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CN112521296B - Diamine compound, heat-resistant resin or heat-resistant resin precursor using same, photosensitive resin composition, cured film, and display device - Google Patents

Diamine compound, heat-resistant resin or heat-resistant resin precursor using same, photosensitive resin composition, cured film, and display device Download PDF

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CN112521296B
CN112521296B CN202110158750.1A CN202110158750A CN112521296B CN 112521296 B CN112521296 B CN 112521296B CN 202110158750 A CN202110158750 A CN 202110158750A CN 112521296 B CN112521296 B CN 112521296B
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resistant resin
film
resin composition
photosensitive resin
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CN112521296A (en
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王元强
肖桂林
朱双全
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Wuhan Rouxian Technology Co ltd
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    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
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    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract

The invention provides a heat-resistant resin or precursor capable of generating ester groups for crosslinking, a photosensitive resin composition with high sensitivity and high resolution is prepared after the resin or precursor is matched with a photosensitizer, and the photosensitive resin composition has excellent thermal stability and chemical resistance after heat treatment. The present invention also provides diamine monomers represented by the general formulae (1) and (2), and the heat-resistant resin or precursor capable of forming an ester group for crosslinking contains the structure of the diamine monomer.
Figure 543448DEST_PATH_IMAGE001

Description

Diamine compound, heat-resistant resin or heat-resistant resin precursor using same, photosensitive resin composition, cured film, and display device
Technical Field
The present invention relates to a heat-resistant resin or a heat-resistant resin precursor which can form an ester group and which can be crosslinked by an ester group based on a diamine monomer, and a photosensitive resin composition and a cured film thereof, and particularly, the photosensitive resin composition can be applied to an insulating layer, a planarizing layer, a pixel defining layer of an organic light emitting element in a display device, and a protective film of a semiconductor element, an interlayer insulating film, and the like.
Background
In recent years, the development of photosensitive resin compositions which can change the solubility in a developing solution before and after exposure satisfies the requirements of patterning, and greatly promotes the rapid development of large-scale integrated circuits and display devices; with the miniaturization of semiconductor devices, even surface protective films, interlayer insulating films, and the like are required to have resolution of the order of μm or less and high sensitivity. The photosensitive resin compositions widely used at present are mainly positive-working phenolic resin/diazonaphthoquinone compound systems, such as those disclosed in patents CN101501570B, CN106933034A, CN1324401C and journal articles Novel Novolak "Block" Copolymers for Advanced i-Line resins, Stanley F.et al,J.Proc.SPIE.,1998, 3333, 1189.，New Positive-Type Photoresists Based onEnzymatically Synthesized Polyphenols ,Joji Kadota.et al, Macromol. Rapid Commun.2004, 25, 441, et al. Wherein the resin functions to provide a patterned substrate and the diazonaphthoquinone compound controls the solubility of the composition; however, such a photosensitive resin composition has a problem that the heat resistance and chemical resistance after heat treatment are insufficient due to the characteristics of the phenolic resin.
Polyimide has excellent thermal stability, mechanical properties, chemical resistance and electrical insulation properties, and thus, a polyimide-based photosensitive resin composition has been developed, and particularly, a positive photosensitive polyimide that uses an alkaline aqueous solution as a developer, has high pattern accuracy, is environmentally friendly and can be seamlessly transplanted to existing devices has been gaining attention. In order to realize the solubility of the exposed area, the polyimide resin matched with the photosensitive resist solvent diazonaphthoquinone compound needs to have good solubility, so that the introduction of phenolic hydroxyl, carboxyl and sulfonic group which can promote the alkali dissolution into the main chain structure of the polyimide is a common method. For example, patents and journal articles of the Hydroxyanide-relating reactive-type Photosensitive polymers, published under the numbers CN1275094C and CN 105820338A. Masatoshi Hasegawa .et al, J. Photopolym. Sci. Tech2007, 20, 175, et al; however, the introduction of these groups inevitably leads to a decrease in heat resistance and an increase in moisture absorption of the polyimide resinHigh, which is detrimental to its application in devices.
Disclosure of Invention
In view of the above problems, the present invention provides a heat-resistant resin or precursor capable of generating ester groups to crosslink, which can produce a photosensitive resin composition having high sensitivity and high resolution when compounded with a photoactive compound, and which, after thermal curing, has excellent thermal stability and chemical resistance because ester bonds are formed between hydroxyl groups and carboxyl groups on the resin main chain, which originally promote alkali dissolution, thereby reducing easily-cleavable sites and increasing crosslinking density.
In order to achieve the above object, a first aspect of the present invention provides a diamine compound having the general formulae (1), (2):
[ chemical formula 1]
Figure 197430DEST_PATH_IMAGE002
[ chemical formula 2]
Figure 114570DEST_PATH_IMAGE004
X in the general formulas (1) and (2) represents a 2-valent alicyclic group or aromatic group containing both a carboxyl group and a hydroxyl group; m represents an integer of 0 to 2, and p represents an integer of 0 to 2; r1Represents any one or more of hydrogen atom, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms, fluorine atom, chlorine atom and bromine atom, R2Represents any one or more of-O-, -COO-, -OCO-, -CONH-; r in general formula (1) and general formula (2)3Represents a hydrogen atom or an organic group having 1 to 8 carbon atoms.
The second aspect of the present invention provides a heat-resistant resin or a heat-resistant resin precursor having a polyimide or polyamic acid derived from the above-mentioned diamine compound structure;
as a further mode, the heat-resistant resin precursor comprises a resin having a structure represented by general formula (3);
[ chemical formula 3]
Figure 894307DEST_PATH_IMAGE005
Or/and
Figure 351834DEST_PATH_IMAGE006
or/and
Figure 166206DEST_PATH_IMAGE007
wherein in the general formula (3), Q represents 2-30 carbon atoms and contains 0-4-OH, -COOH of any organic group with 2-6 valences, D represents 2-50 carbon atoms and contains 0-4-OH, -COOH of any organic group with 2-6 valences, and R is3Represents a hydrogen atom or an organic group having 1 to 8 carbon atoms;
preferably, D in the general formula (3) represents a structure including a general formula (I) or (II);
[ chemical formula 4]
Figure 988668DEST_PATH_IMAGE009
[ chemical formula 5]
Figure 318018DEST_PATH_IMAGE010
Wherein X in the general formula (I) and (II) represents a divalent alicyclic group or aromatic group containing both a carboxyl group and a hydroxyl group; m represents an integer of 0 to 2, and p represents an integer of 0 to 2; r1Represents any one or more of hydrogen atom, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms, fluorine atom, chlorine atom and bromine atom, R2Represents any one or more of-O-, -COO-, -OCO-, -CONH-; r in general formula (1) and general formula (2)3Represents a hydrogen atom or an organic group having 1 to 8 carbon atoms.
Preferably, D in the general formula (3) comprises one or more combinations of the following structures:
Figure 516919DEST_PATH_IMAGE012
the third aspect of the present invention provides a photosensitive resin composition comprising the above heat-resistant resin or heat-resistant resin precursor (a), a photosensitizer (b), an auxiliary agent (c), and a solvent (d);
preferably, the photosensitizer (b) is a diazonaphthoquinone compound;
preferably, the auxiliary agent (c) is one or more of adhesion promoter and surfactant.
The fourth aspect of the present invention provides a cured film formed by curing the photosensitive resin composition, wherein the cured film is applied to an insulating layer, a pixel defining layer, a planarizing layer of an organic electroluminescent element, or/and a surface protective layer and an insulating layer of a semiconductor device;
a fifth aspect of the present invention provides a display device characterized by comprising the above-described cured film.
The invention has the beneficial effects that:
1. the heat-resistant resin or the heat-resistant resin precursor used by the invention contains hydroxyl and carboxyl simultaneously, the alkali solubility of the photosensitive resin composition can be effectively adjusted by controlling the proportion of the quantity of the carboxyl and the hydroxyl on the resin relative to all repeating units of the polymer, so that the photosensitive resin composition can obtain a proper dissolution rate in the developing process, and the photosensitive resin composition can realize a high dissolution rate ratio of an exposed area and a non-exposed area by matching with a photoactive dissolution inhibitor containing a diazonaphthoquinone group, so that an image with higher resolution can be obtained.
2. In the invention, the monomer structure containing both hydroxyl and carboxyl is used, so that in the process of heating to form a cured film, the hydroxyl and the carboxyl which are unstable to heat can react with each other to form relatively stable ester groups, and the crosslinking density or lactonization among resin molecules can be effectively increased, thereby obviously improving the heat resistance and the mechanical strength of the film after heat treatment and reducing the gas escape amount.
3. The highly heat-resistant film formed from the photosensitive resin composition provided in the present invention can be used for producing an insulating layer, a pixel defining layer, a planarizing layer of an organic electroluminescent element, and a protective film, an insulating film, etc. on the surface of a semiconductor element.
Detailed Description
The present invention is described in detail below:
diamine compound
The diamine compound in the present invention is a compound represented by the general formulae (1) and (2), and is a diamine compound having both a carboxyl group and a hydroxyl group (preferably a phenolic hydroxyl group here) to form a lactone group.
[ chemical formula 1]
Figure 185797DEST_PATH_IMAGE013
[ chemical formula 2]
Figure 241478DEST_PATH_IMAGE015
X in the general formulas (1) and (2) represents a 2-valent alicyclic group or aromatic group containing both carboxyl and hydroxyl; m represents an integer of 0 to 2, and p represents an integer of 0 to 2; r1Represents any one or more of hydrogen atom, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms, fluorine atom, chlorine atom and bromine atom, R2Represents any one or more of-O-, -COO-, -OCO-, -CONH-; r in general formula (1) and general formula (2)3Represents a hydrogen atom or an organic group having 1 to 8 carbon atoms;
for general formula (1): the compounds represented by the general formula (1) can be exemplified by, but not limited to, compounds based on coumarin derivatives having the structure represented by the structural formula a:
Figure 995807DEST_PATH_IMAGE016
structural formula A
R in the formula A4Represents alkyl and alkoxy with 1-3 carbon atoms and fluorine, chlorine and bromine substituents, and R is selected from the group consisting of alkyl, alkoxy, fluorine, chlorine and bromine substituents with respect to improving the hydrophobicity of the monomer4Preferably a methyl group, a methoxy group or a fluorine atom; p in the formula A represents an integer of 0 to 2, and is preferably 0 or 1 from the viewpoint of improving the solubility of the monomer in a solvent and the ease of synthesis of the monomer; r5Represents a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, and a fluorine, chlorine or bromine substituent.
Preparation method of structural formula A
The diamine compound represented by the general formula (1) can be synthesized by a known method for producing a diamine compound, and is not particularly limited; in the general formula (1), particularly under the condition shown in the structural formula A, the nitro compound precursor is selected and used in the embodiment of the invention, and the nitro compound precursor is obtained by hydrogen reduction under the catalysis of palladium carbon (Pd/C) or Raney nickel; the ester group is then hydrolyzed in an acid solution, and the following reduction reaction (shown in reaction formulae B and C) is shown as an example of a representative compound.
Figure 732819DEST_PATH_IMAGE017
Reaction formula B
The specific reaction conditions of equation B are as follows: methanol is used as a solvent, 2, 7-binitro-3, 4-benzocoumarin is dissolved in the methanol, 10wt% Pd/C with one thousandth to ten thousandth of equivalent is added under stirring, hydrogen is introduced, and the reaction is carried out for 5 to 48 hours at the temperature of 20 to 50 ℃. Pd/C is removed by filtration, and the filtrate is concentrated by rotary evaporation to obtain the product.
Figure 318521DEST_PATH_IMAGE019
Reaction formula C
The specific reaction conditions of equation C are as follows: taking a mixed solvent with the volume ratio of methanol to water of 1/0.5-1/10 as a solvent, adding 2, 7-diamino-3, 4-benzocoumarin, and adding acid under stirring at 20-80 ℃, wherein the embodiment of the invention comprises the following steps: one or more combinations of hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, methanesulfonic acid, and trifluoroacetic acid, preferably 10wt% hydrochloric acid; or adding alkali under stirring, wherein the alkali is NaOH selected to be added in the embodiment of the invention, and reacting for 5-48 h; then adjusting the pH value to be weakly acidic, and concentrating the filtrate by rotary evaporation to obtain the product.
Or directly reducing nitro compound precursor with iron/hydrochloric acid (Fe/HCl) or zinc powder/hydrochloric acid (Zn/HCl) (shown in reaction formula D)
Figure 748366DEST_PATH_IMAGE020
Reaction formula D
The specific reaction conditions of equation D are as follows: tetrahydrofuran is used as a solvent, 2, 7-dinitro-3, 4-benzocoumarin is added, 5-50 times of equivalent of iron powder or zinc powder is added, hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, methane sulfonic acid and trifluoroacetic acid are selected as acids in the embodiment of the invention, 10wt% of hydrochloric acid is preferably used, the pH value is adjusted to 1-5, and the reaction is carried out for 8-24 hours at 60-100 ℃; adjusting the pH value to be weakly acidic, preferably using a saturated sodium bicarbonate solution to adjust the pH value to be weakly acidic in the embodiment of the invention, preferably using ethanol as an organic solvent in the embodiment of the invention, washing the extraction solid by using ethanol, and concentrating the filtrate to obtain the product.
The diamine compound shown in the general formula (1) can also represent derivative amine with a structure similar to coumarin, and the specific synthetic method (shown as a reaction formula E)
Figure 989991DEST_PATH_IMAGE021
Figure 265115DEST_PATH_IMAGE022
Reaction formula E
Suspending hydrochloride of 7-aminocoumarin in n-hexane, irradiating for a certain time by a high-pressure mercury lamp, and filtering to obtain a [2+2] cyclization product of the hydrochloride of 7-aminocoumarin. The product is adjusted to neutral pH by saturated aqueous solution of sodium bicarbonate to obtain the [2+2] cyclization product of 7-aminocoumarin.
Under the protection of nitrogen flow, dissolving a [2+2] cyclization product of 7-aminocoumarin in acetonitrile, dropwise adding 0.01 mol/mL NaOH aqueous solution, heating to 60 ℃, reacting for 6 h, adjusting pH to 5-6 with dilute hydrochloric acid, extracting with ethyl acetate, and concentrating to obtain the derivative amine with the structure similar to coumarin.
For general formula (2): the compounds represented by the general formula (2) can be exemplified by those represented by the structural formula F:
Figure 970903DEST_PATH_IMAGE023
structural formula F
R in the formula F4R represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group, a fluorine, chlorine or bromine substituent, in view of improving the hydrophobicity of the monomer4Preferably methyl, methoxy and fluorine atoms; p in the formula F represents an integer of 0 to 2, and is preferably 0 or 1 from the viewpoint of improving the solubility of the monomer in a solvent and the ease of synthesis of the monomer; r5Represents a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, and a fluorine, chlorine or bromine substituent.
Process for the preparation of formula F
The synthesis of the amide bond-containing amine compound represented by the general formula (2) can be carried out by a known method for producing an amine compound, and is not particularly limited; in the general formula (2), particularly in the case shown in the structural formula F, the embodiment of the present invention can be obtained by reacting the compound obtained in the general formula (1) with nitrobenzoyl chloride or nitrobenzoic acid to obtain a nitro compound, reducing the nitro compound precursor with hydrogen under the catalysis of palladium carbon (Pd/C) or raney nickel, and then hydrolyzing the ester group in an acid solution; or directly reducing the nitro compound precursor by using iron/hydrochloric acid (Fe/HCl) or zinc powder/hydrochloric acid (Zn/HCl). Representative compounds are exemplified, the following synthetic reactions (shown in reaction formula G) are shown,
Figure 306069DEST_PATH_IMAGE024
reaction formula G
The specific reaction conditions of equation G are as follows: taking dichloromethane or chloroform as a solvent, adding 2, 7-diamino-3, 4-benzocoumarin and twice equivalent of nitrobenzyl chloride, and dropwise adding tertiary amine organic base at the temperature of not more than 10 ℃, wherein the selection of the embodiment of the invention comprises the following steps: one or more of triethylamine, pyridine and picoline are completely dripped, stirred and reacted for 5 to 24 hours at the temperature of 20 ℃, and then the solid is filtered, washed by water and recrystallized to obtain the nitro compound containing the lactone group.
Then, methanol is used as a solvent, the nitro compound is added into the mixture, 10wt% Pd/C with one to ten thousand equivalent weight is added under stirring, hydrogen is introduced, and the mixture reacts for 5 to 48 hours at the temperature of 20 to 50 ℃; then filtering to remove Pd/C, and concentrating the filtrate by rotary evaporation to obtain the diamine product containing lactone groups.
And then taking a mixed solvent of methanol and water with the volume ratio of 1/0.5-1/10 as a solvent, adding the diamine product containing the lactone group into the solvent, and adding acid under stirring at the temperature of 20-80 ℃, wherein the selection in the embodiment of the invention comprises the following steps: one or more of hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, methane sulfonic acid and trifluoroacetic acid, preferably 10wt% hydrochloric acid, or alkali, preferably NaOH, is added in the embodiment of the invention, and the reaction is carried out for 5-48 hours. Then adjusting the pH value to be weakly acidic, and concentrating the filtrate by rotary evaporation to obtain a final product containing carboxyl and hydroxyl simultaneously.
Or tetrahydrofuran is used as solvent, nitro compound containing lactone group is added into the solvent, 5-50 times of equivalent of iron powder or zinc powder is added, and the pH value can be adjusted to 1-5 by using about 10wt% hydrochloric acid and reacting for 8-24 h at 60-100 ℃ by using acid such as hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, methane sulfonic acid, trifluoro formic acid and the like. Adjusting pH to weak acid with weak base such as saturated sodium bicarbonate solution, washing the extracted solid with organic solvent such as ethanol, and concentrating the filtrate to obtain final product containing carboxyl and hydroxyl simultaneously.
Or tetrahydrofuran is used as solvent, nitro compound containing lactone group is added into the solvent, 5-50 times of equivalent of iron powder or zinc powder is added, and the pH value can be adjusted to 1-5 by using about 10wt% hydrochloric acid and reacting for 8-24 h at 60-100 ℃ by using acid such as hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, methane sulfonic acid, trifluoro formic acid and the like. Adjusting pH to weak acid with weak base such as saturated sodium bicarbonate solution, washing the extracted solid with organic solvent such as ethanol, and concentrating the filtrate to obtain final product containing carboxyl and hydroxyl simultaneously.
The synthesis of the amine compound having an ether bond represented by the general formula (2) can also be prepared based on the similar method, in the embodiment of the present invention, the nitro compound is obtained by substitution reaction of the corresponding phenolic compound with nitrohalogenobenzene, wherein the nitrohalogenobenzene may be one of nitrochlorobenzene and nitrofluorobenzene, and then reduction reaction is performed to obtain the amine compound, and the following reaction (shown as the reaction formula H) is illustrated by taking the representative compound as an example.
Figure 34991DEST_PATH_IMAGE025
Reaction formula H
The specific reaction conditions of reaction formula H are as follows: taking a strong polar aprotic solvent such as N, N-dimethyl sulfoxide and N, N-dimethylformamide as a solvent, adding 2, 7-dihydroxy-3, 4-benzocoumarin and twice equivalent of nitrochlorobenzene, and adding a base, wherein the selection in the embodiment of the invention comprises the following steps: one of potassium carbonate and sodium carbonate is stirred to react for 5-48h at 60-80 ℃, water is added, organic solvent immiscible with water is used for extraction, ethyl acetate is selected as the organic solvent in the embodiment of the invention, crude product is obtained after concentration, then water vapor distillation purification is carried out to obtain product nitro compound, and the subsequent nitro reduction method is consistent with the above method.
The synthesis of derivative amine compounds with coumarin-like structures in structural formula F can also be prepared based on the method of reaction formula E above, except that 7-aminocoumarin is replaced with other coumarin derivatives, including coumarin derivatives containing amide bonds and ether bonds within the molecule, and other methods are consistent with those in reaction formula E above.
Heat-resistant resin or heat-resistant resin precursor (a)
In a second aspect, the present invention provides a heat-resistant resin or a heat-resistant resin precursor obtained by reacting the diamine and the dianhydride as reactants.
Preferably, the heat-resistant resin or the heat-resistant resin precursor in the embodiment of the present invention has a structure represented by general formula (3).
For formula (3):
Figure 113805DEST_PATH_IMAGE026
or/and
Figure 674099DEST_PATH_IMAGE027
or/and
Figure 445746DEST_PATH_IMAGE007
in the general formula (3), Q represents an organic group having 2 to 30 carbon atoms and having a valence of 2 to 6 and containing 0 to 4-OH, -COOH or more; r3Represents a hydrogen atom or an organic group having 1 to 8 carbon atoms.
Component Q
For Q in formula (3), it preferably includes one or more combinations of the following structures:
Figure 396385DEST_PATH_IMAGE028
for Q in formula (3), the following structure is most preferred:
Figure 341207DEST_PATH_IMAGE029
component D
In the general formula (3), D represents a 2-6 valent organic group having 2 to 50 carbon atoms and containing 0 to 4-OH, -COOH, any one of ester groups, and a 2-6 valent organic group having 0 to 4-OH, -COOH, and preferably includes one or more combinations of the following structures represented by the general formulae (I), (II):
Figure 693691DEST_PATH_IMAGE030
combinations of one or more of the following structures may also be included:
Figure 636239DEST_PATH_IMAGE031
R4r represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group, a fluorine, chlorine or bromine substituent, in view of improving the hydrophobicity of the monomer4Preferably methyl, methoxy and fluorine atoms; p represents an integer of 0 to 2, and is preferably 0 or 1 from the viewpoint of improving the solubility of the monomer in a solvent and the ease of synthesis of the monomer; r5Represents a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, and a fluorine, chlorine or bromine substituent.
For D in formula (3), it may also represent a 2-6 valent organic group containing from 0 to 4 ester groups simultaneously, including one or more combinations of the following structures:
Figure 74174DEST_PATH_IMAGE032
one or more combinations of the following structures may also be included:
Figure 557108DEST_PATH_IMAGE034
R4r represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group, a fluorine, chlorine or bromine substituent, in view of improving the hydrophobicity of the monomer4Preferably methyl, methoxy and fluorine atoms; p represents an integer of 0 to 2, and is preferably 0 or 1 from the viewpoint of improving the solubility of the monomer in a solvent and the ease of synthesis of the monomer; r5Represents a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms andfluorine, chlorine, bromine substituents.
In the above-mentioned general formulae (I), (II) containing both of the 2-to 6-valent organic groups of 0 to 4-OH, -COOH, wherein the amino group is preferably in the para-position, one of the following structures is more preferably selected among the above-mentioned structures:
Figure 29677DEST_PATH_IMAGE035
most preferred is the following structure:
Figure 143127DEST_PATH_IMAGE036
in the embodiment of the invention, D can also contain other residues of conventional diamines, but the structures represented by the general formulas (I) and (II) account for the main component, and the content is more than 10 percent; conventional diamine residues which may be used include p-phenylenediamine, m-phenylenediamine, 3-carboxy-m-phenylenediamine, 3-hydroxy-m-phenylenediamine benzidine, 4' -diaminodiphenyl ether, 3, 4' -diaminodiphenyl sulfone, 4' -diaminodiphenyl sulfone, 3, 4' -diaminodiphenyl sulfide, 4' -diaminodiphenyl sulfide, 1, 4-bis (4-aminophenoxy) benzene, bis (4-aminophenoxyphenyl) sulfone, bis (3-aminophenoxy phenyl) sulfone, 1, 4-bis (4-aminophenoxy) benzene, 3 ' -dimethyl-4, 4' -diaminobiphenyl, 2 ' -dimethyl-4, 4' -diaminobiphenyl, p-phenylenediamine, 2,2 ' -bis (trifluoromethyl) -4, 4' -diaminobiphenyl, 2,3,3 ' -tetramethyl-4, 4' -diaminobiphenyl, 3,3 ', 4, 4' -tetramethyl-4, 4' -diaminobiphenyl, and one or more combinations of cycloalkyl groups and halogen atom-substituted aromatic compounds described above.
In the embodiment of the present invention, at least 1 of the heat-resistant resin or the heat-resistant resin precursor (a) selected from the structures represented by the general formulae (I) and (II) is 40 mol% or more, preferably 60 mol% or more, and more preferably 80 mol% or more; when the photosensitive resin composition of the present invention is cured using the heat-resistant resin or the heat-resistant resin precursor (a) having the above-mentioned structural components as a main component, a cured film having high heat resistance can be obtained by forming an ester bond.
In the heat-resistant resin precursor or heat-resistant resin precursor (a) in the embodiment of the present invention, in order to ensure proper solubility in an alkaline developer and good heat resistance and elongation of the resin after heat treatment, the number of repetitions of the structural unit is preferably in the range of 10 to 1000, more preferably 20 to 500 or less, and still more preferably 50 to 100; among them, the ratio of the repeating units containing both carboxyl groups and hydroxyl groups to all the repeating terminal members is preferably 10% to 100%, and more preferably 40% to 85%. The ratio of hydrophilic carboxyl and hydroxyl in the resin structure to hydrophobic groups of the resin such as aryl, alkane and the like is adjusted through the method, so that the dissolution rate of the resin in an alkaline developer is controlled, and the dissolution rate of the unexposed film in an aqueous developer is preferably 200 nm/min-3000 nm/min and the dissolution rate of the exposed film in the aqueous developer is preferably 2000 nm/min-50000 nm/min.
The weight average molecular weight Mw and the number average molecular weight Mn of the heat-resistant resin or the heat-resistant resin precursor (a) in the examples of the present invention can be easily measured as values in terms of polystyrene by Gel Permeation Chromatography (GPC), a light scattering method, a small-angle X-ray scattering method, or the like.
In addition, in order to better adjust the molecular weight of the heat-resistant resin or heat-resistant resin precursor (a) of the present invention, a certain end-capping agent may be added at the time of polymerization, and specific examples thereof may be, and are not limited to, one or more combinations of the following exemplified compounds:
monofunctional aromatic amine: 3-aminophenol, 2-aminophenol, 4-aminophenol, 3-aminobenzoic acid, 3-amino-o-methylbenzoic acid, 3-amino-m-methylbenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 1-amino-8-hydroxynaphthalene, 1-amino-7-hydroxynaphthalene, 1-amino-6-hydroxynaphthalene, 1-amino-5-hydroxynaphthalene, 1-amino-4-hydroxynaphthalene, 1-amino-3-hydroxynaphthalene, 1-amino-2-hydroxynaphthalene, 1-carboxy-8-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 3-aminobenzoic acid, 3-amino-o-methylbenzoic acid, 3-amino-m-methylbenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic, 1-carboxy-5-aminonaphthalene, 1-carboxy-4-aminonaphthalene, 1-carboxy-3-aminonaphthalene, 1-carboxy-2-aminonaphthalene, 3-amino-4, 6-dihydroxypyrimidine, 5-amino-8-hydroxyquinoline, 4-amino-8-hydroxyquinoline;
monofunctional aromatic anhydrides: maleic anhydride, phthalic anhydride, cyclohexane dicarboxylic anhydride, and cyclohexane dicarboxylic anhydride.
Monofunctional aromatic acid: benzoic acid, o-methylbenzoic acid, m-methylbenzoic acid, p-methylbenzoic acid, 2-carboxyphenol, 3-carboxyphenol, 4-carboxyphenol, 2-carboxythiophenol, 3-carboxythiophenol, 4-carboxythiophenol, carboxynaphthalene, 2-hydroxy-naphthoic acid, 3-hydroxy-naphthoic acid, 4-hydroxy-naphthoic acid, 5-hydroxy-naphthoic acid, 6-hydroxy-naphthoic acid, 7-hydroxy-naphthoic acid, 8-hydroxy-naphthoic acid, 9-hydroxy-naphthoic acid.
The above-mentioned end-capping agent, incorporated in a proportion of 0.005 to 0.5, further 0.01 to 0.4, based on the total molar amount of all the amine-based monomers and the anhydride-based monomers charged; when the amount is within the above range, a resin composition having an appropriate solution viscosity and excellent film properties can be obtained
Photosensitive resin composition
The photosensitive resin composition in the embodiment of the present invention includes: a heat-resistant resin or a heat-resistant resin precursor (a), a photosensitizer (b), an auxiliary agent (c) and a solvent (d), wherein the heat-resistant resin or the heat-resistant resin precursor (a) is the compound described above, and the description thereof is omitted.
Photosensitizer (b)
In the embodiment of the invention, the photosensitizer (b) uses a diazonaphthoquinone compound, in particular a polyhydroxy phenol compound and a diazonaphthoquinone group at 4-position or 5-position (shown as a structural formula I, R3Is hydrogen atom or 2-6 valent aryl group with 2-30 carbon atoms) through ester bond connection; when ultraviolet light irradiates the compound, the diazonaphthoquinone group is degraded and rearranged to generate an ketene structure, and the ketene structure reacts with water to generate indene acid; thereby effecting a shift in the dissolution rate (as shown in equation J).
Figure 130674DEST_PATH_IMAGE037
Structural formula I
Figure 354982DEST_PATH_IMAGE038
Reaction formula J
Wherein, the polyhydric phenol compound used for preparing the photosensitizer (b) can be bisphenol A, bisphenol AF, naphthol, trihydroxy benzophenone and phenolic resin oligomer. They may be used alone or in combination. The amount of addition thereof is 0.01 to 0.70, more preferably 0.05 to 0.50, based on the mass of the resin.
Auxiliary agent (c)
In order to improve the adhesion and film-forming property of the resin film-forming material to the substrate, the auxiliary agent (c) in the photosensitive resin composition provided by the embodiment of the invention comprises an adhesion promoter and a surfactant; wherein the adhesion promoter is preferably a silane coupling agent, and comprises one or more of methacryloxy dimethoxy methyl silane, 3-aminopropyl trimethoxy silane, vinyl trimethoxy silane and vinyl triacyloxy silane; the amount of the adhesion promoter added is 0.003 to 0.200 relative to the mass of the polymer resin. The selected surfactant is fluorine-containing surfactant, silicon-containing surfactant, acrylate surfactant, ester and ketone reagent, and ethyl lactate, ethyl acetate, methyl ethyl ketone and cyclohexanone are preferably selected in the embodiment of the invention; the amount of the surfactant added is 0.0003 to 0.05 relative to the total mass of the polymer.
Solvent (d)
The solvent (d) used in the photosensitive resin composition according to the embodiment of the present invention is a solvent with a boiling point lower than 230 ℃, and includes, but is not limited to, one or more combinations of N, N-dimethylacetamide, N-dimethylformamide, gamma butyrolactone, ethylene glycol dimethyl ether, ethylene glycol monomethyl ether, propylene glycol dimethyl ether, propylene glycol, N-butanol, cyclohexanone, ethyl lactate, and butyl lactate; the amount of the solvent to be added is 3 to 20 times, more preferably 3 to 10 times the mass of the polymer resin.
Embodiments of the present invention also relate to a cured film, wherein the cured film is formed after patterning having high heat resistance from the photosensitive resin composition provided by the present invention, and a thermal curing method of the photosensitive resin composition is not particularly limited, and a method commonly used in the art may be used. Spin coating, spray coating, roll coating, slit coating, screen printing, preferably spin coating and slit coating, are used on smooth and orderly substrates such as glass, silicon wafers and the like; the film thickness after drying is usually 0.1 to 15 μm depending on the coating method and the composition used in terms of components, viscosity, solid content, etc. Drying the coated film at 40-150 deg.c for several minutes to several hours in oven, hot plate or infrared oven; then the dried substrate is placed under an exposure machine for ultraviolet exposure, but the ultraviolet exposure is not limited to the ultraviolet exposure, electron beams or X-rays can also be used for exposure, and the exposed substrate is dissolved in an alkaline developing solution to form patterning; the selected developer includes but is not limited to at least one of aqueous solutions of tetramethylammonium hydroxide, triethylamine, diethanolamine, dimethylaminoethanol, ethylenediamine, cyclohexylamine, hexamethylenediamine, diethylaminoethanol, methylamine and dimethylamine, wherein the aqueous solution of tetramethylammonium hydroxide with 2.38wt% is preferred, and the developing time is controlled within 5 s to 600 s, preferably 5 s to 300 s according to the difference of film thickness.
Washing the developed film with water for fixing treatment, heating the film in a curing furnace to 100-500 deg.c, and heat treatment for 10 min to several hr to convert the composition into heat resistant film.
The embodiment of the invention also provides a display device which comprises the cured film.
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer and more complete, the embodiments of the present invention will be described in detail below, wherein the embodiments do not refer to specific conditions, and are performed according to conventional conditions or conditions recommended by manufacturers, and the reagents or instruments used are not referred to manufacturers, and are all conventional products commercially available.
Synthesis of monomers
Synthesis example 1
Synthesis of 4,4 '-diamino-2-hydroxy-2' -bibenzoic acid (a)
Figure 416479DEST_PATH_IMAGE039
Under the protection of a dry nitrogen flow, dissolving 2, 7-dinitro-3, 4-benzocoumarin (20 g,69.9 mmol) in 300 mL Tetrahydrofuran (THF), adding 80g reduced iron powder, dropwise adding 20 mL10wt% hydrochloric acid, heating to 80 ℃, stirring for reaction for 24h, adjusting the pH value to weak acidity with sodium carbonate, extracting with ethyl acetate, washing with water for 3 times, separating an organic phase, concentrating, and recrystallizing 4,4 '-diamino-2-hydroxy-2' -bibenzoic acid (a).
Synthesis example 2
Synthesis of 4,4 '-bis (4-aminophenyloxy) -2-hydroxy-2' -carboxybiphenyl Compound (b)
Figure 700830DEST_PATH_IMAGE040
Under the protection of a dry nitrogen stream, 2, 7-dihydroxy-3, 4-benzocoumarin (20 g,87.6 mmol) is dissolved in 300 mL of N, N-dimethylpyrrolidone (NMP), and 4-fluoro-nitrobenzene (24.7 g, 175.3 mmol), potassium carbonate (48.5 g, 350.6 mmol) are added, reacted at 50 ℃ for 10 h, poured into water, extracted with ethyl acetate, and the organic phase is concentrated to give the nitro compound.
Figure 175674DEST_PATH_IMAGE041
Dissolving the obtained 2, 7-bis (4-nitrophenyloxy) -3, 4-benzocoumarin in 500 mL of ethanol, adding 80g of reduced zinc scrap, dropwise adding 20 mL of 10wt% hydrochloric acid, heating to 50 ℃, stirring for reaction for 24h, filtering Pd/C, concentrating the filtrate, and recrystallizing to obtain the 2, 7-bis (4-aminophenyloxy) -2-hydroxy-2' -carboxybiphenyl compound (b).
Synthesis example 3
Synthesis of derivative amine with coumarin analogue structure
Figure 203673DEST_PATH_IMAGE042
Suspending hydrochloride of 7-aminocoumarin (3.9 g, 20 mmol) in 30 mL of n-hexane, irradiating for 48h by a high-pressure mercury lamp with the wavelength of 250-450 nm, and filtering to obtain a [2+2] cyclization product of the 7-aminocoumarin hydrochloride. The product is adjusted to neutral pH by saturated aqueous solution of sodium bicarbonate to obtain the [2+2] cyclization product of 7-aminocoumarin.
Synthesis of hydrolyzate (c) of amine Compound derived from coumarin analogous Structure
Figure DEST_PATH_IMAGE043
Under the protection of nitrogen flow, dissolving a [2+2] cyclization product (10 g, 31 mmol) of 7-aminocoumarin in 100 mL of acetonitrile, dropwise adding 10 mL of 0.01 mol/mL NaOH aqueous solution, heating to 60 ℃, reacting for 6 h, adjusting pH to 5-6 with dilute hydrochloric acid, extracting with ethyl acetate, and concentrating to obtain a compound (c).
Synthesis example 4 Synthesis of diazonaphthoquinone Compound (d)
Figure 385255DEST_PATH_IMAGE044
Under the protection of dry nitrogen flow, 1,1, 1-tri (4-hydroxyphenyl) ethane (30.9 g, 100 mmol) and 5-diazonaphthoquinone sulfonyl chloride (80.4 g, 300 mmol) are dissolved in 300 mL dioxane, under the condition that the system temperature is not more than 30 ℃, a reagent mixed by 50 mL dioxane/30 mL triethylamine is dripped, the reaction is carried out for 3 h, triethylamine salt is filtered out, filtrate is dripped in water, and the diazonaphthoquinone compound (d) is obtained by filtering, precipitating and drying.
Synthesis example 54 Synthesis of 4,4 '-diamino-2-hydroxy-2' -carboxylic acid methyl ester biphenyl (e)
Figure 637245DEST_PATH_IMAGE046
Under the protection of dry nitrogen flow, 2, 7-dinitro-3, 4-benzocoumarin (2.86 g, 10 mmol) is dissolved in 30 mL of methanol, sodium methoxide (1.08 g, 20 mmol) is added, the temperature is raised to 80 ℃, stirring is carried out for 24 hours, the pH value is adjusted to weak acidity by dilute hydrochloric acid, ethyl acetate is used for extraction, water is washed for 3 times, an organic phase is separated, and the crude product of 4,4 '-dinitro-2-hydroxy-2' -methyl formate biphenyl is obtained by concentration. And dissolving the crude product in 50 mL of ethanol, adding 0.1g of 10wt% Pd/C, introducing hydrogen, reacting at room temperature for 48 hours, filtering out Pd/C, concentrating, and recrystallizing to obtain 4,4 '-diamino-2-hydroxy-2' -methyl formate biphenyl (e).
Synthesis example 64, 4 '-bis (4-aminophenyloxy) -2-hydroxy-2' -carboxylic acid methyl ester biphenyl Compound (f)
Figure 537068DEST_PATH_IMAGE047
Under the protection of a dry nitrogen flow, dissolving 2, 7-bis (4-nitrophenyloxy) -3, 4-benzocoumarin (4.70 g, 10 mmol) in 50 mL of methanol, adding sodium methoxide (1.08 g, 20 mmol), heating to 80 ℃, stirring for reacting for 24h, adjusting the pH value to weak acidity by using dilute hydrochloric acid, extracting by using ethyl acetate, washing by using water for 3 times, separating an organic phase, and concentrating to obtain a crude product of a 4,4 '-bis (4-nitrophenyloxy) -2-hydroxy-2' -methyl formate biphenyl compound. And dissolving the crude product in 50 mL of ethanol, adding 0.05g of 10wt% Pd/C, introducing hydrogen, reacting at room temperature for 48 hours, filtering out Pd/C, concentrating, and recrystallizing to obtain the 4,4 '-bis (4-aminophenyloxy) -2-hydroxy-2' -methyl formate biphenyl compound benzene (f).
Heat-resistant resin or heat-resistant resin precursor, photosensitive resin composition, and production of cured film
Evaluation method
Imaging ability of composition film after heat treatment
Detecting the state of an etched line of the developed film by using SEM (JEOL JSM-6510), wherein the line with the width less than 5 microns can still be clearly etched without bending and defect; the lines with the width of 5-10 microns can be clearly etched, have no bending and have no defect; only lines with a width of more than 10 microns can be clearly etched without bending and defects.
Crack resistance of composition film after heat treatment
After the heat treatment, the developed film was observed by an optical microscope (OLS5000) to see whether or not cracks were formed at four corners of a 100X 100 μm-sized sample.
Stress resistance of composition film after heat treatment
The developed film was subjected to heat treatment, and then observed by an optical microscope (OLS5000) to see whether or not a sample having a size of 100X 100. mu.m had wrinkles.
Water absorption of composition film after Heat treatment
The heat-treated film (having a mass of more than 0.5 g) was left in a closed atmosphere having a relative humidity of 60% for 72 hours, and the change in weight of the film sample before and after the leaving was measured. WA = (W-W0)/W0100% of W whereinADenotes the water absorption, W denotes the weight after water absorption, W0The weight before water absorption is shown.
Heat resistance of composition film after heat treatment
A small amount of sample was taken and the 5% thermogravimetric temperature (T.sub.w.) of the sample was determined using a thermogravimetric analyzer (TGA, NETZSCH STA2500 Regulus)d1)。
Example 1
Preparation of film Q1
Compound (a) (2.44 g, 10 mmol), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) was dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8h, followed by addition of 0.8 equivalent of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q1.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q1, 1.66 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q1, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q1 were evaluated.
Example 2
Preparation of film Q2
Compound (b) (4.28 g, 10 mmol), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8h, followed by addition of 0.8 equivalent of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q2.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q2, 1.69 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q2, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q2 were evaluated.
Example 3
Preparation of film Q3
Compound (b) (2.57 g,6 mmol), 4 '-diaminodiphenyl ether (0.80g, 4 mmo1), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmo1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8 hours, followed by addition of 0.8 equivalents of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 hours. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q3.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q3, 1.48 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q3, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q3 were evaluated.
Example 4
Preparation of film Q4
Compound (c) (3.58 g, 10 mmol), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8h, followed by addition of 0.8 equivalent of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q4.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q4, 1.68 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q4, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q4 were evaluated.
Example 5
Preparation of film Q5
Compound (a) (1.64 g,6 mmol), 4 '-diaminodiphenyl ether (0.80g, 4 mmo1), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmo1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8 hours, followed by addition of 0.8 equivalents of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 hours. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q5.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q5, 1.63 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q5, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q5 were evaluated.
Example 6
Film Q6
Compound (c) (2.58 g,6 mmol), 4 '-diaminodiphenyl ether (0.80g, 4 mmo1), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmo1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8 hours, followed by addition of 0.8 equivalents of acetic anhydride/pyridine (v/v = 1/1), and reacted for 6 hours. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q6.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q6, 1.88 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q6, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q6 were evaluated.
Example 7
Preparation of film Q7
Compound (e) (2.58 g, 10 mmol), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8h, followed by addition of 0.5 equivalent of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q7.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q7, 1.26 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q7, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q7 were evaluated.
Example 8
Preparation of film Q8
Compound (f) (4.42 g, 10 mmol), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, reacted at room temperature for 8h, followed by addition of 0.4 equivalent of acetic anhydride/pyridine (v/v = 1/1) and reacted for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q8.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q8, 1.24 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q8, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q8 were evaluated.
Comparative example 1
Preparation of film Q9
3, 5-diamino-benzoic acid (1.52 g, 10 mmol), 2, 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) was dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, stirred at room temperature for 8h, and then warmed to 150 ℃ for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q9.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q9, 1.28 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q9, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q9 were evaluated.
Comparative example 2
Preparation of film Q10
3, 5-diamino-benzoic acid (0.76 g, 5 mmol), 4,4 '-diaminodiphenyl ether (1.00g, 5 mmol 1), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, stirred at room temperature for 8h, and then warmed to 150 ℃ for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q10.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q10, 1.28 g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q10, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q10 were evaluated.
Comparative example 3
Preparation of film Q11
2, 4-Diaminophenol (1.24 g, 10 mmol), 2, 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmol 1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a stream of dry nitrogen gas, stirred at room temperature for 8h, and then warmed to 150 ℃ for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q11.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q11, 1.60g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g N of N-dimethylacetamide. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q11, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q11 were evaluated.
Comparative example 4
Preparation of film Q12
2, 4-diaminophenol (0.62 g, 5 mmol), 4,4 '-diaminodiphenyl ether (1.00g, 5 mmo1), 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride (4.44g, 10 mmo1) were dissolved in 50g of N, N-dimethylpyrrolidone (NMP) under a dry nitrogen stream, stirred at room temperature for 8h, and then warmed to 150 ℃ for reaction for 6 h. The solution was then poured into 2L of ethanol and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum drying oven at 60 ℃ for 24h as polymer solid Q12.
A photosensitive polyimide precursor composition varnish I was obtained by weighing 4g of the obtained polymer solid Q12, 1.60g of the diazonaphthoquinone compound (d) shown above, 0.2g of vinyltrimethoxysilane, 0.1g of TEGO FLOW 300, and 0.08g of Airex 920 in 30g of butyrolactone. A photosensitive polyimide precursor film was coated on a glass plate with the varnish obtained above, exposed to light, developed, and then heat-treated at 270 ℃ for 1 hour to prepare a film Q12, and the image forming ability, crack resistance, stress resistance, water absorption, and heat resistance of the film Q12 were evaluated.
The evaluation results of examples 1 to 8 and comparative examples 1 to 4 are shown in Table 1
TABLE 1
Figure 103179DEST_PATH_IMAGE048

Claims (7)

1. A photosensitive resin composition comprising a heat-resistant resin or a heat-resistant resin precursor (a), a photosensitizer (b), an auxiliary (c), and a solvent (d);
the heat-resistant resin or heat-resistant resin precursor (a) is obtained by reacting a diamine and a dianhydride as reactants, wherein the diamine comprises one or more of the following structural formula A or structural formula F:
[ Structure A ]
Figure 609341DEST_PATH_IMAGE001
[ structural formula F ]
Figure 588798DEST_PATH_IMAGE002
R in structural formula A and structural formula F4Represents any one of methyl, methoxy or fluorine atom; p represents 0 or 1; r5Represents any of a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, and a fluorine, chlorine, or bromine substituent.
2. The photosensitive resin composition according to claim 1, wherein the heat-resistant resin or heat-resistant resin precursor comprises one or a combination of more of the structures represented by the general formula (3);
[ chemical formula 3]
Figure 368535DEST_PATH_IMAGE003
Or/and
Figure 763745DEST_PATH_IMAGE004
or/and
Figure 578117DEST_PATH_IMAGE005
wherein, in the general formula (3), Q represents a 4-valent organic group with 2-30 carbon atoms and containing any one of 0-4-OH and-COOH; d represents diamine residue of any one or more of structural formula A or structural formula F.
3. The photosensitive resin composition according to claim 2, wherein D in the general formula (3) represents a group comprising any one or more of the following structures;
Figure 462896DEST_PATH_IMAGE006
Figure 729930DEST_PATH_IMAGE007
wherein R is4Represents any one of methyl, methoxy or fluorine atom; p represents 0 or 1; r5Represents any of a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, and a fluorine, chlorine, or bromine substituent.
4. The photosensitive resin composition according to claim 3, wherein D in the general formula (3) comprises one or more combinations of the following structures:
Figure 928830DEST_PATH_IMAGE008
。
5. the photosensitive resin composition of claim 1, wherein the photosensitizer (b) is a diazonaphthoquinone compound, and the auxiliary (c) is one or more of an adhesion promoter and a surfactant.
6. A cured film obtained by curing the photosensitive resin composition according to any one of claims 1 to 5, wherein the cured film is applied to an insulating layer, a pixel defining layer, or a planarizing layer of an organic electroluminescent device, or/and a surface protective layer or an insulating layer of a semiconductor device.
7. A display device characterized by comprising the cured film according to claim 6.
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