Color conversion films produced by UV curing processes

Patent metadata

Field	Value
Publication number	US-10473979-B2
Application number	US-201615353256-A
Country	US
Kind code	B2
Filing date	Nov 16, 2016
Priority date	Nov 16, 2015
Publication date	Nov 12, 2019
Grant date	Nov 12, 2019

Abstract

Color conversion films for a LCD (liquid crystal display) having RGB (red, green, blue) color filters, as well as such displays, formulations, precursors and methods are provided, which improve display performances with respect to color gamut, energy efficiency, materials and costs. The color conversion films absorb backlight illumination and convert the energy to green and/or red emission at high efficiency, specified wavelength ranges and narrow emission peaks. For example, rhodamine-based fluorescent compounds are used in matrices produced by sol gel processes and/or UV (ultraviolet) curing processes which are configured to stabilize the compounds and extend their lifetime—to provide the required emission specifications of the color conversion films. Film integration and display configurations further enhance the display performance with color conversion films utilizing various color conversion elements.

First claim

The invention claimed is:

1. A color conversion film for a LCD (liquid crystal display) having RGB (red, green, blue) filters, the color conversion film prepared by UV (ultraviolet) curing from a formulation comprising:
65-70% monomers,
25-30% oligomers, and
5% photointiator, and
0.005-0.05% at least one rhodamine-based fluorescent (RBF) compound configured to absorb illumination from a LCD backlight source and have at least one of a R emission peak and a G emission peak;
wherein the at least one RBF compound is defined, respectively, by at least one of Formula 1 and Formula 4:

wherein
R 1 is COOR, NO 2 , COR, COSR, CO(N-heterocycle), CON(R) 2 or CN;
R 2 each is independently selected from H, halide, N(R) 2 , COR, CN, CON(R) 2 , CO(N-heterocycle), NCO, NCS, OR, SR, SO 3 H, SO 3 M and COOR;
R 3 each is independently selected from H, halide, N(R) 2 , COR, CN, CON(R) 2 , CO(N-heterocycle), NCO, NCS, OR, SR, SO 3 H, SO 3 M and COOR;
R 4 -R 16 and R 4′ -R 16′ are each independently selected from H, CF 3 , alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, benzyl, halide, NO 2 , OR, N(R) 2 , COR, CN, CON(R) 2 , CO(N-Heterocycle) and COOR;
R is H, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, benzyl, —(CH 2 CH 2 O) r CH 2 CH 2 OH, —(CH 2 ) p OC(O)NH(CH 2 ) q Si(Oalkyl) 3 , —(CH 2 ) p OC(O)CH═CH 2 or —(CH 2 ) p Si(Oalkyl) 3 ;
n and m are each independently an integer between 1-4;
p and q are each independently an integer between 1-6;
r is an integer between 0-10;
M is a monovalent cation; and
X − is an anion; and

wherein:
R 1 each is independently H, Q 1 , OQ 1 , CF 3 , C(O)OQ 1 , C(O)NQ 1 Q 2 , NHC(O)Q 1 , C(O)Q 1 , NQ 1 Q 2 , NO 2 , CN, SQ 1 , —NQ 1 Q 2 CONQ 3 Q 4 , NCO, NCS, —OC(O)OQ 1 , SO 3 —, SO 3 Q 1 , or halide;
n is an integer between 1-5;
R 3 , R 3′ , R 6 and R 6′ are each independently selected from H, CF 3 , alkyl, alkenyl, alkynyl, haloalkyl, heterocycloalkyl, cycloalkyl, aryl and benzyl;
R 2 , R 2′ , R 4 , R4′, R 5 and R 5′ are each independently selected from H, Q 1 , OQ 1 , CF 3 , NQ 1 Q 2 , NO 2 , CN, SO 3 − , SO 3 Q 1 and halide;
Q 1 and Q 2 are each independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, azide, haloalkyl, heterocycloalkyl, cycloalkyl, aryl, benzyl, —(CH 2 ) p OC(O)NH(CH 2 ) q Si(Oalkyl) 3 , —(CH 2 ) p OC(O)CH═CH 2 , —(CH 2 ) p Si(Oalkyl) 3 , —OC(O)N(H)Q 4 , —OC(S)N(H)Q 4 , —N(H)C(O)N(O 3 ) 2 and —N(H)C(S)N(O 3 ) 2 ;
Q 3 and Q 4 are each independently selected from H, alkyl, haloalkyl, heterocycloalkyl, cycloalkyl, aryl and benzyl;
X − is an anion.

2. The color conversion film of claim 1 , wherein the monomers consist of at least one of: dipropylene glycol diacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated pentaerythritol tetraacrylate, propoxylated (3) glyceryl acrylate and trimethylolpropane triacrylate.

3. The color conversion film of claim 1 , wherein the oligomers consist of at least one of: polyester acrylate, modified polyester resin diluted with dipropyleneglycol diacrylate and aliphatic urethane hexaacrylate.

4. The color conversion film of claim 1 , wherein the photointiator consists of at least one of: alpha-hydroxy-cyclohexyl-phenyl-ketone and alpha-hydroxy ketone.

5. The color conversion film of claim 1 , wherein the backlight source of the LCD provides blue illumination and the at least one RBF compound comprises at least one red-fluorescent RBF compound defined by Formula 1 and at least one green-fluorescent RBF compound defined by Formula 4.

6. A LCD comprising at least one color conversion film of claim 1 having both R and G emission peaks, a backlight unit comprising the backlight source and a LCD panel having the RGB color filters, wherein the at least one color conversion film is positioned in the LCD panel and is patterned with respect to a patterning of the RGB color filters to yield a spatial correspondence between film regions with R and G emission peaks and respective R and G color filter.

7. A LCD comprising at least one color conversion film of claim 1 having both R and G emission peaks, a backlight unit comprising the backlight source and a LCD panel having the RGB color filters, wherein an intensity of the R and G emission peaks of the at least one color conversion film are adjusted to fine tune a white point of the LCD to be at a center of an expected line of deterioration of the intensity within given LCD specifications.

Assignees

• Storedot Ltd

Inventors

• Szwarcman Daniel
• Cohen Elad
• ARMON Mor Shmuel
• KUKS Evgenia Liel (Jeny)
• Schwarz Rony
• Eisurovich Elena
• Aronov Daniel
• Sella Eran

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• G03F7/0007

  Filters, e.g. additive colour filters; Components for display devices · CPC title

• C09D5/22

  Luminous paints {(luminescent compositions C09K11/00)} · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C09B69/103

  containing a diaryl- or triarylmethane dye · CPC title