Rhodamine derivatives dyes, color-conversion-layer and uses thereof

Patent metadata

Field	Value
Publication number	US-10059843-B2
Application number	US-201715622158-A
Country	US
Kind code	B2
Filing date	Jun 14, 2017
Priority date	Nov 16, 2015
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

This invention is directed to photoluminescent compounds based on rhodamine dyes with red-shifted absorption and emission maxima and uses thereof for photoluminescence based devices.

First claim

What is claimed is:

1. A photoluminescent compound represented by the structure of formula (I):

wherein
R 1 is COOZ, NO 2 , COR, COSR, or CN;
R 2 each is independently selected from H, halide, COR, CN, NCO, NCS and COOZ;
R 3 each is independently selected from H, halide, COR, CN, NCO, NCS, OR, SR, SO 3 H, SO 3 M and COOZ;
R 4 -R 16 and R 4′ -R 16′ are each independently selected from H, alkyl, cycloalkyl, heterocycloalkyl, aryl, benzyl, halide, NO 2 , OR, N(R) 2 , COR, CON(R) 2 , CO(N-heterocycle) and COOR;
R is H, alkyl, 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 or —(CH 2 ) p Si(Oalkyl) 3 ;
Z is unsubstituted alkyl, or 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 or —(CH 2 ) p Si(Oalkyl) 3 ;
M is a monovalent cation;
n and m are each independently an integer between 1-4;
p and q is each independently an integer between 1-6;
r is an integer between 0-10;
and
X is an anion;
wherein if R 2 and R 3 are hydrogens (H), then R 1 is not COOZ.

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

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

4. The photoluminescent compound of claim 1 , wherein said anion is a sulfate, chloride, bromide, iodide, perchlorate, nitrate, trifluoroacetate, hydroxide, hydrosulfide, sulfide, nitrite, carboxylate, dicarboxylate, sulfonate, tetraflouroborate hexaflourophosphate, hypophosphite, phosphate, phosphite, cyanate, cyanide, isocyanate, thiocyanate, tetralkylborates, tetraarylborates or chromate.

5. A photoluminescent device comprising a color-conversion-layer comprising a photoluminescent compound according to claim 1 .

6. A photoluminescent device comprising a color-conversion-layer comprising a photoluminescent compound according to claim 2 .

7. A photoluminescent device comprising a color-conversion-layer comprising a photoluminescent compound according to claim 3 .

8. The photoluminescent device of claim 5 , wherein said anion is a sulfate, chloride, bromide, iodide, perchlorate, nitrate, trifluoroacetate, hydroxide, hydrosulfide, sulfide, nitrite, carboxylate, dicarboxylate, sulfonate, tetraflouroborate hexaflourophosphate, hypophosphite, phosphate, phosphite, cyanate, cyanide, isocyanate, thiocyanate, tetralkylborates, tetraarylborates or chromate.

9. The photoluminescent device of claim 5 wherein said color-conversion-layer is in a form of a film.

10. The photoluminescent device of claim 5 , wherein said device is integrated in a display device.

11. The photoluminescent device of claim 9 , wherein said device is integrated in a display device.

Assignees

• Storedot Ltd

Inventors

• KUKS Evgenia Liel
• Schwarz Rony
• Sella Eran
• ARMON Mor Shmuel
• Szwarcman Daniel

Classifications

• C09B69/008

  Dyes containing a substituent, which contains a silicium atom · CPC title

• C09K2211/1048

  with oxygen · CPC title

• C09B69/103

  containing a diaryl- or triarylmethane dye · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• G03F7/0007

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