JP7057345B2 - 光活性触媒組成物 - Google Patents
光活性触媒組成物 Download PDFInfo
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- JP7057345B2 JP7057345B2 JP2019506429A JP2019506429A JP7057345B2 JP 7057345 B2 JP7057345 B2 JP 7057345B2 JP 2019506429 A JP2019506429 A JP 2019506429A JP 2019506429 A JP2019506429 A JP 2019506429A JP 7057345 B2 JP7057345 B2 JP 7057345B2
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- 239000000203 mixture Substances 0.000 title claims description 193
- 239000003054 catalyst Substances 0.000 title claims description 115
- -1 monounsaturated cyclic olefin Chemical class 0.000 claims description 150
- 238000000034 method Methods 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 75
- 239000002243 precursor Substances 0.000 claims description 75
- 229920000642 polymer Polymers 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 238000005649 metathesis reaction Methods 0.000 claims description 64
- 239000000463 material Substances 0.000 claims description 60
- 150000001336 alkenes Chemical class 0.000 claims description 53
- 229910052707 ruthenium Inorganic materials 0.000 claims description 49
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 47
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 43
- 239000003446 ligand Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 33
- 125000004122 cyclic group Chemical group 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 29
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000011159 matrix material Substances 0.000 claims description 20
- 238000000059 patterning Methods 0.000 claims description 20
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 125000002524 organometallic group Chemical group 0.000 claims description 18
- 150000001345 alkine derivatives Chemical class 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 238000001459 lithography Methods 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 11
- 229920001400 block copolymer Polymers 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000011065 in-situ storage Methods 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000002407 tissue scaffold Substances 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 238000001093 holography Methods 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 238000010146 3D printing Methods 0.000 claims description 4
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 238000003618 dip coating Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 239000010410 layer Substances 0.000 description 100
- 125000005842 heteroatom Chemical group 0.000 description 56
- 239000000243 solution Substances 0.000 description 42
- 125000000524 functional group Chemical group 0.000 description 38
- 125000001424 substituent group Chemical group 0.000 description 34
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 31
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 21
- 230000003197 catalytic effect Effects 0.000 description 21
- 125000003710 aryl alkyl group Chemical group 0.000 description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 15
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 229920002120 photoresistant polymer Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000005865 alkene metathesis reaction Methods 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 125000003367 polycyclic group Chemical group 0.000 description 13
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000002723 alicyclic group Chemical group 0.000 description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
- 125000000743 hydrocarbylene group Chemical group 0.000 description 11
- 125000002950 monocyclic group Chemical group 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 10
- 238000010791 quenching Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
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- 125000004404 heteroalkyl group Chemical group 0.000 description 9
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- 230000000171 quenching effect Effects 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
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- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 8
- 239000013522 chelant Substances 0.000 description 8
- 238000005686 cross metathesis reaction Methods 0.000 description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 description 8
- 150000002848 norbornenes Chemical group 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 125000000732 arylene group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
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- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 238000000206 photolithography Methods 0.000 description 7
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- 241000894007 species Species 0.000 description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
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- 229960000834 vinyl ether Drugs 0.000 description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
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- 238000011088 calibration curve Methods 0.000 description 6
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- IMEVSAIFJKKDAP-UHFFFAOYSA-N 4-methoxy-2-(4-methoxypyridin-2-yl)pyridine Chemical compound COC1=CC=NC(C=2N=CC=C(OC)C=2)=C1 IMEVSAIFJKKDAP-UHFFFAOYSA-N 0.000 description 4
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- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 description 3
- DMGCMUYMJFRQSK-UHFFFAOYSA-N 5-prop-1-en-2-ylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C(=C)C)CC1C=C2 DMGCMUYMJFRQSK-UHFFFAOYSA-N 0.000 description 3
- CJQNJRMLJAAXOS-UHFFFAOYSA-N 5-prop-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CC)CC1C=C2 CJQNJRMLJAAXOS-UHFFFAOYSA-N 0.000 description 3
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- 125000000707 boryl group Chemical group B* 0.000 description 3
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Images
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- G03F7/201—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by an oblique exposure; characterised by the use of plural sources; characterised by the rotation of the optical device; characterised by a relative movement of the optical device, the light source, the sensitive system or the mask
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Catalysts (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Description
本発明は、米国国立科学財団により与えられた助成第16447467号および米国エネルギー省により与えられた助成第DE-AC05-060R23100号の下で政府支援を受けてなされた。政府は、本発明に一定の権利を有する。
式中、
X1およびX2は、独立してアニオン性リガンドであり、
Yは、O、N-R1、またはSであり、好ましくはOであり、
Qは、構造-CR11R12-CR13R14-または-CR11=CR13-、好ましくは-CR11R12-CR13R14-を有する2原子結合であり、R11、R12、R13、およびR14は、独立して、水素、置換されていてもよいヒドロカルビル、置換されていてもよいヘテロ原子含有ヒドロカルビル、または官能基であり、
R1およびR2は、独立して、水素、置換されていてもよいヒドロカルビル、置換されていてもよいヘテロ原子含有ヒドロカルビルであるか、または互いに結合して、置換されていてもよい環式脂肪族基を形成していてもよく、
R3およびR4は、独立して、置換されていてもよいヒドロカルビルであり、好ましくは、置換されていてもよいアダマンチルまたは置換されていてもよいフェニルであり、
R5およびR6は、独立して、Hまたは電子求引基もしくは電子供与基、例えば、C1~24アルキル、C1~24アルコキシ、C1~24フルオロアルキル(ペルフルオロアルキルを含む)、C1~24フルオロアルコキシ(ペルフルオロアルコキシを含む)、C1~24アルキルヒドロキシ、C1~24アルコキシヒドロキシ、C1~24フルオロアルキルヒドロキシ(ペルフルオロアルキルヒドロキシを含む)、C1~24フルオロアルコキシヒドロキシ(ペルフルオロアルコキシヒドロキシを含む)ハロ(例えば、F、Cl、Br)、シアノ、ニトロ、もしくはヒドロキシル、シリル、もしくはホスホニルであり、
mおよびnは、独立して、1、2、3、または4である。
式中、
Zは、-O-またはC(Ra)(Rb)であり、
RPは、独立して、Hであるか、または-N(Ra)(Rb)、-O-Ra、-C(O)O-Ra、-OC(O)-(C1~6アルキル)、もしくは-OC(O)-(C6~10アリール)で遠位末端が置換されていてもよいC1~6アルキルであるか、または保護されていてもよい3~10のアミノ酸の配列(好ましくはR-G-Dもしくはアルギニン-グリシン-アスパラギン酸を含む)であり、
Wは、独立して、-N(Ra)(Rb)、-O-Ra、または-C(O)O-Ra、-P(O)(ORa)2、-SO2(ORa)、またはSO3 -であり、
RaおよびRbは、独立してHまたはC1~6アルキルであり、
C6~10アリールは、1、2、3、4、または5個の保護されていてもよいヒドロキシル基(保護されたヒドロキシル基は好ましくはベンジル)で置換されていてもよく、
nは、独立して、1、2、3、4、5、または6である。
いくつかの実施形態では、不飽和有機前駆体は、単官能化または多官能化されていてもよい。
本開示は、実質的に不活性であるとこれまで考えられていた触媒を使用してオレフィンをメタセシスする方法に関する。これらの方法は、新規な感光性組成物、フォトレジストとしてのそれらの使用、および基体上のポリマー層のパターニングに関する方法を提供する。さらに、組成物および方法に対する改変は、センサー、薬剤送達システム、および組織スキャフォールドの作製などにおいて有用な組成物の先例のない機能化を提供する。新規の組成物および関連する方法はまた、例えばフォトニックデバイスを含む、臨界寸法のデバイスの新たな達成手段を提供する三次元物体を作製する機会も提供する。
X1およびX2は、独立してアニオン性リガンドであり、
Yは、O、N-R1、またはSであり、好ましくはOであり、
Qは、構造-CR11R12-CR13R14-または-CR11=CR13-、好ましくは-CR11R12-CR13R14-を有する2原子結合であり、R11、R12、R13、およびR14は独立して水素、置換されていてもよいヒドロカルビルであり、
R1およびR2は、独立して水素もしくは置換されていてもよいヒドロカルビルであるか、またはR1およびR2は、互いに結合して置換されていてもよい環式脂肪族基を形成してもよく、
R3およびR4は、独立して、置換されていてもよいヒドロカルビルであり、
R5およびR6は、独立して、Hまたは電子求引基もしくは電子供与基、例えば、C1~24アルキル、C1~24アルコキシ、C1~24フルオロアルキル、C1~24フルオロアルコキシ、C1~24アルキルヒドロキシ、C1~24アルコキシヒドロキシ、C1~24フルオロアルキルヒドロキシ(ペルフルオロアルキルヒドロキシを含む)、C1~24フルオロアルコキシヒドロキシ、ハロ、シアノ、ニトロ、もしくはヒドロキシであり、
mおよびnは、独立して1、2、3または4である。
L3およびL4は、独立して中性電子供与リガンドであり、
kおよびnは、独立して0または1であり、
RAおよびRBは、独立して水素もしくは置換されていてもよいヒドロカルビルであるか、または結合して置換されていてもよい芳香族もしくは脂肪族環式基を形成してもよく、
ここで、Q、X1、X2、R3、およびR4は、本明細書の他の箇所に記載の通りである。
好ましいL3およびL4リガンドは、芳香族窒素含有および酸素含有複素環であり、特に好ましいL3およびL4リガンドは、1~3、好ましくは1または2の置換基で置換されていてもよい単環式N-ヘテロアリールリガンドである。特に好ましいL3およびL4リガンドの具体例は、ピリジンおよび置換型ピリジン、例えば3-ブロモピリジン、4-ブロモピリジン、3,5-ジブロモピリジン、2,4,6-トリブロモピリジン、2,6-ジブロモピリジン、3-クロロピリジン、4-クロロピリジン、3,5-ジクロロピリジン、2,4,6-トリクロロピリジン、2,6-ジクロロピリジン、4-ヨードピリジン、3,5-ジヨードピリジン、3,5-ジブロモ-4-メチルピリジン、3,5-ジクロロ-4-メチルピリジン、3,5-ジメチル-4-ブロモピリジン、3,5-ジメチルピリジン、4-メチルピリジン、3,5-ジイソプロピルピリジン、2,4,6-トリメチルピリジン、2,4,6-トリイソプロピルピリジン、4-(tert-ブチル)ピリジン、4-フェニルピリジン、3,5-ジフェニルピリジン、3,5-ジクロロ-4-フェニルピリジンなどである。
構造(A)が包含する二環式(ビ環式)および多環式(ポリ環式)オレフィンは、通常構造(D)によって表され得、
さらに、RE5、RE6、RE7、およびRE8基のいずれかを他のRE5、RE6、RE7、およびRE8基のいずれかに結合させて、4~30個の環炭素原子を含む置換型もしくは非置換型脂環式基、もしくは6~18個の環炭素原子を含む置換型もしくは非置換アリール基、またはそれらの組み合わせを得ることができ、結合は、ヘテロ原子または官能基を含み得、例えば、結合は、限定はされないが、エーテル、エステル、チオエーテル、アミノ、アルキルアミノ、イミノ、または無水基を含み得る。環式基は、単環式、二環式、または多環式であることができる。環式基は、不飽和の場合、モノ不飽和またはマルチ不飽和を含むことができ、モノ不飽和環式基が好ましい。環は、置換型の場合、一置換型または多置換型を含み、ここで、置換基は、水素、ヒドロカルビル、置換型ヒドロカルビル、ヘテロ原子含有ヒドロカルビル、置換型ヘテロ原子含有ヒドロカルビル、-(Z*)n-Fnから独立して選択され、ここで、nはゼロまたは1であり、Z*およびFnは、上記で定義した通りであり、官能基(Fn)は、上記で与えられている。
スキーム1
スキーム2
スキーム3
ここで、
式中、
Zは、-O-、またはC(Ra)(Rb)であり、
RPは、独立してHであるか、または-N(Ra)(Rb)、-O-Ra、-C(O)O-Ra、-OC(O)-(C1~6アルキル)、もしくは-OC(O)-(C6~10アリール)で末端が置換されていてもよいC1~6アルキル、または(好ましくはR-G-Dもしくはアルギニン-グリシン-アスパラギン酸を含む)保護されていてもよい3~10のアミノ酸の配列であり、
Wは、独立して、-N(Ra)(Rb)、-O-Ra、または-C(O)O-Ra、-P(O)(ORa)2、-SO2(ORa)、またはSO3 -であり、
RaおよびRbは、独立して、HまたはC1~6アルキルであり、
C6~10アリールは、1、2、3、4、または5の保護されていてもよいヒドロキシル基(保護されたヒドロキシル基は好ましくはベンジルである)で置換されていてもよく、
nは、独立して、1、2、3、4、5、または6である。
(a) 本明細書に記載の組成物のうちいずれか一つの感光性組成物の層を前記基体上に堆積させることと、
(b) 前記感光性組成物の層の一部を本明細書の他の箇所に記載の適当な波長を有する光で照射して、それによって重合領域および非重合領域のパターン化層を得ることと、を含んでなる。特定の他の実施形態は、パターンの非重合領域を除去することをさらに含んでなる。
(a)メタセシス重合または架橋反応を経ることができる1以上のアルケンまたはアルキンを有する重合性材料組成物と適当な光触媒との2以上の層を堆積することであって、これらの層のうちの1以上が、このキャパシティで作用する本明細書に記載のルテニウムビピリジン錯体を含有し、前記堆積が積層体を形成することと、
(b)前記積層体の隣接層の少なくとも一部を重合または架橋するのに充分な条件下で、前記積層体の少なくとも一部に光を照射して、前記積層体の2以上の層に光を透過させ、照射することと、
を含んでなる方法によって作製する。
関連する実施形態では、積層体の反応しなかった部分を後で除去し得る。
X1およびX2は、独立して、アニオン性リガンドであり、
Yは、O、N-R1、またはS、好ましくはOであり、
Qは、構造-CR11R12-CR13R14-または-CR11=CR13-、好ましくは-CR11R12-CR13R14-を有する2原子結合であり、R11、R12、R13、およびR14は、独立して、水素、置換されていてもよいヒドロカルビルであり、
R1およびR2は、独立して、水素、置換されていてもよいヒドロカルビルであるか、または互いに結合して、置換されていてもよい環式脂肪族基を形成してもよく、
R3およびR4は、独立して、置換されていてもよいヒドロカルビルであり、
R5およびR6は、独立して、H、C1~24アルキル、C1~24アルコキシ、C1~24フルオロアルキル、C1~24フルオロアルコキシ、C1~24アルキルヒドロキシ、C1~24アルコキシヒドロキシ、C1~24フルオロアルキルヒドロキシ(ペルフルオロアルキルヒドロキシを含む)、C1~24フルオロアルコキシヒドロキシ、ハロ、シアノ、ニトロ、またはヒドロキシであり、
mおよびnは、独立して、1、2、3、または4である。
式(I)のルテニウムカルベンメタセシス触媒は、本明細書に記載されているように添加してもよく、または本明細書に記載されているようにインサイチュで生じさせてもよい。独立したX1およびX2は、アニオン性リガンドであり、互いに対してシスに位置すると考えられているが、化合物は示されている構造の幾何異性体としても存在し得る。
(a)構造(B)で表されるモノ不飽和環状オレフィンであって、
RA1およびRA2は、独立して、水素、ヒドロカルビル(例えば、C1~C20アルキル、C5~C20アリール、C5~C30アラルキル、もしくはC5~C30アルカリール)、置換型ヒドロカルビル(例えば、置換型C1~C20アルキル、C5~C20アリール、C5~C30アラルキル、もしくはC5~C30アルカリール)、ヘテロ原子含有ヒドロカルビル(例えば、C1~C20ヘテロアルキル、C5~C20ヘテロアリール、ヘテロ原子含有C5~C30アラルキル、もしくはヘテロ原子含有C5~C30アルカリール)、および置換型ヘテロ原子含有ヒドロカルビル(例えば、置換型C1~C20ヘテロアルキル、C5~C20ヘテロアリール、ヘテロ原子含有C5~C30アラルキル、もしくはヘテロ原子含有C5~C30アルカリール)であり、置換型ヒドロカルビルもしくは置換型ヘテロ原子含有ヒドロカルビルの場合、置換基は、官能基(「Fn」)、例えば、アルケン、アルキン、ホスホナト、ホスホリル、ホスファニル、ホスフィノ、スルホナト、C1~C20アルキルスルファニル、C5~C20アリールスルファニル、C1~C20アルキルスルホニル、C5~C20アリールスルホニル、C1~C20アルキルスルフィニル、C5~C20アリールスルフィニル、スルホンアミド、アミノ、アミド、イミノ、ニトロ、ニトロソ、ヒドロキシル、C1~C20アルコキシ、C5~C20アリールオキシ、C2~C20アルコキシカルボニル、C5~C20アリールオキシカルボニル、カルボキシル、カルボキシラト、メルカプト、ホルミル、C1~C20チオエステル、シアノ、シアナト、チオシアナト、イソシアネート、チオイソシアネート、カルバモイル、エポキシ、スチレニル、シリル、シリルオキシ、シラニル、シロキサザニル、ボロナト、ボリル、もしくはハロゲン、もしくは金属含有もしくはメタロイド含有基(ここで、金属は、例えば、SnもしくはGeであり得る)であり、
RB1、RB2、RB3、RB4、RB5、およびRB6は、水素、ヒドロカルビル、置換型ヒドロカルビル、ヘテロ原子含有ヒドロカルビル、置換型ヘテロ原子含有ヒドロカルビル、および-(Z*)n-Fnからなる群から独立して選択され、ここで、Z*は、ヒドロカルビレン結合基、例えば、アルキレン、置換型アルキレン、ヘテロアルキレン、置換型ヘテロアルケン、アリーレン、置換型アリーレン、ヘテロアリーレン、もしくは置換型ヘテロアリーレン結合であり、
RB1~RB6基のいずれかが置換型ヒドロカルビルもしくは置換型ヘテロ原子含有ヒドロカルビルである場合、置換基が1以上の-(Z*)n-Fn基を含み得る、前記モノ不飽和環状オレフィン、もしくは
(b)構造(C)で表される単環式ジエンであって、
RC1、RC2、RC3、RC4、RC5、およびRC6は、RB1~RB6に対応すると定義される、前記単環式ジエン、もしくは
(c)構造(D)で表される二環式もしくは多環式オレフィンであって、
RD1、RD2、RD3、およびRD4は、RB1~RB6に対応すると定義され、
eは、1~8(典型的には2~4)の範囲の整数であり、
fは、通常1もしくは2であり、
Tは、低級アルキレンもしくはアルケニレン(通常置換型もしくは非置換型メチルもしくはエチル)、CHRG1、C(RG1)2、O、S、N-RG1、P-RG1、O=P-RG1、Si(RG1)2、B-RG1、もしくはAs-RG1であり、ここで、RG1は、アルキル、アルケニル、シクロアルキル、シクロアルケニル、アリール、アルカリール、アラルキル、もしくはアルコキシであり、さらに、RD1、RD2、RD3、およびRD4基のいずれかを他のRD1、RD2、RD3、およびRD4基のいずれかに結合させて、4~30個の環炭素原子を含む置換型もしくは非置換型脂環式基、もしくは6~18個の環炭素原子を含む置換型もしくは非置換アリール基、もしくはそれらの組み合わせを得ることができ、前記結合は、ヘテロ原子もしくは官能基を含み得、例えば、前記結合は、限定はされないが、エーテル、エステル、チオエーテル、アミノ、アルキルアミノ、イミノ、もしくは無水基を含み得る、前記二環式もしくは多環式オレフィン、もしくは
(d)構造(E)で表されるノルボルネンであって、
RE1、RE2、RE3、RE4、RE5、RE6、RE7、およびRE8は、RB1~RB6に対応すると定義され、
「a」は、単結合もしくは二重結合を表し、
fは1もしくは2であり、
gは0~5の整数であり、「a」が二重結合である場合、RE5、RE6の一方とRE7、RE8の一方は、存在しない、前記ノルボルネン、もしくは
(e)それらの混合物。
Ra、Rb、Rc、Rd、Re、およびRfが、独立して、Hまたはアルキル(好ましくはC1~20アルキル、より好ましくはC1~10アルキル)である、実施形態1~11のいずれか一つに記載の感光性組成物。
式中、
Ra、Rb、Rc、Rd、Re、およびRfが、独立して、Hまたはアルキル(好ましくはC1~20アルキル、より好ましくはC1~10アルキル)である、実施形態1~11のいずれか一つに記載の感光性組成物。
Ru-カルベン触媒を用いる、係留有機金属を含んでなる感光性組成物
ペンダント官能基を含んでなる感光性組成物
式中、
Zが、-O-またはC(Ra)(Rb)であり、
RPが、独立して、Hであるか、または-N(Ra)(Rb)、-O-Ra、-C(O)O-Ra、-OC(O)-(C1~6アルキル)、もしくは-OC(O)-(C6~10アリール)で末端が置換されていてもよいC1~6アルキルであるか、または保護されていてもよい3~10のアミノ酸の配列(好ましくはR-G-Dもしくはアルギニン-グリシン-アスパラギン酸を含む)であり、
Wが、独立して、-N(Ra)(Rb)、-O-Ra、または-C(O)O-Ra、-P(O)(ORa)2、-SO2(ORa)、またはSO3 -であり、
RaおよびRbが、独立して、HまたはC1~6アルキルであり、
C6~10アリールが、1、2、3、4、または5の保護されていてもよいヒドロキシル基(保護されたヒドロキシル基は好ましくはベンジル)で置換されていてもよく、
nが、独立して、1、2、3、4、5、または6である、
実施形態1~20のいずれか一つに記載の感光性組成物。
Bnがベンジルであり、tBuがtert-ブチルであり、PbFが2,2,4,6,7-ペンタメチルジヒドロベンゾフランである、実施形態21に記載の組成物。
感光性組成物の製造方法
(a)実施形態1~22のいずれか一つに記載の感光性組成物の1以上の層を基体上に堆積させることと、
(b)前記感光性組成物の層の一部に、約300~約500nmの範囲、好ましくは約350~約450nmの範囲の波長を含んでなる光を照射して、前記層の照射部分を重合させ、それによって重合領域および非重合領域のパターン化層を得ることとを含んでなる前記方法。本実施形態の他の態様では、前記光は、約300~約320nm、約320~約340nm、約340~約360nm、約360~約380nm、約380~約400nm、約400~約420nm、約420~約440nm、約440~約460nm、約460~約480nm、約480~約500nm、またはそれらの組み合わせの範囲の1種以上の波長を含んでなる。
重合組成物
Ru-カルベン触媒を用いる、積層感光性組成物の三次元構造体を形成する方法
(a)メタセシス重合または架橋反応を経ることができる1以上のアルケンまたはアルキンを有する組成物と前記組成物に混合または溶解された光活性剤との2以上の層を堆積することであって、1以上の層が実施形態1~22のいずれか一つに記載の組成物を含んでなり、前記堆積が積層体を形成することと、
(b)前記積層体の隣接層の少なくとも一部を重合または架橋するのに充分な条件下で、前記積層体の少なくとも一部に光を照射して、前記積層体の2以上の層に光を透過させ、照射することと、
を含んでなる方法。
Claims (33)
- 1種以上の不飽和有機前駆体を含んでなる重合性材料マトリックス内に混合された、式(I)のルテニウムカルベンメタセシス触媒またはその幾何異性体を含んでなる感光性組成物であって、
式中、
X1およびX2が、独立してアニオン性リガンドであり、
Yが、O、N-R1、またはSであり、
Qが、構造-CR11R12-CR13R14-または-CR11=CR13-、好ましくは-CR11R12-CR13R14-を有する2原子結合であり、R11、R12、R13、およびR14が、独立して水素、ヒドロカルビル、または置換型ヒドロカルビルであり、
R1およびR2が、独立して水素、置換されていてもよいヒドロカルビルであるか、または互いに結合して、置換されていてもよい環式脂肪族基を形成してもよく、
R3およびR4が、独立して、置換されていてもよいヒドロカルビルであり、
R5およびR6が、独立して、H、C1~24アルキル、C1~24アルコキシ、C1~24フルオロアルキル、C1~24フルオロアルコキシ、C1~24アルキルヒドロキシ、C1~24アルコキシヒドロキシ、C1~24フルオロアルキルヒドロキシ(ペルフルオロアルキルヒドロキシを含む)、C1~24フルオロアルコキシヒドロキシ、ハロ、シアノ、ニトロ、またはヒドロキシであり、
mおよびnが、独立して、1、2、3、または4である、感光性組成物。 - R1がHであり、R2がC1~6アルキルであり、YがOである、請求項1に記載の感光性組成物。
- Qが-CH2-CH2-であり、R3もしくはR4のいずれか、またはR3およびR4の両方が、2、6位で、独立のC1~6アルキル基で置換されていてもよいフェニル基である、請求項1に記載の感光性組成物。
- Qが-CH2-CH2-であり、R3およびR4が独立してメシチルまたは置換されていてもよいアダマンチルである、請求項1に記載の感光性組成物。
- R5およびR6が、独立して、H、メチル、エチル、プロピル、ブチル、メトキシ、トリフルオロメチル、フルオロ、クロロ、ブロモ、シアノ、またはニトロである、請求項1に記載の感光性組成物。
- 前記不飽和有機前駆体が、モノ不飽和環式オレフィン、モノ環式ジエン、またはビ環式もしくはポリ環式オレフィンを含んでなる、請求項1に記載の感光性組成物。
- 前記不飽和有機前駆体がROMP前駆体である、請求項1に記載の感光性組成物。
- 基体にポリマー画像をパターニングする方法であって、
(a)請求項1に記載の感光性組成物の層を基体上に堆積させることと、
(b)前記感光性組成物の層の一部に250~800nmの範囲の1種以上の波長を含んでなる光を照射して、前記層の照射部分を重合させ、それによって前記層中に重合領域および非重合領域を得ることと、を含んでなる方法。 - (a)前記感光性組成物をスピンコーティング、ディップコーティング、もしくはスプレーコーティングによって堆積させるか、または前記感光性組成物が、ゲル状、半固体状、または固体状のフィルムであり、前記感光性組成物を前記基体上に積層することによって堆積させ、
(b)前記照射部分を、フォトマスクの使用により、直描光照射により、または干渉、ナノインプリント、もしくは回折勾配リソグラフィにより、またはステレオリソグラフィ、ホログラフィ、もしくはデジタル光プロジェクション(DLP)によりパターニングし、
(c)前記パターンの前記非重合領域を除去する、
請求項10に記載の方法。 - 前記重合性材料マトリックスが、前記1種以上の不飽和有機前駆体とメタセシスすることができるペンダント不飽和部分を有する1以上の有機金属部分をさらに含んでなり、前記ペンダント不飽和部分が、1以上のアルケンまたは1以上のアルキン結合を含んでなり、前記有機金属部分が3族から12族の遷移金属を含んでなる、請求項1に記載の感光性組成物。
- 前記3族から12族の遷移金属が、Fe、Co、Ni、Ti、Al、Cu、Zn、Ru、Rh、Ag、Ir、Pt、Au、またはHgである、請求項13に記載の感光性組成物。
- 前記1種以上の不飽和有機前駆体が、構造:
を有する化合物を含んでなり、
式中、
Zが、-O-またはC(Ra)(Rb)であり、
RPが、独立して、H;-N(Ra)(Rb)、-O-Ra、-C(O)O-Ra、-OC(O)-(C1~6アルキル)、もしくは-OC(O)-(C6~10アリール)で末端が置換されていてもよいC1~6アルキル;または保護されていてもよい3~10のアミノ酸の配列(好ましくはR-G-Dもしくはアルギニン-グリシン-アスパラギン酸を含む);であり、
Wが、独立して、-N(Ra)(Rb)、-O-Ra、または-C(O)O-Ra、-P(O)(ORa)2、-SO2(ORa)、またはSO3 -であり、
RaおよびRbが、独立してHまたはC1~6アルキルであり、
C6~10アリールが、1、2、3、4、または5の保護されていてもよいヒドロキシル基で置換されていてもよく、
nが、独立して、1、2、3、4、5、または6である、
請求項1に記載の感光性組成物。 - 基体にポリマー画像をパターニングする方法であって、
(a)請求項16に記載の感光性組成物の1以上の層を基体上に堆積させることと、
(b)前記感光性組成物の層の一部に250~800nmの範囲の波長を含んでなる光を照射して、前記層の照射部分を重合させ、それによって重合領域および非重合領域のパターン化層を得ることと、
(c)前記パターンの前記非重合領域を除去することと、を含んでなる方法。 - 液槽光重合を含んでなる方法であって、請求項1に記載の感光性組成物を並進または回転させている基体上に直接硬化させ、照射をステレオリソグラフィ、ホログラフィ、またはデジタル光プロジェクション(DLP)によりパターン化する前記方法。
- (a)メタセシス重合または架橋反応を経ることができる1以上のアルケンまたはアルキンを有する組成物の2以上の層を堆積することであって、前記堆積が積層体を形成することと、
(b)前記積層体の隣接層の少なくとも一部を重合または架橋するのに充分な条件下で、前記積層体の少なくとも一部に光を照射して、前記積層体の2以上の層に光を透過させ、照射することと、
を含んでなる方法であって、
1以上の層が、請求項1に記載の感光性組成物を含んでなる、方法。 - 前記積層体の隣接層の少なくとも一部を重合または架橋するのに充分な条件下で、前記積層体の全部の層に光を透過させ、照射する、請求項19に記載の方法。
- 前記照射を積層組成物へのパターン露光によって行い、それによって、前記積層体を通して重合領域および非重合領域の三次元パターンを得る、請求項19に記載の方法。
- 前記照射を、フォトマスクの使用により、直描光照射により、干渉、ナノインプリント、または回折勾配リソグラフィにより、インクジェット3Dプリンティング、ステレオリソグラフィ、ホログラフィ、またはデジタル光プロジェクション(DLP)により、パターン化する、請求項19に記載の方法。
- 1以上の層中のポリマーが、樹状(くさび状)またはブラシ状(接木状、びん洗いブラシ状)ブロックコポリマーである、請求項19に記載の方法。
- 2以上の順次堆積された層の隣接層が組成的に異なる、請求項19に記載の方法。
- 光重合された請求項1~9及び13~16のいずれか一項に記載の組成物を含む、重合組成物。
- パターン化ポリマー層である、請求項26に記載の重合組成物。
- 請求項26に記載の重合組成物を含む、パターン化三次元ポリマー構造。
- 請求項26又は27に記載の重合組成物を含む、組織スキャフォールド。
- さらに組織スキャフォールド上に接着した組織の集団又は細胞集団を含む、請求項29に記載の組織スキャフォールド。
- 請求項26に記載の重合組成物の層を少なくとも2層を含み、重合組成物の前記少なくとも2層が互いに隣接して、且つ互いに架橋されて配置される、三次元ポリマー積層体。
- 互いに隣接する重合組成物の前記少なくとも2層が互いに組成的に異なる、請求項31に記載の三次元ポリマー積層体。
- 請求項31に記載の三次元ポリマー積層体を含む、フォトニック構造体。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010229411A (ja) | 2001-08-24 | 2010-10-14 | California Inst Of Technology | 6配位ルテニウムまたはオスミウム金属カルベンメタセシス触媒 |
US20140099573A1 (en) | 2012-10-05 | 2014-04-10 | California Institute Of Technology | Photoinitiated olefin methathesis polymerization |
US20150118188A1 (en) | 2013-10-30 | 2015-04-30 | California Institute Of Technology | Direct photopatterning of robust and diverse materials |
WO2015063282A1 (en) | 2013-11-01 | 2015-05-07 | Dupont Nutrition Biosciences Aps | Use of algae to increase the viable active biomass of lactic acid bacteria |
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US20140099573A1 (en) | 2012-10-05 | 2014-04-10 | California Institute Of Technology | Photoinitiated olefin methathesis polymerization |
US20150118188A1 (en) | 2013-10-30 | 2015-04-30 | California Institute Of Technology | Direct photopatterning of robust and diverse materials |
WO2015063282A1 (en) | 2013-11-01 | 2015-05-07 | Dupont Nutrition Biosciences Aps | Use of algae to increase the viable active biomass of lactic acid bacteria |
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