JP2013105088A - 二光子吸収材料及びその利用 - Google Patents
二光子吸収材料及びその利用 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 93
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 230000003287 optical effect Effects 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 230000005284 excitation Effects 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000007246 mechanism Effects 0.000 claims description 5
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- 230000008859 change Effects 0.000 description 12
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- 150000001875 compounds Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- SDGNTWFWHWDWNC-UHFFFAOYSA-N 1,2,3,4,5,6-hexakis(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC(C(=C(C#CC=1C=CC=CC=1)C(C#CC=1C=CC=CC=1)=C1C#CC=2C=CC=CC=2)C#CC=2C=CC=CC=2)=C1C#CC1=CC=CC=C1 SDGNTWFWHWDWNC-UHFFFAOYSA-N 0.000 description 2
- ISSDXNUDCZVUJA-UHFFFAOYSA-N 1,2,3,4-tetrakis(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC(C(=C1C#CC=2C=CC=CC=2)C#CC=2C=CC=CC=2)=CC=C1C#CC1=CC=CC=C1 ISSDXNUDCZVUJA-UHFFFAOYSA-N 0.000 description 2
- XOJSMLDMLXWRMT-UHFFFAOYSA-N 1,2-bis(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1C#CC1=CC=CC=C1 XOJSMLDMLXWRMT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- -1 coumarin, dithienothiophene derivatives Chemical class 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 229910052594 sapphire Inorganic materials 0.000 description 2
- 239000010980 sapphire Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
Description
項1. 一般式(1)で示されるベンゼン誘導体からなる、二光子吸収材料;
[一般式(1)中、R1〜R6の内、2個以上は下記一般式(2)で表される置換基であり且つ残りは水素原子であって、R1とR4、R2とR5、R3とR6のそれぞれの組の少なくとも一組は下記一般式(2)で表される置換基である。]
[一般式(1)中、R7〜R11は同一又は異なって、水素原子、炭素数1〜4のアルキル基、又は、炭素数1〜4のアルコキシ基を示す。]
項2. 一般式(1)中、R1とR4、R2とR5、R3とR6のそれぞれの組の少なくとも二組が一般式(2)で表される置換基である、項1に記載の二光子吸収材料。
項3. 一般式(2)中、R7〜R11の内、2つ以上の基が水素原子である、項1又は2に記載の二光子吸収材料。
項4. 一般式(1)で示されるベンゼン誘導体が、下記一般式(3)〜(5)で示されるベンゼン誘導体の中の少なくとも1種である、項1〜3のいずれかに記載の二光子吸収材料。
項5. 項1〜4のいずれかに記載の二光子吸収材料を含む、光造型用光硬化樹脂の硬化材料。
項6. 項1〜4のいずれかに記載の二光子吸収材料を含む、光制限材料。
項7. 項1〜4のいずれかに記載の二光子吸収材料を含む、三次元光メモリ材料。
項8. 波長390〜420nmのパルスレーザー光を発生するレーザー発生装置、レーザー集光装置と、光硬化性モノマー収容装置と、光硬化性モノマー中の所定の集光位置をレーザービームで走査するための機構とを備えた二光子吸収光造型装置であって、項5に記載の硬化材料が光硬化性モノマー中に含まれていることを特徴とする光造型装置。
項9. 波長390〜420nmのパルスレーザー光を発生するレーザー発生装置と、レーザー集光装置と、項7に記載の三次元光メモリ材料と、該メモリ材料の所定の集光位置をレーザービームで走査するための機構と、光学的読出し装置と、該光メモリ材料中の屈折率変化、局所的破壊又は局所的な蛍光強度の減少を検出する装置とを備えた三次元メモリ装置。
項10. 項1〜4のいずれかに記載の二光子吸収材料に、波長390〜420nmの光を照射することにより二光子吸収による励起を生じさせる、二光子吸収励起方法。
下記構造の一般式(3)に示されるベンゼン誘導体(ヘキサキス(フェニルエチニル)ベンゼン)、一般式(4)に示されるベンゼン誘導体(テトラキス(フェニルエチニル)ベンゼン)、及び一般式(5)に示されるベンゼン誘導体(ビス(フェニルエチニル)ベンゼン)を用いて、二光子吸収断面積の評価を行った。一般式(3)に示されるベンゼン誘導体及び一般式(4)に示されるベンゼン誘導体については、K. Konodo et al.,j. Chem. Soc., Chem. Commun. 1995, 55−56;W. Tao, et al., j. Org. Chem. 1990, 55, 63−66に記載の方法に準じて合成したものを使用した。また、一般式(5)に示されるベンゼン誘導体については、和光純薬工業社製(324-48211)を使用した。
Claims (10)
- 一般式(1)中、R1とR4、R2とR5、R3とR6のそれぞれの組の少なくとも二組が一般式(2)で表される置換基である、請求項1に記載の二光子吸収材料。
- 一般式(2)中、R7〜R11の内、2つ以上の基が水素原子である、請求項1又は2に記載の二光子吸収材料。
- 請求項1〜4のいずれかに記載の二光子吸収材料を含む、光造型用光硬化樹脂の硬化材料。
- 請求項1〜4のいずれかに記載の二光子吸収材料を含む、光制限材料。
- 請求項1〜4のいずれかに記載の二光子吸収材料を含む、三次元光メモリ材料。
- 波長390〜420nmのパルスレーザー光を発生するレーザー発生装置、レーザー集光装置と、光硬化性モノマー収容装置と、光硬化性モノマー中の所定の集光位置をレーザービームで走査するための機構とを備えた二光子吸収光造型装置であって、請求項5に記載の硬化材料が光硬化性モノマー中に含まれていることを特徴とする光造型装置。
- 波長390〜420nmのパルスレーザー光を発生するレーザー発生装置と、レーザー集光装置と、請求項7に記載の三次元光メモリ材料と、該メモリ材料の所定の集光位置をレーザービームで走査するための機構と、光学的読出し装置と、該光メモリ材料中の屈折率変化、局所的破壊又は局所的な蛍光強度の減少を検出する装置とを備えた三次元メモリ装置。
- 請求項1〜4のいずれかに記載の二光子吸収材料に、波長390〜420nmの光を照射することにより二光子吸収による励起を生じさせる、二光子吸収励起方法。
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WO2019155933A1 (ja) * | 2018-02-06 | 2019-08-15 | 国立大学法人大阪大学 | 光造形装置、及び造形物の製造方法 |
JP2020066194A (ja) * | 2018-10-26 | 2020-04-30 | カンタツ株式会社 | 3次元造形装置 |
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WO2022244611A1 (ja) * | 2021-05-18 | 2022-11-24 | パナソニックIpマネジメント株式会社 | 光吸収材料、記録媒体、情報の記録方法及び情報の読出方法 |
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JP2006022025A (ja) * | 2004-07-07 | 2006-01-26 | National Institute Of Advanced Industrial & Technology | 二光子吸収材料 |
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Non-Patent Citations (5)
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JPN6015011213; 鎌田賢司,外1名: '「2次元pi共役系分子の二光子吸収特性」' 電子情報通信学会技術研究報告. OME, 有機エレクトロニクス Vol.110, No.463, OME2010-79, 20110308, pp.11-16 * |
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JPN6015011216; K. Kondo, et al.: '"The Third-order Optical Non-linearity of the Phenylethynyl-substituted Benzene System"' Journal of the Chemical Society, Chemical Communications 1995, Issue 1, 19950107, pp.55-56 * |
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Cited By (5)
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WO2019155933A1 (ja) * | 2018-02-06 | 2019-08-15 | 国立大学法人大阪大学 | 光造形装置、及び造形物の製造方法 |
JPWO2019155933A1 (ja) * | 2018-02-06 | 2021-03-11 | 国立大学法人大阪大学 | 光造形装置、及び造形物の製造方法 |
JP2020066194A (ja) * | 2018-10-26 | 2020-04-30 | カンタツ株式会社 | 3次元造形装置 |
CN111098497A (zh) * | 2018-10-26 | 2020-05-05 | 康达智株式会社 | 三维造型装置 |
JP7331297B2 (ja) | 2018-10-26 | 2023-08-23 | 株式会社Tkr | 3次元造形装置 |
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