CN104341447B - A kind of silicon compound of amidino groups containing N and its application - Google Patents
A kind of silicon compound of amidino groups containing N and its application Download PDFInfo
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Abstract
The present invention relates to a kind of silicon compound of amidino groups containing N, prepared according to following methods：(1) carbodiimide or derivatives thereof is dissolved in reaction dissolvent, it is 1 with the mol ratio of alkane/amido lithium that alkane/amido lithium solution, aminopyridine or derivatives thereof are added under 78~0 DEG C of stirring conditions:1~1.2；Continue stirring reaction 0.5~3 hour after returning to room temperature, obtain reactant mixture；(2) the reactant mixture filtering for obtaining step (1), obtains lithium salts solid, and lithium salts solid is dissolved in into organic solvent, obtains lithium salt solution；(3) at 78~0 DEG C according to lithium salts and siliceous reactant molar ratio 1~4:1~1.1, to siliceous reactant or its solution are added dropwise in lithium salt solution, rise to uniform temperature and react 3~10 hours；(4) reactant mixture that step (3) is obtained is filtered, crystallization or vacuum distillation obtain silicon compound containing amidine ligand after filtrate concentration.Compound of the present invention can be in integrated circuit production for preparing silicon nitride, containing films such as carbonitride of silicium.
Description
Technical field
With ad hoc structure be the silicon compound of amidino groups containing N the present invention relates to one kind, at the same such compound can be used as it is integrated
Circuit film material proplastid, belongs to technical field of microelectronic material.
Background technology
With the quick and benign development of IC industry, the requirement of industry associated therewith also has high-tech to contain therewith
Amount, high-quality requirement, the industry characteristic of three high requests of entry threshold high, this for whole integrated circuit associated materials,
It is to face new challenges and opportunity.
In the numerous process procedures of integrated circuit, silicon-containing film be used as capacitor films, gate pole film, stop not, door
The optical component of the optical communication equipment such as electronic component or fiber waveguide, photoswitch, image intensifer of the electronic units such as pole dielectric film,
There is indispensable status in fields such as photoelectric materials, thus be accordingly used in the silicon-containing film proplastid material of integrated circuit fields
Developing has highly important practical significance with value.
In CVD/ALD technologies, the property of proplastid is most important, and it is appropriate thermally-stabilised that it requires that proplastid has
Property and it is higher it is volatile should also have preparation simple simultaneously, easily transport and be beneficial to production and use the features such as store.
Current silicon-containing film proplastid material is gradually from traditional material such as silane, silicon tetrachloride, disilicone hexachloride, dimethyl dichloro
Silane, dichlorosilane etc. have at 3 points to the organo-silicon compound transition with ad hoc structure group, main cause：1) traditional antecedent
Body material is mostly gas or highly volatile liquid is difficult storage with transport；2) traditional proplastid material has suitable poison
Property, simultaneously because the active chemical property of the extreme of itself easily causes dangerous, it is necessary to put into extensive fund for security work；
3) traditional proplastid general content of halogen of material is high, and excessive hydrogen chloride is easily produced in film-forming process, and equipment can be produced
Corrosion.These reasons largely hinder the industrialization development of traditional silicon-containing film proplastid material, while with collection
Into developing rapidly for circuit industry, it is badly in need of the new material of one or more to make up the deficiency of traditional material, and then substitute tradition
Material, realizes industrialization.Then researchers start sight to be turned to one after another the organo-silicon compound with ad hoc structure group.
Patent CN101648964A and CN102282291A disclose amino silane proplastid, and CN1518076A is disclosed
Diazanyl silane proplastid, this two classes proplastid solves the problems, such as the highly volatile of traditional material to a certain extent, and convenient
Storage, but due to itself containing more si-h bond, property is active, therefore it is potential dangerous and with one that some are still present
Fixed toxicity.Patent US2010/0285663A1 mainly describes the amino silane antecedent with disilicone hexachloride as basic boom
Body, such proplastid small toxicity and activity is moderate, but due to the presence of Si prediction skeleton, make it on the contrary to a certain extent
Under volatility is relatively low, it is unfavorable for the further film forming application of presoma, while the synthesis of such material is relative complex.Thus may be used
See, in disclosed patent, although the proplastid of the silicon-containing film material having now been found that all is solved to a certain extent
The deficiency that traditional proplastid material is present, but it is provided simultaneously with suitable heat endurance, activity and relative nontoxic and easily
The proplastid material of synthesis is still very necessary, and with considerable actual application value.
The content of the invention
The purpose of the present invention is to overcome traditional silicon-containing film material proplastid and the deficiencies in the prior art, there is provided
A kind of new type integrated circuit thin-film material silicon compound proplastid of amidino groups containing N, n-hexane, toluene, ether, dichloromethane,
There is preferable dissolubility in the organic solvents such as tetrahydrofuran, there is good volatility and heat endurance, small toxicity, activity is fitted
In, it is convenient to store and transport, with good filming performance.
According to the technical scheme that the present invention is provided, the silicon compound proplastid of amidino groups containing N with formula (I)：
Wherein R1Selected from C1~C10Alkyl (such as methyl, ethyl, n-propyl, isopropyl), C2~C10Alkenyl (such as ethene
Base, pi-allyl etc.), C2~C10Alkynyl group (such as acetenyl, propargyl), C3~C10Cycloalkyl (such as cyclopropyl, cyclopenta, ring
Hexyl etc.), C6~C17Aryl (such as phenyl, o-tolyl, naphthyl) ,-N (SiMe3)2Or-N (R5R6), wherein R2、R3It is independent
Selected from C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl, wherein R4、R5、
R6It is independent selected from hydrogen atom, halogen atom (F, Cl, Br, I), C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3
~C10Cycloalkyl, C6~C17Aryl ,-Si (R2R3R4)、Or-N (R7R8), wherein R5、R6Independent is selected from
Hydrogen atom, C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl, wherein R7、R8
It is independent selected from hydrogen atom, C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Virtue
Base, wherein R7、R8It is asynchronously hydrogen atom.
The preparation method of the prepared silicon compound of amidino groups containing N that can be used as integrated circuit thin-film material proplastid, it is special
Levying is, comprises the following steps：
(1) carbodiimide or derivatives thereof is dissolved in reaction dissolvent, carbodiimide or derivatives thereof and reaction dissolvent
Mass ratio be 1:10~1:20, under conditions of being kept stirring at -78~0 DEG C add alkane/amido lithium solution, carbodiimide or its
Derivative is 1 with the mol ratio of lithium alkylide alkane/amine:1~1.2, the concentration of alkane/amido lithium solution is 1.0~2.5M, mixing speed
It is 800~2000 revs/min；Continue stirring reaction 0.5~3 hour after returning to room temperature, obtain reactant mixture, the reaction
Solvent is n-hexane, toluene, dichloromethane, tetrahydrofuran or ether；
(2) step (1) is obtained reactant mixture filtering, collect filter cake, obtain lithium salts solid, by lithium salts solid with have
Machine solvent mixes, and lithium salts solid is 1 with the mass ratio of organic solvent:10~20, lithium salt solution is obtained, the reaction dissolvent is for just
Hexane, toluene, dichloromethane, tetrahydrofuran or ether；
(3) at -78~0 DEG C according to lithium salts and siliceous reactant molar ratio 1~4:1, contain to being added dropwise in above-mentioned lithium salt solution
Pasc reaction thing or its above-mentioned solution, are slowly increased to uniform temperature, and the temperature is reflux temperature of the room temperature to solvent for use, herein
At a temperature of continue stirring reaction 3~10 hours；
(4) reactant mixture that step (3) is obtained is filtered, low temperature crystallization or decompression are steamed after filter vacuum concentration
Evaporate the silicon compound of amidino groups containing N for obtaining formula (I)；
(5) or after step (3) is stirred 3~10 hours, at -78~0 DEG C, the organic of 1~10 molar equivalent is added
Amine, is slowly increased to uniform temperature, and the temperature is reflux temperature of the room temperature to solvent for use, stirring is further continued at this temperature anti-
Answer 3~10 hours, low temperature crystallization or vacuum distillation obtain the silicon compound of amidino groups containing N of formula (I) after filter vacuum concentration.
Further, above-mentioned all steps are carried out under inert gas such as nitrogen, argon gas protection.
Further, alkane described in step (1)/amido lithium solution is with structure R1The ether or n-hexane of Li are molten
Liquid, wherein R1Selected from C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl ,-N
(SiMe3)2Or-N (R5R6), wherein wherein R5、R6It is independent selected from hydrogen atom, C1~C10Alkyl, C2~C10Alkenyl, C2~
C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl.
Further, in the step (3), siliceous reactant is SiX4、SiHX3、SiH2X2、SiH3X、Si2X6、(CH3)3SiX、(CH3)2SiX2、(CH3)SiX3、(CH3)2SiHX、(CH3)SiH2X、(CH3)SiHX2In one kind, wherein X=F, Cl, Br
Or I.
Further, in the step (3) and (5), programming rate is 0.5~1 DEG C/min.
Further, organic amine has following structure in the step (5)：R7R8NH, wherein R7、R8It is independent selected from hydrogen
Atom, C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl, further
R7、R8It is asynchronously from hydrogen atom.
Further, the reactant mixture that the step (4) or (5) obtain is filtered, and after filtrate is concentrated, then is carried out
Low temperature crystallization, or vacuum distillation obtains the described silicon compound of amidino groups containing N；The condition of filtrate concentration is：20~50
DEG C concentrated under reduced pressure, concentration or vacuum distillation pressure are -0.1~-0.01MPa.
Further, by chemical vapor deposition (CVD) or ald (ALD) technique, silicon-containing film is prepared.
Further, above-mentioned depositing temperature is 30~900 DEG C.
Further, described reacting gas can be that its own is formed with one or more in nitrogen, hydrogen, argon gas
Mixed gas.
Further, the film is using proplastid as claimed in claim 1 and ammonia, nitrous oxide, an oxidation
One or more reactions in nitrogen, oxygen, ozone, vapor are obtained.
Further, the film is including silicon nitride, containing carbonitride of silicium, silicon oxynitride, carborundum, silica, carbon doping
Silica and carbon doping silicon oxynitride film.
Further, above-mentioned deposition film technique, is preferentially sunk by using low-pressure chemical vapor deposition, Hot Filament Chemical Vapor
Product, ald, the ald of plasma enhancing, the chemical vapor deposition of plasma enhancing and plasma increase
Strong cyclic chemical vapor deposition is carried out.
Beneficial effects of the present invention include：
(1) synthesis condition is gentle, reduces the synthesis cost of preceding material；
(2) in toluene, ether, dichloromethane, tetrahydrofuran has preferable dissolubility in the organic solvent such as n-hexane,
So that transport of materials, conveying, process become simple and easy to operate；
(3) this proplastid material non-toxic, lively type are moderate, and danger coefficient is substantially reduced；
(4) there is a good volatility and heat endurance, such as test by thermogravimetric (TG) method to material thermal property, often
Pressure has following structureProplastid, its T50 be 80 DEG C, minimum residual volume up to 0%, (see Fig. 1)；
(5) with good filming performance, still by taking above-mentioned proplastid as an example, with N2/H2Mixed gas is carrier gas and reacts, 600 DEG C
Under the conditions of, good cvd film can be formed, the scanning electron microscope (SEM) photograph of prepared film is shown in Fig. 2.
Brief description of the drawings
Describe technical scheme in detail referring to the drawings, wherein：
Fig. 1 is with structural formulaThe TG collection of illustrative plates of proplastid, abscissa is temperature, unit for DEG C, indulge and sit
Weight-loss ratio is designated as, unit is %.
Fig. 2 is with structural formulaCVD film ESEM (SEM) figure of proplastid.
Specific embodiment
With reference to specific embodiment and accompanying drawing, the invention will be further described.
The preparation method of the silicon compound of amidino groups containing N of the present invention, is carried out by formula (I) reaction：
Wherein R1Selected from C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Virtue
Base ,-N (SiMe3)2Or-N (R5R6), wherein R2、R3It is independent selected from C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkyne
Base, C3~C10Cycloalkyl, C6~C17Aryl, wherein R4、R5、R6It is independent selected from hydrogen atom, halogen atom (F, Cl, Br, I), C1
~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl ,-Si (R2R3R4)、Or-N (R7R8), wherein R5、R6It is independent selected from hydrogen atom, C1~C10Alkyl, C2~C10Alkenyl, C2
~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl, wherein R7、R8It is independent selected from hydrogen atom, C1~C10Alkyl, C2~
C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl, wherein R7、R8It is asynchronously hydrogen atom；
Wherein there is structure R1The ether or hexane solution of Li, further R1Selected from C1~C10Alkyl, C2~C10Chain
Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl ,-N (SiMe3)2Or-N (R5R6), wherein R5、R6It is independent
Selected from hydrogen atom, C1~C10Alkyl, C2~C10Alkenyl, C2~C10Alkynyl group, C3~C10Cycloalkyl, C6~C17Aryl；
Wherein siliceous reactant is SiX4、SiHX3、SiH2X2、SiH3X、Si2X6、(CH3)3SiX、(CH3)2SiX2、(CH3)
SiX3、(CH3)2SiHX、(CH3)SiH2X、(CH3)SiHX2In one kind, wherein X=F, Cl, Br or I.
Embodiment one：A kind of preparation method of the silicon compound of amidino groups containing N proplastid, comprises the following steps：
(1) willIt is dissolved in n-hexane solvent,With n-hexane solvent
Mass ratio be 1:10, add LiNiPr under conditions of being kept stirring at -78 DEG C2Diethyl ether solution in,With LiNiPr2Mol ratio be 1:1, LiNiPr2Diethyl ether solution concentration be 1.0M, mixing speed
It is 800 revs/min；Continue stirring reaction 0.5 hour after returning to room temperature, obtain reactant mixture；
(2) step (1) is obtained reactant mixture filtering, collect filter residue, obtain lithium salts solid, by lithium salts solid with just
Hexane mixes, and lithium salts solid is 1 with the mass ratio of n-hexane:10, obtain the hexane solution of lithium salts；
(3) at 0 DEG C according to lithium salts and SiH2Cl2Mol ratio 2:1, the hexane solution of lithium salts is added drop-wise to two SiH2Cl2's
In hexane solution, room temperature is to slowly warm up to, programming rate is 0.5 DEG C/min, continues stirring reaction 10 hours at room temperature；
(4) reactant mixture that step (3) is obtained is filtered, after the lower 20 DEG C of filtrates concentrated under reduced pressure of -0.01MPa, -29
Target product is obtained after recrystallizing DEG C repeatedly, structural formula is：Yield：73%, fusing point：149~152 DEG C.
Embodiment two：A kind of preparation method of the silicon compound of amidino groups containing N proplastid, comprises the following steps：
(1) willIt is dissolved in toluene solvant,With toluene solvant
Mass ratio is 1:15, under conditions of being kept stirring at -39 DEG C in the hexane solution of addition tert-butyl lithium,It is 1 with the mol ratio of tert-butyl lithium:1.1, the concentration of the hexane solution of tert-butyl lithium is 1.5M,
Mixing speed is 1500 revs/min；Continue stirring reaction 1.5 hours after returning to room temperature, obtain reactant mixture；
(2) the reactant mixture filtering for obtaining step (1), collects filter residue, lithium salts solid is obtained, by lithium salts solid and first
Benzene mixes, and lithium salts solid is 1 with the mass ratio of toluene:20, obtain the toluene solution of lithium salts；
(3) at -78 DEG C according to lithium salts and SiF4Mol ratio 1:1, the toluene solution of lithium salts is added drop-wise to SiF4Toluene solution
In, 110 DEG C are to slowly warm up to, programming rate is 1 DEG C/min, and stirring reaction is continued 7 hours at 110 DEG C；
(4) recover to room temperature, the tert-butylamine of 6 molar equivalents of addition is slowly increased to 110 DEG C, is further continued for stirring at this temperature
Reaction 5 hours is mixed, the reactant mixture that will be obtained is filtered, after the lower 30 DEG C of filtrates concentrated under reduced pressure of -0.04MPa, at 0 DEG C repeatedly
Target product is obtained after recrystallization, structural formula is：Yield：89%, fusing point：199~201 DEG C.
Embodiment three：A kind of preparation method of the silicon compound of amidino groups containing N proplastid, comprises the following steps：
(1) willIt is dissolved in ether solvent,It is 1 with the mass ratio of ether:20 ,-
53 DEG C be kept stirring under conditions of add lithium methide diethyl ether solution in,It is 1 with the mol ratio of phenyl lithium:
1.2, the concentration of the diethyl ether solution of lithium methide is 2.5M, and mixing speed is 2000 revs/min；Continue to stir anti-after returning to room temperature
Answer 2 hours, obtain reactant mixture；
(2) the reactant mixture filtering for obtaining step (1), collects filter residue, lithium salts solid is obtained, by lithium salts solid and second
Ether mixes, and lithium salts solid is 1 with the mass ratio of ether:15, obtain the diethyl ether solution of lithium salts；
(3) at 30 DEG C according to lithium salts and SiF4Mol ratio 4:1, the diethyl ether solution of lithium salts is added drop-wise to SiF4Diethyl ether solution
In, continue stirring reaction 5 hours at this temperature；
(4) reactant mixture that step (3) is obtained is filtered, after the lower 40 DEG C of filtrates concentrated under reduced pressure of -0.07MPa, -
Vacuum distillation obtains target product under 0.1MPa, and structural formula is：Yield：75%.
Example IV：A kind of preparation method of the silicon compound of amidino groups containing N proplastid, comprises the following steps：
(1) willIt is dissolved in tetrahydrofuran solvent,With the quality of tetrahydrofuran solvent
Than being 1:20, under conditions of being kept stirring at 0 DEG C in the diethyl ether solution of addition phenyl lithium,With rubbing for phenyl lithium
You are than being 1:1.2, the concentration of the diethyl ether solution of phenyl lithium is 2.5M, and mixing speed is 2000 revs/min；Return to room temperature follow-up
Continuous stirring reaction 3 hours, obtains reactant mixture；
(2) the reactant mixture filtering for obtaining step (1), collects filter residue, lithium salts solid is obtained, by lithium salts solid and four
Hydrogen furans mixes, and lithium salts solid is 1 with the mass ratio of ether:15, obtain the tetrahydrofuran solution of lithium salts；
(3) at 34 DEG C according to lithium salts and (CH3)3SiI mol ratios 1:1, the tetrahydrofuran solution of lithium salts is added drop-wise to (CH3)3In the tetrahydrofuran solution of SiI, continue stirring reaction 3 hours at this temperature；
(4) reactant mixture that step (3) is obtained is filtered, after the lower 50 DEG C of filtrates concentrated under reduced pressure of -0.1MPa, -
Vacuum distillation obtains target product under 0.01MPa, and structural formula is：Yield：92%.
The silicon compound of amidine ligand containing N obtained by the present invention can serve as the proplastid of CVD/ALD, by chemical vapor deposition
Product (CVD) or ald (ALD) technique, forms silicon nitride, silicon oxynitride, carborundum, silica, the nitridation of carbon doping
The silicon oxynitride film of silicon, the silica of carbon doping and carbon doping.Described deposition film technique, still more preferably by making
With low-pressure chemical vapor deposition, hot-wire chemical gas-phase deposition, ald, the ald of plasma enhancing, etc. from
The cyclic chemical vapor deposition of the enhanced chemical vapor deposition of daughter and plasma enhancing is carried out.
The present invention has advantages below：(1) simple synthetic method, mild condition greatly reduces the synthesis of preceding material
Cost；(2) in toluene, ether, dichloromethane, tetrahydrofuran has preferable dissolubility in the organic solvent such as n-hexane so that
Transport of materials, conveying, process becomes simple and easy to operate；(3) this proplastid material non-toxic, lively type are moderate, danger coefficient
Substantially reduce；(4) there is a good volatility and heat endurance, such as test by thermogravimetric (TG) method to material thermal property, often
Pressure has following structureProplastid, its T50 be 80 DEG C, minimum residual volume up to 0%, (see Fig. 1)；(5) have
There is good filming performance, still by taking above-mentioned proplastid as an example, with N2/H2Mixed gas is carrier gas, under the conditions of 600 DEG C, can be formed good
Cvd film, the scanning electron microscope (SEM) photograph of prepared film is shown in Fig. 2.
Claims (7)
1. a kind of silicon compound of amidino groups containing N, it is characterised in that its structural formula is：
2. a kind of method for preparing the silicon compound of amidino groups containing N as claimed in claim 1, it is characterized in that, comprise the following steps：
(1) willIt is dissolved in reaction dissolvent,With the quality of reaction dissolvent
Than being 1:10~1:20, phenyl lithium solution is added under conditions of being kept stirring at -78~0 DEG C,With
The mol ratio of phenyl lithium is 1:1~1.2, the concentration of phenyl lithium solution is 1.0~2.5M, and mixing speed is 800~2000 revs/min
Clock；Continue stirring reaction 0.5~3 hour after returning to room temperature, obtain reactant mixture, the reaction dissolvent is n-hexane, first
Benzene, dichloromethane, tetrahydrofuran or ether；
(2) the reactant mixture filtering for obtaining step (1), collects filter cake, obtains lithium salts solid, and lithium salts solid is molten with organic
Agent mixes, and lithium salts solid is 1 with the mass ratio of organic solvent:10~20, obtain lithium salt solution, the reaction dissolvent for just oneself
Alkane, toluene, dichloromethane, tetrahydrofuran or ether；
(3) at -78~0 DEG C according to lithium salts and (CH3)3SiI mol ratios 1~4:1, contain (CH to being added dropwise in above-mentioned lithium salt solution3)3The solution of SiI, is slowly increased to uniform temperature, the temperature be room temperature to the reflux temperature of solvent for use, continue at this temperature
Stirring reaction 3~10 hours；
(4) reactant mixture that step (3) is obtained is filtered, low temperature crystallization or vacuum distillation are obtained after filter vacuum concentration
To the silicon compound of amidino groups containing N；
(5) or after step (3) is stirred 3~10 hours, at -78~0 DEG C, the organic amine of 1~10 molar equivalent is added, is delayed
Slow to rise to uniform temperature, the temperature is reflux temperature of the room temperature to solvent for use, be further continued at this temperature stirring reaction 3~
10 hours, low temperature crystallization or vacuum distillation obtained the described silicon compound of amidino groups containing N after filter vacuum concentration.
3. preparation method as claimed in claim 2, it is characterized in that：In the step (3) and (5), programming rate is 0.5~1
DEG C/min.
4. preparation method as claimed in claim 2, it is characterized in that：The reactant mixture that the step (4) or (5) obtain is carried out
Filtering, after filtrate is concentrated, then carries out low temperature crystallization, or vacuum distillation obtains the described silicon compound of amidino groups containing N；The filter
Liquid concentration condition be：Concentrated under reduced pressure at 20~50 DEG C, concentration or vacuum distillation pressure are -0.1~-0.01MPa.
5. the silicon compound of amidino groups containing N is used as the application of integrated circuit thin-film material proplastid, its feature as claimed in claim 1
It is：By chemical vapor deposition or atom layer deposition process, silicon-containing film is prepared.
6. application as claimed in claim 5, it is characterized in that：The film be using proplastid as claimed in claim 1 with
One or more reactions in ammonia, nitrous oxide, nitric oxide, oxygen, ozone, vapor are obtained.
7. application as claimed in claim 5, it is characterized in that：The film include silicon nitride, containing carbonitride of silicium, silicon oxynitride,
The silicon oxynitride film of carborundum, silica, the silica of carbon doping and carbon doping.
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| TW201509799A (en) | 2013-07-19 | 2015-03-16 | Air Liquide | Hexacoordinate silicon-containing precursors for ALD/CVD silicon-containing film applications |
| US9382268B1 (en) | 2013-07-19 | 2016-07-05 | American Air Liquide, Inc. | Sulfur containing organosilane precursors for ALD/CVD silicon-containing film applications |
| US10570513B2 (en) | 2014-12-13 | 2020-02-25 | American Air Liquide, Inc. | Organosilane precursors for ALD/CVD silicon-containing film applications and methods of using the same |
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| Low-Temperature Polymerization of Olefins in the Presence of Titanium Monoamidinate/MAO Catalyst;Dario Liguori等，;《Macromol. Chem. Phys.》;20031231;第204卷;第164-170页，尤其是第168页左栏第6段以及右栏第3段 * |
| Polymerization of Propene and 1,3-Butadiene with Vanadyl(V) Monoamidinate Precatalysts and MAO or Dialkylaluminum Chloride Cocatalysts;Dario Liguori等，;《Macromol. Chem. Phys.》;20041231;第205卷;第1058–1063页，尤其是第1061页右栏 * |
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