Color conversion with solid matrix films

Patent metadata

Field	Value
Publication number	US-10533091-B2
Application number	US-201715691776-A
Country	US
Kind code	B2
Filing date	Aug 31, 2017
Priority date	Nov 16, 2015
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

Abstract

This invention is directed to photoluminescent compounds based on rhodamine dyes with green or red emission and uses thereof for photoluminescence based devices.

First claim

The invention claimed is:

1. A red-fluorescent rhodamine based fluorescent compound represented by the structure of formula (I):

wherein
R 1 is halide, haloalkyl, COOZ, COR, COSR or CN;
R 2 each is independently selected from H, halide, N(R) 2 , COR, CN, NCO, NCS, OR, SR, SO 3 H, SO 3 M and COOZ;
R 3 each is independently selected from H, halide, N(R) 2 , COR, CN, NCO, NCS, OR, SR, SO 3 H, SO 3 M and COOZ;
R 4 -R 7 , R 13 -R 16 , R 4 ′-R 7 ′ and R 13 ′-R 16 ′ are each independently selected from H, alkyl, alkenyl, alkynyl, epoxide, alkylated epoxide, azide, cycloalkyl, heterocycloalkyl, aryl, benzyl, halide, NO 2 , SR, OR, N(R) 2 , COR, CN, CON(R) 2 , CO(N-heterocycle) and COOR;
R 8 -R 9 , R 11 -R 12 , R 8 ′-R 9 ′ and R 11 ′-R 12 ′ are each independently selected from absent, H, alkyl, alkenyl, alkynyl, epoxide, alkylated epoxide, azide, cycloalkyl, heterocycloalkyl, aryl, benzyl, halide, NO 2 , SR, OR, N(R) 2 , COR, CN, CON(R) 2 , CO(N-heterocycle) and COOR;
R 10 and R 10 ′ are each independently selected from H, alkyl, alkenyl, alkynyl, epoxide, alkylated epoxide, alkylated azide, azide, SO 3 H, SO 3 M, cycloalkyl, heterocycloalkyl, aryl, benzyl, halide, NO 2 , SR, OR, N(R) 2 , COR, CN, CON(R) 2 , CO(N-heterocycle) and COOR;
R is H, haloalkyl, alkyl, cycloalkyl, 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)NH(CH 2 ) q Si(halide) 3 , —(CH 2 ) p OC(O)CH═CH 2 , —(CH 2 ) p OC(O)C(CH 3 )═CH 2 , —(CH 2 ) p Si(halide) 3 , alkenyl, alkynyl, alkylated epoxide, alkylated azide, azide, or —(CH 2 ) p Si(Oalkyl) 3 ;
Z is alkyl, haloalkyl, alkenyl, alkynyl, alkylated epoxide, cycloalkyl, heterocycloalkyl, 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 , —(CH 2 ) p OC(O)C(CH 3 )═CH 2 , or —(CH 2 ) p Si(Oalkyl) 3 ;
Z 101 is O;
M is a monovalent cation;
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;
X is an anion;
wherein if there is a double bond between the carbons which are substituted by R 8 , R 8 ′, R 9 and R 9 ′—then R 8 and R 9 are absent or R 8 and R 9 ′ are absent or R 8 ′ and R 9 are absent or R 8 ′ and R 9 ′ are absent;
wherein if there is a double bond between the carbons which are substituted by R 11 , R 11 ′, R 12 and R 12 ′—then R 11 and R 12 are absent or R 11 and R 12 ′ are absent or R 11 ′ and R 12 are absent or R 11 ′ and R 12 ′ are absent;
wherein if all R 2 and R 3 are H, then R 1 at position 3 is halide, haloalkyl, COR, COSR or CN; and
wherein if m+n=4, all R 2 and R 3 are halides and R 1 at position 3 is COOZ—then at least one of the bonds, selected from the bond between the carbons substituted by R 8 , R 8 ′, R 9 and R 9 ′ and the bond between the carbons substituted by R 11 , R 11 ′, R 12 and R 12 ′—is a single bond.

2. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula (II):

3. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula (III):

4. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula (IV):

5. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula (V):

6. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula 1-11, 20 or 23-26:

7. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula:

8. The fluorescent compound of claim 1 , wherein said compound is represented by the structure of formula:

Assignees

• Storedot Ltd

Inventors

• KUKS Evgenia Liel (Jeny)
• Schwarz Rony
• Sella Eran
• Szwarcman Daniel

Classifications

• C09B69/103

  containing a diaryl- or triarylmethane dye · CPC title

• C09B11/22

  containing OH groups bound to an aryl nucleus {and their ethers and esters} · CPC title

• G03F7/105

  having substances, e.g. indicators, for forming visible images · CPC title

• C09B11/24 Primary

  Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes} · CPC title

• G03F7/0007

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