EP1102872A1 - Nouveaux precurseurs organo-cuivreux destines au depot chimique en phase vapeur d'un film de cuivre - Google Patents
Nouveaux precurseurs organo-cuivreux destines au depot chimique en phase vapeur d'un film de cuivreInfo
- Publication number
- EP1102872A1 EP1102872A1 EP99959960A EP99959960A EP1102872A1 EP 1102872 A1 EP1102872 A1 EP 1102872A1 EP 99959960 A EP99959960 A EP 99959960A EP 99959960 A EP99959960 A EP 99959960A EP 1102872 A1 EP1102872 A1 EP 1102872A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- copper film
- organocuprous
- precursors
- hfac
- compound
- 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.)
- Withdrawn
Links
- 239000010949 copper Substances 0.000 title claims abstract description 42
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 21
- 239000002243 precursor Substances 0.000 title description 28
- 238000005229 chemical vapour deposition Methods 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011737 fluorine Chemical group 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims description 16
- 238000000151 deposition Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000008016 vaporization Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000010408 film Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 3
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- AASUFOVSZUIILF-UHFFFAOYSA-N diphenylmethanone;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AASUFOVSZUIILF-UHFFFAOYSA-N 0.000 description 2
- -1 e.g. Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 239000012691 Cu precursor Substances 0.000 description 1
- 229910004166 TaN Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING 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
- C23C—COATING 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
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/06—Chemical 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
- C23C16/18—Chemical 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
-
- C—CHEMISTRY; METALLURGY
- C23—COATING 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
- C23C—COATING 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
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/31—Coating with metals
- C23C18/38—Coating with copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
Definitions
- the present invention relates to novel organocuprous precursors which are useful in the chemical vapor deposition of a copper film having high purity; and to a process for the preparation of a copper film using same.
- a metallic interconnect is typically formed by a chemical vapor deposition (CVD) method using a metallorganic precursor compound, and Cu films have previously been prepared using various organic copper (II) precursors such as Cu(II) (hfac) 2 , wherein hfac stands for hexafluoroacetyl- acetonate.
- II organic copper
- a CVD process using such Cu(II) precursors requires a high deposition temperature and the resulting Cu film is often contaminated by various impurities .
- Organic copper (I) precursor compounds usable in a low- temperature, selective CVD process have been recently described.
- organocuprous precursors such as (hfac) Cu(I) (VTMS) (VTMS : vinyltrimethylsilane) and (hfac) Cu (I) (ATMS) (ATMS : allyltrimethylsilane) in a low- temperature CVD process to selectively deposit a Cu film on a conductive substrate surface
- VTMS VTMS : vinyltrimethylsilane
- ATMS ATMS
- U.S. Patent No. 5,098,516 teaches the use of Cu(I)- olefin precursors such as (hfac) Cu (I) ⁇ COD (COD: cyclooctadiene) and (hfac) Cu (I) • NBD (NBD: norbonadiene) in a low temperature CVD process.
- Cu(I) -olefin precursors are solids, and they must be sublimed at a temperature below their thermal decomposition temperatures, e.g., about 105 °C for (hfac) Cu (I) • COD .
- 5,098,516 is hampered by the difficulty in handling solid precursors in a mass production system. Moreover, the CVD of a copper film using, e.g., (hfac) Cu (I) • COD requires a relatively high substrate temperature of above 150 °C and the resulting copper film is often of poor quality.
- an organic copper (I) precursor which can be advantageously used in a low-temperature CVD process for the mass production of a contaminant -free copper film.
- R. , R 2 and R 3 are each independently a C,_ 8 alkyl, C,,_ 8 alkoxy, aryl or aryloxy group,
- R, and R 5 are each independently hydrogen, fluorine, a C n F 2n+1 or C H 2 +1 group, n being an integer in the range of 1 to 6,
- a process for depositing a copper film on a substrate which comprises vaporizing the compound of formula (I) and bringing the resulting vapor into contact with the substrate.
- Fig. 1 depicts the thermal decomposition characteristics of the inventive organocuprous precursor ( (hfac) Cu(DMB) ) , as analyzed by TGA (thermal gravimetric analyzer) and DSC (differential scanning calorimeter) _
- Fig. 2 exhibits the thermal decomposition characteristics of (hfac) Cu (VTMS) , as analyzed by TGA and
- FIG. 3 shows the vapor pressure changes of the inventive organocuprous precursor ( (hfac) Cu (DMB) ) and
- Fig. 4 illustrates the copper film deposition rate as function of the substrate temperature in a CVD process using the inventive organocuprous precursor ( (hfac) Cu (DMB) ) , (hfac) C (VTMS) and (hfac) Cu (ATMS) ; and
- Fig. 5 presents the change in the specific resistance of the copper film derived from the inventive precursor ( (hfac) Cu (DMB) ) with the substrate temperature.
- R 1 , R 2 and R 3 are each independently methyl, ethyl, methoxy or ethoxy group
- R 4 and R 5 are each dependently a C n F 2n+1 or C n H 2n+1 group wherein n is 1 or 4
- R 6 is hydrogen
- More preferred compounds of formula (I) according to the present invention are those represented by formula (I -a) and (I-b) :
- R and R 5 are each dependently a C n F 2n+1 or C n H 2n+1 group (n is an integer of 1 to 4), ' preferably trifluoromethyl group .
- the compound of formula (I -a) may be prepared by reacting 1, 1, 1, 5, 5, 5-hexafluoro-2,4-pentanedione (Hhfac) , 3,3- dimethyl-1-butene (DMB) and cuprous oxide (Cu 2 0) in the presence of an organic solvent, e.g., diethylether or dichloromethane, at a temperature ranging from 0 to 20 °C under an ambient pressure for 2 to 3 hours.
- the reactants may be preferably employed in an Hhfac : DMB : Cu 2 0 molar ratio of about 2 : 2 : 1.
- the compound of formula (I-b) wherein R 4 and R 5 are each a trifluoromethyl group may be prepared by using 3 , 3-dimethyl -1-butyne (i .e . , tert-butylacetylene) (TBA) in place of 3 , 3 -dimethyl -1-butene (DMB) , in the process for the synthesis of the compound of formula (I-a) .
- TSA 3-dimethyl -1-butyne
- DMB 3 -dimethyl -1-butene
- the compound of formula (I) according to the present invention has good thermostability and high volatility, and in a CVD process for the formation of a copper film on a specified surface of a substrate, it may be conveniently vaporized in a bubbler or evaporator at a temperature ranging from about 15 to 100 °C in a gas delivering system or a liquid delivery system.
- the CVD process for the formation of a copper thin film using the inventive organocuprous precursor may be carried out in a conventional manner, e.g., by vaporizing the inventive precursor and conveying the resulting vapor with a carrier gas such as argon to a substrate, e.g., platinum, silica, TiN, TaN, WN, etc., which is preferably heated to a temperature ranging from 100 to 300 °C, more preferably from 150 to 250 °C, under a reduced pressure, e.g., 0.1 to 10 torr .
- a carrier gas such as argon
- the thickness of the copper film may be conveniently controlled by adjusting the deposition time.
- the copper film obtained according to the present invention is useful as a metallized or seed layer of a semiconductor device.
- the resulting reddish suspension was stirred for 1 hour and cooled to 0 °C, and slowly added thereto with a canula was a solution of 1.46 g (7.0 mmol) of 1 , 1 , 1 , 5 , 5 , 5-hexafluoro- 2, 4-pentanedione (Hhfac) in diethyl ether.
- the resulting mixture was stirred at room temperature for 2 hours and, at this time, the color of the mixture turned yellow.
- the resulting solution was filtered through a bed of CELLITETM and the solvent was removed therefrom under a reduced pressure to obtain 1.75 g of the titled compound as a yellow solid (yield 73 %) .
- Figs. 1 and 2 respectively.
- the thermal decomposition temperature of the inventive organocuprous precursor is higher than that of the prior art precursor, and thus, the inventive precursor has good thermal stability.
- the changes in the vapor pressure of the titled compound and (hfac) Cu (VTMS) were determined at various temperatures.
- the result in Fig. 3 demonstrates that the inventive precursor has a higher vapor pressure than the prior art compound.
- Example 3 Deposition of a copper film on a substrate
- Copper films were deposited on a TiN or Si0 2 -coated substrate by a CVD process, using the inventive precursor synthesized in Example 1, as well as (hfac) Cu (VTMS) and
- the change in the specific resistance of the film deposited using the inventive precursor depends on the substrate temperature, as shown in Fig. 5. It can be seen from Fig. 5 that the specific resistance of the film deposited at a substrate temperature of 150 °C to 250 °C approximately reaches that of bulk copper (about 1.67 ⁇ cm) .
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Chemical Vapour Deposition (AREA)
- Electrodes Of Semiconductors (AREA)
- Chemically Coating (AREA)
- Other Surface Treatments For Metallic Materials (AREA)
Abstract
L'invention concerne un composé organo-cuivreux correspondant à la formule (I). On peut utiliser de manière pratique ce composé dans un procédé de dépôt chimique en phase vapeur, dans la production à grande échelle d'un film de cuivre dépourvu de contaminants et possédant une bonne stabilité thermique. Dans la formule (I), R1, R2 et R3 représentent chacun indépendamment un groupe alcoxy C1-8, aryle ou aryloxy, R4 et R5 représentent chacun indépendamment hydrogène, fluor, un groupe CnF2n+1 ou CnH2n+1, n étant un nombre entier compris entre 1 et 6, R6 représente hydrogène, fluor ou un groupe alkyle C1-4, et m vaut 1 ou 2 ; lorsque m vaut 1, C=C représente C‰C, et lorsque m vaut 2, C=C représente C=C.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019990013236A KR100298125B1 (ko) | 1999-04-15 | 1999-04-15 | 구리의 화학 증착에 유용한 유기 구리 전구체 |
KR9913236 | 1999-04-15 | ||
PCT/KR1999/000743 WO2000063461A1 (fr) | 1999-04-15 | 1999-12-07 | Nouveaux precurseurs organo-cuivreux destines au depot chimique en phase vapeur d'un film de cuivre |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1102872A1 true EP1102872A1 (fr) | 2001-05-30 |
EP1102872A4 EP1102872A4 (fr) | 2008-04-30 |
Family
ID=19580072
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99959960A Withdrawn EP1102872A4 (fr) | 1999-04-15 | 1999-12-07 | Nouveaux precurseurs organo-cuivreux destines au depot chimique en phase vapeur d'un film de cuivre |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1102872A4 (fr) |
JP (1) | JP2002542397A (fr) |
KR (1) | KR100298125B1 (fr) |
CN (1) | CN1194117C (fr) |
RU (1) | RU2181725C2 (fr) |
TW (1) | TW524881B (fr) |
WO (1) | WO2000063461A1 (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA78180C2 (uk) * | 1997-10-03 | 2007-03-15 | Меріаль | Кільцевий вірус свині типу ii, вакцини та діагностичні реагенти |
KR100358045B1 (ko) * | 1999-12-22 | 2002-10-25 | 주식회사 하이닉스반도체 | 반도체 소자의 구리 금속 배선 형성 방법 |
KR100338112B1 (ko) * | 1999-12-22 | 2002-05-24 | 박종섭 | 반도체 소자의 구리 금속 배선 형성 방법 |
KR100347838B1 (ko) * | 2000-03-07 | 2002-08-07 | 학교법인 포항공과대학교 | 액상 유기구리 전구체의 열적 안정성 향상방법 |
DE10228050A1 (de) * | 2002-06-24 | 2004-01-15 | Merck Patent Gmbh | Dikupfer(I)oxolat-Komplexe als Precursor-Substanzen zur metallischen Kupferabscheidung |
DE10319454A1 (de) * | 2003-04-29 | 2004-11-18 | Merck Patent Gmbh | Dikupfer(I)oxalat-Komplexe als Precursor zur metallischen Kupferabscheidung |
EP1811059B1 (fr) * | 2004-09-27 | 2012-10-31 | Ulvac, Inc. | Procédé de formation de film contenant du cuivre |
DE102009023952A1 (de) | 2009-06-04 | 2010-12-09 | DüRR DENTAL AG | Verfahren und Vorrichtung zur Bestimmung von Zahnfarben |
KR101719526B1 (ko) | 2010-11-17 | 2017-04-04 | 주식회사 유피케미칼 | 다이아자다이엔계 금속 화합물, 이의 제조 방법 및 이를 이용한 박막 형성 방법 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1001047A2 (fr) * | 1998-11-10 | 2000-05-17 | Sharp Kabushiki Kaisha | Précurseur de ligand à base d'alcène et procédé de synthèse |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5187300A (en) * | 1991-02-04 | 1993-02-16 | Air Products And Chemicals, Inc. | Volatile precursors for copper CVD |
US5144049A (en) * | 1991-02-04 | 1992-09-01 | Air Products And Chemicals, Inc. | Volatile liquid precursors for the chemical vapor deposition of copper |
US5358743A (en) * | 1992-11-24 | 1994-10-25 | University Of New Mexico | Selective and blanket chemical vapor deposition of Cu from (β-diketonate)Cu(L)n by silica surface modification |
JP3282392B2 (ja) * | 1994-08-10 | 2002-05-13 | 三菱マテリアル株式会社 | 蒸気圧の高い有機金属化学蒸着による銅薄膜形成用有機銅化合物 |
US5744192A (en) * | 1996-11-08 | 1998-04-28 | Sharp Microelectronics Technology, Inc. | Method of using water vapor to increase the conductivity of cooper desposited with cu(hfac)TMVS |
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1999
- 1999-04-15 KR KR1019990013236A patent/KR100298125B1/ko not_active IP Right Cessation
- 1999-12-07 CN CNB998026484A patent/CN1194117C/zh not_active Expired - Fee Related
- 1999-12-07 WO PCT/KR1999/000743 patent/WO2000063461A1/fr active Application Filing
- 1999-12-07 EP EP99959960A patent/EP1102872A4/fr not_active Withdrawn
- 1999-12-07 JP JP2000612535A patent/JP2002542397A/ja active Pending
- 1999-12-07 RU RU2000118774/04A patent/RU2181725C2/ru not_active IP Right Cessation
- 1999-12-15 TW TW088122014A patent/TW524881B/zh not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1001047A2 (fr) * | 1998-11-10 | 2000-05-17 | Sharp Kabushiki Kaisha | Précurseur de ligand à base d'alcène et procédé de synthèse |
Non-Patent Citations (4)
Title |
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DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; RHEWE, SHI-WOO ET AL: "Property of hfac (hexafluoroacetylacetonate)Cu(I)DMB (3,3-dimethyl-1- butene) as a liquid precursor for chemical vapor deposition of copper films" XP002473287 retrieved from STN Database accession no. 132:159098 & HAN'GUK CHAELYO HAKHOECHI , 9(11), 1148-1152 CODEN: HCHAEU; ISSN: 1225-0562, 1999, * |
DOPPELT P ET AL: "Alkyne complexes of copper(I) (1,1,1,5,5,5-hexafluoro-2,4-pentanedion ato): syntheses and characterization of (eta<2>-bis(trimethylsilyl) acetylene) copper(I) (hfac), (mu-eta<2>-bis(trimethylsilyl) acetylene) bis(copper(I) (hfac)) and a series of (eta<2>-alkyne) Cu(hfac) complexes" JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 517, no. 1, 28 June 1996 (1996-06-28), pages 53-62, XP004035961 ISSN: 0022-328X * |
KANG S-W ET AL: "(hfac)Cu(I)(MP) (hfac=hexafluoroacetylacetonate, MP=4-methyl-1-pentene) and (hfac)Cu(I)(DMB) (DMB=3,3-dimethyl-1-bute ne) for the chemical vapor deposition of copper film" THIN SOLID FILMS, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 350, no. 1-2, 15 August 1999 (1999-08-15), pages 10-13, XP004180583 ISSN: 0040-6090 * |
See also references of WO0063461A1 * |
Also Published As
Publication number | Publication date |
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JP2002542397A (ja) | 2002-12-10 |
CN1194117C (zh) | 2005-03-23 |
TW524881B (en) | 2003-03-21 |
EP1102872A4 (fr) | 2008-04-30 |
KR19990046683A (ko) | 1999-07-05 |
RU2181725C2 (ru) | 2002-04-27 |
WO2000063461A1 (fr) | 2000-10-26 |
CN1290309A (zh) | 2001-04-04 |
KR100298125B1 (ko) | 2001-09-13 |
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