CN104447839A - Aminopyridyl silicon compound and application thereof - Google Patents
Aminopyridyl silicon compound and application thereof Download PDFInfo
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- CN104447839A CN104447839A CN201410625636.5A CN201410625636A CN104447839A CN 104447839 A CN104447839 A CN 104447839A CN 201410625636 A CN201410625636 A CN 201410625636A CN 104447839 A CN104447839 A CN 104447839A
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Abstract
The invention relates to an aminopyridyl silicon compound. The aminopyridyl silicon compound is prepared through the steps: (1) dissolving aminopyridine or a derivative thereof into a reaction solvent, and adding a lithium alkylide solution under the condition of stirring at the temperature of -78 DEG C to 0 DEG C, wherein the mole ratio of aminopyridine or the derivative thereof to lithium alkylide is 1: (1-1.2); continuing to react for 0.5-3 hours while stirring after the temperature returns to room temperature, so as to obtain a reaction mixture; (2) filtrating the reaction mixture obtained in the step (1) so as to obtain a solid lithium salt, and dissolving the solid lithium salt in an organic solvent, so as to obtain a lithium salt solution; (3) dropwise adding a siliceous reactant or a solution thereof into the lithium salt solution at the temperature of -78 DEG C to 0 DEG C in accordance with that the mole ratio of the lithium salt to the siliceous reactant is (1-4): 1, heating up to a certain temperature, and reacting for 3-10 hours; (4) filtrating the reaction mixture obtained in the step (3), concentrating a filtrate, and then, carrying out crystallization or reduced-pressure distillation, thereby obtaining the aminopyridyl silicon compound. The compound disclosed by the invention can be used for preparing films of silicon nitride, carboniferous silicon nitride and the like in integrated circuit production.
Description
Technical field
The present invention relates to a kind of silicoorganic compound with ad hoc structure and aminopyridine base, this compounds can be used as integrated circuit thin-film material proplastid simultaneously, belongs to technical field of microelectronic material.
Background technology
Along with the development that IC industry is quick and optimum, also had with the requirement of its relevant industries that high technology content, high-quality require, the industry characteristic of three high requests of high entry threshold thereupon, namely this be face new challenges and opportunity for whole unicircuit associated materials.
In the numerous process procedure of unicircuit, silicon-containing film can be used as capacitor films, gate pole film, stops not, the optical component of the optical communication equipment such as the electronic component of the electronic unit such as gate insulation film or optical waveguides, photoswitch, image intensifer, have indispensable status in fields such as photoelectric materials, the development therefore for the silicon-containing film proplastid material of integrated circuit fields has very important practical significance and value.
In CVD/ALD Technology, the character of proplastid is most important, it require proplastid have suitable thermostability and higher volatile while, preparation also should be had simple, and easily the feature such as transport and storage is beneficial to produce and use.Current silicon-containing film proplastid material is gradually from traditional material, such as silane, silicon tetrachloride, disilicone hexachloride, dimethyldichlorosilane(DMCS), dichlorosilane etc. are to the silicoorganic compound transition with ad hoc structure group, and major cause has 3 points: 1) traditional proplastid material is mostly gas or highly volatile liquid not easily stores and transports; 2) traditional proplastid material has suitable toxicity, simultaneously because the chemical property that the extreme of self is active easily causes danger, needs to have high input fund for security work; 3) the general content of halogen of traditional proplastid material is high, in film-forming process, easily produce too much hydrogenchloride, can produce corrosion to equipment.These reasons hinder the industrialization development of traditional silicon-containing film proplastid material to a great extent, simultaneously along with the develop rapidly of IC industry, be badly in need of the novel material of one or more to make up the deficiency of traditional material, and then alternative traditional material, realize industrialization.So investigators start sight to turn to the silicoorganic compound with ad hoc structure group one after another.
Patent CN101648964A and CN102282291A discloses aminosilane proplastid, CN1518076A discloses diazanyl silane proplastid, this two classes proplastid to some extent solves the problem of the highly volatile of traditional material, and convenient storage, but owing to self containing more si-h bond, character is active, therefore still there are some potential danger and has certain toxicity.It is the aminosilane proplastid of basic boom that patent US2010/0285663A1 mainly describes with disilicone hexachloride, this type of proplastid toxicity is little and activity is moderate, but due to the existence of Si prediction skeleton, make its volatility relatively low to a certain extent on the contrary, be unfavorable for the further film forming application of presoma, the relative complex of this type of material synthesis simultaneously.As can be seen here, in patent disclosed in, although the proplastid of the silicon-containing film material found at present all to some extent solves the deficiency that traditional proplastid material exists, but possess suitable thermostability, activity and relative nontoxic and easily the proplastid material of synthesis is still very necessary simultaneously, and there is considerable actual application value.
Summary of the invention
The object of the invention is to overcome traditional silicon-containing film material proplastid and the deficiencies in the prior art, a kind of new type integrated circuit thin-film material aminopyridine radical silicide proplastid is provided, good solvability is had in the organic solvents such as normal hexane, toluene, ether, methylene dichloride, tetrahydrofuran (THF), there are good volatility and thermostability, toxicity is little, activity is moderate, and convenient storage and transport, have good film forming properties.
According to technical scheme provided by the invention, described in there is the aminopyridine radical silicide proplastid of logical formula I:
The position wherein containing N group is in the ortho position of aromatic ring atom N, a position or contraposition, wherein R
1be selected from C
1~ C
10alkyl (as methyl, ethyl, n-propyl, sec.-propyl etc.), C
2~ C
10alkenyl (as vinyl, allyl group etc.), C
2~ C
10alkynyl group (as ethynyl, propargyl etc.), C
3~ C
10cycloalkyl (as cyclopropyl, cyclopentyl, cyclohexyl etc.), C
6~ C
17aryl (as phenyl, o-tolyl, naphthyl etc.) or-Si (R
2r
3r
4), wherein R
2, R
3, R
4independently be selected from hydrogen atom, halogen atom (F, Cl, Br, I), C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl ,-Si (R
2r
3r
4),
or-N (R
5r
6), wherein R
5, R
6independently be selected from hydrogen atom, C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl, wherein R
5, R
6it is asynchronously hydrogen atom.
The prepared preparation method that can be used as the aminopyridine radical silicide of integrated circuit thin-film material proplastid, is characterized in that, comprise the following steps:
(1) aminopyridine or derivatives thereof is dissolved in reaction solvent, the mass ratio of aminopyridine or derivatives thereof and reaction solvent is 1:10 ~ 1:20, alkyl lithium solution is added under keeping at-78 ~ 0 DEG C the condition stirred, the mol ratio of aminopyridine or derivatives thereof and lithium alkylide is 1:1 ~ 1.2, the concentration of alkyl lithium solution is 1.0 ~ 2.5M, and stirring velocity is 800 ~ 2000 revs/min; Continue stirring reaction after returning to room temperature 0.5 ~ 3 hour, obtain reaction mixture, further, described reaction solvent is normal hexane, toluene, methylene dichloride, tetrahydrofuran (THF) or ether;
(2) reaction mixture step (1) obtained filters, collect filter cake, obtain lithium salts solid, lithium salts solid is mixed with organic solvent, the mass ratio of lithium salts solid and organic solvent is 1:10 ~ 20, obtain lithium salt solution, further, described reaction solvent is normal hexane, toluene, methylene dichloride, tetrahydrofuran (THF) or ether;
(3) at-78 ~ 0 DEG C according to lithium salts and siliceous reactant molar ratio 1 ~ 4:1, siliceous reactant or its above-mentioned solution is dripped in above-mentioned lithium salt solution, slowly rise to certain temperature, wherein said temperature is room temperature to reflux temperature corresponding to solvent for use, continues stirring reaction 3 ~ 10 hours at this temperature;
(4) filtered by the reaction mixture that step (3) obtains, filter vacuum concentrates the aminopyridine radical silicide that rear low temperature crystallization or underpressure distillation obtain logical formula I;
(5) or in step (3) stirring after 2 ~ 6 hours, at-78 ~ 0 DEG C, add the organic amine of 1 ~ 10 molar equivalent, slowly rise to certain temperature, described temperature is that room temperature is to reflux temperature, continue stirring reaction at this temperature again 2 ~ 6 hours, filter vacuum concentrates the aminopyridine radical silicide that rear low temperature crystallization or underpressure distillation obtain logical formula I.
Further, above-mentionedly all to carry out under rare gas element is as the protection such as nitrogen, argon gas in steps.
Further, alkyl lithium solution described in described step (1) is lithium methide, n-Butyl Lithium, the ether of tert-butyl lithium or hexane solution.
Further, in described step (3), siliceous reactant is SiX
4, SiHX
3, SiH
2x
2, SiH
3x, Si
2x
6, (CH
3)
3siX, (CH
3)
2siX
2, (CH
3) SiX
3, (CH
3)
2siHX, (CH
3) SiH
2x, (CH
3) SiHX
2in one, wherein X=F, Cl, Br or I.
Further, in described step (3) and (5), heat-up rate is 0.5 ~ 1 DEG C/min.
Further, in described step (5), organic amine has following structure: R
5r
6nH, wherein R
5, R
6independently be selected from hydrogen atom, C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl, further R
5, R
6be asynchronously from hydrogen atom.
Further, the reaction mixture that described step (4) or (5) obtain filters, and after filtrate is concentrated, then carry out low temperature crystallization, or underpressure distillation obtains described aminopyridine silicon compound; The condition that described filtrate is concentrated is: at 20 ~ 50 DEG C of concentrating under reduced pressure, and concentrated or underpressure distillation pressure is-0.1 ~-0.01MPa.
Further, by chemical vapour deposition (CVD) or ald (ALD) technique, preparation silicon-containing film.
Further, above-mentioned depositing temperature is 30 ~ 900 DEG C.
Further, described reactant gases can be one or more mixed gass formed in himself and nitrogen, hydrogen, argon gas.
Further, described film is that one or more adopting in proplastid as claimed in claim 1 and ammonia, nitrous oxide, nitrogen protoxide, oxygen, ozone, water vapour are reacted and obtained.
Further, described film comprises silicon nitride, containing the silicon oxide of carbonitride of silicium, silicon oxynitride, silicon carbide, silicon oxide, carbon doping and the silicon oxynitride film of carbon doping.
Further, above-mentioned deposit film technique, the preferential cyclic chemical vapor deposition by use low-pressure chemical vapor deposition, hot-wire chemical gas-phase deposition, ald, the ald of plasma enhancing, the chemical vapour deposition of plasma enhancing and plasma enhancing carries out.
The present invention has the following advantages:
(1) synthesis condition is gentle, reduces the synthesis cost of front material;
(2) at toluene, ether, methylene dichloride, tetrahydrofuran (THF), has good solvability in the organic solvents such as normal hexane, makes transportation of materials, conveying, the course of processing become simple and easy to operate;
(3) this proplastid material non-toxic, lively type are moderate, and danger coefficient reduces greatly;
(4) have good volatility and thermostability, as through thermogravimetric (TG) method to the test of material thermal property, under normal pressure, there is following structure
proplastid, its T
50be 207 DEG C, Minimum Residual surplus reaches 0.8%, (see Fig. 1);
(5) there is good film forming properties, still for above-mentioned proplastid, with N
2/ H
2mixed gas is carrier gas and reacts, and under 600 DEG C of conditions, can form good cvd film, the scanning electron microscope (SEM) photograph of prepared film is shown in Fig. 2.
Accompanying drawing explanation
Technical scheme of the present invention is described in detail referring to accompanying drawing, wherein:
Fig. 1 is for having structural formula
the TG collection of illustrative plates of proplastid, X-coordinate is temperature, and unit is DEG C, and ordinate zou is rate of weight loss, and unit is %.
Fig. 2 is for having structural formula
cVD film scanning Electronic Speculum (SEM) figure of proplastid.
Embodiment
Below in conjunction with specific embodiment and accompanying drawing, the invention will be further described.
The preparation method of aminopyridine radical silicide of the present invention, is undertaken by formula I reaction:
The position wherein containing N group is in the ortho position of aromatic ring atom N, a position or contraposition, wherein R
1be selected from C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl or-Si (R
2r
3r
4), wherein R
2, R
3, R
4independently be selected from hydrogen atom, halogen atom (F, Cl, Br, I), C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl ,-Si (R
2r
3r
4),
or-N (R
5r
6), wherein R
5, R
6independently be selected from hydrogen atom, C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl, wherein R
5, R
6it is asynchronously hydrogen atom;
Wherein RLi solution is lithium methide, n-Butyl Lithium, the ether of tert-butyl lithium or hexane solution;
Wherein siliceous reactant is SiX
4, SiHX
3, SiH
2x
2, SiH
3x, Si
2x
6, (CH
3)
3siX, (CH
3)
2siX
2, (CH
3) SiX
3, (CH
3)
2siHX, (CH
3) SiH
2x, (CH
3) SiHX
2in one, wherein X=F, Cl, Br or I.
Embodiment one: a kind of preparation method of aminopyridine radical silicide proplastid, comprises the following steps:
(1) will
be dissolved in normal hexane solvent,
be 1:10 with the mass ratio of normal hexane solvent, add in the diethyl ether solution of lithium methide under keeping at 0 DEG C the condition stirred,
be 1:1 with the mol ratio of lithium methide, the concentration of the diethyl ether solution of lithium methide is 1.0M, and stirring velocity is 800 revs/min; Continue stirring reaction after returning to room temperature 0.5 hour, obtain reaction mixture;
(2) reaction mixture step (1) obtained filters, and collect filter cake, obtain lithium salts solid, mixed by lithium salts solid with normal hexane, the mass ratio of lithium salts solid and normal hexane is 1:10, obtains the hexane solution of lithium salts;
(3) at 0 DEG C according to lithium salts and SiH
2cl
2mol ratio 2:1, is added drop-wise to two SiH by the hexane solution of lithium salts
2cl
2hexane solution in, be slowly warming up to room temperature, heat-up rate is 0.5 DEG C/min, at room temperature continues stirring reaction 10 hours;
(4) filtered by the reaction mixture that step (3) obtains, after-29 DEG C repeatedly recrystallization, obtain target product after the lower 20 DEG C of concentrating under reduced pressure filtrates of-0.01MPa, structural formula is:
productive rate: 77%, fusing point: 174 ~ 176 DEG C.
Embodiment two: a kind of preparation method of aminopyridine radical silicide proplastid, comprises the following steps:
(1) will
be dissolved in toluene solvant,
be 1:15 with the mass ratio of toluene solvant, add in the hexane solution of tert-butyl lithium under keeping at-39 DEG C the condition stirred,
be 1:1.1 with the mol ratio of tert-butyl lithium, the concentration of the hexane solution of tert-butyl lithium is 1.5M, and stirring velocity is 1500 revs/min; Continue stirring reaction after returning to room temperature 1.5 hours, obtain reaction mixture;
(2) reaction mixture step (1) obtained filters, and collect filter residue, obtain lithium salts solid, mixed by lithium salts solid with toluene, the mass ratio of lithium salts solid and toluene is 1:20, obtains the toluene solution of lithium salts;
(3) at-39 DEG C according to lithium salts and SiF
4mol ratio 1:1, is added drop-wise to SiF by the toluene solution of lithium salts
4toluene solution in, be slowly warming up to 110 DEG C, heat-up rate is 1 DEG C/min, continues stirring reaction 7 hours at 110 DEG C;
(4) room temperature is returned to, add the TERTIARY BUTYL AMINE of 6 molar equivalents, slowly rise to 110 DEG C, continue stirring reaction at this temperature again 5 hours, the reaction mixture obtained is filtered, after the lower 30 DEG C of concentrating under reduced pressure filtrates of-0.03MPa, after 0 DEG C repeatedly recrystallization, obtain target product, structural formula is:
productive rate: 63%, fusing point: 235 ~ 238 DEG C.
Embodiment three: a kind of preparation method of aminopyridine radical silicide proplastid, comprises the following steps:
(1) will
be dissolved in ether solvent,
be 1:15 with the mass ratio of ether solvent, add in the diethyl ether solution of n-Butyl Lithium under keeping at-53 DEG C the condition stirred,
be 1:1.2 with the mol ratio of n-Butyl Lithium, the concentration of the diethyl ether solution of n-Butyl Lithium is 1.6M, and stirring velocity is 2000 revs/min; Continue stirring reaction after returning to room temperature 3 hours, obtain reaction mixture;
(2) reaction mixture step (1) obtained filters, and collect filter residue, obtain lithium salts solid, mixed by lithium salts solid with ether, the mass ratio of lithium salts solid and ether is 1:15, obtains the diethyl ether solution of lithium salts;
(3) at-53 DEG C according to lithium salts and SiCl
4mol ratio 4:1, is added drop-wise to SiCl by the diethyl ether solution of lithium salts
4diethyl ether solution in, continue stirring reaction 4 hours at this temperature;
(4) filtered by the reaction mixture that step (3) obtains, after the lower 50 DEG C of concentrating under reduced pressure filtrates of-0.1MPa, under-0.1MPa, underpressure distillation obtains target product, and structural formula is:
productive rate: 83%.
Embodiment four: a kind of preparation method of aminopyridine radical silicide proplastid, comprises the following steps:
(1) will
be dissolved in tetrahydrofuran solvent,
be 1:20 with the mass ratio of tetrahydrofuran solvent, add in the diethyl ether solution of n-Butyl Lithium under keeping at-78 DEG C the condition stirred,
be 1:1.2 with the mol ratio of n-Butyl Lithium, the concentration of the diethyl ether solution of n-Butyl Lithium is 2.5M, and stirring velocity is 2000 revs/min; Continue stirring reaction after returning to room temperature 3 hours, obtain reaction mixture;
(2) reaction mixture step (1) obtained filters, and collect filter residue, obtain lithium salts solid, mixed by lithium salts solid with ether, the mass ratio of lithium salts solid and ether is 1:15, obtains the diethyl ether solution of lithium salts;
(3) at 34 DEG C according to lithium salts and (CH
3)
3siI mol ratio 1:1, is added drop-wise to (CH by the diethyl ether solution of lithium salts
3)
3in the diethyl ether solution of SiI, continue stirring reaction 3 hours at this temperature;
(4) filtered by the reaction mixture that step (3) obtains, after the lower 40 DEG C of concentrating under reduced pressure filtrates of-0.06MPa, under-0.01MPa, underpressure distillation obtains target product, and structural formula is:
productive rate: 89%.
The aminopyridine radical silicide that the present invention obtains can be used as the proplastid of CVD/ALD, by chemical vapour deposition (CVD) or ald (ALD) technique, form the silicon oxynitride film of silicon nitride, silicon oxynitride, silicon carbide, silicon oxide, the silicon nitride of carbon doping, the silicon oxide of carbon doping and carbon doping.Described deposit film technique, further preferably by using low-pressure chemical vapor deposition, hot-wire chemical gas-phase deposition, ald, the ald of plasma enhancing, the cyclic chemical vapor deposition of the chemical vapour deposition of plasma enhancing and plasma enhancing carries out.
The present invention has the following advantages: (1) simple synthetic method, and mild condition greatly reduces the synthesis cost of front material; (2) at toluene, ether, methylene dichloride, tetrahydrofuran (THF), has good solvability in the organic solvents such as normal hexane, makes transportation of materials, conveying, the course of processing become simple and easy to operate; (3) this proplastid material non-toxic, lively type are moderate, and danger coefficient reduces greatly; (4) have good volatility and thermostability, as through thermogravimetric (TG) method to the test of material thermal property, under normal pressure, there is following structure
proplastid, its T
50be 207 DEG C, Minimum Residual surplus reaches 0.8%, (see Fig. 1); (5) there is good film forming properties, still for above-mentioned proplastid, with N
2/ H
2mixed gas is carrier gas, and under 600 DEG C of conditions, can form good cvd film, the scanning electron microscope (SEM) photograph of prepared film is shown in Fig. 2.
Claims (10)
1. one kind has the aminopyridine radical silicide of logical formula I:
The position wherein containing N group is in the ortho position of aromatic ring atom N, a position or contraposition, wherein R
1be selected from C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl or-Si (R
2r
3r
4), wherein R
2, R
3, R
4independently be selected from hydrogen atom, halogen atom (F, Cl, Br, I), C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl ,-Si (R
2r
3r
4),
or-N (R
5r
6), wherein R
5, R
6independently be selected from hydrogen atom, C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl, wherein R
5, R
6it is asynchronously hydrogen atom.
2. prepare as claimed in claim 1 containing a method for aminopyridine radical silicide, it is characterized in that, comprise following synthesis step:
(1) aminopyridine or derivatives thereof is dissolved in reaction solvent, the mass ratio of aminopyridine or derivatives thereof and reaction solvent is 1:10 ~ 1:20, alkyl lithium solution is added under keeping at-78 ~ 0 DEG C the condition stirred, the mol ratio of aminopyridine or derivatives thereof and lithium alkylide is 1:1 ~ 1.2, the concentration of alkyl lithium solution is 1.0 ~ 2.5M, and stirring velocity is 800 ~ 2000 revs/min; Continue stirring reaction after returning to room temperature 0.5 ~ 3 hour, obtain reaction mixture, described reaction solvent is normal hexane, toluene, methylene dichloride, tetrahydrofuran (THF) or ether;
(2) reaction mixture step (1) obtained filters, collect filter cake, obtain lithium salts solid, lithium salts solid is mixed with organic solvent, the mass ratio of lithium salts solid and organic solvent is 1:10 ~ 20, obtain lithium salt solution, described reaction solvent is normal hexane, toluene, methylene dichloride, tetrahydrofuran (THF) or ether;
(3) at-78 ~ 0 DEG C according to lithium salts and siliceous reactant molar ratio 1 ~ 4:1, siliceous reactant or its above-mentioned solution is dripped in above-mentioned lithium salt solution, slowly rise to certain temperature, described temperature is the reflux temperature of room temperature to solvent for use, continues stirring reaction 3 ~ 10 hours at this temperature;
(4) filtered by the reaction mixture that step (3) obtains, filter vacuum concentrates the aminopyridine radical silicide that rear low temperature crystallization or underpressure distillation obtain logical formula I;
(5) or in step (3) stirring after 3 ~ 10 hours, at-78 ~ 0 DEG C, add the organic amine of 1 ~ 10 molar equivalent, slowly rise to certain temperature, described temperature is the reflux temperature of room temperature to solvent for use, continue stirring reaction at this temperature again 3 ~ 10 hours, filter vacuum concentrates the aminopyridine radical silicide that rear low temperature crystallization or underpressure distillation obtain logical formula I.
3. preparation method as claimed in claim 2, is characterized in that: alkyl lithium solution described in step (1) is lithium methide, n-Butyl Lithium, the ether of tert-butyl lithium or hexane solution.
4. preparation method as claimed in claim 2, it is characterized in that: in described step (3), siliceous reactant is SiX
4, SiHX
3, SiH
2x
2, SiH
3x, Si
2x
6, (CH
3)
3siX, (CH
3)
2siX
2, (CH
3) SiX
3, (CH
3)
2siHX, (CH
3) SiH
2x, (CH
3) SiHX
2in one, wherein X=F, Cl, Br or I.
5. preparation method as claimed in claim 2, is characterized in that: in described step (3) and (5), heat-up rate is 0.5 ~ 1 DEG C/min.
6. preparation method as claimed in claim 2, is characterized in that: in described step (5), organic amine has following structure: R
5r
6nH, wherein R
5, R
6independently be selected from hydrogen atom, C
1~ C
10alkyl, C
2~ C
10alkenyl, C
2~ C
10alkynyl group, C
3~ C
10cycloalkyl, C
6~ C
17aryl, further R
5, R
6be asynchronously from hydrogen atom.
7. preparation method as claimed in claim 2, it is characterized in that: the reaction mixture that described step (4) or (5) obtain filters, after filtrate is concentrated, then carry out low temperature crystallization, or underpressure distillation obtains described aminopyridine silicon compound; The condition that described filtrate is concentrated is: at 20 ~ 50 DEG C of concentrating under reduced pressure, and concentrated or underpressure distillation pressure is-0.1 ~-0.01MPa.
8. be used as the application of integrated circuit thin-film material proplastid as claimed in claim 1 containing aminopyridine radical silicide, it is characterized in that: by chemical vapour deposition (CVD) or ald (ALD) technique, preparation silicon-containing film.
9. apply as claimed in claim 8, it is characterized in that: described film is that one or more adopting in proplastid as claimed in claim 1 and ammonia, nitrous oxide, nitrogen protoxide, oxygen, ozone, water vapour are reacted and obtained.
10. apply as claimed in claim 8, it is characterized in that: described film comprises silicon nitride, containing the silicon oxide of carbonitride of silicium, silicon oxynitride, silicon carbide, silicon oxide, carbon doping and the silicon oxynitride film of carbon doping.
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| CN103397306A (en) * | 2006-05-23 | 2013-11-20 | 气体产品与化学公司 | Process for producing silicon oxide film from organoaminosilane precursors |
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| OLIVIER MAHE等，: "Deoxofluorination Reactions Using N,N-Disubstituted Aminodifluorosulfinium Tetrafluoroborate Salts", 《JOURNAL OF FLUORINE CHEMISTRY》 * |
| TSUYOSHI MITA等，: "Iridium- and Rhodium-Catalyzed Dehydrogenative Silylations of CACHTUNGTRENUNG(sp3)_H", 《CHEM. ASIAN J.》 * |
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| CN104447839B (en) | 2017-10-31 |
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