JP6531762B2 - 回折光学素子 - Google Patents
回折光学素子 Download PDFInfo
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- JP6531762B2 JP6531762B2 JP2016544966A JP2016544966A JP6531762B2 JP 6531762 B2 JP6531762 B2 JP 6531762B2 JP 2016544966 A JP2016544966 A JP 2016544966A JP 2016544966 A JP2016544966 A JP 2016544966A JP 6531762 B2 JP6531762 B2 JP 6531762B2
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- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 241000238118 Xanthidae Species 0.000 description 1
- RUFXNPIFCQCRTR-UHFFFAOYSA-N [2,5-dimethyl-5-(sulfanylmethyl)-1,4-dithian-2-yl]methanethiol Chemical compound SCC1(C)CSC(C)(CS)CS1 RUFXNPIFCQCRTR-UHFFFAOYSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- HRPVDGZEKVNVQW-UHFFFAOYSA-N [4-(sulfanylmethyl)cyclohexyl]methanethiol Chemical compound SCC1CCC(CS)CC1 HRPVDGZEKVNVQW-UHFFFAOYSA-N 0.000 description 1
- COYTVZAYDAIHDK-UHFFFAOYSA-N [5-(sulfanylmethyl)-1,4-dithian-2-yl]methanethiol Chemical compound SCC1CSC(CS)CS1 COYTVZAYDAIHDK-UHFFFAOYSA-N 0.000 description 1
- QWYSJTTWCUXHQO-UHFFFAOYSA-N [F].OC(=O)C=C Chemical compound [F].OC(=O)C=C QWYSJTTWCUXHQO-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- OGGRILHSCYKYST-UHFFFAOYSA-N adamantane-1,3-dithiol Chemical compound C1C(C2)CC3CC1(S)CC2(S)C3 OGGRILHSCYKYST-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
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- ZAKWKQQWRCCBAF-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,5-dithiol Chemical compound C1C2C(S)CC1C(S)C2 ZAKWKQQWRCCBAF-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
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- 230000001629 suppression Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/18—Esters containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
- C08F122/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
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- C—CHEMISTRY; METALLURGY
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- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
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Description
しかし、格子面が空気に触れている単層回折光学素子の場合、基準波長において一次回折効率を100%に出来るものの、波長が基準波長から離れるにつれ他次数の回折光が増加し、これがフレア光となる為にその光学性能を劣化させるという問題があった。この問題を解決する為、特徴的な2種類の樹脂からなる二つの格子が密着した構造を有する、密着複層型回折光学素子が考案された(例えば文献1、2)。すなわち、
(n2-n1)×h=λ (1)
式(1)において、n1、n2はそれぞれ樹脂の屈折率(n2>n1)、hは回折光学素子の格子高さ、λは波長である。
使用波長範囲において式(1)が常に成り立てば、使用波長範囲全域において一次光の回折効率が100%となり、回折光によるフレアの発生を無くすことが出来る。
エチレンオキサイド変性ジ(メタ)アクリレートと、前記ビスフェノールAFエチレンオキサイド変性ジ(メタ)アクリレートに対して、0.05〜3重量%の重合開始剤とを含む樹脂前駆体組成物が硬化してなる第1の光学要素と、チオールと、ジ(メタ)アクリレートとを含む樹脂前駆体組成物が硬化してなる第2の光学要素と、前記第1の光学要素と前記第2の光学要素との界面に設けられた回折格子と、を有し、前記チオールが下記化学
式2で表される。
(化1) 化学式1:
R=HもしくはCH3、m+n=1〜10
(化2) 化学式2:
m+n=1〜6
エチレンオキサイド変性ジ(メタ)アクリレートに対して、0.07〜0.7重量%の重合開始剤とを含む樹脂前駆体組成物が硬化してなる第1の光学要素と、チオールと、ジ(メタ)アクリレートとを含む樹脂前駆体組成物が硬化してなる第2の光学要素と、前記第1の光学要素と前記第2の光学要素との界面に設けられた回折格子と、を有し、前記チオールが下記化学式2で表される。
(化1) 化学式1:
R=HもしくはCH3、m+n=1〜10
(化2) 化学式2:
m+n=1〜6
キサイド変性ジ(メタ)アクリレートはm=1,n=1であるのが好ましい。
(化4)化学式1:
R=HもしくはCH3
m+n=1〜10
また、実施例3として2,2−ビス(4−(2−(メタ)クリロイルオキシ)エトキシ)フェニル−1,1,1,3,3,3−ヘキサフルオロプロパン(BMHF)にイルガキュア184を0.5wt%添加して前駆体組成物を準備した。
実施例1 : BMHF、イルガキュア184 0.1wt%
実施例2 : BAHF、イルガキュア184 0.1wt%
実施例3 : BMHF、イルガキュア184 0.5wt%
比較例 : 2,2,3,3,4,4,5,5,−オクタフルオロヘキサン−1,6−ジアクリレート 53wt%、
9,9−ビス[4−(2−アクリロイルオキシエトキシ)フェニル]フルオレン 42wt%、
2−フェノキシエチレングリコールアクリレート 5wt%、
光重合開始剤イルガキュア184 0.5wt%
(表1)
表1からビスフェノールAF エチレンオキサイド変性ジ(メタ)アクリレート樹脂であるBMHF、BAHFは屈折率が低く、分散が高い特性を示すことがわかる。また、比較例である従来材料aも同様に屈折率が低く、分散が高い特性を示すことがわかる。
第1回折光学要素1を構成する高屈折率低分散の樹脂としては、高屈折率低分散特性を示す組成物の硬化反応物であればどのような樹脂であってもよいが、例えば、低分散性特性を有する分子構造を有する(メタ)アクリレートと、以下の化学式2で示される高屈折率特性を有するチオールとを含む組成物の付加反応物を樹脂前駆体組成物を硬化させた樹脂が好ましい。
(化5)化学式2:
m+n=1〜6
化学式2のチオールは、「トリシクロデカンジメタンチオール(tricyclodecanedimethanethiol)」で、通称TDDTである。
(化6)化学式3:
R= HまたはCH3、m+n=1〜10
化学式3のアクリレートは、正式名称が「トリシクロデカンジメタノールジ(メタ)アクリレート(tricyclodecanedimethanoldi(meth)acrylate)」で、通称TCDAである。
従って、本実施例では、化学式2で示されるチオールにおいてm=1,n=1を用い、化学式3で示される(メタ)アクリレートにおいて、m=1、n=1、R=Hを用いた。
本実施例では、図6に示す回折光学素子において、第1回折光学要素1として上述した高屈折率低分散の樹脂である上述のTCDAとTDDTとを2.5:1の組成比(モル比)で付加反応させた樹脂前駆体組成物の硬化物を用い、第2回折光学要素2として上述した2,2−ビス(4−(2−アクリロイルオキシ)エトキシ)フェニル−1,1,1,3,3,3−ヘキサフルオロプロパン(BAHF)(上記化学式1において R=H、m=1,n=1)および2,2−ビス(4-(2-(メタ)クリロイルオキシ)エトキシ)フェニル−1,1,1,3,3,3−ヘキサフルオロプロパン(BMHF)(上記化学式1において R=CH3、m=1,n=1)を用いた。
光源は365nmを含むものであればよくメタルハライドランプ,高圧水銀ランプ,やLEDなどが使用可能である。なかでも特に自家蛍光を抑えたい場合にはLEDが望ましいので、本実施では、LEDを用いた。仮硬化後、金型から外し回折光学要素2が完成する。
紫外光照射は、365nmの紫外光を発生するLEDを備えた紫外光照射機(ユービックス株式会社製)を使用して行った。このとき、すりガラス越しに、仮硬化として25mW/cm2で60秒の照射を行い、次いで本硬化として40mW/cm2で250秒の照射を行った。
2,2−ビス(4−(2−(メタ)クリロイルオキシ)エトキシ)フェニル−1,1,1,3,3,3−ヘキサフルオロプロパン(BMHF)についても(BAHF)と実施例4と同様に回折光学要素2を成形した。本実施例では、高屈折率低分散光学要素として上記化学式2で表されるチオール(m=n=1)と上記化学式3で表されるメタクリレート(R=CH3、m=1、n=1)との組成物(モル比 TCDA:TDDT=3:1)のマイケル付加反応物である樹脂前駆体を用い、実施例4と同様に回折光学要素1を成形した。
実施例4 :
(低屈折率高分散光学要素) BAHF、イルガキュア184 0.1wt%
(高屈折率低分散光学要素) TCDA:TDDT=2.5:1の付加反応物、イルガキュア184 0.1wt%
実施例5 :
(低屈折率高分散光学要素) BMHF、イルガキュア184 0.1wt%
(高屈折率低分散光学要素) TCDA:TDDT=3:1の付加反応物、イルガキュア184 0.1wt%
(表2)
このように、レリーフパターン5の格子高さはどちらの実施例においても非常に小さい値に抑えることができた。
縦軸は(0+2)/1次光であり、この値が小さいほど、回折性能が優れていることを示す。本願実施例で形成した回折光学素子は従来の樹脂で構成される回折光学素子を用いた場合に比べて不要次数の回折光強度が小さく、高い回折性能を示す。また、斜入射光に対する回折効率も高く、生物系の顕微鏡対物レンズ、交換レンズ、双眼鏡、望遠鏡、防犯カメラ、プロジェクタなどの広い用途に用いることができる。
1 第1回折光学要素 2 第2回折光学要素
5 レリーフパターン(回折格子パターン)
10 レンズ
Claims (4)
- 前記化学式1で表されるビスフェノールAF エチレンオキサイド変性ジ(メタ)アク
リレートはm=1,n=1である請求項1または2に記載の回折光学素子。
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