Photopatterning of Low Dielectric Constant Cycloolefin Polymers Using Azides and Diazirines

被引:32
作者
Burgoon, Hugh [1 ]
Cyrus, Crystal [1 ]
Skilskyj, Doug [1 ]
Thoresen, Jennifer [1 ]
Ebner, Carl [1 ]
Meyer, Gerhard A. [1 ]
Filson, Paul [1 ]
Rhodes, Larry F. [1 ]
Backlund, Tomas [2 ]
Meneau, Aurelie [2 ]
Cull, Toby [2 ]
Afonina, Irina [2 ]
机构
[1] Promerus LLC, Brecksville, OH 44141 USA
[2] Merck Chem Ltd, Southampton SO16 7QD, Hants, England
关键词
bis(azide); bis(diazirine); polynorbornene; photopatterning; low dielectric constant;
D O I
10.1021/acsapm.0c00043
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Polymers are widely used as insulators in electronic devices. Low dielectric constant polymers are desirable since this lowers the potential for unintentional crosstalk and inductive coupling between conductors. Attempts to photopattern a low dielectric constant polymer, poly(5-hexyl-2-norbornene) (poly(1)), with a bis(azide) were unsuccessful. Incorporation of butenyl pendent groups improved patterning, but the dielectric constant of the cross-linked film was relatively high (2.60). A difunctional bis(diazirine) (compound 4) was synthesized and characterized by NMR and MS. Compound 4 rendered unreactive, aliphatic cycloolefin polymers such as poly(1) photopatternable, yielding negative tone patterns with good resolution. The dielectric constant of films cross-linked with compound 4 was substantially lower than the films cross-linked with bis(azide) (2.09 for poly(1)).
引用
收藏
页码:1819 / 1826
页数:8
相关论文
共 25 条
[1]  
Ahne H, 1995, PHOTOSENSITIVE POLYI
[2]   A carbene insertion approach to functionalised poly(ethylene oxide)-based gels [J].
Blencowe, Anton ;
Blencowe, Chris ;
Cosstick, Kevin ;
Hayes, Wayne .
REACTIVE & FUNCTIONAL POLYMERS, 2008, 68 (04) :868-875
[3]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[4]   COMPLEXES OF (C6F5)2CO AND (C6F5)2NI - SYNTHESIS OF (ETA-6-ARENE)BIS(PENTAFLUOROPHENYL)COBALT(II) USING COBALT ATOMS - REACTIONS, ETA-6-ARENE LABILITY, AND USE IN SYNTHESIS OF TETRAHEDRAL (C6F5)2CO(L)2 [J].
BREZINSKI, MM ;
KLABUNDE, KJ .
ORGANOMETALLICS, 1983, 2 (09) :1116-1123
[5]  
BRUNNER J, 1980, J BIOL CHEM, V255, P3313
[6]  
Burgoon H, 2018, US Patent, Patent No. 9938241
[7]   The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis [J].
Fulton, JR ;
Aggarwal, VK ;
de Vicente, J .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1479-1492
[8]  
Grove NR, 1999, J POLYM SCI POL PHYS, V37, P3003, DOI 10.1002/(SICI)1099-0488(19991101)37:21<3003::AID-POLB10>3.0.CO
[9]  
2-T
[10]  
GUPTA T, 2009, COPPER INTERCONNECT, P1