JP4367074B2 - Hologram recording composition and hologram recording medium - Google Patents
Hologram recording composition and hologram recording medium Download PDFInfo
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- JP4367074B2 JP4367074B2 JP2003346041A JP2003346041A JP4367074B2 JP 4367074 B2 JP4367074 B2 JP 4367074B2 JP 2003346041 A JP2003346041 A JP 2003346041A JP 2003346041 A JP2003346041 A JP 2003346041A JP 4367074 B2 JP4367074 B2 JP 4367074B2
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- JP
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- Prior art keywords
- group
- ring
- hologram recording
- hologram
- polymerizable
- Prior art date
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Images
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Description
本発明は、重合性化合物を含むホログラム記録用組成物及びそれを用いたホログラム記録媒体に関するものであり、該記録媒体は干渉縞を記録層内部の屈折率差で記録するものである。 The present invention relates to a hologram recording composition containing a polymerizable compound and a hologram recording medium using the composition, and the recording medium records interference fringes with a difference in refractive index inside a recording layer.
ホログラムは2つの干渉縞が作るパタンを感光材料に記録し、これに参照光と同じ方向から同じレーザ光を照射すると、被写体があった位置に被写体とそっくりの立体像が再生されて見える、というものである。このホログラム技術は、三次元画像表示装置や回折光学素子、及び大容量メモリの分野で期待されている。
ホログラムは干渉縞の記録形態により幾つかの種類に分類される。近年、干渉縞を記録層内部の屈折率差で記録するいわゆる位相ホログラムが、その高い回折効率や優れた波長選択性により、三次元ディスプレイや光学素子、及び大容量メモリなどの用途に応用されつつある。
The hologram records a pattern created by two interference fringes on a photosensitive material, and when this is irradiated with the same laser light from the same direction as the reference light, a three-dimensional image that looks exactly like the subject appears to be reproduced at the position where the subject was located. Is. This hologram technology is expected in the fields of three-dimensional image display devices, diffractive optical elements, and large-capacity memories.
Holograms are classified into several types according to the recording pattern of interference fringes. In recent years, so-called phase holograms that record interference fringes with a refractive index difference inside a recording layer are being applied to applications such as three-dimensional displays, optical elements, and large-capacity memories due to their high diffraction efficiency and excellent wavelength selectivity. is there.
このような屈折率差を利用したホログラム用記録材料としては、各種検討がなされている。フォトポリマーもその一例で、それらに用いられる光重合性モノマーとして、高屈折率を目指した芳香環を含むモノマー、例えば、ビニルカルバゾール等のカルバゾール系化合物が用いられることも知られている(特許文献1)。
しかしながら、従来知られているホログラム記録材料は、屈折率変化や感度の点で未だ不十分であり、より優れたモノマーの出現が望まれている。
However, conventionally known hologram recording materials are still insufficient in terms of refractive index change and sensitivity, and the appearance of better monomers is desired.
本発明の目的は、回折効率が高く、高感度なホログラム用組成物を提供することにある。また、本発明の別の目的は、該組成物を用いたホログラム記録媒体を提供するものである。 An object of the present invention is to provide a hologram composition having high diffraction efficiency and high sensitivity. Another object of the present invention is to provide a hologram recording medium using the composition.
本発明者らは、上記課題を解決するために鋭意検討した結果、(メタ)アクリロイル基、オキシラニル基等の重合性基を有する硫黄原子含有縮合芳香環化合物が屈折率変化が大きく、優れたホログラム記録用組成物となることを見い出し、本発明を完成するに至った。
すなわち本発明の要旨は、可干渉性な光の干渉による干渉縞を屈折率の差によって記録する体積ホログラム記録用組成物であって、下記一般式(1)で表される重合性硫黄原子含有化合物を含むことを特徴とするホログラム記録用組成物に存する。
As a result of intensive studies to solve the above problems, the present inventors have found that a sulfur atom-containing condensed aromatic ring compound having a polymerizable group such as a (meth) acryloyl group or an oxiranyl group has a large refractive index change and has an excellent hologram. The inventors have found that the composition is a recording composition and have completed the present invention.
That is, the gist of the present invention is a volume hologram recording composition for recording interference fringes due to interference of coherent light by a difference in refractive index, which contains a polymerizable sulfur atom represented by the following general formula (1) It exists in the composition for hologram recording characterized by including a compound.
(式中、XはNまたはCHであり、環Aは置換基を有していても良い芳香環であり、R2はアルケニル基、(メタ)アクリロイル基、オキシラニル基、チイラニル基、及びエチレンイミノ基からなる群から選ばれる重合性基を含有する基である。但しX=CHの時、環Aはチオフェン環類ではない。)
(Wherein X is N or CH, ring A is an aromatic ring which may have a substituent, and R 2 is an alkenyl group, a (meth) acryloyl group, an oxiranyl group, a thiranyl group, and an ethyleneimino group. A group containing a polymerizable group selected from the group consisting of groups, provided that when X = CH, ring A is not a thiophene ring.)
本発明は、重合性硫黄原子含有縮合芳香環化合物を用いることにより回折効率と感度が高いホログラム記録材料と記録媒体を製造することができる。 The present invention can produce a hologram recording material and a recording medium having high diffraction efficiency and sensitivity by using a polymerizable sulfur atom-containing fused aromatic ring compound.
以下、本発明をさらに詳細に説明する。
(重合性硫黄原子含有化合物)
本発明のホログラム記録用組成物は、下記一般式(1)で表される重合性硫黄原子含有化合物を含むものである。
Hereinafter, the present invention will be described in more detail.
(Polymerizable sulfur atom-containing compound)
The hologram recording composition of the present invention contains a polymerizable sulfur atom-containing compound represented by the following general formula (1).
(式中、XはNまたはCHであり、環Aは置換基を有していても良い芳香環であり、R2
は重合性基を含有する基である。但しX=CHの時、環Aはチオフェン環類ではない。)
上記環Aは芳香環であれば特に限定はなく、炭化水素環でも複素環でも良い。又、単環でも縮合環でも良い。具体的にはベンゼン環、ペンタレン環、インデン環、ナフタレン環、アズレン環、ヘプタレン環、ビフェニレン環、インダセン環、アセナフチレン環、フルオレン環、フェナレン環、フェナントレン環、アントラセン環、フルオランテン環、アセフェナンスリレン環、アセアンスリレン環、トリフェニレン環、ピレン環、クリセン環、テトラセン環、ベンゾ[a]アントラセン環、プレイアデン環、ペリレン環、ピセン環、ベンゾ[a]ピレン環、ペンタフェン環、ペンタセン環、テトラフェニレン環、ヘキサフェン環、ヘキサセン環、ルビセン環、コロネン環、トリナフチレン環、ヘプタフェン環、ヘプタセン環、ピランスレン環、オバレン環等の炭化水素系の芳香環;チオフェン環、ベンゾチオフェン環、ナフトチオフェン環、チイン環、チアントレン環等の硫黄原子含有複素芳香環;フラン環、ベンゾフラン環、イソベンゾフラン環、ジベンゾフラン環、ピラン環、ベンゾピラン環、キサンテン環、クロメン環、キサンテン環、フェノキサチン環、イソクロマン環、クロマン環等の酸素原子含有複素芳香環;ピロール環、イミダゾール環、ピラゾール環、トリアゾール環、テトラゾール環、ベンゾイミダゾール環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、トシアジン環、インドリジン環、イソインドール環、インドール環、インダゾール環、ピュリン環、キノリジン環、イソキノリン環、キノリン環、フタラジン環、ナフチリジン環、キノキサリン環、キナゾリン環、シンノリン環、プテリジン環、カルバゾール環、カルボリン環、フェナントリジン環、アクリジン環、ペリミジン環、フェナンスロリン環、フェナジン環、フェナルサジン環、テリジン環等の窒素原子含有複素芳香環;イソチアゾール環、チアゾール環、ベンゾチアゾール環、チアジン環、フェノチアジン環等の硫黄窒素原子含有複素芳香環;イソオキサゾール環、オキサゾール環、ベンゾオキサゾール環、フラザン環、オキサジン環、フェノキサジン環等の酸素窒素原子含有複素芳香環等の複素芳香環等が挙げられる。
(Wherein X is N or CH, ring A is an aromatic ring which may have a substituent, and R 2
Is a group containing a polymerizable group. However, when X = CH, ring A is not a thiophene ring. )
The ring A is not particularly limited as long as it is an aromatic ring, and may be a hydrocarbon ring or a heterocyclic ring. Further, it may be a single ring or a condensed ring. Specifically, benzene ring, pentalene ring, indene ring, naphthalene ring, azulene ring, heptalene ring, biphenylene ring, indacene ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, fluoranthene ring, acephenanthrylene Ring, aseanthrylene ring, triphenylene ring, pyrene ring, chrysene ring, tetracene ring, benzo [a] anthracene ring, preaden ring, perylene ring, picene ring, benzo [a] pyrene ring, pentaphen ring, pentacene ring, tetra Hydrocarbon aromatic rings such as phenylene ring, hexaphen ring, hexacene ring, rubicene ring, coronene ring, trinaphthylene ring, heptaphen ring, heptacene ring, pyranthrene ring, ovalen ring; thiophene ring, benzothiophene ring, naphthothiophene ring, thiyne ring Sulfur atom-containing heteroaromatic ring such as thianthrene ring; oxygen such as furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, pyran ring, benzopyran ring, xanthene ring, chromene ring, xanthene ring, phenoxatin ring, isochroman ring, chroman ring Atom-containing heteroaromatic ring: pyrrole ring, imidazole ring, pyrazole ring, triazole ring, tetrazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, tocazine ring, indolizine ring, isoindole ring, indole ring , Indazole ring, purine ring, quinolidine ring, isoquinoline ring, quinoline ring, phthalazine ring, naphthyridine ring, quinoxaline ring, quinazoline ring, cinnoline ring, pteridine ring, carbazole ring, carboline ring, phenanthridine ring, a Nitrogen-containing heteroaromatic rings such as lysine ring, perimidine ring, phenanthroline ring, phenazine ring, phenalsazine ring, and teridine ring; sulfur nitrogen atoms such as isothiazole ring, thiazole ring, benzothiazole ring, thiazine ring, and phenothiazine ring Heteroaromatic rings; heteroaromatic rings such as oxygen-nitrogen atom-containing heteroaromatic rings such as isoxazole ring, oxazole ring, benzoxazole ring, furazane ring, oxazine ring, phenoxazine ring and the like.
但し、X=CHの時、環Aはチオフェン環類ではない。チオフェン環類とは、チオフェン環、縮合チオフェン環、複数のチオフェン環及び/又は縮合チオフェン環が単結合で連結されている環、複数のチオフェン環及び/又は縮合チオフェン環が連結基を介して複数結合した環である。
環Aの芳香環として好ましいのは、単環又は縮合数2〜4の縮合環で、より好ましくは単環又は縮合数2の縮合環、特に好ましくは単環、最も好ましくはベンゼン環である。
However, when X = CH, ring A is not a thiophene ring. A thiophene ring is a thiophene ring, a fused thiophene ring, a ring in which a plurality of thiophene rings and / or fused thiophene rings are linked by a single bond, a plurality of thiophene rings and / or a plurality of fused thiophene rings via a linking group A linked ring.
Preferred as the aromatic ring of ring A is a single ring or a condensed ring having 2 to 4 condensations, more preferably a single ring or a condensed ring having 2 condensations, particularly preferably a single ring, and most preferably a benzene ring.
上記芳香環は、置換基を有していても良い。置換基は一価の基であれば特に限定されないが、具体的には、フッ素原子、塩素原子、臭素原子等のハロゲン原子;ニトロ基;ニトロソ基;シアノ基;イソシアノ基;シアナト基;イソシアナト基;チオシアナト基;イソチオシアナト基;メルカプト基;ヒドロキシ基;ホルミル基;スルホン酸基;カルボキシル基;置換されていても良いアルキル基;置換されていても良いアルケニル基;置換されていても良いアリール基;置換されていても良い複素環基;置換されていても良いアルコキシ基;置換されていても良いアルケニルオキシ基;置換されていても良いアリールオキシ基;置換されていても良いアルキルチオ基;−COQ9で表されるアシル基;−OCO
Q9で表されるアシルオキシ基;−NQ10Q11で表されるアミノ基;−COOQ9で表されるカルボン酸エステル基;−CONQ12Q13で表されるカルバモイル基;−SOQ9で表
されるスルフィニル基;−SO2Q9で表されるスルホニル基;−SO3Q9スルホン酸エステル基;−SO2NQ12Q13で表されるスルファモイル基が挙げられる。このうち、置換
されていても良いアルキル基;置換されていても良いアルケニル基;置換されていても良いアリール基;置換されていても良い複素環基;置換されていても良いアルコキシ基;置換されていても良いアルケニルオキシ基;置換されていても良いアリールオキシ基;置換されていても良いアルキルチオ基;−COQ9で表されるアシル基;−OCOQ9で表されるアシルオキシ基;−NQ10Q11で表されるアミノ基;−COOQ9で表されるカルボン
酸エステル基;−CONQ12Q13で表されるカルバモイル基;−SOQ9で表されるスル
フィニル基;−SO2Q9で表されるスルホニル基;−SO3Q9スルホン酸エステル基;−SO2NQ12Q13で表されるスルファモイル基としては、炭素数18以下、好ましくは1
2以下ものが挙げられる。
The aromatic ring may have a substituent. The substituent is not particularly limited as long as it is a monovalent group, and specifically, a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom; a nitro group; a nitroso group; a cyano group; an isocyano group; a cyanato group; A thiocyanato group; an isothiocyanato group; a mercapto group; a hydroxy group; a formyl group; a sulfonic acid group; a carboxyl group; an optionally substituted alkyl group; an optionally substituted alkenyl group; an optionally substituted aryl group; An optionally substituted heterocyclic group; an optionally substituted alkoxy group; an optionally substituted alkenyloxy group; an optionally substituted aryloxy group; an optionally substituted alkylthio group; An acyl group represented by 9 ;
Table with -SOQ 9; carbamoyl groups represented by -CONQ 12 Q 13; carboxylic acid ester group represented by -COOQ 9; amino group represented by -NQ 10 Q 11; acyloxy group represented by Q 9 A sulfinyl group represented by —SO 2 Q 9 ; a sulfoyl group represented by —SO 3 Q 9 sulfonic acid ester group; a —sulfoyl group represented by —SO 2 NQ 12 Q 13 . Among them, an alkyl group which may be substituted; an alkenyl group which may be substituted; an aryl group which may be substituted; a heterocyclic group which may be substituted; an alkoxy group which may be substituted; are good alkenyloxy group optionally; acyloxy group represented by -OCOQ 9;; acyl group represented by -COQ 9; alkylthio group which may be substituted; aryl group which may be substituted -NQ sulfinyl group represented by -SOQ 9;; carboxylic acid represented by -COOQ 9 ester groups;; 10 Q 11 amino group represented by -CONQ 12 Q carbamoyl group represented by 13 in -SO 2 Q 9 As the sulfamoyl group represented by —sulfonyl group represented by —SO 3 Q 9 sulfonate group; —SO 2 NQ 12 Q 13 , preferably 18 or less, preferably 1
2 or less are mentioned.
上記アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、シクロプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、n−へプチル基、シクロペンチル基、シクロヘキシル基、アダマンチル基等の直鎖状、分岐鎖状もしくは環状のアルキル基が挙げられる。
上記アルケニル基としては、ビニル基、プロペニル基、シクロペンテニル基、ヘキセニル基、シクロヘキセニル基等の直鎖状、分岐鎖状もしくは環状のアルケニル基が挙げられる。
Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-heptyl group, cyclopentyl group, cyclohexyl group, and adamantyl. Examples thereof include linear, branched or cyclic alkyl groups such as groups.
Examples of the alkenyl group include linear, branched or cyclic alkenyl groups such as vinyl group, propenyl group, cyclopentenyl group, hexenyl group and cyclohexenyl group.
上記アリール基としては、フェニル基、ナフチル基、又はアントラニル基等の単環もしくは縮合環のアリール基が挙げられる。
上記複素環基としては、前記芳香環の説明で挙げたような複素芳香環の1価の基や、環状エーテル、ラクトン、環式イミン、ラクタム等の複素環の1価の基が挙げられる。
上記アルコキシ基としては、メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、sec−ブトキシ基、tert−ブトキシ基等の直鎖状、分岐鎖状もしくは環状のアルコキシ基が挙げられる。
Examples of the aryl group include monocyclic or condensed ring aryl groups such as a phenyl group, a naphthyl group, and an anthranyl group.
Examples of the heterocyclic group include monovalent groups of heteroaromatic rings as mentioned in the description of the aromatic ring, and monovalent groups of heterocyclic rings such as cyclic ethers, lactones, cyclic imines, and lactams.
Examples of the alkoxy group include linear, branched or cyclic alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, and tert-butoxy group. Can be mentioned.
上記アルケニルオキシ基としてはプロペニルオキシ基、ブテニルオキシ基、ペンテニルオキシ基等の直鎖状、分岐鎖状もしくは環状のアルケニルオキシ基が挙げられる。
上記アリールオキシ基としては、フェノキシ基、ナフチルオキシ基、又はアントラニルオキシ基等の単環もしくは縮合環のアリールオキシ基が挙げられる。
上記アルキルチオ基としては、メチルチオ基、エチルチオ基、n−プロピルチオ基、n−ブチルチオ基、sec−ブチルチオ基、tert−ブチルチオ基等の直鎖状、分岐鎖状もしくは環状のアルキルチオ基が挙げられる。
Examples of the alkenyloxy group include linear, branched or cyclic alkenyloxy groups such as a propenyloxy group, a butenyloxy group, and a pentenyloxy group.
Examples of the aryloxy group include monocyclic or condensed aryloxy groups such as a phenoxy group, a naphthyloxy group, and an anthranyloxy group.
Examples of the alkylthio group include linear, branched or cyclic alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, n-butylthio group, sec-butylthio group, and tert-butylthio group.
上記アシル基、アシルオキシ基、カルボン酸エステル基、スルフィニル基、スルホニル基及びスルホン酸エステル基におけるQ9としては、置換されていても良い炭化水素基又
は置換されていても良い複素環基が挙げられる。
上記アミノ基におけるQ10及びQ11としては、それぞれ独立して、水素原子、水酸基、炭化水素基、複素環基、−COQ9で表されるアシル基、−COOQ9で表されるカルボン酸エステル基又は−SO2Q9で表されるスルホニル基が挙げられる。
Examples of Q 9 in the acyl group, acyloxy group, carboxylic acid ester group, sulfinyl group, sulfonyl group, and sulfonic acid ester group include an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group. .
The Q 10 and Q 11 in the amino group, each independently, a hydrogen atom, a hydroxyl group, a hydrocarbon group, a heterocyclic group, an acyl group represented by -COQ 9, carboxylic acid ester represented by -COOQ 9 And a sulfonyl group represented by —SO 2 Q 9 .
上記カルバモイル基又はスルファモイル基における、Q12及びQ13としては、それぞれ独立して、水素原子、炭化水素基又は複素環基が挙げられる。
上述の、Q9〜Q13の炭化水素基としては、アルキル基、アルケニル基、アリール基等
の炭化水素基が挙げられ、複素環基としては前記芳香環の説明で挙げたような複素芳香環の1価の基や、環状エーテル、ラクトン、環式イミン、ラクタム等の複素環の1価の基が挙げられる。
Examples of Q 12 and Q 13 in the carbamoyl group or sulfamoyl group independently include a hydrogen atom, a hydrocarbon group, or a heterocyclic group.
Examples of the hydrocarbon group of Q 9 to Q 13 include hydrocarbon groups such as an alkyl group, an alkenyl group, and an aryl group, and examples of the heterocyclic group include heteroaromatic rings as mentioned in the description of the aromatic ring. And monovalent groups of heterocyclic rings such as cyclic ethers, lactones, cyclic imines, and lactams.
上記アルキル基、アルケニル基、アリール基、複素環基、アルコキシ基、アルケニルオキシ基、アリールオキシ基、アルキルチオ基及び炭化水素基は、任意の置換されていても良く、その具体例としては、上述の芳香環の置換基の具体例として記述したような基が挙げられる。
このうち芳香環の置換基として好ましくは、ハロゲン原子、アルキル基、アルコキシ基又はアリール基である。さらに好ましくはハロゲン原子、C1〜C6の無置換のアルキル基、C1〜C6の無置換のアルコキシ基又はC1〜C6の炭化水素基で置換されていても良いアリール基、特に好ましくは、ハロゲン原子、C1〜C4の無置換のアルキル基、C1〜C4の無置換のアルコキシ基、又はC1〜C4の炭化水素基で置換されていても良いアリール基である。
置換基を含む環Aとして好ましいのは、下記一般式(1’)で表される環である。
The alkyl group, alkenyl group, aryl group, heterocyclic group, alkoxy group, alkenyloxy group, aryloxy group, alkylthio group and hydrocarbon group may be optionally substituted, and specific examples thereof include those described above. Examples include the groups described as specific examples of the substituent of the aromatic ring.
Of these, a substituent of the aromatic ring is preferably a halogen atom, an alkyl group, an alkoxy group or an aryl group. More preferably a halogen atom, an unsubstituted alkyl group, an unsubstituted alkoxy group or a C 1 -C 6 hydrocarbon optionally substituted aryl group with a group of C 1 -C 6 of C 1 -C 6, particularly preferably, halogen atom, an unsubstituted alkyl group of C 1 -C 4, an unsubstituted alkoxy group of C 1 -C 4, or C 1 -C 4 hydrocarbons may be substituted with an aryl group is there.
The ring A containing a substituent is preferably a ring represented by the following general formula (1 ′).
式中、R4〜R7はそれぞれ独立して、水素原子、ハロゲン原子、アルキル基、アルコキシ基又はアリール基である。さらに好ましくは、水素原子又はC1〜C4のアルキル基である。
上記、R2は重合性基を含有する基である。重合性基とは、重合可能な官能基であれば特に限定はしないが、好ましくはアルケニル基、(メタ)アクリロイル基、オキシラニル基、チイラニル基、及びエチレンイミノ基を含む基である。より好ましくはアルケニル基、(メタ)アクリロイル基の様なラジカル重合可能な官能基であり、特に好ましくは(メタ)アクリロイル基である。
In the formula, R4 to R7 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an aryl group. More preferably, they are a hydrogen atom or a C1-C4 alkyl group.
R2 is a group containing a polymerizable group. The polymerizable group is not particularly limited as long as it is a polymerizable functional group, but is preferably a group containing an alkenyl group, a (meth) acryloyl group, an oxiranyl group , a thiranyl group , and an ethyleneimino group. More preferred are functional groups capable of radical polymerization such as alkenyl groups and (meth) acryloyl groups, and particularly preferred are (meth) acryloyl groups.
該重合性基は、単独でR2となりうるが、さらに組成物及び/又は重合性硫黄原子含有
化合物の安定性に悪影響を与えない連結基と一体になりR2とすることもできる。連結基
としては、であれば特に限定されないが、好ましくは有機基であって、更に好ましくは置換されていても良いアルキレン基;置換されていても良いアルケニレン基;置換されても良いアルキニレン基;置換されていても良いアルキレンオキシ基;置換されていても良いアルケニレンオキシ基;置換されても良いアルキニレンオキシ基;置換されていても良い
アルキレンチオ基;置換されていても良いアルケニレンチオ基;置換されても良いアルキニレンチオ基、特に好ましくは炭素数1〜12のアルキレン基、アルキレンオキシ基、アルキレンチオ基が挙げられ、最も好ましくは炭素数1〜4のアルキレン基、アルキレンオキシ基、アルキレンチオ基である。
The polymerizable group can be R 2 alone, but can also be integrated with a linking group that does not adversely affect the stability of the composition and / or polymerizable sulfur atom-containing compound and can be R 2 . The linking group is not particularly limited, but is preferably an organic group, more preferably an alkylene group which may be substituted; an alkenylene group which may be substituted; an alkynylene group which may be substituted; An alkyleneoxy group that may be substituted; an alkenyleneoxy group that may be substituted; an alkynyleneoxy group that may be substituted; an alkylenethio group that may be substituted; an alkenylenethio group that may be substituted; An alkynylenethio group which may be substituted, particularly preferably an alkylene group having 1 to 12 carbon atoms, an alkyleneoxy group or an alkylenethio group, most preferably an alkylene group having 1 to 4 carbon atoms, an alkyleneoxy group or an alkylenethio group It is.
上記連結基は、置換基を有していても良く、置換基としては前記芳香環の置換基の説明で挙げられたものが使用できる。
上記R2としては、(メタ)アクリルアルキル基、(メタ)アクリルアルキルオキシ基
、(メタ)アクリルアルキルチオ基が好ましく、さらに好ましくは下記構造式で表される基である。
The linking group may have a substituent, and those exemplified in the description of the substituent of the aromatic ring can be used as the substituent.
R 2 is preferably a (meth) acrylalkyl group, a (meth) acrylalkyloxy group, or a (meth) acrylalkylthio group, and more preferably a group represented by the following structural formula.
又、重合性硫黄原子含有化合物は、有機溶媒に溶解性がある方が好ましく、具体的には、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、メチルアミルケトン等のケトン系溶剤;トルエン、キシレン等の芳香族系溶媒;メタノール、エタノール、プロパノール、n−ブタノール、ヘプタノール、ヘキサノール、ジアセトンアルコール、フルフリルアルコール等のアルコール系溶剤;テトラヒドロフラン、ジオキサン等のエーテル系溶媒;ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒;メチルセロソルブ、エチルセロソルブ、ブチルセロソルブ、メチルセロソルブアセテート、エチルセロソルブアセテート等のセロソルブ系溶剤;プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート、ジプロピレングリコールジメチルエーテル等のプロピレングリコール系溶剤;酢酸エチル、酢酸ブチル、酢酸アミル、酢酸ブチル、エチレングリコールジアセテート、ジエチルオキサレート、ピルビン酸エチル、エチル−2−ヒドロキシブチレートエチルアセトアセテート、乳酸メチル、乳酸エチル、3−メトキシプロピオン酸メチル等のエステル系溶剤;ジメチルホルムアミド、ジメチルアセトアミドN−メチルピロリドン等の高極性溶剤;あるいはこれらの混合溶剤に溶解する事が好ましい。 The polymerizable sulfur atom-containing compound is preferably soluble in an organic solvent. Specifically, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and methyl amyl ketone; toluene, xylene and the like Aromatic solvents: Alcohol solvents such as methanol, ethanol, propanol, n-butanol, heptanol, hexanol, diacetone alcohol and furfuryl alcohol; Ether solvents such as tetrahydrofuran and dioxane; Halogen systems such as dichloromethane, dichloroethane and chloroform Solvent: Cellosolve solvents such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate; propylene glycol monomethyl ether, propylene group Propylene glycol solvents such as coal monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether; ethyl acetate, butyl acetate, amyl acetate, acetic acid Ester solvents such as butyl, ethylene glycol diacetate, diethyl oxalate, ethyl pyruvate, ethyl-2-hydroxybutyrate ethyl acetoacetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate; dimethylformamide, dimethylacetamide N -It is preferable to dissolve in a highly polar solvent such as methylpyrrolidone; or a mixed solvent thereof.
これらの溶媒に対して、重合性硫黄原子含有化合物の溶解度は、2重量%以上であることが好ましく、さらに好ましくは10重量%以上である。
重合性硫黄原子含有化合物は、公知の方法に準じて又はそれらを組み合わせることにより製造することが出来る。
(ホログラム組成物)
本発明の組成物は、少なくとも重合性硫黄原子含有化合物と重合開始剤とを含有する。
重合性硫黄原子含有化合物の量は、通常全固形分の5〜99.9重量%であり、好ましくは10〜80重量%、より好ましくは20〜60重量%である。
重合開始剤としては、光ラジカル重合開始剤であるのが望ましい。光ラジカル重合開始剤は、ホログラム作製のための第一露光用の光によって、活性ラジカルを生成する。
重合開始剤は公知のラジカル重合開始剤であればいずれも用いることができ、例えば、アゾ系化合物、アジド系化合物、有機過酸化物、有機硼素酸塩、オニウム塩類、ビスイミ
ダゾール誘導体、チタノセン化合物、ヨードニウム塩類、有機チオール化合物、ハロゲン化炭化水素誘導体等が用いられる。これらの内、チタノセン化合物が好ましい。
The solubility of the polymerizable sulfur atom-containing compound with respect to these solvents is preferably 2% by weight or more, and more preferably 10% by weight or more.
The polymerizable sulfur atom-containing compound can be produced according to a known method or by combining them.
(Hologram composition)
The composition of the present invention contains at least a polymerizable sulfur atom-containing compound and a polymerization initiator.
The amount of the polymerizable sulfur atom-containing compound is usually 5 to 99.9% by weight of the total solid content, preferably 10 to 80% by weight, more preferably 20 to 60% by weight.
The polymerization initiator is preferably a radical photopolymerization initiator. The photo radical polymerization initiator generates active radicals by light for first exposure for producing a hologram.
Any polymerization initiator can be used as long as it is a known radical polymerization initiator. For example, azo compounds, azide compounds, organic peroxides, organic borates, onium salts, bisimidazole derivatives, titanocene compounds, Iodonium salts, organic thiol compounds, halogenated hydrocarbon derivatives and the like are used. Of these, titanocene compounds are preferred.
該チタノセン化合物は、特に限定はされないが例えば特開昭59−152396号、特開昭61−151197号各公報等に記載されている各種チタノセン化合物から適宜選んで用いることができる。さらに具体的には、ジ−シクロペンタジエニル−Ti−ジ−クロライド、ジ−シクロペンタジエニル−Ti−ビス−フェニル、ジ−シクロペンタジエニル−Ti−ビス−2,3,4,5,6−ペンタフルオロフェニ−1−イル、ジシクロペンタジエニル−Ti−ビス−2,3,5,6−テトラフルオロフェニ−1−イル、ジ−シクロペンタジエニル−Ti−ビス−2,4,6−トリフルオロフェニ−1−イル、ジ−シクロペンタジエニル−Ti−ビス−2,6−ジ−フルオロフェニ−1−イル、ジ−シクロペンタジエニル−Ti−ビス−2,4−ジ−フルオロフェニ−1−イル、ジ−メチルシクロペンタジエニル−Ti−ビス−2,3,4,5,6−ペンタフルオロフェニ−1−イル、ジ−メチルシクロペンタジエニル−Ti−ビス−2,3,5,6−テトラフルオロフェニ−1−イル、ジ−メチルシクロペンタジエニル−Ti−ビス−2,6−ジフルオロフェニ−1−イル、ジ−シクロペンタジエニル−Ti−ビス−2,6−ジフルオロ−3−(ピリ−1−イル)−フェニ−1−イル等を挙げることができる。
特には、以下に示すジ−シクロペンタジエニル−Ti−ビス−2,6−ジフルオロ−3−(ピリ−1−イル)−フェニ−1−イルが好ましい。
The titanocene compound is not particularly limited, and can be appropriately selected from various titanocene compounds described in, for example, JP-A Nos. 59-152396 and 61-151197. More specifically, di-cyclopentadienyl-Ti-di-chloride, di-cyclopentadienyl-Ti-bis-phenyl, di-cyclopentadienyl-Ti-bis-2,3,4,5 , 6-pentafluorophen-1-yl, dicyclopentadienyl-Ti-bis-2,3,5,6-tetrafluorophen-1-yl, di-cyclopentadienyl-Ti-bis-2, 4,6-trifluorophen-1-yl, di-cyclopentadienyl-Ti-bis-2,6-di-fluorophen-1-yl, di-cyclopentadienyl-Ti-bis-2,4 -Di-fluorophen-1-yl, di-methylcyclopentadienyl-Ti-bis-2,3,4,5,6-pentafluorophen-1-yl, di-methylcyclopentadienyl-Ti- Bis-2, 3 5,6-tetrafluorophen-1-yl, di-methylcyclopentadienyl-Ti-bis-2,6-difluorophen-1-yl, di-cyclopentadienyl-Ti-bis-2,6- Difluoro-3- (pyrid-1-yl) -phen-1-yl and the like can be mentioned.
In particular, di-cyclopentadienyl-Ti-bis-2,6-difluoro-3- (pyrid-1-yl) -phen-1-yl shown below is preferable.
重合開始剤はいずれか一種を単独で用いても良く、2種以上を併用しても良い。重合開始剤の量は、全固形分の0.1重量%から10重量%が好ましい。より、好ましくは、0.5重量%から5重量%である。0.1重量%より少ないとラジカルの発生量が少なくなるため、光重合の速度が遅くなり、ホログラム記録感度が低くなる。10重量%より多いと光照射により発生したラジカル同士が再結合し、光重合に対する寄与が少なくなり、やはりホログラム記録感度が低下する場合がある。また、干渉縞の明部において分子量の低いポリマーが均一に生成されるため、明部と暗部とのモノマー濃度差が小さくなり、そのためモノマーの効果的な拡散ができず、回折効率が上がらない場合もある。 Any one polymerization initiator may be used alone, or two or more polymerization initiators may be used in combination. The amount of the polymerization initiator is preferably 0.1% by weight to 10% by weight based on the total solid content. More preferably, it is 0.5 to 5% by weight. If the amount is less than 0.1% by weight, the amount of radicals generated is reduced, so that the rate of photopolymerization is reduced and the hologram recording sensitivity is lowered. When the amount is more than 10% by weight, radicals generated by light irradiation are recombined to reduce contribution to photopolymerization, and the hologram recording sensitivity may be lowered. In addition, since the polymer with low molecular weight is uniformly generated in the bright part of the interference fringe, the monomer concentration difference between the bright part and the dark part becomes small, so that the monomer cannot be effectively diffused and the diffraction efficiency does not increase. There is also.
本発明の光ラジカル重合開始剤は、単独で用いても良いが、光を吸収する成分である増感剤と組み合わせて用いてもよい。
好ましい増感剤の具体例としては、例えば、特開平5−241338号公報に記載されている2,6−ジエチル−1,3,5,7,8−ペンタメチルピロメテン−BF2錯体及
び1,3,5,7,8−ペンタメチルピロメテン−BF2錯体の様なピロメテン錯体;エ
オシン、エチルエオシン、エリスロシン、フルオレセイン、及びローズベンガルの様なキサンテン系色素;特開平2−69号公報に記載されている1−(1−メチルナフト〔1,
2−d〕チアゾール−2(1H)−イリデン−4−(2,3,6,7)テトラヒドロ−1H,5H−ベンゾ〔ij〕キノリジン−9−イル)−3−ブテン−2−オン、及び1−(3−メチルベンゾチアゾール−2(3H)−イリデン−4−(p−ジメチルアミノフェニル)−3−ブテン−2−オンの様なケトチアゾリン系化合物;特公平2−55446号、特公平2−30321号各公報に記載された2−(p−ジメチルアミノスチリル)−ナフト〔1,2−d〕チアゾール、及び2−〔4−(p−ジメチルアミノフェニル)−1,3−ブタジエニル〕−ナフト〔1,2−d〕チアゾールの様なスチリルまたはフェニルブタジエニル複素環化合物;2,4−ジフェニル−6−(p−ジメチルアミノスチリル)−1,3,5−トリアジン、及び2,4−ジフェニル−6−((〔2,3,6,7〕テトラヒドロ−1H,5H−ベンゾ〔ij〕キノリジン−9−イル)−1−エテン−2−イル)−1,3,5−トリアジンの様なトリアジン系化合物;特開平6−116313、特開昭47−2528号公報等に記載されているナンスリル−((〔2,3,6,7〕テトラヒドロ−1H,5H−ベンゾ〔ij〕キノリジン−9−イル)−1−エテン−2−イル)ケトン、及び2,5−ビス(p−ジメチルアミノシンナミリデン)シクロペンタノンの様なアミノフェニル不飽和ケトン化合物;5,10,15,20テトラフェニルポルフィリン、ヘマトポリフィリンの様なポリフィリン類等を挙げることができる。以上、好適な増感剤を例示したが、これらの内、特にピロメテン錯体が好ましい。
Although the radical photopolymerization initiator of the present invention may be used alone, it may be used in combination with a sensitizer that is a component that absorbs light.
Specific examples of preferable sensitizers include 2,6-diethyl-1,3,5,7,8-pentamethylpyromethene-BF 2 complex and 1 described in JP-A-5-241338. , 3,5,7,8-pentamethylpyromethene-BF 2 complex; pyromethene complex; eosin, ethyl eosin, erythrosine, fluorescein, xanthene dyes such as rose bengal; The described 1- (1-methylnaphtho [1,
2-d] thiazol-2 (1H) -ylidene-4- (2,3,6,7) tetrahydro-1H, 5H-benzo [ij] quinolizin-9-yl) -3-buten-2-one, and Ketothiazoline compounds such as 1- (3-methylbenzothiazole-2 (3H) -ylidene-4- (p-dimethylaminophenyl) -3-buten-2-one; Japanese Patent Publication No. 2-55446, Japanese Patent Publication No. 2 2- (p-dimethylaminostyryl) -naphtho [1,2-d] thiazole and 2- [4- (p-dimethylaminophenyl) -1,3-butadienyl]-described in each publication No. 30321 A styryl or phenylbutadienyl heterocyclic compound such as naphtho [1,2-d] thiazole; 2,4-diphenyl-6- (p-dimethylaminostyryl) -1,3,5-triazine, and , 4-Diphenyl-6-(([2,3,6,7] tetrahydro-1H, 5H-benzo [ij] quinolizin-9-yl) -1-ethen-2-yl) -1,3,5- Triazine compounds such as triazine; nansuryl-(([2,3,6,7] tetrahydro-1H, 5H-benzo [ij] described in JP-A-6-116313 and JP-A-47-2528 Quinolinidin-9-yl) -1-ethen-2-yl) ketone, and aminophenyl unsaturated ketone compounds such as 2,5-bis (p-dimethylaminocinnamylidene) cyclopentanone; Examples include 15,20 tetraphenylporphyrin, polyphyrins such as hematoporphyrin, etc. As mentioned above, preferred sensitizers are exemplified, but among these, pyromethene complex is particularly preferred. .
前記のように、増感剤は可視レーザ光を吸収するために色素のような有色化合物が用いられる場合が多いが、最終的なホログラムに無色透明性が要求される場合(例えば、自動車等のヘッドアップディスプレイとして使用する場合)の増感剤としては、特開昭58―29803号公報、特開平1−287105号公報、特開平3−5569号に記載されているようなシアニン系色素の使用が好ましい。 As described above, the sensitizer is often a colored compound such as a dye for absorbing visible laser light. However, when the final hologram requires colorless transparency (for example, in automobiles) As a sensitizer for use as a head-up display, use of a cyanine dye as described in JP-A-58-29803, JP-A-1-287105, and JP-A-3-5569 Is preferred.
また、光ラジカル重合開始剤としてチタノセン化合物を用いた場合には、増感剤としてはピロメテン化合物を用いることが好ましい。
増感剤の量は、使用する媒体の厚さによって増減する必要があるが、重合開始剤に対し重量比で0.01%から10%、好ましくは0.1%から5%である。
本発明の組成物には、エチレン性不飽和モノマーを混合する事もできる。該エチレン性不飽和化合物モノマーとは、光重合開始剤の作用により単独、あるいは重合性硫黄原子含有化合物と共に付加重合し、場合によって架橋、硬化するようなラジカル重合性のエチレン性不飽和結合を分子内に少なくとも1つ有する化合物である。なお、本発明におけるモノマーの意味するところは、所謂高分子物質に相対する概念であって、従って、狭義の単量体以外に二重体、三量体、オリゴマーをも包含するものである。
Further, when a titanocene compound is used as a photoradical polymerization initiator, it is preferable to use a pyromethene compound as a sensitizer.
The amount of the sensitizer needs to be increased or decreased depending on the thickness of the medium to be used, but is 0.01% to 10%, preferably 0.1% to 5% by weight relative to the polymerization initiator.
An ethylenically unsaturated monomer can also be mixed in the composition of the present invention. The ethylenically unsaturated compound monomer refers to a radically polymerizable ethylenically unsaturated bond that undergoes addition polymerization together with a polymerizable sulfur atom-containing compound by the action of a photopolymerization initiator, and in some cases crosslinks and cures. It is a compound having at least one in it. In addition, the meaning of the monomer in the present invention is a concept opposite to a so-called polymer substance, and therefore includes a dimer, a trimer, and an oligomer in addition to a monomer in a narrow sense.
エチレン性不飽和モノマーとしては例えば不飽和カルボン酸、不飽和カルボン酸のエステル、不飽和カルボン酸のアミド等が挙げられる。
不飽和カルボン酸としては、アクリル酸、メタクリル酸、マレイン酸等のエチレン性不飽和結合を有する脂肪族モノ又はポリカルボン酸が挙げられる。
不飽和カルボン酸とのエステルとしては、エチレングリコールジアクリレート、トリエチレングリコールジアクリレート、トリメチロールプロパントリアクリレート、トリメチロールエタントリアクリレート、ペンタエリスリトールジアクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、グリセロールアクリレート等のアクリル酸エステル、これら例示化合物のアクリレートをメタクリレートに代えたメタクリル酸エステル、同様にイタコネートに代えたイタコン酸エステル、クロトネートに代えたクロトン酸エステルもしくはマレエートに代えたマイレン酸エステル等の上記不飽和カルボン酸と脂肪族モノ又はポリヒドロキシ化合物とのエステル;ハイドロキノンジアクリレート、ハイドロキノンジメタクリレート、レゾルシンジアクリレート、レゾルシンジメタクリレート、ピロガロ
ールトリアクリレート等の上記不飽和カルボン酸と芳香族モノ又はポリヒドロキシ化合物とのエステル等が挙げられる。
Examples of the ethylenically unsaturated monomer include unsaturated carboxylic acids, esters of unsaturated carboxylic acids, amides of unsaturated carboxylic acids, and the like.
Examples of the unsaturated carboxylic acid include aliphatic mono- or polycarboxylic acids having an ethylenically unsaturated bond such as acrylic acid, methacrylic acid, and maleic acid.
Esters with unsaturated carboxylic acids include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylol ethane triacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipenta Acrylic acid esters such as erythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, glycerol acrylate, methacrylic acid esters in which the acrylates of these exemplary compounds are replaced by methacrylates, similarly itaconic acid esters in which itaconate is replaced, and crotonates Mai instead of crotonic acid ester or maleate Esters of the above unsaturated carboxylic acids such as acid esters with aliphatic mono- or polyhydroxy compounds; Unsaturated carboxylic acids such as hydroquinone diacrylate, hydroquinone dimethacrylate, resorcin diacrylate, resorcin dimethacrylate, pyrogallol triacrylate, and fragrance And esters with group mono- or polyhydroxy compounds.
上記不飽和カルボン酸とヒドロキシ化合物のエステルを、イソシアネート又は多価エポキシ化合物と付加反応したウレタン系化合物やエポキシ系化合物もエチレン性不飽和モノマーとして、使用することができる。
不飽和カルボン酸のアミドとしては エチレンビスアクリルアミド等のアクリルアミド類が挙げられる。
Urethane compounds and epoxy compounds obtained by addition reaction of the unsaturated carboxylic acid and the hydroxy compound with an isocyanate or a polyvalent epoxy compound can also be used as the ethylenically unsaturated monomer.
Examples of amides of unsaturated carboxylic acids include acrylamides such as ethylenebisacrylamide.
その他本発明に用いられるエチレン性不飽和モノマー化合物の例としてはフタル酸ジアリル等のアリルエステル類;ジビニルフタレート等のビニル基含有化合物などが有用である。
エチレン性不飽和モノマーの内、アクリル酸エステルまたはメタクリル酸エステルの単量体が特に好ましい。それぞれのエチレン性不飽和モノマーを単独で用いても良いし、必要に応じ混合して用いてもかまわない。
Other examples of the ethylenically unsaturated monomer compound used in the present invention include allyl esters such as diallyl phthalate; vinyl group-containing compounds such as divinyl phthalate.
Of the ethylenically unsaturated monomers, acrylate or methacrylate monomers are particularly preferred. Each ethylenically unsaturated monomer may be used alone, or may be used by mixing as necessary.
エチレン性不飽和モノマーの量は、エチレン性不飽和モノマーと重合性硫黄原子含有化合物の和に対して、重量比で0%から90%が好ましい。
本発明のホログラム記録用組成物には、必要に応じて、連鎖移動剤、可塑剤、着色剤等の添加剤を加えても良い。添加剤の量は全固形分に対して0〜20重量%、好ましくは0〜10重量%である。
The amount of the ethylenically unsaturated monomer is preferably 0% to 90% by weight with respect to the sum of the ethylenically unsaturated monomer and the polymerizable sulfur atom-containing compound.
If necessary, additives such as a chain transfer agent, a plasticizer, and a colorant may be added to the hologram recording composition of the present invention. The amount of the additive is 0 to 20% by weight, preferably 0 to 10% by weight, based on the total solid content.
また、膜厚の均一性を持たせ、光照射での重合で形成された干渉膜を安定に存在させるためには結合材としてバインダ樹脂を加えても良い。
バインダ樹脂は官能性モノマーと相溶性の良いものであれば良く、その具体例としては塩素化ポリエチレン、ポリメチル(メタ)クリレート、メチル(メタ)クリレートと他の(メタ)アクリル酸アルキルエステルの共重合体、塩化ビニルとアクリロニトリルの共重合体、ポリ酢酸ビニル、ポリビニルアルコール、ポリビニルホルマール、ポリビニルブチラール、ポリビニルピロリドン、エチルセルロース、アセチルセルロースなどが挙げられる。好ましくは、ポリメチルメタクリレートである。バインダ樹脂の量は、全固形分に対し重量比で0%から90%、好ましくは、40%から80%である。
(ホログラム記録媒体)
本発明のホログラム記録用組成物を用いてホログラム記録媒体を作るには無溶剤で支持体上に塗布するか、組成物に溶剤または添加剤を加えて混合してもよく、これを支持体上に塗布、乾燥して記録層を形成する。
In addition, a binder resin may be added as a binder in order to make the film thickness uniform and allow the interference film formed by polymerization by light irradiation to exist stably.
The binder resin only needs to have good compatibility with the functional monomer. Specific examples thereof include chlorinated polyethylene, polymethyl (meth) acrylate, methyl (meth) acrylate, and other (meth) acrylic acid alkyl esters. Examples thereof include copolymers, copolymers of vinyl chloride and acrylonitrile, polyvinyl acetate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, polyvinyl pyrrolidone, ethyl cellulose, and acetyl cellulose. Polymethyl methacrylate is preferable. The amount of the binder resin is 0% to 90%, preferably 40% to 80%, by weight with respect to the total solid content.
(Hologram recording medium)
In order to make a hologram recording medium using the composition for hologram recording of the present invention, it may be coated on a support without using a solvent, or a solvent or an additive may be added to the composition and mixed. And recording layer to form a recording layer.
溶剤としては、使用成分に対して十分な溶解度を持ち、良好な塗膜性を与えるものであれば特に制限はないが、例えば、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、メチルアミルケトン等のケトン系溶剤、トルエン、キシレン等の芳香族系溶媒、メタノール、エタノール、プロパノール、n−ブタノール、ヘプタノール、ヘキサノール、ジアセトンアルコール、フルフリルアルコール等のアルコール系溶剤、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、メチルセロソルブ、エチルセロソルブ、ブチルセロソルブ、メチルセロソルブアセテート、エチルセロソルブアセテート等のセロソルブ系溶剤、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート、ジプロピレングリコールジメチルエーテル等のプロピレングリコール系溶剤、酢酸エチル、酢酸ブチル、酢酸アミル、酢酸ブチル、エチレングリコールジアセテート、ジエチルオキサレート、ピルビン酸エチル、エチル−2−ヒド
ロキシブチレートエチルアセトアセテート、乳酸メチル、乳酸エチル、3−メトキシプロピオン酸メチル等のエステル系溶剤、ジメチルホルムアミド、ジメチルアセトアミドN−メチルピロリドン等の高極性溶剤、あるいはこれらの混合溶剤が挙げられる。溶剤使用の割合は、本実施形態のホログラム組成物の総量に対して、通常、重量比で1〜20倍程度の範囲である。
The solvent is not particularly limited as long as it has sufficient solubility for the components used and gives good coating properties. For example, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl amyl ketone, etc. Solvents, aromatic solvents such as toluene and xylene, alcohol solvents such as methanol, ethanol, propanol, n-butanol, heptanol, hexanol, diacetone alcohol and furfuryl alcohol, ether solvents such as tetrahydrofuran and dioxane, dichloromethane , Halogen solvents such as dichloroethane and chloroform, cellosolve solvents such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol mono Propylene glycol solvents such as chill ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, ethyl acetate, butyl acetate, acetic acid Amyl, butyl acetate, ethylene glycol diacetate, diethyl oxalate, ethyl pyruvate, ethyl-2-hydroxybutyrate ethyl acetoacetate, ester solvents such as methyl lactate, ethyl lactate, methyl 3-methoxypropionate, dimethylformamide, High polar solvents such as dimethylacetamide N-methylpyrrolidone, or a mixed solution thereof And the like. The proportion of the solvent used is usually in the range of about 1 to 20 times by weight with respect to the total amount of the hologram composition of the present embodiment.
支持体としては透明であっても、反射特性を有していてもよい。透明支持体としては、透明なガラス板、アクリル板、ポリカーボネート板、ポリエチレンテレフタレートフィルム、ポリエチレンフィルムなどが用いられる。好ましくは、ガラス板、アクリル板、ポリカーボネート板である。反射特性を有した支持体としては、アルミ板等の金属、または前記透明支持体上に金、銀、アルミ、等の金属を素材とする反射コート、またはフッ化マグネシウムや酸化ジルコニウム等の誘電体を単層あるいは多層にコーティングし、誘電体反射コートを施したものが用いられる。これらの支持体には、データアドレス用のパターニングを設けてあっても良い。パターニングは、基板自体に凹凸を形成したり、反射コーティングにパタンを形成したり、またはこれらを組み合わせた方法が可能である。 The support may be transparent or have reflective properties. As the transparent support, a transparent glass plate, an acrylic plate, a polycarbonate plate, a polyethylene terephthalate film, a polyethylene film, or the like is used. A glass plate, an acrylic plate, and a polycarbonate plate are preferable. As a support having reflection characteristics, a metal such as an aluminum plate, a reflective coat made of a metal such as gold, silver, or aluminum on the transparent support, or a dielectric such as magnesium fluoride or zirconium oxide Are coated in a single layer or multiple layers, and a dielectric reflection coat is applied. These supports may be provided with data address patterning. Patterning can be performed by forming irregularities on the substrate itself, forming a pattern on the reflective coating, or a combination thereof.
支持体の厚さは、0.5mmから1mmが好ましい。0.5mm以下では機械的強度が足りず、1mm以上では機械的強度は問題ないが、コストが高くなる。
塗布方法としては、従来公知の方法、例えば、回転塗布、ワイヤーバー塗布、ディップ塗布、エアーナイフ塗布、ロール塗布、及びブレード塗布等を用いることができる。また、特に膜厚の厚い記録層を形成する場合、型に入れて成型する方法も用いることができる。
The thickness of the support is preferably from 0.5 mm to 1 mm. If it is 0.5 mm or less, the mechanical strength is insufficient, and if it is 1 mm or more, there is no problem in mechanical strength, but the cost increases.
As a coating method, conventionally known methods such as spin coating, wire bar coating, dip coating, air knife coating, roll coating, and blade coating can be used. In addition, when a recording layer having a particularly large thickness is formed, a method of forming in a mold can be used.
記録層の膜厚は、10μmから5mm、好ましくは50μmから1mmである。10μm以下では、多重記録の際、各ホログラムの選択性が低くなり多重記録の度合いが低くなる。また、5mm以上では、記録層全体を均一に成形することが困難であり、各ホログラムの回折効率が均一で、かつSN比の高い多重記録が難しい。
本発明のホログラム記録媒体は、記録層上にさらに支持体、あるいは酸素遮断のための保護層を設けることもできる。
The thickness of the recording layer is 10 μm to 5 mm, preferably 50 μm to 1 mm. When the thickness is 10 μm or less, the selectivity of each hologram is lowered during multiplex recording, and the degree of multiplex recording is reduced. When the thickness is 5 mm or more, it is difficult to uniformly form the entire recording layer, and it is difficult to perform multiplex recording with uniform diffraction efficiency of each hologram and high SN ratio.
In the hologram recording medium of the present invention, a support or a protective layer for blocking oxygen can be further provided on the recording layer.
保護層としては、酸素による感度低下や保存安定性の劣化等の悪影響を防止するための公知技術、例えば、水溶性ポリマー等の塗布を用いることもできる。
記録層の上下に支持体を設ける場合は、2つある上下の支持体のうち、少なくともどちらか一方は透明である必要がある。
記録層の両側に透明支持体を有する媒体の場合、透過型、または反射型のホログラムが記録可能である。また、片側に反射特性を有する支持体を用いる場合は、反射型のホログラムが記録可能である。
As the protective layer, a known technique for preventing adverse effects such as a decrease in sensitivity due to oxygen and deterioration in storage stability, for example, application of a water-soluble polymer or the like can be used.
When the support is provided above and below the recording layer, at least one of the two upper and lower supports needs to be transparent.
In the case of a medium having a transparent support on both sides of the recording layer, a transmissive or reflective hologram can be recorded. When a support having reflection characteristics on one side is used, a reflection type hologram can be recorded.
反射型ホログラム媒体の場合、反射層は支持体と記録層の間にあってもよいし、支持体の外側面にあってもよいが、支持体と記録層の間にある方が好ましい。
透過型、反射型ホログラム媒体とも、記録光及び読み出し光が入射、及び出射する側、あるいは記録層と支持体との間に反射防止膜を設けても良い。これらの反射防止膜は、光の利用効率を向上させ、かつゴースト像の発生を抑制する働きをする。
In the case of a reflection type hologram medium, the reflection layer may be between the support and the recording layer, or may be on the outer surface of the support, but is preferably between the support and the recording layer.
In both transmission type and reflection type hologram media, an antireflection film may be provided on the side on which recording light and readout light enter and exit, or between the recording layer and the support. These antireflection films function to improve light utilization efficiency and suppress the generation of ghost images.
ホログラム記録媒体は、三次元画像表示装置や回折光学素子、及び大容量メモリ、その他に使用できる。 The hologram recording medium can be used for a three-dimensional image display device, a diffractive optical element, a large-capacity memory, and the like.
以下、本発明を実施例によりさらに具体的に説明するが、本発明はその趣旨を越えない限り、以下の実施例に限定されるものではない。
(実施例)
(重合性硫黄原子含有化合物の合成)
2−(2−ベンゾチアゾリルチオ)エタノール1.0gに塩化メチレン20mLとアクリル酸0.68g、トリエチルアミン2.6mL、縮合剤2−クロロ−1−メチルピリジニウムヨージド3.0gを加え、室温で24時間撹拌した後、得られた生成物をシリカゲルカラムクロマトグラフィーにて精製し、アクリル酸(2−(2−ベンゾチアゾリルチオ)エチル)(下記化合物)を収率96%で得た。
EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples unless it exceeds the gist.
(Example)
(Synthesis of polymerizable sulfur atom-containing compounds)
To 1.0 g of 2- (2-benzothiazolylthio) ethanol was added 20 mL of methylene chloride, 0.68 g of acrylic acid, 2.6 mL of triethylamine, and 3.0 g of the condensing agent 2-chloro-1-methylpyridinium iodide, and at room temperature. After stirring for 24 hours, the obtained product was purified by silica gel column chromatography to obtain acrylic acid (2- (2-benzothiazolylthio) ethyl) (the following compound) in a yield of 96%.
(ホログラム記録用組成物の作製)
バインダポリマーとしてPMMA(BR−80、三菱レイヨン製)100重量部(“重量部”を以下“部”と記す)を、テトラヒドロフラン溶媒250部中に溶解し、その後、反応性モノマーとしてアクリル酸(2−(2−ベンゾチアゾリルチオ)エチル)100重量部、光重合開始剤としてIrgacure 784 (チバ・スペシャルティ・ケミカルズ社製)2部を添加し、室温で4時間撹拌した。
(Preparation of composition for hologram recording)
100 parts by weight of PMMA (BR-80, manufactured by Mitsubishi Rayon) as a binder polymer (“parts by weight” is hereinafter referred to as “parts”) is dissolved in 250 parts of tetrahydrofuran solvent, and then acrylic acid (2 -(2-Benzothiazolylthio) ethyl) 100 parts by weight and 2 parts of Irgacure 784 (manufactured by Ciba Specialty Chemicals) as a photopolymerization initiator were added and stirred at room temperature for 4 hours.
スライドガラスに約1cm3滴下し、ギャップ1.2mmでブレードコートした。暗所
にて1晩乾燥した後、スライドガラスの両側にスペーサとして厚さ200μmのポリテトラフルオロエチレンフィルムを置き、別のスライドガラスでカバー、クリップで固定した物を80℃のオーブンで30分加熱し、厚さ200μmの平滑な記録媒体を得た。
形成した記録媒体を波長514.5nmのArレーザを用いて、ビーム1本当たり露光パワー密度5mW/cm2で二光束干渉露光を行った。露光する2本のビーム間角度は記
録媒体入射前で30度に設定した。二光束干渉露光と同時に波長632.8nmのHeNeレーザで回折効率をモニターした。
About 1 cm 3 was dropped on the slide glass and blade-coated with a gap of 1.2 mm. After drying overnight in the dark, place a polytetrafluoroethylene film with a thickness of 200 μm as spacers on both sides of the glass slide, cover with another glass slide, and fix with a clip. Thus, a smooth recording medium having a thickness of 200 μm was obtained.
The formed recording medium was subjected to two- beam interference exposure at an exposure power density of 5 mW / cm 2 per beam using an Ar laser having a wavelength of 514.5 nm. The angle between the two beams to be exposed was set to 30 degrees before entering the recording medium. Simultaneously with the two-beam interference exposure, the diffraction efficiency was monitored with a HeNe laser having a wavelength of 632.8 nm.
ホログラム記録媒体の特性を表す指標として、回折効率と記録感度がある。
ここでは、回折光強度を透過光強度と回折光強度の和で割った値で、回折効率を定義した。また、露光を開始してから回折効率が最高値に到達するまでの時間で、記録感度を定義した。
露光開始後20.8秒(記録感度20.8秒)で最大回折効率97.4%のホログラムが得られた。
(二光束干渉露光の概念図を図1に示す。)
(比較例)
アクリル酸(2−(2−ベンゾチアゾリルチオ)エチル)の代わりにビニルカルバゾールを用いた以外は、実施例1と同様に記録媒体を作製し、ホログラム特性を評価した。その結果、露光開始後300秒(記録感度300秒)で最大回折効率40%のホログラムを得た。
As indexes representing the characteristics of the hologram recording medium, there are diffraction efficiency and recording sensitivity.
Here, the diffraction efficiency is defined by the value obtained by dividing the diffracted light intensity by the sum of the transmitted light intensity and the diffracted light intensity. The recording sensitivity was defined as the time from the start of exposure until the diffraction efficiency reached the maximum value.
A hologram with a maximum diffraction efficiency of 97.4% was obtained 20.8 seconds after the start of exposure (recording sensitivity 20.8 seconds).
(A conceptual diagram of two-beam interference exposure is shown in FIG. 1.)
(Comparative example)
A recording medium was prepared in the same manner as in Example 1 except that vinylcarbazole was used instead of acrylic acid (2- (2-benzothiazolylthio) ethyl), and hologram characteristics were evaluated. As a result, a hologram having a maximum diffraction efficiency of 40% was obtained 300 seconds after the start of exposure (recording sensitivity 300 seconds).
Claims (3)
(式中、XはNまたはCHであり、環Aは置換基を有していても良い芳香環であり、R2
はアルケニル基、(メタ)アクリロイル基、オキシラニル基、チイラニル基、及びエチレンイミノ基からなる群から選ばれる重合性基を含有する基である。但しX=CHの時、環Aはチオフェン環類ではない。) A volume hologram recording composition for recording interference fringes due to interference of coherent light by a difference in refractive index, comprising a polymerizable sulfur atom-containing compound represented by the following general formula (1): A hologram recording composition.
(Wherein X is N or CH, ring A is an aromatic ring which may have a substituent, and R 2
Is a group containing a polymerizable group selected from the group consisting of an alkenyl group, a (meth) acryloyl group, an oxiranyl group, a thiranyl group, and an ethyleneimino group . However, when X = CH, ring A is not a thiophene ring. )
(式中、R3はアルケニル基、(メタ)アクリロイル基、オキシラニル基、チイラニル基
、又はエチレンイミノ基を含む基であり、R4〜R7はそれぞれ独立して、水素原子、ハロ
ゲン原子、アルキル基、アルコキシ基又はアリール基である。) 2. The hologram recording composition according to claim 1, wherein the polymerizable sulfur atom-containing compound is a compound represented by the following general formula (2).
(Wherein, R 3 is a group containing an alkenyl group, (meth) acryloyl group, oxy Rani group, lichen Rani group or ethyleneimino group,, R 4 to R 7 each independently represent a hydrogen atom, A halogen atom, an alkyl group, an alkoxy group or an aryl group.)
A holographic recording medium, wherein the recording layer comprises the composition according to claim 1.
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