Photoluminescent compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-10240042-B2
Application number	US-201715661151-A
Country	US
Kind code	B2
Filing date	Jul 27, 2017
Priority date	Aug 31, 2016
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

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

First claim

What is claimed is:

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

wherein
T 1 each is independently H, Q 1 , OQ 1 , CF 3 ,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 or halide;
T 2 each is independently H, Q 1 , OQ 1 , CF 3 , 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 or halide;
T 3 each is independently H, Q 1 ,OQ 1 ,CF 3 , 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 or halide;
T 4 and T 4′ are each independently selected from alkyl, haloalkyl, heterocycloalkyl, cycloalkyl and benzyl;
T 5 and T 5′ are each independently selected from H, —(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 , —N(H)C(S)N(Q 3 ) 2 , NQ 1 Q 2 CONQ 3 Q 4 , NCO, NCS, alkenyl, alkynyl, epoxide, alkylated epoxide, azide and halide;
T 6 , T 6′ , T 7′ and T 7′ are each independently selected from H, Q 1 , OQ 1 , CF 3 , C(O)Q 1 , COOQ 1 , CON(Q 1 ) 2 , NQ 1 Q 2 , NO 2 , CN, SO 3 − , SO 3 M, SO 3 H, SQ 1 , —NQ 1 Q 2 CONQ 3 Q 4 , NCO, NCS, alkenyl, alkynyl, epoxide, alkylated epoxide, azide and halide; or
T 4 and T 5 or T 4′ and T 5′ form together a N-heterocyclic ring wherein said ring is optionally substituted;
Q 1 and Q 2 are each independently selected from H, alkyl, 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;
M is a monovalent cation;
n, m and l are independently an integer between 1-5;
p and q are independently an integer between 1-6;
X − is an anion;
wherein if one of T 5 -T 7 and T 5′ -T 7′ is SO 3 − , then X is omitted;
wherein if at least one of T 4 and T 4′ is haloalkyl—then at least one of T 5 and T 5 ′ is H or halide; and
wherein if at least one of T 4 and T 4′ is alkyl—then all T 1 -T 3 are each independently selected from H, Q 1 , OQ 1 , CF 3 , C(O)Q 1 , NQ 1 Q 2 , NO 2 ,CN, SQ 1 , —NQ 1 Q 2 CONQ 3 Q 4 , NCO, NCS or —OC(O)OQ 1 .

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

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

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

5. 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, tetrafluoroborate, hexafluorophosphate, hypophosphite, phosphate, phosphite, cyanate, cyanide, isocyanate, thiocyanate, tetra-alkylborate, tetra-arylborate or chromate.

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

7. The photoluminescent device of claim 6 , wherein said color-conversion-layer is in a form of a film.

8. The photoluminescent device of claim 7 , wherein said photoluminescent compound comprises an emission peak between 520-560 nm and FWHM between 30 and 55 nm.

Assignees

• Storedot Ltd

Inventors

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

Classifications

• G02F2001/133614

  Physics · mapped topic

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C07D311/82

  Xanthenes · CPC title

• F21V9/30

  Elements containing photoluminescent material distinct from or spaced from the light source (shades F21V1/17; globes, bowls or cover glasses F21V3/08, F21V3/12; refractors F21V5/10; reflectors F21V7/26, F21V7/30; elements with provision for controlling the spectral properties or intensity F21V9/40) · CPC title

• G02F1/133617

  Illumination with ultraviolet light; Luminescent elements or materials associated to the cell · CPC title