JP2005314553A - Deep uv ray-transmitting adhesive - Google Patents

Deep uv ray-transmitting adhesive Download PDF

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Publication number
JP2005314553A
JP2005314553A JP2004134098A JP2004134098A JP2005314553A JP 2005314553 A JP2005314553 A JP 2005314553A JP 2004134098 A JP2004134098 A JP 2004134098A JP 2004134098 A JP2004134098 A JP 2004134098A JP 2005314553 A JP2005314553 A JP 2005314553A
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integer
adhesive
ocf
deep ultraviolet
deep
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Takashi Takahashi
高橋崇
Norio Tanaka
田中紀男
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TANAKA KOBUNSHI GIJUTSU KENKYU
TANAKA KOBUNSHI GIJUTSU KENKYUSHO KK
Topcon Corp
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TANAKA KOBUNSHI GIJUTSU KENKYU
TANAKA KOBUNSHI GIJUTSU KENKYUSHO KK
Topcon Corp
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an adhesive transparent in a deep UV range, enabling easy synthesis of a monomer and effective for avoiding the leakage of liquid. <P>SOLUTION: The deep UV ray-transmitting adhesive is composed of a substance expressed by general formula: H<SB>p</SB>¾(CH=CH-O-)<SB>n</SB>-R<SB>m</SB>-F<SB>q</SB>(R is carbon atom or carbon atom having oxygen atom; n is an integer; m is an integer; p is an integer including zero; and q is an integer). <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

本発明は、２００ｎｍ近傍、とくに１８０ｎｍから２２０ｎｍの深紫外域で用いることができる接着剤に関する。   The present invention relates to an adhesive that can be used in the vicinity of 200 nm, particularly in the deep ultraviolet region of 180 nm to 220 nm.

従来から、紫外域、特に深紫外域で用いられる半導体検査装置その他の精密機械検査装置等では、レンズ部材の貼り合わせに通常の接着剤が使えないことから、フッ素系オイル等の充填材が用いられている（特許文献１、２参照）。   Conventionally, in semiconductor inspection equipment and other precision mechanical inspection equipment used in the ultraviolet region, particularly in the deep ultraviolet region, a normal adhesive cannot be used for bonding lens members, so a filler such as fluorine-based oil has been used. (See Patent Documents 1 and 2).

また、特許文献３、４には、ＣＸ２＝ＣＹ２〔ここで、Ｘが−Ｆまたは−ＣＦ３でありそしてＹはＨである〕と０から２５モル％の１種以上の単量体ＣＲａＲｂ＝ＣＲｃＲｄ{ここで、Ｒａ、ＲｂおよびＲｃ、は、各々独立して、ＨまたはＦから選択され、そしてＲｄは、−Ｆ、−ＣＦ３、−ＯＲｆ〔ここで、ＲｆはＣｎＦ２ｎ＋１ｌ（ここで、ｎ＝１から３）である〕、−ＯＨ（Ｒｃ＝Ｈの時）およびＣｌ（Ｒａ、ＲｂおよびＲｃ＝Ｆの時）から成る群から選ばれる}から作られていてこの場合には前記ＣＲaＲb＝ＣＲcＲdがほぼランダム（ｒａｎｄｏｍ）な様式で共重合体の中に入り込んでいるか或はそれと４０から６０モル％の１種以上の単量体ＣＲaＲb＝ＣＲcＲdから作られていてこの場合には前記ＣＲaＲb＝ＣＲcＲdがほぼ交互（ａｌｔｅｒｎａｔｉｎｇ）様式で共重合体の中に入り込んでいる非晶質ビニル共重合体が開示されている。
特開２００３−１３７６１４号公報 特開２００３−１８５８０８号公報 特表２００３−５１４９５５号公報（ＷＯ０１／３７０４３Ａ１） 特表２００３−５１４９５６号公報（ＷＯ０１／３７０４４Ａ１） Patent Documents 3 and 4 include CX 2 = CY 2 [where X is —F or —CF 3 and Y is H] and 0 to 25 mol% of one or more monomers. CR a R b = CR c R d where R a , R b and R c are each independently selected from H or F, and R d is -F, -CF 3 , -OR f [where Rf is C n F 2n + 1 l (where n = 1 to 3)], —OH (when R c = H) and Cl (R a , R b and R c = F In this case, the CR a R b = CR c R d enters the copolymer in a substantially random manner or 40 To 60 mol% of one or more monomers CR a R b = CR c R d , in this case the CR Amorphous vinyl copolymers are disclosed in which a R b = CR c R d penetrates into the copolymer in an almost alternating manner.
JP 2003-137614 A Japanese Patent Laid-Open No. 2003-185808 Japanese translation of PCT publication No. 2003-514955 (WO01 / 37043A1) Japanese translation of PCT publication No. 2003-514956 (WO01 / 37044A1)

しかしながら、特許文献１、２に開示されたフッ素系オイルでは、液漏れを生じる可能性がある。その場合、作業性が著しく低くなってしまう。   However, the fluorinated oil disclosed in Patent Documents 1 and 2 may cause liquid leakage. In that case, workability will be remarkably lowered.

また、特許文献３、４に開示された接着剤（すなわち、１８７−２６０ｎｍの波長のところに示す吸収光度／ミクロン（Ａ／ミクロメートル）が、≦１である紫外透過性材料（ｕｌｔｒａｖｉｉｏｌｅｔ ｔｒａｎｓｐａｒｅｎｔ）を提供する接着剤）では、Ｃｙｔｏｐ（登録商標）およびＴｅｆｌｏｎ（登録商標）の単量体の合成が困難である。それとともに、これらの単量体の合成も困難である。そのため、結果的に高価になってしまう。   Further, an adhesive disclosed in Patent Documents 3 and 4 (that is, an ultraviolet transmissive material having an absorption luminous intensity / micron (A / micrometer) shown at a wavelength of 187 to 260 nm of ≦ 1) is used. With the provided adhesives, it is difficult to synthesize Cytop® and Teflon® monomers. At the same time, it is difficult to synthesize these monomers. Therefore, it becomes expensive as a result.

そこで、本発明は、単量体の合成を簡易に行うことができるとともに、液漏れを回避できる、深紫外域で使用可能な接着剤を提供することを目的とする。   Accordingly, an object of the present invention is to provide an adhesive that can be used in the deep ultraviolet region and that can easily synthesize monomers and avoid liquid leakage.

本発明の解決手段を例示すると、下記一般式で表わされる物質からなり、深紫外線が透過する深紫外線透過接着剤である。   Illustrating the solution of the present invention, it is a deep ultraviolet light transmitting adhesive made of a substance represented by the following general formula and capable of transmitting deep ultraviolet light.


Ｈｐ
｜
（ＣＨ＝ＣＨ−Ｏ−）ｎ−Ｒｍ−Ｆｑ

Ｒ＝ 炭素、又は酸素原子を有する炭素
ｎ＝ 整数
ｍ＝ 整数
ｐ＝ 整数（０を含む）
ｑ＝ 整数
Hp
｜
(CH═CH—O—) n —R m —Fq

R = carbon or carbon having an oxygen atom n = integer m = integer p = integer (including 0)
q = integer

本発明に係る深紫外域で用いることができる接着剤は、下記化学式で表わされる。   The adhesive which can be used in the deep ultraviolet region according to the present invention is represented by the following chemical formula.

すなわち、
Ｈｐ
｜
（ＣＨ＝ＣＨ−Ｏ−）ｎ−Ｒｍ−Ｆｑ
ここで、
Ｒ＝ 炭素、又は酸素原子を有する炭素
ｎ＝ 整数
ｍ＝ 整数
ｐ＝ 整数（０を含む）
ｑ＝ 整数
である。 That is,
Hp
｜
(CH═CH—O—) n —R m —Fq
here,
R = carbon or carbon having an oxygen atom n = integer m = integer p = integer (including 0)
q = integer.

接着剤の液体を固体化させるため、触媒（硬化剤）を用いるのが好ましい。   In order to solidify the liquid of the adhesive, it is preferable to use a catalyst (curing agent).

この触媒は、深ＵＶ波長域で光を吸収するものとする。   This catalyst absorbs light in the deep UV wavelength region.

また、本発明の接着剤の好ましい具体例を下記に示す。なお、本発明は、ここに記載した化合物だけに限定されるものではない。   Moreover, the preferable specific example of the adhesive agent of this invention is shown below. In addition, this invention is not limited only to the compound described here.


ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＦ２ＣＦ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＦ２ＣＦ２ＣＦ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＦ２ＣＦ２ＣＦ２ＣＦ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−（ＣＦ２）６−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−（ＣＦ２）８−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−（ＣＦ２）１０−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−（ＣＦ２）１２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
…
帰納的に下記の一般式に表わされる。すなわち、
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−（ＣＦ２）２ｎ−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２ （ｎは自然数）

ＣＨ２＝ＣＨ−ＣＨ２−ＯＣＦ２ＣＦ２ＯＣＦ２ＣＦ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＯＣＦ２ＣＦ２−）２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＯＣＦ２ＣＦ２−）３−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＯＣＦ２ＣＦ２−）４−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＯＣＦ２ＣＦ２−）６−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
…
帰納的に下記の一般式に表わされる。すなわち、
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＯＣＦ２ＣＦ２−）ｎ−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２

ＣＨ２＝ＣＨ−ＣＨ２−ＯＣＦ２ＣＦ２ＣＦ２ＯＣＦ２ＣＦ２ＣＦ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
…
帰納的に下記の一般式に表わされる。すなわち、
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＣＦ２ＯＣＦ２ＣＦ２ＣＦ２−）ｎ−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２

ＣＨ２＝ＣＨ−ＣＨ２−ＯＣＦ２ＣＦ２ＣＦ２ＣＦ２ＯＣＦ２ＣＦ２ＣＦ２ＣＦ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
…
ＣＨ２＝ＣＨ−ＣＨ２−（−ＯＣＦ２ＣＦ２ＣＦ２ＣＦ２ＯＣＦ２ＣＦ２ＣＦ２ＣＦ２−）ｎ−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２

また、下記の一般式で表わされる化学物質を含む接着剤であってもよい。すなわち、

ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＨ２−ＣＦ２−（−ＯＣ２Ｆ４−）ｐ−Ｏ−（−ＣＦ２−）ｑ−ＯＣＦ２−ＣＨ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２

Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
｜
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＨ２−ＣＨ−ＣＨ２Ｏ−ＣＨ２−ＣＦ２−
（−ＯＣ２Ｆ４−）ｐ−（−ＯＣＦ２−）ｑ−ＯＣＦ２−ＣＨ２−Ｏ−ＣＨ２
−ＣＨ−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
｜
ＣＨ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２

Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
｜
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＨ２−Ｃ−ＣＨ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
｜
Ｆ
CH 2 = CH-CH 2 -O -CF 2 CF 2 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 -O -CF 2 CF 2 CF 2 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 -O -CF 2 CF 2 CF 2 CF 2 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 -O- (CF 2) 6 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 -O- (CF 2) 8 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 -O- (CF 2) 10 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 -O- (CF 2) 12 -O-CH 2 -CH = CH 2
...
Inductively, it is expressed in the following general formula. That is,
CH 2 = CH-CH 2 -O- (CF 2) 2n -O-CH 2 -CH = CH 2 (n is a natural number)

CH 2 = CH-CH 2 -OCF 2 CF 2 OCF 2 CF 2 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 - (- OCF 2 CF 2 OCF 2 CF 2 -) 2 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 - (- OCF 2 CF 2 OCF 2 CF 2 -) 3 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 - (- OCF 2 CF 2 OCF 2 CF 2 -) 4 -O-CH 2 -CH = CH 2
CH 2 = CH-CH 2 - (- OCF 2 CF 2 OCF 2 CF 2 -) 6 -O-CH 2 -CH = CH 2
...
Inductively, it is expressed in the following general formula. That is,
CH 2 = CH-CH 2 - (- OCF 2 CF 2 OCF 2 CF 2 -) n -O-CH 2 -CH = CH 2

CH 2 = CH-CH 2 -OCF 2 CF 2 CF 2 OCF 2 CF 2 CF 2 -O-CH 2 -CH = CH 2
...
Inductively, it is expressed in the following general formula. That is,
CH 2 = CH-CH 2 - (- OCF 2 CF 2 CF 2 OCF 2 CF 2 CF 2 -) n -O-CH 2 -CH = CH 2

CH 2 = CH-CH 2 -OCF 2 CF 2 CF 2 CF 2 OCF 2 CF 2 CF 2 CF 2 -O-CH 2 -CH = CH 2
...
CH 2 = CH-CH 2 - (- OCF 2 CF 2 CF 2 CF 2 OCF 2 CF 2 CF 2 CF 2 -) n -O-CH 2 -CH = CH 2

Moreover, the adhesive agent containing the chemical substance represented by the following general formula may be sufficient. That is,

CH 2 = CH-CH 2 -O -CH 2 -CF 2 - (- OC 2 F 4 -) p -O - (- CF 2 -) q -OCF 2 -CH 2 -O-CH 2 -CH = CH 2

O—CH 2 —CH═CH 2
｜
CH 2 = CH-CH 2 -O -CH 2 -CH-CH 2 O-CH 2 -CF 2 -
(—OC 2 F 4 —) p — (— OCF 2 —) q —OCF 2 —CH 2 —O—CH 2
—CH—O—CH 2 —CH═CH 2
｜
CH 2 -O-CH 2 -CH = CH 2

O—CH 2 —CH═CH 2
｜
CH 2 = CH-CH 2 -O -CH 2 -C-CH 2 -O-CH 2 -CH = CH 2
｜
F

以下、４種類の接着剤について、光学特性、特に反射率の特性データを示す。   In the following, optical characteristics, particularly reflectance characteristic data are shown for four types of adhesives.


サンプル１

Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
｜
ＣＨ２＝ＣＨ−ＣＨ２−Ｏ−ＣＨ２−Ｃ−ＣＨ２−Ｏ−ＣＨ２−ＣＨ＝ＣＨ２
｜
Ｆ

図１は、サンプル１の接着剤を石英ガラス基板に塗布して硬化させた光学部材と、石英ガラス基板のみの光学部材に、それぞれ紫外線を照射し、透過率の変化を示すものである。
Sample 1

O—CH 2 —CH═CH 2
｜
CH 2 = CH-CH 2 -O -CH 2 -C-CH 2 -O-CH 2 -CH = CH 2
｜
F

FIG. 1 shows changes in transmittance by irradiating an optical member obtained by applying the adhesive of sample 1 on a quartz glass substrate and curing the optical member and an optical member including only the quartz glass substrate, respectively.

図１に示された光学特性、特に反射率の特性データからも明らかなように、サンプル１の接着剤を使用した場合、２００ｎｍ近傍、とくに１８０〜２２０ｎｍの深紫外線に対して、４０％以上（特に好ましくは６０％以上）の透過率を示す。約２１０ｎｍ以上の深紫外線に対しては、サンプル１の接着剤を石英ガラス基板に使用した光学部材と、石英ガラス基板のみの光学部材との間で、透過率に実質的な差が認められない。   As is clear from the optical characteristics shown in FIG. 1, particularly the reflectance characteristics data, when the adhesive of Sample 1 is used, it is 40% or more (in the vicinity of 200 nm, particularly 180-220 nm deep ultraviolet rays) ( The transmittance of 60% or more is particularly preferable. For deep ultraviolet rays of about 210 nm or more, there is no substantial difference in transmittance between the optical member using the adhesive of sample 1 for the quartz glass substrate and the optical member using only the quartz glass substrate. .

変形例１
ＣＨ２＝ＣＨＣＨ２０ＣＦ２（ＣＦ２）６ＣＦ２０ＣＨ２ＣＨ＝ＣＨ２
変形例２
ＣＨ２＝ＣＨＣＨ２０（ＣＦ２）６０ＣＨ２ＣＨ＝ＣＨ２
変形例３
ＣＨ２＝ＣＨＣＨ２０ＣＦ２（ＣＦ２）４ＣＦ２０ＣＨ２ＣＨ＝ＣＨ２
図２、３、４は、それぞれ変形例１、２、３の各々の接着剤を塗布した光学部材に各図２、３、４に示す時間紫外線を照射し、透過率を測定したものである。 Modification 1
CH 2 = CHCH 2 0CF 2 (CF 2 ) 6 CF 2 0CH 2 CH = CH 2
Modification 2
CH 2 = CHCH 2 0 (CF 2 ) 6 0CH 2 CH = CH 2
Modification 3
CH 2 = CHCH 2 0CF 2 (CF 2 ) 4 CF 2 0CH 2 CH = CH 2
2, 3, and 4 are obtained by measuring the transmittance by irradiating the optical members coated with the adhesives of the modified examples 1, 2, and 3 with ultraviolet rays for the time shown in FIGS. .

図２、３、４をみると、２００ｎｍ近傍以上の深紫外線に対して、所望の透過率を示し、しかも、深紫外線の照射時間が長くなれば長くなるほど、透過率が安定することがわかる。   2, 3, and 4, it can be seen that the desired transmittance is shown for deep ultraviolet rays of around 200 nm or more, and the transmittance becomes more stable as the irradiation time of deep ultraviolet rays becomes longer.

本発明による接着剤は、好ましくは、透明なポリマー素材である。そのような透明なポリマー素材は、ジメチルシリコンオリゴマー（油）またはフッ素系オリゴマー（油）に可視光反応型触媒を入れて合成すれば、容易に作ることができる。   The adhesive according to the invention is preferably a transparent polymer material. Such a transparent polymer material can be easily prepared by synthesizing a dimethyl silicon oligomer (oil) or a fluorine-based oligomer (oil) with a visible light reactive catalyst.

紫外線照射による透過率の変化を示すグラフ。The graph which shows the change of the transmittance | permeability by ultraviolet irradiation. 変形例１についての透過率と波長との関係を示すグラフ。The graph which shows the relationship between the transmittance | permeability about a modification 1, and a wavelength. 変形例２についての透過率と波長との関係を示すグラフ。The graph which shows the relationship between the transmittance | permeability and the wavelength about the modification 2. 変形例３についての透過率と波長との関係を示すグラフ。The graph which shows the relationship between the transmittance | permeability and the wavelength about the modification 3.

Claims (3)

下記一般式で表わされる物質からなり、深紫外線が透過する深紫外線透過接着剤。

Ｈｐ
｜
（ＣＨ＝ＣＨ−Ｏ−）ｎ−Ｒｍ−Ｆｑ

Ｒ＝ 炭素、又は酸素原子を有する炭素
ｎ＝ 整数
ｍ＝ 整数
ｐ＝ 整数（０を含む）
ｑ＝ 整数 A deep ultraviolet light transmissive adhesive made of a material represented by the following general formula and capable of transmitting deep ultraviolet light.

Hp
｜
(CH═CH—O—) n —R m —Fq

R = carbon or carbon having an oxygen atom n = integer m = integer p = integer (including 0)
q = integer 透明なポリマー素材である、請求項１に記載の深紫外線透過接着剤。   The deep ultraviolet light transmitting adhesive according to claim 1, which is a transparent polymer material. ジメチルシリコンオリゴマー（油）またはフッ素系オリゴマー（油）に可視光反応型触媒を入れて合成することによって作られている、請求項１又は２に記載の深紫外線透過接着剤。

The deep ultraviolet ray transmitting adhesive according to claim 1 or 2, wherein the adhesive is made by synthesizing a dimethyl silicon oligomer (oil) or a fluorine-based oligomer (oil) with a visible light reactive catalyst.

JP2004134098A 2004-04-28 2004-04-28 Deep uv ray-transmitting adhesive Pending JP2005314553A (en)

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