PHOTOSENSITIVE POLYMERS FOR VOLUME HOLOGRAPHY
Photosensitive polymers for recording volume holograms, anisotropic volume holograms, and corresponding volume holographic elements are described herein.
1 . A recording material for forming a volume hologram, wherein the recording material is characterized by a thickness and comprises a compound comprising a moiety of Formula 1 or Formula 2:
wherein the moiety of Formula 1 or Formula 2 comprises a polymer backbone, a side chain comprising a linker L 1 and a photosensitive group PG;
wherein T 1 in Formula 2 is a terminal group; and
wherein the photosensitive group or the terminal group comprises a cycloaddition precursor (CAP).
2 . The recording material of claim 1 , wherein the linker L 1 comprises one or more of a single bond, a double bond, a triple bond, a carbonyl group, a carboxyl group, a methylene group, an ether group, and an optionally substituted phenylene group, and wherein the terminal group T 1 comprises one or more of a single bond, a double bond, a triple bond, an optionally substituted phenylene group, a carbonyl group, a carboxyl group, a methylene group, an ether group, —H, —OH, —CH 3 , —N(CH 3 ) 2 , —C 2 H 5 , —C 3 H 7 , —CN, —NO 2 , —OCH 3 , —OC 2 H 5 , and —OC 3 H 7 .
3 . The recording material of claim 1 , wherein the polymer backbone comprises one or more of a polysiloxane fragment, a polymethylmethacrylate (PMMA) fragment, a polyacrylate fragment, a polymethacrylate fragment, a cellulose fragment, a polyvinyl fragment, a polyurethane fragment, a polyamic acid fragment, or a polyimide fragment.
4 . The recording material of claim 1 , wherein the side chain is of any one of Formulas 101 to 105:
wherein in Formulas 101 to 105:
n is independently an integer from 0 to 12, m is independently an integer from 1 to 6, k is independently 0 or 1, l is independently 0 or 1, x is independently 0 or 1, y is independently 0 or 1, and z is independently at each occurrence 0, 1, 2, 3, or 4;
X and Y are independently selected from a single bond, a double bond, a triple bond, —C(O)—, —C(O)O—, —OC(O)—, and —C(O)NR a ;
R 1 is independently selected from —H, —OH, —CH 3 , —NR a R b , —C 2 H 5 , —C 3 H 7 , —CN, —NO 2 , —OCH 3 , —OC 2 H 5 , and —OC 3 H 7 ;
R 2 and R 3 are independently selected at each occurrence from hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, hydroxy, halo, cyano, fluoroalkyl, trifluoromethyl, trifluoromethoxy, nitro, trimethylsilanyl, —OR a , —SR a , —OC(O)R a , —N(R a )R b , —C(O)R a , —C(O)OR a , —OC(O)N(R a )R b , —C(O)N(R a )R b , —N(R a )C(O)OR a , —N(R a )C(O)R a , —N(R a )C(O)N(R a )R b , —N(R a )C(NR a )N(R a )R b , —N(R a )S(O) t R a , —S(O) t OR a , —S(O) t N(R a )R b , —S(O) t N(R a )C(O)R b , and —P(O)(OR a )(OR b ); and
R a and R b are independently selected at each occurrence from hydrogen, alkyl, fluoroalkyl, carbocyclyl, carbocyclylalkyl, aryl, aralkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl.
5 . The recording material of claim 1 , wherein the side chain is of any one of Formulas 106 to 117:
wherein in Formulas 106 to 117:
n is independently an integer from 0 to 12, m is independently an integer from 1 to 6, k is independently 0 or 1, l is independently 0 or 1, x is independently 0 or 1, y is independently 0 or 1, and z is independently at each occurrence 0, 1, 2, 3, or 4;
R 1 is independently selected from —H, —OH, —CH 3 , —NR a R b , —C 2 H 5 , —C 3 H 7 , —CN, —NO 2 , —OCH 3 , —OC 2 H 5 , and —OC 3 H 7 ;
R 2 and R 3 are independently selected at each occurrence from hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, hydroxy, halo, cyano, fluoroalkyl, trifluoromethyl, trifluoromethoxy, nitro, trimethylsilanyl, —OR a , —SR a , —OC(O)R a , —N(R a )R b , —C(O)R a , —C(O)OR a , —OC(O)N(R a )R b , —C(O)N(R a )R b , —N(R a )C(O)OR a , —N(R a )C(O)R a , —N(R a )C(O)N(R a )R b , —N(R a )C(NR a )N(R a )R b , —N(R a )S(O) t R a , —S(O) t OR a , —S(O) t N(R a )R b , —S(O) t N(R a )C(O)R b , and —P(O)(OR a )(OR b ); and
R a and R b are independently selected at each occurrence from hydrogen, alkyl, fluoroalkyl, carbocyclyl, carbocyclylalkyl, aryl, aralkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl.
6 . The recording material of claim 1 , wherein the side chain is of any one of Formulas 118 to 123:
wherein in Formulas 118 to 123:
n is independently an integer from 0 to 12, m is independently an integer from 1 to 6, k is independently 0 or 1, l is independently 0 or 1, x is independently 0 or 1, y is independently 0 or 1, and z is independently at each occurrence 0, 1, 2, 3, or 4;
R 1 is independently selected from —H, —OH, —CH 3 , —NR a R b , —C 2 H 5 , —C 3 H 7 , —CN, —NO 2 , —OCH 3 , —OC 2 H 5 , and —OC 3 H 7 ;
R 2 and R 3 are independently selected at each occurrence from hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, hydroxy, halo, cyano, fluoroalkyl, trifluoromethyl, trifluoromethoxy, nitro, trimethylsilanyl, —OR a , —SR a , —OC(O)R a , —N(R a )R b , —C(O)R a , —C(O)OR a , —OC(O)N(R a )R b , —C(O)N(R a )R b , —N(R a )C(O)OR a , —N(R a )C(O)R a , —N(R a )C(O)N(R a )R b , —N(R a )C(NR a )N(R a )R b , —N(R a )S(O) t R a , —S(O) t OR a , —S(O) t N(R a )R b , —S(O) t N(R a )C(O)R b , and —P(O)(OR a )(OR b ); and
R a and R b are independently selected at each occurrence from hydrogen, alkyl, fluoroalkyl, carbocyclyl, carbocyclylalkyl, aryl, aralkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl.
7 . The recording material of claim 1 , wherein the side chain is of any one of Formulas 124 to 131:
wherein in Formulas 124 to 131:
z is independently at each occurrence 0, 1, 2, 3, or 4, n is independently an integer from 0 to 12, and m is independently 0 or 1;
R 1 , R 2 , and R 3 are independently selected at each occurrence from hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, hydroxy, halo, cyano, fluoroalkyl, trifluoromethyl, trifluoromethoxy, nitro, trimethylsilanyl, —OR a , —SR a , —OC(O)R a , —N(R a )R b , —C(O)R a , —C(O)OR a , —OC(O)N(R a )R b , —C(O)N(R a )R b , —N(R a )C(O)OR a , —N(R a )C(O)R a , —N(R a )C(O)N(R a )R b , —N(R a )C(NR a )N(R a )R b , —N(R a )S(O) t R a , —S(O) t OR a , —S(O) t N(R a )R b , —S(O) t N(R a )C(O)R b , and —P(O)(OR a )(OR b ); and
R a and R b are independently selected at each occurrence from hydrogen, alkyl, fluoroalkyl, carbocyclyl, carbocyclylalkyl, aryl, aralkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl.
8 . The recording material of claim 1 , wherein the side chain is of any one of Formulas 1001 to 1011:
9 . The recording material of claim 1 , wherein the moiety of Formula 1 or Formula 2 is of any one of Formulas 2001 to 2014:
10 . The recording material of claim 1 , wherein the thickness of the recording material is between 0.5 m and 500 μm.
11 . The recording material of claim 1 , wherein the compound is a liquid crystal polymer.
12 . The recording material of claim 1 , wherein the compound is an amorphous polymer.
13 . The recording material of claim 1 , wherein the compound is optically aligned.
14 . The recording material of claim 1 , wherein the material is characterized by optically induced birefringence.
15 . The recording material of claim 1 , wherein the compound is optically transparent to visible light.
16 . The recording material of claim 1 , the material comprising a volume grating recorded in the recording material, wherein the volume grating is characterized by a Q parameter that is equal to or greater than 1, wherein
Q
=
2
π
λ
d
n
Λ
2
wherein,
λ is a wavelength of diffracting light,
d is the thickness of the recording material,
n is an average refractive index of the recording material for wavelength λ, and
Λ is a grating period (fringe spacing).
17 . The recording material of claim 16 , wherein Q is equal to or greater than 5.
18 . The recording material of claim 16 , wherein Q is equal to or greater than 10.
19 . A composite film for recording a volume hologram comprising the recording material of claim 1 and a substrate film.
20 . The composite film of claim 19 , wherein the substrate film comprises one or more of polycarbonate (PC), polyethylene terephthalate (PET), polybutylene terephthalate, polyethylene, polypropylene, cellulose acetate, cellulose hydrate, cellulose nitrate, cycloolefin polymers, polystyrene, polyepoxides, polysulphone, cellulose triacetate (CTA), polyamide, polymethyl methacrylate, polyvinyl chloride, polyvinyl butyral, polydicyclopentadiene, or a combination thereof.