CN108059643A - A kind of electroluminescent organic material and its organic luminescent device - Google Patents

A kind of electroluminescent organic material and its organic luminescent device Download PDF

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CN108059643A
CN108059643A CN201810048541.XA CN201810048541A CN108059643A CN 108059643 A CN108059643 A CN 108059643A CN 201810048541 A CN201810048541 A CN 201810048541A CN 108059643 A CN108059643 A CN 108059643A
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organic
organic material
electroluminescent
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孙可
孙可一
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of electroluminescent organic material and its organic luminescent device, belongs to organic photoelectrical material technical field.Contain the structure of symmetrical pyrene in the structure of electroluminescent organic material provided by the invention, by phosphine oxide group, effectively interrupt conjugated structure, triplet higher；In addition, electron withdrawing group phosphine oxygen groups, have excellent electron transport ability.The electroluminescent organic material can be applied to as the material of main part in luminescent layer or electron transport material in organic luminescent device, can significantly improve the luminous efficiency of device.

Description

A kind of electroluminescent organic material and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of electroluminescent organic material and its organic hair Optical device.
Background technology
Organic electroluminescent refers to organic material under electric field action, is subject to the excitation of electric current and electric field and luminous shows As.Organic electroluminescent LED (OLED) is the display technology of new generation that display is realized using this phenomenon.From U.S. in 1987 State Kodak Company Tang C.W. and Vanslyke S.A. made the organic electroluminescence device of first function admirable with Come, ORGANIC ELECTROLUMINESCENCE DISPLAYS causes the great interest of people since it has the advantage that.
Existing blue phosphor dopant material essentially from German Novaled, Nippon Steel, light extraction Xing Chandeng overseas enterprises, Efficient dark blue luminescent material can not only be substantially reduced the power consumption of display device, be also used as the master of other low energy emissive materials Body material uses, while blue light material is also the indispensable component for realizing white-light illuminating.But compared to green light and The device level of feux rouges has substantially met practical demand, and the level of blue-light device is lagged, and especially high-performance is deep Blue light material is still more rare, this is mainly due to because blue light material requirement grip smaller and higher thermal stability altogether, this It is conflicting between two requirements are inherent.The mentality of designing of main body blue light material is usually to be conjugated smaller, plane group It is middle to introduce big non-co-planar group.Common core is the preferable anthracene of flatness and fluorenes, the group for introducing non-co-planar be in order to Reduce the muddy thermal stability to go out and improve amorphous thin film of condensed light.Such as common Blue-light emitting host material AND, but it is sent out Optical property is unsatisfactory.
The content of the invention
In view of this, it is an object of the invention to provide a kind of electroluminescent organic material and its organic luminescent device, adopt The organic luminescent device prepared with electroluminescent organic material of the present invention has higher luminous efficiency and lower drive Dynamic voltage.
Present invention firstly provides a kind of electroluminescent organic materials, and general structure is as shown in I：
Wherein, R be selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 arylamine, substitution or not One kind in substituted C24-C50 aryl silicon substrate, substituted or unsubstituted C3-C50 heterocycles.
Preferably, R be selected from substituted or unsubstituted phenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, It is substituted or unsubstituted indenyl, substituted or unsubstituted triphenylamine base, substituted or unsubstituted carbazyl, substituted or unsubstituted Fluorenyl, substituted or unsubstituted silicon tetraphenyl, substituted or unsubstituted dibenzofurans, substituted or unsubstituted dibenzo thiophene One kind in fen, substituted or unsubstituted dibenzo-thiophene dioxide.
Preferably, the electroluminescent organic material, any one in such as lower structure：
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and be placed in two electrode it Between one or more organic compound layers, at least one organic compound layer includes at least one organic electroluminescence of the present invention Luminescent material.
Preferably, the organic compound layer includes luminescent layer, contains Organic Electricity of the present invention in the luminescent layer Electroluminescent material.
Preferably, the organic compound layer includes electron transfer layer, contains in the electron transfer layer of the present invention Electroluminescent organic material.
Beneficial effects of the present invention：
Contain the structure of symmetrical pyrene in the structure of electroluminescent organic material provided by the invention, by phosphine oxide group, Conjugated structure, triplet higher are effectively interrupted.Compared with prior art, it is applied to organic luminescent device, it is special It is not that there is higher luminous efficiency and lower driving voltage as the material of main part in luminescent layer.
On the other hand, strong electron withdrawing group phosphine oxygroup is contained in the structure of electroluminescent organic material provided by the invention Group, since it is with excellent electron transport ability, can also be used as electron transport material, is applied to organic illuminator Part can significantly improve the luminous efficiency of device.
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 part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, the common skill in this field Art personnel all other embodiments obtained without making creative work belong to the model that the present invention protects It encloses.
Present invention firstly provides a kind of electroluminescent organic materials, and general structure is as shown in I：
Wherein, R be selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 arylamine, substitution or not One kind in substituted C24-C50 aryl silicon substrate, substituted or unsubstituted C3-C50 heterocycles.
According to the present invention, the aryl refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left monad radical The general name of group can be monocyclic aryl or fused ring aryl, such as may be selected from phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrene Base etc., but not limited to this.
The arylamine refers to the amine with armaticity substituent group, i.e.-NH2,-NH- or nitrogen-containing group be connected on aromatic hydrocarbon.
The aryl silicon substrate refers to the silane of at least one armaticity substituent group substitution, such as tetraphenyl silane.
The heterocycle refers to the group that carbon atom is substituted by hetero atom on one or more of cyclic hydrocarbon radical ring General name, the hetero atom include but not limited to oxygen, sulphur and nitrogen-atoms, and the aromatic heterocycle can be monocyclic or condensed ring, such as can Selected from pyridyl group, pyrimidine radicals, oxadiazolyls, thiadiazolyl group, benzo pyrimidine radicals, carbazyl, dimethyl acridinium base, triazine radical, benzene Benzothiazolyl or benzimidazolyl etc., but not limited to this.
It is described in the substituted aryl, the arylamine substituted, the aryl silicon substrate substituted, the heterocycle substituted in the present invention Substituent group refers to the group that organic compound group removes one or several-H and formed, such as methyl, ethyl, isopropyl, tertiary fourth Base, phenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl,Base, pyrenyl, fluoranthene base, base, tolyl, methoxyl group, methyl mercapto, benzene Oxygroup, thiophenyl, fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, hexichol amido, dimethylamino, carbazyl, carbazole Diindyl base, phenyl substituted carbazole base, dibenzofuran group, dibenzothiophene, dibenzo dioxy thienyl, cyano, it is fluorine-based, Deuterium base, two phenenyl phosphinyl, phenyl sulfuryl, phenylsulfone base, triphenyl silicon substrate, trimethyl silicon substrate, phenothiazinyl, phenoxazine Base, acridinyl, dimethyl acridinium, diphenylacridine, dibenzo piperidyl, pyridyl group, pyrimidine radicals, pyridazinyl, pyrazinyl, triazine Ji, oxadiazolyls, thiadiazolyl group, triazol radical, xenyl, terphenyl, indyl, indenyl, phenanthroline base, nitro etc., but It is without being limited thereto.
Preferably, R be selected from substituted or unsubstituted phenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, It is substituted or unsubstituted indenyl, substituted or unsubstituted triphenylamine base, substituted or unsubstituted carbazyl, substituted or unsubstituted Fluorenyl, substituted or unsubstituted silicon tetraphenyl, substituted or unsubstituted dibenzofurans, substituted or unsubstituted dibenzo thiophene One kind in fen, substituted or unsubstituted dibenzo-thiophene dioxide.It is no longer superfluous herein described in the substituent group is defined as above It states.
Preferably, the electroluminescent organic material, selected from such as any one in lower structure：
Electroluminescent organic material of the present invention can be prepared by following reaction scheme：
Grignard reagent is made in bromination pyrene first, generation phosphite ester reagent is reacted with di(2-ethylhexyl)phosphate ethyl fat, in urging for Ni Under change, reacted with boron acidizing reagent into the electroluminescent organic material shown in Formulas I.
Wherein, R be selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 arylamine, substitution or not One kind in substituted C24-C50 aryl silicon substrate, substituted or unsubstituted C3-C50 heterocycles.
The present invention also provides a kind of organic luminescent device, what the organic luminescent device was well known to those skilled in the art Organic luminescent device.Organic luminescent device of the present invention includes first electrode, second electrode and is placed between two electrodes One or more organic compound layers, at least one organic compound layer includes at least one organic electroluminescence of the present invention Luminescent material.The organic compound layer preferably includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electronics At least one layer in transport layer and electron injecting layer, containing of the present invention in preferably described luminescent layer or electron transfer layer Electroluminescent organic material.
Embodiment 1：The preparation of compound 1
Step1. 10mmol 2- bromine pyrenes are taken, a small amount of anhydrous THF dissolvings is added in, is heated to 40 DEG C, under nitrogen protection, adds in 200mmol magnesium powders add in two iodine and make initiator, stir to system and become cloudy, and the THF for continuing to be added dropwise 90mmol2- bromine pyrenes is molten Liquid, stirring 0.5 it is small when after be warming up to reflux, the reaction was continued 3 it is small when.After the completion of reaction, reaction system is cooled to 0 DEG C.
Step2. the THF solution of ethyl phosphonic acid ester is added drop-wise in above-mentioned reaction solution, under 0 DEG C, nitrogen protection, continued anti- Answer 6 it is small when.After the completion of reaction, water and DCM are added in, liquid separation, concentration, drying, silicagel column excessively obtain 1-1 65mmol.
Step3. 1-1 65mmol are added in reaction vessel, 1.5 equivalent of phenyl boric acid, 1 equivalent of potassium carbonate, NiBr 0.2 ought Amount, the dichloroethanes of ultrasonic deoxygenation, stirring and dissolving, displaced air three times, add in 0.3 equivalent of pyridine, again displaced air three times, Back flow reaction is for 24 hours.It is cooled to room temperature, excessively a small amount of silica gel funnel removes catalyst and salt.Filtrate is concentrated into thick, mistake column layer Analysis, obtains 1 50mmol of product.
Embodiment 2：The preparation of compound 8
Phenyl boric acid in Step3 is replaced with (9- phenyl -9H- carbazole -3- bases) boric acid by synthetic method with embodiment 1.
Embodiment 3：The preparation of compound 21
Phenyl boric acid in Step3 is replaced with (9,9- dimethyl -9H- fluorenes -3- bases) boric acid by synthetic method with embodiment 1.
Embodiment 4：The preparation of compound 30
Phenyl boric acid in Step3 is replaced with (4- (triphenyl silicon substrate) phenyl) boric acid by synthetic method with embodiment 1.
Compound FD-MS values prepared by 1 embodiment of the present invention of table
Compound FD-MS
1 M/z:526.28, C38H23OP (526.15)
8 M/z:693.41, C50H32NOP (693.22)
21 M/z:644.40, C47H33OP (644.23)
30 M/z:786.05, C56H39OPSi (786.25)
Compare Application Example 1：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layer NPBEmitting layer material AND is deposited:Dopant 5%DPAVBiThen electron transfer layer is deposited Alq3 CathodeAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Application example 1：
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layer NPBEmitting layer material AND is deposited:5% compound 8 of dopantThen electron transfer layer is deposited Alq3 CathodeAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Application example 2：
Compound 8 in Application Example 1 is changed to compound 21.
Application example 3：
Compound 8 in Application Example 1 is changed to compound 30.
Measure embodiment 1：Compare the luminescent properties of sample and sample
Comparison sample and sample are using Keithley SMU235, PR650 evaluation luminous efficiencies and driving voltage, knot Fruit is listed in Table 2 below：
The characteristics of luminescence of luminescent device prepared by 2 embodiment of the present invention of table
Compare Application Example 2：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole transport is deposited Layer NPBEmitting layer material AND is deposited:Dopant 5%DPAVBiThen electron transfer layer Alq is deposited3 Cathode LiFAlAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Application example 4：
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole transport is deposited Layer NPBEmitting layer material AND is deposited:Dopant 5%DPAVBiThen electron transfer layer chemical combination is deposited Object 1Cathode LiFAlAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Measure embodiment 2：Compare the luminescent properties of sample and sample
Comparison sample and sample are using Keithley SMU235, PR650 evaluation luminous efficiencies and driving voltage, knot Fruit is listed in Table 3 below：
The characteristics of luminescence of luminescent device prepared by 3 embodiment of the present invention of table
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim In the case of the spirit and scope of the invention limited, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (6)

1. a kind of electroluminescent organic material, general structure is as shown in I：
Wherein, R is selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 arylamine, substitution or unsubstituted C24-C50 aryl silicon substrate, one kind in substituted or unsubstituted C3-C50 heterocycles.
2. a kind of electroluminescent organic material according to claim 1, which is characterized in that R is selected from substituted or unsubstituted It is phenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted Triphenylamine base, substituted or unsubstituted carbazyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silicon tetraphenyl, substitution Or unsubstituted dibenzofurans, substituted or unsubstituted dibenzothiophenes, substituted or unsubstituted dibenzo-thiophene dioxide In one kind.
3. a kind of electroluminescent organic material according to claim 1, which is characterized in that arbitrary in such as lower structure It is a kind of：
4. a kind of organic luminescent device, including first electrode, second electrode and the one or more being placed between two electrode Organic compound layer, which is characterized in that at least one organic compound layer includes at least one such as any one of claims 1 to 3 Described in electroluminescent organic material.
5. a kind of organic luminescent device according to claim 4, which is characterized in that the organic compound layer includes shining Layer, the electroluminescent organic material as described in any one of claims 1 to 3 is contained in the luminescent layer.
6. a kind of organic luminescent device according to claim 4, which is characterized in that the organic compound layer includes electronics Transport layer contains the electroluminescent organic material as described in any one of claims 1 to 3 in the electron transfer layer.
CN201810048541.XA 2018-01-18 2018-01-18 A kind of electroluminescent organic material and its organic luminescent device Withdrawn CN108059643A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109054810A (en) * 2018-09-05 2018-12-21 黑龙江大学 Using diphenylsulfide as the thermal excitation delayed fluorescence material of main part of parent and its preparation and application
CN111848617A (en) * 2019-04-25 2020-10-30 上海钥熠电子科技有限公司 Organic electroluminescent material and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109054810A (en) * 2018-09-05 2018-12-21 黑龙江大学 Using diphenylsulfide as the thermal excitation delayed fluorescence material of main part of parent and its preparation and application
CN111848617A (en) * 2019-04-25 2020-10-30 上海钥熠电子科技有限公司 Organic electroluminescent material and application thereof
CN111848617B (en) * 2019-04-25 2022-02-22 上海钥熠电子科技有限公司 Organic electroluminescent material and application thereof

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