CN101104679A - Aromatic diacid ester acetal polymer, synthetic method and use thereof - Google Patents
Aromatic diacid ester acetal polymer, synthetic method and use thereof Download PDFInfo
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- CN101104679A CN101104679A CNA2007101307784A CN200710130778A CN101104679A CN 101104679 A CN101104679 A CN 101104679A CN A2007101307784 A CNA2007101307784 A CN A2007101307784A CN 200710130778 A CN200710130778 A CN 200710130778A CN 101104679 A CN101104679 A CN 101104679A
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Abstract
The invention relates to various aromatic diacid ester acetal polymers and a synthesis method of the aromatic diacid ester acetal polymers. Various aromatic diacids and various divinyl ether compounds are heated to react in organic solvent to obtain novel ester acetal polymers. The above-mentioned polymers are easy to have acid decomposition reaction. Therefore, the acetal polymers and photoacid generators can be used together to compose a novel positive photographic imaging materials which can be used as photoresist used in super large scale integrated circuit process and can be used as imaging materials for printing PS plate or CTP plate.
Description
Technical field
The technical field of the invention is the macromolecule polymer material field, i.e. novel ester acetal polymer and the synthetic method thereof of a class.Specifically, aromatic diacid and divinyl ether compound react the formation ester acetal polymer under certain condition, and this base polymer is easy to take place acid and causes decomposition reaction, but therefore with light acid producing agent constitutional chemistry amplification type photosensitive imaging material.The novel photosensitive imaging material of this class can be used for super large-scale integration with deep ultraviolet positive photoresist (claiming photoresist material again) and printing with Computer To Plate (CTP) sensitization, induced thermal imaging constituent.
Background technology
The image-forming principle of common photo-resist is that alkali-soluble group such as phenolic hydroxyl group and carboxy protective are got up to become acid decomposable from group, as ester group or acetal.These acid decomposable are decomposed under the light acid production from group, and it is solvable to become alkali again, can carry out the dilute alkaline developing imaging.The class New Photoinduced resist system of having reported in recent years is made up of divinyl ether compound and film-forming resin, these divinyl ether compounds comprise aromatic series and aliphatic divinyl ether, and film-forming resin has resol and contains the polymethacrylate derivative of part carboxyl.By the resist rete that these compounds and light acid producing agent are formed, after preliminary drying, phenolic hydroxyl group in the polymkeric substance or carboxyl and divinyl ether compound generation acetalation form crosslinking structure.Dry by the fire through exposure and back again and separate crosslinking reaction, thereby make exposure region have caustic solubility, can obtain positive light anti-etching agent.In order to obtain having the 193nm photo-resist of the fine transparency, can not contain aromatic ring structure, thereby study morely the multipolymer of methacrylic acid system at 193nm.But in order to strengthen the anti-plasma etching ability of photo-resist rete, multipolymer need be introduced a large amount of alicyclic structures, and this has just increased synthetic difficulty.
Inspired by this, we can become the straight chain type ester acetal polymer by the reaction of diacid and divinyl ether compound at imagination, and this base polymer has sour resolution characteristic, can form positive light anti-etching agent with acidogenic agent etc.Research and selection through to diacid and divinyl ether compound are expected to obtain the novel high-performance deep ultraviolet positive light anti-etching agent of a class.
Aromatic diacid, as phthalic acid, naphthalic acid etc., have characteristics cheap and easy to get, aromatic ring structure makes its polymkeric substance have high intensity and glass transition temperature, has strong anti-plasma etching ability as photo anti-corrosion agent material, experiment shows aromatic diacid energy and the reaction of divinyl ether compound, and these aromatic diacids of primary study of the present invention and the reaction of divinyl ether compound generate ester acetal polymer.
Summary of the invention
On the basis that the reaction of various diacid and divinyl ether compound is studied, we find that aromatic diacid and various divinyl ether compound can react generation straight chain type ester acetal polymer, this base polymer is soluble in various organic solvents commonly used, has higher softening temperature, Heat stability is good, experiment shows that they easily decompose, discharge carboxyl under acid catalysis.Base polymer and light acid producing agent etc. can be formed the new chemical amplification type photosensitive imaging material of dilute alkaline developing together like this, thus.By selecting the light acid producing agent of different wavelength photoreceptor scopes, can be used as super large-scale integration processing such as i line positive photoresist, 248nm (KrF) positive photoresist and electron sensitive resist and use photo-resist, also can be used as the image forming material of printing with high sensitivity PS version, CTP plate etc.
Therefore, one aspect of the present invention provides the aromatic diacid ester acetal polymer shown in a kind of following general formula (I):
R
1Be following group:
R
1Also comprise the group that does not contain aryl, as:
At this moment, m=1, R
0For-CH
2-or do not have group; For another example :-CH
2-, at this moment, m≤4, R
0For :-CH
2-; And for example :-O-, at this moment, m=1, R
0For :-CH
2CH
2-.
R
2Be following various aryl:
R wherein
8-R
11Be H or C independently of one another
NH
2N+1Or OC
NH
2N+1, N≤4, or other substituting group wherein are as F, Cl, NO
2, CN etc.
The present invention provides the method for aromatic diacid ester acetal polymer shown in the above-mentioned general formula of a kind of preparation (I) on the other hand, comprises making aromatic diacid and divinyl ether compound reacting by heating and obtain required ester acetal polymer in the presence of organic solvent.
Detailed Description Of The Invention
In the methods of the invention, the used general available following formula of divinyl ether compound (II) is represented:
(CH
2＝CHOR
0
2R
1)
m
(II)
R wherein
1, m, R
0Suc as formula defining in (I).
Preferred divinyl ether compound is: 1, and 4-divinyl oxide ylmethyl hexanaphthene, 1,4-divinyl oxide basic ring hexane, 1,2-divinyl oxide base ethane, 1,3-divinyl oxide base propane, divinyl oxide benzyl ethyl ether etc. can be bought the commercially available prod or prepare by literature method.
Preferred divinyl ether compound also comprises: 1,4-divinyl oxide base oxethyl benzene, 1,3-divinyl oxide base oxethyl benzene, 1,2-divinyl oxide base oxethyl benzene, 2, various divinyl ether compounds such as 2-two (4,4 '-divinyl oxide base oxethyl) phenyl-propane.
The above divinyl ether compound that is used for the present invention can be according to literature method (J.V.Crivello and D.A.Conlon, Aromatic Bisvinyl Ethers:A New Class of Highly ReactiveThermosetting Monomers, Journal of Polymer Science:PolymerChemistry Edition, V21,1785-1799 (1983) is by various dihydric phenols compounds, as Resorcinol, Resorcinol, pyrocatechol, dihydroxyphenyl propanes etc. and chloroethyl vinyl ether are in the presence of highly basic, with the methyl-sulphoxide is solvent, and reacting by heating obtains.This reaction is carried out than being easier to, and productive rate is higher.In addition, also available phenolic group acid, reaction obtains the used divinyl ether compound of the present invention with the chloroethyl vinyl ether as P-hydroxybenzoic acid, m-Salicylic acid, salicylic acid etc., but this reaction yield is low slightly.Reaction is shown below:
R wherein
1Suc as formula defining in (I).
In above-mentioned reaction, dihydric phenols compound elder generation and excessive highly basic reaction generation phenates, again with excessive chloroethyl vinyl ether react target product divinyl ether compound, reactant molar ratio dihydric phenol: highly basic: the chloroethyl vinyl ether is 1: 2.5～3.5: 2～4.The consumption of solvent is the 50-80% of reactant total mass.Heating temperature is 80-100 ℃.
Perhaps can also be by the diprotic acid compounds, reaction obtains the used divinyl ether compound of the present invention with the chloroethyl vinyl ether as terephthalic acid, m-phthalic acid, phthalic acid, oxalic acid, hexanodioic acid etc.But this reaction yield is lower, and experiment finds that also the softening temperature of its final polymerisate of divinyl ether compound of being made by fat diacids such as oxalic acid, hexanodioic acids is lower, and is not high as the practical value of the composition of resist.
At last, other some divinyl ether compounds also can react, as document (H.Sachdev, R.Kwong, W.Huang, New Negative Tone Resists for Sub-quarter MicronLithography, Microelectronic Engineering 27 (1995), two dihydropyran derivatives shown in the following formula that 393-396) provides:
In the methods of the invention, the used general available following formula of aromatic diacid (III) is represented:
HOOC——R
2-COOH
(III)
R wherein
2Suc as formula defining in (I).From convenient, economic angle, preferred aromatic diacid is the various substituent commercial goods aromatic diacids that do not contain.Part contains substituent phthalic acid and can use the commercial goods, and the suitable organic reaction of passing through of no commercial goods prepares.Anthracene dioctyl phthalate and contain substituent naphthalic acid and also can react, but these compounds are more expensive, not as preferred raw material.
Aromatic diacid and divinyl ether compound reacting by heating in the presence of organic solvent can obtain the aromatic diacid ester acetal polymer shown in a series of above-mentioned general formulas (I).Reacting used organic solvent is non-polar solvents such as weak polar solvents such as pimelinketone, dioxane or dimethylbenzene.Intensive polar solvent such as ethylene glycol ethyl ether, methyl-sulphoxide, N, dinethylformamide etc. cause reacting that difficulty is carried out, extent of polymerization is low even cause side reaction to take place.Aromatic diacid is insoluble in non-polar solvents such as dimethylbenzene under many circumstances, makes reaction be difficult to carry out or to carry out ground very slow.If the aromatic diacid of selecting for use has certain dissolubility in dimethylbenzene, then available dimethylbenzene is made solvent.Solvent can use with the amount of 25-75 weight % based on the reaction system total amount.Too little solvent then aromatic diacid is dissolved fewly, and speed of response is slow.Solvent reactant concn at most is low, can reduce speed of response and cause waste.The reaction Heating temperature is 100-160 ℃, preferred 120-140 ℃.Temperature is low, and then speed of response is slow, and temperature is too high then may to cause side reaction to take place.The reaction mol ratio of raw material aromatic diacid and divinyl ether compound was generally 1: 1, and perhaps in the diacid excessive slightly 5%, if two excessive acids are too many, the alkali-resistivity of resulting polymers is poor, and it is bad to be used for the resist effect.Reaction process can detect with infrared spectra, along with reaction is carried out, and visible 3400cm
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Under preferred reaction conditions, along with the reactant difference, reaction can be finished in 3-48 hour.Obtain ester acetal polymer product solution.This product solution can directly use, and also this product solution can be poured in an amount of sherwood oil, separates out solid, and drying or vacuum-drying get solid product.
Experiment shows that ester acetal polymer of the present invention decomposing rapidly under a small amount of strong acid catalysis, discharges carboxyl under room temperature or heating, and insoluble to become alkali molten by alkali.Therefore, can form new chemical amplification type positive photoresist together by this class ester acetal polymer and light acid producing agent etc.
Embodiment
The present invention is described in detail by the following example, but these embodiment do not limit the scope of the invention.
Embodiment 11,4-naphthalic acid and 1,4-divinyl oxide ylmethyl hexanaphthene (cyclohexyl dimethanol divinyl ether) reaction
In having the 250ml four-hole bottle of mechanical stirring, thermometer, prolong, add 21.6g (0.1mol) 1,4-naphthalene diacid and 19.6g (0.1mol) 1,4-divinyl oxide ylmethyl hexanaphthene (cyclohexyl dimethyl divinyl ether), add 41ml1, the 4-dioxane, heated and stirred is warming up to 120 ℃-130 ℃, and stirring reaction finished in 3 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 2M-phthalic acid and 1,4-divinyl oxide ylmethyl hexanaphthene (cyclohexyl dimethanol divinyl ether) reaction
In having the 250ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) m-phthalic acid and 19.6g (0.1mol) 1,4-divinyl oxide ylmethyl hexanaphthene (cyclohexyl dimethyl divinyl ether), add 36ml1, the 4-dioxane, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 3 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 3Terephthalic acid and 1,4-divinyl oxide ylmethyl hexanaphthene (cyclohexyl dimethanol divinyl ether) reaction
In having the 250ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) terephthalic acid and 19.6g (0.1mol) 1,4-divinyl oxide ylmethyl hexanaphthene (cyclohexyl dimethyl divinyl ether), add 36ml1, the 4-dioxane, heated and stirred, be warming up to 120～130 ℃, stirring reaction finished in 24 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 4M-phthalic acid and 2,2-two (4,4 '-divinyl oxide base oxethyl) phenyl-propane (dihydroxyphenyl propane divinyl oxide benzyl ethyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) m-phthalic acid and 36.8g (0.1mol) 2,2-two (4,4 '-divinyl oxide base oxethyl) phenyl-propane (dihydroxyphenyl propane divinyl oxide benzyl ethyl ether), add the 55ml pimelinketone, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 6 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 5M-phthalic acid and 1,4-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) m-phthalic acid and 25.1g (0.1mol) 1,4-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether), add the 42ml pimelinketone, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 5 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 6M-phthalic acid and 1,3-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) m-phthalic acid and 25.1g (0.1mol) 1,3-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether), add the 42ml pimelinketone, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 6 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 7Terephthalic acid and 1,3-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) terephthalic acid and 25.1g (0.1mol) 1,3-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether), add the 84ml dioxane, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 24 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 81,4-naphthalic acid and 1,4-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 21.6g (0.1mol) 1,4-naphthalic acid and 25.1g (0.1mol) 1,4-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether), add 90ml dimethylbenzene, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 6 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 91,4-naphthalic acid and 1,3-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 21.6g (0.1mol) 1,4-naphthalic acid and 25.1g (0.1mol) 1,3-divinyl oxide base oxethyl benzene (Resorcinol divinyl oxide benzyl ethyl ether), add the 90ml pimelinketone, heated and stirred, be warming up to 120 ℃-130 ℃, stirring reaction finished in 8 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Embodiment 10M-phthalic acid and 1,2-divinyl oxide base ethane reaction (ethylene glycol bisthioglycolate vinyl ether) reaction
In having the 500ml four-hole bottle of mechanical stirring, thermometer, prolong, add 16.6g (0.1mol) m-phthalic acid and 11.4g (0.1mol) 1,2-divinyl oxide base ethane reaction (ethylene glycol bisthioglycolate vinyl ether) adds the 60ml pimelinketone, heated and stirred, be warming up to 120-125 ℃, stirring reaction finished in 5 hours.
Product is measured the visible 3400cm of infrared spectra
-1Near the absorption of carboxylic acid disappears 1690cm substantially
-1Near the carbonyl absorption of carboxylic acid disappears, 1720cm
-1Near the carbonyl absorption of ester group appears.Show to react and finish.
Claims (10)
1. the aromatic diacid ester acetal polymer shown in the following general formula (I):
R
1Be following group:
Deng, R wherein
3-R
6Be H or C independently of one another
NH
2N+1, N≤4 wherein; And R
7Be C
NH
2N+1Or C
6H
5, N≤4 wherein.At this moment, m=1, R
0For:---CH
2CH
2O---, wherein oxygen and R
1Link to each other.R
1Also comprise the group that does not contain aryl, as:
, at this moment, m=1, R
0For :-CH
2-or do not have group; For another example :-CH
2-, at this moment, m≤4, R
0For :-CH
2-; And for example :-O-,
At this moment, m=1, R
0For :-CH
2CH
2-.
R
2Be following various aryl:
R wherein
8-R
11Be H or C independently of one another
NH
2N+1Or OC
NH
2N+1, N≤4, or other substituting group wherein are as F, Cl, NO
2, CN etc.
2. method for preparing the described polymkeric substance of claim 1 comprises making the reacting by heating and obtaining in the presence of organic solvent of the divinyl ether compound shown in aromatic diacid and the following formula (II):
(CH
2＝CHOR
0
2R
1)
m
(II)
R wherein
1, R
0, m such as claim 1 definition.
3. method as claimed in claim 2, the general available following formula of wherein used aromatic diacid (III) expression:
HOOC-R
2-COOH
(II)
R wherein
2Such as claim 1 definition.
4. method as claimed in claim 2, wherein used divinyl ether compound comprises: 1,4-divinyl oxide ylmethyl hexanaphthene, 1,4-divinyl oxide basic ring hexane, 1,2-divinyl oxide base ethane, 1,3-divinyl oxide base propane, divinyl oxide benzyl ethyl ether, 1,4-divinyl oxide base oxethyl benzene, 1,3-divinyl oxide base oxethyl benzene, 1,2-divinyl oxide base oxethyl benzene, 2,2-two (4,4 '-divinyl oxide base oxethyl) phenyl-propane.
5. method as claimed in claim 2, wherein said solvent are non-polar solvents such as weak polar solvents such as dioxane, pimelinketone or dimethylbenzene.
6. method as claimed in claim 5, the consumption of solvent is 25-75 weight % based on the reaction system total amount.
7. method as claimed in claim 2, wherein said Heating temperature are 100-160 ℃.
8. method as claimed in claim 6, wherein said Heating temperature are that 120-140 ℃ and reaction times are 3-48 hour.
9. method as claimed in claim 2, wherein the mol ratio of diacid and divinyl ether compound is 1-1.1: 1.
10. method as claimed in claim 8, wherein the mol ratio of diacid and divinyl ether compound is 1-1.05: 1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101812173A (en) * | 2009-11-05 | 2010-08-25 | 北京师范大学 | N-hydroxy maleopimaric acid imide ester acetal polymer and preparation method thereof |
| CN101891888A (en) * | 2010-08-20 | 2010-11-24 | 太原工业学院 | Diphenol divinyl ether acetal polymer and preparation method thereof |
| CN104181775A (en) * | 2014-08-18 | 2014-12-03 | 邯郸开发区立业化工有限公司 | Chemically amplified i-line positive photoresist composition containing diphenol acetal polymer |
-
2007
- 2007-07-24 CN CNA2007101307784A patent/CN101104679A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101812173A (en) * | 2009-11-05 | 2010-08-25 | 北京师范大学 | N-hydroxy maleopimaric acid imide ester acetal polymer and preparation method thereof |
| CN101812173B (en) * | 2009-11-05 | 2014-01-29 | 北京师范大学 | N-hydroxy maleopimaric acid imide ester acetal polymer and preparation method thereof |
| CN101891888A (en) * | 2010-08-20 | 2010-11-24 | 太原工业学院 | Diphenol divinyl ether acetal polymer and preparation method thereof |
| CN104181775A (en) * | 2014-08-18 | 2014-12-03 | 邯郸开发区立业化工有限公司 | Chemically amplified i-line positive photoresist composition containing diphenol acetal polymer |
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Open date: 20080116 |