Volume phase hologram recording material and optical information recording medium
View Patent ↗Disclosed is a volume phase hologram recording material of high sensitivity, high contrast, and excellent record retention properties and also disclosed is a volume phase hologram recording medium using the said material. The volume phase hologram recording material mainly contains a three-dimensional crosslinked polymer matrix, a radically polymerizable monomer, and a photoradical polymerization initiator. The three-dimensional crosslinked polymer matrix is formed from a matrix-forming compound having two photoradically polymerizable unsaturated groups and two non-photoradically polymerizable hydroxyl groups represented by the following general formula (1) and another matrix-forming compound having no photoradically polymerizable group.
1. A volume phase hologram recording material which comprises mainly containing (a) a three-dimensional crosslinked polymer matrix, (b) a photoradically polymerizable monomer, and (c) a photopolymerization initiator wherein the three-dimensional crosslinked polymer matrix (a) has photoradically polymerizable groups and is formed from a polymer matrix-forming material (A) containing 0.5-40 wt % of a matrix-forming compound having photoradically polymerizable groups (a1) and a matrix-forming compound having no photoradically polymerizable group (a2) and the aforementioned matrix-forming compound having photoradically polymerizable groups (a1) is represented by the following formula (1):
in formula (1), Ar is a divalent group having one or more aromatic rings, R 1 and R 2 each is independently a hydrogen atom or a methyl group, L 1 is an oxygen atom, a sulfur atom, or —(OR 3 ) n O—, R 3 is an alkylene group, n is an integer of 1-4, and L 2 is a divalent group optionally having aromatic rings
wherein the photoradically polymerizable groups to be introduced to the three-dimensional crosslinked polymer matrix is in a concentration of 0.01-0.2 mol/kg of the whole polymer matrix-forming material (A).
2. A volume phase hologram recording material as described in claim 1 wherein the photoradically polymerizable monomer (b) contains 50 wt % or more of a monofunctional monomer (b1) having a plurality of aromatic rings and one ethylenic double bond in the molecule.
3. A volume phase hologram recording material as described in claim 2 wherein the monofunctional monomer (b1) has a refractive index (n D ) of 1.60 or more.
4. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 3 on a support or between two supports.
5. A volume phase hologram recording material as described in claim 2 wherein the monofunctional monomer (b1) is one kind or more of compounds selected from the group of vinylnaphthalene, vinylbiphenyl, vinylterphenyl, N-vinylcarbazole, vinylpyrene, dibenzofulvene, benzyl vinylbenzyl sulfide, and phenyl vinylphenyl sulfide.
6. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 5 on a support or between two supports.
7. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 2 on a support or between two supports.
8. A volume phase hologram recording material as described in claim 1 wherein the matrix-forming compound having photoradically polymerizable groups (a1) is at least one kind of unsaturated compound represented by any one of the following formulas (2)-(5):
in these formulas, R 1 is independently a hydrogen atom or a methyl group, R 4 is independently a hydrogen atom or an alkyl group of 1-4 carbon atoms, R 5 is a hydrogen atom, a halogen atom, an alkyl group of 1-4 carbon atoms, or an alkoxyl group of 1-4 carbon atoms, L 1 is an oxygen atom, a sulfur atom, or —(OR 3 ) n O—, L 3 is an oxygen atom, a sulfur atom, —C(O)O—, or —N(R 6 )—, L 4 is a single bond, an oxygen atom, a sulfur atom, a sulfonyl group, or an alkylene group, n is an integer of 1-4. R 3 is an alkylene group, and R 6 is a hydrogen atom or an alkyl group of 1-4 carbon atoms.
9. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 8 on a support or between two supports.
10. A volume phase hologram recording material as described in claim 1 wherein the polymer matrix-forming material (A) is a mixture of two kinds or more of compounds which are so combined as to control the difference in refractive index at 0.06 or more in absolute value.
11. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 10 on a support or between two supports.
12. A volume phase hologram recording material as described in claim 1 wherein the polymer matrix-forming material (A) further contains at least one kind of non-reactive compound (d) which is compatible with the three-dimensional crosslinked polymer matrix (a).
13. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 12 on a support or between two supports.
14. A volume phase hologram recording material as described in claim 1 wherein at least one kind of chain transfer agent which is compatible with the three-dimensional crosslinked polymer matrix (a) is contained in an amount of 0.1-20 wt %.
15. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 14 on a support or between two supports.
16. An optical information recording medium for volume phase hologram recording prepared by forming any one of the volume phase hologram recording materials described in claim 1 on a support or between two supports.
17. A volume phase hologram recording material precursor which comprises mainly containing a polymer matrix-forming material (A), a photoradically polymerizable monomer (b), and a photoradical polymerization initiator (c) wherein the polymer matrix-forming material (A) contains 0.5-40 wt % of a matrix-forming compound having photoradically polymerizable groups (a1) and a matrix-forming compound having no photoradically polymerizable group (a2), a three-dimensional crosslinked polymer matrix is formed by a polymerization reaction other than a photoradical polymerization reaction, and the aforementioned matrix-forming compound having radically polymerizable groups (a1) is an unsaturated compound represented by the following formula (1):
in formula (1), Ar is a divalent group having one or more aromatic rings, R 1 and R 2 each is independently a hydrogen atom or a methyl group, L 1 is an oxygen atom, a sulfur atom, or —(OR 3 ) n O—, R 3 is an alkylene group, n is an integer of 1-4, and L 2 is a divalent group optionally having aromatic rings
wherein the photoradically polymerizable groups to be introduced to the three-dimensional crosslinked polymer matrix is in a concentration of 0.01-0.2 mol/kg of the whole polymer matrix-forming material (A).
18. A volume phase hologram recording material precursor as described in claim 17 wherein the photoradically polymerizable monomer (b) contains 50 wt % or more of a monofunctional monomer (b1) having a plurality of aromatic rings and one ethylenic double bond in the molecule.
19. A method for forming a volume phase hologram recording material mainly containing a three-dimensional crosslinked polymer matrix (a), a photoradically polymerizable monomer (b), and a photoradical polymerization initiator (c) which comprises converting the volume phase hologram recording material precursor described in claim 18 by a polymerization reaction other than a photoradical polymerization reaction to a three-dimensional crosslinked polymer matrix having photoradically polymerizable groups.
20. A method for forming a volume phase hologram recording material mainly containing a three-dimensional crosslinked polymer matrix (a), a photoradically polymerizable monomer (b), and a photoradical polymerization initiator (c) which comprises converting the volume phase hologram recording material precursor described in claim 17 by a polymerization reaction other than a photoradical polymerization reaction to a three-dimensional crosslinked polymer matrix having photoradically polymerizable groups.
21. A volume phase hologram recording material which comprises mainly containing (a) a three-dimensional crosslinked polymer matrix, (b) a photoradically polymerizable monomer, and (c) a photopolymerization initiator wherein the three-dimensional crosslinked polymer matrix (a) has photoradically polymerizable groups and is formed from a polymer matrix-forming material (A) containing 0.5-40 wt % of a matrix-forming compound having photoradically polymerizable groups (a1) and a matrix-forming compound having no photoradically polymerizable group (a2) and the aforementioned matrix-forming compound having photoradically polymerizable groups (a1) is represented by the following formula (2) or (3):
in these formulas, R 1 is independently a hydrogen atom or a methyl group, R 4 is independently a hydrogen atom or an alkyl group of 1-4 carbon atoms, R 5 is a hydrogen atom, a halogen atom, an alkyl group of 1-4 carbon atoms, or an alkoxyl group of 1-4 carbon atoms, L 1 is an oxygen atom, a sulfur atom, or —(OR 3 ) n O—, L 3 is an oxygen atom, a sulfur atom, —C(O)O—, or —N(R 6 )—, n is an integer of 1-4, R 3 is an alkylene group, and R 6 is a hydrogen atom or an alkyl group of 1-4 carbon atoms
wherein the photoradically polymerizable groups to be introduced to the three-dimensional crosslinked polymer matrix is in a concentration of 0.01-0.2 mol/kg of the whole polymer matrix-forming material (A).
22. A volume phase hologram recording material as described in claim 21 , wherein the matrix-forming compound having photoradically polymerizable groups (a1) represented by said formula (2) or (3) is in a content of 1-10 wt % of the polymer matrix-forming material (A) which forms the polymer matrix (a).
23. A volume phase hologram recording material as described in claim 21 , wherein the photoradically polymerizable groups to be introduced to the three-dimensional crosslinked polymer matrix is in a concentration of 0.025-0.2 mol/kg of the whole polymer matrix-forming material (A).
24. A volume phase hologram recording material as described in claim 21 , wherein an isocyanate compound having two or more isocyanate groups in the molecule or a mixture of such isocyanate compounds constitutes the matrix-forming compound having no photoradically polymerizable group (a2).
25. A volume phase hologram recording material precursor which comprises mainly containing a polymer matrix-forming material (A), a photoradically polymerizable monomer (b), and a photoradical polymerization initiator (c) wherein the polymer matrix-forming material (A) contains 0.5-40 wt % of a matrix-forming compound having photoradically polymerizable groups (a I) and a matrix-forming compound having no photoradically polymerizable group (a2), a three-dimensional crosslinked polymer matrix is formed by a polymerization reaction other than a photoradical polymerization reaction, and the aforementioned matrix-forming compound having radically polymerizable groups (a1) is an unsaturated compound represented by the following formula (2) or (3):
in these formulas, R 1 is independently a hydrogen atom or a methyl group, R 4 is independently a hydrogen atom or an alkyl group of 1-4 carbon atoms, R 5 is a hydrogen atom, a halogen atom, an alkyl group of 1-4 carbon atoms, or an alkoxyl group of 1-4 carbon atoms, L 1 is an oxygen atom, a sulfur atom, or —(OR 3 ) n O—, L 3 is an oxygen atom, a sulfur atom, —C(O)O—, or —N(R 6 )—, n is an integer of 1-4, R 3 is an alkylene group, and R 6 is a hydrogen atom or an alkyl group of 1-4 carbon atoms
wherein the photoradically polymerizable groups to be introduced to the three-dimensional crosslinked polymer matrix is in a concentration of 0.01-0.2 mol/kg of the whole polymer matrix-forming material (A).