WO2014121701A1 - 一种咔唑酮肟酯类高感光度光引发剂 - Google Patents
一种咔唑酮肟酯类高感光度光引发剂 Download PDFInfo
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- WO2014121701A1 WO2014121701A1 PCT/CN2014/071445 CN2014071445W WO2014121701A1 WO 2014121701 A1 WO2014121701 A1 WO 2014121701A1 CN 2014071445 W CN2014071445 W CN 2014071445W WO 2014121701 A1 WO2014121701 A1 WO 2014121701A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- photoinitiator
- carbazolone
- oxime ester
- reaction
- Prior art date
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 206010034972 Photosensitivity reaction Diseases 0.000 title abstract description 6
- 150000002148 esters Chemical class 0.000 title abstract description 3
- -1 carbazolone oxime ester Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- HRGZAWUQJJICCK-UHFFFAOYSA-N C1=CC=C2C3=CC=CC(=NO)C3=NC2=C1 Chemical class C1=CC=C2C3=CC=CC(=NO)C3=NC2=C1 HRGZAWUQJJICCK-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 230000036211 photosensitivity Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 8
- 238000001698 laser desorption ionisation Methods 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- YIDIIHXWTKOCRD-UHFFFAOYSA-N n-(1,3-oxazol-2-yl)hydroxylamine Chemical compound ONC1=NC=CO1 YIDIIHXWTKOCRD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 0 *CC(c(cc1)cc(c2c3)c1[n](*)c2ccc3C([Al])=O)=O Chemical compound *CC(c(cc1)cc(c2c3)c1[n](*)c2ccc3C([Al])=O)=O 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
- SZQVEGOXJYTLLB-UHFFFAOYSA-N 3-cyclopentylpropanoyl chloride Chemical compound ClC(=O)CCC1CCCC1 SZQVEGOXJYTLLB-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- MAOLGBSDPAGEBK-UHFFFAOYSA-N CC(N1CCN(Cc2ccc(C)cc2)CC1)=O Chemical compound CC(N1CCN(Cc2ccc(C)cc2)CC1)=O MAOLGBSDPAGEBK-UHFFFAOYSA-N 0.000 description 1
- ALTFLAPROMVXNX-UHFFFAOYSA-N CC1OC(C)(C)OC1 Chemical compound CC1OC(C)(C)OC1 ALTFLAPROMVXNX-UHFFFAOYSA-N 0.000 description 1
- KBPZFCMPFYLUPD-UHFFFAOYSA-N Cc(ccc1c2)cc1ccc2[O](C)C Chemical compound Cc(ccc1c2)cc1ccc2[O](C)C KBPZFCMPFYLUPD-UHFFFAOYSA-N 0.000 description 1
- KKPCPGWGLHHNSW-UHFFFAOYSA-N Cc1cc(CN2CCOCC2)ccc1 Chemical compound Cc1cc(CN2CCOCC2)ccc1 KKPCPGWGLHHNSW-UHFFFAOYSA-N 0.000 description 1
- GSDPDUAEOGGTQE-UHFFFAOYSA-N Cc1ccc(CN2CCN(C)CC2)cc1 Chemical compound Cc1ccc(CN2CCN(C)CC2)cc1 GSDPDUAEOGGTQE-UHFFFAOYSA-N 0.000 description 1
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003617 indole-3-acetic acid Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
Definitions
- the present invention relates to the field of photoinitiators, and in particular to an oxazolone oxime-based photoinitiator. Background technique
- Photocuring refers to the curing process of monomers, oligomers or polymer matrices under light induction. This technology has a wide range of applications in modern microelectronics, such as photocurable inks, liquid crystal panel packaging, photosensitive printing plates, Filters, photoresists, etc.
- the core of photocuring technology is the photocurable polymerizable monomer and a suitable photoinitiator. Upon irradiation with a light source of a certain wavelength, the photoinitiator generates a reactive group that excites an unsaturated group in the polymerizable monomer to cause a polymerization reaction, thereby causing curing of the material.
- the photoinitiator is the most important factor affecting the photographic properties of the photocurable composition (i.e., the photosensitive composition).
- the photoinitiators have generally low photosensitivity and are limited in the range of applicable light sources, most of which are only suitable for UV excitation.
- existing rouge photoinitiators such as
- CN101508744A discloses an oxazolidinyl ester photoinitiator, a commercially available sulfonic acid photoinitiator OXE-02, a ketone oxime photoinitiator disclosed in CN101565472A, and a commercially available ketone blush light.
- the initiator OXE-01, etc. can only meet the application requirements of mercury lamps (including high pressure, medium pressure, low pressure mercury lamps) as exposure sources.
- the present invention discloses an oxazolone oxime-based photoinitiator, which can not only be matched with a mercury lamp source, but also can be well exposed with low-energy, long-wavelength output such as LED and LDI. Source matching, with high sensitivity.
- the object of the present invention is to provide a novel oxazolone oxime ester photoinitiator which has excellent sensitizing properties, especially in exposure light sources such as LED and LDI, in order to achieve the above technical effects,
- the invention uses the following technical solutions:
- R 2 is a linear or branched alkyl group of Cr ⁇ C ⁇
- R 3 is a Cr ⁇ do alkyl group, or a C 3 ⁇ C 8 cycloalkyl group, or a cycloalkylalkyl group consisting of a CH alkyl group and a C 3 ⁇ C 8 cycloalkyl group, or an optionally alkyl group (ie, a phenyl group which may or may not have a substituent;
- Ar is a substituted aryl group having an S or 0 heterocyclic group having an optional substituent (i.e., a substituent may or may not be contained), or a substituent having a 0, S, and N atom.
- the group is preferably a linear or branched alkyl group of CH ⁇ , more preferably a methyl group, an ethyl group, a n-propyl group or an n-butyl group, and particularly preferably an ethyl group.
- the group is preferably a linear or branched alkyl group of CH ⁇ , more preferably a methyl group.
- the S or O-containing heterocyclic group having an optional substituent preferably has 0 to 2 substituents, particularly 0 to 2 methyl or ethyl groups; and the S or 0 heterocyclic ring.
- the group is preferably a furyl group or a thienyl group; the substituent group having a 0, S, and N atom in the substituted aryl group is preferably an alkylthio group, an alkoxy group, an alkylamino group, a piperazinyl group, a morpholinyl group or the like.
- the Ar group is preferably selected from the following structures:
- Another object of the present invention is to provide a method for preparing an oxazolone oxime ester photoinitiator represented by the above formula (I), which comprises carbazole as a starting material, comprising the following steps:
- Substitution reaction The carbazole is dissolved in an organic solvent and subjected to a substitution reaction with a bromo alkane R 2 -Br to obtain an intermediate a, that is, a 9-R 2 -based carbazole.
- the reaction process is as follows:
- the starting materials used in the above preparation methods are all known compounds in the prior art, are commercially available or can be prepared by known synthetic methods, and the reaction principle of each step is also easily understood by those skilled in the art.
- an intermediate compound i.e., the above intermediate c
- the oxazolone oxime-based photoinitiator of the above formula (I) which has the following structure:
- R 2 and Ar are as defined above, and are the same as defined in the formula (I).
- the oxazolone oxime ester compound of the formula (I) of the present invention can be used as a photoinitiator in a photosensitive (photocurable) composition, and has very excellent photosensitivity.
- the other components in the photosensitive composition are not particularly limited herein, and may be components well known and commonly used in the art (for example, see the disclosure of CN101059655A, the entire disclosure of which is incorporated herein by reference.
- the oily viscous material was obtained by rotating the bottle, and the viscous material was poured into 150 ml of petroleum ether and stirred to precipitate. After suction filtration, a yellow powdery solid was obtained, which was dried at 70 ° C for 5 h to obtain a product of 14.8 g, yield 74%, and a relative purity of 95%.
- Example 2 The compounds of Examples 2 to 11 were prepared from the corresponding reagents by the method shown in Example 1.
- the target compound and its 3 ⁇ 4-NMR data are listed in Table 1.
- the performance of the photoinitiator of the present invention was tested and compared with the commercially available photoinitiator Irgacure 369 (2-phenyl-2-dimethylamino-1-(-4) -morpholine phenyl)-butanone-1), OXE-01 (1-(4-phenylthiophenyl)-octane-1,2-dione-2-benzoate oxime), and substance A (The ketone oxime photoinitiator disclosed in CN101565472A is 1-(4-phenylthiophenyl)-(3-cyclopentyl)-propane-1,2-dione-2-benzoic acid oxime ester). . 1, UV absorption wavelength test
- Test method Accurately weigh the photoinitiator product O.OOlg in a 100ml volumetric flask, then add acetonitrile to the volumetric flask to the 100ml mark, prepare a solution of 10_ 5 g/ml concentration, and use the spectrophotometer for UV absorption. Test, test results are shown in Table 2.
- the oxazolone oxime ester photoinitiator of the present invention has a longer wavelength ultraviolet absorption than the conventional photoinitiator and the existing ketone oxime photoinitiator, and is easier to A long wavelength source is matched.
- the photoinitiator of the formula (I) disclosed in the present invention exhibits higher than Irgacure 369, OXE-01, and substance A under irradiation of a long-wavelength output LED lamp. Sensitivity. Namely, the oxazolone oxime ester compound of the present invention is more excellent in photosensitive (photocuring) properties as a photoinitiator.
- the oxazolone oxime ester photoinitiator of the present invention has excellent application performance and has particularly high photographic performance, especially in low-energy, long-wavelength output LED, LDI and other exposure light sources.
- the high sensitivity is obviously superior to the commercially available photoinitiators such as Irgacure 369 and OXE-01, and is also superior to the oxazolone oxime ester photoinitiators disclosed in CN101565472A.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015553001A JP6082821B2 (ja) | 2013-02-08 | 2014-01-26 | カルバゾールケトオキシムエステル系高い感光度の光開始剤 |
US14/648,120 US9815823B2 (en) | 2013-02-08 | 2014-01-26 | Carbazole ketoxime ester high-photosensitivity photoinitiator |
KR1020157018755A KR101742473B1 (ko) | 2013-02-08 | 2014-01-26 | 카바졸 케톡심 에스테르 고-감광도 광개시제 |
Applications Claiming Priority (2)
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CN201310050577.9A CN103130919B (zh) | 2013-02-08 | 2013-02-08 | 一种咔唑酮肟酯类高感光度光引发剂 |
CN201310050577.9 | 2013-02-08 |
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WO2014121701A1 true WO2014121701A1 (zh) | 2014-08-14 |
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PCT/CN2014/071445 WO2014121701A1 (zh) | 2013-02-08 | 2014-01-26 | 一种咔唑酮肟酯类高感光度光引发剂 |
Country Status (5)
Country | Link |
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US (1) | US9815823B2 (zh) |
JP (1) | JP6082821B2 (zh) |
KR (1) | KR101742473B1 (zh) |
CN (1) | CN103130919B (zh) |
WO (1) | WO2014121701A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9637444B2 (en) | 2014-03-18 | 2017-05-02 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Bisoxime ester photoinitiator and preparation method and use thereof |
WO2021175855A1 (en) | 2020-03-04 | 2021-09-10 | Basf Se | Oxime ester photoinitiators |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103130919B (zh) * | 2013-02-08 | 2015-02-25 | 常州强力先端电子材料有限公司 | 一种咔唑酮肟酯类高感光度光引发剂 |
JP6365118B2 (ja) * | 2013-09-20 | 2018-08-01 | 三菱ケミカル株式会社 | 感光性樹脂組成物、それを硬化させてなる硬化物、ブラックマトリックス及び画像表示装置 |
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