogen atom is bonded at said position. Also, unless specifically mentioned in this specification, " " or "*" refers to the part connected to the same or different atoms or chemical formulas. While there are various key physical properties that quantum dots must possess for quantum do