CN113583240A - PI developing solution for flexible panel - Google Patents

PI developing solution for flexible panel Download PDF

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Publication number
CN113583240A
CN113583240A CN202110664842.7A CN202110664842A CN113583240A CN 113583240 A CN113583240 A CN 113583240A CN 202110664842 A CN202110664842 A CN 202110664842A CN 113583240 A CN113583240 A CN 113583240A
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mol
modified
flask
developer
reacting
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Inventor
何珂
戈烨铭
汤晓春
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JIANGYIN RUNMA ELECTRONIC MATERIAL CO Ltd
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JIANGYIN RUNMA ELECTRONIC MATERIAL CO Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G02F1/133723—Polyimide, polyamide-imide

Abstract

The invention discloses a PI developing solution for a flexible panel, which belongs to the technical field of PI solutions, and comprises a solvent and a modified PI, wherein the solvent is any one or a mixture of N-methyl pyrrolidone, gamma-butyrolactone and butyl carbonate in any proportion, the modified PI is prepared by polymerization reaction of a modified diamine monomer and 3,3 ', 4, 4' -benzophenone tetracarboxylic dianhydride, a main chain of the modified diamine monomer is provided with two side chains, and the side chains are provided with hydroxyl groups, so that the PI developing solution can have good compatibility with an organic solvent when being prepared, has good compatibility with an organic matter when being used, does not generate fragments when being coated on a surface with organic matter residues, has good coating effect, and effectively solves the problem that the existing PI solution is generally hydrophilic substances and is easy to diffuse unevenly on the surface with more organic matter residues, the coating effect is influenced.

Description

PI developing solution for flexible panel
Technical Field
The invention relates to the technical field of PI liquid, in particular to PI developing solution for a flexible panel.
Background
The flexible panel refers to a flexible OLED which is widely applied to intelligent electronic equipment, vehicle-mounted display and various wearable devices due to the characteristics of obvious bending performance, light weight, thinness, wide application range and the like.
The PI (polyimide) film is a uniform alignment film on the surfaces of the TFT and CF substrates, and can align liquid crystal molecules at a predetermined pretilt angle, thereby controlling the direction of light passing therethrough and achieving the display purpose by a proper driving voltage. In the actual PI film coating process, the coating effect of the PI film is often affected by the state of the TFT or CF substrate surface. PI solutions are generally hydrophilic substances, and tend to diffuse unevenly on the surface where many organic substances remain, thereby affecting the coating effect.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a PI developing solution for a flexible panel, which is used for solving the problems in the background art.
(II) technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme: a PI developing solution for a flexible panel comprises a solvent and modified PI;
the modified PI is prepared by the following steps:
adding a modified diamine monomer, 3 ', 4, 4' -benzophenonetetracarboxylic dianhydride and m-cresol into a flask, stirring for 40min at room temperature, then dropwise adding an isoquinoline catalyst, introducing nitrogen after dropwise adding, heating to 180 ℃, reacting for 18-24h, then cooling to 50 ℃, adding methanol, standing for 20min, filtering, washing for 3 times by using methanol at the temperature of 45 ℃, and then vacuum-drying for 24h at the temperature of 100 ℃ to obtain modified PI; the use ratio of the modified diamine monomer, the 3,3 ', 4, 4' -benzophenonetetracarboxylic dianhydride, the m-cresol and the isoquinoline catalyst is as follows: 0.1 mol: 0.1 mol: 1L: 25 mL;
the reaction process is as follows:
Figure BDA0003116420600000021
further, the solvent is obtained by mixing any one or more of N-methyl pyrrolidone, gamma-butyrolactone and butyl carbonate in any proportion.
Further, the dosage ratio of the solvent to the modified PI is 1 mL: 0.01 g.
Further, the modified diamine monomer is prepared by the following steps:
step S1: adding 3-chloro-5-methylphenol and 3-amino-5-methylphenol into a flask filled with toluene, introducing nitrogen, adding binaphthyl diphenyl phosphate, palladium acetate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 70 ℃, and obtaining an intermediate 1 after the reaction is finished; the dosage ratio of the 3-chloro-5-methylphenol, the 3-amino-5-methylphenol, the toluene, the binaphthyl diphenyl phosphate, the palladium acetate and the cesium carbonate is 0.01 mol: 0.01 mol: 30mL of: 0.01 g: 0.009 g: 0.01 g;
the reaction process is as follows:
Figure BDA0003116420600000031
step S2: adding the intermediate 1, parafluoronitrobenzene, potassium carbonate and toluene into a flask, introducing nitrogen, stirring, continuously heating to 140 ℃, reacting for 6-8h at 140 ℃, then heating to 160 ℃ again, continuing to react for 12h, and performing post-treatment after the reaction is finished, wherein the post-treatment step is as follows: cooling to room temperature, adding into deionized water, filtering, collecting filter residue, and recrystallizing with anhydrous ethanol to obtain intermediate 2; the dosage ratio of the intermediate 1 to the p-fluoronitrobenzene to the potassium carbonate to the toluene is 0.04 mol: 0.08 mol: 13 g: 50 mL;
the reaction process is as follows:
Figure BDA0003116420600000032
step S3: adding the intermediate 2 and deionized water into a flask, refluxing at 110 ℃, adding potassium permanganate, and continuing to perform reflux reaction for 3 hours to obtain an intermediate 3; adding the intermediate 3 and deionized water into a flask, stirring for 30min at the temperature of 45-50 ℃, then adding thionyl chloride and N, N-dimethylformamide into the flask, raising the temperature to 70 ℃, and reacting for 5h to obtain an intermediate 4; the molar ratio of the intermediate 2 to the potassium permanganate is 1:2.3, and the molar ratio of the intermediate 3 to the thionyl chloride to the N, N-dimethylformamide is 0.1 mol: 0.25 mol: 10 mL;
the reaction process is as follows:
Figure BDA0003116420600000041
step S4: adding the intermediate 4 and tetrahydrofuran into a flask, stirring for 10min, adding pyridine, adding phloroglucinol, and reacting at 40-50 ℃ for 3h to obtain an intermediate 5; the dosage ratio of the intermediate 4, tetrahydrofuran, pyridine and p-chlorobenzyl is 0.06 mol: 250mL of: 0.07 mol: 0.12 mol;
the reaction process is as follows:
Figure BDA0003116420600000042
step S5: adding the intermediate 5 and a 10% Pd/C catalyst into a flask filled with 1, 4-dioxane, introducing hydrogen while stirring, reacting at 40 ℃ for 28-30h, removing the catalyst and the solvent after the reaction is finished, and recrystallizing with absolute ethyl alcohol to obtain a modified diamine monomer; the dosage ratio of the intermediate 5, the Pd/C catalyst and the 1, 4-dioxane is 0.03 mol: 1.3 g: 300 mL;
the reaction process is as follows:
Figure BDA0003116420600000051
(III) advantageous effects
The invention provides a PI developing solution for a flexible panel, which has the following beneficial effects compared with the prior art: the preparation method comprises the steps of preparing a modified PI and mixing the modified PI with an organic solvent to prepare a PI developing solution for a flexible panel, wherein the modified PI is prepared by polymerization reaction of a modified diamine monomer and 3,3 ', 4, 4' -benzophenonetetracarboxylic dianhydride, the modified diamine monomer is prepared by reaction of active chlorine of 3-chlorine-5-methylphenol and amino of 3-amino-5-methylphenol to prepare an intermediate 1, then the intermediate 1 and p-fluoronitrobenzene are subjected to substitution reaction to prepare an intermediate 2, then methyl of the intermediate 2 is oxidized into carboxyl to prepare an intermediate 3, then the carboxyl of the intermediate 3 is substituted into an acyl chloride group under the action of thionyl chloride to prepare an intermediate 4, then acyl chloride of the intermediate 4 and one hydroxyl of phloroglucinol react to prepare an intermediate 5, and then nitro of the intermediate 5 is converted into amino, the main chain of the polyimide prepared from the modified diamine monomer is provided with two side chains, and the side chains of the polyimide have hydroxyl groups, so that the polyimide can have good compatibility with an organic solvent when a PI liquid is prepared, has good compatibility with an organic matter when used, and can also have good coating effect when coated on the surface with organic matter residues.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparing a modified diamine monomer, wherein the modified diamine monomer is prepared by the following steps:
step S1: adding 3-chloro-5-methylphenol and 3-amino-5-methylphenol into a flask filled with toluene, introducing nitrogen, adding binaphthyl diphenyl phosphate, palladium acetate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 70 ℃, and obtaining an intermediate 1 after the reaction is finished;
step S2: adding the intermediate 1, parafluoronitrobenzene, potassium carbonate and toluene into a flask, introducing nitrogen, stirring, continuously heating to 140 ℃, reacting for 6 hours at 140 ℃, then heating to 160 ℃ again, continuing to react for 12 hours, and performing post-treatment after the reaction is finished, wherein the post-treatment steps are as follows: cooling to room temperature, adding into deionized water, filtering, collecting filter residue, and recrystallizing with anhydrous ethanol to obtain intermediate 2;
step S3: adding the intermediate 2 and deionized water into a flask, refluxing at 110 ℃, adding potassium permanganate, and continuing to perform reflux reaction for 3 hours to obtain an intermediate 3; adding the intermediate 3 and deionized water into a flask, stirring for 30min at the temperature of 45 ℃, then adding thionyl chloride and N, N-dimethylformamide into the flask, raising the temperature to 70 ℃, and reacting for 5h to obtain an intermediate 4;
step S4: adding the intermediate 4 and tetrahydrofuran into a flask, stirring for 10min, adding pyridine, adding phloroglucinol, and reacting at 40 ℃ for 3h to obtain an intermediate 5;
step S5: adding the intermediate 5 and a 10% Pd/C catalyst into a flask filled with 1, 4-dioxane, introducing hydrogen while stirring, reacting at 40 ℃ for 28 hours, removing the catalyst and the solvent after the reaction is finished, and recrystallizing with absolute ethyl alcohol to obtain the modified diamine monomer.
Example 2
Preparing a modified diamine monomer, wherein the modified diamine monomer is prepared by the following steps:
step S1: adding 3-chloro-5-methylphenol and 3-amino-5-methylphenol into a flask filled with toluene, introducing nitrogen, adding binaphthyl diphenyl phosphate, palladium acetate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 70 ℃, and obtaining an intermediate 1 after the reaction is finished;
step S2: adding the intermediate 1, parafluoronitrobenzene, potassium carbonate and toluene into a flask, introducing nitrogen, stirring, continuously heating to 140 ℃, reacting for 7 hours at 140 ℃, then heating to 160 ℃ again, continuing to react for 12 hours, and performing post-treatment after the reaction is finished, wherein the post-treatment steps are as follows: cooling to room temperature, adding into deionized water, filtering, collecting filter residue, and recrystallizing with anhydrous ethanol to obtain intermediate 2;
step S3: adding the intermediate 2 and deionized water into a flask, refluxing at 110 ℃, adding potassium permanganate, and continuing to perform reflux reaction for 3 hours to obtain an intermediate 3; adding the intermediate 3 and deionized water into a flask, stirring for 30min at the temperature of 47.5 ℃, then adding thionyl chloride and N, N-dimethylformamide into the flask, raising the temperature to 70 ℃, and reacting for 5h to obtain an intermediate 4;
step S4: adding the intermediate 4 and tetrahydrofuran into a flask, stirring for 10min, adding pyridine, adding phloroglucinol, and reacting at the temperature of 45 ℃ for 3h to obtain an intermediate 5;
step S5: adding the intermediate 5 and a 10% Pd/C catalyst into a flask filled with 1, 4-dioxane, introducing hydrogen while stirring, reacting at 40 ℃ for 29 hours, removing the catalyst and the solvent after the reaction is finished, and recrystallizing with absolute ethyl alcohol to obtain the modified diamine monomer.
Example 3
Preparing a modified diamine monomer, wherein the modified diamine monomer is prepared by the following steps:
step S1: adding 3-chloro-5-methylphenol and 3-amino-5-methylphenol into a flask filled with toluene, introducing nitrogen, adding binaphthyl diphenyl phosphate, palladium acetate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 70 ℃, and obtaining an intermediate 1 after the reaction is finished;
step S2: adding the intermediate 1, parafluoronitrobenzene, potassium carbonate and toluene into a flask, introducing nitrogen, stirring, continuously heating to 140 ℃, reacting for 8 hours at 140 ℃, then heating to 160 ℃ again, continuing to react for 12 hours, and performing post-treatment after the reaction is finished, wherein the post-treatment steps are as follows: cooling to room temperature, adding into deionized water, filtering, collecting filter residue, and recrystallizing with anhydrous ethanol to obtain intermediate 2;
step S3: adding the intermediate 2 and deionized water into a flask, refluxing at 110 ℃, adding potassium permanganate, and continuing to perform reflux reaction for 3 hours to obtain an intermediate 3; adding the intermediate 3 and deionized water into a flask, stirring for 30min at the temperature of 50 ℃, then adding thionyl chloride and N, N-dimethylformamide into the flask, raising the temperature to 70 ℃, and reacting for 5h to obtain an intermediate 4;
step S4: adding the intermediate 4 and tetrahydrofuran into a flask, stirring for 10min, adding pyridine, adding phloroglucinol, and reacting at 50 ℃ for 3h to obtain an intermediate 5;
step S5: adding the intermediate 5 and a 10% Pd/C catalyst into a flask filled with 1, 4-dioxane, introducing hydrogen while stirring, reacting at 40 ℃ for 30 hours, removing the catalyst and the solvent after the reaction is finished, and recrystallizing with absolute ethyl alcohol to obtain the modified diamine monomer.
Example 4
Preparing modified PI, wherein the modified PI is prepared by the following steps:
adding the modified diamine monomer prepared in the example 2, 3 ', 4, 4' -benzophenonetetracarboxylic dianhydride and m-cresol into a flask, stirring for 40min at room temperature, then dropwise adding an isoquinoline catalyst, introducing nitrogen after dropwise adding, heating to 180 ℃, reacting for 18h, then cooling to 50 ℃, adding methanol, standing for 20min, filtering, washing for 3 times by using methanol at the temperature of 45 ℃, and then drying for 24h under vacuum at the temperature of 100 ℃ to obtain the modified PI.
Example 5
Preparing modified PI, wherein the modified PI is prepared by the following steps:
adding the modified diamine monomer prepared in the example 2, 3 ', 4, 4' -benzophenonetetracarboxylic dianhydride and m-cresol into a flask, stirring for 40min at room temperature, then dropwise adding an isoquinoline catalyst, introducing nitrogen after dropwise adding, heating to 180 ℃, reacting for 21h, then cooling to 50 ℃, adding methanol, standing for 20min, filtering, washing for 3 times by using methanol at the temperature of 45 ℃, and then drying for 24h under vacuum at the temperature of 100 ℃ to obtain the modified PI.
Example 6
Preparing modified PI, wherein the modified PI is prepared by the following steps:
adding the modified diamine monomer prepared in the example 2, 3 ', 4, 4' -benzophenonetetracarboxylic dianhydride and m-cresol into a flask, stirring for 40min at room temperature, then dropwise adding an isoquinoline catalyst, introducing nitrogen after dropwise adding, heating to 180 ℃, reacting for 24h, then cooling to 50 ℃, adding methanol, standing for 20min, filtering, washing for 3 times by using methanol with the temperature of 45 ℃, and then drying for 24h under vacuum at 100 ℃ to obtain the modified PI.
Example 7
Preparing a PI developing solution for a flexible panel, wherein the PI developing solution for the flexible panel is prepared by the following steps:
the modified PI prepared in example 5 was added to a mixed solvent of N-methylpyrrolidone, γ -butyrolactone, and butyl carbonate, and stirred at 20 ℃ for 30min to prepare a PI developer for a flexible panel.
Example 8
Preparing a PI developing solution for a flexible panel, wherein the PI developing solution for the flexible panel is prepared by the following steps:
the modified PI prepared in example 5 was added to a mixed solvent of N-methylpyrrolidone, γ -butyrolactone, and butyl carbonate, and stirred at 25 ℃ for 35min to prepare a PI developer for a flexible panel.
Example 9
Preparing a PI developing solution for a flexible panel, wherein the PI developing solution for the flexible panel is prepared by the following steps:
the modified PI prepared in example 5 was added to a mixed solvent of N-methylpyrrolidone, γ -butyrolactone, and butyl carbonate, and stirred at 30 ℃ for 40min to prepare a PI developer for a flexible panel.
Comparative example: the modified PI prepared in example 5 was not used, and PI containing no hydrophobic side chain such as a hydroxyl group was used;
the PI developers from examples 7-9 and comparative example were subjected to coating tests and observed after the coating was completed, resulting in the following table:
observation of bright spots
Example 7 No bright spot appears
Example 8 No bright spot appears
Example 9 No bright spot appears
Comparative example A large number of bright spots appear
As can be seen from the above table, the flexible panels coated with the PI developers prepared in examples 7 to 9 did not show broken bright spots, and the flexible panels coated with the PI developers prepared in comparative examples showed marked broken bright spots, and thus it was seen that the PI developers prepared in examples 7 to 9 had excellent coating and developing effects.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (10)

1. The utility model provides a PI developer solution for flexible panel which characterized in that: comprises a solvent and modified PI;
the modified PI is prepared by the following steps:
adding a modified diamine monomer, 3 ', 4, 4' -benzophenonetetracarboxylic dianhydride and m-cresol into a flask, stirring for 40min at room temperature, then dropwise adding an isoquinoline catalyst, introducing nitrogen after dropwise adding, heating to 180 ℃, reacting for 18-24h, then cooling to 50 ℃, adding methanol, standing for 20min, filtering, washing for 3 times by using methanol at the temperature of 45 ℃, and then vacuum-drying for 24h at the temperature of 100 ℃ to obtain the modified PI.
2. The PI developer according to claim 1, wherein: the solvent is obtained by mixing any one or more of N-methyl pyrrolidone, gamma-butyrolactone and butyl carbonate in any proportion.
3. The PI developer according to claim 1, wherein: the dosage ratio of the solvent to the modified PI is 1 mL: 0.01 g.
4. The PI developer according to claim 1, wherein: the use ratio of the modified diamine monomer, the 3,3 ', 4, 4' -benzophenonetetracarboxylic dianhydride, the m-cresol and the isoquinoline catalyst is as follows: 0.1 mol: 0.1 mol: 1L: 25 mL.
5. The PI developer according to claim 1, wherein: the modified diamine monomer is prepared by the following steps:
step S1: adding 3-chloro-5-methylphenol and 3-amino-5-methylphenol into a flask filled with toluene, introducing nitrogen, adding binaphthyl diphenyl phosphate, palladium acetate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 70 ℃, and obtaining an intermediate 1 after the reaction is finished;
step S2: adding the intermediate 1, parafluoronitrobenzene, potassium carbonate and toluene into a flask, introducing nitrogen, stirring, continuously heating to 140 ℃, reacting for 6-8h at 140 ℃, heating to 160 ℃ again, continuing to react for 12h, and performing post-treatment after the reaction is finished to obtain an intermediate 2;
step S3: adding the intermediate 2 and deionized water into a flask, refluxing at 110 ℃, adding potassium permanganate, and continuing to perform reflux reaction for 3 hours to obtain an intermediate 3; adding the intermediate 3 and deionized water into a flask, stirring for 30min at the temperature of 45-50 ℃, then adding thionyl chloride and N, N-dimethylformamide into the flask, raising the temperature to 70 ℃, and reacting for 5h to obtain an intermediate 4;
step S4: adding the intermediate 4 and tetrahydrofuran into a flask, stirring for 10min, adding pyridine, adding phloroglucinol, and reacting at 40-50 ℃ for 3h to obtain an intermediate 5;
step S5: adding the intermediate 5 and a 10% Pd/C catalyst into a flask filled with 1, 4-dioxane, introducing hydrogen while stirring, reacting at 40 ℃ for 28-30h, removing the catalyst and the solvent after the reaction is finished, and recrystallizing with absolute ethyl alcohol to obtain the modified diamine monomer.
6. The PI developer for flexible panels according to claim 5, wherein: the dosage ratio of the 3-chloro-5-methylphenol, the 3-amino-5-methylphenol, the toluene, the binaphthyl diphenyl phosphate, the palladium acetate and the cesium carbonate in the step S1 is 0.01 mol: 0.01 mol: 30mL of: 0.01 g: 0.009 g: 0.01 g.
7. The PI developer for flexible panels according to claim 5, wherein: the dosage ratio of the intermediate 1, the parafluoronitrobenzene, the potassium carbonate and the toluene in the step S2 is 0.04 mol: 0.08 mol: 13 g: 50 mL.
8. The PI developer for flexible panels according to claim 5, wherein: in the step S3, the molar ratio of the intermediate 2 to the potassium permanganate is 1:2.3, and the molar ratio of the intermediate 3 to the thionyl chloride to the N, N-dimethylformamide is 0.1 mol: 0.25 mol: 10 mL.
9. The PI developer for flexible panels according to claim 5, wherein: in the step S4, the dosage ratio of the intermediate 4, the tetrahydrofuran, the pyridine to the p-chlorobenzyl is 0.06 mol: 250mL of: 0.07 mol: 0.12 mol.
10. The PI developer for flexible panels according to claim 5, wherein: the dosage ratio of the intermediate 5, the Pd/C catalyst and the 1, 4-dioxane in the step S5 is 0.03 mol: 1.3 g: 300 mL.
CN202110664842.7A 2021-06-16 2021-06-16 PI developing solution for flexible panel Pending CN113583240A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185471A (en) * 1991-03-15 1993-02-09 Occidental Chemical Corporation Method for ether formation
CN1434099A (en) * 2002-01-25 2003-08-06 中国科学院化学研究所 Fluorine containing polyamic acid liquid crystal orientation agent and preparation method and use thereof
CN105182703A (en) * 2015-09-25 2015-12-23 江阴润玛电子材料股份有限公司 Novel organic negative photoresist developing liquid and preparation method thereof
CN108640846A (en) * 2018-04-25 2018-10-12 哈尔滨工业大学 A kind of flexible aromatic diamine monomers of the side group containing aromatic ring and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185471A (en) * 1991-03-15 1993-02-09 Occidental Chemical Corporation Method for ether formation
CN1434099A (en) * 2002-01-25 2003-08-06 中国科学院化学研究所 Fluorine containing polyamic acid liquid crystal orientation agent and preparation method and use thereof
CN105182703A (en) * 2015-09-25 2015-12-23 江阴润玛电子材料股份有限公司 Novel organic negative photoresist developing liquid and preparation method thereof
CN108640846A (en) * 2018-04-25 2018-10-12 哈尔滨工业大学 A kind of flexible aromatic diamine monomers of the side group containing aromatic ring and preparation method thereof

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