Color conversion films comprising a rhodamine-based fluorescent (rbf) compound and plasmon enhanced fluorescent dyes

Abstract

Color conversion films for a LCD (liquid crystal display) having RGB (red, green, blue) color filters, as well as such displays, formulations, precursors and methods are provided, which improve display performances with respect to color gamut, energy efficiency, materials and costs. The color conversion films absorb backlight illumination and convert the energy to green and/or red emission at high efficiency, specified wavelength ranges and narrow emission peaks. For example, rhodamine-based fluorescent compounds are used in matrices produced by sol gel processes and/or UV (ultraviolet) curing processes which are configured to stabilize the compounds and extend their lifetime—to provide the required emission specifications of the color conversion films. Film integration and display configurations further enhance the display performance with color conversion films utilizing various color conversion elements. Fluorescent emission may be enhanced by plasmon resonance of coupled nanoparticles.

1 . A color conversion film for a LCD (liquid crystal display) having RGB (red, green, blue) color filters, the color conversion film comprising at least one rhodamine-based fluorescent (RBF) compound selected to absorb illumination from a backlight source of the LCD and having at least one of a R emission peak and a G emission peak,
 wherein the at least one RBF compound is defined by Formula 4:   
       
         
           
           
               
               
           
         
         wherein: 
         R 1  each is independently H, Q 1 , OQ 1 , CF 3 , C(O)OQ 1 , C(O)NQ 1 Q 2 , NHC(O)Q 1 , 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 , SO 3 —, SO 3 Q 1 , or halide; 
         n is an integer between 1-5; 
         R 3 , R 3′ , R 6  and R 6′  are each independently selected from H, CF 3 , alkyl, alkenyl, alkynyl, haloalkyl, heterocycloalkyl, cycloalkyl, aryl and benzyl; 
         R 2 , R 2′ , R 4 , R4′, R 5  and R 5′  are each independently selected from H, Q 1 , OQ 1 , CF 3 , NQ 1 Q 2 , NO 2 , CN, SO 3 —, SO 3 Q 1  and halide; 
         Q 1  and Q 2  are each independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, azide, 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; 
         X is an anion; 
         wherein at least some of the at least one RBF compound is electromagnetically coupled to plasmon-resonant (PR) elements having a resonance spectrum that at least partly overlap at least one of an absorption and an emission spectra of the at least one RBF compound, wherein the PR elements comprise metallic nanoparticles ranging in diameter between 10-100 nm, metal coated or sputtered on the color conversion film, a metallic film comprising islands or perforations on at least part of the color conversion film, a multilayer hyperbolic metamaterial, or a combination thereof. 
       
     
     
         2 . The color conversion film of  claim 1 , produced at least partially by a sol gel process and/or a UV (ultraviolet) curing process. 
     
     
         3 . The LCD comprising the color conversion film of  claim 1 . 
     
     
         4 . A method comprising:
 preparing at least one color conversion film comprising at least one RBF compound selected to absorb illumination from a backlight source of the LCD and having at least one of a R emission peak and a G emission peak,   wherein the at least one RBF compound is defined by Formula 4:   
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  each is independently H, Q 1 , OQ 1 , CF 3 , C(O)OQ 1 , C(O)NQ 1 Q 2 , NHC(O)Q 1 , 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 , SO 3 —, SO 3 Q 1 , or halide; 
 n is an integer between 1-5; 
 R 3 , R 3′ , R 6  and R 6′  are each independently selected from H, CF 3 , alkyl, alkenyl, alkynyl, haloalkyl, heterocycloalkyl, cycloalkyl, aryl and benzyl; 
 R 2 , R 2′ , R 4 , R4′, R 5  and R 5′  are each independently selected from H, Q 1 , OQ 1 , CF 3 , NQ 1 Q 2 , NO 2 , CN, SO 3 —, SO 3 Q 1  and halide; 
 Q 1  and Q 2  are each independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, azide, 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; 
 X is an anion;
 electromagnetically coupling at least some of the at least one RBF compound to PR elements having a resonance spectrum that at least partly overlaps at least one of an absorption and an emission spectra of the at least one RBF compound, wherein the PR elements comprise metallic nanoparticles ranging in diameter between 10-100 nm, metal coated or sputtered on the color conversion film, a metallic film comprising islands or perforations on at least part of the color conversion film, a multilayer hyperbolic metamaterial, or a combination thereof, and 
 integrating the at least one color conversion film in a LCD with RGB color filters. 
 
 
     
     
         5 . The method of  claim 4 , further comprising using linkers for the electromagnetic coupling. 
     
     
         6 . The method of  claim 4 , further comprising designing PR elements to enhance a plasmon field thereof. 
     
     
         7 . The method of  claim 4 , further comprising embedding the at least one RBF compound in a matrix enclosed within the PR elements being plasmonic nanostructure shells. 
     
     
         8 . The method of  claim 4 , wherein the at least one color conversion film is prepared by at least one corresponding sol-gel process and/or UV curing process.