JP4196925B2 - Uv分解性分子 - Google Patents
Uv分解性分子 Download PDFInfo
- Publication number
- JP4196925B2 JP4196925B2 JP2004295100A JP2004295100A JP4196925B2 JP 4196925 B2 JP4196925 B2 JP 4196925B2 JP 2004295100 A JP2004295100 A JP 2004295100A JP 2004295100 A JP2004295100 A JP 2004295100A JP 4196925 B2 JP4196925 B2 JP 4196925B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- substrate
- sam
- molecule
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 87
- 239000000758 substrate Substances 0.000 description 93
- 238000000034 method Methods 0.000 description 61
- 239000013545 self-assembled monolayer Substances 0.000 description 58
- 239000010408 film Substances 0.000 description 54
- 239000007790 solid phase Substances 0.000 description 40
- 125000000524 functional group Chemical group 0.000 description 29
- 230000002209 hydrophobic effect Effects 0.000 description 27
- 125000003277 amino group Chemical group 0.000 description 26
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- 230000000704 physical effect Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000008878 coupling Effects 0.000 description 18
- 238000010168 coupling process Methods 0.000 description 18
- 238000005859 coupling reaction Methods 0.000 description 18
- -1 o-nitrobenzyl ester Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 125000001153 fluoro group Chemical group F* 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000009257 reactivity Effects 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 11
- 238000007599 discharging Methods 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 9
- 229910052737 gold Inorganic materials 0.000 description 9
- 239000010931 gold Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000000059 patterning Methods 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000002356 single layer Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 6
- 125000002228 disulfide group Chemical group 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 230000003100 immobilizing effect Effects 0.000 description 5
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 125000001174 sulfone group Chemical group 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229960002685 biotin Drugs 0.000 description 4
- 239000011616 biotin Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000005660 hydrophilic surface Effects 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- UELXWWBFCRAICE-UHFFFAOYSA-N 11-aminododecane-1-thiol Chemical compound CC(N)CCCCCCCCCCS UELXWWBFCRAICE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000020958 biotin Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- XSWSEQPWKOWORN-UHFFFAOYSA-N dodecan-2-ol Chemical compound CCCCCCCCCCC(C)O XSWSEQPWKOWORN-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005837 enolization reaction Methods 0.000 description 2
- 150000002221 fluorine Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006303 photolysis reaction Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 2
- 239000002094 self assembled monolayer Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WMSUFWLPZLCIHP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 9h-fluoren-9-ylmethyl carbonate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)ON1C(=O)CCC1=O WMSUFWLPZLCIHP-UHFFFAOYSA-N 0.000 description 1
- WNGLYHIIKQKYTM-UHFFFAOYSA-N 1-aminodecane-1-thiol Chemical compound CCCCCCCCCC(N)S WNGLYHIIKQKYTM-UHFFFAOYSA-N 0.000 description 1
- 108090001008 Avidin Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 108020004682 Single-Stranded DNA Proteins 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- MJSHDCCLFGOEIK-UHFFFAOYSA-N benzyl (2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)OCC1=CC=CC=C1 MJSHDCCLFGOEIK-UHFFFAOYSA-N 0.000 description 1
- 230000008275 binding mechanism Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JARODAOQOSWMRF-UHFFFAOYSA-N disulfanediol Chemical compound OSSO JARODAOQOSWMRF-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 238000004654 kelvin probe force microscopy Methods 0.000 description 1
- 238000002032 lab-on-a-chip Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002103 nanocoating Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- NRZYYKACXDZFRF-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O.CC(C)(C)OC(N)=O NRZYYKACXDZFRF-UHFFFAOYSA-N 0.000 description 1
- MTBKGWHHOBJMHJ-UHFFFAOYSA-N tert-butyl imidazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CN=C1 MTBKGWHHOBJMHJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Images
Landscapes
- Materials For Photolithography (AREA)
- Pyrrole Compounds (AREA)
Description
一方、固相基板表面に、微細な膜パターンを形成する方法として、インクジェット法等の微小液滴吐出手段が用いられている。微小液滴吐出手段によれば、固相基板を載置したステージを移動させながら液滴を吐出することによって、液滴に含まれる物質を基板上の所定の位置に供給することができる。
「Surface and Coating Technology (2003年)」の169〜170頁 応用物理(2001年)第70巻1182頁 「J. Chem. Soc., Perkin Trans. 2, (2001年)」の1414頁 Pease, A. et al.; Proc. Natl. Acad. Sci. USA vol. 91, 5022-5026 (1994)
合物を含む溶液を吐出する前に、前記Xに結合可能な官能基を有する化合物を、前記固相表面に固定化する工程を含む、上記[1]から[6]のいずれか1項に記載の方法;[8]前記液滴を吐出する方法が、インクジェット法である、上記[1]から[7]のいずれか1項に記載の方法;[9]前記液滴は、水、エタノール、DMF、DMSO、HMPA、ピロリドン系溶媒、およびジオキサンからなる群から選択される1種以上を溶媒として含む、上記[1]から[8]のいずれか1項に記載の方法;[10]前記液滴を吐出する工程が、前記液滴の乾燥抑制手段を備える、上記[1]から[9]のいずれか1項に記載の方法、に関する。
また、上記分解可能な構造を分解することによって、一度固相表面に付与した物性や反応性をもとに戻したり、分解することにより表面に露出した官能基によって新たな物性や反応性を固相表面に付与したりすることも可能となる。
反応段階(1)で合成された物質(白色固体)は、その1H NMR、13C NMR、MS等のスペクトルデータが次に示す通りであり、この物質が4−(1H,1H,2H,2H−パーフルオロオクチロキシ)−3−メトキシベンズアルデヒド(収率30%)であることを同定した。
〔比較例〕
まず、図5に示すように、基板表面に、化合物(II)のN−ヒドロキシコハク酸イミドと結合可能な化合物として、11−アミノドデカンチオールを固定化した。基板はシリコン基板を用い、予め蒸着により金薄膜を形成しておいた。なお金薄膜はスパッタリングによっても形成することができる。
11−アミノドデカンチオールをエタノールに溶解させ1mMとし、この溶液に基板を浸漬させて12時間室温で放置した。エタノールで基板をリンスした後、窒素気流下で乾燥させた。
これにより、基板表面はアミノ基で覆われ、親水的な表面となった。
次に化合物(II)150mgを無水DMSO(ジメチルスルフォキシド)100mLに溶解させ、約2mMの溶液とし、さらにトリメチルアミン2mLを添加した。
そして図6に示すように、溶液脱気処理後、この溶液をインクジェット式吐出装置のインクレザーバーに入れ、上記アミノ基板表面の所定の位置に吐出した。吐出後、10分放置して、基板表面をDMSOで洗浄後、窒素気流下で乾燥させた。
この結果、液滴を吐出した領域にのみ化合物(II)が固定化され、CFで表されるフッ素鎖によって、疎水性ないし疎油性が付与される。一方、液滴が吐出されていない領域は、アミノ基が露出したままとなり親水性を示す。
次に、図11に示すように、化合物(II)の溶液を吐出しなかった領域に、例えば、9−フルオレニルメチル−N−スクシイミジル カーボネートのDMSO溶液をインクジェット及び類似した技術によって吐出、またはその溶液中に化合物(II)がパターン化された基板を浸漬させて、アミノ保護基を反応、固定化する。このアミノ保護分子としては、他にベンジル N−スクシンイミジルカーボネート、ジ−tert-ブチルジカーバーメート、N−Bocイミダゾール等でもよい。
続いて、図12に示すように、基板表面に308nmのUVを照射した。これにより、化合物(II)は図4に示す反応によって分解され、CFで表されるフッ素鎖が基板表面から除去され、再びアミノ基が露出し、この領域が親水性を示すようになる。その後、この活性アミノ基に例えば、ビオチン基を有するNHSエステル(NHS−LC−LC−Biotin;ピアーズ社製試薬)を溶かした溶液と反応させるとビオチンで被覆されたマイクロパターンが作成できる。さらにそのパターン上に例えば、ストレプトアビジンとコンジュゲートしたHRP(horseladish peroxidase)酵素分子を固定化することにより、酵素単分子膜のマイクロパターンが容易に形成できる。
Claims (4)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004295100A JP4196925B2 (ja) | 2004-10-07 | 2004-10-07 | Uv分解性分子 |
US11/116,265 US7479362B2 (en) | 2004-04-29 | 2005-04-28 | UV decomposable molecules and a photopatternable monomolecular film formed therefrom |
EP05009500A EP1610176A3 (en) | 2004-04-29 | 2005-04-29 | UV decomposable molecules and a photopatternable monomolecular film formed therefrom |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004295100A JP4196925B2 (ja) | 2004-10-07 | 2004-10-07 | Uv分解性分子 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008213931A Division JP2009029815A (ja) | 2008-08-22 | 2008-08-22 | Uv分解性分子およびこの分子から形成される光パターニング可能な単分子膜、並びに膜パターン形成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006104155A JP2006104155A (ja) | 2006-04-20 |
JP4196925B2 true JP4196925B2 (ja) | 2008-12-17 |
Family
ID=36374283
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004295100A Expired - Fee Related JP4196925B2 (ja) | 2004-04-29 | 2004-10-07 | Uv分解性分子 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4196925B2 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008277469A (ja) * | 2007-04-27 | 2008-11-13 | Hitachi Ltd | 感光性sam膜の露光方法および半導体装置の製造方法 |
JP6320392B2 (ja) * | 2013-08-27 | 2018-05-09 | 学校法人神奈川大学 | 含フッ素化合物、パターン形成用基板、光分解性カップリング剤、パターン形成方法、化合物 |
JP7344001B2 (ja) * | 2019-04-11 | 2023-09-13 | 株式会社Adeka | 重合体 |
-
2004
- 2004-10-07 JP JP2004295100A patent/JP4196925B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2006104155A (ja) | 2006-04-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7479362B2 (en) | UV decomposable molecules and a photopatternable monomolecular film formed therefrom | |
US7393515B2 (en) | Fluorinated compound, water repellent composition and thin film | |
US7732119B2 (en) | Photosensitive self-assembled monolayer for selective placement of hydrophilic structures | |
JP4014142B2 (ja) | 光分解性シランカップリング剤 | |
Besson et al. | A novel and simplified procedure for patterning hydrophobic and hydrophilic SAMs for microfluidic devices by using UV photolithography | |
JP4020247B2 (ja) | 高分子グラフト基板製造方法 | |
Critchley et al. | A mild photoactivated hydrophilic/hydrophobic switch | |
JP4196925B2 (ja) | Uv分解性分子 | |
CN1715270A (zh) | 可uv分解的分子及由其形成的可光形成图案的单分子薄膜 | |
EP1778703B1 (fr) | Agents de couplage a groupement protecteur photolabile et leurs utilisations, notamment pour la fonctionnalisation de supports solides | |
JP2007033090A (ja) | 光学検出用基板およびその製造方法 | |
JP2009029815A (ja) | Uv分解性分子およびこの分子から形成される光パターニング可能な単分子膜、並びに膜パターン形成方法 | |
JP5301082B2 (ja) | 化合物、膜形成用組成物および積層体の製造方法 | |
JP5093641B2 (ja) | 光分解性カップリング剤 | |
Driscoll et al. | A multilayered approach to complex surface patterning | |
JP4376540B2 (ja) | 金属表面修飾剤および新規含硫黄化合物 | |
US11332588B2 (en) | Process for modification of a solid surface | |
JP5347359B2 (ja) | o−ニトロベンジル基含有シラザン化合物及び用途 | |
JP2007031351A (ja) | シラン誘導体および有機薄膜形成体 | |
JPH08511284A (ja) | ポリマーの化学的官能化 | |
Stegmaier et al. | Photoactive branched and linear surface architectures for functional and patterned immobilization of proteins and cells onto surfaces: a comparative study | |
Feng | Spatial Surface Functionalization Based on Photo-induced Thiol Reactions | |
Chirakul | Part~ I: A convergent synthesis of hexahomotriazacalix (3) arenes and molecular recognition studies. Part~ II: Synthesis and characterization of an amine-terminated thiol as a precursor to self-assembled monolayers | |
JP2007031319A (ja) | シラン誘導体および有機薄膜形成体 | |
JP2007081136A (ja) | 有機機能性薄膜の形成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080624 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080820 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080909 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080922 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111010 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121010 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121010 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131010 Year of fee payment: 5 |
|
LAPS | Cancellation because of no payment of annual fees |