perfluoroethyl-2,2-difluorovinyl ether

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: perfluoroethyl-2,2-difluorovinyl ether
• 英文别名: perfluorinated ethyl vinyl ether；1-(2,2-Difluoroethenoxy)-1,1,2,2,2-pentafluoroethane；1-(2,2-difluoroethenoxy)-1,1,2,2,2-pentafluoroethane
• 化学式: C₄HF₇O
• 分子量: 198.04
• InChiKey: DPHBJYBPRULFHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  perfluoroethyl 2-chloro-2,2-difluoroethyl ether 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到perfluoroethyl-2,2-difluorovinyl ether
  参考文献：
  名称：

  Novel hydrofluorocarbon polymers for use as pellicles in 157 nm semiconductor photolithography: fundamentals of transparency

  摘要：

  With the advent of 157 nm as the next photolithographic wavelength, there has been a need to find transparent and radiation durable polymers for use as soft pellicles. Pellicles are similar to1 mum thick polymer membranes used in the photolithographic reproduction of semiconductor integrated circuits to prevent dust particles on the surface of the photomask from imaging into the photoresist coated wafer. Practical pellicle films must transmit at least 98% of incident light and have sufficient radiation durability to withstand kilojoules of optical irradiation at the lithographic wavelength. As exposure wavelengths have become shorter the electronics industry has been able to achieve adequate transparency only by moving from nitrocellulose polymers to perfluorinated polymers as, for example, Teflon(R) AF 1600 and Cytop(TM) for use in 193 nm photolithography. Unfortunately, the transparency advantages of perfluorinated polymers fail spectacularly at 157 nm; I Put thick Cytop(TM) have 157 nm transparency of no more than 38 and 2%, respectively, with 157 nm pellicle lifetimes films of Teflon(R) AF 1600 and measured in millijoules.Polymers such as -[(CH2CHF)(x)C(CF3)(2)CH2](y)-, or -(CH2CF2)(x)[2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole](y)- with chains that alternate fluorocarbon segments with either oxygen or hydrocarbon segments frequently show >98% transparency at 157 nm, if amorphous. These polymers are made from monomers, such as vinylidene fluoride (VF2) and hexafluoroisobutylene, which themselves exhibit good alternation of CH2 and CF2 in their structures. In addition, we find that ether linkages also can serve to force alternation. In addition, we find that fluorocarbon segments shorter than six carbons, and hydrocarbon segments less than two carbons or less than three carbons if partially fluorinated also promote 157 nm transparency. We also find that even with these design principles, it is advantageous to avoid small rings, as arise in the cyclobutanes. These results suggest a steric component to transparency in addition to the importance of alternation.Upon irradiation these polymers undergo photochemical darkening and therefore none has demonstrated the kilojoule radiation durability lifetimes required to be commercially attractive. This is likely because these exposure lifetimes require every bond to absorb similar to10 photons, each photon having an energy roughly twice common bond energies. We have studied intrinsic (composition, molecular weight) and extrinsic (trace metals, impurities, environmental contaminants, oxygen, water) contributions to optical absorption and photochemical darkening in these polymers. Studies of photochemical darkening in model molecules illustrate the dynamics of photochemical darkening and that appreciable lifetimes can be achieved in fluorocarbons. To a first approximation the polymers that have lower 157 nm optical absorbance also tend to show the longest lifetimes. These results imply that quantum yield, or the extent to which the polymer structure can harmlessly dissipate the energy, can be important as well. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00081-2

文献信息

• METHOD FOR PREPARING FLUORINE-CONTAINING VINYL ETHER
  申请人：Zhonghao Chenguang Research Institute of Chemical Industry Company Limited

  公开号：EP2781500B1

  公开（公告）日：2017-11-08
• Novel hydrofluorocarbon polymers for use as pellicles in 157 nm semiconductor photolithography: fundamentals of transparency
  作者：Roger H French、Robert C Wheland、Weiming Qiu、M.F Lemon、Edward Zhang、Joseph Gordon、Viacheslav A Petrov、Victor F Cherstkov、Nina I Delaygina

  DOI：10.1016/s0022-1139(03)00081-2

  日期：2003.7

  With the advent of 157 nm as the next photolithographic wavelength, there has been a need to find transparent and radiation durable polymers for use as soft pellicles. Pellicles are similar to1 mum thick polymer membranes used in the photolithographic reproduction of semiconductor integrated circuits to prevent dust particles on the surface of the photomask from imaging into the photoresist coated wafer. Practical pellicle films must transmit at least 98% of incident light and have sufficient radiation durability to withstand kilojoules of optical irradiation at the lithographic wavelength. As exposure wavelengths have become shorter the electronics industry has been able to achieve adequate transparency only by moving from nitrocellulose polymers to perfluorinated polymers as, for example, Teflon(R) AF 1600 and Cytop(TM) for use in 193 nm photolithography. Unfortunately, the transparency advantages of perfluorinated polymers fail spectacularly at 157 nm; I Put thick Cytop(TM) have 157 nm transparency of no more than 38 and 2%, respectively, with 157 nm pellicle lifetimes films of Teflon(R) AF 1600 and measured in millijoules.Polymers such as -[(CH2CHF)(x)C(CF3)(2)CH2](y)-, or -(CH2CF2)(x)[2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole](y)- with chains that alternate fluorocarbon segments with either oxygen or hydrocarbon segments frequently show >98% transparency at 157 nm, if amorphous. These polymers are made from monomers, such as vinylidene fluoride (VF2) and hexafluoroisobutylene, which themselves exhibit good alternation of CH2 and CF2 in their structures. In addition, we find that ether linkages also can serve to force alternation. In addition, we find that fluorocarbon segments shorter than six carbons, and hydrocarbon segments less than two carbons or less than three carbons if partially fluorinated also promote 157 nm transparency. We also find that even with these design principles, it is advantageous to avoid small rings, as arise in the cyclobutanes. These results suggest a steric component to transparency in addition to the importance of alternation.Upon irradiation these polymers undergo photochemical darkening and therefore none has demonstrated the kilojoule radiation durability lifetimes required to be commercially attractive. This is likely because these exposure lifetimes require every bond to absorb similar to10 photons, each photon having an energy roughly twice common bond energies. We have studied intrinsic (composition, molecular weight) and extrinsic (trace metals, impurities, environmental contaminants, oxygen, water) contributions to optical absorption and photochemical darkening in these polymers. Studies of photochemical darkening in model molecules illustrate the dynamics of photochemical darkening and that appreciable lifetimes can be achieved in fluorocarbons. To a first approximation the polymers that have lower 157 nm optical absorbance also tend to show the longest lifetimes. These results imply that quantum yield, or the extent to which the polymer structure can harmlessly dissipate the energy, can be important as well. (C) 2003 Elsevier Science B.V. All rights reserved.