IP Library Granted Patent US 10,240,042
Granted Patent B2
US 10,240,042 · App. 15/661,151 · Granted Mar 26, 2019

Photoluminescent compounds and uses thereof

Inventors: Evgenia Liel (Jeny) Kuks (Ramat Gan, IL); Rony Schwarz (Kibbutz Ma'anit, IL); Eran Sella (Tel-Aviv, IL); Mor Shmuel Armon (Ramat Gan, IL); Daniel Szwarcman (Pardes-Hanna Karkur, IL)
Assignee: StoreDot Ltd.
C09B11/24C07D311/82C09K11/06F21V9/30G02F1/133617C09K2211/1022C09K2211/1088G02F2001/133614
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Quick Facts
Patent No.
US 10,240,042
App. No.
15/661,151
Granted
Mar 26, 2019
Kind
B2
Abstract

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

Claims (27)

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.

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 Dec 25, 2018
From: KUKS, EVGENIA LIEL (JENY); SCHWARZ, RONY; SELLA, ERAN; ARMON, MOR SHMUEL; SZWARCMAN, DANIEL
To: STOREDOT LTD.
Reel/Frame 047849/0818 →
Continuity (2)
Continuation 15252597 · Aug 31, 2016
Related Publication 20180057689A1 · Mar 1, 2018