KR20050040244A - Organoruthenium compounds for cvd - Google Patents

Organoruthenium compounds for cvd Download PDF

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KR20050040244A
KR20050040244A KR1020030075396A KR20030075396A KR20050040244A KR 20050040244 A KR20050040244 A KR 20050040244A KR 1020030075396 A KR1020030075396 A KR 1020030075396A KR 20030075396 A KR20030075396 A KR 20030075396A KR 20050040244 A KR20050040244 A KR 20050040244A
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ruthenium
thin film
cvd
present
compound
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오카모토코지
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다나까 기낀조꾸 고교 가부시끼가이샤
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00Metallocenes
    • C07F17/02Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23CCOATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/06Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material
    • C23C16/18Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material from metallo-organic compounds
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23CCOATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40Oxides

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Abstract

본 발명은, 박막으로서의 막 형성속도가 균일하고, 열적 안정성이 우수하며, 형태성(morphology)이 양호한 박(箔)을 제조하는 것이 가능한 유기 루테늄 화합물에 관한 것이다. 본 발명의 유기 루테늄 화합물은, 루테노센의 2개의 시클로펜타디엔환의 어느 하나에 치환기로서 프로필기(CH2CH2CH3) 또는 n-부틸기(CH 2CH2CH2CH3)가 치환된 유기금속화합물이다.The present invention relates to an organic ruthenium compound capable of producing a thin film having a uniform film formation rate as a thin film, excellent thermal stability and good morphology. In the organic ruthenium compound of the present invention, a propyl group (CH 2 CH 2 CH 3 ) or an n-butyl group (CH 2 CH 2 CH 2 CH 3 ) is substituted with one of two cyclopentadiene rings of ruthenocene. It is an organometallic compound.

Description

CVD용의 유기 루테늄 화합물 {ORGANORUTHENIUM COMPOUNDS FOR CVD}Organic ruthenium compound for COD {ORGANORUTHENIUM COMPOUNDS FOR CVD}

본 발명은, CVD법에 따라 기판 표면에 루테늄, 루테늄 산화물의 박막을 형성하기 위한 유기금속화합물에 관한 것이다. 특히 반도체 장치나 부품의 전극재료 등의 제조에 대하여 유용한 유기금속화합물에 관한 것이다.The present invention relates to an organometallic compound for forming a thin film of ruthenium and ruthenium oxide on the surface of a substrate by the CVD method. In particular, the present invention relates to organometallic compounds useful for the production of electrode materials for semiconductor devices and components.

반도체장치의 전극재료 등 최첨단 기술분야에서는 종래부터 유기 루테늄 화합물이, CVD 법에 따라 각종의 루테늄 박막을 형성하기 위하여 사용되고 있다. 이 때, 루테늄 박막을 형성하기 위해서는, 식 4에 나타낸 루테노센이라고 하는 유기 루테늄 화합물이 원료로 사용되고 있다.Background Art In the state of the art such as electrode materials for semiconductor devices, organic ruthenium compounds have conventionally been used to form various ruthenium thin films by the CVD method. At this time, in order to form a ruthenium thin film, the organic ruthenium compound called ruthenocene shown in Formula 4 is used as a raw material.

(식 4)(Equation 4)

식 4에 나타낸 유기 루테늄 화합물은, 각각의 시클로펜타디엔환인 오원환(五員環)을 구성하는 것은 탄소와 수소만이고, 2개의 오원환의 사이에 루테늄 원자가 끼워진 샌드위치 구조를 가지는 것이다.The organic ruthenium compound shown in Formula 4 has only the carbon and hydrogen which comprise the five-membered ring which is each cyclopentadiene ring, and has a sandwich structure in which a ruthenium atom was sandwiched between two five-membered rings.

그러나, 식 4에 나타난 유기 루테늄 화합물은, 융점이 198℃로 높고, 증기압도 낮기 때문에, 기화속도의 제어가 곤란하다는 결점을 가지고 있다. 기화속도의 제어가 곤란하다고 하는 것은, 박막으로서의 막 형성속도가 불균일하게 되고, 막두께의 정밀도 및 평면성이 부족한 제품이 생산된다는 것을 의미하고 있다. 더우기 식 4에 나타난 유기 루테늄 화합물은, 기화시키기 위해 가열할 때, 열분해 반응을 일으키는 일이 있고, 열적 안정성이 부족하다는 문제도 제조현장에서 지적되고 있다. However, the organic ruthenium compound shown in Formula 4 has a disadvantage that it is difficult to control the vaporization rate because the melting point is high at 198 ° C. and the vapor pressure is low. The difficulty in controlling the vaporization rate means that the film formation speed as a thin film becomes uneven, and that a product lacking the precision and flatness of the film thickness is produced. Moreover, the organic ruthenium compound shown in Formula 4 may cause a thermal decomposition reaction when it heats to vaporize, and the problem that the thermal stability is lacking has also been pointed out at the manufacturing site.

그런 까닭으로, 증기압이 높고, 기화속도의 제어가 용이하며, 또한 열적 안정성이 우수한 원료물질로서, 식 5에 나타낸 비스(에틸시클로펜타디에닐)루테늄의 사용이 최근 검토되고 있다. 이 비스(에틸시클로펜타디에닐)루테늄은, 비스(시클로펜타디에닐)루테늄(이하, 루테노센이라는 통칭을 사용한다)의 2개의 시클로펜타디엔환의 수소를 에틸기로 치환한 것이며, 루테노센보다 기화온도, 분해온도가 낮다는 점때문에, CVD공정에 있어서 취급이 용이하다는 잇점이 있다. 또, 비스(에틸시클로펜타디에닐)루테늄은, 불활성가스중에서의 안정성이 높고, 독성도 없다는 점도, CVD원료로서 적격이라고 할 것이다. For this reason, the use of bis (ethylcyclopentadienyl) ruthenium shown in Formula 5 has recently been studied as a raw material having high vapor pressure, easy control of the vaporization rate, and excellent thermal stability. The bis (ethylcyclopentadienyl) ruthenium is obtained by substituting two cyclopentadiene rings of bis (cyclopentadienyl) ruthenium (hereinafter referred to as ruthenocene) with an ethyl group, and vaporizing it than ruthenocene. Due to the low temperature and decomposition temperature, there is an advantage in that the handling is easy in the CVD process. In addition, bis (ethylcyclopentadienyl) ruthenium has high stability in inert gas and no toxicity, and is suitable as a CVD raw material.

(식 5)(Eq. 5)

그러나, 박막전극에 대하여는 전기특성이 우수하다는 것이 당연히 요구되지만, 여기에 더하여 표면이 매끈하고 그 형태(morphology)가 양호하며, 더우기, 단차피복능(step coverage)이 양호한 것이 강하게 요구되고 있다.However, although it is naturally required for the thin film electrode to have excellent electrical characteristics, it is strongly required to have a smooth surface, a good morphology, and further, a good step coverage.

그러나, 비스(에틸시클로펜타디에닐)루테늄을 원료로 하여 루테늄막을 제조하면, 형태성(morphology)이 나쁜 박막이 제조되는 경우가 있고, 균일하고, 치밀한 박막을 얻을 수 없는 일도 있다. However, when a ruthenium film is manufactured using bis (ethylcyclopentadienyl) ruthenium as a raw material, a thin film with poor morphology may be produced, and a uniform and dense thin film may not be obtained.

또한 비스(에틸시클로펜타디에닐)루테늄은, 불활성가스중에서의 안정성은 양호하지만, 공기중에서의 안정성이 좋지 않다는 문제가 있다. 이러한 점은, 박막의 제조공정에 있어서 원료물질의 취급을 곤란하게 하는 문제이다. In addition, bis (ethylcyclopentadienyl) ruthenium has a problem that stability in inert gas is good, but stability in air is not good. This is a problem that makes it difficult to handle raw materials in the manufacturing process of a thin film.

본 발명은 이상과 같은 배경하에서 이루어진 것으로서, 기화속도가 높고, 형태성(morphology)이 양호한 루테늄 박막을 제조할 수 있으며, 또한 공기중에서의 안정성이 우수한 루테늄 화합물을 제공하는 것을 목적으로 한다. The present invention has been made under the above-described background, and an object of the present invention is to provide a ruthenium thin film having high vaporization rate, good morphology, and excellent stability in air.

본 발명은 CVD법에 의하여 기판 표면에 루테늄 또는 루테늄 산화물의 박막을 형성하기 위한 유기금속화합물에 있어서, 하기 식 1의 일반구조식을 가지는 것을 특징으로 하는 유기금속화합물에 관한 것이다.  The present invention relates to an organometallic compound characterized by having a general structural formula of the following formula 1 in the organometallic compound for forming a thin film of ruthenium or ruthenium oxide on the surface of the substrate by CVD.

(식 1)(Equation 1)

[상기 일반구조식 중, 치환기 R1은 프로필기(CH2CH2CH3) 또는 n-부틸기(CH2CH2CH2CH3)이다.][In the general structural formula, the substituent R 1 is a propyl group (CH 2 CH 2 CH 3 ) or n-butyl group (CH 2 CH 2 CH 2 CH 3 ).]

본 발명에 있어서, 제1의 루테늄 화합물은, CVD법에 의하여 기판 표면에 루테늄 혹은 루테늄 산화물의 박막을 형성하기 위한 유기금속 화합물로서, 2개의 시클로펜타디엔환의 어느 하나에 치환기로서 프로필기(CH2CH2CH3)가 치환된, 식 2에 나타낸 일반구조식을 가지는 유기금속화합물이다.In the present invention, the first ruthenium compound is an organometallic compound for forming a thin film of ruthenium or ruthenium oxide on the surface of a substrate by a CVD method, and a propyl group (CH 2) as a substituent on one of two cyclopentadiene rings. CH 2 CH 3 ) is an organometallic compound having the general structural formula represented by Formula 2.

(식 2)(Equation 2)

또한 본 발명에 있어서, 제2의 루테늄 화합물은, CVD법에 의하여 기판 표면에 루테늄 혹은 루테늄 산화물의 박막을 형성하기 위한 유기금속 화합물로서, 2개의 시클로펜타디엔환의 어느 하나에 치환기로서 n-부틸기(CH2CH2CH2CH 3)가 치환된, 식 3에 나타낸 일반구조식을 가지는 유기금속화합물이다.In the present invention, the second ruthenium compound is an organometallic compound for forming a thin film of ruthenium or ruthenium oxide on the surface of a substrate by CVD, and has an n-butyl group as a substituent on one of two cyclopentadiene rings. An organometallic compound having the general structural formula shown in Formula 3 wherein (CH 2 CH 2 CH 2 CH 3 ) is substituted.

(식 3)(Equation 3)

본 발명에 있어서의 2가지의 루테늄 화합물은, 비스(에틸시클로펜타디에닐)루테늄과 같이, 입체장해가 큰 알킬기를 시클로펜타디엔환상에 가지기 때문에, 다른 반응원소가 루테늄의 위치에 접근하기 어렵고, 종래의 식 4에 나타낸 유기루테늄화합물에 비하여, 금속루테늄으로의 분해, 산화물 등으로의 분해반응이 일어나기 어렵게 된다. 이 점은 본 발명에 있어서의 유기금속화합물이, CVD용 화합물원료로서 안정된 기화성과 열안정성을 나타내는 요인이 된다. 그리고 본 발명과 같이 치환기를 하나로 하므로써, 불활성가스중 뿐만 아니라, 공기중에 있어서의 안정성도 확보된다.Since the two ruthenium compounds in the present invention have an alkyl group having a high steric hindrance on the cyclopentadiene ring like bis (ethylcyclopentadienyl) ruthenium, other reaction elements are difficult to access the position of ruthenium, Compared with the organic ruthenium compound shown in the conventional formula 4, decomposition to metal ruthenium, decomposition reaction to oxide, etc. are less likely to occur. This is a factor in which the organometallic compound in the present invention exhibits stable vaporization and thermal stability as a compound raw material for CVD. By using one substituent as in the present invention, not only inert gas but also stability in air is ensured.

그리고, 본원에 있어서의 2가지의 유기금속 화합물은, 안정성에 있어서 종래의 유기화합물보다도 더욱 우수하며, 표면 조도(粗度- 거칠기)가 양호하고 바람직한 형태성(morphology)을 가지는 박막이 제조가능하다.The two organometallic compounds in the present application are more excellent in stability than the conventional organic compounds in terms of stability, and a thin film having good surface roughness and favorable morphology can be produced. .

그러면서도, 본 발명에서 선택한 치환기는 특이한 구성원소를 함유하지 않는다. 따라서, 형성된 박막에도 불순물량이 증가하는 일도 없고, 특히 루테늄박막에 있어서는, 연구한 범위내에서는, 극히 고순도의 박막을 제조할 수 있었다. Nevertheless, the substituents selected in the present invention do not contain specific member elements. Therefore, the amount of impurities does not increase in the formed thin film, and especially in the ruthenium thin film, an extremely high purity thin film can be produced within the range studied.

(실시예)(Example)

이하, 본 발명에 관한 유기 루테늄 화합물의 최선이라고 생각되는 실시의 형태에 대하여 설명하는데, 본 발명은 이러한 실시예에 한정되는 것은 아니다.EMBODIMENT OF THE INVENTION Hereinafter, although embodiment considered to be the best of the organic ruthenium compound which concerns on this invention is described, this invention is not limited to this Example.

제1실시형태 : [프로필시클로펜타디에닐][시클로펜타디에닐]루테노센의 제조 First Embodiment Preparation of [Propylcyclopentadienyl] [cyclopentadienyl] ruthenocene

루테노센 1000g과 무수락산(butyric acid anhydrous) 3400g을 혼합하고, 85% 인산 500g을 더 가하여 반응시키고, 반응액에 10% 수산화나트륨 500g을 가하여 중화시킨 후, 초산에틸로 추출조작을 하였다.1000 g of lutenocene and 3400 g of butyric acid anhydrous were mixed, 500 g of 85% phosphoric acid was added to the reaction, and the reaction solution was neutralized by adding 500 g of 10% sodium hydroxide, followed by extraction with ethyl acetate.

추출물에 백금/카본촉매 500g, 에탄올 4000mL를 가하여 110℃, 90㎏/㎠의 조건에서 5시간 반응시켜, 촉매를 여과제거하고, 또한 용매를 유거(留去)시켜, [프로필시클로펜타디에닐][시클로펜타디에닐]루테노센을 590g 제조하였다. 500 g of platinum / carbon catalyst and 4000 mL of ethanol were added to the extract, and the mixture was reacted at 110 ° C. and 90 kg / cm 2 for 5 hours. The catalyst was filtered off, and the solvent was distilled off to obtain [propylcyclopentadienyl]. 590 g of [cyclopentadienyl] luthenocene was produced.

제2실시형태 : [n-부틸시클로펜타디에닐][시클로펜타디에닐]루테노센의 제조 Second Embodiment Preparation of [n-butylcyclopentadienyl] [cyclopentadienyl] ruthenocene

루테노센 1000g과 무수프로피온산 3400g을 혼합하고, 85% 인산 500g을 더 가하여 반응시키고, 반응액에 10% 수산화나트륨 500g을 가하여 중화시킨 후, 초산에틸로 추출조작을 하였다.1000 g of ruthenocene and 3400 g of propionic anhydride were mixed, 500 g of 85% phosphoric acid was further added to react, and the reaction solution was neutralized with 500 g of 10% sodium hydroxide, followed by extraction with ethyl acetate.

추출물에 백금/카본촉매 500g, 에탄올 4000mL를 가하여 110℃, 90㎏/㎠의 조건에서 5시간 반응시켜, 촉매를 여과제거하고, 또한 용매를 유거시켜, [n-부틸시클로펜타디에닐][시클로펜타디에닐]루테노센을 600g 제조하였다. 500 g of platinum / carbon catalyst and 4000 mL of ethanol were added to the extract, and the mixture was allowed to react for 5 hours at 110 ° C. and 90 kg / cm 2. The catalyst was filtered off, and the solvent was distilled off. [N-butylcyclopentadienyl] [cyclo 600 g of pentadienyl] ruthenocene was prepared.

이상으로 제조된 2가지의 유기금속화합물의 물성을 조사하였다. 그 결과를 표 1에 나타내었다. 그 조사는, 종래의 CVD용 유기금속화합물인 디에틸루테노센에 대하여도 행하였다. The physical properties of the two organometallic compounds prepared above were investigated. The results are shown in Table 1. The investigation was also carried out for diethylruthenocene, which is a conventional organometallic compound for CVD.

표 1Table 1

다음으로, 이들 3가지의 유기금속화합물을 이용하여 CVD법에 따라 박막을 제조하고, 그 표면 조도를 측정, 비교하였다. 박막의 제조조건은 이하와 같다. 박막의 제조는 3매의 기판에 대하여 행하였다. Next, using these three organometallic compounds, a thin film was produced by the CVD method, and the surface roughness thereof was measured and compared. The manufacturing conditions of a thin film are as follows. The thin film was produced for three substrates.

기판온도 250℃Substrate temperature 250 ℃

쳄버 압력 650PaChamber pressure 650Pa

캐리어가스 유량 200sccmCarrier Gas Flow Rate 200sccm

반응가스유량 200sccmReaction gas flow rate 200 sccm

그리고, 제조된 3매의 박막의 표면 조도를, AFM(Atomic Force Microscope, 원자간력현미경)으로 측정하였다. 그 결과를 표 2에 나타내었다.The surface roughnesses of the three thin films thus produced were measured by AFM (Atomic Force Microscope, Atomic Force Microscope). The results are shown in Table 2.

표 2TABLE 2

이상의 실시결과로부터, 우선, 본원에 있어서의 2가지의 유기화합물은 공기중에서의 안정성이 우수하고, 종래의 디에틸루테노센이 분해를 일으키는 것을 고려하면, 안정성이 높은 것으로 확인되었다. From the above results, first, it was confirmed that the two organic compounds in the present application were excellent in stability in the air, and considering that the conventional diethylruthenocene caused decomposition, the stability was high.

또한, 이들에 따른 박막제조시험에 대하여, 본원에 있어서의 2가지의 유기화합물에 의하여 제조된 박막은, 표면 조도가 2RMS전후이다. 이에 대하여, 종래의 디에틸루테노센에 의하여 제조된 박막의 표면 조도는, 3.3~4.2RMS이며 본원에 있어서의 유기화합물에 의하여 제조된 박막의 1.5 ~ 2배의 조도를 가진다. 따라서 종래의 디에틸루테노센으로부터 제조된 박막의 표면 조도로는, 앞으로 더욱 집적도가 증가하는 전자디바이스의 박막으로서는 부적절하다.In addition, regarding the thin film manufacturing test according to these, the surface roughness of the thin film manufactured by the two organic compounds in this application is around 2RMS. On the other hand, the surface roughness of the thin film manufactured by the conventional diethyl luthenocene is 3.3-4.2RMS, and has 1.5-2 times roughness of the thin film manufactured by the organic compound in this application. Therefore, the surface roughness of the thin film prepared from the conventional diethyl luthenocene is not suitable as the thin film of the electronic device which further increases the degree of integration in the future.

이와 같이, 본원에 있어서의 2가지의 유기화합물은 CVD용의 유기금속 화합물로서 매우 적합하다는 것이 확인되었다.Thus, it was confirmed that the two organic compounds in this application are very suitable as organometallic compounds for CVD.

Claims (1)

CVD법에 의하여 기판 표면에 루테늄 또는 루테늄 산화물의 박막을 형성하기 위한 유기금속화합물에 있어서, 하기 식 1의 일반구조식을 가지는 것을 특징으로 하는 유기금속화합물. An organometallic compound for forming a ruthenium or ruthenium oxide thin film on the surface of a substrate by CVD, the organometallic compound characterized by having the general formula of the following formula (1). (식 1)(Equation 1) [상기 일반구조식 중, 치환기 R1은 프로필기(CH2CH2CH3) 또는 n-부틸기(CH2CH2CH2CH3)이다.][In the general structural formula, the substituent R 1 is a propyl group (CH 2 CH 2 CH 3 ) or n-butyl group (CH 2 CH 2 CH 2 CH 3 ).]
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