Color conversion with solid matrix films
This invention is directed to photoluminescent compounds based on rhodamine dyes with green or red emission and uses thereof for photoluminescence based devices.
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: