CN109765755A - A kind of photoresist and preparation method thereof - Google Patents
A kind of photoresist and preparation method thereof Download PDFInfo
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- CN109765755A CN109765755A CN201910072883.XA CN201910072883A CN109765755A CN 109765755 A CN109765755 A CN 109765755A CN 201910072883 A CN201910072883 A CN 201910072883A CN 109765755 A CN109765755 A CN 109765755A
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Abstract
The present invention provides a kind of photoresist, and raw material includes main body, modified monomer and substrate monomer, by addition catalyst and carries out obtaining photoresist under copolyreaction；The structural formula of the photoresist are as follows:
Description
Technical field
The present invention relates to a kind of semiconductor optoelectronic display material fields, more particularly, to a kind of light for having self-healing performance
Photoresist material.
Background technique
General material can inevitably generate scraping in use, and the external force damage such as friction greatly shortens the use of material
Service life causes huge material resources wave so the Other substrate materials formed for covalent cross-linking are difficult to recycle again
Take, and environment and the energy are caused stress.
Realize that self-healing introduces noncovalent interaction power and constructs supramolecular materials by supramolecular chemistry.These effects are advocated
It include: hydrogen bond, metal is coordinated, and π-π is stacked, and electrostatic interaction, the methods of host-guest interaction devises many types
Self-healing material.
The method for preparing the material for having self-healing performance, which mainly has, directly to be added and fabricated in situ (two methods.First
The problems such as kind method easily causes inorganic particulate to reunite, particle is lost, and influence the performance of material；Although second method can be with
Particle aggregation is solved the problem of to a certain extent but there are still particle flux mistakes.Other substrate materials are applied to substrate list
The surface of body, directly contacts with nozzle, it is easy to cause mechanical damage and reduce yield, if Other substrate materials have self-healing
Function, on the one hand can greatly prolong the active time of photoresist rubberized material, on the other hand also reduce in photoresist gluing
Maintenance cost in use, it is most important that being capable of the better autonomous possibility for carrying out healing and increasing production yield
Property.And current Other substrate materials do not have self-healing function.
Summary of the invention
The object of the present invention is to provide a kind of photoresists and preparation method thereof, can efficiently solve photoresist and not have
The problem of standby self-healing capability.
In order to solve the above technical problems, the present invention provides a kind of photoresist, raw material includes: host molecule, modified monomer
And substrate monomer；The host molecule is poly cyclodextrin；
The molecular structural formula of the modified monomer are as follows:
The structural formula of the substrate monomer are as follows:
The structural formula of the photoresist are as follows:
Further, the modified monomer is by the first monomeric compound and second comonomer compound synthesis, wherein described
The structural formula of first monomeric compound are as follows:
The structural formula of the second comonomer compound are as follows:
Another object of the present invention provides a kind of preparation method of photoresist, including, provider's molecule, modified monomer, base
Bill kept on file body and catalyst；By being reacted the host molecule to obtain assembly with modified monomer；By the assembly
With the substrate monomer copolyreaction under the action of catalyst, photoresist is obtained.
Further, further include provider's molecular steps: cyclodextrin being added to dissolution in the first solvent and obtains first
Mixed solution；The second solvent is added to first mixed solution and obtains the second mixed solution；Quickly stir second mixing
Solution simultaneously adds third solvent and obtains stopping reaction after third mixed solution；Third mixed solution described in rotary evaporation removes acetone
After obtain the 4th mixed solution；4th mixed solution is dissolved in the water of no ion and obtains the 5th mixed solution；By
Four solvents are added in the 5th mixed solution and obtain the 6th mixed solution；6th mixed solution is dialysed, and is passed through
Isolated host molecule material is lyophilized.
Further, in modified monomer step is provided, comprising: adamantanecarboxylic acid is added to the 5th solvent and obtains the 7th
Mixed solution；It stirs the 7th mixed solution and rotates and obtain the 8th mixed solution；It is added in the 8th mixed solution
Adamantane group and the metering system in the 6th solvent with hydroxyethyl methacrylate, in the 8th mixed solution
Sour hydroxyl ethyl ester obtains the first monomer-polymer, and the structural formula of first monomer-polymer is
Second comonomer polymer is added in first monomer-polymer and forms the 9th mixed solution；Described
The structural formula of two monomeric compounds are as follows:
Stir it is described 9th mixing after solution left standstill, filter obtain modified monomer solution.
Further, in obtaining assembly step, comprising: obtain the host molecule ultrasonic disperse into distilled water
Tenth mixed solution；The modified monomer solution is added in the tenth mixed solution；After being stirred at room temperature 24 hours, freeze
Powdered assembly is obtained after dry.
Further, it, with the substrate monomer under the action of catalyst copolyreaction step, is wrapped by the assembly
It includes: the assembly being dissolved in the 7th solvent and obtains the 11st mixed solution；By hydroxyethyl methacrylate and acrylic acid
Butyl ester is chemically reacted to obtain substrate monomer；By the substrate monomer and catalyst be added in the 11st mixed solution into
Row chemical reaction, can be obtained the photoresist.
Further, first solvent is sodium hydroxide；Second solvent is epoxychloropropane；The third solvent
For acetone；4th solvent is hydrochloric acid.
Further, the 5th solvent is thionyl chloride；6th solvent is hydroxyethyl methacrylate；Described
Two monomeric compounds are diazido naphthoquinone derivative, and the hydroxyethyl methacrylate rubs with the diazido naphthoquinone derivative
You are than being 15:45~15:23.
Further, the 7th solvent includes polyethylene glycol methacrylate-styrene polymer, propylene glycol monomethyl ether, ethylene glycol ethyl ether vinegar
Acid esters and ethyl lactate, the polyethylene glycol methacrylate-styrene polymer, the propylene glycol monomethyl ether, the ethylene glycol ether acetate
And the ethyl lactate volume ratio is 1:1:1:1~3:6:9:8；The substrate monomer and catalyst are being added the described tenth
In the step of being chemically reacted in one mixed solution, the catalyst is azodiisobutyronitrile；The reaction of the chemical reaction
Temperature is 40~60 DEG C, when reaction a length of 12h.
The beneficial effects of the present invention are: the present invention proposes a kind of photoresist and preparation method thereof, by preparing poly ring paste
Essence is used as host molecule, recycles modified object to be included, is finally copolymerized to obtain photoetching of the invention with substrate monomer
Glue material, the Other substrate materials have outstanding self-healing and ability.
Detailed description of the invention
The invention will be further described with reference to the accompanying drawings and examples.
Fig. 1 is the three-dimensional molecular structure schematic diagram of photoresist of the present invention；
Fig. 2 is the equation of the chemical reaction of host molecule of the present invention；
Schematic diagram before photoresist heals under the microscope of the present invention of the position Fig. 3；
Schematic diagram after photoresist healing under the microscope of the present invention of the position Fig. 4.
Specific embodiment
The explanation for being below each embodiment is can to use the specific reality implemented to illustrate the present invention with reference to additional schema
Apply example.The direction term that the present invention is previously mentioned, for example, above and below, front, rear, left and right, inside and outside, side etc., be only with reference to accompanying drawings
Direction.The element title that the present invention mentions, such as first, second etc., it is only to discriminate between different components, it can better table
It reaches.The similar unit of structure is given the same reference numerals in the figure.
Herein with reference to the accompanying drawings to detailed description of the present invention embodiment.The present invention can show as many different forms,
The present invention should not be only interpreted as specific embodiment set forth herein.It is to explain the present invention that the present invention, which provides these embodiments,
Practical application, to make others skilled in the art it will be appreciated that various embodiments of the present invention and being suitable for specific expection
The various modifications scheme of application.
In the description of the present invention, it should be noted that unless otherwise clearly defined and limited, term " installation ", " phase
Even ", " connection " shall be understood in a broad sense, for example, it may be being fixedly connected, may be a detachable connection, or be integrally connected；It can
To be mechanical connection, it is also possible to be electrically connected；It can be directly connected, can also can be indirectly connected through an intermediary
Connection inside two elements.For the ordinary skill in the art, above-mentioned term can be understood at this with concrete condition
Concrete meaning in invention.
As shown in Figure 1, the present invention provides a kind of photoresist, raw material includes: host molecule, modified monomer and substrate list
Body；The host molecule is poly cyclodextrin；
The molecular structural formula of the modified monomer are as follows:
The structural formula of the substrate monomer are as follows:
The structural formula of the photoresist are as follows:
The modified monomer is by the first monomeric compound and second comonomer compound synthesis, wherein first monomer
The structural formula of compound are as follows:
The structural formula of the second comonomer compound are as follows:
The present invention provides a kind of photoresists, by be copolymerized host molecule, modified monomer and substrate monomer
To photoresist of the invention, the photoresist has outstanding self-healing capability.
Another object of the present invention provides a kind of preparation method of photoresist, includes the following steps:
The cyclodextrin (0.88mmol) of 10g is added in the first solvent dissolution and obtains the by S1, host molecule preparation step
One mixed solution；First solvent is sodium hydroxide；The mass percent of first solvent is 33-40%, optimal to be
35%, or 34%, 36% or 38%；The volume of the sodium hydroxide is 16-30mL, and optimal is 25ml, or
18ml, 20ml, 23ml or 28ml.
The second solvent is added after first mixed solution is cooled to 30 DEG C and obtains the second mixed solution；Described second is molten
Agent is 6.89mL epoxychloropropane.
It quickly stirs second mixed solution and adds after third solvent obtains third mixed solution and stop reaction；Stirring
500~700rpm of revolving speed, optimal is 600rpm, or 550rpm, 650rpm or 680rpm；A length of 2~5h when stirring, most
Excellent is 4h, or 3h or 4.5h；The third solvent is acetone, and the dosage of the acetone is 150mL；Pass through rotary evaporation
The third mixed solution obtains the 4th mixed solution after removing acetone.
4th mixed solution is dissolved in the water of no ion and obtains the 5th mixed solution, and the 4th solvent is added
The 6th mixed solution is obtained into the 5th mixed solution；4th solvent is hydrochloric acid, mainly passes through the 4th solvent
The 5th mixed solution pH value adjustment will be obtained to 10~12.
6th mixed solution is dialysed, host molecule amount retains 3000-12000, i.e. separable by freeze-drying later
Host molecule is obtained, the molecular structure structural formula of single cyclodextrin in the structural formula of the host molecule are as follows:
It is more polymeric cyclodextrins as shown in Fig. 2, passing through molecule based on the obtained product of chemical equation,
Cyclodextrin is that a kind of exocoel of peviform is hydrophilic and the hydrophobic molecule in inner cavity, polymerize it with epoxychloropropane to be formed so herein
The structure of polymeric cyclodextrins more than one.
Adamantanecarboxylic acid is added to the 5th solvent and obtains the 7th mixed solution by S2, modified monomer preparation step；The gold
The molal weight of rigid alkane formic acid is 25~102mmol, and optimal is 60mmol, or 30mmol, 40mmol, 70mmol or
90mmol；5th solvent is thionyl chloride, and the thionyl chloride volume is 30~40ml, and optimal is 35ml.
It stirs the 7th mixed solution and rotates the excessive thionyl chloride of removing and obtain the 8th mixed solution；The stirring
The temperature of 7th mixed solution is 80 DEG C, and the time of the 7th mixed solution of the stirring is 2~4h, and the 8th mixed solution is
Adamantane formyl chloride, molecular structural formula are as follows:
It is added in the 8th mixed solution in the 6th solvent (2g, 15mmol) with hydroxyethyl methacrylate,
The adamantane formyl chloride and the hydroxyethyl methacrylate obtain the first monomer-polymer, first monomer-polymer
Structural formula is
Second comonomer polymer is added in first monomer-polymer and forms the 9th mixed solution；Described
The structural formula of two monomeric compounds are as follows:
The diazido naphthoquinone derivative is chemically reacted with the adamantane formyl chloride, forms first singulation
Close object.The molar ratio of the hydroxyethyl methacrylate and the diazido naphthoquinone derivative is 15:45~15:23；Described two
Nitrine naphthoquinone derivatives molal weight is 23~45mmol, and optimal is 35mmol.
It is stood after stirring the 9th mixed solution, filters and obtain modified monomer, the 9th mixed solution time of the stirring
For 5h, the structural formula of the modified monomer are as follows:
S3, assembling preparation step, obtain the into distilled water for the host molecule ultrasonic disperse containing cyclodextrin
Then the modified monomer solution is added in the tenth mixed solution in ten mixed solutions；The quality of the main body be 100~
600mg, the modified monomer quality are 10mg.
Assembly powder can be obtained after being stirred at room temperature 24 hours, after freeze-drying.
The assembly powder is dissolved in the 7th solvent and obtains the 11st mixed solution by S4, photoresist preparation step；
7th solvent includes polyethylene glycol methacrylate-styrene polymer, propylene glycol monomethyl ether, ethylene glycol ether acetate and ethyl lactate,
The polyethylene glycol methacrylate-styrene polymer, the propylene glycol monomethyl ether, the ethylene glycol ether acetate and the ethyl lactate
Volume ratio is 1:1:1:1~3:6:9:8.
It is chemically reacted hydroxyethyl methacrylate and butyl acrylate to obtain substrate monomer；The methacrylic acid
Hydroxyl ethyl ester volume is 1~1.4mL, and the butyl acrylate volume is 1.2~2.9ml.The substrate monomer are as follows:
Substrate monomer is added in the 11st mixed solution and catalyst is chemically reacted, can be obtained described
Photoresist.The catalyst is azodiisobutyronitrile, and the catalyst quality is 5~10mg；The reaction temperature of the chemical reaction
Degree is 40~60 DEG C, when reaction a length of 12h.
Another object of the present invention provides the preparation method of photoresist, by preparing polycyclic dextrin as host molecule, benefit
It is included with modified object, is finally copolymerized to obtain Other substrate materials of the invention, the photoetching glue material with substrate monomer
Material has stronger self-healing ability.
If the healing of Fig. 3 and 4 front and back compares, under the microscope, the healing of the photoresist region of the region of fracture 10 slowly,
This also demonstrates the feasibility of the self-healing ability of photoresist of the invention.
It should be pointed out that can also have the embodiment of a variety of transformation and remodeling for the present invention through absolutely proving,
It is not limited to the specific embodiment of above embodiment.Above-described embodiment is as just explanation of the invention, rather than to hair
Bright limitation.In short, protection scope of the present invention should include that those are obvious to those skilled in the art
Transformation or substitution and remodeling.
Claims (10)
1. a kind of photoresist, which is characterized in that its raw material includes
Host molecule, modified monomer and substrate monomer；
The host molecule is poly cyclodextrin；
The molecular structural formula of the modified monomer are as follows:
The structural formula of the substrate monomer are as follows:
The structural formula of the photoresist are as follows:
2. photoresist according to claim 1, which is characterized in that the modified monomer is by the first monomeric compound and
The synthesis of two monomeric compounds, wherein
The structural formula of first monomeric compound are as follows:
The structural formula of the second comonomer compound are as follows:
3. a kind of preparation method of photoresist, which is characterized in that including,
Provider's molecule, modified monomer, substrate monomer and catalyst；
By being reacted the host molecule to obtain assembly with modified monomer；
By the assembly and the substrate monomer copolyreaction under the action of catalyst, photoresist is obtained.
4. the preparation method of photoresist according to claim 3, which is characterized in that in provider's molecular steps, packet
It includes:
Cyclodextrin is added to dissolution in the first solvent and obtains the first mixed solution；
The second solvent is added to first mixed solution and obtains the second mixed solution；
It quickly stirs second mixed solution and adds after third solvent obtains third mixed solution and stop reaction；
Third mixed solution described in rotary evaporation obtains the 4th mixed solution after removing acetone；
4th mixed solution is dissolved in the water of no ion and obtains the 5th mixed solution；
4th solvent is added in the 5th mixed solution and obtains the 6th mixed solution；
6th mixed solution is dialysed, and by the way that isolated host molecule material is lyophilized.
5. the preparation method of photoresist according to claim 4, which is characterized in that in modified monomer step is provided, packet
It includes:
Adamantanecarboxylic acid is added to the 5th solvent and obtains the 7th mixed solution；
It stirs the 7th mixed solution and rotates and obtain the 8th mixed solution；
It is added in the 8th mixed solution in the 6th solvent with hydroxyethyl methacrylate, the 8th mixed solution
In adamantane group and the hydroxyethyl methacrylate obtain the first monomer-polymer, the knot of first monomer-polymer
Structure formula is
Second comonomer polymer is added in first monomer-polymer and forms the 9th mixed solution；Described second is single
The structural formula of body compound are as follows:
Stir it is described 9th mixing after solution left standstill, filter obtain modified monomer solution.
6. the preparation method of photoresist according to claim 5, which is characterized in that in obtaining assembly step, comprising:
The host molecule ultrasonic disperse is obtained into the tenth mixed solution into distilled water；
The modified monomer solution is added in the tenth mixed solution；
Powdered assembly is obtained after being stirred at room temperature 24 hours, after freeze-drying.
7. the preparation method of photoresist according to claim 6, which is characterized in that by the assembly and the substrate
Monomer is under the action of catalyst in copolyreaction step, comprising:
The assembly is dissolved in the 7th solvent and obtains the 11st mixed solution；
It is chemically reacted hydroxyethyl methacrylate and butyl acrylate to obtain substrate monomer；
The substrate monomer and catalyst are added in the 11st mixed solution and chemically reacted, the light can be obtained
Photoresist.
8. the preparation method of photoresist according to claim 4, which is characterized in that
First solvent is sodium hydroxide；Second solvent is epoxychloropropane；The third solvent is acetone；Described
Four solvents are hydrochloric acid.
9. the preparation method of photoresist according to claim 5, which is characterized in that
5th solvent is thionyl chloride；
The molar ratio of the hydroxyethyl methacrylate and the diazido naphthoquinone derivative is 15:45~15:23.
10. the preparation method of photoresist according to claim 7, which is characterized in that
7th solvent includes polyethylene glycol methacrylate-styrene polymer, propylene glycol monomethyl ether, ethylene glycol ether acetate and lactic acid
Ethyl ester, the polyethylene glycol methacrylate-styrene polymer, the propylene glycol monomethyl ether, the ethylene glycol ether acetate and the lactic acid
Ethyl ester volume ratio is 1:1:1:1~3:6:9:8；
It is added in the 11st mixed solution in the step of being chemically reacted by the substrate monomer and catalyst,
The catalyst is azodiisobutyronitrile；
The reaction temperature of the chemical reaction is 40~60 DEG C, when reaction a length of 12h.
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