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CN105198875B - A kind of new aromatic amine compound and its preparation and application - Google Patents

A kind of new aromatic amine compound and its preparation and application Download PDF

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CN105198875B
CN105198875B CN201510546022.2A CN201510546022A CN105198875B CN 105198875 B CN105198875 B CN 105198875B CN 201510546022 A CN201510546022 A CN 201510546022A CN 105198875 B CN105198875 B CN 105198875B
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aromatic amine
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CN105198875A (en
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高春吉
王士凯
张成成
王贺
崔敦洙
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Olide (shanghai) Photoelectric Material Technology Co Ltd
Shanghai Sheng Xi Photoelectric Technology Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses a kind of new aromatic amine compound, its compound molecule formula is：Wherein, R1、R2、R3It is the one kind in the heterocyclic radical of aryl or carbon number 5~50 or the aromatic series amido of carbon number 6~30 of hydrogen atom or the alkyl of carbon number 1~30 or carbon number 6~50；Ar1、Ar2It is the one kind in the aryloxy group aromatic thiohydroxy of the aryloxy group or carbon number 6~50 of the aryl of the alkane aromatic thiohydroxy or carbon number 6~50 of hydrogen atom or the alkaryl of carbon number 7~50 or the aryloxy alkyl of carbon number 7~50 or carbon number 7~50 or the heterocyclic radical of carbon number 5~50 or the aromatic series amido of carbon number 6~30 or carbon number 6~50.This heteroaromatic compounds are used to make organic electroluminescence device, the features such as the device of new heterocycle derivative manufacture possesses brightness high, outstanding heat resistance, long-life and high efficiency.

Description

Novel aromatic amine compound and preparation and application thereof
Technical Field
The invention relates to the field of electroluminescent materials, in particular to a novel aromatic amine compound and preparation and application thereof.
Background
The main materials of the electroluminescent device mainly include small molecule main materials and polymer main materials. Many efficient electroluminescent devices have been prepared using small molecule host materials doped with phosphorescent complexes as the light emitting layer. In recent years, the preparation of electroluminescent devices by doping various phosphorescent complex guests with polymer host materials as light-emitting layers has attracted much attention. Due to rapid development in the fields of optoelectronic communication and multimedia in recent years, organic optoelectronic materials have become the core of the information and electronics industries of modern society.
The organic electroluminescent device (OLED) is a novel flat display device, and compared with the small-molecule electroluminescent device, the organic electroluminescent device has the characteristics of energy conservation, high response speed, stable color, strong environmental adaptability, no radiation, long service life, light weight, thin thickness and the like. Organic electroluminescent devices generally consist of two opposing electrodes and at least one layer of an organic light-emitting compound interposed between the two electrodes. Electric charges are injected into an organic layer formed between an anode and a cathode to form electron and hole pairs, causing an organic compound having fluorescent or phosphorescent characteristics to generate light emission. When a voltage is applied between the anode and the cathode, holes are injected from the anode into the light-emitting layer through the hole transport layer, and electrons are injected from the cathode into the light-emitting layer through the electron transport layer. In the light emitting layer region, carriers are rearranged to form excitons. The excited excitons are shifted to the ground state, causing the light-emitting layer molecules to emit light, and thus an image is formed.
Representative materials of hole transport materials in current organic electroluminescent devices are as follows:
the characteristics of the materials required at present are that the materials have thermal stability, fast electron mobility, high efficiency of the luminophor and long service life, but the performances of the existing materials are general.
Disclosure of Invention
The invention aims to provide a novel aromatic amine compound, and preparation and application thereof, which are hole transport materials with good luminous efficiency, the electron mobility is improved by a pyrido [3,2-g ] quinoline compound, and a device is prepared from a new heterocyclic compound diffraction substance, so that the device has good luminous efficiency.
The invention adopts the following technical scheme:
the invention provides a novel aromatic amine compound, which has a molecular general formula as follows:
wherein R is1、R2、R3Each of which is one of a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heterocyclic group having 5 to 50 carbon atoms, or an aromatic amino group having 6 to 30 carbon atoms;
Ar1、Ar2the aromatic amine is one of a hydrogen atom, an alkylaryl group having 7 to 50 carbon atoms, an alkylaryloxy group having 7 to 50 carbon atoms, an alkylarylthio group having 7 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heterocyclic group having 5 to 50 carbon atoms, an aromatic amine group having 6 to 30 carbon atoms, an aryloxy group having 6 to 50 carbon atoms, or an aryloxyarylthio group having 6 to 50 carbon atoms.
Preferably, R1, R2 and R3 in the formula are independently selected from any one of the following chemical formulas under the condition that the above definition is satisfied:
wherein X and Y are independently one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkylaryloxy group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, and a substituted or unsubstituted aromatic amine having 6 to 30 carbon atoms.
Further, the aromatic amine compound molecule may be selected from any one of the following:
the invention also provides a preparation method of the aromatic amine compound, which comprises the following steps:
step 1, carrying out coupling reaction and methoxy dissociation according to the following reaction formula to obtain a 2-PQDO compound
Step 2, synthesizing a compound by the following formula including a replacement reaction and a coupling reaction of a ketone group
The method specifically comprises the following steps:
step 11, preparation of intermediate 1
Dissolving 0.1-0.2 mol of reactant 2 in 300mL of anhydrous ether, carrying out dry ice bath at-78 ℃, adding 44mL of 2.5M butyl lithium under the condition of isolating oxygen, stirring and reacting for 1 hour, then adding 0.1-0.2 mol of reactant 1, reacting for 2 hours, gradually increasing the temperature to 15-25 ℃, adding water to stop the reaction,
then, carrying out liquid separation on the reaction product, removing a water layer, extracting the water layer once by using ethyl acetate, carrying out spin-drying on the organic solvent, and carrying out column separation by using dichloromethane and polyethylene which have a volume ratio of 9:1 to obtain an intermediate 1;
step 12, preparation of intermediate 2
Dissolving 41mmol-42mmol of intermediate 1 in 250mL-300mL of tetrahydrofuran, cooling to 0 ℃, adding the mixed solution LTMP, and stirring at 0 ℃ for reaction for 2 hours;
synthesis of LTMP: 500mL of tetrahydrofuran was dissolved at 0 ℃ with 0.13mol of butyllithium and 0.14mol of 2,2,6, 6-tetramethylpiperidine;
then adding 200mL of water to terminate the reaction, separating a water layer, spin-drying an organic layer, and separating by using dichloromethane and petroleum ether in a volume ratio of 10:1 through a column to obtain an intermediate 2;
step 21, preparation of intermediate 3 by replacement of the keto group
Accurately weighing 10g-15g of the intermediate 2, adding the intermediate 2 into a reaction bottle, adding 200mL-300mL of acetonitrile, weighing 30g-50g of phosphorus oxychloride, slowly dropwise adding the phosphorus oxychloride into the reaction bottle, slowly heating to 60-70 ℃ after dropwise adding, reacting for 4-6 hours, adding water to carefully extract and kill the phosphorus oxychloride after reaction, adding a large amount of sodium carbonate saturated solution to adjust the pH value to 7-8, adding dichloromethane, extracting for three times, and spin-drying to obtain 7g-8g of the intermediate 3;
step 22, preparing aromatic amine compound through coupling reaction
Adding 14g-16g of intermediate 3, 17g-19g of reactant 3 and 3g-5g of palladium tetratriphenylphosphine into a reaction bottle, adding 500mL-600mL of mixed solution of toluene, ethanol and water in a volume ratio of 2:1:1, stirring and heating to 110 ℃, reacting for 22-24 hours under the protection of nitrogen, then cooling the system, separating liquid, spin-drying the toluene, adding dichloromethane to dissolve solids, passing through a column, and reacting by using a solvent in a volume ratio of 2:1, washing with petroleum ether and ethyl acetate to prepare an aromatic amine compound;
wherein the reactant 1 is，
Reactant 2 is，
Reactant 3 is，
Intermediate 1 is，
Intermediate 2 is，
Intermediate 3 is
The invention also provides application of the novel aromatic amine compound, and the aromatic heterocyclic compound is used for manufacturing an organic electroluminescent device.
The device comprises a first electrode, a second electrode and one or more organic compound layers disposed between the two electrodes, at least one organic compound layer containing at least one of the aromatic amine-based compounds.
The organic layer comprises a hole injection layer, a hole transport layer, a layer with both hole injection and hole transport skills, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection layer and a layer with both electron transport and electron injection skills.
The organic electroluminescent device further comprises an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
The invention has the beneficial effects that:
the novel heterocyclic diffractants of the present invention are pyrido [3,2-g ]]Introduction of Ar into quinoline1、Ar2And R1～R3Increasing electron density and upward ability, and additionally pyrido [3,2-g]The side chains R1 and R2 of quinoline have the advantage of improved performance and improved dexterity.
The device manufactured by using the novel heterocyclic diffractometer has the characteristics of high brightness, excellent heat resistance, long service life, high efficiency and the like.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in 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.
The molecular general formula of the novel aromatic amine compound provided by the invention is as follows:
wherein R is1、R2、R3Can be one of a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heterocyclic group having 5 to 50 carbon atoms, or an aromatic amino group having 6 to 30 carbon atoms;
Ar1、Ar2any one of a hydrogen atom, an alkylaryl group having 7 to 50 carbon atoms, an alkylaryloxy group having 7 to 50 carbon atoms, an alkylarylthio group having 7 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heterocyclic group having 5 to 50 carbon atoms, an aromatic amino group having 6 to 30 carbon atoms, an aryloxy group having 6 to 50 carbon atoms, and an aryloxyarylthio group having 6 to 50 carbon atoms may be used.
The novel aromatic amine compound molecule can be selected from any one of the following:
the method for preparing the aromatic amine compound comprises the following steps:
step 1, carrying out coupling reaction and methoxy dissociation according to the following reaction formula to obtain a 2-PQDO compound
Step 2, synthesizing a compound by the following formula including a replacement reaction and a coupling reaction of a ketone group
The method comprises the following specific steps:
step 11, preparation of intermediate 1
Dissolving 0.1-0.2 mol of reactant 2 in 300mL of anhydrous ether, carrying out dry ice bath at-78 ℃, adding 44mL of 2.5M butyl lithium under the condition of isolating oxygen, stirring for reaction for 1 hour, adding 0.1-0.2 mol of reactant 1, reacting for 2 hours, gradually increasing the temperature to 15-25 ℃, adding water to terminate the reaction, separating the reaction product, removing a water layer, extracting the water layer once with ethyl acetate, spin-drying an organic solvent, and separating with a column by using dichloromethane and polyethylene with a volume ratio of 9:1 to obtain an intermediate 1;
step 12, preparation of intermediate 2
Dissolving 41mmol-42mmol of intermediate 1 in 250mL-300mL of tetrahydrofuran, cooling to 0 ℃, adding the mixed solution LTMP, and stirring at 0 ℃ for reaction for 2 hours;
synthesis of LTMP: 500mL of tetrahydrofuran was dissolved at 0 ℃ with 0.13mol of butyllithium and 0.14mol of 2,2,6, 6-tetramethylpiperidine;
then adding 200mL of water to terminate the reaction, separating a water layer, spin-drying an organic layer, and separating by using dichloromethane and petroleum ether in a volume ratio of 10:1 through a column to obtain an intermediate 2;
step 21, preparation of intermediate 3 by replacement of the keto group
Accurately weighing 10g-15g of the intermediate 2, adding the intermediate 2 into a reaction bottle, adding 200mL-300mL of acetonitrile, weighing 30g-50g of phosphorus oxychloride, slowly dropwise adding the phosphorus oxychloride into the reaction bottle, slowly heating to 60-70 ℃ after dropwise adding, reacting for 4-6 hours, adding water to carefully extract and kill the phosphorus oxychloride after reaction, adding a large amount of sodium carbonate saturated solution to adjust the pH value to 7-8, adding dichloromethane, extracting for three times, and spin-drying to obtain 7g-8g of the intermediate 3;
step 22, preparing aromatic amine compound through coupling reaction
Adding 14g-16g of intermediate 3, 17g-19g of reactant 3 and 3g-5g of palladium tetratriphenylphosphine into a reaction bottle, adding 500mL-600mL of mixed solution of toluene, ethanol and water in a volume ratio of 2:1:1, stirring and heating to 110 ℃, reacting for 22-24 hours under the protection of nitrogen, then cooling the system, separating liquid, spin-drying the toluene, adding dichloromethane to dissolve solids, passing through a column, and reacting by using a solvent in a volume ratio of 2:1, washing with petroleum ether and ethyl acetate to prepare an aromatic amine compound;
wherein,
reactant 1 is
Reactant 2 is
Reactant 3 is
Intermediate 1 is
Intermediate 2 is
Intermediate 3 is
The aromatic heterocyclic compound is used for manufacturing an organic electroluminescent device.
The invention provides an application of the aromatic amine compound in the technical scheme or the aromatic amine compound obtained by the preparation method in the technical scheme in an organic electroluminescent device, and the aromatic amine compound is used as a hole transport material or a hole blocking material.
The organic electroluminescent device has no special requirements on the structure of the organic electroluminescent device, and the conventional organic electroluminescent device can be adopted. In the present invention, the organic electroluminescent device preferably includes a first electrode, a second electrode, and one or more organic layers interposed between the two electrodes; more preferably, at least one of the organic layers includes the aromatic amine-based compound according to the above technical means or the aromatic amine-based compound obtained by the preparation method according to the above technical means, and at least one of the organic layers includes the aromatic amine-based compound according to the above technical means or the aromatic amine-based compound obtained by the preparation method according to the above technical means and other substances.
The organic layer of the organic electroluminescent device has no special requirement, and the organic layer of the organic electroluminescent device can be arranged according to the organic layer of the conventional organic electroluminescent device. In the present invention, the organic layer preferably includes at least one of a hole injection layer, a hole transport layer, an injection transport layer having both hole injection and hole transport technologies, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an injection transport layer having both electron transport and electron injection technologies; more preferably, at least one of the three layers of the hole injection layer, the hole transport layer, and the injection transport layer having both hole injection and hole transport functions is a material containing a conventional hole injection material, a hole transport material, a material having both hole injection and hole transport functions, or an electron transport material.
Further preferably, the light-emitting layer may be a red, yellow or cyan light-emitting layer. The novel heterocyclic derivative is used for a cyan host or a cyan dopant in the light-emitting layer cyan, and provides an organic light-emitting device having high efficiency, high luminance, high resolution and long lifetime.
Example (b): synthesis of intermediates
Synthesis of intermediate 2-chloro-6-phenylpyridine (1-1)
The synthesis method comprises the following steps: 2-bromo-6-chloropyridine (21.2g, 0.11mol), phenylboronic acid (12.2g, 0.10mol), and tetrakistriphenylphosphine palladium (0.5 g) were charged into a 1000ML reaction flask, followed by addition of toluene 400ML, aqueous sodium carbonate (2N,150mL) under nitrogen, and oil bath at 80 ℃ for 24 hours. And (3) post-treatment process: cooling, standing for 30 minutes, separating liquid, reserving an organic layer, spin-drying toluene, dissolving solid by adding dichloromethane, and performing column chromatography separation, wherein the PE: DCM ═ 1:1 punch column to obtain A-1(9.6g, y is 51%)
Synthesis of intermediates 1-2 and 1-3
The synthesis of intermediate 1-1 described above gave the following compounds:
synthesis of intermediate 6-chloro-N, N-diphenylpyridin-2-amine (1-4):
the synthesis method comprises the following steps: diphenylamine (16.9g, 0.10mol) and sodium tert-butoxide (28g, 0.30mol) and 400mL of toluene are added into a reaction bottle, stirred for 30 minutes under nitrogen protection, then 6-bromo-2-chloropyridine (23.09g, 0.12mol) and 1.5g of tris (dibenzylideneacetone) dipalladium are added, finally 4g of tri-tert-butylphosphine is added, and the temperature is raised to 100 ℃ for reaction for 24 hours. And (3) post-treatment process: the system was cooled, water was added to terminate the reaction, the reaction was filtered, the filtrate was separated, toluene was spin-dried, a small amount of dichloromethane was added to dissolve the solid, and petroleum ether and dichloromethane (volume ratio) 3:1 were separated by column chromatography to give solid (1-4) (14.03g, y ═ 50%).
Synthesis of intermediates 1-5 and 1-6
The above synthesis of intermediates 1-4 gave the compounds of the following table:
synthesis of intermediate 6-phenyl-2-pyridineboronic acid (2-1)
2-chloro-6-phenylpyridine (8.04g, 42.4mmol) was charged into a three-necked flask, and 100mL of THF was added under nitrogen protection, and the mixture was stirred at-78 ℃ for 30 minutes, then 21mL of n-butyllithium (2.5M) was added, and the mixture was reacted for 1 hour, 14g of triisopropyl borate was further added, and the reaction was carried out at low temperature for 1 hour, followed by gradually returning to room temperature. In the post-treatment process, 2M hydrochloric acid was added to the system to adjust the PH of the solution to 4 to 5, the solution was allowed to stand for liquid separation, the aqueous layer was extracted once with ethyl acetate, and the organic layers were combined and spin-dried to obtain white solid (2-1) (6.8g, y ═ 80%).
Synthesis of intermediates 2-2 and 2-6
The above synthesis of intermediate 2-1 gives the following compounds:
synthesis of intermediate methyl 2- (pyridine-2-carbonyl) picolinate (3-1)
The synthesis method comprises the following steps: dissolving 2-pyridine boric acid (0.1mol) in 300mL of anhydrous ether, carrying out dry ice bath at-78 ℃, adding 44mL of butyl lithium (2.5M) under the condition of isolating oxygen, stirring for reaction for 1 hour, adding 2-bromine-methyl picolinate (0.1mol), reacting for 2 hours, gradually increasing the temperature to 15-25 ℃, and adding water to stop the reaction.
And (3) post-treatment process: the reaction product was separated, the aqueous layer was extracted once with ethyl acetate, the organic solvent was dried by spinning, and the mixture was separated by column chromatography using dichloromethane to polyethylene (vol%) 9:1 to obtain 3-1 as a white solid (yield 51%).
Synthesis of intermediates 3-2 to 3-7
The above synthesis of intermediate 3-1 gives the following compounds:
synthesis of intermediate pyridine [3,2-g ] quinoline-5, 10-dione (4-1):
the synthesis method comprises the following steps: dissolving 3-1(41.5mmol) in 300mL tetrahydrofuran, cooling to 0 ℃, adding the mixed solution LTMP, and stirring at 0 ℃ for reaction for 2 hours.
Synthesis of LTMP: 500mL of tetrahydrofuran were used to dissolve 0.13mol of butyllithium and 0.14mol of 2,2,6, 6-tetramethylpiperidine at 0 ℃.
And (3) post-treatment process: the reaction was terminated by adding 200mL of water, the aqueous layer was separated, the organic layer was spin-dried, and the residue was separated by column chromatography using dichloromethane and petroleum ether (10: 1) to give solid (4-1) (3.8g, 4% yield).
Synthesis of intermediates 4-2 to 4-7
Synthesis of intermediate 5, 10-dichloropyrido [3,2-g ] quinoline (5-1):
accurately weighing 4-1(10g, 47.8mmol) and adding into a reaction bottle, adding 200mL of acetonitrile, weighing 30g of phosphorus oxychloride and slowly dripping into the reaction bottle, after dripping, slowly heating to 60 ℃ and reacting for 5 hours. After the reaction is finished, water is added for careful extraction and extinction, an amplified amount of sodium carbonate saturated solution is added for adjusting the pH value to 7-8, dichloromethane is added for extraction for three times, and solid (5-1) (7.5g, y is 63%) is obtained by spin drying. Synthesis of intermediates 5-2 to 5-7
The above synthesis of intermediate 5-1 gives the following compounds:
example (b): synthesis of aromatic amine compound
Example 5 Synthesis of 10-diphenylpyrido [3,2-g ] quinoline (6-1)
The prepared 5, 10-dichloro-pyrido [ g ] quinoline 5-1(14.8g, 0.6mmol), 4-pyridine borate (18g, 0.146mmol) and 4g palladium tetratriphenylphosphine are added into a reaction bottle, 600mL of mixed solution of toluene, ethanol and water in a volume ratio of 2:1:1 is added, nitrogen is used for protection, and the mixture is stirred and heated to 110 ℃ for reaction for 24 hours. And (3) post-treatment process: and cooling the system, separating liquid and spin-drying toluene. Dichloromethane was added to dissolve the solid, column passed, petroleum ether: ethyl acetate ═ 2:1 (vol.%) to give (6-1) (13g, 65% y).
Examples 6-2 to 6-17 Synthesis
The following compounds were obtained according to the synthesis method of the above example 6-1:
example Synthesis of N5, N5, N10, N10-tetraphenylpyrido [3,2-g ] quinoline-5, 10-diamine (6-23):
according to the synthesis method of the intermediate 1-4, 5, 10-dichloropyrido [3,2-g ] quinoline (6.0g, 24mmol) and diphenylamine (4.4, 24mmol) are used as raw materials to react, so that N5, N5, N10 and N10-tetraphenylpyrido [3,2-g ] quinoline-5, 10-diamine (6.17g, y is 50%) are obtained.
Example 5 Synthesis of 10-bis (1-naphthyloxy) pyrido [3,2-g ] quinoline (6-24):
1-hydroxynaphthalene (14g,0.1mol) was dissolved in 100mL of anhydrous tetrahydrofuran, stirred, and exactly weighed NaH (0.96g,0.4mol) was added in portions to the reaction flask, not too quickly, to prevent too many bubbles, after the addition, the solution appeared yellow, and 5, 10-dichloropyrido [3,2-g ] quinoline (27.50g, 0.11mol) was added, also in portions, and reacted at room temperature overnight. And (3) post-treatment process: filtering, removing solid substances, spin-drying the filtrate, adding dichloromethane for dissolution, and purifying with petroleum ether: ethyl acetate ═ 1: 5 (volume ratio) to obtain solid (23.20g, y 50%).
Example 5 synthesis of 10-bis (1-naphthylthio) pyrido [3,2-g ] quinoline (6-25):
1-Naphthalenethiol (1.6g, 10mmol), 5, 10-dichloropyrido [3,2-g ] quinoline (2.48g, 10mmol), potassium hydroxide (840mg, 15mmol), mPANI/pFe3O4(2.5g, 5 mol%) H2O (30mL) were mixed and heated for 8 hours. The organic phase was extracted by ethyl acetate and the reaction mixture was extracted with ethyl acetate: separation on a column with petroleum ether at 4:1 (vol%) gave a white solid (6-25) (1.89g, y 38%).
Example 5 Synthesis of- (1-naphthyl) -10- (2-naphthyl) pyrido [3,2-g ] quinoline (6-26):
the synthesis method comprises the following steps: with reference to the synthesis of E-1, 5, 10-dichloropyrido [3,2-g ] quinoline (4.41g,17.8mmol) and 2-naphthalene boronic acid (3.4g, 19.6mmol) were charged to give 5-bromo-10- (2-naphthyl) pyrido [3,2-g ] quinoline as a solid (2.91g, 48% yield).
The synthesis method comprises the following steps: with reference to the synthesis of E-1, 5-bromo-10- (2-naphthyl) pyrido [3,2-g ] quinoline (2.91g, 8.5mmol) and 1-naphthaleneboronic acid (1.65g, 9.6mmol) were charged to give E-23 as a solid (1.76g, 48% yield).
Example (b): preparation of organic light-emitting device
Coating thickness of Fisher company ofThe ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, washed in sequence with isopropyl alcohol, acetone, and methanol for 30 minutes, repeatedly washed with distilled water for 2 times, ultrasonically for 10 minutes, dried, transferred to a plasma cleaner, washed for 5 minutes, and sent to an evaporation coater. Evaporating a hole injection layer 2-TNATA on the prepared ITO transparent electrodeEvaporation of hole transport layer a-NPDBlue host AND/5% doped TPPDA evaporation
Hole blocking layer and hole transport layer TPBi or deposition of substance of example ECathode electrode The organic evaporation speed is maintained in the above processLiF isAl is
The electron emission characteristics of the organic light emitting device manufactured by the above method are shown in the following table.
From the results in the table, it can be seen that the light emission efficiency and the lifetime characteristics are remarkably improved in the co-layer region of the novel aromatic amine derivative of the present invention.
The present invention is useful in the OLED industry because the organic light-emitting device using the novel aromatic amine derivative can achieve good light-emitting efficiency and long lifetime. The organic light-emitting device of the present invention is suitably used as a light source, a display panel, a marker, or the like for flat panel display, a flat light-emitting body, a surface-emitting OLED light-emitting body for illumination, a flexible light-emitting body, a copying machine, a printer, an LCD backlight, or a measuring machine.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (7)

1. An aromatic amine compound is characterized in that the molecular general formula of the compound is as follows:
wherein, R is1Is a benzene ring, R2Is a hydrogen atom, R3Is a hydrogen atom, or R1Is a hydrogen atom, R2Is a benzene ring, R3Is a hydrogen atom; ar (Ar)1、Ar2Are all benzene rings,
respectively obtain the compound
2. The method for preparing the aromatic amine compound according to claim 1, comprising the steps of:
step 1, carrying out coupling reaction and methoxy dissociation according to the following reaction formula to obtain a 2-PQDO compound
Step 2, synthesizing aromatic amine compound by the following formula including replacement reaction and coupling reaction of keto group
3. The method according to claim 2, characterized in that it comprises in particular the steps of:
step 11, preparation of intermediate 1
Dissolving 0.1-0.2 mol of reactant 2 in 300mL of anhydrous ether, carrying out dry ice bath at-78 ℃, adding 44mL of 2.5M butyl lithium under the condition of isolating oxygen, stirring for reaction for 1 hour, adding 0.1-0.2 mol of reactant 1, reacting for 2 hours, gradually increasing the temperature to 15-25 ℃, adding water to terminate the reaction, separating the reaction product, removing a water layer, extracting the water layer once with ethyl acetate, spin-drying an organic solvent, and separating with a column by using dichloromethane and polyethylene with a volume ratio of 9:1 to obtain an intermediate 1;
step 12, preparation of intermediate 2
Dissolving 41mmol-42mmol of intermediate 1 in 250mL-300mL of tetrahydrofuran, cooling to 0 ℃, adding the mixed solution LTMP, and stirring at 0 ℃ for reaction for 2 hours;
synthesis of LTMP: 500mL of tetrahydrofuran was dissolved at 0 ℃ with 0.13mol of butyllithium and 0.14mol of 2,2,6, 6-tetramethylpiperidine;
then adding 200mL of water to terminate the reaction, separating a water layer, spin-drying an organic layer, and separating by using dichloromethane and petroleum ether in a volume ratio of 10:1 through a column to obtain an intermediate 2;
step 21, preparation of intermediate 3 by replacement of the keto group
Accurately weighing 10g-15g of the intermediate 2, adding the intermediate 2 into a reaction bottle, adding 200mL-300mL of acetonitrile, weighing 30g-50g of phosphorus oxychloride, slowly dropwise adding the phosphorus oxychloride into the reaction bottle, slowly heating to 60-70 ℃ after dropwise adding, reacting for 4-6 hours, adding water to carefully extract and kill the phosphorus oxychloride after reaction, adding a large amount of sodium carbonate saturated solution to adjust the pH value to 7-8, adding dichloromethane, extracting for three times, and spin-drying to obtain 7g-8g of the intermediate 3;
step 22, preparing aromatic amine compound through coupling reaction
Adding 14g-16g of intermediate 3, 17g-19g of reactant 3 and 3g-5g of palladium tetratriphenylphosphine into a reaction bottle, adding 500mL-600mL of mixed solution of toluene, ethanol and water in a volume ratio of 2:1:1, stirring and heating to 110 ℃, reacting for 22-24 hours under the protection of nitrogen, then cooling the system, separating liquid, spin-drying the toluene, adding dichloromethane to dissolve solids, passing through a column, and reacting by using a solvent in a volume ratio of 2:1, washing with petroleum ether and ethyl acetate to prepare an aromatic amine compound;
wherein the reactant 1 is，
Reactant 2 is，
Reactant 3 is，
Intermediate 1 is，
Intermediate 2 is，
Intermediate 3 is
4. The application of the novel aromatic amine compound as claimed in claim 1, wherein the aromatic heterocyclic compound is used for manufacturing an organic electroluminescent device.
5. An organic electroluminescent device produced using the aromatic amine-based compound according to claim 1, comprising a first electrode, a second electrode, and one or more organic compound layers interposed between the two electrodes, at least one organic compound layer comprising at least one of the aromatic amine-based compounds.
6. The organic electroluminescent device according to claim 5, wherein the organic layers comprise a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport properties, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection layer, and a layer having both electron transport and electron injection properties.
7. The organic electroluminescent device according to claim 5, further comprising an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
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