CN104710615B - Photosensitive resin composition, photosensitive resin and organic light emitting diode display element - Google Patents
Photosensitive resin composition, photosensitive resin and organic light emitting diode display element Download PDFInfo
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- 229920005989 resin Polymers 0.000 title claims abstract description 92
- 239000011347 resin Substances 0.000 title claims abstract description 92
- 239000011342 resin composition Substances 0.000 title abstract description 4
- 239000000470 constituent Substances 0.000 claims description 43
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 29
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 29
- 239000010409 thin film Substances 0.000 claims description 21
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- 238000002834 transmittance Methods 0.000 claims description 14
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052733 gallium Inorganic materials 0.000 claims description 10
- 229910052738 indium Inorganic materials 0.000 claims description 10
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 10
- 239000011787 zinc oxide Substances 0.000 claims description 9
- 229910021420 polycrystalline silicon Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229910021417 amorphous silicon Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 238000003384 imaging method Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 13
- 239000011521 glass Substances 0.000 description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 239000011241 protective layer Substances 0.000 description 8
- -1 aromatic radical Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- GUGNSJAORJLKGP-UHFFFAOYSA-K sodium 8-methoxypyrene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].C1=C2C(OC)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 GUGNSJAORJLKGP-UHFFFAOYSA-K 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- NIOYEYDJTAEDFH-UHFFFAOYSA-N 1-(2-hydroxyethoxy)-2-methylpropan-2-ol Chemical compound CC(C)(O)COCCO NIOYEYDJTAEDFH-UHFFFAOYSA-N 0.000 description 1
- VIETUFSZPCIVQL-UHFFFAOYSA-N 1-methyl-3h-pyrrol-2-one Chemical class CN1C=CCC1=O VIETUFSZPCIVQL-UHFFFAOYSA-N 0.000 description 1
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 1
- OSUWBBMPVXVSOA-UHFFFAOYSA-N 4-(4-carbonochloridoylphenoxy)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=C(C(Cl)=O)C=C1 OSUWBBMPVXVSOA-UHFFFAOYSA-N 0.000 description 1
- 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- BRDOFYPYQFDHOQ-UHFFFAOYSA-N butyl acetate;hexanoic acid Chemical compound CCCCCC(O)=O.CCCCOC(C)=O BRDOFYPYQFDHOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- LNSXAHXVHYLJEG-UHFFFAOYSA-N ethyl 2-hydroxypropanoate;2-hydroxy-2-methylbutanoic acid Chemical compound CCOC(=O)C(C)O.CCC(C)(O)C(O)=O LNSXAHXVHYLJEG-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Abstract
The invention discloses a photosensitive resin composition, a photosensitive resin and an organic light-emitting diode display element. The photosensitive resin composition can be used for preparing photosensitive resin and can be applied to an organic light-emitting diode display element. Therefore, the phenomenon of light leakage among pixels can be reduced, the contrast of the organic light-emitting diode display element can be improved, and the imaging quality of the OLED display element can be improved.
Description
Technical field
The present invention relates to a kind of photosensitive resin constituent and its made photosensitive resins and organic light-emitting diode display
Element.
Background technique
Organic Light Emitting Diode (Organic Light Emitting Diode, OLED) display element, it is also known as organic
Electroluminescence (Organic Electroluminescence, OEL) display element, have self-luminous, wide viewing angle, high resolution,
The advantages that rapid reaction, low operating voltage, high brightness, deflection, askiatic ghost, in addition, because it is not required to backlight and liquid crystal folder
Layer separately has many advantages, such as frivolous, portable property, and becomes the new trend of flat-panel screens.
However, the spacing between different pixels is smaller and smaller as OLED display element pixels increasingly refine, picture is easily caused
Light leakage is generated between element, lowers the contrast of OLED display element, and then influence the image quality of OLED display element.
Summary of the invention
A purpose of the present invention is that a kind of photosensitive resin constituent is provided, by sense made by this photosensitive resin constituent
Photopolymer resin is applied to OLED display element, can avoid generating light leakage between pixel, therefore can promote the contrast of OLED display element,
And then promote the image quality of OLED display element.In addition, photosensitive resin made by photosensitive resin constituent of the invention can
High temperature resistant can bear up to 300 DEG C or more in OLED display element vapor deposition manufacture craft of high temperature.
One embodiment of an aspect according to the present invention is to provide a kind of photosensitive resin constituent, photosensitive resin composition
Object includes polyphenyl oxazole predecessor and an at least photosensitive compounds.
Polyphenyl oxazole predecessor has the structure as shown in formula (I):
In formula (I), X and E respectively stand alone as bivalent group, and the integer that n is 5 to 60.
Photosensitive compounds have to be tied as shown in formula (II), formula (III), formula (IV), formula (V), formula (VI) or formula (VII)
Structure:
In formula (II)~formula (VII), R1To R20Respectively stand alone as group shown in hydrogen, formula (i) or formula (ii), R1To R4In
At least one is group shown in formula (i) or formula (ii), R5To R7At least one of for group shown in formula (i) or formula (ii), R8
To R10At least one of for group shown in formula (i) or formula (ii), R11To R13At least one of for shown in formula (i) or formula (ii)
Group, R14To R16At least one of for group shown in formula (i) or formula (ii), R17To R20At least one of be formula (i) or formula
(ii) group shown in.
Formula (i) and formula (ii) are as follows:
According to photosensitive resin constituent above-mentioned, X can be-C (CF3)2-、-C(CH3)2,-O- or-S-.
According to photosensitive resin constituent above-mentioned, E can be-(CH2)m-、
, wherein R21To R24Respectively stand alone as the alkyl of carbon number 1 to 3, the aromatic radical of carbon number 3 to 7 or naphthenic base, m be 0 to
10 integer, r are integer of 1 to 10.
According to photosensitive resin constituent above-mentioned, the weight ratio of photosensitive compounds and polyphenyl oxazole predecessor is MR1,
It can meet following condition: 0.15≤MR1≤1.Preferably, following condition: 0.2≤MR1≤0.51 can be met.
It can also include development accelerant according to photosensitive resin constituent above-mentioned.Development accelerant and photosensitive compounds
Weight ratio be MR2, following condition: 0≤MR2≤0.9 can be met.Preferably, it can meet following condition: 0≤MR2≤
0.7.More preferably, following condition: 0≤MR2≤0.4 can be met.
Another embodiment of an aspect according to the present invention is to provide a kind of photosensitive resin, by photosensitive tree above-mentioned
The heated step of fat composition is formed, and makes the cyclisation of polyphenyl oxazole predecessor to form polyphenyl oxazole by heating stepses.
According to photosensitive resin above-mentioned, wherein heating stepses can carry out 1 hour to 5 hours in 150 DEG C to 350 DEG C.
According to photosensitive resin above-mentioned, wherein light transmittance of the photosensitive resin to wavelength less than or equal to 400nm is less than
11%.
The a further embodiment of an aspect according to the present invention is to provide a kind of OLED display element, OLED display element
Include substrate, thin film transistor (TFT) and photosensitive resin above-mentioned.Thin film transistor (TFT) is set to above substrate, and photosensitive resin is set to
Above thin film transistor (TFT).
According to OLED display element above-mentioned, wherein thin film transistor (TFT) can be amorphous silicon transistor (Amorphous Si
TFT), low-temperature polycrystalline silicon transistor (Low Temperature Poly-Si TFT) or indium gallium zinc oxide thin film transistor (TFT)
(Indium Gallium Zinc Oxide TFT)。
Detailed description of the invention
Fig. 1 is a kind of partial cutaway schematic of OLED display element of an embodiment of the present invention;
Fig. 2 is another partial cutaway schematic of the OLED display element of Fig. 1;
Fig. 3 is the light transmittance of the embodiment of the present invention 1 to 4 and reference examples 1 ' and 2 ' and the relational graph of wavelength.
Symbol description
100: substrate 300: protective layer
200: thin film transistor (TFT) 400: pixel defining layer
210: grid 500: anode
220: gate insulating layer 600: organic luminous layer
230: conversion zone 700: cathode
240: etch stop layer 800: arrow
250: drain electrode 900: arrow
260: source electrode M: pixel line of demarcation
Specific embodiment
Photosensitive resin constituent
Photosensitive resin constituent includes polyphenyl oxazole predecessor and an at least photosensitive compounds.In addition, photosensitive resin
Constituent can also include solvent, and selectively also include catalyst and/or additive.
Polyphenyl oxazole predecessor can have the structure as shown in formula (I):
In formula (I), X and E respectively stand alone as bivalent group, and the integer that n is 5 to 60.
When n is less than 5, when being formed by photosensitive resin as photoresist with photosensitive resin constituent, can not stop
Developer such as tetramethyl ammonium hydroxide (tetramethylammonium hydroxide, TMAH), occurs photosensitive when being easy to develop
Resin removes the phenomenon that (peeling).When n is greater than 60, photosensitive resin constituent not readily dissolves in solvent and is unfavorable for applying
Cloth, in addition, its exposure region is not easy in development when being formed by photosensitive resin as photoresist with photosensitive resin constituent
Removal.
According to photosensitive resin constituent above-mentioned, X can be-C (CF3)2-、-C(CH3)2,-O- or-S-.
According to photosensitive resin constituent above-mentioned, E can be
-(CH2)m-、
, wherein R21To R24Respectively stand alone as the alkyl of carbon number 1 to 3, the aromatic radical of carbon number 3 to 7 or naphthenic base, m be 0 to
10 integer, r are integer of 1 to 10.
For example, polyphenyl oxazole predecessor can be but be not limited to formula (I-1), formula (I-2) and structure shown in formula (I-3):
Photosensitive compounds have to be tied as shown in formula (II), formula (III), formula (IV), formula (V), formula (VI) or formula (VII)
Structure:
In formula (II)~formula (VII), R1To R20Respectively stand alone as group shown in hydrogen, formula (i) or formula (ii), R1To R4In
At least one is group shown in formula (i) or formula (ii), R5To R7At least one of for group shown in formula (i) or formula (ii), R8
To R10At least one of for group shown in formula (i) or formula (ii), R11To R13At least one of for shown in formula (i) or formula (ii)
Group, R14To R16At least one of for group shown in formula (i) or formula (ii), R17To R20At least one of be formula (i) or formula
(ii) group shown in.
Formula (i) and formula (ii) are as follows:
For example, photosensitive compound can be but be not limited to formula (II-1), formula (III-1), formula (III-2), formula (III-
3), structure shown in formula (IV-1), formula (V-1), formula (VI-1) or formula (VII-1), as shown in following table one:
According to photosensitive resin constituent above-mentioned, the weight ratio of photosensitive compounds and polyphenyl oxazole predecessor is MR1,
It can meet following condition: 0.15≤MR1≤1.Preferably, following condition: 0.2≤MR1≤0.51 can be met.When MR1 is small
In 0.15, then light of the wavelength less than or equal to 400nm can not be stopped effectively with photosensitive resin prepared by photosensitive resin constituent
It penetrates.
Photosensitive resin constituent can also include solvent, and workable solvent can be but be not limited to gamma-butyrolacton (gamma-
Butyl lactone, GBL), propylene glycol methyl ether acetate (propylene glycol monomethyl ether
Acetate, PGMEA), propylene glycol monomethyl ether (propylene glycol methyl ether, PGME), ethyl lactate (ethyl
Lactate), n-butyl acetate (n-butyl acetate), cyclohexanone (cyclohexanone), 3- ethoxyl ethyl propionate
(ethyl 3-ethoxypropionate), diethylene glycol dimethyl ether (dimethyl diethylene glycol), N- methyl
Pyrrolones (N-methyl pyrrolidinone, NMP), n,N-dimethylacetamide (N, N-Dimethyl Acetamide,
) or 2-HEPTANONE (2-heptanone, also known as Methyl Amyl Ketone, MAK) DMAc.
Photosensitive resin constituent selectively also includes catalyst and/or additive.Before catalyst facilitates polyphenyl oxazole
Object cyclisation is driven to form polyphenyl oxazole, workable catalyst can be but be not limited to methyl tosylate (mthyl p-
Toluenesulfonate, MPTS).Additive can be but be not limited to coating material (surface modifier) or development rush
Into agent (development promoter).Coating material helps to make that photosensitive resin constituent surface is flat and film thickness is equal
Even, workable coating material can be but be not limited to fluorinated acrylic resin (Fluorinated Acrylic Resin, quotient
The name of an article is known as F561, buys from DIC Co., Ltd).Development accelerant helps to reduce the manufacture craft time.Development accelerant with
The weight ratio of photosensitive compounds is MR2, can meet following condition: 0 < MR2≤0.9, can properly increase MR1's as a result,
Size, and lowest exposure amount (threshold exposure dose, Eth) can be reduced.Workable development accelerant can be but
It is not limited to Polyphenols (Multiphenol), workable Polyphenols is as shown in two Chinese style of table (VIII-1) to formula (VIII-7)
Structure:
Photosensitive resin
Photosensitive resin is formed by the heated step of photosensitive resin constituent above-mentioned, makes polyphenyl oxazole by heating stepses
Predecessor is cyclized to form polyphenyl oxazole, to obtain photosensitive resin.Aforementioned heating stepses can carry out 1 hour extremely in 150 DEG C to 350 DEG C
5 hours.
In specific words, it prepares photosensitive resin to comprise the steps of: firstly, carry out a whipping step, photosensitive resin is formed
Object (imply that polyphenyl oxazole predecessor, photosensitive compounds, solvent, catalyst (functionality) and additive (it is inessential at
Point)) be mixed at normal temperature, aforesaid ingredients are placed in container and using blender with 120rpm's in one embodiment
Revolving speed stir about 1 hour.
Later, a filtration step is carried out, aforementioned stirred photosensitive resin constituent is filtered and taken filtrate, is implemented one
Polytetrafluoroethylene (PTFE) (PTFE) filter membrane in example using 0.45 μm is with about 4kg/cm2Pressure carry out.
Then, an application step is carried out, aforementioned gained filtrate is coated on substrate to form a coat, the material of substrate
Matter can be glass, the method for coating including but not limited to idler wheel rubbing method, method of spin coating and print process, with formed with a thickness of
3.5 μm to 4.0 μm of coat.
Finally, carrying out heated baking to coat, make the cyclisation of polyphenyl oxazole predecessor to form polyphenyl oxazole, to be felt
Photopolymer resin.
OLED display element
Fig. 1 is please referred to, the part section signal according to a kind of OLED display element of an embodiment of the present invention is painted
Figure.OLED display element includes substrate 100, thin film transistor (TFT) 200, protective layer (passivation) 300, pixel defining layer
(pixel defined layer) 400, anode 500, organic luminous layer 600 and cathode 700.Thin film transistor (TFT) 200 is set to
200 top of thin film transistor (TFT) is arranged in 100 top of substrate, protective layer 300, and pixel defining layer 400 is set to 300 top of protective layer,
Wherein protective layer 300 and/or pixel defining layer 400 can be photosensitive resin of the invention.
Thin film transistor (TFT) 200 includes grid 210, gate insulating layer 220, conversion zone 230, etch stop layer 240, drain electrode
250, source electrode 260, wherein conversion zone 230 can be amorphous silicon (Amorphous), low temperature polycrystalline silicon (Low Temperature
Poly-Si) or indium gallium zinc oxide (Indium Gallium Zinc Oxide), in other words, thin film transistor (TFT) 200 can be non-
Crystal silicon transistor, low-temperature polycrystalline silicon transistor or indium gallium zinc oxide thin film transistor (TFT).
Referring to figure 2., it is painted another partial cutaway schematic of the OLED display element of Fig. 1.In Fig. 2, work as protective layer
300 when being photosensitive resin of the invention, helps to reduce the light that is issued of organic luminous layer 600 logical along the direction of arrow 800
Pixel line of demarcation M is crossed, implies that and generates light leakage between avoidable pixel.When pixel defining layer 400 is photosensitive resin of the invention,
Helping, which reduces the light that organic luminous layer 600 is issued, passes through pixel line of demarcation M along the direction of arrow 900, implies that avoidable
Light leakage is generated between pixel.Therefore, it when protective layer 300 and/or pixel defining layer 400 are photosensitive resin of the invention, can all keep away
Exempt to generate light leakage between pixel, and the contrast of OLED display element can be promoted, and then the imaging of OLED display element can be promoted
Quality.
The method for measurement of the property of photosensitive resin
(1) method for measurement of lowest exposure amount (Eth): after the agitated step of photosensitive resin constituent, filtration step,
It is coated on the coat that glass substrate forms 3.8 μm~4.0 μm, Corning Incorporated (Corning Inc.) institute can be selected in glass substrate
The EXG glass of the 0.63mm thickness of production or Japan Electric Glass company (Nippon Electric Glass Co, Ltd) give birth to
The OA-10 glass of the 0.63mm thickness of production carries out the exposure of different-energy after coat progress heated baking is obtained photosensitive resin
(G, H, L Line) and development carries out 60 seconds, later, observation nothing under which kind of energy using TMAH as developer wherein developing
Residual film, resulting energy are Eth.Eth is preferably less than, is equal to 175mJ/cm2, more preferably it is less than 130mJ/cm2If Eth is big
In 175mJ/cm2, will lead to the manufacture craft time for exposure too long.
(2) glass substrate (forming method and the Eth of photosensitive resin the measurement method (T%) of light transmittance: be will be covered with
Method for measurement in it is identical), with UV-visible spectroscopy (model are as follows: Perkin-Elmer Lamda 25) measurement penetrate
After spectrometer is calibrated, glass substrate is placed in spectrometer for rate, and scanning range measures this section by 800nm to 350nm
Penetrance.
(3) method for measurement of development loss (dark erosion): the glass substrate that will be covered with photosensitive resin (is formed
Method is identical with the method for measurement of Eth), thickness measuring is carried out, thickness t1 is obtained, later by this glass substrate not exposed
In the case where, directly with 2.38wt%TMAH development 60 seconds, then a thickness measuring is carried out, obtain thickness t2, development loss is
t1-t2.It is 0 μm~0.18 μm that preferred range is lost in development, and more preferably range is 0 μm~0.1 μm.
According to above embodiment, specific embodiment set forth below is described in detail.
The synthesis of polyphenyl oxazole predecessor (I-1)
Take bis- (3- amino-4-hydroxylphenyl) hexafluoropropane (2,2-Bis- (3amino-4-hydroxyphenyl) of 2,2-
Hexafluoropropane) 91.57 grams, volume is added is 1 public by 39.55 grams and 363 milliliters of pyridine (pyridine) of NMP
In the four-necked bottle risen, after bis- (3- amino-4-hydroxylphenyl) the hexafluoropropane dissolutions of 2,2-, it is cooled to 0 DEG C with ice bath, then to add
Funnel is added dropwise to the nmp solution of isophthaloyl chloride (isophthaloyl chloride), and (45.68 grams of isophthaloyl chloride is molten
In 168 milliliters of NMP), after being added dropwise, in room temperature reaction 3 hours, 2 liters of deionized water is added, product is precipitated and is analysed
Out, it filters, finally toasts 72 hours with 60 DEG C in baking oven to obtain polyphenyl oxazole predecessor (I-1).
The synthesis of polyphenyl oxazole predecessor (I-2)
45.68 grams in the synthesis of polyphenyl oxazole predecessor (I-1) of isophthaloyl chloride is replaced as to 46.37 grams of 1,4- ring
Adipoyl Chloride (Isosorbide-5-Nitrae-Cyclohexanedicarbonyl dichloride), remaining step is all identical, and polyphenyl oxazole can be obtained
Predecessor (I-2).
The synthesis of polyphenyl oxazole predecessor (I-3)
45.68 grams in the synthesis of polyphenyl oxazole predecessor (I-1) of isophthaloyl chloride is replaced as to 66.40 grams of 4,4- chlorine
Formoxyl phenylate (4,4'-Oxybisbenzoyl chloride), remaining step is all identical, and polyphenyl oxazole predecessor can be obtained
(I-3)。
The photosensitive resin constituent of Examples 1 to 6 and reference examples 1 '~4 '
By polyphenyl oxazole predecessor and photosensitive compounds according to ingredient and dosage shown in table three and table four, with 1 gram
GBL, 5.5 grams of PGMEA, MPTS and 0.25 of 0.15 gram gram of F561 are mixed at normal temperature, can form embodiment 1
~6 with the photosensitive resin constituents of reference examples 1 '~4 '.
N740 is that (Phenol Novolac Type Epoxy Resin, purchase is certainly for phenol novolak type epoxy in table four
DIC Co., Ltd), weight average molecular weight (Mw) is about Isosorbide-5-Nitrae 00, and structure is as follows:
Aforementioned photosensitive resin constituent is coated on to the glass substrate of 100mm × 100mm with method of spin coating, adjusts revolving speed
The coat for forming 3.8 μm is reused baking oven and is heated 1 hour with 250 DEG C, so that coat is formed by curing photosensitive resin, and with purple
Outer light-visible spectrometry measures light transmittance, acquired results such as Fig. 3 and table five.
Referring to figure 3., light transmittance and the wavelength according to the embodiment of the present invention 1 to 4 and reference examples 1 ' and 2 ' are painted
Relational graph.From the figure 3, it may be seen that according to 1 to 4 photosensitive resin constituent of the embodiment of the present invention be formed by photosensitive resin with compare
Example 1 ' and 2 ' is compared, and all has lower light transmittance, therefore, is shown when being used as OLED with photosensitive resin constituent of the invention
Protective layer and/or pixel defining layer in element, can effectively avoid and generate light leakage between pixel, and can promote OLED display element
Contrast, and then the image quality of OLED display element can be promoted.
It is thin to see Fig. 3, it is known that 1 to 4 photosensitive resin constituent of the embodiment of the present invention is formed by photosensitive resin, for stopping wave
The long effect penetrated less than or equal to the light of 400nm is especially significant, and its light transmittance to wavelength less than or equal to 400nm is all
Less than 11%.
Referring to table five, as shown in Table 5, in the embodiment of the present invention 1 to 6, to wavelength less than or equal to 400nm's
Light transmittance is up to 6.6%, minimum 0.29%, both less than 11%, and much smaller than reference examples 1 ' to 4 ' are less than wavelength
Or the light transmittance equal to 400nm.
Existing document is pointed out at present, when the thin film transistor (TFT) in OLED diode displaying element is indium gallium zinc oxide
When thin film transistor (TFT), indium gallium zinc oxide thin film transistor (TFT) is less than, after the light irradiation equal to 400nm by wavelength, will cause
The subcritical amplitude of oscillation (sub-threshold swing, SS) in Drain current-Gate Voltage curve graph (Id-Vg Curve) produces
Changing, and influence supply OLED electric current, in turn result in brightness change and influence OLED diode displaying element at
As quality.By Fig. 3 and table five it is found that if using photosensitive resin of the invention as the guarantor in OLED diode displaying element
Sheath and/or pixel defining layer not only can avoid generating light leakage between pixel, can also effectively stop wavelength to be less than, be equal to 400nm
Light enter indium gallium zinc oxide thin film transistor (TFT), and the image quality of OLED diode displaying element can be maintained.
Table six is please referred to, according to the ingredient and dosage of table six, is mixed at normal temperature, embodiment 7~19 can be formed
With reference examples 5 '~6 ' photosensitive resin constituents, with the Ingredient Amount of embodiment 8 in table six, then 0.1 gram of dodecyl is added
Mercaptan is mixed at normal temperature, in contrast example 7 ', and with the Ingredient Amount of embodiment 8 in table six, then adds 0.15 gram
5- phenyltetrazole, be mixed at normal temperature, in contrast example 8 '.
The photosensitive resin constituent of embodiment 7~19 and reference examples 5 '~8 ' is prepared into photosensitive resin, then measures each sense
Photopolymer resin loses wavelength less than or equal to the light transmittance of 400nm, lowest exposure amount and development, by embodiment 7~19 with
And reference examples 5 '~8 ' MR1 and MR2 and aforementioned measurement be recorded in table seven.
As shown in Table 7, light transmittance of 7~19 pairs of wavelength of embodiment less than or equal to 400nm is both less than, is equal to 11%,
Obvious photosensitive resin constituent of the present invention can make that light of the wavelength less than or equal to 400nm is effectively stopped to penetrate.
By embodiment 7~11 it is found that MR1 is bigger, light transmittance of the photosensitive resin to wavelength less than or equal to 400nm is got over
Small, lowest exposure amount is bigger.By embodiment 7~11 with embodiment 12~16 it is found that the development accelerant of addition appropriate amount can drop
Low lowest exposure amount, if but the development accelerant (MR2 > 0.9) of excessive addition felt after will lead to development such as reference examples 5 '~6 '
Photopolymer resin removing, in other words, photosensitive resin constituent of the invention can effectively stop wavelength small in the case where exclusive use
It penetrates in or equal to the light of 400nm, and MR1 is bigger, blocking effect is better.In addition, photosensitive resin constituent of the invention can add
Add suitable additive, to promote other properties, for example, the development accelerant of appropriate amount can be added when MR1 value is higher,
Make made photosensitive resin with lower lowest exposure amount, to meet practical producing line demand.
By embodiment 8 and reference examples 7 ' it is found that addition sulfur alcohol compound such as lauryl mercaptan, will cause unexposed area
Photosensitive resin development loss it is excessively high, therefore it is not recommended that use.
By embodiment 8 and reference examples 8 ' it is found that addition terazole derivatives such as 5- phenyltetrazole, will cause the sense of unexposed area
Photopolymer resin development loss is excessively high, and the photosensitive resin for needing to be coated with higher caliper can just supply the thickness of loss, therefore it is not recommended that use.
Embodiment 8, embodiment 17, embodiment 18 are different from photosensitive compounds used in embodiment 19, photonasty
Close object (III-3), photosensitive compounds (V-1), photosensitive compounds (VI-1) all can be effective with photosensitive compounds (VII-1)
Reduce the light transmittance for being less than or equal to 400nm to wavelength.
Although disclosing the present invention in conjunction with embodiment of above, it is not intended to limit the invention, it is any to be familiar with this
Operator can be used for a variety of modifications and variations, therefore protection scope of the present invention without departing from the spirit and scope of the present invention
It should be subject to what the appended claims were defined.
Claims (10)
1. a kind of photosensitive resin constituent, includes:
Polyphenyl oxazole predecessor has a structure as shown in formula (I):
Wherein the X and E respectively stands alone as bivalent group, and the integer that the n is 5 to 60;And
An at least photosensitive compounds have a structure as shown in formula (II) or formula (VI):
Wherein, the R1To the R4And the R14To the R16Respectively stand alone as group shown in hydrogen, formula (i) or formula (ii), the R1To the R4
At least one of for group shown in the formula (i) or the formula (ii), the R14To the R16At least one of be the formula (i) or the formula
(ii) group shown in, the formula (i) and the formula (ii) are as follows:
Wherein the weight ratio of the photosensitive compounds and the polyphenyl oxazole predecessor is MR1, meets following condition:
0.26≤MR1≤1。
2. photosensitive resin constituent as described in claim 1, wherein the X is-C (CF3)2-、-C(CH3)2,-O- or-S-.
3. photosensitive resin constituent as described in claim 1, wherein the E is
Wherein, the R21To the R24Respectively stand alone as the alkyl of carbon number 1 to 3, the aromatic radical of carbon number 3 to 7 or naphthenic base, the m be 0 to
10 integer, the r are integer of 1 to 10.
4. photosensitive resin constituent as described in claim 1 also includes development accelerant.
5. photosensitive resin constituent as claimed in claim 4, the wherein weight of the development accelerant and the photosensitive compounds
Ratio is MR2, meets following condition:
0<MR2≤0.9。
6. a kind of photosensitive resin, by claim 1 to claim 5 it is any as described in the heated step of photosensitive resin constituent
Suddenly it is formed, makes polyphenyl oxazole predecessor cyclisation to form polyphenyl oxazole by the heating stepses.
7. photosensitive resin as claimed in claim 6, wherein the heating stepses carry out 1 hour to 5 hours in 150 DEG C to 350 DEG C.
8. photosensitive resin as claimed in claim 6, wherein the photosensitive resin is less than or equal to the light transmittance of 400nm to wavelength
Less than 11%.
9. a kind of organic light-emitting diode display element, includes:
Substrate;
Thin film transistor (TFT), the thin film transistor (TFT) are set to above the substrate;And
Photosensitive resin as claimed in claim 7, the photosensitive resin are set to above the thin film transistor (TFT).
10. organic light-emitting diode display element as claimed in claim 9, wherein the thin film transistor (TFT) is amorphous silicon transistor
(Amorphous Si TFT), low-temperature polycrystalline silicon transistor (Low Temperature Poly-Si TFT) or the oxidation of indium gallium zinc
Object thin film transistor (TFT) (Indium Gallium Zinc Oxide TFT).
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CN102016718B (en) * | 2008-05-07 | 2013-10-16 | 住友电木株式会社 | Positive-type photosensitive resin composition, cured film, protective film, insulating film, and semiconductor device and display device each comprising the cured film |
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