CN1850783A - Constitutive photo-sensitive diethylenetriamine, and its preparing method - Google Patents
Constitutive photo-sensitive diethylenetriamine, and its preparing method Download PDFInfo
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- CN1850783A CN1850783A CN 200610020874 CN200610020874A CN1850783A CN 1850783 A CN1850783 A CN 1850783A CN 200610020874 CN200610020874 CN 200610020874 CN 200610020874 A CN200610020874 A CN 200610020874A CN 1850783 A CN1850783 A CN 1850783A
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Abstract
This invention relates to structural photosensitive diamine and its preparation method, and it belongs to photosensitivity micro molecule functional material in material technique field. The structural style photosensitive diamine main component structure formula is H2N-R-R'-R-NH2, R' is acryloyl and substitution acryloyl, R is ortho position aryl group that contains alkyl, alkoxyl or sulfhydryl. The preparation method is that amino group ortho position alkyl aromatic ketone contains alpha hydrogen is condensed with amino group ortho position alkyl aromatic aldehyde, and then they are separated and filtrated to get the product. The product in this invention has higher density photosensitive active basal group, these groups can match exposure wave length at the same time to make photosensitivity greatly improved, and it can be used to prepare high photosensitive and resolution photosensitive polyimide material. The preparation method is simple and control is easy.
Description
Technical field
A kind of constitutive photo-sensitive diethylenetriamine and preparation method thereof belongs to the photosensitivity small molecules functional materials in the material technology field, can be used for synthesizing in light-sensitive polyimide (PSPI) material of making the photoresist material important component in microelectronics, photoelectron technology field.
Background technology
The thermostability of PSPI collection excellence, favorable mechanical, electric, chemical property and photosensitive property are in one, extensively be used in all respects such as ray shield layer material, insulating layer material, cushioning layer material, flat bed material, liquid crystal aligning layer material, nonlinear optical material, optical waveguide material, ion implantation mask, high temperature resistant gas-liquid separation membrane, flexible printed circuit, micro mechanical system, particularly in the fields such as microelectronics, space flight and aviation, photoelectron, shown great application prospect.Structure-type PSPI is because photosensitive group is positioned on the high molecular main chain, and overcome ester type, the existing shortcoming of ionic PSPI: can slough a large amount of molecules in the imidization technological process, it is higher to make film forming shrinking percentage, has limited the raising of graphics resolution greatly.Though self-sensitizing type PSPI has overcome the problem of film-remaining ratio, but exist the low shortcoming of lightsensitivity [M.K.Ghosh ﹠amp; K.L.MittalEd.Polymides, Marcel Dekker, 1996].Therefore, the structure-type PSPI of tool application prospect of far-reaching significance among the research and development PSPI.For example: contain the unitary structure-type PSPI of cinnamophenone (Journal of PolymerScience:Part A:Polymer Chemistry on people such as the K.Feng institute synthetic main chain, 1998, Vol.36,685), its resolving power is higher, but the sensitivity to light is not high, and this mainly is because due to the photo-sensitive diethylenetriamine of synthesizing chalcone structure.For this reason, prepare the key point that novel photo-sensitive diethylenetriamine becomes this type of PSPI material of development.
Summary of the invention
The object of the invention is to provide a kind of constitutive photo-sensitive diethylenetriamine and preparation method thereof.Constitutive photo-sensitive diethylenetriamine provided by the invention contains two kinds the photosensitive active basal group of photo-crosslinking or the photosensitive active basal group of higher density can take place, thereby has highly sensitive characteristics in its molecular structure.
A kind of constitutive photo-sensitive diethylenetriamine is characterized in that, the chemical structural formula of its main component is:
H
2N-R-R′-R-NH
2
Wherein R ' is acryl or substituted acryl, and its chemical expression is:
R is the aryl that the ortho position contains alkyl, alkoxyl group or sulfydryl, and its chemical expression can be:
A kind of preparation method of constitutive photo-sensitive diethylenetriamine may further comprise the steps:
Step 1. is dissolved in the aromatic aldehyde that an amount of amino ortho position contains alkyl in the organic solvent, and making its concentration is 0.1-1mol/L;
Step 2. slowly is added drop-wise to the aromatic aldehyde organic solution of step 1. gained in the mixed solution of aromatic ketone, organic solvent and inorganic base aqueous solution of equimolar amount, at 0 ℃ of abundant stirring reaction down;
Use organic solvent washing behind the reactant suction filtration of step 3. with step 3., repeated multiple times suction filtration, washing;
Step 4. recrystallization is purified, and vacuum-drying under 50 ℃ of-60 ℃ of conditions finally obtains target product then.
The organic solvent that uses in described step 1 and the step 2 can be ethanol, methyl alcohol, propyl alcohol or Virahol.
The mineral alkali that uses in the described step 2 can be sodium hydroxide, potassium hydroxide, salt of wormwood or yellow soda ash, and its concentration of aqueous solution is 5-10wt%.
The principle that the present invention prepares described constitutive photo-sensitive diethylenetriamine can be expressed as:
Wherein R ' is for being acryl and substituted acryl, and its chemical expression is:
R is the aryl that the ortho position contains alkyl, alkoxyl group or sulfydryl, and its chemical expression can be:
Constitutive photo-sensitive diethylenetriamine of the present invention owing to contain two kinds of photosensitive active basal groups that photo-crosslinking can take place in its molecular structure, has improved the density of photosensitive active basal group; These photosensitive groups all can be complementary with exposure wavelength simultaneously, thereby make photosensitivity be greatly enhanced, and have improved the shortcoming of the sensitivity difference of the present structure-type PSPI existence of studying.The prepared PSPI of this photo-sensitive diethylenetriamine is again the structure-type photochromics, and the shrinking percentage of photoetching formation caudacoria is minimum, is fit to process of industrialization.So possessing the corresponding PSPI that is obtained by constitutive photo-sensitive diethylenetriamine of highly sensitive and high film-remaining ratio characteristics will have a wide range of applications in fields such as microelectronics industry, optoelectronics industry, space flight and aviation industry.
Description of drawings
Fig. 1 is preparation method's schematic flow sheet of constitutive photo-sensitive diethylenetriamine of the present invention.
Embodiment
In the three-necked bottle of 50mL with 3 of 0.02mol, 3 '-diethyl-4-aminobenzaldehyde is dissolved in the ethanol of 20mL, be added drop-wise to 0.02mol 2, in the mixed solution of 4-diethyl-3-aminoacetophenone, 20mL ethanol, the 10mL 4wt%NaOH aqueous solution, stir 3h under ice bath, suction filtration is used washing with alcohol, repeated multiple times carries out obtaining 2.95 gram target products behind the recrystallization.
After tested: above-mentioned target product sensitivity is 80～135mJ/cm
2, film-remaining ratio is 80%～90%, the highest decomposition temperature is 483 ℃, presents characteristics such as highly sensitive, high film-remaining ratio and high heat resisting temperature.
Claims (4)
1, a kind of constitutive photo-sensitive diethylenetriamine is characterized in that, the chemical structural formula of its main component is:
H
2N-R-R′-R-NH
2
Wherein R ' is acryl or substituted acryl, and its chemical expression is:
R is the aryl that the ortho position contains alkyl, alkoxyl group or sulfydryl, and its chemical expression can be:
2, a kind of preparation method of constitutive photo-sensitive diethylenetriamine is characterized in that, may further comprise the steps:
Step 1. is dissolved in the aromatic aldehyde that an amount of amino ortho position contains alkyl in the organic solvent, and making its concentration is 0.1-1mol/L;
Step 2. slowly is added drop-wise to the aromatic aldehyde organic solution of step 1. gained in the mixed solution of aromatic ketone, organic solvent and inorganic base aqueous solution of equimolar amount, at 0 ℃ of abundant stirring reaction down;
Use organic solvent washing behind the reactant suction filtration of step 3. with step 3., repeated multiple times suction filtration, washing;
Step 4. recrystallization is purified, and vacuum-drying under 50 ℃ of-60 ℃ of conditions finally obtains target product then.
3, the preparation method of a kind of constitutive photo-sensitive diethylenetriamine according to claim 2 is characterized in that, the organic solvent that uses in described step 1 and the step 2 can be ethanol, methyl alcohol, propyl alcohol or Virahol.
4, the preparation method of a kind of constitutive photo-sensitive diethylenetriamine according to claim 2 is characterized in that, the mineral alkali that uses in the described step 2 can be sodium hydroxide, potassium hydroxide, salt of wormwood or yellow soda ash, and its concentration of aqueous solution is 5-10wt%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200610020874 CN1850783A (en) | 2006-05-23 | 2006-05-23 | Constitutive photo-sensitive diethylenetriamine, and its preparing method |
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| CN 200610020874 CN1850783A (en) | 2006-05-23 | 2006-05-23 | Constitutive photo-sensitive diethylenetriamine, and its preparing method |
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| CN1850783A true CN1850783A (en) | 2006-10-25 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229333A (en) * | 2019-06-25 | 2019-09-13 | 湘潭大学 | A kind of synthetic method of new type polyimide |
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2006
- 2006-05-23 CN CN 200610020874 patent/CN1850783A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229333A (en) * | 2019-06-25 | 2019-09-13 | 湘潭大学 | A kind of synthetic method of new type polyimide |
| CN110229333B (en) * | 2019-06-25 | 2022-02-15 | 湘潭大学 | Synthetic method of polyimide |
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