CN106588923A - Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof - Google Patents

Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof Download PDF

Info

Publication number
CN106588923A
CN106588923A CN201611046631.2A CN201611046631A CN106588923A CN 106588923 A CN106588923 A CN 106588923A CN 201611046631 A CN201611046631 A CN 201611046631A CN 106588923 A CN106588923 A CN 106588923A
Authority
CN
China
Prior art keywords
naphthalimide
perfluoroalkyl
perfluoroalkyl group
preparation
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201611046631.2A
Other languages
Chinese (zh)
Inventor
袁忠义
李超
蔡春生
陈士肖
胡昱
陈义旺
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanchang University
Original Assignee
Nanchang University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nanchang University filed Critical Nanchang University
Priority to CN201611046631.2A priority Critical patent/CN106588923A/en
Publication of CN106588923A publication Critical patent/CN106588923A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems

Abstract

The invention discloses perfluoroalkyl group modified solution-processable naphthalimide and a preparation method thereof, the structural formula of the naphthalimide is shown by the formula A (the formula is shown in the description), wherein the R in the formula A represents perfluoroalkyl group substituent group, which is specifically shown as the formula B, and m is selected from 1, 2, 3, 4, 5 and 6; n is selected from 1, 3, 5 and 7; X is H, Cl or Br; the preparation method of the naphthalimide comprises the steps that halogenated 1,4,5,8-Naphthalenetetracarboxylic dianhydride and the perfluoroalkyl group are taken as the starting raw materials, the mole ratio is (1:1)-(1:10), in an organic solvent, the mixture is stirred for 1-24 h under the protection of argon or nitrogen in the temperature range from the room temperature to the backflow temperature of the used solvent, the 1,4,5,8-Naphthalenetetracarboxylic dianhydride and the perfluoroalkyl group are in reaction, and the perfluoroalkyl group modified naphthalimide is generated. According to the perfluoroalkyl group modified solution-processable naphthalimide and the preparation method thereof, the alkyl group and the perfluoroalkyl group are introduced simultaneously on the matrix of the naphthalimide, the solubility of the material in the organic solvent can be enhanced remarkably, and at the same time, the light and heat stability of the naphthalimide and the device stability of the naphthalimide in the field effect transistor are enhanced.

Description

Perfluoroalkyl modification, the naphthalimide of solution processable and preparation method thereof
Technical field
The invention belongs to organic chemical industry and field of fine chemical, and in particular to perfluoroalkyl modification, the naphthalene of solution processable Acid imide and preparation method thereof.
Background technology
Compared with wide variety of inorganic semiconductor, the advantage of organic semiconducting materials is as follows：It is adapted to the solution of low cost Processing；Flexible wearable equipment can be prepared；Species is more, property is various, beneficial to designing and developing for new material and new device.
Perfluoroalkyl has rigid rod structure.There is high stability, resist containing fluorine atom and all-fluoroalkyl compound Oxidisability and hydrophobicity, fluorine atom can strengthen the phase interaction between molecule to form intermolecular hydrogen bonding with neighbouring hydrogen atom With (J.Am.Chem.Soc.1969,91,6235-6237).Fluorine atom or perfluoroalkyl are extensive in organic photoelectric field Using such as fluorine atom is used for acceptor material (the Progress in Polymer Science of active isomer phase hetero-junction solar cell 2015,47,70-91), perfluoroalkyl be used for build air-stable field-effect transistor materials (Chem.Rev.2011, 112,2208-2267)。
The naphthalimide that perfluoroalkyl is directly modified is proved to be excellent organic semiconducting materials, the introducing of perfluoroalkyl Significantly enhance the stability (Nature 2000,404,478-481) in material scene effect transistor, but such material Dissolubility in organic solvent is poor, is not suitable for solution processing.Therefore be badly in need of exploitation one class perfluoroalkyl modification, can solution add The naphthalimide of work.
The content of the invention
The purpose of the present invention is that the alkyl and perfluoroalkyl synthesis one that different proportion is introduced on the N atoms of naphthalimide is The naphthalimide of the perfluoroalkyl modification of row solution processable, to improve naphthoyl imide compounds Dui Guang ﹑ heat stability, while Improve such material dissolubility in organic solvent.
The technical scheme is that, perfluoroalkyl modification, the naphthalimide of solution processable and preparation method thereof are as follows.
With Isosorbide-5-Nitrae, 5,8- naphthalenetetracarbacidic acidic acid anhydrides or the bromo- Isosorbide-5-Nitrae of 2,6- bis-, 5,8- naphthalenetetracarbacidic acidic acid anhydrides or the chloro- Isosorbide-5-Nitrae of 2,6- bis-, 5,8- Naphthalenetetracarbacidic acidic acid anhydride reacts with perfluoroalkyl amine, obtains perfluoroalkyl naphthalimide, the knot of target product perfluoroalkyl naphthalimide Structure formula is as shown in A formulas：
Wherein, R represents alkyl substituent in A formulas, and concrete such as B formulas, m takes from 1,2,3,4,5,6；N takes from 1,3,5,7；X is H, Cl or Br.
The raw material Isosorbide-5-Nitrae that the present invention is used, 5,8- naphthalenetetracarbacidic acidic acid anhydrides, the bromo- Isosorbide-5-Nitraes of 2,6- bis-, 5,8- naphthalenetetracarbacidic acidic acid anhydrides and 2,6- Two chloro- Isosorbide-5-Nitraes, 5,8- naphthalenetetracarbacidic acidic acid anhydrides be commercial goods, perfluoroalkyl amine according to literature method (Org.Lett.2007,9, 2673-2676, Chinese J.Chem., 2004,22,371-376) prepare.
The preparation method of the naphthalimide of described perfluoroalkyl modification, it is characterised in that the method with halo Isosorbide-5-Nitrae, 5, 8- naphthalenetetracarbacidic acidics acid anhydride and perfluoroalkyl amine are initiation material, and their mol ratio is 1:1～1:10, in organic solvent, room temperature To within the temperature range of the reflux temperature of solvent for use, in 1～24h of argon or stirred under nitrogen atmosphere, Isosorbide-5-Nitrae, 5,8- naphthalene tetramethyls Anhydride reacts with perfluoroalkyl amine, generates the naphthalimide of perfluoroalkyl modification.
Described organic solvent is selected from o-Dimethylbenzene, Si hydrogen Fu Nan ﹑ N, N- bis- methyl Jia Xian An ﹑ bis- Jia base Ya Feng ﹑ ice vinegar The Suan ﹑ Mi Zuo ﹑ Kui Lin ﹑ Isosorbide-5-Nitraes-ring of dioxa six.
The beneficial effect of the invention is introduced simultaneously after alkyl and perfluoroalkyl on the parent of naphthalimide, can be notable Increase such material dissolubility in organic solvent, while strengthening the device in its photo and thermal stability and scene effect transistor Stability.
Specific embodiment
Perfluoroalkyl of the present invention is modified with reference to specific embodiment, the naphthalimide of solution processable and Its preparation method is described further, but protection scope of the present invention is not limited to this.
The N of embodiment 1, N'- bis- (2- perfluoro hexyl -1- hexyl ethyls) naphthalimide (8a)
Add compound 6 (0.268g, 1mmol), compound 5a (1.342g, 3mmol), DMF in 25mL two-mouth bottles (15mL), 2.5h is reacted at 145 DEG C, is cooled to room temperature, neutralized with 2mol/L HCl, use CH2Cl2Extraction, uses saturated aqueous common salt Washing, anhydrous magnesium sulfate is dried, sucking filtration, revolving, dichloromethane and petroleum ether post separation, obtain white solid 8a (0.411g, 36.5%).1HNMR(400MHz,CDCl3)δH:8.72-8.80(d,4H),5.68(m,2H),3.27-3.37(m,2H),2.21- 2.57(m,4H),1.90-2.01(d,2H),1.21-1.31(m,16H),0.82-0.84(m,6H)；HRMS(MALDI-TOF): Calcd for C42H36F26N2O4 1126.2260,found:1126.2278(M-)。
The N of embodiment 2, N'- bis- (2- perfluoro butyl -1- hexyl ethyls) naphthalimide (8b)
Add compound 6 (0.801g, 3mmol), compound 5b (3.125g, 9mmol), DMF in 100mL two-mouth bottles (30mL), 2.5h is reacted at 145 DEG C, is cooled to room temperature, neutralized with 2mol/LHCl, use CH2Cl2Extraction, uses saturated aqueous common salt Washing, anhydrous magnesium sulfate is dried, sucking filtration, revolving, dichloromethane and petroleum ether post separation, obtain white solid 8b (1.281g, 40%).1HNMR(400MHz,CDCl3)δH:8.73-8.80(d,4H),5.68(m,2H),3.29-3.37(m,2H),2.21- 2.58(m,2H),1.91-2.01(d,2H),1.21-1.34(m,16H),0.81-0.84(m,6H)；HRMS(MALDI-TOF): Calcd for C38H36F18N2O4926.2388, found:926.2396(M-)。
The N of embodiment 3, N'- bis- (2- perfluoro hexyl -1- butyl ethyls) naphthalimide (8c)
In 25mL two-mouth bottles plus compound 6 (0.536g, 2.102mmol), compound 5c (2.515g, 8.405mmol), DMF (15mL), at 130 DEG C 2.5h is reacted, and is cooled to room temperature, is neutralized with 2mol/LHCl, uses CH2Cl2Extraction, uses saturated common salt Water washing, anhydrous magnesium sulfate is dried, sucking filtration, revolving, dichloromethane and petroleum ether post separation, obtain white solid 8c (1.608g, 75%).1HNMR(400MHz,CDCl3)δH:8.73-8.80(d,4H),5.67(m,2H),3.29-3.37(m,2H),2.21- 2.58(m,4H),1.91-2.01(d,2H),1.21-1.34(m,8H),0.82-0.85(m,6H)；HRMS(MALDI-TOF): Calcd for C38H28F26N2O4 1070.1634,found:1070.1656(M-)。
The N of embodiment 4, N'- bis- (2- perfluoro butyl -1- butyl ethyls) naphthalimide
In 25mL two-mouth bottles plus compound 6 (0.536g, 2.010mmol), compound 5d (1.914g, 6.302mmol), DMF (15mL), at 130 DEG C 2.5h is reacted, and is cooled to room temperature, is neutralized with 2mol/LHCl, uses CH2Cl2Extraction, uses saturated common salt Water washing, anhydrous magnesium sulfate is dried, sucking filtration, revolving, dichloromethane and petroleum ether post separation, obtain white solid 8d (1.386g, 80%).1HNMR(400MHz,CDCl3)δH:8.73-8.80(d,4H),5.67(m,2H),3.29-3.37(m,2H),2.21- 2.58(m,4H),1.91-2.01(d,2H),1.21-1.34(m,8H),0.82-0.85(m,6H)；HRMS(MALDI-TOF): Calcd for C34H28F18N2O4 870.1762,found:870.1776(M-)。
Embodiment 52, the bromo- N of 6- bis-, N'- bis- (2- perfluoro hexyl -1- hexyl ethyls) naphthalimide (9a)
Add compound 7 (0.574g, 1.35mmol), compound 5a (2.762g, 7.9mmol), ice in 100mL two-mouth bottles Acetic acid 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of solvent, crosses post point From, obtain faint yellow solid 9a (0.242g, 16.8%).1HNMR(400MHz,CDCl3)δH:8.96-9.04(d,2H),5.68(m, 2H),3.26-3.37(m,2H),2.28-2.57(m,4H),1.90-2.01(d,2H),1.24-1.30(m,16H),0.82- 0.84(m,6H)；HRMS(MALDI-TOF):Calcd for C42H34Br2F26N2O4 1282.0470,found:1282.0484 (M-)。
Embodiment 62, the bromo- N of 6- bis-, N'- bis- (2- perfluoro butyl -1- hexyl ethyls) naphthalimide (9b)
In 100mL two-mouth bottles plus compound 7 (0.613g, 1.441mmol), compound 5b (1.823g, 4.072mmol), glacial acetic acid 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of Solvent, with recrystallizing methanol, obtain faint yellow solid 9b (0.259g, 14%).1HNMR(400MHz,CDCl3)δH:8.98-9.05 (d,2H),5.68(s,2H),3.26-3.33(m,2H),2.28-2.58(m,4H),1.90-2.01(d,2H),1.23-1.31 (m,16H),0.82-0.84(m,6H)；HRMS(MALDI-TOF):Calcd for C38H34Br2F18N2O4 1082.0598, found:1082.0586(M-)。
Embodiment 72, the bromo- N of 6- bis-, N'- bis- (2- perfluoro hexyl -1- butyl ethyls) naphthalimide (9c)
In 100mL two-mouth bottles plus compound 7 (0.613g, 1.440mmol), compound 5c (1.810g, 4.320mmol), glacial acetic acid 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of Solvent, with recrystallizing methanol, obtain faint yellow solid 9c (0.406g, 23%).1HNMR(400MHz,CDCl3)δH:8.98-9.05 (d,2H),5.68(s,2H),3.26-3.33(m,2H),2.28-2.58(m,4H),1.90-2.01(d,2H),1.23-1.31 (m,8H),0.82-0.84(m,6H)；HRMS(MALDI-TOF):Calcd for C38H26Br2F26N2O4 1225.9844, found:1225.9856(M-)。
Embodiment 82, the bromo- N of 6- bis-, N'- bis- (2- perfluoro butyl -1- butyl ethyls) naphthalimide (9d)
In 100mL two-mouth bottles plus compound 7 (0.639g, 1.501mmol), compound 5d (1.436g, 4.505mmol), glacial acetic acid 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of Solvent, with recrystallizing methanol, obtain faint yellow solid 9d (0.514g, 25%).1HNMR(400MHz,CDCl3)δH:8.98-9.05 (d,2H),5.68(s,2H),3.26-3.33(m,2H),2.28-2.58(m,4H),1.90-2.01(d,2H),1.23-1.31 (m,8H),0.82-0.84(m,6H)；HRMS(MALDI-TOF):Calcd for C34H26Br2F18N2O4 1025.9972, found:1025.9986(M-)。
Embodiment 92, the chloro- N of 6- bis-, N'- bis- (2- perfluoro hexyl -1- hexyl ethyls) naphthalimide (10a)
Add compound 8 (0.674g, 2mmol) in 100mL two-mouth bottles, compound 5a (g, 5mmol), glacial acetic acid 8mL are adjacent Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of solvent, with recrystallizing methanol, obtains light Yellow solid 10a (0.670g, 28%).HRMS(MALDI-TOF):Calcd for C42H34Cl2F26N2O4 1194.1480, found:1194.1495(M-)。
Embodiment 10 2, the chloro- N of 6- bis-, N'- bis- (2- perfluoro butyl -1- hexyl ethyls) naphthalimide (10b)
Add compound 8 (0.674g, 2mmol), compound 5b (1.736g, 5mmol), glacial acetic acid in 100mL two-mouth bottles 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of solvent, tied again with methanol Crystalline substance, obtain faint yellow solid 10b (0.418g, 21%).HRMS(MALDI-TOF):Calcd for C38H34Cl2F18N2O4 994.1608,found:994.1615(M-)。
Embodiment 11 2, the chloro- N of 6- bis-, N'- bis- (2- perfluoro hexyl -1- butyl ethyls) naphthalimide (10c)
Add compound 8 (0.674g, 2mmol), compound 5c (2.096g, 5mmol), glacial acetic acid in 100mL two-mouth bottles 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of solvent, tied again with methanol Crystalline substance, obtain faint yellow solid 10c (0.706g, 31%).HRMS(MALDI-TOF):Calcd for C38H26Cl2F26N2O4 1138.0854,found:1138.0866(M-)。
Embodiment 12 2, the chloro- N of 6- bis-, N'- bis- (2- perfluoro butyl -1- butyl ethyls) naphthalimide (10d)
Add compound 8 (0.674g, 2mmol), compound 5d (1.596g, 5mmol), glacial acetic acid in 100mL two-mouth bottles 8mL, o-Dimethylbenzene 24mL, at 130 DEG C 2.5h is reacted, and is cooled to room temperature, and revolving removes most of solvent, tied again with methanol Crystalline substance, obtain faint yellow solid 10d (0.451g, 24%).HRMS(MALDI-TOF):Calcd for C34H26Cl2F18N2O4 938.0982,found:938.0993(M-)。

Claims (3)

1. perfluoroalkyl modification, the naphthalimide of solution processable, it is characterised in that：Its general structure such as A formulas：
Wherein, R represents perfluoroalkyl substituents in A formulas, and concrete such as B formulas, m takes from 1,2,3,4,5,6；N takes from 1,3,5,7；X is H, Cl or Br.
2. perfluoroalkyl modification, the preparation method of the naphthalimide of solution processable, it is characterised in that：The method with halo Isosorbide-5-Nitrae, 5,8- naphthalenetetracarbacidic acidic acid anhydrides and perfluoroalkyl amine are initiation material, and their mol ratio is 1:1～1:10, in organic solvent, room Temperature is arrived within the temperature range of the reflux temperature of solvent for use, in 1～24h of argon or stirred under nitrogen atmosphere, Isosorbide-5-Nitrae, 5,8- naphthalenes four Formic anhydride reacts with perfluoroalkyl amine, generates the naphthalimide of perfluoroalkyl modification.
3. perfluoroalkyl according to claim 2 modification, the preparation method of the naphthalimide of solution processable, its feature exists In：Described organic solvent is selected from o-Dimethylbenzene, Si hydrogen Fu Nan ﹑ N, N- bis- methyl Jia Xian An ﹑ bis- Jia base Ya Feng ﹑ Bing Cu Suan ﹑ miaows The Zuo ﹑ Kui Lin ﹑ Isosorbide-5-Nitraes-ring of dioxa six.
CN201611046631.2A 2016-11-23 2016-11-23 Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof Pending CN106588923A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201611046631.2A CN106588923A (en) 2016-11-23 2016-11-23 Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201611046631.2A CN106588923A (en) 2016-11-23 2016-11-23 Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof

Publications (1)

Publication Number Publication Date
CN106588923A true CN106588923A (en) 2017-04-26

Family

ID=58593078

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201611046631.2A Pending CN106588923A (en) 2016-11-23 2016-11-23 Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof

Country Status (1)

Country Link
CN (1) CN106588923A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107602822A (en) * 2017-08-01 2018-01-19 南昌大学 Naphthalimide conjugated polymer of perfluoroalkyl modification and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105237746A (en) * 2015-10-29 2016-01-13 中国科学院化学研究所 Polymer semiconductor material constructed based on diketopyrrolopyrrole and naphthalimide units and application method for polymer semiconductor material and application of polymer semiconductor material

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105237746A (en) * 2015-10-29 2016-01-13 中国科学院化学研究所 Polymer semiconductor material constructed based on diketopyrrolopyrrole and naphthalimide units and application method for polymer semiconductor material and application of polymer semiconductor material

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
M. STOLTE ET AL.: "Organic n-Channel Thin-Film Transistors Based on Dichlorinated Naphthalene Diimides", 《PROC. OF SPIE》 *
YU-YI HSU ET AL.: "Dendrons with urea/malonamide linkages for gate insulators of n-channel organic thinfilm transistors", 《REACTIVE AND FUNCTIONAL POLYMERS》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107602822A (en) * 2017-08-01 2018-01-19 南昌大学 Naphthalimide conjugated polymer of perfluoroalkyl modification and preparation method thereof

Similar Documents

Publication Publication Date Title
CN106083891B (en) The manufacture method of compound with hiv integrase inhibitory activity
Kitamura et al. 2-Azido-1, 3-dimethylimidazolinium salts: Efficient diazo-transfer reagents for 1, 3-dicarbonyl compounds
WO2012142466A1 (en) Stannyl derivatives of naphthalene diimides and related compositions and methods
JP2004161601A5 (en)
PT868423E (en) METHOD FOR SYNTHESIS OF A BENZIMIDAZOLE COMPOUND
He et al. Selective thienylation of fluorinated benzothiadiazoles and benzotriazoles for organic photovoltaics
EP1897875A1 (en) Process for producing 1-pyridin-4-YL-indoles
Ishii et al. Facile preparation of ionic liquid containing silsesquioxane framework
CN106749020B (en) A kind of synthetic method of 3- acyl group quinolines
CN106588923A (en) Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof
JPH0288586A (en) Organic functional betaine modified siloxane and its production
CN114057775A (en) Super-base material, preparation method thereof and organic light-emitting diode
CN106588924A (en) Perfluoroalkyl-modified perylene imide and its preparation method
CN107935925B (en) Preparation method of polysubstituted phenanthridine compound
CN103554146B (en) Fire retardant match gram three silicic acid chlorine bromine propyl ester compounds and preparation method thereof
US10844081B2 (en) Protected organoboronic acids with tunable reactivity, and methods of use thereof
CN110467628A (en) A kind of semiconductor material and the preparation method and application thereof
JP2015509913A (en) Reaction products of stannyl derivatives of naphthalene diimides with rylene compounds
CN102558033B (en) Organic-inorganic composite material based on 4, 4'-bipyridyl and preparation method and application thereof
Jiang et al. Synthesis and properties of amorphous hole transport materials of triphenylamine based trihydrazones
CN102002047B (en) Phthalocyanine compound and organic thin film transistor
CN107417623B (en) Method for synthesizing 5-diarylaminobenzimidazole derivative in one step
CN110407830A (en) A method of synthesis N- aryl phenothiazine compound
CN110343047B (en) Preparation method of aminopyrene compound
CN108503572A (en) A kind of synthetic method of 3- acyl pyrrolines class compound

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20170426

WD01 Invention patent application deemed withdrawn after publication