CN107936038A - A kind of OLED electron transport layer materials and its preparation method and application - Google Patents

A kind of OLED electron transport layer materials and its preparation method and application Download PDF

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Publication number
CN107936038A
CN107936038A CN201711171797.1A CN201711171797A CN107936038A CN 107936038 A CN107936038 A CN 107936038A CN 201711171797 A CN201711171797 A CN 201711171797A CN 107936038 A CN107936038 A CN 107936038A
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electron transport
electron
oled
transport materials
groups
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孟鸿
姚超
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Peking University Shenzhen Graduate School
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Peking University Shenzhen Graduate School
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Parent nucleus of the present invention using BTBT as electron transport material, the parent nucleus have excellent flatness, crystallinity and carrier transmission performance.By at least one middle electrophilic end-capping group for introducing nitrogenous aromatic heterocycle at both ends, the lumo energy of system is reduced, so as to improve the electronic transmission performance of material.Meanwhile BTBT brings material higher triplet as parent nucleus, be conducive to improve the stability of device.The OLED electron transport materials of the present invention have higher electronic transmission performance, and good film-forming property, at room temperature with preferable stability, therefore can reduce driving voltage, and preferable stability causes device work more to stablize at room temperature, and physical life is longer.

Description

A kind of OLED electron transport layer materials and its preparation method and application
Technical field
The present invention relates to luminous organic material field, more particularly to OLED electron transport layer materials and preparation method thereof and should With.
Background technology
OLED, refers to organic electroluminescence device.Since its is bright, visual angle is wide, temperature model compatible with full-motion video Enclose that wide, form factor is thin and suitable, power demand is low and with the potential for being used for inexpensive manufacturing process, so OLEDs is seen Work is the future replacement technology of cathode-ray tube (CRTs) and liquid crystal display (LCDs).Since its luminous efficiency is high, OLEDs quilts Regard as with substitute incandescent lamp and perhaps in addition fluorescent lamp potential.At present, OLED display screen is by Samsung, LG, apple etc. Company has been applied to smart mobile phone field, while people are also widely used MP3/ TVs based on OLED display screen and white The products such as optical illumination have realized the Perfect Experience that OLED is brought.
Organic electroluminescence device has structure of whole solid state, and electroluminescent organic material is the core of device, new material Exploitation is to promote the power of electroluminescent technology development, prepared by raw material and device optimization also becomes present organic electroluminescence and sends out The research hotspot of light industry.In order to meet people for showing product increasingly higher demands, scientists are directed to synthesis more For efficient electron transport material, shine Subjective and Objective material and hole mobile material etc..
The hole mobility of hole mobile material is typically much deeper than the electron mobility of electron transport material in OLED device, This carrier transport speed imbalance can bring being remarkably decreased for device performance.Therefore the electric transmission material of excellent is designed Expect extremely important.Usually, electron transport material is all the plane aromatic compound for having big conjugated structure, they are big There is preferable electron acceptability more, while electronics can be effectively transmitted again under certain forward bias.It is currently available Electron transport material mainly have 8-hydroxyquinoline aluminium class compound, furodiazole compound, glyoxaline compound, oxazole class Compound, triazole class compounds, nitrogenous hexa-member heterocycle class, perfluorinate electron-like transmission material, organic silicon electron transport material etc.. An electron transport material that can be obviously improved organic electroluminescence device efficiency will be designed by designing one, need to be possessed following Property：Reversible electrochemical reduction stability and higher reduction potential；There are suitable HOMO and LUMO electronics is had minimum Energy gap is injected, voltage is originated and operate to reduce；Need higher electron mobility；With good glass transition temperature and heat Stability；Noncrystalline film can be effectively formed.
But electron transport material traditional at present includes Alq3, TAZ, TPBi, Bphen, BCP etc. electron mobility all It is not very high, it is caused compared with the higher hole mobility of hole mobile material material unbalanced to seriously affect device Stability.At the same time with the development of blue emitting phosphor device and white light parts, the low triplet state of these materials cannot effectively Excitons in luminescent layer, the diffusion of exciton with it is compound be quenched can largely influence device light emitting efficiency and shine it is pure Degree.In addition for the glass transition temperature of these materials than relatively low, this heat for causing to produce in device operation brings material The crystallization of material itself, the stability of device can reduce.
The content of the invention
In view of above-mentioned the deficiencies in the prior art, it is an object of the invention to provide a kind of Novel electronic transmission material and its system Preparation Method and application, it is intended to solve that existing electron transport material electron mobility is low, glass transition temperature is low and three lines The shortcomings that state energy level is low.The present invention introduces [1] benzothieno [3,2-b] [1] in electron transport material structure first Benzothiophene (BTBT) is parent nucleus, there is provided smooth and electron rich a conjugate planes, such structure are conducive to Electronics flowing is so as to improve material electronics mobility.The electron withdrawing group of nitrogenous aromatic heterocycle, effectively drop are introduced at parent nucleus both ends Low lumo energy, is conducive to electric transmission；Simultaneously as the effect of nitrogen-atoms lone electron pair and lithium ion, enhances electronics note Enter ability.In addition, the symmetrical structure of molecule can increase the regularity of molecular stacks, so as to improve material carrier migration Rate.Therefore this material, has higher electronic transmission performance, good film-forming property, has higher stability, vitrifying at room temperature Transition temperature is high, is a kind of up-and-coming electron transport material.
The technical solution that the present invention solves above-mentioned technical problem is as follows：
On the one hand, the present invention relates to a kind of OLED electron transport materials material, its molecular structural formula can with and be not limited to as Under：
Wherein, Ar gene expressions are the aromatic heterocycle with electron performance or electron-withdrawing energy, can be but be not limited to Phenyl, naphthyl, anthryl, thienyl, bithiophene base, pyridine radicals, pyrimidine radicals, quinolyl, isoquinolyl, indyl, isoindolyl, Thiazolyl, oxazolyl, benzothiazolyl, diazosulfide base, naphthyridines base, pyridazinyl, pyrimidine radicals, pyrazinyl etc..Meanwhile Ar bases At least one in group is nitrogenous aromatic heterocycle.
Meanwhile Ar groups can be that the electron withdrawing groups such as above-mentioned group is substituted by fluorine, trifluoromethyl substitutes, cyano group substitutes take The derivative in generation.
On the other hand, the present invention provides a kind of method for preparing OLED electron transfer layers, compound A (2,7- is utilized Dibromo [1] benzothieno [3,2-b] [1] benzothiophene) and electrophilic heterocyclic boronic acids ester (B) generation Suzuki Coupling is so as to obtain corresponding electron transport material.Reaction equation is as follows：
Wherein, solvent uses tetra-triphenylphosphine palladium using toluene, water, ethanol mixed system, catalyst, and reaction temperature is 100 degrees Celsius, reaction time 24h.
The present invention also provides a kind of application of new OLED electron transport materials, in organic electroluminescence device, at least There is a functional layer to contain above-mentioned new OLED electron transport materials.
The present invention also provides a kind of organic electroluminescence device, including the anode layer and cathode layer of a pair of electrodes are formed, with And luminescent layer and electron transfer layer between the anode layer and the cathode layer, the electron transfer layer contain above-mentioned new OLED electronics Transmission material.
New OLED electron transport materials provided by the invention have higher electronic transmission performance, good film-forming property, in room Temperature is lower to have preferable stability, therefore can reduce driving voltage, and preferable stability causes device work more at room temperature Add stabilization, physical life is longer.
Brief description of the drawings
Fig. 1 is the molecular structural formula of OLED electron transport materials of the present invention, Figure 1A expressions I, Figure 1B expression II；；
Fig. 2 is the synthetic route chart of OLED electron transport materials of the present invention；
Fig. 3 is the synthetic route chart of compound A in the prior art.
Embodiment
The present invention provides Organic Electron Transport Material and its preparation method and application, to make the purpose of the present invention, technical side Case and effect are clearer, clear and definite, and the present invention is described in more detail below.It is it should be appreciated that described herein specific real Example is applied only to explain the present invention, is not intended to limit the present invention.
BTBT ([1] benzothieno [3,2-b] [1] benzothiophene) is that one kind is widely used in organic photoelectric The molecule parent nucleus in field, especially in p-type organic semiconductor field, the small molecule organic semiconductor material prepared based on the parent nucleus Hole mobility can reach 10cm2/V-1m-1, this is significantly larger than the hole mobility of anthracene (anthracene), this is because BTBT has very flat molecular structure and extremely close intermolecular stacking.Meanwhile the triplet of BTBT is much Higher than anthracene.
Nitrogenous aromatic heterocycle, such as pyridine (Py) group, are proved effectively to strengthen the electron injection ability of ETM simultaneously Therefore relatively low startup voltage is obtained, this is because the nitrogen-atoms with lone electron pair can be had an effect with metal in pyridine. Meanwhile the electron attraction of pyridine in itself can drag down the lumo energy of material so that electron injection is more easy.
A kind of Organic Electron Transport Material provided by the present invention, its molecular structural formula (Fig. 1) are as follows：
Wherein, Ar gene expressions are the aromatic heterocycle with electron performance or electron-withdrawing energy, can be but be not limited to Phenyl, naphthyl, anthryl, thienyl, bithiophene base, pyridine radicals, pyrimidine radicals, quinolyl, isoquinolyl, indyl, isoindolyl, Thiazolyl, oxazolyl, benzothiazolyl, diazosulfide base, naphthyridines base, pyridazinyl, pyrimidine radicals, pyrazinyl etc..Meanwhile Ar bases At least one in group is nitrogenous aromatic heterocycle.
Meanwhile Ar groups can be that the electron withdrawing groups such as above-mentioned group is substituted by fluorine, trifluoromethyl substitutes, cyano group substitutes take The derivative in generation.
The present invention [1] benzothieno [3,2-b] [1] benzothiophene that introduces innovative first is used as electricity The parent nucleus of sub- transmission material, the parent nucleus have excellent flatness, crystallinity and carrier transmission performance.By introducing both ends Nitrogenous aromatic heterocycle electrophilic end-capping group, reduces the lumo energy of system, so as to improve the electronic transmission performance of material.Together When, BTBT brings material higher triplet as parent nucleus, is conducive to improve the stability of device.
As described above, the compound structure in Formulas I is as follows, but it is not limited to enumerated structure：
As described above, the compound structure in Formula II is as follows, but it is not limited to enumerated structure：
The synthetic route chart (Fig. 2) of the Organic Electron Transport Material of the present invention is as follows：
First, compound A (Fig. 3) is prepared in method according to the literature, comprises the following steps that：
1 prepare compound 1 of embodiment
Comprise the following steps that：
In 100mL pressure bottles, compound A 2g (5mmol), 2- pyridine boronic acids 2.69g (20mmol), carbon are sequentially added Sour potassium 2.8g (20mmol), tetra-triphenylphosphine palladium 0.25g, ethanol 5mL, toluene 15mL, water 5mL, cover after nitrogen bubbling 15min Lid, reacts 24h at 100 DEG C, filters after being cooled to room temperature and is washed successively with water, methanol, acetone, obtains celadon crude product 1.69g。
By crude product in vacuum sublimation instrument (Shenyang section is sincere, ZDF-5227), distillation parameter be distillation vacuum be 2 × 10-5Pa, three area's temperature of distillation are 280 DEG C, and two area's temperature of distillation are 240 DEG C, and one area's temperature of distillation is 160 DEG C, and established temperature is equal For gradient increased temperature, 50 DEG C, after being increased to target temperature are raised per 15min, insulation distillation 12h, distillation is obtained fine work 1.5g, rises Magnificent yield is 90%.Elemental analysis obtains compound carbon containing 73.18, and hydrogeneous 3.49, nitrogenous 7.08, it is compound 1.
2 prepare compound 2 of embodiment
Comprise the following steps that：
In 100mL pressure bottles, compound A 2g (5mmol), 3- pyridine boronic acids 2.69g (20mmol), carbon are sequentially added Sour potassium 2.8g (20mmol), tetra-triphenylphosphine palladium 0.25g, ethanol 5mL, toluene 15mL, water 5mL, cover after nitrogen bubbling 15min Lid, reacts 24h at 100 DEG C, filters after being cooled to room temperature and is washed successively with water, methanol, acetone, obtains celadon crude product 1.72g。
By crude product in vacuum sublimation instrument (Shenyang section is sincere, ZDF-5227), distillation parameter be distillation vacuum be 2 × 10-5Pa, three area's temperature of distillation are 270 DEG C, and two area's temperature of distillation are 230 DEG C, and one area's temperature of distillation is 160 DEG C, and established temperature is equal For gradient increased temperature, 50 DEG C, after being increased to target temperature are raised per 15min, insulation distillation 12h, distillation is obtained fine work 1.39, rises Magnificent yield is 88%.Elemental analysis obtains compound carbon containing 73.18, and hydrogeneous 3.49, nitrogenous 7.08, it is compound 2.
3 prepare compound 15 of embodiment
Comprise the following steps that：
In 100mL pressure bottles, compound A 2g (5mmol), 3- quinoline boronic acids 2.69g (20mmol), carbon are sequentially added Sour potassium 2.8g (20mmol), tetra-triphenylphosphine palladium 0.25g, ethanol 5mL, toluene 15mL, water 5mL, cover after nitrogen bubbling 15min Lid, reacts 24h at 100 DEG C, filters after being cooled to room temperature and is washed successively with water, methanol, acetone, obtains celadon crude product 1.79。
By crude product in vacuum sublimation instrument (Shenyang section is sincere, ZDF-5227), distillation parameter be distillation vacuum be 2 × 10-5Pa, three area's temperature of distillation are 290 DEG C, and two area's temperature of distillation are 250 DEG C, and one area's temperature of distillation is 180 DEG C, and established temperature is equal For gradient increased temperature, 50 DEG C, after being increased to target temperature are raised per 15min, insulation distillation 12h, distillation is obtained fine work 1.59, rises Magnificent yield is 91%.Elemental analysis obtains compound carbon containing 77.70, and hydrogeneous 3.67, nitrogenous 5.66, it is compound 15.
4 device of embodiment manufactures
The present invention also provides a kind of application of electron transport material as described above, specifically by the electron transport material Applied in organic electroluminescence device.For the electron transport ability of Efficient Characterization material of the present invention, in luminescent device It has chosen using TAPC as hole mobile material, CBP/Ir (ppy)3As luminescent material, hole barrier material is used as using TmPyPB Material, using commercialized LG-201 as reference electron transport material, electron injection material is used as using LiF.Device architecture is： ITO/MoO3(1nm)/TAPC(40nm)/CBP：Ir(ppy)3(20nm)/TmPyPB(20nm)/ETM(40nm)/LiF(1nm)/ Al。
Device manufacture process is specific as follows：
The glass substrate for being coated with transparent conductive layer is ultrasonically treated in acetone, is rinsed in deionized water, third Ketone：Ultrasonic oil removing, is baked under clean environment and removes moisture completely, use ultraviolet light in alcohol mixed solvent (volume ratio 1: 1) And ozone clean, and with low energy positive electricity beamlet bombarded surface；The above-mentioned glass substrate with anode layer is placed in vacuum chamber, is taken out Vacuum is to 9*10-5Pa。
The vacuum evaporation MoO on above-mentioned anode tunic3As hole injection layer, evaporation rate 0.05nm/s, evaporation film Thickness is 1nm；TAPC is deposited on hole injection layer is as hole transmission layer, evaporation rate 0.05nm/s, evaporation thickness 40nm；Vacuum evaporation is as CBP on hole transmission layer：Ir(ppy)3Device luminescent layer, evaporation rate 0.05nm/s, steams Plating total film thickness is 20nm；One layer of TmPyPB of vacuum evaporation is as hole blocking layer, evaporation rate 0.05nm/ on luminescent layer S, evaporation total film thickness are 20nm；The electric transmission of a stratification compound 1 or LG-201 as device is deposited on hole blocking layer Layer, its evaporation rate is 0.05nm/s, and evaporation total film thickness is 40nm；Vacuum evaporation LiF is device on electron transfer layer (ETL) Electron injecting layer, its evaporation rate is 0.05nm/s, film thickness 1nm；Finally on LiF evaporation metal aluminium as device Cathode, film thickness 150nm.
Device performance such as following table：
It should be appreciated that the application of the present invention is not limited to above-mentioned citing, for those of ordinary skills, can To be improved or converted according to the above description, all these modifications and variations should all belong to the guarantor of appended claims of the present invention Protect scope.

Claims (8)

1. a kind of OLED electron transport materials, it is characterised in that its molecular structural formula is as follows：
Wherein, Ar1、Ar2、Ar1′、Ar2' it is Ar groups, the Ar groups are the fragrance with electron performance or electron-withdrawing energy Heterocycle, and at least one in the Ar groups of every kind of molecular structural formula is nitrogenous aromatic heterocycle.
2. OLED electron transport materials according to claim 1, it is characterised in that the Ar groups include phenyl, naphthyl, Anthryl, thienyl, bithiophene base, pyridine radicals, pyrimidine radicals, quinolyl, isoquinolyl, indyl, isoindolyl, thiazolyl, evil Oxazolyl, benzothiazolyl, diazosulfide base, naphthyridines base, pyridazinyl, pyrimidine radicals, pyrazinyl.
3. OLED electron transport materials according to claim 1, it is characterised in that
In any one.
4. OLED electron transport materials according to claim 3, it is characterised in that Ar1、Ar2、Ar1′、Ar2' it is above-mentioned base The derivative that group is substituted with electron withdrawing groups.
5. OLED electron transport materials according to claim 4, it is characterised in that the electron withdrawing group for it is fluorine-based, three Any one in methyl fluoride, cyano group.
6. a kind of preparation method of OLED electron transport materials, it is characterised in that utilize compound A and electrophilic heterocyclic boronic acids ester Suzuki couplings occur for B or C so as to obtain corresponding electron transport material, one kind during reaction equation is following：
Wherein, Ar1、Ar2、Ar1′、Ar2' it is Ar groups, the Ar groups are the fragrance with electron performance or electron-withdrawing energy Heterocycle, and at least one in the Ar groups of every kind of molecular structural formula is nitrogenous aromatic heterocycle.
A kind of 7. application of OLED electron transport materials, it is characterised in that in organic electroluminescence device, at least one work( Ergosphere contains the OLED electron transport materials described in the claims 1-6.
8. a kind of organic electroluminescence device, it is characterised in that anode layer and cathode layer including forming a pair of electrodes, Yi Ji Luminescent layer and electron transfer layer between anode layer and cathode layer, the electron transfer layer contain institute in the claims 1-6 The OLED electron transport materials stated.
CN201711171797.1A 2017-11-22 2017-11-22 A kind of OLED electron transport layer materials and its preparation method and application Pending CN107936038A (en)

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Cited By (5)

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CN110734452A (en) * 2018-07-18 2020-01-31 北京大学深圳研究生院 semiconductor materials, and preparation method and application thereof
CN110734451A (en) * 2018-07-18 2020-01-31 北京大学深圳研究生院 semiconductor materials, preparation method thereof and organic light emitting diode
CN113087720A (en) * 2021-03-03 2021-07-09 北京大学深圳研究生院 N-type organic semiconductor material based on benzothieno [3,2-b ] benzothiophene and preparation method and application thereof
CN115151552A (en) * 2020-02-28 2022-10-04 日本化药株式会社 Condensed polycyclic aromatic compound
WO2024060203A1 (en) * 2022-09-23 2024-03-28 北京大学深圳研究生院 Organic hole injection material and use

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WO2024060203A1 (en) * 2022-09-23 2024-03-28 北京大学深圳研究生院 Organic hole injection material and use

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