CN106916072B - A kind of five (dimethylamino) tantalum synthetic methods - Google Patents
A kind of five (dimethylamino) tantalum synthetic methods Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 9
- KVKAPJGOOSOFDJ-UHFFFAOYSA-N CN(C)[Ta] Chemical compound CN(C)[Ta] KVKAPJGOOSOFDJ-UHFFFAOYSA-N 0.000 title abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000012298 atmosphere Substances 0.000 claims abstract description 7
- 241000270295 Serpentes Species 0.000 claims abstract description 4
- 238000002202 sandwich sublimation Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 238000010992 reflux Methods 0.000 claims abstract description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 238000012423 maintenance Methods 0.000 claims description 6
- -1 n-BuLi alkane Chemical class 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims description 2
- 230000008022 sublimation Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 6
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 6
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OLUQNHZGDAZRKM-UHFFFAOYSA-N [Li].CNC Chemical class [Li].CNC OLUQNHZGDAZRKM-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 238000000231 atomic layer deposition Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 1
- 230000003667 anti-reflective effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003482 tantalum compounds Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Chemical Vapour Deposition (AREA)
Abstract
The invention discloses a kind of synthetic methods of five (dimethylamino) tantalums, include the following steps：Tantalic chloride and alkane C are added in the reactor of inert atmosphere protectionnH2n+2(n >=6) mixture is added dimethylamine and is reacted under stirring conditions, and the temperature of reaction system is maintained at 0~30 DEG C, after being added dropwise, and is kept for 0~30 DEG C react 8 12 hours.N-BuLi alkane C is added dropwisenH2n+2(n >=6) solution is maintained at 0~30 DEG C and reacts 4 20 hours, then maintains the reflux for reaction 4 12 hours.It is decompressed to 1000 7000Pa and steams alkane CnH2n+2(n >=6) solvent is transferred to doing in sublimator, is decompressed to 50 300Pa and is collected product five (dimethylamino) tantalum.Reagent selected by the method for the present invention is conventional reagent, and inexpensive and be easy to get, operating process is simple, no security risk；The application of snake type sandwich sublimation device, improves product purity and reaction yield；Solvent is reusable needed for reaction, waste is not generated, to environment without any pollution.
Description
Technical field
The present invention relates to material production field more particularly to a kind of five (diformazans of used in electronic industry tantalum compound raw materials for production
Amino) tantalum C10H30N5The synthetic method of Ta.
Background technology
Tantalum nitride (TaN) film is with resistivity is low, fusing point is high, activation energy height, the thermal stability of lattice and grain boundary decision
A series of high excellent performances, therefore the application in microelectronic chip and manufacturing process is than wide.For example, in standard
After CMOS in the copper interconnection technology in road, tantalum nitride membrane is applied frequently as the diffusion impervious layer of copper；In 45nm or less CMOS works
In skill, there is good stability at elevated temperature, therefore be used as metal gates material between tantalum nitride and high-dielectric-coefficient grid medium
Material；In extreme ultraviolet carving technology, tantalum nitride is alternatively arranged as absorbed layer.
Tantalum pentoxide (Ta2O5) film have high-k (25~35), high refractive index and good chemical stabilization
Property, can as dynamic RAM, antireflective film, high temperature impedance, gas sensor, capacitor critical material.Especially,
For tantalum pentoxide as high dielectric constant material, it is more much higher than traditional earth silicon material, therefore may be implemented identical
Capacitance density under possess the physical thickness of bigger, so as to be effectively reduced the leakage current density of device, that improves device can
By property and service life.Currently, tantalum pentoxide is in dynamic RAM, the fields such as RF IC passive capacitive
Good application is obtained.
(dimethylamino) tantalum of critical materials-five C as tantalum nitride and tantalum pentoxide10H30N5Ta, structure are shown in Fig. 1, are
The key reaction source of chemical vapor deposition (CVD) and atomic layer deposition (ALD) technique growth tantalum nitride or tantalum pentoxide.Mesh
Before, the report in relation to five (dimethylamino) tantalum synthetic methods is also limited only to laboratory synthesis, and operating process should not be stablized
Control, reaction yield is low, purity is low.Its primary synthetic methods is：(1) dimethylamine lithium salts is obtained by the reaction with butyl lithium in dimethylamine；
(2) after dimethylamine lithium salts is reacted with tantalic chloride, through filtering, solvent is extracted；(3) crude product will be precipitated and is transferred to sublimator, distil
Obtain crude product.But there are some disadvantages for this method：(1) since side product chlorinated lithium particle is thin and light specific gravity, so when filtering not
Easily filtering, makes troubles to practical operation；(2) solid by-product can wrap up a certain amount of product, and product is caused to lose, and reduce conjunction
At yield；(3) it needs constantly to clean using a large amount of solvents in filter process, therefore reduces efficiency, improve production cost.
Invention content
The object of the present invention is to provide a kind of synthetic methods of five (dimethylamino) tantalums, are closed with solving five (dimethylamino) tantalums
It is bothered at operating process, yield is low, the problem that purity is low, of high cost.
To solve the above-mentioned problems, the present invention provides a kind of five (dimethylamino) tantalum synthetic methods, include the following steps：
Tantalic chloride and alkane C are added in the reactor of inert atmosphere protectionnH2n+2(n >=6) mixture, drips under stirring conditions
Dimethylamine is added to be reacted, the temperature of reaction system is maintained at 0~-30 DEG C, after being added dropwise, and the temperature of reaction system is kept to exist
It is reacted 8-12 hours at 0~-30 DEG C.N-BuLi alkane C is added dropwisenH2n+2(n >=6) solution keeps system temperature 0~-30
It is reacted 4-20 hours at DEG C, then maintains the reflux for reaction 4-12 hours.Pressure in reactor is reduced to 1000-7000Pa, then
Steam alkane CnH2n+2(n >=6) solvent, and product is transferred in sublimator, product five (two is collected under 50-300Pa low pressure
Methylamino) tantalum.
The n-BuLi alkane CnH2n+2(n >=6) solution, n are selected from 6 or 7, and alkane is selected from n-hexane or normal heptane.
Maintenance system temperature is 0~-30 DEG C when the dimethylamine is added.
The molar ratio of the dimethylamine and tantalic chloride is 5:1~10:1.
The n-BuLi alkane CnH2n+2When the addition of (n >=6) solution maintenance system temperature at 0~-30 DEG C ranging from
Preferably.
The tantalic chloride is 1 with butyl lithium molar ratio:5~1:8.
The alkane solvent rectification under vacuum pressure is 1000-7000Pa, and temperature is 30 DEG C~100 DEG C.
The product five (dimethylamino) tantalum Decompression Sublimation pressure is 50-300Pa, and temperature is 50 DEG C~100 DEG C.
The sublimator is snake type sandwich sublimation device.
The inert atmosphere is high pure nitrogen atmosphere or high-purity argon gas atmosphere.
The beneficial effects of the invention are as follows：1, selected reagent is conventional reagent, is easily obtainable；2, reaction process is relatively more flat
With, it is easy to operate controllable, without security risk；3, alkane CnH2n+2(n >=6) are reusable, without waste, to environment without
Pollution；4, the use of snake type sandwich sublimation device, improves the purity for preparing yield and product.
Description of the drawings
Fig. 1 five (dimethylamino) tantalum structural formula
Specific implementation mode
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be further described, the present embodiment
It is only used for explaining the present invention, be not intended to limit the scope of the present invention..
Embodiment 1
Under an argon atmosphere, 180 grams of tantalic chlorides and 500 milliliters of n-hexanes are added in a kettle, under agitation,
It is added 135 grams of anhydrous dimethyl amine into reaction kettle, when addition maintains the temperature at -30 DEG C, and it is small to add holding system thermotonus 10
When, 1000 milliliters of n-BuLi n-hexane molten (2.5mol/L) is then added, adition process maintenance system temperature is -30 DEG C,
It adds and is reacted 16 hours at -30 DEG C, then back flow reaction 4 hours.Cooling is first decompressed to 7000Pa and steams solvent hexane, and temperature is
90℃.Solid is transferred to sublimator by solvent after being evaporated, and is finally decompressed to 300Pa again and is distilled to obtain product five (dimethylamino) tantalum,
Temperature is 90 DEG C, obtains 148.3 grams of product five (dimethylamino) tantalum, yield 74.2%.
Embodiment 2
In a nitrogen atmosphere, 180 grams of tantalic chlorides and 500 milliliters of normal heptanes are added in a kettle, under agitation,
135 grams of anhydrous dimethyl amine is added into reaction kettle, rate is added and maintains the temperature at -10 DEG C, adds holding system thermotonus 10
Hour, 1100 milliliters of n-BuLi normal heptane molten (2.5mol/L) is then added, adition process maintenance system temperature is -10
DEG C, it adds and is reacted 18 hours at -10 DEG C, then back flow reaction 4 hours.Cooling first reduces to 5000Pa and steams solvent n-heptane, temperature
It is 70 DEG C.Solid is transferred to sublimator by solvent after being evaporated, and is finally decompressed to 250Pa again and is distilled to obtain product five (dimethylamino)
Tantalum, temperature are 60 DEG C, obtain 166.5 grams of product five (dimethylamino) tantalum, yield 83.2%.
Embodiment 3
Under an argon atmosphere, 720 grams of tantalic chlorides and 2000 milliliters of normal heptanes are added in a kettle, in stirring condition
Under, 540 grams of anhydrous dimethyl amine is added into reaction kettle, rate is added and maintains the temperature at -20 DEG C, adds holding system thermotonus
10 hours, 4400 milliliters of n-BuLi normal heptane molten (2.5mol/L) is then added, adition process maintenance system temperature is -20
DEG C, add reaction 18 hours, then back flow reaction 4 hours.Cooling is first decompressed to 1000Pa and steams solvent n-heptane, temperature 50
℃.Solid is transferred to sublimator by solvent after being evaporated, and is finally decompressed to 50Pa again and is distilled to obtain product five (dimethylamino) tantalum, temperature
It is 50-100 DEG C, obtains 698.4 grams of product five (dimethylamino) tantalum, yield 87.3%.
In invented technology, reaction and distillation condition are steady, easily controllable, have materials safety stabilization, are easy to get, price
Cheaply, the advantages such as reaction yield and production efficiency height.Gross production rate can reach 90% or more.Alkane CnH2n+2(n >=6) nontoxic, can be with
It reuses, not will produce any waste, be not only suitable for laboratory synthesis, be also suitable for certain scale and be combined to.
Claims (10)
1. one kind five（Dimethylamino）Tantalum synthetic method, which is characterized in that include the following steps：
（1）Tantalic chloride and alkane C are added in the reactor of inert atmosphere protectionnH2n+2Mixture adds under stirring conditions
Enter dimethylamine to be reacted, the temperature of reaction system is maintained at 0~-30 DEG C, after being added dropwise, and keeps 0~-30 DEG C of reaction 8-12
Hour, wherein n >=6；
（2）N-BuLi alkane C is added dropwisenH2n+2Solution is maintained at 0~-30 DEG C and reacts 4-20 hours, then maintains the reflux for reaction 4-
12 hours, wherein n >=6；
（3）Alkane C is steamed under 1000-7000Pa pressurenH2n+2Then product is transferred in sublimator by solvent, depressurizing
Product, wherein n >=6 are collected under the reduced pressure of 50-300Pa.
2. the method as described in claim 1, which is characterized in that the n-BuLi alkane CnH2n+2Solution, n are selected from 6 or 7,
Alkane is selected from n-hexane or normal heptane.
3. the method as described in claim 1, which is characterized in that maintenance system temperature is 0~-30 DEG C when the dimethylamine is added
It is advisable.
4. the method as described in claim 1, which is characterized in that the molar ratio of the dimethylamine and tantalic chloride is 5 ︰, 1~10 ︰
1。
5. the method as described in claim 1, which is characterized in that the n-BuLi alkane CnH2n+2Solution maintains body when being added
It is temperature for 0~-30 DEG C to be advisable, wherein n >=6.
6. the method as described in claim 1, which is characterized in that the tantalic chloride and n-BuLi alkane CnH2n+2Molar ratio
For 1 ︰, 5~1 ︰ 8.
7. the method as described in claim 1, which is characterized in that the alkane solvent rectification under vacuum pressure is 1000-7000Pa,
Temperature is 30 DEG C~100 DEG C.
8. the method as described in claim 1, which is characterized in that the product Decompression Sublimation pressure is 50-300Pa, and temperature is
50 DEG C~100 DEG C.
9. according to the method described in claim 1, it is characterized in that, the sublimator is snake type sandwich sublimation device.
10. the method as described in claim 1, which is characterized in that the inert atmosphere is high pure nitrogen atmosphere or high-purity argon gas
Atmosphere.
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| CN110790671B (en) * | 2019-11-01 | 2022-05-20 | 浙江博瑞电子科技有限公司 | Method for refining pentakis (dimethylamino) tantalum |
| CN114957014A (en) * | 2022-06-21 | 2022-08-30 | 安徽博泰电子材料有限公司 | Preparation method of high-purity pentakis (dimethylamino) tantalum for chip film formation |
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| CN101522695A (en) * | 2006-09-28 | 2009-09-02 | 普莱克斯技术有限公司 | Heteroleptic organometallic compounds |
| CN103601750A (en) * | 2013-10-28 | 2014-02-26 | 南京大学 | Tetrakis(ethylmethylamino)hafnium synthesis method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6960675B2 (en) * | 2003-10-14 | 2005-11-01 | Advanced Technology Materials, Inc. | Tantalum amide complexes for depositing tantalum-containing films, and method of making same |
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Effective date of registration: 20220128 Address after: 215600 Wuxin village, yangshe Town, Zhangjiagang City, Suzhou City, Jiangsu Province (north side of Zhangyang Road) Patentee after: SINOCOMPOUND CATALYSTS CO.,LTD. Address before: 215600 Zhangjiagang Economic Development Zone, Suzhou, Jiangsu Province Patentee before: SUZHOU FORNANO ELECTRONIC TECHNOLOGY Co.,Ltd. |