CN105199018A - Novel oxime ester photoinitiator as well as preparation and application thereof - Google Patents
Novel oxime ester photoinitiator as well as preparation and application thereof Download PDFInfo
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- CN105199018A CN105199018A CN201510745356.2A CN201510745356A CN105199018A CN 105199018 A CN105199018 A CN 105199018A CN 201510745356 A CN201510745356 A CN 201510745356A CN 105199018 A CN105199018 A CN 105199018A
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- 0 C=*C(C1C=CC(PC(C=C2)=CCC2C([Rn])=[U])=CC1)=* Chemical compound C=*C(C1C=CC(PC(C=C2)=CCC2C([Rn])=[U])=CC1)=* 0.000 description 2
Abstract
The invention discloses a novel oxime ester photoinitiator shown as general formulae I and II as well as preparation and an application thereof. The photoinitiator has excellent storage stability, photographic sensitivity, developing performance, pattern integrity and the like.
Description
Technical field
The present invention relates to a kind of new oxime ester lightlike initiating agent, their preparation method, and this compounds is as the photopolymerization initiator of alefinically unsaturated compounds system.
Background technology
Awernerl reported first in 1904 photochemical properties of oxime ester compound; within 1970, oxime ester class chemical combination starts to be used as light trigger; wherein O-acyl-oxime ester lightlike initiating agent QuantacurePDO(formula I) once applied by widespread commercial; but due to its poor heat stability, and be eliminated gradually.Oxime ester compound Recent study enliven, prior art such as: Macromol.Symp.2004,217,77; Patent CN101014569A, CN101321727A, CN101679394A, CN101687794A, CN99108598, CN02811675, CN1800885A, CN1928716A, CN101158812A, CN101525393A, CN101634807A, and WO2008138733A1, WO0052530A1, WO2007071497A1, WO2009019173A1, WO2009147031A2, WO2009147033A1 etc. describe the oxime ester of some carbazole structures and the oxime ester side chain dimer type compound of dependency structure.There is business-like oxime ester compound photoinitiator OXE01 and OXE02 on this basis, the photosensitivity system of these compounds composition particularly has sensitive response to 405 or 365 nanometer light, make field at BM and RGB of giant-screen LCD display and have important application, the product of similar nature also has oxime ester 305 and 304 disclosed in CN101565472B and CN101508744B.Light trigger disclosed in these can meet the general application requiring of the curing field such as present display panel and colored filter in varying degrees.
But the development of electronics technology is maked rapid progress, and existing procucts start to manifest deficiency in some Application Areass, and the update of product also proposes requirements at the higher level to light trigger.Such as, the many thermotolerances of photic erosion agent being applied to gap control material are at present not good, easily subsiding when baking or encapsulation procedure makes clearance material shrink, and in the processing procedures such as coating, exposure imaging deliberately extra clearance control the height of material and can increase its cost, heat when subsiding of being heated is melted the small molecules and will be polluted liquid crystal.And for example, in the making of high-end colored filter, light trigger need meet the basic demand of high resolution, good thermal stability on the one hand, on the other hand, the qualitative performance requirements of its high color need through highly colored resist, and along with the increase of pigment content, the solidification of color resist becomes more difficult, sharpness, the integrity degree of the rear image of its solidification also have higher requirement, and this solves the problems referred to above with regard to needing the initiator of more ISO.
In curing field, there is the development that the high and light trigger that is that be easy to prepare of high photosensitivity, stability is still this field first-selected, and research and development to have more high performance light trigger will be a core work in this field always.
Summary of the invention
The object of this invention is to provide a kind of new oxime ester lightlike initiating agent and Synthesis and applications thereof of excellent performance.This light trigger is excellent performance in stability in storage, light sensitivity, aobvious recessiveness and pattern integrity etc. not only, and compared with same photoinitiator, shows the light sensitivity and thermostability that significantly improve.
The technical scheme that the present invention realizes object is as follows:
New oxime ester lightlike initiating agent, it has as formula I, II:
Wherein,
N=1 or 2;
R
1, R
2, R
3can be the same or different, be independently selected from the straight or branched alkyl of C1-C20, C3-C8 cycloalkyl, C7-C10 phenyl substituted alkyl;
R
4, R
5, R
6can be the same or different, be independently selected from the straight or branched alkyl of C1-C20, C3-C8 cycloalkyl, C6-C20 aryl, wherein the alkyl of C1-C20 is unsubstituted or is replaced by one or more halogen, phenyl, alkoxyl group.
As preferred version of the present invention, above-mentioned formula I, II new oxime ester lightlike initiating agent:
R
1, R
2, R
3independently be selected from the straight or branched alkyl being expressed as C1-C5 independently, C5-C6 cycloalkyl, C7-C10 phenyl substituted alkyl;
R
4, R
5, R
6independently be selected from the straight or branched alkyl of C1-C5, C3-C8 cycloalkyl, C6-C10 aryl, wherein the alkyl of C1-C20 is unsubstituted or is replaced by one or more halogen, phenyl, alkoxyl group.
The invention still further relates to above-mentioned formula I, II the preparation method of new oxime ester lightlike initiating agent, comprise the following steps:
1) take triphenylphosphine as raw material, under the catalysis of aluminum chloride, iron trichloride or zinc chloride on phenyl acylations;
2) acylated product obtained obtains phosphine oxide intermediate through peroxidation;
3) phosphine oxide intermediate carries out oximation reaction with nitrous acid ester (as: ethyl nitrite, Isopentyl nitrite, the different monooctyl ester of nitrous acid etc.) or nitrite (as Sodium Nitrite, potassium nitrite etc.) under the effect of hydrogenchloride, sodium alkoxide or potassium alcoholate;
4) the product oxime that oximation reaction obtains becomes oxime ester with acyl chloride reaction;
。
N and R
1, R
2, R
3, R
4, R
5, R
6definition described above.
In above-mentioned preparation method, the raw material of use is all known compounds of the prior art, business can buy or be prepared from by known synthetic method.This preparation method is simple, and do not produce contaminative waste in preparation process, and product purity is high, yield is good, is applicable to industrialized mass production.
The invention still further relates to the new oxime ester lightlike initiating agent shown in above-mentioned formula I, II to comprise at Photocurable composition:
A) the unsaturated photopolymerizable compound of at least one olefinic and
B) as at least one formula I of light trigger, the compound of II.
One or more double bond can be contained containing ethylenical unsaturated double bonds compound.They can be low-molecular-weight (monomer) or relative high molecular (oligopolymer).Wrapping double bond containing Exemplary monomers is alkyl or hydroxy alkyl acrylate or methacrylic ester, such as, and methyl, ethyl, butyl, 2-ethylhexyl-or 2-hydroxyethylmethacry,ate, iso-bornyl acrylate, or methacrylic acid methyl or ethyl ester; Silicone acrylate; Acrylamide, Methacrylamide, (methyl) acrylamide that N-replaces; Vinyl ester as vinyl-acetic ester, vinyl ether as isobutyl vinyl ether, vinylbenzene, alkyl-and halogenated styrenes, NVP, vinyl chloride or vinylidene chloride.
Containing the monomer of two or more double bond as ethylene glycol, propylene glycol, neo-pentyl ethylene glycol, 1, the diacrylate of 6-hexylene glycol and dihydroxyphenyl propane, 4,4 '-bis-(2-acryloyloxyethoxy) diphenyl propane, Viscoat 295, pentaerythritol triacrylate or tetraacrylate, ethylene propylene acid esters, Vinylstyrene, divinyl succinate, diallyl phthalate, tricresyl phosphate allyl ester, tricarbimide triallyl ester and tricarbimide three (2-acryloyl ethyl) ester.
The example with relative high molecular (oligopolymer) polyunsaturated compounds is epoxy resin and polyethers, the polyurethane(s) of acrylated; Acrylated or the polyester containing vinyl ether group or epoxy group(ing).Unsaturated oligomer can also be unsaturated polyester resin, and they are have toxilic acid mostly, prepared by phthalic acid and one or more glycol and have the molecular weight of about 500-3000.In addition, also can use vinyl ether monomers and vinyl ether oligomers, and take maleic acid ester as terminal, there is the oligopolymer of polyester, polyurethane(s), polyethers, polyvinyl ether and epoxy main chains.
Alefinically unsaturated compounds can also be the ester of ethylenically unsaturated carboxylic acids and polyvalent alcohol epoxy compounds, with the polymkeric substance containing ethylenically unsaturated group on main chain or side chain radical, such as unsaturated polyester, polymeric amide or polyurethane(s) and multipolymer thereof, polyhutadiene or butadienecopolymer, polyisoprene and isoprene copolymer, containing the polymkeric substance of (methyl) acrylic and multipolymer on side chain, containing the polymkeric substance of (methyl) acrylic and multipolymer on side chain, and the mixture of one or more these polymkeric substance.
The example of unsaturated carboxylic acid is that vinylformic acid, methacrylic acid, butenoic acid, methylene-succinic acid, styracin and unsaturated fatty acids are as linolenic acid and oleic acid.Preferred vinylformic acid and methacrylic acid.
Suitable polyvalent alcohol is aromatic polyol and is especially aliphatic series and Cycloaliphatic polyols.Aromatic polyol as quinhydrones, 4,4 '-dihydroxydiphenyl, 2,2-bis-(4-hydroxy phenyl) propane, and (line style) phenolic varnish and phenol-formaldehyde A.Aliphatic series and Cycloaliphatic polyols are as aklylene glycol, and preferred C2-12, as ethylene glycol, 1,2-or 1, ammediol, 1,2-, 1,3-or 1,4-butyleneglycol, pentanediol, hexylene glycol, ethohexadiol, 12 carbon alkane glycol, glycol ether, triglycol, molecular weight are preferably the polyoxyethylene glycol, 1 of 200-1500,3-ring pentanediol, 1,2-, 1,3-or 1,4-cyclohexanediol, Isosorbide-5-Nitrae-hydroxymethyl-cyclohexane, glycerine, tetramethylolmethane, TriMethylolPropane(TMP), Dipentaerythritol or Sorbitol Powder etc.
The invention still further relates to the application of the new oxime ester lightlike initiating agent shown in above-mentioned formula I, II in Photocurable composition (i.e. photosensitive composite).Without limitation, this light trigger can be applicable to the aspects such as chromatic photoresist (RGB), black photoresistance (BM), spatial obstacle thing (Photo-spacer), dry film, semiconductor lithography glue and ink.
Embodiment
Below further describe concrete technical scheme of the present invention, so that those skilled in the art understand the present invention further, and do not form the restriction to its right.
Embodiment 1: compound 1
preparation
1) 4, 4 ', the preparation of 4 ' '-triacetyl triphenylphosphine: by triphenylphosphine (52.5g, 0.2mol) be dissolved in 300ml methylene dichloride, control temperature of reaction at 20-30 DEG C, add aluminum chloride (82.7g, 0.62mol) drip Acetyl Chloride 98Min. (48.7, 0.62mol), drip to finish and stir 2h, stopped reaction, reaction solution is poured in the dilute hydrochloric acid that 800g and 130ml concentrated hydrochloric acid is made into, stir 0.5h, leave standstill and separate organic phase, use dichloromethane extraction aqueous phase, merge organic phase, and wash with 200ml saturated sodium bicarbonate solution, become neutral to organic phase pH value, dry, precipitation recycling design, obtain pale yellow oil, purity 97%, also directly next step oxidizing reaction can not be carried out by recycling design.
2) in the organic phase of step 1) neutrality, 22.7g30% hydrogen peroxide is added, at 60 DEG C, react 3h, after reaction terminates, add sodium sulfite solution respectively and saturated sodium bicarbonate solution is washed, organic phase finally uses anhydrous magnesium sulfate drying, and recycling design obtains yellow oil.
3) hydrogenchloride is dissolved in organic solvent the solution obtaining hydrogenchloride THF; get the THF solution of 200g hydrogenchloride, wherein the content of hydrogenchloride is selected from 30g, adds step 2) obtain 4; 4 '; 4 ' '-triacetyl triphenylphosphine oxide, stirring and dissolving, drips 15.5g nitrite tert-butyl; insulation reaction; complete to raw material reaction, recycling design, obtains orange oily liquids 72.0g.
4) oily matter in step 3) is dissolved in ethylene dichloride, is cooled to 0 DEG C, add 47.0g triethylamine, drip 35.3g Acetyl Chloride 98Min., after raw material reaction is complete, add 3% dilute hydrochloric acid condition pH=2 ~ 3, stir 30min, stratification, organic phase is washed, dry, recycling design, cools to obtain yellow oil, obtains colorless oil through chromatography over CC (EtOAc/hexane=40/1), final product structure is confirmed by proton nmr spectra, and embodiments result is as follows:
1h-NMR(CDCl3,400MHz): δ 7.98 (d, 6H), 7.67 (dd,
3j (H, H)=8.3Hz,
3j (P, H)=11.1Hz, 6H), 2.48 (s, 9H), 1.90 (s, 9H);
31p-NMR (CDCl3,400MHz): δ 27.7 (s).
Embodiment 2: compound 2
preparation
1) 4, 4 ', 4 ' ' preparation of-three isobutyryl triphenylphosphines: by triphenylphosphine (52.5g, 0.2mol) be dissolved in 300ml methylene dichloride, control temperature of reaction at 20-30 DEG C, add aluminum chloride (82.7g, 0.62mol) drip isobutyryl chloride (42.6g respectively, 0.40mol) with butyryl chloride (16.5g, 0.21mol), drip to finish and stir 2h, stopped reaction, reaction solution is poured in the dilute hydrochloric acid that 800g and 130ml concentrated hydrochloric acid is made into, stir 0.5h, leave standstill and separate organic phase, use dichloromethane extraction aqueous phase, merge organic phase, and wash with 200ml saturated sodium bicarbonate solution, become neutral to organic phase pH value, dry, precipitation recycling design, obtain pale yellow oil, purity 96.7%.
2) in the organic phase of step 1) neutrality, 22.7g30% hydrogen peroxide is added, at 60 DEG C, react 3h, after reaction terminates, add sodium sulfite solution respectively and saturated sodium bicarbonate solution is washed, organic phase finally uses anhydrous magnesium sulfate drying, and recycling design obtains yellow oil.
3) hydrogenchloride is dissolved in organic solvent the solution obtaining hydrogenchloride THF; get the THF solution of 200g hydrogenchloride; wherein the content of hydrogenchloride is selected from 30g, adds step 2) the 4-ethanoyl-4 that obtains ', 4 ' '-two isobutyryl triphenylphosphine oxide; stirring and dissolving; drip 15.5g nitrite tert-butyl, insulation reaction, complete to raw material reaction; recycling design, obtains orange oily liquids 80.9g.
4) oily matter in step 3) is dissolved in ethylene dichloride, is cooled to 0 DEG C, add 47.0g triethylamine, drip 35.3g Acetyl Chloride 98Min., after raw material reaction is complete, add 3% dilute hydrochloric acid condition pH=2 ~ 3, stir 30min, stratification, organic phase is washed, dry, recycling design, obtain colorless oil through chromatography over CC (EtOAc/hexane=40/1), final product structure is confirmed by proton nmr spectra, and embodiments result is as follows:
1H-NMR（CDCl3，400MHz）：δ7.96(d，6H),7.68(dd，
3J(H,H)=8.3Hz,
3J(P,H)=11.1Hz，6H),2.08(s，9H),1.90(s，3H),1.79~1.82(m，2H),1.09(d，12H)；
31P-NMR(CDCl3，400MHz)：δ27.8(s)。
Embodiment 3: compound 3
preparation
1) 4, 4 ', the preparation of 4 ' '-triacetyl triphenylphosphine: by triphenylphosphine (52.5g, 0.2mol) be dissolved in 300ml methylene dichloride, control temperature of reaction at 20-30 DEG C, add aluminum chloride (82.7g, 0.62mol) drip Acetyl Chloride 98Min. (48.7, 0.62mol), drip to finish and stir 2h, stopped reaction, reaction solution is poured in the dilute hydrochloric acid that 800g and 130ml concentrated hydrochloric acid is made into, stir 0.5h, leave standstill and separate organic phase, use dichloromethane extraction aqueous phase, merge organic phase, and wash with 200ml saturated sodium bicarbonate solution, become neutral to organic phase pH value, dry, precipitation recycling design, obtain pale yellow oil, purity 97%.
2) in the organic phase of step 1) neutrality, 22.7g30% hydrogen peroxide is added, at 60 DEG C, react 3h, after reaction terminates, add sodium sulfite solution respectively and saturated sodium bicarbonate solution is washed, organic phase finally uses anhydrous magnesium sulfate drying, and recycling design obtains yellow oil.
3) hydrogenchloride is dissolved in organic solvent the solution obtaining hydrogenchloride THF; get the THF solution of 200g hydrogenchloride, wherein the content of hydrogenchloride is selected from 30g, adds step 2) obtain 4; 4 '; 4 ' '-triacetyl triphenylphosphine oxide, stirring and dissolving, drips 15.5g nitrite tert-butyl; insulation reaction; complete to raw material reaction, recycling design, obtains orange oily liquids 72.5g.
4) oily matter in step 3) is dissolved in ethylene dichloride, is cooled to 0 DEG C, add 47.0g triethylamine, drip 87.0g Benzoyl chloride, after raw material reaction is complete, add 3% dilute hydrochloric acid condition pH=2 ~ 3, stir 30min, stratification, organic phase is washed, dry, recycling design, obtain colorless oil through chromatography over CC (EtOAc/hexane=40/1), final product structure is confirmed by proton nmr spectra, and embodiments result is as follows:
1H-NMR（CDCl3，400MHz）：δ8.25(d，6H),7.33~7.89(m，21H),1.87(s，3H)；
31P-NMR(CDCl3，400MHz)：δ27.8(s)。
The structure of target product and
1h-NMR data list in table 1:
Table 1
Embodiment 18: performance evaluation
By preparation exemplary optical curing composition, every application performance of light trigger shown in formula I of the present invention, II is evaluated, comprises the aspects such as stability in storage, light sensitivity, developability, pattern integrity.
1. the preparation of Photocurable composition
Acrylate copolymer 100
(methacrylic acid Bian ester/methacrylic acid/hydroxyethyl methylacrylate (mol ratio is 70/10/20) multipolymer
（Mw：10,000））
Viscoat 295 (TMPTA) 100
Light trigger 2 ~ 3 to be measured
PMA solvent 25
In above-mentioned composition, light trigger is the oxime ester class chemical combination shown in formula I disclosed by the invention, II
Thing or light trigger well known in the prior art as a comparison, each component is mass parts.
2. exposure imaging
Above-mentioned Photocurable composition lucifuge stirred, feeding utilizes line rod film in PET template, and at 165 DEG C, dry 150min is except desolventizing, forms the film of film thickness about 2 μm.The substrate being formed with film is cooled to room temperature, enclose mask plate, with high voltage mercury lamp or LED light source, at the ultraviolet of 365 ~ 420nm wavelength, film is exposed, at 25 DEG C, in the sodium carbonate solution of 2.5%, flood 20s development subsequently, then use ultrapure washing, air-dry, at 220 DEG C, hard baking 30min makes figure fixing, evaluates the figure obtained.
3. the performance evaluation of Photocurable composition
(1) stability in storage
After the Photocurable composition of liquid state is at room temperature stored 3 months naturally, visually evaluate the precipitation degree of material according to following standard:
A: do not observe precipitation;
B: slightly observe precipitation;
C: observe obvious sediment.
(2) light sensitivity
During exposure, by residual film ratio after photoirradiation area development in step of exposure 90% or more minimum exposure amount be evaluated as exposure demand, exposure demand less expression sensitivity is higher.
(3) developability and pattern integrity
Substrate pattern is observed, to evaluate developability and pattern integrity by scanning electronic microscope (SEM).
Developability is according to following standard evaluation:
Zero: do not observe residue at unexposed portion;
◎: observe a small amount of residue at unexposed portion, but residue can accept;
●: observe obvious residue at unexposed portion.
Pattern integrity is according to following standard evaluation:
◇: do not observe pattern defect;
: observing small portion pattern has fewer defects;
◆: obviously observe many pattern defects.
Evaluation result is as shown in table 2:
Table 2
| Light trigger | Stability in storage | Mass color energy mJ/cm 2 | Developability | Image integrity |
| Embodiment 1 | A | 40 | ○ | ◇ |
| Embodiment 2 | A | 38 | ○ | ◇ |
| Embodiment 3 | A | 42 | ○ | ◇ |
| Embodiment 4 | A | 43 | ○ | ◇ |
| Embodiment 5 | A | 37 | ○ | ◇ |
| Embodiment 6 | A | 71 | ◎ | □ |
| Embodiment 12 | A | 50 | ○ | ◇ |
| Embodiment 13 | A | 75 | ◎ | □ |
| Embodiment 14 | A | 52 | ◎ | □ |
| Embodiment 16 | A | 55 | ○ | ◇ |
| Embodiment 17 | A | 39 | ○ | ◇ |
| OXE-01 | B | 205 | ◎ | ◆ |
| OXE-02 | B | 185 | ◎ | □ |
As can be seen from the result of table 2 content, the Photocurable composition comprising the new oxime ester lightlike initiating agent shown in formula I of the present invention, II has good stability in storage, all shows splendid light sensitivity, developability and pattern integrity.
In sum, the application performance of the new oxime ester lightlike initiating agent shown in formula I disclosed by the invention, II is excellent, is applied to the performance that Photocurable composition can greatly improve photocuring product.
Claims (5)
1. new oxime ester lightlike initiating agent, it has as formula I, II:
Wherein,
N=1 or 2;
R
1, R
2, R
3can be the same or different, be independently selected from the straight or branched alkyl of C1-C20, C3-C8 cycloalkyl, C7-C10 phenyl substituted alkyl;
R
4, R
5, R
6can be the same or different, be independently selected from the straight or branched alkyl of C1-C20, C3-C8 cycloalkyl, C6-C20 aryl, wherein the alkyl of C1-C20 is unsubstituted or is replaced by one or more halogen, phenyl, alkoxyl group.
2. oxime ester lightlike initiating agent new according to claim 1, is characterized in that:
R
1, R
2, R
3independently be selected from the straight or branched alkyl being expressed as C1-C5 independently, C5-C6 cycloalkyl, C7-C10 phenyl substituted alkyl;
R
4, R
5, R
6independently be selected from the straight or branched alkyl of C1-C5, C3-C8 cycloalkyl, C6-C10 aryl, wherein the alkyl of C1-C20 is unsubstituted or is replaced by one or more halogen, phenyl, alkoxyl group.
3. oxime ester lightlike initiating agent new according to claim 1, is characterized in that preparation method comprises the following steps:
1) take triphenylphosphine as raw material, under the catalysis of aluminum chloride, iron trichloride or zinc chloride on phenyl acylations;
2) phosphine oxide intermediate under the effect of hydrogenchloride, sodium alkoxide or potassium alcoholate with nitrous acid ester or nitrite
Carry out oximation reaction;
3) the product oxime that oximation reaction obtains becomes oxime ester with acyl chloride reaction;
4) acylated product obtained obtains phosphine oxide intermediate through peroxidation;
Wherein:
N=1 or 2;
R
1, R
2, R
3can be the same or different, be independently selected from the straight or branched alkyl of C1-C20, C3-C8 cycloalkyl, C7-C10 phenyl substituted alkyl;
R
4, R
5, R
6can be the same or different, be independently selected from the straight or branched alkyl of C1-C20, C3-C8 cycloalkyl, C6-C20 aryl, wherein the alkyl of C1-C20 is unsubstituted or is replaced by one or more halogen, phenyl, alkoxyl group.
4. preparation method according to claim 3, is characterized in that step 2) described nitrous acid ester is selected from ethyl nitrite, Isopentyl nitrite, the different monooctyl ester of nitrous acid; Nitrite is selected from Sodium Nitrite, potassium nitrite etc.
5. a Photocurable composition comprises:
A) the unsaturated photopolymerizable compound of at least one olefinic and
B) as at least one compound according to claim 1 of light trigger.
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Cited By (2)
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| CN107936145A (en) * | 2016-10-12 | 2018-04-20 | 常州强力电子新材料股份有限公司 | A kind of oxime ester lightlike initiating agent containing fluorenes |
| CN108727517A (en) * | 2017-04-25 | 2018-11-02 | 常州强力先端电子材料有限公司 | Fluorenes oxime ester lightlike initiating agent, preparation method and application containing polymerizable groups |
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| US6313344B1 (en) * | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
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| US6313344B1 (en) * | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
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| CN107936145A (en) * | 2016-10-12 | 2018-04-20 | 常州强力电子新材料股份有限公司 | A kind of oxime ester lightlike initiating agent containing fluorenes |
| CN108727517A (en) * | 2017-04-25 | 2018-11-02 | 常州强力先端电子材料有限公司 | Fluorenes oxime ester lightlike initiating agent, preparation method and application containing polymerizable groups |
| CN108727517B (en) * | 2017-04-25 | 2021-05-07 | 常州强力先端电子材料有限公司 | Fluorenoxime ester photoinitiator containing polymerizable group, and preparation method and application thereof |
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|---|---|
| CN105199018B (en) | 2017-03-22 |
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Effective date of registration: 20230927 Address after: 300382 Floor 1, Building D2, East Zone, No. 1, Xuefu West Road, Xuefu Industrial Zone, Jingwu Town, Xiqing District, Tianjin Patentee after: Tianjin Jiuri Semiconductor Materials Co.,Ltd. Address before: No.99 Dongkang Road, Jintan Economic Development Zone, Changzhou City, Jiangsu Province 213200 Patentee before: CHANGZHOU JIURI CHEMICAL Co.,Ltd. |