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CN109180582A - Luminous organic material and its preparation method and organic luminescent device containing the material - Google Patents

Luminous organic material and its preparation method and organic luminescent device containing the material Download PDF

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Publication number
CN109180582A
CN109180582A CN201811180999.7A CN201811180999A CN109180582A CN 109180582 A CN109180582 A CN 109180582A CN 201811180999 A CN201811180999 A CN 201811180999A CN 109180582 A CN109180582 A CN 109180582A
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organic
unsubstituted
layer
substituted
compound
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李文军
林文晶
王辉
王永光
王士凯
张成成
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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Abstract

The present invention relates to field of light emitting materials, and in particular to a kind of luminous organic material and its preparation method and the organic luminescent device containing the material.Luminous organic material provided by the invention is any one in following structural formula:In structure above: R is phenyl or xenyl；Ar1And Ar2It is each independently selected from the aryl of substituted or unsubstituted C6-31 or the heteroaryl of substituted or unsubstituted C12-30.The present invention obtains Hole injection capacity/transmittability, high power efficiency, long-life by introducing arylamine on acridine ring.There is splendid current efficiency and power efficiency and long-life by organic electroluminescence device prepared by machine luminophor of the invention.The preparation method of organic luminescent compounds of the invention, reproducible, yield is high.

Description

Luminous organic material and its preparation method and organic luminescent device containing the material
Technical field
The present invention relates to field of light emitting materials, and in particular to a kind of luminous organic material and its preparation method and having containing the material Machine luminescent device.
Background technique
Organic electroluminescence device is since its is small in size, light-weight, driving voltage is low, response is fast, visual angle is wide and can be real Show the advantages that large area full color flat panel is shown and have become a hot topic of research, and has fabulous business and market prospects.For many years Research not only organic electroluminescent theoretically, but also in the practical performance of device, such as brightness, driving voltage, service life are all Various aspects have significant progress.The maximum brightness of organic electroluminescence device is more than 140000cd/m at present2, driving voltage It is lower than 10V, the continuous use service life is up to 50000h more.
In order to further increase brightness, efficiency and the service life of organic electroluminescence device, multilayer is usually used in the devices Structure.These multilayered structures include luminescent layer and various auxiliary organic layers, such as: hole injection layer, hole transmission layer, electron-transport Layer etc..The effect of these auxiliary organic layers is the injection efficiency for improving carrier (hole and electronics) between each bed boundary, balance The transmission of carrier between the layers, to improve the brightness and efficiency of device.Wherein, the effect of hole transmission layer is to improve sky The transmission rate of cave in the devices, and effectively by electronic blocking in luminescent layer, realize that the maximum of carrier is compound；It drops simultaneously Energy barrier of the low hole in injection process, improves the injection efficiency in hole, to improve the brightness of device, service life and effect Rate.
Traditional hole mobile material is substantially based on triaryl derivative.Although it is with cavity transmission ability and low drive Dynamic voltage, but have to introduce a large amount of substituent group promotion in its structure in order to obtain suitable glass transition temperature Its molecular weight.But triplet energies or LUMO energy are really reduced in this way, so as to cause the deterioration of organic electroluminescence device.Reason The hole mobile material thought needs high glass transition temperature, Hole injection capacity and cavity transmission ability, and is suitble to triple State energy and LUMO energy.
Summary of the invention
The invention solves in the prior art the technical issues of, provide a kind of luminous organic material and its preparation method and containing the material The organic luminescent device of material.
In order to solve the above-mentioned technical problem, technical solution of the present invention is specific as follows:
A kind of luminous organic material, be following structural formula in any one:
In structure above:
R is phenyl or xenyl；
Ar1And Ar2It is each independently selected from the aryl or substituted or unsubstituted C12- of substituted or unsubstituted C6-31 30 heteroaryl.
In the above-mentioned technical solutions, Ar1And Ar2Be each independently selected from substituted or unsubstituted C10-25 aryl or The heteroaryl of substituted or unsubstituted C16-24.
In the above-mentioned technical solutions, Ar1And Ar2Be each independently selected from substituted or unsubstituted C14-21 aryl or The heteroaryl of substituted or unsubstituted C18-22.
In the above-mentioned technical solutions, Ar1And Ar2Be each independently selected from substituted or unsubstituted C16-19 aryl or The heteroaryl of substituted or unsubstituted C21.
In the above-mentioned technical solutions, the luminous organic material is any one in following structures:
A kind of preparation method of luminous organic material, comprising the following steps:
The synthesis of step 1, intermediate
By the de gassed solution N of compound 2 and compound 1 in toluene2Saturation；Then (bis- (the hexichol of 1,1'- are added Base phosphine) ferrocene and acid chloride (II), then add NaOtBu；By the reaction mixture heated overnight at reflux；After reaction, After being cooled to room temperature, water is added, water phase is washed with toluene, uses MgSO4It is dry, and solvent is removed under vacuum；It uses Heptane/ethyl acetate filters crude product via silica gel, obtains intermediate 1；
N- bromo-succinimide is added in the dichloromethane solution of intermediate 1 at 0 DEG C under the conditions of being protected from light, and And the mixture is continued to stir at such a temperature；The reaction is terminated by adding sodium sulfite solution, and again in room temperature Under continue to stir；After phase separation, organic phase is washed with water, and water phase is extracted with methylene chloride；By the organic of merging It is mutually dry with sodium sulphate, and evaporate under vacuum；Residue is dissolved in ethyl acetate, and is filtered via silica gel；Then will Crude product is recrystallized from heptane；Obtain intermediate 2；
Synthetic route is as follows:
The synthesis of step 2, target product
Under nitrogen protection system, intermediate 2 is added into reaction flask, adds compound 3 or compound 4, then plus Enter sodium tert-butoxide and solvent, deaerate to reaction system, catalyst tris(dibenzylideneacetone) dipalladium, three (tert-butyl) phosphines is added, The temperature of reaction system is risen to reflux to react, ultrapure water stirring is added after reaction, filters, ethyl alcohol and ultrapure water leaching It washes, target product is obtained after drying；
Compound 3 and 4 structural formula of compound are as follows:
Wherein: R is phenyl or xenyl；Ar1And Ar2Be each independently selected from substituted or unsubstituted C6-31 aryl, Or the heteroaryl of substituted or unsubstituted C12-30；
L is any one in following structures:
The present invention also provides a kind of organic luminescent devices containing above-mentioned luminous organic material.
In the above-mentioned technical solutions, the organic luminescent device includes:
First electrode, second electrode and the organic matter layer being placed between two electrode, wherein wrapped in the organic matter layer Contain above-mentioned luminous organic material；Above-mentioned luminous organic material can be single form or be mixed with other materials in organic In nitride layer.
The organic matter layer includes at least hole injection layer, and hole transmission layer had both had hole injection and passed but also with hole Defeated technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and not only have electron-transport but also Has one or more of electron injection technical ability layer.
" organic matter layer " refers to the whole disposed between organic luminescent device first electrode and second electrode in the present invention The term of layer.
When above-mentioned luminous organic material is present in hole transmission layer or hole injection layer in the organic matter layer, institute Stating luminous organic material can be used as hole transmission layer, hole injection layer and both has hole injection but also with hole transport function Ergosphere.
Of the present invention includes that the device of above-mentioned luminous organic material preparation can be used for organic luminescent device (OLED), organic photovoltaic cell (OSC), Electronic Paper (e-Paper), Organophotoreceptor (OPC) or Organic Thin Film Transistors (OTFT)。
Organic luminescent device of the present invention can pass through the side such as film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) Method evaporation metal and conductive oxide and their alloy on substrate form anode, can also be applied using rotation Film (spin-coating) or strip take the lead to be deposited；It can also be using molding (tape-casting), scraping blade method (doctor- Blading), the methods of silk-screen printing (Screen-Printing), ink jet printing or thermal imaging (Thermal-Imaging) subtract Few number of plies manufacture.
The beneficial effects of the present invention are:
The present invention is provided to the hole mobile materials for solving the problems, such as traditional technology in organic el device.Traditional sky Hole transport materials are substantially based on triaryl derivative.Although it is with cavity transmission ability and low driving voltage, in order to It obtains suitable glass transition temperature and has to introduce a large amount of substituent group in its structure and promote its molecular weight.But this Sample but reduces triplet energies or LUMO energy, so as to cause the deterioration of organic luminescent device.Ideal hole mobile material needs Want high glass transition temperature, Hole injection capacity and cavity transmission ability and suitable triplet energies and LUMO energy.Cause This obtains ideal material to solve the problems, such as conventional hole transmission material, and the present invention proposes on acridine ring Introduce the solution of arylamine.Hole injection capacity/transmittability, high power efficiency, length are obtained by introducing arylamine Service life.
By organic luminescent device prepared by luminous organic material of the invention have splendid current efficiency and power efficiency with And the long-life.
The preparation method of luminous organic material of the invention, reproducible, yield is high.
Specific embodiment
The synthesis of intermediate 2
By the de gassed solution N of 2 bromobenzene of 243.7mmol compound and 203.1mmol compound 1 in 1000mL toluene2 Saturation 1 hour.Then, first by 5.6g (10.1mmol) DPPF (1,1'- bis- (diphenylphosphine) ferrocene), then by 2.28g (10.1mmol) acid chloride (II) is added to the solution, then adds the NaOtBu of 52.3g (528mmol) solid state.It should Reaction mixture heated overnight at reflux.After cooling to room-temperature, 500mL water is carefully added.By water phase 3 × 50mL toluene Washing, uses MgSO4It is dry, and solvent is removed under vacuum.Thick produce is filtered via silica gel using heptane/ethyl acetate (20:1) Object obtains intermediate 1-1, yield: 60g, and the 75% of theoretical value, pale yellow crystals.
N- bromo-succinimide (9.8g, 55.3mmol) portioning is added to intermediate at 0 DEG C under the conditions of being protected from light 1-1 (16.9g, 55.3mmol) stirs 2 in the solution in methylene chloride (140mL), and by the mixture at such a temperature Hour.The reaction is terminated by adding sodium sulfite solution, and is stirred at room temperature 30 minutes.After phase separation, will Organic phase is washed with water, and water phase is extracted with methylene chloride.Combined organic phase is dry with sodium sulphate, and steam under vacuum Hair.Residue is dissolved in ethyl acetate, and is filtered via silica gel.Then crude product is recrystallized from heptane.It is prepared into To intermediate 2-1, yield: 14g, the 97% of theoretical value, colorless solid.
Above-mentioned bromobenzene is replaced with into 4- bromo biphenyl, intermediate 2-2 is prepared, structural formula is as follows:
Embodiment 1
The synthesis of compound 001
Under nitrogen protection system, 10.0mmol intermediate 2-1 and 12.0mmol diphenylamines is added, sodium tert-butoxide is added 30mmol and solvent 30mL, solvent are dry toluene.It deaerates to reaction system, catalyst tris(dibenzylideneacetone) dipalladium is added The temperature of reaction system is risen to reflux by 0.1mmol, three (tert-butyl) phosphine 1mmol, is reacted 12 hours.It is added after reaction super Pure water stirring, filters, and ethyl alcohol and ultrapure water elution obtain compound 001, yield 85%, mass spectrometry value: 514.30 after drying.
Embodiment 2-18
The synthesis of reference compound 001, according to the Material synthesis following substances of following table.
Table 1
Embodiment 19
The synthesis of compound 133
Under nitrogen protection system, 10.0mmol intermediate 2-1 and 12.0mmol compound 19-1 is added, sodium carbonate is added 25mmol and solvent 30mL, solvent are toluene and water, and ratio 2:1 deaerates to reaction system, and four triphenylphosphine of catalyst is added The temperature of reaction system is risen to reflux, reacts 24 hours, use petroleum ether by palladium 0.2mmol: methylene chloride=2:1 recrystallization, Obtain compound 133, yield 75%, mass spectrometric data are as follows: 742.30.
Embodiment 20
The synthesis of compound 180
Under nitrogen protection system, 10.0mmol intermediate 2-1 and 12.0mmol compound 20-1 is added, sodium carbonate is added 25mmol and solvent 30mL, solvent are toluene and water, and ratio 2:1 deaerates to reaction system, and four triphenylphosphine of catalyst is added The temperature of reaction system is risen to reflux, reacts 24 hours, use petroleum ether by palladium 0.2mmol: methylene chloride=2:1 recrystallization, Obtain compound 180, yield 75%, mass spectrometric data are as follows: 832.31.
Embodiment 21
The synthesis of compound 181
Under nitrogen protection system, 10.0mmol intermediate 2-1 and 12.0mmol compound 21-1 is added, sodium carbonate is added 25mmol and solvent 30mL, solvent are toluene and water, and ratio 2:1 deaerates to reaction system, and four triphenylphosphine of catalyst is added The temperature of reaction system is risen to reflux, reacts 24 hours, use petroleum ether by palladium 0.2mmol: methylene chloride=2:1 recrystallization, Obtain compound 181, yield 75%, mass spectrometric data are as follows: 858.43.
Embodiment 22
The synthesis of compound 187
Under nitrogen protection system, 10.0mmol intermediate 2-2 and 12.0mmol compound 22-1 is added, sodium carbonate is added 25mmol and solvent 30mL, solvent are toluene and water, and ratio 2:1 deaerates to reaction system, and four triphenylphosphine of catalyst is added The temperature of reaction system is risen to reflux, reacts 24 hours, use petroleum ether by palladium 0.2mmol: methylene chloride=2:1 recrystallization, Obtain compound 187, yield 75%, mass spectrometric data are as follows: 782.40.
The preparation of organic luminescent device
It is by coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic washing 30 minutes, It is cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleans, isopropanol, acetone, methanol equal solvent It is dry after ultrasonic washing in order, it is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, vapor deposition is sent to In machine.The 4,4' for being 50nm by evaporation thickness on the ito transparent electrode having had been prepared for, 4 "-three [2- naphthylphenyl amino] three Phenyl amine (2-TNATA) is used as hole injection layer.Then the compound prepared by above-described embodiment 1-22 any one or a-NPD On the hole injection layer of formation vacuum evaporation with a thickness of 30nm hole transmission layer.Then it is steamed on above-mentioned hole transmission layer Plate blue material of main part 9,10- bis- (2- naphthalene) anthracene (ADN) and dopant material N1, N1, N6, N6- tetraphenyl with a thickness of 30nm Pyrene -1,6- diamines (TPPDA).The weight ratio of material of main part and dopant material is 95:5.Then vacuum is steamed on above-mentioned luminescent layer The TPBi with a thickness of 40nm is plated as hole blocking layer and electron transfer layer.On above-mentioned electron transfer layer vacuum evaporation with a thickness of 0.5nm lithium fluoride (LiF), as electron injecting layer.The aluminium that last evaporation thickness is 150nm has been completed as cathode with this The preparation of machine luminescent device.Performance characteristics of luminescence test to obtained device, measurement use 2400 type of KEITHLEY Keithley Source measuring unit, CS-2000 spectroradio luminance meter, to evaluate driving voltage, light emission luminance, luminous efficiency, luminescent color.Knot Fruit is shown in Table 2, and table 2 is the characteristics of luminescence test knot of the compound of preparation of the embodiment of the present invention and the luminescent device of a-NPD preparation Fruit.
Table 2 is shining for the luminescent device of compound prepared by the embodiment of the present invention and a-NPD and contrast sample preparation Characteristic test result.
Table 2
As known from Table 2, the organic luminescent device that luminous organic material provided by the present invention is prepared as hole transmission layer Luminous efficiency and the service life increase significantly relative to the organic luminescent device prepared by a-NPD as hole transmission layer.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or It changes still within the protection scope of the invention.

Claims (10)

1. a kind of luminous organic material, which is characterized in that it is any one in following structural formula:
In structure above:
R is phenyl or xenyl；
Ar1And Ar2It is each independently selected from the aryl or substituted or unsubstituted C12-30 of substituted or unsubstituted C6-31 Heteroaryl.
2. luminous organic material according to claim 1, which is characterized in that Ar1And Ar2Be each independently selected from substitution or The heteroaryl of the aryl of unsubstituted C10-25 or substituted or unsubstituted C16-24.
3. luminous organic material according to claim 1, which is characterized in that Ar1And Ar2Be each independently selected from substitution or The heteroaryl of the aryl of unsubstituted C14-21 or substituted or unsubstituted C18-22.
4. luminous organic material according to claim 1, which is characterized in that Ar1And Ar2Be each independently selected from substitution or The heteroaryl of the aryl of unsubstituted C16-19 or substituted or unsubstituted C21.
5. luminous organic material according to claim 1, which is characterized in that it is any one in following structures:
6. a kind of preparation method of luminous organic material described in claim 1, which comprises the following steps:
The synthesis of step 1, intermediate
By the de gassed solution N of compound 2 and compound 1 in toluene2Saturation；Then (1,1'- bis- (diphenylphosphines) is added Ferrocene and acid chloride (II), then add NaOtBu；By the reaction mixture heated overnight at reflux；After reaction, cooling To room temperature, water is added, water phase is washed with toluene, uses MgSO4It is dry, and solvent is removed under vacuum；Using heptane/ Ethyl acetate filters crude product via silica gel, obtains intermediate 1；
N- bromo-succinimide is added in the dichloromethane solution of intermediate 1 at 0 DEG C under the conditions of being protected from light, and will The mixture continues to stir at such a temperature；The reaction by add sodium sulfite solution terminate, and again at room temperature after Continuous stirring；After phase separation, organic phase is washed with water, and water phase is extracted with methylene chloride；Combined organic phase is used Sodium sulphate is dry, and evaporates under vacuum；Residue is dissolved in ethyl acetate, and is filtered via silica gel；Then it will slightly produce Object is recrystallized from heptane；Obtain intermediate 2；
Synthetic route is as follows:
The synthesis of step 2, target product
Under nitrogen protection system, intermediate 2 is added into reaction flask, adds compound 3 or compound 4, adds uncle Sodium butoxide and solvent deaerate to reaction system, and catalyst tris(dibenzylideneacetone) dipalladium, three (tert-butyl) phosphines is added, will be anti- It answers the temperature of system to rise to reflux to be reacted, ultrapure water stirring is added after reaction, filters, ethyl alcohol and ultrapure water elution, Target product is obtained after drying；
Compound 3 and 4 structural formula of compound are as follows:
Wherein: R is phenyl or xenyl；Ar1And Ar2Be each independently selected from substituted or unsubstituted C6-31 aryl or The heteroaryl of substituted or unsubstituted C12-30；
L is any one in following structures:
7. a kind of organic luminescent device comprising luminous organic material described in claim 1-5 any one.
8. organic luminescent device according to claim 7 characterized by comprising first electrode, second electrode and be placed in Organic matter layer between two electrode includes organic hair described in claim 1-5 any one in the organic matter layer Luminescent material；The luminous organic material can be single form or be mixed in organic matter layer with other materials.
9. organic luminescent device according to claim 8, which is characterized in that the organic matter layer is injected including at least hole Layer, hole transmission layer had both had hole injection but also with hole transport technical ability layer, electronic barrier layer, luminescent layer, hole barrier Layer, electron transfer layer and both have electron-transport but also with one or more of electron injection technical ability layer at electron injecting layer.
10. can be used for organic luminescent device, organic photovoltaic cell, electricity according to device described in claim 7-9 any one Sub- paper, Organophotoreceptor or Organic Thin Film Transistors.
CN201811180999.7A 2018-10-11 2018-10-11 Luminous organic material and its preparation method and organic luminescent device containing the material Withdrawn CN109180582A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112079731A (en) * 2020-09-18 2020-12-15 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material and preparation method and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160099421A1 (en) * 2014-10-01 2016-04-07 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160099421A1 (en) * 2014-10-01 2016-04-07 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112079731A (en) * 2020-09-18 2020-12-15 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material and preparation method and application thereof
CN112079731B (en) * 2020-09-18 2023-04-28 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material and preparation method and application thereof

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