IP Library Granted Patent US 10,473,968
Granted Patent B2
US 10,473,968 · App. 15/353,453 · Granted Nov 12, 2019

Protective layers produced by sol gel 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.
G02F1/133514C09D185/00C09K11/06G02B1/14C09K2211/1007C09K2211/1029C09K2211/1088G02F2001/133614G02F2201/52
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Quick Facts
Patent No.
US 10,473,968
App. No.
15/353,453
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 (27)

1. A color conversion film for a LCD (liquid crystal display) having RGB (red, green, blue) color filters, the color conversion film configured to absorb illumination from a backlight source of the LCD and having at least one of a R emission peak and a G emission peak, wherein the color conversion film further comprises a protective coating prepared by a sol gel process;

wherein the color conversion film further comprises at least one rhodamine-based fluorescent (RBF) compound selected to absorb illumination from the backlight source of the LCD and have the at least one of a R emission peak and a G emission peak; and

wherein the at least one RBF compound is defined 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, CF3, 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 , R 4′ , 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(Q 3 ) 2 and —N(H)C(S)N(Q 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 sol gel process is carried out with at least one of: ZPH, MMA, trimethoxysilane derivative, and an ESOR.

3. The color conversion film of claim 1 , wherein the color conversion film is produced by at least one of a sol gel process and a UV (ultraviolet) curing process.

4. An LCD comprising at least one color conversion film of claim 1 , wherein the LCD comprises 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.

5. An LCD comprising at least one color conversion film of claim 1 , wherein the LCD comprises 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.

6. An LCD comprising at least one color conversion film of claim 1 , wherein the LCD comprises a backlight unit comprising the backlight source and a LCD panel having the RGB color filters, wherein the RBF compounds in the film are at least partially self-assembled to at least partially provide polarized emission, and wherein the at least one color conversion film replaces at least one polarizer film in the LCD.

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 041187/0092 →
Continuity (6)
Continuation In Part 15252492 · Aug 31, 2016
Continuation In Part 15252597 · Aug 31, 2016
Provisional Application 62255860 · Nov 16, 2015
Provisional Application 62255857 · Nov 16, 2015
Provisional Application 62255853 · Nov 16, 2015
Related Publication 20170139270A1 · May 18, 2017