JP2997105B2 - Insulating films for semiconductors and methods for forming them - Google Patents
Insulating films for semiconductors and methods for forming themInfo
- Publication number
- JP2997105B2 JP2997105B2 JP3235388A JP23538891A JP2997105B2 JP 2997105 B2 JP2997105 B2 JP 2997105B2 JP 3235388 A JP3235388 A JP 3235388A JP 23538891 A JP23538891 A JP 23538891A JP 2997105 B2 JP2997105 B2 JP 2997105B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- group
- film
- polyorganosilsesquioxane
- general formula
- 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
- 238000000034 method Methods 0.000 title claims description 23
- 239000004065 semiconductor Substances 0.000 title claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000009413 insulation Methods 0.000 claims 1
- 238000000576 coating method Methods 0.000 description 33
- 239000011248 coating agent Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000001723 curing Methods 0.000 description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000011229 interlayer Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- -1 polysiloxane Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZJBHFQKJEBGFNL-UHFFFAOYSA-N methylsilanetriol Chemical compound C[Si](O)(O)O ZJBHFQKJEBGFNL-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Landscapes
- Formation Of Insulating Films (AREA)
- Organic Insulating Materials (AREA)
- Silicon Polymers (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は半導体における多層配線
化に必要とされる絶縁膜または平坦化膜としてポリオル
ガノシルセスキオキサンを用いて製造された新規な半導
体用絶縁膜または平坦化膜及びそれらを形成する方法に
関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel semiconductor insulating film or flattening film manufactured by using polyorganosilsesquioxane as an insulating film or flattening film required for multi-layer wiring in a semiconductor. It relates to a method of forming them.
【０００２】[0002]
【従来の技術】ＬＳＩの高集積化とともに配線の多層化
が不可避となってきており、回路の信頼性を維持する上
で層間絶縁膜及び平坦化膜の重要性が増してきている。2. Description of the Related Art With the increase in integration of LSIs, multilayer wiring has become unavoidable, and the importance of interlayer insulating films and flattening films has been increasing in maintaining circuit reliability.
【０００３】層間絶縁膜または平坦化膜（本発明におい
ては以下この両者を層間絶縁膜等という。）の形成方法
には一般に気相法（ＣＶＤ法）と塗布膜法（ＳＯＧ法）
とが従来知られている。すなわちこれらの層間絶縁膜等
は信頼性の高い気相法により緻密なＳｉＯ2 膜を堆積す
る方法、あるいはテトラヒドロキシシランに代表される
無機系のポリシロキサン被覆膜を塗布法で形成すると共
に、この被覆膜を上下面を気相法による緻密なＳｉＯ2
膜で包むサンドイッチする方法とが採用されてきた。In general, a method of forming an interlayer insulating film or a planarizing film (both of them are referred to as an interlayer insulating film in the present invention) is a gas phase method (CVD method) and a coating film method (SOG method).
Is conventionally known. That is, these interlayer insulating films and the like are formed by a method of depositing a dense SiO 2 film by a highly reliable vapor phase method, or by forming an inorganic polysiloxane coating film represented by tetrahydroxysilane by a coating method, The upper and lower surfaces of this coating film are dense SiO 2 formed by a gas phase method.
A method of sandwiching with a film has been adopted.
【０００４】しかし、半導体の高集積化が進むにつれ、
配線幅、パタン間の溝が狭くなり、従って素子表面の凹
凸は大きくなる方法にあり、従来の気相法のみではこの
凹凸によって上層の配線が断線等の欠陥を生ずる恐れが
出てきた。However, as the degree of integration of semiconductors increases,
There is a method in which the width of the wiring and the groove between the patterns are narrowed, so that the unevenness on the element surface is increased. With the conventional vapor phase method alone, there is a possibility that the unevenness may cause a defect such as disconnection of the wiring in the upper layer.
【０００５】一方、塗布膜法においても、デバイス表面
の凹凸を埋めるには膜厚を従来より厚くしなければなら
ないわけであるが、無機ＳＯＧ膜であるテトラヒドロキ
シシラン硬化膜は膜厚０．２μｍ以上ではクラックを生
じやすい欠点があって、厚い配線の層間絶縁膜等に使用
するには問題があった。On the other hand, in the coating film method, the film thickness must be made larger than before in order to fill the unevenness of the device surface. However, the cured film of tetrahydroxysilane, which is an inorganic SOG film, has a thickness of 0.2 μm. Above, there is a drawback that cracks are easily generated, and there is a problem in using it for an interlayer insulating film having a thick wiring.
【０００６】そこで近時塗布膜法に使用されるテトラヒ
ドロキシシラン系被膜の厚膜化、耐クラック性や平坦化
能力を改良したものとして、アルキルトリヒドロキシシ
ランなどのいわゆる有機ＳＯＧを層間絶縁膜等として使
用することが提案されている。この場合は溝部を除いて
硬化膜を除去するエッチバック法が併用されることが多
い。To improve the thickness, crack resistance and flattening ability of a tetrahydroxysilane-based film used in the recent coating film method, a so-called organic SOG such as alkyltrihydroxysilane is used as an interlayer insulating film. It has been proposed to be used as In this case, an etch-back method for removing the cured film except for the grooves is often used in combination.
【０００７】しかし、この有機ＳＯＧ硬化膜にもいくつ
かの問題点があることが指摘されている。その一つは高
温加熱時の収縮による応力が大きく、クラック発生の懸
念があることであり、また高温加熱時の脱ガスによる配
線の損傷も懸念される。更に有機ＳＯＧ膜は無機ＳＯＧ
膜と比較したときに吸湿性が高いことも配線の信頼性の
面で不安視されている。However, it has been pointed out that this organic SOG cured film has some problems. One of them is that stress due to shrinkage during high-temperature heating is large, and there is a concern that cracks may occur. In addition, wiring may be damaged due to degassing during high-temperature heating. Further, the organic SOG film is made of inorganic SOG.
It is also considered uneasy in terms of wiring reliability that the film has a higher hygroscopicity than the film.
【０００８】[0008]
【発明が解決しようとする課題】本発明は有機ＳＯＧに
おける上記の問題点を解決する目的でなされたものであ
り、絶縁性、平坦化性に優れると共に、前述の耐熱性、
耐湿性等について改善された半導体用絶縁膜、平坦化膜
及びそれらの形成方法を提供することを目的とする。SUMMARY OF THE INVENTION The present invention has been made for the purpose of solving the above-mentioned problems in the organic SOG, and has an excellent insulating property and a flattening property.
It is an object of the present invention to provide an insulating film for semiconductors, a planarizing film, and a method for forming the same, which have improved moisture resistance and the like.
【０００９】[0009]
【課題を解決するための手段】本発明者らは上記目的を
達成するため鋭意検討を進めた結果、有機ＳＯＧにおけ
るアルキルトリヒドロキシシランに代えて特定の分子量
と末端基を有するポリオルガノシルセスキオキサンを用
いることにより、上記目的を達成する絶縁膜、平坦化膜
が得られることを見いだし、本発明を完成するに至っ
た。即ち、本発明は一般式（Ｉ）で示される数平均分子
量が５００〜１０，０００であり、末端基として水酸基
を０．３〜６重量％、アルコキシ基を０．９〜１６重量
％、かつ両末端基のモル比は１：０．２〜２．０の範囲
に含有しているポリオルガノシルセスキオキサンを加熱
キュアしたことを特徴とする半導体用絶縁膜または平坦
化膜に関する。Means for Solving the Problems The present inventors have made intensive studies to achieve the above object, and as a result, have found that polyorganosilsesquioxo having a specific molecular weight and a terminal group in place of alkyltrihydroxysilane in organic SOG. The inventors have found that an insulating film and a flattening film that achieve the above object can be obtained by using sun, and have completed the present invention. That is, the present invention has a number average molecular weight represented by the general formula (I) of 500 to 10,000, a hydroxyl group as a terminal group of 0.3 to 6% by weight, an alkoxy group of 0.9 to 16% by weight, and The present invention relates to an insulating film for semiconductor or a flattening film obtained by heating and curing polyorganosilsesquioxane containing a molar ratio of both terminal groups in the range of 1: 0.2 to 2.0.
【００１０】[0010]
【化２】 （一般式（Ｉ）においてＲ1 はメチル基またはフェニル
基、Ｒ2 は炭素数１〜３のアルキル基または水素原子を
示し、ｎは分子量に対応する正の数であり、分散を伴う
集合体を示す。）Embedded image (In the general formula (I), R 1 represents a methyl group or a phenyl group; R 2 represents an alkyl group having 1 to 3 carbon atoms or a hydrogen atom; n is a positive number corresponding to the molecular weight; Is shown.)
【００１１】また、上記半導体用層間絶縁膜等を形成す
るために、一般式（Ｉ）で示されるポリオルガノシロキ
サンを有機溶剤に溶解し、デバイス基板の配線上にコー
ティングし、加熱キュアする層間絶縁膜等を形成する方
法に関する。Further, in order to form the above-mentioned interlayer insulating film for a semiconductor, etc., the polyorganosiloxane represented by the general formula (I) is dissolved in an organic solvent, coated on the wiring of the device substrate, and cured by heating. The present invention relates to a method for forming a film or the like.
【００１２】本発明において使用されるポリオルガノシ
ルセスキオキサンにおいて側鎖Ｒ1はメチル基またはフ
ェニル基であり、これ以外の置換基では耐熱性が不十分
となり不適当である。またメチル基は少なくとも８０モ
ル％以上含有することが耐熱性の面で好ましい。In the polyorganosilsesquioxane used in the present invention, the side chain R 1 is a methyl group or a phenyl group, and other substituents are not suitable because of insufficient heat resistance. It is preferable that the content of the methyl group is at least 80 mol% or more from the viewpoint of heat resistance.
【００１３】本発明に用いるポリオルガノシルセスキオ
キサンとしては、末端基は水酸基を０．３〜６重量％、
アルコキシ基を０．９〜１６重量％、かつ両末端基のモ
ル比は１：０．２〜２．０の範囲となるよう含有するも
のである。アルコキシ基としてはメトキシ、エトキシ、
プロポキシ基等が使用しうる。The polyorganosilsesquioxane used in the present invention has a terminal group having a hydroxyl group of 0.3 to 6% by weight,
It contains an alkoxy group in an amount of 0.9 to 16% by weight and a molar ratio of both terminal groups in a range of 1: 0.2 to 2.0. Alkoxy groups include methoxy, ethoxy,
Propoxy groups and the like can be used.
【００１４】本発明のポリオルガノシルセスキオキサン
において末端基の水酸基が６重量％以上となるとキュア
後も未反応で残留する水酸基があり、これに起因して硬
化膜の吸湿性が高くなる欠点を生ずる。末端基のアルコ
キシ基が１６重量％以上では硬化膜の高温加熱時のガス
発生量が多くなる欠点を生ずる。また末端基の水酸基が
０．３重量％以下またはアルコキシ基が０．９重量％以
下の場合は基板との接着性や平坦化特性が不満足となる
ほかに、硬化膜の硬度なども目的に充分なレベルに達し
ない。また末端基の水酸基とアルコキシ基とのモル比は
１：０．２〜２．０、好ましくは１：０．５〜１．５で
あり、この範囲よりアルコキシ基が多くても少なくても
キュア時の性能発現はスムーズに進行しない。アルコキ
シ基が少ない場合は特に硬化膜の吸湿性が不満足とな
り、アルコキシ基が多い場合は高温加熱時のガス発生量
が問題となる。In the polyorganosilsesquioxane of the present invention, when the hydroxyl group of the terminal group is 6% by weight or more, there is a hydroxyl group which remains unreacted even after curing, resulting in an increased hygroscopicity of the cured film. Is generated. When the terminal alkoxy group content is 16% by weight or more, a disadvantage arises in that the amount of gas generated when the cured film is heated at a high temperature is increased. When the hydroxyl group of the terminal group is 0.3% by weight or less or the alkoxy group is 0.9% by weight or less, the adhesion to the substrate and the flattening characteristics are unsatisfactory, and the hardness of the cured film is sufficient for the purpose. Does not reach a certain level. The molar ratio between the terminal hydroxyl group and the alkoxy group is from 1: 0.2 to 2.0, preferably from 1: 0.5 to 1.5. The performance manifestation at the time does not proceed smoothly. When the amount of the alkoxy group is small, the hygroscopicity of the cured film becomes particularly unsatisfactory.
【００１５】本発明におけるポリオルガノシルセスキオ
キサンの数平均分子量は５００〜１０，０００が好まし
く、数平均分子量が５００より小さいと本発明の目的の
一つである高温加熱時及び硬化時の収縮を抑制する点で
不十分となる。また数平均分子量が１０，０００より大
きいと有機溶剤に対する溶解性が不十分となるのみなら
ず、平坦化特性も不満足となる。The number average molecular weight of the polyorganosilsesquioxane in the present invention is preferably from 500 to 10,000, and when the number average molecular weight is smaller than 500, shrinkage during heating at high temperature and curing which is one of the objects of the present invention. Is not sufficient in terms of suppressing On the other hand, when the number average molecular weight is more than 10,000, not only the solubility in an organic solvent becomes insufficient, but also the flattening characteristics become unsatisfactory.
【００１６】本発明のポリオルガノシルセスキオキサン
の基板配線上にコーティングするに当たっては有機溶剤
に溶解した液として用いる。本発明の分子量域のポリオ
ルガノシルセスキオキサンは多様な一般有機溶剤に可溶
であって、例えば次のような有機溶剤を用いることがで
きる。メチルアルコール、エチルアルコール、プロピル
アルコール、ブチルアルコールのようなアルコール類、
アセトン、メチルエチルケトン、メチルイソブチルケト
ンのようなケトン類、酢酸メチル、酢酸ブチルのような
エステル類、エチレングリコール、グリセリン、ジエチ
レングリコール、エチレングリコールモノメチルエーテ
ル、エチレングリコールエチルエーテル、エチレングリ
コールモノブチルエーテル、プロピレングリコールのよ
うな多価アルコールおよびそのエーテル類などを挙げる
ことができ、これらは単独で用いても２種以上混合して
用いてもよい。In coating the polyorganosilsesquioxane of the present invention on the substrate wiring, it is used as a solution dissolved in an organic solvent. The polyorganosilsesquioxane having a molecular weight range of the present invention is soluble in various general organic solvents. For example, the following organic solvents can be used. Alcohols such as methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol,
Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; esters such as methyl acetate and butyl acetate; ethylene glycol, glycerin, diethylene glycol, ethylene glycol monomethyl ether, ethylene glycol ethyl ether, ethylene glycol monobutyl ether, and propylene glycol And polyhydric alcohols and ethers thereof. These may be used alone or in combination of two or more.
【００１７】有機溶液中のポリオルガノシルセスキオキ
サンの固形分濃度はコーティング方法にも依存するが、
通常は２〜３０重量％、好ましくは５〜２０重量％であ
る。また本発明のポリオルガノシルセスキオキサン溶液
には必要に応じてレベリング剤、カップリング剤、増粘
剤、充填剤、その他の添加剤を添加して用いてもよい。The solid concentration of the polyorganosilsesquioxane in the organic solution also depends on the coating method.
Usually, it is 2 to 30% by weight, preferably 5 to 20% by weight. Further, the polyorganosilsesquioxane solution of the present invention may be used by adding a leveling agent, a coupling agent, a thickener, a filler, and other additives as necessary.
【００１８】本発明のポリオルガノシルセスキオキサン
溶液を基板配線上にコーティングするに際しては通常ス
ピンコーティングを行う。またこのとき配線上にあらか
じめ気相法によるＳｉＯ2 膜をつけておくのが一般的で
ある。When coating the polyorganosilsesquioxane solution of the present invention on substrate wiring, spin coating is usually performed. At this time, it is general that a SiO 2 film is formed on the wiring in advance by a vapor phase method.
【００１９】本発明のポリオルガノシルセスキオキサン
の膜厚は０．０１〜５μｍ程度まで自由に選択すること
ができ、特に１μｍ以上の厚膜になってもクラックを生
じないことから配線幅の凹部を一度に埋め平坦化するこ
とが可能である。The thickness of the polyorganosilsesquioxane of the present invention can be freely selected from about 0.01 to 5 μm. In particular, cracks do not occur even when the thickness is 1 μm or more. It is possible to fill the recesses at once and flatten them.
【００２０】加熱キュアとしてはポリオルガノシルセス
キオキサン溶液を基板にコーティングした後、１５０〜
５００℃において１０〜１２０分間加熱することによっ
て行う。このとき有機溶剤の種類によってはキュアに先
立ち１００〜３００℃、１〜１０分間の予備加熱を行
い、有機溶剤をあらかじめ除去してもよい。As the heating cure, after coating the substrate with a polyorganosilsesquioxane solution,
It is performed by heating at 500 ° C. for 10 to 120 minutes. At this time, depending on the type of the organic solvent, preliminary heating may be performed at 100 to 300 ° C. for 1 to 10 minutes prior to curing to remove the organic solvent in advance.
【００２１】キュア温度は構成材料の耐熱性から許容さ
れる限り高温にすることが硬化後の膜の材質及び所要時
間の面から望ましいが、通常は３００〜４５０℃にする
ことが好ましい。The curing temperature is desirably as high as possible from the viewpoint of the heat resistance of the constituent materials, from the viewpoint of the material of the cured film and the required time, but is usually preferably 300 to 450 ° C.
【００２２】本発明のポリオルガノシルセスキオキサン
は従来のアルキルトリヒドロキシシラン等の有機ＳＯＧ
よりは比較的低温でキュアすることができるばかりでな
く、このとき得られた硬化膜は比較的厚膜としてもクラ
ックは生じ難く、従来の有機ＳＯＧ膜に比して高温加熱
時にもガス発生量が少なく、また加熱に伴う収縮やクラ
ックも更に吸湿性、平坦化特性も良好な層間絶縁膜等が
得られる。The polyorganosilsesquioxane of the present invention is a conventional organic SOG such as alkyltrihydroxysilane.
In addition to curing at a relatively low temperature, the cured film obtained at this time is less likely to crack even if formed as a relatively thick film. In addition, an interlayer insulating film or the like having less heat shrinkage and cracks due to heating, and having good hygroscopicity and flattening characteristics can be obtained.
【００２３】[0023]
【作用】本発明のポリオルガノシロキサンは結果的には
テトラヒドロキシシランの問題点とアルキルトリヒドロ
キシシランの問題点を前記両者の長所を発揮できるよう
にポリオルガノシルセスキオキサンの分子量、置換基等
を適宜選択してこれを達成したものと考えることができ
る。The polyorganosiloxane of the present invention can finally solve the problems of tetrahydroxysilane and alkyltrihydroxysilane so that the advantages of both can be exerted, such as the molecular weight and substituents of polyorganosilsesquioxane. Can be appropriately selected to achieve this.
【００２４】特にラダータイプのオルガノシロキサンで
あるため熱安定性（加熱による収縮性の小さいこと）に
優れており、また末端基に一定範囲のアルコキシ基を含
有させることにより柔軟性（硬度）、接着性、平坦化特
性などをクラックや吸湿性によるトラブルがない適当な
範囲に納められるように分子設計された優れた層間絶縁
膜等を提供できた。Particularly, since it is a ladder type organosiloxane, it has excellent heat stability (small shrinkage by heating), and has flexibility (hardness) and adhesion by containing a certain range of alkoxy groups in the terminal groups. An excellent interlayer insulating film or the like having a molecular design so that the properties and flattening properties can be kept within an appropriate range without any trouble due to cracks or moisture absorption can be provided.
【００２５】[0025]
【実施例】以下、実施例及び比較例を挙げて本発明を更
に詳細に説明する。但し、本発明はなんらこれらに限定
されるものではない。なお、実施例及び比較例中の各物
性値はベアシリコンウエハに塗布したものを下記の方法
に従って測定した。The present invention will be described below in more detail with reference to examples and comparative examples. However, the present invention is not limited to these. In addition, each physical property value in an Example and a comparative example measured what applied to the bare silicon wafer according to the following method.
【００２６】（１）数平均分子量の測定 ＧＰＣ（ゲルバーミュレーションクロマトグラフィー）
法により測定したデータ（昭和電工（株）のＳｈｏｄｅ
ｘカラム使用）をポリスチレン標準試料の検量線に基づ
く換算値で表した。(1) Measurement of number average molecular weight GPC (gel permeation chromatography)
(Showa Denko Corporation's Shode
x column used) was represented by a converted value based on a calibration curve of a polystyrene standard sample.
【００２７】 （２）末端−ＯＨ、−ＯＣ２ Ｈ５ 基量の測定 液中に酸を加えることにより−ＯＨ基はＨ２ Ｏ、−Ｏ
Ｃ２ Ｈ５ 基はＣ２ Ｈ５ ＯＨとして滴定法により末端
−ＯＨ、−ＯＣ２ Ｈ５ を定量した。(2) Measurement of Terminal —OH, —OC 2 H 5 Group Amount By adding an acid to the solution, the —OH group becomes H 2 O, —O
As for the C 2 H 5 group, terminal —OH and —OC 2 H 5 were quantified by titration as C 2 H 5 OH.
【００２８】（３）スピンコート法 スピナー１Ｈ３６０型（協栄セミコンダクター製）を使
用し、塗布液数ミリリットルをシリコンウエハ基板上に
滴下し、１０００ｒｐｍ、５秒次いで４０００ｒｐｍ、
１５秒間回転し、塗布膜を形成した。(3) Spin coating method Using a spinner 1H360 type (manufactured by Kyoei Semiconductor), a few milliliters of a coating solution is dropped on a silicon wafer substrate, and then 1000 rpm, 5 seconds, and 4000 rpm.
It was rotated for 15 seconds to form a coating film.
【００２９】（４）膜厚の測定法 エリプソメーター（偏光解析装置）Ｌ−２Ｗ−１５Ｃ−
８３０（ガードナー社製）にてシリコン基板ウエハ上の
膜厚を測定した。(4) Method of measuring film thickness Ellipsometer (polarization analyzer) L-2W-15C-
830 (manufactured by Gardner) was used to measure the film thickness on the silicon substrate wafer.
【００３０】（５）塗膜物性の測定法 耐クラック性：６インチミラーウエハ上に膜厚１μ
ｍにて塗膜を形成し、５００℃、３０分熱処理したとき
のクラックの有無を見た。 脱ガス性：高真空中で５００℃まで加熱したときの
発生ガスの有無をマススペクトルメーターにより測定し
た。 収縮性：５００℃、３０分熱処理したときの膜厚変
化をエリプソメーターにより測定した。 吸湿性：塗膜を２８日間室温下に放置したときの吸
湿水分量をマススペクトル及びＴＧにより測定した。 平坦化特性：配線幅１．０以下〜数μｍ、配線間距
離１．０以下〜数μｍ、アスペクト比０．０１〜１０に
わたるさまざまなパターンを含むテストデバイスにコー
トしたときの断面走査電子顕微鏡により平坦化状態をみ
た（これのみテストデバイス使用）。(5) Method for measuring physical properties of coating film Crack resistance: 1 μm thick film on a 6-inch mirror wafer
m, a coating film was formed, and the presence or absence of cracks when heat-treated at 500 ° C. for 30 minutes was checked. Degassing property: The presence or absence of generated gas when heated to 500 ° C. in a high vacuum was measured by a mass spectrometer. Shrinkage: The change in film thickness after heat treatment at 500 ° C. for 30 minutes was measured by an ellipsometer. Hygroscopicity: The amount of moisture absorbed when the coating film was left at room temperature for 28 days was measured by mass spectrum and TG. Flattening characteristics: Cross section scanning electron microscope when coated on a test device containing various patterns ranging from wiring width 1.0 or less to several μm, wiring distance 1.0 or less to several μm, and aspect ratio 0.01 to 10 The flattened state was observed (only the test device was used).
【００３１】（６）液安定性：塗布液を５℃冷蔵庫、お
よび２０℃下に保管し、粘度及びスピンコート時の塗布
膜厚変化の有無を見た。(6) Solution stability: The coating solution was stored in a refrigerator at 5 ° C. and at 20 ° C., and the viscosity and the presence or absence of a change in the coating film thickness during spin coating were checked.
【００３２】（実施例１）前記一般式（Ｉ）においてＲ
1 がメチル基、Ｒ2 が水素とエチル基からなり、水酸基
含有量が１．４重量％、エトキシ基含有量が３．６重量
％、かつ両者のモル比が１：１で、数平均分子量ＭN が
２５００のラダー型シリコーンオリゴマー１３重量部を
エタノールとブタノールの混合溶剤（重量比１：１）８
７重量部に溶解して塗布液を得た。上記塗布液を６イン
チのベアシリコンウエハ上に膜厚４０００Åになるよう
にスピンコーティングし、１２０℃、１分、次いで、２
５０℃、２分のホットプレート処理を行った後、３５０
℃、３０分クリンオーブンにて加熱してキュアせしめ
た。キュア後、室温に冷却して諸物性を測定した。結果
を表１に示す。(Example 1) In the general formula (I), R
1 is a methyl group, R 2 is a hydrogen and an ethyl group, the hydroxyl group content is 1.4% by weight, the ethoxy group content is 3.6% by weight, and the molar ratio of both is 1: 1. 13 parts by weight of a ladder type silicone oligomer having MN of 2500 was mixed with a mixed solvent of ethanol and butanol (weight ratio 1: 1).
It was dissolved in 7 parts by weight to obtain a coating solution. The above coating solution was spin-coated on a 6-inch bare silicon wafer so as to have a film thickness of 4000 ° C., at 120 ° C. for 1 minute, and then
After performing a hot plate treatment at 50 ° C. for 2 minutes,
The mixture was heated in a clean oven at 30 ° C. for 30 minutes to cure. After curing, it was cooled to room temperature and various physical properties were measured. Table 1 shows the results.
【００３３】（実施例２） 前記一般式（Ｉ）においてＲ１ がメチル基９０モル
％、フェニル基１０モル％からなり、Ｒ２ が水素及び
エチル基であり、水酸基含有量が４．９重量％、エトキ
シ基含有量が６．６重量％、かつ両者のモル比が１：
０．５、数平均分子量ＭＮ が１３００のラダー型シリ
コーンオリゴマー１５重量部をエチレングリコールモノ
エチルエーテル８５重量部に溶解して塗布液を得た。上
記塗布液を実施例１と同様に６インチのベアシリコンウ
エハ上に膜厚４０００Åになるようコートし、キュア後
諸物性を測定した。結果を表１に示す。Example 2 In the general formula (I), R 1 is composed of 90 mol% of methyl group and 10 mol% of phenyl group, R 2 is hydrogen and ethyl group, and the content of hydroxyl group is 4.9% by weight. %, The ethoxy group content is 6.6% by weight, and the molar ratio of both is 1:
A coating liquid was obtained by dissolving 15 parts by weight of a ladder type silicone oligomer having a 0.5 and a number average molecular weight MN of 1300 in 85 parts by weight of ethylene glycol monoethyl ether. The coating solution was coated on a 6-inch bare silicon wafer to a film thickness of 4000 ° in the same manner as in Example 1, and after curing, various physical properties were measured. Table 1 shows the results.
【００３４】（実施例３） 前記一般式（Ｉ）においてＲ１ がメチル基、Ｒ２ が水
素とエチル基であり、水酸基含有量が０．３重量％、エ
トキシ基含有量が１４．２重量％、かつ両者のモル比が
１：１．８、数平均分子量ＭＮ が７２００のラダー型
シリコーンオリゴマー１３重量部をエタノールとブタノ
ールの混合溶剤（重量比１：１）８７重量部に溶解して
塗布液を得た。上記塗布液を実施例１と同様にコート
し、硬化後の諸物性を測定した。結果を表１に示す。Example 3 In the general formula (I), R 1 is a methyl group, R 2 is hydrogen and an ethyl group, the content of hydroxyl group is 0.3% by weight, and the content of ethoxy group is 14.2% by weight. 13 parts by weight of a ladder type silicone oligomer having a molar ratio of 1: 1.8 and a number average molecular weight MN of 7200 are dissolved in 87 parts by weight of a mixed solvent of ethanol and butanol (weight ratio 1: 1). A coating solution was obtained. The coating solution was coated in the same manner as in Example 1, and various physical properties after curing were measured. Table 1 shows the results.
【００３５】（比較例１）前記一般式（Ｉ）においてＲ
1 がメチル基、Ｒ2 が水素及びエチル基であり、水酸基
含有量が９．４重量％、エトキシ基含有量が２５重量
％、かつ両者のモル比が１：１で数平均分子量ＭN が４
００のラダー型シリコーンオリゴマー１３重量部をエタ
ノールとブタノールの混合溶剤（重量比１：１）８７重
量部に溶解して塗布液を得た。上記塗布液を実施例１と
同様にコートし、硬化後諸物性を測定した。結果を表１
に示す。(Comparative Example 1) In the general formula (I), R
1 is a methyl group, R 2 is a hydrogen and an ethyl group, the hydroxyl group content is 9.4% by weight, the ethoxy group content is 25% by weight, the molar ratio of both is 1: 1 and the number average molecular weight M N is 4
13 parts by weight of the ladder-type silicone oligomer No. 00 were dissolved in 87 parts by weight of a mixed solvent of ethanol and butanol (weight ratio: 1: 1) to obtain a coating liquid. The coating solution was coated in the same manner as in Example 1, and various physical properties after curing were measured. Table 1 shows the results
Shown in
【００３６】（比較例２）前記一般式（Ｉ）においてＲ
1 がメチル基、Ｒ2 が水素及びエチル基であり、水酸基
含有量が０．２重量％、エトキシ基含有量が０．６重量
％、かつ両者のモル比が１：１で数平均分子量が１４０
００のラダー型シリコーンオリゴマー１３重量部をエタ
ノールとブタノールの混合溶剤（重量比１：１）８７重
量部に溶解して塗布液を得た。上記塗布液を実施例１と
同様にコートし、硬化後諸物性を測定した。結果を表１
に示す。Comparative Example 2 In the above general formula (I), R
1 is a methyl group, R 2 is a hydrogen and an ethyl group, the hydroxyl group content is 0.2% by weight, the ethoxy group content is 0.6% by weight, the molar ratio of both is 1: 1 and the number average molecular weight is 140
13 parts by weight of the ladder-type silicone oligomer No. 00 were dissolved in 87 parts by weight of a mixed solvent of ethanol and butanol (weight ratio 1: 1) to obtain a coating solution. The coating solution was coated in the same manner as in Example 1, and various physical properties after curing were measured. Table 1 shows the results
Shown in
【００３７】（比較例３）前記一般式（Ｉ）においてＲ
1 がメチル基、Ｒ2 が水素及びエチル基であり、水酸基
含有量が３．９重量％、エトキシ基含有量が１．０重量
％、かつ両者のモル比が１：０．１で、数平均分子量が
２４００のラダー型シリコーンオリゴマー１３重量部を
エタノールとブタノールの混合溶剤（重量比１：１）８
７重量部に溶解して塗布液を得た。上記塗布液を実施例
１と同様にコートし、硬化後諸物性を測定した。結果を
表１に示す。Comparative Example 3 In the above general formula (I), R
1 is a methyl group, R 2 is a hydrogen and an ethyl group, the hydroxyl group content is 3.9% by weight, the ethoxy group content is 1.0% by weight, and the molar ratio of both is 1: 0.1. 13 parts by weight of a ladder type silicone oligomer having an average molecular weight of 2400 was mixed with a mixed solvent of ethanol and butanol (weight ratio 1: 1).
It was dissolved in 7 parts by weight to obtain a coating solution. The coating solution was coated in the same manner as in Example 1, and various physical properties after curing were measured. Table 1 shows the results.
【００３８】（比較例４）前記一般式（Ｉ）においてＲ
1 がメチル基、Ｒ2 が水素及びエチル基であり、水酸基
含有量が０．６重量％、エトキシ基含有量が４．３重量
％、かつ両者のモル比が１：２．５で、数平均分子量が
２８００のラダー型シリコーンオリゴマー１３重量部を
エタノールとブタノールの混合溶剤（重量比１：１）８
７重量部に溶解して塗布液を得た。上記塗布液を実施例
１と同様にコートし、硬化後諸物性を測定した。結果を
表１に示す。Comparative Example 4 In the above general formula (I), R
1 is a methyl group, R 2 is a hydrogen and an ethyl group, the hydroxyl group content is 0.6% by weight, the ethoxy group content is 4.3% by weight, and the molar ratio of both is 1: 2.5. 13 parts by weight of a ladder type silicone oligomer having an average molecular weight of 2800 was mixed with a mixed solvent of ethanol and butanol (weight ratio 1: 1) 8
It was dissolved in 7 parts by weight to obtain a coating solution. The coating solution was coated in the same manner as in Example 1, and various physical properties after curing were measured. Table 1 shows the results.
【００３９】（比較例５）メチルトリヒドロキシシラン
１４重量部をメタノール８６重量部中に溶解した塗布液
を用いて実施例１と同様にコートし４００℃にて硬化後
諸物性を測定した。結果を表１に示す。Comparative Example 5 A coating solution prepared by dissolving 14 parts by weight of methyltrihydroxysilane in 86 parts by weight of methanol was coated in the same manner as in Example 1 and cured at 400 ° C. to measure various physical properties. Table 1 shows the results.
【００４０】（比較例６）テトラヒドロキシシラン６重
量部をエタノールと酢酸エチルの混合溶剤（重量比８：
２）９４重量部に溶解した塗布液を実施例１と同様に膜
厚２０００Åコートし、４００℃にて硬化後諸物性を測
定した。結果を表１に示す。Comparative Example 6 6 parts by weight of tetrahydroxysilane was mixed with a mixed solvent of ethanol and ethyl acetate (weight ratio: 8:
2) A coating solution dissolved in 94 parts by weight was coated in a thickness of 2000 ° in the same manner as in Example 1, and after curing at 400 ° C., various physical properties were measured. Table 1 shows the results.
【００４１】[0041]
【表１】 [Table 1]
【００４２】[0042]
【発明の効果】本発明の有機ＳＯＧにおいては、末端基
の縮合反応性が従来のものに比較して大幅に改良されて
おり、また分子量も従来に比較してオリゴマーからポリ
マー領域のものを採用している。According to the organic SOG of the present invention, the condensation reactivity of the terminal group is significantly improved as compared with the conventional one, and the molecular weight of the organic SOG is in the range from oligomer to polymer as compared with the conventional one. are doing.
【００４３】このため液の保存安定性は良好である一
方、加熱硬化時の温度も比較的低い温度で行うことがで
き、またこのときの硬化収縮も従来知られている有機Ｓ
ＯＧよりずっと小さい。For this reason, while the storage stability of the liquid is good, the temperature at the time of heat curing can be performed at a relatively low temperature, and the curing shrinkage at this time is also known in organic S.
Much smaller than OG.
【００４４】またポリオルガノシルセスキオキサンの硬
化反応の完結度が高く、高温加熱時における収縮も小さ
く、かつ発生ガスが少なくて済み、また硬化膜の吸湿性
も低い。The degree of completion of the curing reaction of the polyorganosilsesquioxane is high, the shrinkage upon heating at high temperature is small, the amount of generated gas is small, and the moisture absorption of the cured film is low.
【００４５】本発明の有機ＳＯＧは平坦化能力、絶縁性
にも優れており、上述の特性と合わせて半導体用絶縁
膜、平坦化膜として適している。The organic SOG of the present invention has excellent flattening ability and insulating properties, and is suitable as an insulating film for semiconductors and a flattening film in combination with the above-mentioned characteristics.
【００４６】また本発明の有機ＳＯＧは金属、セラミッ
クス、プラスチックスなどの多様な基材表面にコーティ
ングし、特徴ある表面特性を付与するために用いること
もできる。The organic SOG of the present invention can also be used to coat various substrates such as metals, ceramics and plastics to impart characteristic surface characteristics.
フロントページの続き (56)参考文献 特開 昭56−49540（ＪＰ，Ａ) 特開 昭57−160132（ＪＰ，Ａ) 特開 平２−277255（ＪＰ，Ａ) 特開 昭60−108842（ＪＰ，Ａ) 特開 平４−104253（ＪＰ，Ａ) 特開 平４−63883（ＪＰ，Ａ) 特開 昭63−120774（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) H01L 21/316 Continuation of the front page (56) References JP-A-56-49540 (JP, A) JP-A-57-160132 (JP, A) JP-A-2-277255 (JP, A) JP-A-60-108842 (JP) JP-A-4-104253 (JP, A) JP-A-4-63883 (JP, A) JP-A-63-120774 (JP, A) (58) Fields studied (Int. Cl. 7 , DB (Name) H01L 21/316
Claims (3)
５００〜１０，０００であり、末端基として水酸基を
０．３〜６重量％と、アルコキシ基を０．９〜１６重量
％、かつ両者のモル比が１：０．２〜２．０の範囲に含
有しているポリオルガノシルセスキオキサンを加熱キュ
アしたことを特徴とする半導体用絶縁膜または平坦化
膜。 【化１】 （一般式（Ｉ）においてＲ1 はメチル基またはフェニル
基、Ｒ2 は炭素数１〜３のアルキル基または水素原子を
示し、ｎは分子量に対応する正の数であり、分散を伴う
集合体を示す。）1. A compound represented by the formula (I) having a number average molecular weight of 500 to 10,000, a hydroxyl group as a terminal group of 0.3 to 6% by weight, an alkoxy group of 0.9 to 16% by weight, And a polyorganosilsesquioxane containing a molar ratio of 1: 0.2 to 2.0 and cured by heating. Embedded image (In the general formula (I), R 1 represents a methyl group or a phenyl group; R 2 represents an alkyl group having 1 to 3 carbon atoms or a hydrogen atom; n is a positive number corresponding to the molecular weight; Is shown.)
またはフェニル基であり、全体としてのメチル基含有量
が８０モル％以上である請求項１記載の半導体用絶縁膜
または平坦化膜。2. In the general formula (I), R 1 is a methyl group or a phenyl group, and the total methyl group content is 80 mol% or more. .
ルセスキオキサンを有機溶剤に溶解し、デバイス基板の
配線上にコーティングし、加熱キュアすることを特徴と
する請求項１記載の半導体絶縁膜または平坦化膜を形成
する方法。3. The semiconductor insulation according to claim 1, wherein the polyorganosilsesquioxane represented by the general formula (I) is dissolved in an organic solvent, coated on the wiring of the device substrate, and cured by heating. A method for forming a film or a planarizing film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3235388A JP2997105B2 (en) | 1991-08-21 | 1991-08-21 | Insulating films for semiconductors and methods for forming them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3235388A JP2997105B2 (en) | 1991-08-21 | 1991-08-21 | Insulating films for semiconductors and methods for forming them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0555201A JPH0555201A (en) | 1993-03-05 |
| JP2997105B2 true JP2997105B2 (en) | 2000-01-11 |
Family
ID=16985346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3235388A Expired - Fee Related JP2997105B2 (en) | 1991-08-21 | 1991-08-21 | Insulating films for semiconductors and methods for forming them |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2997105B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000063142A (en) | 2000-02-17 | 2000-11-06 | 이응찬 | Starting materials for manufacturing polyorganosilsesquioxanes, polyorganosilsesquioxanes and method for manufacturing polyorganosilsesquioxanes |
| CN109111151B (en) * | 2018-09-12 | 2021-01-08 | 中国建材检验认证集团厦门宏业有限公司 | Cement self-leveling agent and preparation method thereof |
-
1991
- 1991-08-21 JP JP3235388A patent/JP2997105B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0555201A (en) | 1993-03-05 |
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