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