CN109336812A - Organic luminescent compounds and preparation method thereof and organic electroluminescence device containing the compound - Google Patents

Organic luminescent compounds and preparation method thereof and organic electroluminescence device containing the compound Download PDF

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CN109336812A
CN109336812A CN201811180993.XA CN201811180993A CN109336812A CN 109336812 A CN109336812 A CN 109336812A CN 201811180993 A CN201811180993 A CN 201811180993A CN 109336812 A CN109336812 A CN 109336812A
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formula
compound
structure shown
reaction
organic luminescent
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王辉
马晓宇
李文军
王进政
汪康
李贺
毕岩
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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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Priority to CN201811180993.XA priority Critical patent/CN109336812A/en
Priority to PCT/CN2018/120962 priority patent/WO2020073479A1/en
Publication of CN109336812A publication Critical patent/CN109336812A/en
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Abstract

The present invention relates to technical field of organic luminescence materials, and in particular to a kind of organic luminescent compounds and preparation method thereof and the organic electroluminescence device containing the compound.A kind of organic luminescent compounds provided by the invention, it is to combine the tri-arylamine group for having the acridine functional group of high electron hole efficiency of transmission excellent with hole transport performance, it is high to form a kind of thermal stability, the excellent compound of luminous efficiency, the introducing of different substituents, electron transition can be changed, keep its luminous peak position adjustable, can satisfy the demand of industrialized production with the red device that material of the invention is fabricated to.The preparation method of organic luminescent compounds provided by the invention, preparation method is simple, is suitable for industrialized production, and the superior compound of performance can be prepared by adjusting reactant amount ratio and reaction time and temperature.Organic luminescent device provided by the invention, with excellent luminous efficiency, brightness, resolution ratio, and the service life is long.

Description

Organic luminescent compounds and preparation method thereof and organic electroluminescent containing the compound Device
Technical field
The present invention relates to technical field of organic luminescence materials, and in particular to a kind of organic luminescent compounds and preparation method thereof With the organic electroluminescence device containing the compound.
Background technique
Organnic electroluminescent device (organic electroluminescent device), also referred to as organic light emission two Pole pipe (organic light-emitting diode；OLED), it is a kind of light emitting diode using organic layer as active layers (LED).Since Organnic electroluminescent device has low voltage operating, high brightness, light-weight, wide viewing angle and high reduced value etc. Advantage has been used in gradually in recent years on flat panel display (flat panel display).It is different from liquid crystal display, The organic LED pixels array that display of organic electroluminescence is included is that have self luminous characteristic, therefore be not required to outer Add backlight.In general, Organic Light Emitting Diode component includes a pair of electrodes, and organic light emission Jie between the electrodes Matter layer.Under the action of extra electric field, electrons and holes are situated between from cathode and anode to the organic light emission of folder between the electrodes respectively The injection of matter layer, injected electrons and hole are migrated from electron transfer layer and hole transmission layer to luminescent layer respectively, electrons and holes It meets and generates exciton (excitons) in organic light emitting medium layer, exciton is constantly made freely to expand in organic light emitting medium layer Load in bulk it is dynamic, and with radiation or radiationless mode inactivate, when exciton returns to ground state by excitation state in a manner of radiation transistion, so that it may To observe electro optical phenomenon, the color for emitting light is determined by the energy level difference of excitation state to ground state.
According to the spin state (spin state) in hole and electronics, by hole and electronics in conjunction with and the exciton that generates can Spin state with triplet (triplet) or singlet state (singlet).By singlet excitons (singlet exciton) institute What is generated shines as fluorescence (fluorescence), and shines as caused by triplet exciton (triplet exciton) and be Phosphorescence (phosphorescence).The luminous efficiency of phosphorescence is three times of fluorescence.Therefore, develop efficient phosphor material with The luminous efficiency for promoting Organic Light Emitting Diode component is very important.
Summary of the invention
The object of the present invention is to provide a kind of organic luminescent compounds and preparation method thereof and containing the Organic Electricity of the compound Electroluminescence device.Organic luminescent compounds of the invention are acridine functional group and the sky that will have high electron hole efficiency of transmission The excellent tri-arylamine group combination of cave transmission performance, forms a kind of thermal stability height, the excellent compound of luminous efficiency.
To achieve the goals above, technical solution of the present invention is specific as follows:
A kind of organic luminescent compounds, shown in general structure such as formula (I):
In formula: R1Any one in following structures:
Wherein " * " refers to the position being connected with N atom；
In formula: R2Any one in following structures:
Wherein " * " refers to the position being connected with phenyl ring；
L isOr it isConnecting key between phenyl ring；
Ar1And Ar2It is each independently selected from the aryl of substituted or unsubstituted C6-C25 or substituted or unsubstituted The heteroaryl of C12-C22.
In the above-mentioned technical solutions, Ar1And Ar2Be each independently selected from substituted or unsubstituted C10-C21 aryl or The heteroaryl of the substituted or unsubstituted C16-C18 of person.
In the above-mentioned technical solutions, Ar1And Ar2It is each independently selected from the aryl of substituted or unsubstituted C12-C17.
In the above-mentioned technical solutions, Ar1And Ar2It is each independently selected from the aryl of substituted or unsubstituted C13-C14.
In the above-mentioned technical solutions, the organic luminescent compounds are any one in following structures:
A kind of preparation method of organic luminescent compounds, comprising the following steps:
(1) there will be the compound of structure shown in formula (II) compound with structure shown in formula (III) or formula (IV) respectively Reaction, obtains the compound of structure shown in formula (V) or formula (VI)；
(2) compound of structure shown in formula (V) or formula (VI) is reacted with the compound of structure shown in formula (VII) respectively, Obtain the compound of structure shown in formula (I)；
In the above-mentioned technical solutions, the compound of structure shown in the formula (II) is prepared by the following method:
The change of structure shown in compound reaction production (B) of structure shown in the compound and formula (C) of structure shown in formula (A) Close object, the compound of structure shown in formula (B) again with R2Grignard Reagent reaction generate formula (II) shown in structure compound；
Wherein, X in formula (C)1And X2It independently selected from halogen, and is not simultaneously same halogen；X is X1Or X2。
According to the present invention, the present invention will have the compound and formula (III) or the shown knot of formula (IV) of structure shown in formula (II) The compound of structure reacts, and obtains the compound of structure shown in formula (V) or formula (VI)；The compound of structure shown in the formula (II) with The molar ratio of the compound of structure shown in formula (III) or formula (IV) is 1:(0.9~1.6)；The catalyst of the reaction is preferably Tetra-triphenylphosphine palladium；The alkali of the reaction is sodium carbonate；The temperature of the reaction is preferably 130~180 DEG C, more preferably 150 ~160 DEG C；The time of the reaction is preferably 20~40 hours, and more preferably 24~30 hours.
The source of the compound of structure shown in compound and formula (III) or formula (IV) of the present invention to structure shown in formula (II) It is not particularly limited, is made by preparation method well known in the art.
According to the present invention, the present invention by the compound of structure shown in formula (V) or formula (VI) respectively with structure shown in formula (VII) Compound reaction, obtain the compound of structure shown in formula (I)；Wherein, R1And R2The selection of group and L are as hereinbefore；It is described The molar ratio of the compound of structure shown in the compound and formula (VII) of structure shown in formula (V) or formula (VI) is 1:(0.9~1.6)； Alkali used is sodium tert-butoxide in the reaction, and the catalyst of the reaction is acid chloride and tri-tert-butylphosphine；The temperature of the reaction Preferably 130~180 DEG C, more preferably 150~160 DEG C of degree；The time of the reaction is preferably 20~40 hours, more preferably 24~30 hours.
According to the present invention, the present invention will have the compound of structure shown in formula (A) and the compound of structure shown in formula (C) anti- It answers, obtains the compound of structure shown in formula (B)；The compound of structure shown in the compound and formula (C) of structure shown in the formula (A) Molar ratio be (0.9~1.6): 1；The catalyst of the reaction is preferably palladium acetate；The alkali of the reaction is sodium tert-butoxide；Institute The temperature for stating reaction is preferably 130~180 DEG C, and more preferably 150~160 DEG C；The time of the reaction is preferably 20~40 small When, more preferably 24~30 hours.
According to the present invention, the present invention will have the compound and R of structure shown in formula (B)2Grignard Reagent reaction, obtain formula (II) compound of structure shown in, wherein R2The selection of group is as hereinbefore；The compound and R of structure shown in the formula (B)2 Grignard Reagent molar ratio be 1:(1~3)；The temperature of the reaction is preferably 0 DEG C~5 DEG C；More preferably 0 DEG C；It is described anti- The time answered is preferably 0.5~4 hour, and more preferably 1~3 hour.
The present invention also provides a kind of compounds of formula (I) structure of the present invention to prepare organic electroluminescence device In application；
Specifically, the organic electroluminescence device is preferably, comprising:
First electrode, second electrode and the organic matter layer being placed between two electrode, wherein wrapped in the organic matter layer Compound containing structure shown in formula (I)；The compound of structure shown in formula (I) can be single form or mix with other materials It is present in organic matter layer.
Wherein, the organic matter layer includes at least hole injection layer, hole transmission layer, had both had hole injection but also with sky Technical ability layer is transmitted in cave, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both has electronics biography It is defeated but also with one or more of electron injection technical ability layer.
The hole injection layer, the hole transmission layer, it is described both had hole injection but also with hole transport technical ability layer In at least one be conventional hole injecting material, hole transporting material or both have hole injection but also with hole transport Technical ability substance, it is also possible to be the substance that electron-transporting material generates.
Of the present invention includes that the device of the compound preparation of formula (I) structure can be used for organic luminescent device (OLED), organic photovoltaic cell (OSC), Electronic Paper (e-Paper), Organophotoreceptor (OPC) or Organic Thin Film Transistors (OTFT)。
Device of the present invention can be by the methods of film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) in substrate Upper evaporation metal and conductive oxide and their alloy form anode, can also use spin-coating (spin- Coating) or strip takes the lead to be deposited；It can also be using molding (tape-casting), scraping blade method (doctor-blading), silk The methods of wire mark brush (Screen-Printing), ink jet printing or thermal imaging (Thermal-Imaging) reduce number of plies manufacture.
The beneficial effects of the present invention are:
Compared with prior art, the present invention proposes a kind of organic luminescent compounds, is will have high electron hole to transmit The tri-arylamine group that the acridine functional group of efficiency is excellent with hole transport performance combines, and forms a kind of thermal stability height, hair The excellent compound of light efficiency, the introducing of different substituents can change electron transition, keep its luminous peak position adjustable, with this The device that the material of invention is fabricated to can satisfy the demand of industrialized production.
The preparation method of organic luminescent compounds provided by the invention, preparation method is simple, is suitable for industrialized production, and lead to The superior compound of performance can be prepared by overregulating reactant amount ratio and reaction time and temperature.
Organic electroluminescence device provided by the invention, with excellent luminous efficiency, brightness, resolution ratio, and longevity Life length.
Specific embodiment
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common Technical staff's every other embodiment obtained without making creative work belongs to the model that the present invention protects It encloses.
The preparation of intermediate formula (B) structural compounds
100mL there-necked flask is taken, bromo- 4- iodobenzene (C) 24.0mmol of 20.0mmol starting material (A), 1-, iodate are respectively put into Cuprous 1.0mmol, Phen 4mmol, cesium carbonate 40mmol, degassing is three times, it is ensured that W-response is in nitrogen system, is added Dry toluene solvent 30mL, and the return pipe reflux condensation mode on reaction flask is determined using TLC piece and reacted after reaction 4 hours Terminate, be down to room temperature, filter, and filtered and cleaned with methylene chloride, collect filtrate, rotary evaporation obtains yellowish liquid, column layer Analysis is eluent using n-hexane/ethyl acetate=9:1, carries out purifies and separates, can finally obtain product B-1, yield about 85%.
The preparation of intermediate formula (II) structural compounds
100mL there-necked flask is taken, is put into 10.0mmol compound B-1, degassing is three times, it is ensured that W-response is in nitrogen system System, is added anhydrous THF solvent 20mL, is later placed in reaction flask in 0 DEG C of cold well, after total system temperature reaches balance, It using needle aspirate 12.0mmol xenyl magnesium bromide, is slowly added drop-wise in reaction flask, after maintaining low-temp reaction 1 hour, allows whole Precursor reactant is slowly reacted by 0 DEG C to room temperature.After reacting two hours at room temperature, reaction end is confirmed through TLC.20mL is added to be saturated Aqueous ammonium chloride solution is quenched, liquid separation, concentration.It will obtain intermediate to be added directly into without further purification in 100mL there-necked flask, add Enter 30mL toluene solvant and the methanesulfonic acid of 20mmol, be heated to flow back, reacts 3 hours, W-response is allowed to be cooled to room temperature.Through TLC confirms reaction end.Reaction solution is added drop-wise in 150mL aqueous solution, is filtered, drying.To obtain solid using column chromatograph into Row purifying is eluent using petrol ether/ethyl acetate=1:1, carries out purifies and separates, can finally obtain product II-1, yield is about 78%.
Formula (II-2)~formula (II-8) synthetic method is similar with the synthetic method of formula (II-1), synthesis raw material and Product and yield are shown in Table 1；
Table 1
The preparation of intermediate (V) and (VI)
Under nitrogen protection system, 10.0mmol intermediate II -1 and intermediate III -1 12.0mmol is added, carbonic acid is added Sodium 25mmol and solvent 30mL, solvent are toluene and water, and ratio 2:1 deaerates to reaction system, and four triphenyl of catalyst is added The temperature of reaction system is risen to reflux, reacted 24 hours, use petroleum ether: methylene chloride=2:1 is tied again by phosphine palladium 0.2mmol Crystalline substance obtains intermediate V-1, yield 75%.
Under nitrogen protection system, 10.0mmol intermediate II -1 and intermediate compound IV -1 12.0mmol is added, tertiary fourth is added Sodium alkoxide 30mmol and solvent 30mL, solvent are dry toluene.It deaerates, is added catalyst three (dibenzalacetone) to reaction system The temperature of reaction system is risen to reflux by two palladium 0.1mmol, three (tert-butyl) phosphine 1mmol, is reacted 12 hours.After reaction plus Enter ultrapure water stirring, filter, ethyl alcohol and ultrapure water elution obtain VI-1 after drying.
The synthetic method of product shown in V-2~V-4 and the synthetic method of V-1 are similar.
The synthetic method of product shown in VI-2~VI-13 and the synthetic method of VI-1 are similar.
Its raw material and product synthesized and yield are shown in Table 2.
Table 2
The preparation of target product formula (I) structural compounds
Embodiment 1
Under nitrogen protection system, 10mmL intermediate VI-1 and 12mmL intermediate VII-1 is added, sodium tert-butoxide is added 30mmol and solvent 30mL, solvent are dry toluene.It deaerates to reaction system, (the dibenzylidene third of 0.1mmol catalyst three is added Ketone) two palladiums, the temperature of reaction system rises to reflux, reacted 12 hours by (tert-butyl) phosphine of 1mmol tri-.It is added after reaction super Pure water stirring, filters, and ethyl alcohol and ultrapure water elution obtain compound 21, mass spectrometry value 625.32 after drying.
Intermediate VI-1 in above-described embodiment is replaced with into intermediate V-1, compound 1 is prepared, mass spectrometry value is 701.30。。
The synthetic method of other compounds is similar with the synthetic method of compound 1, the raw material and product and receipts of synthesis Rate is shown in Table 3.
Table 3
With the preparation method of embodiment 1, R in replacing structure formula (1)1、R2、Ar1、Ar2, L substituent group it is available different Target product is just not listed one by one here.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention Protect range.
Compound shown in obtained formula (I) is tested for the property
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.4,4', 4 "-three [the 2- naphthylphenyl amino] three for being 50nm by evaporation thickness on the ito transparent electrode having had been prepared for Phenyl amine (2-TNATA) is used as hole injection layer.Then by the compound of above-mentioned preparation 1,6,13,19,21,33,38,50,64, 71,72,73,75,77,81,84,90, a-NPD or comparative example on the hole injection layer of formation vacuum evaporation with a thickness of The hole transmission layer of 30nm.Then the blue material of main part 9 that evaporation thickness is 30nm on above-mentioned hole transmission layer, bis- (2- of 10- Naphthalene) anthracene (ADN) and dopant material N1, N1, N6, N6- tetraphenyl pyrene -1,6- diamines (TPPDA).Material of main part and dopant material Weight ratio be 95:5.Then on above-mentioned luminescent layer vacuum evaporation with a thickness of 40nm TPBi as hole blocking layer and electronics Transport layer.Vacuum evaporation is on above-mentioned electron transfer layer with a thickness of 0.5nm lithium fluoride (LiF), as electron injecting layer.Finally steam The aluminium with a thickness of 150nm is plated as cathode, the preparation of organic electroluminescence device is completed with this.Performance to obtained device Characteristics of luminescence test measures and uses 2400 type source measuring unit of KEITHLEY Keithley, CS-2000 spectroradio luminance meter, with Evaluate driving voltage, light emission luminance, luminous efficiency, luminescent color.It the results are shown in Table 4, table 4 is the chemical combination of preparation of the embodiment of the present invention The characteristics of luminescence test result of object and the luminescent device of a-NPD preparation.
Comparative example
Table 4 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 4
As known from Table 4, the organic electroluminescence hair that organic luminescent compounds provided by the present invention are prepared as hole transmission layer The luminous efficiency of optical device and service life are relative to the Organic Electricity prepared by a-NPD and comparative example respectively as hole transmission layer Electroluminescence device increases significantly.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims (10)

1. a kind of organic luminescent compounds, which is characterized in that shown in its general structure such as formula (I):
In formula: R1Any one in following structures:
Wherein " * " refers to the position being connected with N atom；
In formula: R2Any one in following structures:
Wherein " * " refers to the position being connected with phenyl ring；
L isOr it isConnecting key between phenyl ring；
Ar1And Ar2It is each independently selected from the aryl or substituted or unsubstituted C12-C22 of substituted or unsubstituted C6-C25 Heteroaryl.
2. organic luminescent compounds according to claim 1, which is characterized in that Ar1And Ar2It is each independently selected from substitution Or unsubstituted C10-C21 aryl or substituted or unsubstituted C16-C18 heteroaryl.
3. organic luminescent compounds according to claim 1, which is characterized in that Ar1And Ar2It is each independently selected from substitution Or the aryl of unsubstituted C12-C17.
4. organic luminescent compounds according to claim 1, which is characterized in that Ar1And Ar2It is each independently selected from substitution Or the aryl of unsubstituted C13-C14.
5. organic luminescent compounds according to claim 1, which is characterized in that the organic luminescent compounds are following knots Any one in structure:
6. a kind of preparation method of organic luminescent compounds described in claim 1-5 any one, which is characterized in that including with Lower step:
(1) compound with structure shown in formula (II) is reacted with the compound of structure shown in formula (III) or formula (IV) respectively, Obtain the compound of structure shown in formula (V) or formula (VI)；
(2) compound of structure shown in formula (V) or formula (VI) is reacted with the compound of structure shown in formula (VII) respectively, is obtained The compound of structure shown in formula (I)；
7. the preparation method of organic luminescent compounds according to claim 6, which is characterized in that structure shown in formula (II) Compound is prepared by the following method:
The chemical combination of structure shown in compound reaction production (B) of structure shown in the compound and formula (C) of structure shown in formula (A) Object, the compound of structure shown in formula (B) again with R2Grignard Reagent reaction generate formula (II) shown in structure compound；
Wherein, X in formula (C)1And X2It independently selected from halogen, and is not simultaneously same halogen；X is X1Or X2。
8. the preparation method of organic luminescent compounds according to claim 6, which is characterized in that
The molar ratio of the compound of structure shown in the compound and formula (III) or formula (IV) of structure shown in the formula (II) is 1: (0.9~1.6)；The catalyst of the reaction is preferably tetra-triphenylphosphine palladium；The alkali of the reaction is sodium carbonate；The reaction Temperature is 130~180 DEG C；The time of the reaction is 20~40 hours；
The molar ratio of the compound of structure shown in the compound and formula (VII) of structure shown in the formula (V) or formula (VI) is 1: (0.9~1.6)；Alkali used in the reaction is sodium tert-butoxide, and the catalyst of the reaction is acid chloride and tri-tert-butylphosphine；It is described The temperature of reaction is 130~180 DEG C；The time of the reaction is 20~40 hours.
9. the preparation method of organic luminescent compounds according to claim 6, which is characterized in that
The temperature of step (1) described reaction is 150~160 DEG C, and the time of reaction is 24~30 hours；
The temperature of step (2) described reaction is 150~160 DEG C, and the time of reaction is 24~30 hours.
10. a kind of organic electroluminescence device, including first electrode, second electrode and the organic matter being placed between two electrode Layer, which is characterized in that the chemical combination comprising structure shown in formula (I) described in claim 1-5 any one in the organic matter layer The compound of object, structure shown in the formula (I) is single form or is mixed in organic matter layer with other materials.
CN201811180993.XA 2018-10-11 2018-10-11 Organic luminescent compounds and preparation method thereof and organic electroluminescence device containing the compound Pending CN109336812A (en)

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