Photosensitive composition for volume hologram recording

• US 20070148556A1
• Filed: 12/21/2004
• Published: 06/28/2007
• Est. Priority Date: 12/22/2003
• Status: Abandoned Application

• Current Assignee: Dai Nippon Printing Company Limited
• Original Assignee: Dai Nippon Printing Company Limited
• Inventors: Ohtaki, Hiroyuki, Yoshihara, Toshio, Matsui, Fumio, Maeno, Yoshihito, Ihara, Junichiro
• Application Number:
  US10/583,880
• Publication Number:
  US 20070148556A1
• Time in Patent Office: Days
• US Class Current: 430/1
• CPC Class Codes: G03F 7/001 Phase modulating patterns, e.g. refractive index patterns
• CPC Class Codes: G03F 7/031 Organic compounds not covered by group G03F7/029
• CPC Class Codes: G03H 1/02 Details of features involved during the holographic process; Replication of holograms without interference recording
• CPC Class Codes: G03H 1/0248 Volume holograms
• CPC Class Codes: G03H 2260/12 Photopolymer

Abstract

A volume hologram recording material having a composition that is adjusted in accordance with a recording wavelength in a visible region set individually and specifically, and is excellent in sensitivity or hologram recording performance. A photosensitive composition for volume hologram recording having a photopolymerizable compound, a photopolymerization initiator and a sensitizing dye, and a maximum absorption wavelength of the sensitizing dye deviates by 14 nm or more from a predetermined volume hologram recording wavelength set in a visible region and the composition itself has absorption at the volume hologram recording wavelength.

Claims

1-8. -8. (canceled)

9. A method of producing a volume hologram, wherein a hologram recording portion comprising a photosensitive composition for volume hologram recording containing a photopolymerizable compound as a refractive index modulation component, a photopolymerization initiator and a sensitizing dye which increases sensitivity of the photopolymerization initiator with respect to a wavelength of a visible region is subject to interference exposure using a predetermined volume hologram recording wavelength set in a visible region so as to record the volume hologram, and wherein the sensitizing dye has absorption at the volume hologram recording wavelength and a maximum absorption wavelength of the sensitizing dye deviates by 14 nm or more from the volume hologram recording wavelength.

10. A method of producing a volume hologram according to claim 9, wherein the photosensitive composition for volume hologram recording further contains a binder resin and/or a thermosetting compound.

11. A method of producing a volume hologram according to claim 9, wherein the photopolymerizable compound is at least one kind selected from the group consisting of a photoradical polymerizable compound and a photocationic polymerizable compound.

12. A method of producing a volume hologram according to claim 9, wherein the photosensitive composition for volume hologram recording further contains a second refractive index modulation component having different refractive index from the photopolymerizable compound.

13. A method of producing a volume hologram according to claim 9, wherein the sensitizing dye is a cyclopentanone skeleton containing compound represented by the following general formula (1):

wherein, “

R”

is a carbon-nitrogen containing substituent represented by “

N_xC_y”

in which x=1 to 4, y=8 to 30;

“

R”

may contain a hydrogen atom and/or a halogen atom;

“

n”

is an integer of 0 to 3.

14. A method of producing a volume hologram according to claim 9, wherein the photopolymerization initiator is a compound containing diaryliodonium skeleton represented by the following general formula (2):

wherein, each of “

X₁” and

“

X₂”

is independently an alkyl group having 1 to 20 carbons, halogen or an alkoxyl group having 1 to 20 carbons;

“

Y⁻

”

is a monovalent anion.

15. A method of producing a volume hologram according to claim 9, wherein the maximum absorption wavelength of the sensitizing dye deviates by 14 nm or more with respect to a predetermined volume hologram recording wavelength set within a region of 514 nm to 560 nm.

16. A method of producing a volume hologram according to claim 15, wherein the volume hologram recording wavelength is set within a region of 514 nm to 560 nm and the sensitizing dye is selected from a group consisting of the following compounds (3) and (4):

Chemical name;

2,5-bis(4-diethylaminobenzylidene)cyclopentanone;

Chemical name;

2,5-bis(4-dibutylaminobenzylidene)cyclopentanone.

17. A method of producing a volume hologram according to claim 9, wherein the volume hologram recording wavelength is set within a region of 630 nm to 670 nm and the sensitizing dye is selected from a group consisting of the following compounds (1) and (2):

Chemical name;

2-[[3-allyl-5-[2-(5,6-dimethyl-3-propyl-2(3H) -benzothiazolylidene)ethylidene]-4-oxo-2-thiazolidinylidene]methyl]-3-ethyl-4,5-diphenylthiazolium methylsulfate;

Chemical name;

1-heptyl-2-[3-(1-heptyl-5-methoxy-3,3-dimethyl -1,3-dihydro-indole-2-ilidenemethyl)-2-hydroxy-4-oxo-2-cyclobutenylidenemethyl]-5-methoxy-3,3-dimethyl-3H-indolium inner salt.

18. A method of producing a volume hologram according to claim 9, wherein the volume hologram recording wavelength is set within a region of 420 nm to 488 nm and the sensitizing dye is selected from a group consisting of the following compounds (5) and (6):

Chemical name;

1,3-diethyl-5-[2-(1-methyl-pyrrolidine-2-ilidene)-ethylidene]-2-thioxo-dihydro-pyrimidine-4,6-dione;

Chemical name;

1-butyl-5-[2-(6-ethoxy-3-hexyl-3H-benzothiazole -2-ilidene)-ethylidene]-3-(2-methoxy-ethyl)-pyrimidine -2,4,6-trione.

19. A method of producing a volume hologram according to claim 9, wherein a volume hologram having a diffraction efficiency of 80% or more can be obtained.

20. A photosensitive composition for volume hologram recording comprising a photopolymerizable compound as a refractive index modulation component, a photopolymerization initiator, a sensitizing dye which increases sensitivity of the photopolymerization initiator with respect to a wavelength of a visible region and a binder resin and/or a thermosetting compound, wherein the composition itself has absorption at a predetermined volume hologram recording wavelength set in a visible region and the sensitizing dye is a cyclopentanone skeleton containing compound represented by the following general formula (1):

wherein, “

R”

is a carbon-nitrogen containing substituent represented by “

N_xC_y”

in which x=1 to 4, y=8 to 30;

“

R”

may contain a hydrogen atom and/or a halogen atom;

“

n”

is an integer of 0 to 3.

21. A photosensitive composition for volume hologram recording according to claim 20, wherein the photopolymerization initiator is a compound containing diaryliodonium skeleton represented by the following general formula (2):

wherein, each of “

X₁” and

“

X₂”

is independently an alkyl group having 1 to 20 carbons, halogen or an alkoxyl group having 1 to 20 carbons;

“

Y⁻

”

is a monovalent anion.

22. A photosensitive composition for volume hologram recording according to claim 20, wherein the photopolymerizable compound is at least one kind selected from the group consisting of a photoradical polymerizable compound and a photocationic polymerizable compound.

23. A photosensitive composition for volume hologram recording according to claim 20, wherein the photosensitive composition for volume hologram recording further contains a second refractive index modulation component having different refractive index from the photopolymerizable compound.

24. A photosensitive composition for volume hologram recording according to claim 20, wherein a volume hologram having a diffraction efficiency of 80% or more can be obtained.

25. A photosensitive composition for volume hologram recording comprising a photopolymerizable compound as a refractive index modulation component, a photopolymerization initiator, a sensitizing dye which increases sensitivity of the photopolymerization initiator with respect to a wavelength of a visible region and a binder resin and/or a thermosetting compound, wherein the composition itself has absorption at a predetermined volume hologram recording wavelength set within a region of 514 nm to 560 nm and the sensitizing dye is selected from a group consisting of the following compounds (3) and (4):

Chemical name;

2,5-bis(4-diethylaminobenzylidene)cyclopentanone;

Chemical name;

2,5-bis(4-dibutylaminobenzylidene)cyclopentanone.

26. A photosensitive composition for volume hologram recording according to claim 25, wherein the photopolymerization initiator is a compound containing diaryliodonium skeleton represented by the following general formula (2):

wherein, each of “

X₁” and

“

X₂”

is independently an alkyl group having 1 to 20 carbons, halogen or an alkoxyl group having 1 to 20 carbons;

“

Y⁻

”

is a monovalent anion.

27. A photosensitive composition for volume hologram recording according to claim 25, wherein the photopolymerizable compound is at least one kind selected from the group consisting of a photoradical polymerizable compound and a photocationic polymerizable compound.

28. A photosensitive composition for volume hologram recording according to claim 25, wherein the photosensitive composition for volume hologram recording further contains a second refractive index modulation component having different refractive index from the photopolymerizable compound.

29. A photosensitive composition for volume hologram recording according to claim 25, wherein a volume hologram having a diffraction efficiency of 80% or more can be obtained.

30. A photosensitive composition for volume hologram recording comprising a photopolymerizable compound as a refractive index modulation component, a photopolymerization initiator, a sensitizing dye which increases sensitivity of the photopolymerization initiator with respect to a wavelength of a visible region and a binder resin and/or a thermosetting compound, wherein the composition itself has absorption at a predetermined volume hologram recording wavelength set within a region of 630 nm to 670 nm and the sensitizing dye is selected from a group consisting of the following compounds (1) and (2):

Chemical name;

2-[[3-allyl-5-[2-(5,6-dimethyl-3-propyl-2(3H) -benzothiazolylidene)ethylidene]-4-oxo-2-thiazolidinylidene]methyl]-3-ethyl-4,5-diphenylthiazolium methylsulfate;

Chemical name;

1-heptyl-2-[3-(1-heptyl-5-methoxy-3,3-dimethyl -1,3-dihydro-indole-2-ilidenemethyl)-2-hydroxy-4-oxo-2-cyclobutenylidenemethyl]-5-methoxy-3,3-dimethyl-3H-indolium inner salt.

31. A photosensitive composition for volume hologram recording according to claim 30, wherein the photopolymerization initiator is a compound containing diaryliodonium skeleton represented by the following general formula (2):

wherein, each of “

X₁” and

“

X₂”

is independently an alkyl group having 1 to 20 carbons, halogen or an alkoxyl group having 1 to 20 carbons;

“

Y⁻

”

is a monovalent anion.

32. A photosensitive composition for volume hologram recording according to claim 30, wherein the photopolymerizable compound is at least one kind selected from the group consisting of a photoradical polymerizable compound and a photocationic polymerizable compound.

33. A photosensitive composition for volume hologram recording according to claim 30, wherein the photosensitive composition for volume hologram recording further contains a second refractive index modulation component having different refractive index from the photopolymerizable compound.

34. A photosensitive composition for volume hologram recording according to claim 30, wherein a volume hologram having a diffraction efficiency of 80% or more can be obtained.

35. A photosensitive composition for volume hologram recording comprising a photopolymerizable compound as a refractive index modulation component, a photopolymerization initiator, a sensitizing dye which increases sensitivity of the photopolymerization initiator with respect to a wavelength of a visible region and a binder resin and/or a thermosetting compound, wherein the composition itself has absorption at a predetermined volume hologram recording wavelength set within a region of 420 nm to 488 nm and the sensitizing dye is selected from a group consisting of the following compounds (5) and (6):

Chemical name;

1,3-diethyl-5-[2-(1-methyl-pyrrolidine-2-ilidene)-ethylidene]-2-thioxo-dihydro-pyrimidine-4,6-dione;

Chemical name;

1-butyl-5-[2-(6-ethoxy-3-hexyl-3H-benzothiazole -2-ilidene)-ethylidene]-3-(2-methoxy-ethyl)-pyrimidine -2,4,6-trione.

36. A photosensitive composition for volume hologram recording according to claim 35, wherein the photopolymerization initiator is a compound containing diaryliodonium skeleton represented by the following general formula (2):

wherein, each of “

X₁” and

“

X₂”

is independently an alkyl group having 1 to 20 carbons, halogen or an alkoxyl group having 1 to 20 carbons;

“

Y⁻

”

is a monovalent anion.

37. A photosensitive composition for volume hologram recording according to claim 35, wherein the photopolymerizable compound is at least one kind selected from the group consisting of a photoradical polymerizable compound and a photocationic polymerizable compound.

38. A photosensitive composition for volume hologram recording according to claim 35, wherein the photosensitive composition for volume hologram recording further contains a second refractive index modulation component having different refractive index from the photopolymerizable compound.

39. A photosensitive composition for volume hologram recording according to claim 35, wherein a volume hologram having a diffraction efficiency of 80% or more can be obtained.