IP Library Granted Patent US 10,473,979
Granted Patent B2
US 10,473,979 · App. 15/353,256 · Granted Nov 12, 2019

Color conversion films produced by UV curing processes

Inventors: Daniel Szwarcman (Pardes-Hanna Karkur, IL); Elad Cohen (Tel Aviv, IL); Mor Shmuel Armon (Ramat-Gan, IL); Evgenia Liel (Jeny) Kuks (Ramat Gan, IL); Rony Schwarz (Kibbutz Ma'anit Menashe, IL); Elena Eisurovich (Hadera, IL); Daniel Aronov (Netanya, IL); Eran Sella (Tel-Aviv, IL)
Assignee: Storedot Ltd.
G02F1/133617C09B11/24C09B69/008C09B69/103C09D4/00C09D5/22C09K11/025C09K11/06G02F1/133516G02F1/133621G03F7/0007G03F7/027G03F7/031G03F7/105H01L51/0051H01L51/0071C09K2211/1007C09K2211/1048C09K2211/1088G02F2001/133614G02F2203/055
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Quick Facts
Patent No.
US 10,473,979
App. No.
15/353,256
Granted
Nov 12, 2019
Kind
B2
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.

Claims (31)

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2020
From: STOREDOT LTD.
To: MOLECULED LTD.
Reel/Frame 051421/0486 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2017
From: SZWARCMAN, DANIEL; COHEN, ELAD; ARMON, MOR SHMUEL; KUKS, EVGENIA LIEL; SCHWARZ, RONY; EISUROVICH, ELENA; ARONOV, DANIEL; SELLA, ERAN
To: STOREDOT LTD.
Reel/Frame 041187/0074 →
Continuity (6)
Continuation In Part 15252492 · Aug 31, 2016
Continuation In Part 15252597 · Aug 31, 2016
Provisional Application 62255857 · Nov 16, 2015
Provisional Application 62255860 · Nov 16, 2015
Provisional Application 62255853 · Nov 16, 2015
Related Publication 20170139277A1 · May 18, 2017