CN108899434A - It is a kind of containing connection fused heterocyclic compound organic electro-optic device and its application - Google Patents

It is a kind of containing connection fused heterocyclic compound organic electro-optic device and its application Download PDF

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CN108899434A
CN108899434A CN201810959100.5A CN201810959100A CN108899434A CN 108899434 A CN108899434 A CN 108899434A CN 201810959100 A CN201810959100 A CN 201810959100A CN 108899434 A CN108899434 A CN 108899434A
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organic
optic device
layer
fused heterocyclic
phenyl
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王子兴
吴跃初
赵晓宇
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Zhejiang Hua Hui Photoelectric Technology Co Ltd
YURUI (SHANGHAI) CHEMICAL Co Ltd
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Zhejiang Hua Hui Photoelectric Technology Co Ltd
YURUI (SHANGHAI) CHEMICAL Co Ltd
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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Abstract

The present invention provides a kind of organic electro-optic device of fused heterocyclic compound containing connection and its application, which includes organic electroluminescence device (OLED), organic field effect tube (OFET), organic solar batteries etc..Contain connection fused heterocyclic compound in hole injection layer, hole transmission layer, electronic barrier layer or luminescent layer especially in organic electroluminescence device (OLED).Since connection fused heterocyclic compound has and anode level-density parameter is good, glass transition temperature is high, with fairly good heat, photostability, and triplet is to meet exciton confinement requirement, so that organic electroluminescence device (OLED) is with high-efficient, it is low to operate voltage, the advantages of long service life, has a good application prospect.

Description

It is a kind of containing connection fused heterocyclic compound organic electro-optic device and its application
Technical field
The invention belongs to organic photoelectric technical field more particularly to a kind of organic electro-optic devices of the fused heterocyclic compound containing connection And its application.
Background technique
Since the mankind enter the informationized society of 21 century, display device is played the part of as the essential interface of human-computer interaction Drill vital role.Information display device develops to cathode-ray tube from simplest switch light bulb indicator light (CRT) display, until the liquid crystal (LCD) of today, plasma (PDP), Flied emission (FED) display.However, as the mankind see The raising of reward demand and visual enjoyment, existing display technology are unable to satisfy people to display equipment increasingly higher demands, seek Modern, more efficient luminescent material, processability is higher, the lower display device of cost more becomes pursuing a goal for people.
In organic electro-optic device, especially organic electroluminescence device (OLED), organic field effect tube (OFET), have Machine solar battery (OPV) causes the research of numerous scientists and industrial circle.Wherein, OLED or diode are as a new generation Flat panel display progresses into the visual field of people, broad application prospect and it is technical in recent years advance by leaps and bounds so that One of the research that OLED is most popular as plate field of information display and scientific research product development.
The research of electroluminescent organic material starts from the 1960s, until Tang in 1987 etc. makes Organic Electricity for the first time Electroluminescence device, organic luminescent device have been achieved for greatly being in progress.Over nearly 25 years, Organic Light Emitting Diode (OLED) is because of it Have many advantages, such as that self-luminous, wide viewing angle, operating voltage is low, the reaction time is fast, flexible, it has also become flat display field in the world A research hotspot, commercial prod shown up prominently, and shows in plane and lighting area has started certain applications.But The hot spot of the problem of being, while obtaining high efficiency and long-life always OLED research.
OLED luminous mechanism is under DC Electric Field, and electrons and holes are respectively organic after positive and negative polarities injection It is migration in material, compound and decay and generate luminous.The typical structure of OLED include cathode layer, anode layer and be located at this two layers it Between organic function layer, organic function layer may include one or more of electron transfer layer, hole transmission layer and luminescent layer function Ergosphere.
In the preparation and optimization of OLED, the selection of luminescent material is most important, and property is the weight for determining device performance Want one of factor.Common material of main part can be divided into cavity type material of main part, electron-transporting type material of main part, bipolarity main body Material and inertia material of main part.Join fused ring compound due to its efficient thermal stability, group modifiability is strong, and performance can be with It the advantages such as is adjusted by substituent group, while usually there is preferable charge transport ability.It is thick miscellaneous in organic electro-optic device Change compound to be widely used.Indole derivatives such as carbazole compound triplet with higher, excellent hole transport Ability is a kind of material being most widely used in current organic electro-optic device.When indoles or carbazole compound are as organic When photoelectric device hole-transporting layer material, generally require the HOMO energy level of material higher, in favor of hole from anode inject or Person is by hole transport into anode.In OLED device, cavitation material will have higher HOMO energy level, and material is needed to have Certain triplet.Hole injection layer, hole transmission layer and electronic barrier layer are respectively by difference in the OLED device of early period Compound take on, this makes the structure of OLED device become complicated, while preparing mating required for such OLED device Equipment also becomes complicated, it is necessary to which multiple preparation storehouses are affected to the yields of device simultaneously because multilayer makes respectively. If there is a kind of material can be used as hole injection layer, hole transmission layer and electronic barrier layer to use simultaneously, will greatly simplify The manufacturing process of the structure of OLED device and it reduces cost of manufacture.In order to solve the above technical problem, the present invention by oxygen, Thia ring such as benzofuran, benzothiophene introduce the connection fused heterocyclic compound obtained, their planar structure improves material HOMO energy level increases charge transfer efficiency, improves the thermodynamic stability of material.The company replaced simultaneously by special full meta position It connects, its triplet can be made to meet the requirement of exciton confinement, simultaneously because the effect of steric hindrance, is not easy corresponding compound Crystallization.A kind of organic electro-optic device of fused heterocyclic compound containing connection of the invention, especially OLED device will join condensed hetero ring chemical combination Object is applied in hole injection layer, hole transmission layer and electronic barrier layer, can obviously simplify device architecture, increases the effect that shines Rate.
Summary of the invention
In order to solve the problems in the prior art, novel it can be applied to organic light the purpose of the present invention is to provide a kind of Electrical part, the fused heterocyclic compound containing connection in functional layer.The HOMO level-density parameter of these compounds is good, can dramatically increase electricity Lotus efficiency of transmission, material have high thermodynamic stability, and triplet meets the requirement of exciton confinement.The sky of OLED device Cave implanted layer or hole transmission layer or electronic barrier layer or the luminescent layer fused heterocyclic compound containing connection, can obviously simplify device junction The advantages that structure increases luminous efficiency, extends device service life.
To achieve the goals above, the technical solution adopted by the present invention is that：
It is a kind of containing connection fused heterocyclic compound organic electro-optic device described in connection fused heterocyclic compound such as chemical formula (1) institute Show：
Wherein, in chemical formula (1), X is：S, one of O or SiRR；
Ar1, Ar2 substituent group can be identical or different, indicate substituted or unsubstituted aryl, or indicate former containing nitrogen What son, oxygen atom, the substituted or unsubstituted heteroaryl of sulphur atom or silicon atom or substituted or unsubstituted aryl replaced The amido that amido or heteroaryl replace.
It is alkyl, alkoxy, silylation, virtue with 1~36 carbon atom that R, which is selected from one of H, D, F, CN or R, One of race or heteroaromatic ring system, the aromatics or it is heteroaromatic contain nitrogen-atoms, oxygen atom or sulphur atom, independently Selected from one of the following：Substituted or unsubstituted phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alcoxyl Base phenyl, halogenated alkoxy phenyl, cyano-phenyl, silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate Naphthalene, benzothienyl, benzofuranyl, dibenzothiophene, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, Imidazole radicals, phenanthryl, terphenyl, terphenyl support group or fluoranthene base；
N is 0,1,2,3,4 or 5.
Preferably, the Ar1, Ar2 can be independent selected from one of following group：
It is alkyl, alkoxy, silylation, virtue with 1~36 carbon atom that R, which is selected from one of H, D, F, CN or R, One of race or heteroaromatic ring system, the aromatics or it is heteroaromatic contain nitrogen-atoms, oxygen atom or sulphur atom, independently Selected from one of the following：Substituted or unsubstituted phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alcoxyl Base phenyl, halogenated alkoxy phenyl, cyano-phenyl, silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate Naphthalene, benzothienyl, benzofuranyl, dibenzothiophene, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, Imidazole radicals, phenanthryl, terphenyl, terphenyl support group or fluoranthene base；
N is 0,1,2,3,4 or 5；
* it indicates and adjacent atom connected position.
Preferably, the X of the compound is respectively O or S, and Ar1, Ar2 are respectively selected from the substituent group in following table：
In addition, a kind of preparation is also claimed in the present invention, the preparation includes at least one connection condensed hetero ring chemical combination Object and at least one solvent.
A kind of organic electro-optic device is also claimed in the present invention, and the organic electro-optic device includes：
First electrode；
Second electrode, it is facing with the first electrode；
Organic function layer is located between the first electrode and the second electrode；
Wherein, organic function layer includes the connection fused heterocyclic compound or the preparation.
Preferably, the organic electro-optic device includes organic electroluminescence device (OLED), organic field effect tube, has Machine thin film transistor (TFT), organic solar batteries, dye sensitization organic solar batteries, organic optical detector, light-emitting electrochemical Battery or organic laser diode.
Preferably, the organic function layer also contains other organic compounds, metal or metallic compound as dopant.
Preferably, the organic function layer includes hole injection layer, hole transmission layer, electronic barrier layer and luminescent layer.
A kind of application of compound in production organic electro-optic device, the organic electro-optic device is also claimed in the present invention Including organic electroluminescence device, organic field effect tube, Organic Thin Film Transistors, organic solar batteries, dye sensitization Organic solar batteries, organic optical detector, light-emitting electrochemical cell or organic laser diode；Wherein, the compound For above-mentioned connection fused heterocyclic compound.
Compared with prior art, technical effect of the invention is：
Organic electro-optic device of the invention, functional layer include connection fused heterocyclic compound.Especially in OLED device, this hair Bright unique material structure design, such as simultaneously heterocycle introduces, the connection design of full meta position enables material triplet state with higher for oxygen, sulphur Grade, high thermal decomposition temperature and high glass-transition temperature, HOMO energy level and anode matching are more preferable, while having good hole Injection and transmittability.Layer material such as NPB is transmitted with conventional hole, TPD etc. obtains compound as hole compared to the present invention and passes Defeated layer material can effectively promote thermostabilization when organic electronic device operation in use, due to its high glass-transition temperature Property, meet the processing technologys such as the encapsulation of subsequent organic illuminating element.There is these compounds good hole to inject and pass simultaneously Movement Capabilities can be obviously improved the efficiency of organic illuminating element, reduce the operation voltage of element.Due to its high triplet energy level, It can remove from and use TCTA etc. as electronic barrier layer.In application examples, reference organic illuminating element R1 is using NPB as hole transport Layer, TCTA is as electronic barrier layer.Material in the present invention can be injected directly as hole or hole transmission layer, and does not need The other materials such as TCTA simplify the structure of organic illuminating element as electronic barrier layer, while also improving luminous efficiency.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic illuminating element of the present invention；
Fig. 2 is compound OO-A-36 luminescent spectrum figure in the present invention；
Fig. 3 is compound OO-A-49 luminescent spectrum figure in the present invention.
Specific embodiment
In order to make the objectives, technical solutions and advantages of the present invention clearer, below with reference to specific example, to the present invention It is further described.It should be understood that these descriptions are merely illustrative, and it is not intended to limit the scope of the invention.In addition, Below in explanation, descriptions of well-known structures and technologies are omitted, so as not to unnecessarily obscure the concept of the present invention.
Materials synthesis route is as shown below：
The preparation of intermediary material
By the bromo- 2- chlorodiphenyl of O-A-S5 (4g) and 4-, simultaneously furans (3g) is complete in 250ml round-bottomed flask under nitrogen atmosphere It is dissolved in 120ml tetrahydrofuran, adds 2M aqueous sodium carbonate 80ml, then add four-(triphenylphosphine) palladiums again (0.2g), by mixture heating stirring 8 hours.It is cooled to room temperature, removes water layer.Methylene chloride 100ml is added, then is eaten with saturation Salt water 30ml is washed twice.Dichloromethane layer is dry with anhydrous magnesium sulfate, is concentrated in vacuo.Then petroleum ether is used：Dichloro (20:1~1:1) purifies and separates are carried out on a silica gel column as eluent, obtain compound OO-A-S6 (yield 79%).MS (ESI)：534.1(M+H)
It is similar with the synthesis step of OO-A-S6, following intermediary material can be obtained：
OS-A-S6：MS(ESI)：550.1(M+H)
OO-C-S6：MS(ESI)：584.1(M+H)
OO-H-S6：MS(ESI)：610.1(M+H)
OS-H-S6：MS(ESI)：626.1(M+H)
SS-H-S6：MS(ESI)：626.1(M+H)
Embodiment 1:The preparation of compound OO-A-36
S3 (5g) and xenyl aniline (3g) are dissolved completely in dimethylbenzene in 100ml round-bottomed flask under nitrogen atmosphere After in (80ml), sodium tert-butoxide (4g) is added thereto, mixture is heated to reflux 5- by bis- (three-tert-butyl phosphines) palladiums (0.1g) 10 hours.It is cooled to room temperature, is filtered to remove salt, after solvent in vacuo is concentrated, use petroleum ether：Methylene chloride (20:1~2:1) make Purifies and separates are carried out on a silica gel column for eluent, obtain OO-A-36 (yield 74%).HRMS(ESI):743.2684(M+H)
Embodiment 2：The preparation of compound OO-A-49
Compound OO-A-49 preparation step is similar to Example 1.Yield 78%, HRMS (ESI):757.2477(M+H).
Embodiment 3：The preparation of compound OS-A-49
Compound OS-A-49 preparation step is similar to Example 1.Yield 78%, HRMS (ESI):773.2167(M+H).
Embodiment 4：The preparation of compound OO-A-1
It is similar with the preparation step of OO-A-S6, yield 83%, HRMS (ESI):817.2667(M+H).
Embodiment 5：The preparation of compound OO-C-63
It is similar with the preparation step of OO-A-S6, yield 84%, HRMS (ESI):666.2007(M+H).
Embodiment 6：The preparation of compound OO-H-63
It is similar with the preparation step of OO-A-S6, yield 81%, HRMS (ESI):742.2309(M+H).
Embodiment 7：The preparation of compound SS-A-63
It is similar with the preparation step of OO-A-S6, yield 71%, HRMS (ESI):698.1524(M+H).
In the preferred embodiment of the present invention, the organic electro-optic device in the present invention, especially in OLED device The above compound is selected to be used as the hole mobile material in hole transmission layer, hole injection layer or exciton barrier-layer, chemical formula (1) In compound can be used alone, can also will contain in chemical formula (1) in the organic layer of compound comprising one or more p-types Dopant.Currently preferred p-type dopant is with flowering structure：
In in addition preferred a kind of embodiment of the invention, the compound in chemical formula (1) can be separately as OLED The luminescent layer of device, can also be used as dopant and another organic compound forms luminescent layer, more preferably as fluorescence or phosphorus The material of main part of optical compounds, the dopant are preferably one or more phosphorescent dopants, can preferably be selected from iridium (Ir), copper (Cu) or any known and unknown structure of the complex compound of platinum (Pt).
In order to form each layer of organic electro-optic device of the present invention, the methods of vacuum evaporation, sputtering, ion plating can be used, Or water-laid film such as the methods of spin coating, printing, printing, solvent used are not particularly limited.
As shown in Figure 1, organic electro-optic device includes substrate 101, anode 102, hole injection layer 103, hole transmission layer 104, electronic barrier layer 105, luminescent layer or active layer 106, hole blocking layer 107, electron transfer layer 108, electron injecting layer 109, the element that cathode 110 is composed.
The manufacture of OLED device：
P dopant material P-1~P-5 is deposited on the surface for the ito glass that light-emitting area is 2mm × 2mm size or by this p Dopant material steams the hole injection layer (HIL) for forming 5-100nm with compound described in 1%~50% concentration and table altogether, then The hole transmission layer (HTL) of 5-200nm is formed by the compound, then forms 10-100nm's on the hole transport layer Luminescent layer (EML) finally sequentially forms electron transfer layer (ETL) 20-200nm and cathode 50-200nm, if necessary in HTL and Electron injecting layer (EIL) is added between ETL and cathode to manufacture organic hair in EML layers of intermediate addition electronic barrier layer (EBL) Optical element.The OLED is characterized by standard method.
The above specific embodiments are only exemplary, is to preferably make skilled artisans appreciate that originally Patent, be not to be construed as include to this patent range limitation；As long as appointing made by the spirit according to disclosed in this patent How with change or modification, the range that this patent includes is each fallen within.

Claims (10)

1. a kind of organic electro-optic device of the fused heterocyclic compound containing connection, which is characterized in that the connection fused heterocyclic compound is as changed Shown in formula (1)：
Wherein, in chemical formula (1), X is：S, one of O or SiRR；
Ar1, Ar2 substituent group can be identical or different, indicate substituted or unsubstituted aryl, or indicate containing nitrogen-atoms, The substituted or unsubstituted heteroaryl of oxygen atom, sulphur atom or silicon atom, or indicate that substituted or unsubstituted aryl replaces Amido or heteroaryl replace amido.
R is selected from one of H, D, F, CN or R be alkyl with 1~36 carbon atom, alkoxy, silylation, aromatics or One of heteroaromatic ring system, the aromatics or it is heteroaromatic contain nitrogen-atoms, oxygen atom or sulphur atom, be independently selected from One of the following：Substituted or unsubstituted phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxy benzene Base, halogenated alkoxy phenyl, cyano-phenyl, silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, Benzothienyl, benzofuranyl, dibenzothiophene, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, imidazoles Base, phenanthryl, terphenyl, terphenyl support group or fluoranthene base；
N is 0,1,2,3,4 or 5.
2. the organic electro-optic device of the fused heterocyclic compound according to claim 1 containing connection, which is characterized in that the Ar1, Ar2 can be independent selected from one of following group：
R is selected from one of H, D, F, CN or R be alkyl with 1~36 carbon atom, alkoxy, silylation, aromatics or One of heteroaromatic ring system, the aromatics or it is heteroaromatic contain nitrogen-atoms, oxygen atom or sulphur atom, be independently selected from One of the following：Substituted or unsubstituted phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxy benzene Base, halogenated alkoxy phenyl, cyano-phenyl, silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, Benzothienyl, benzofuranyl, dibenzothiophene, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, imidazoles Base, phenanthryl, terphenyl, terphenyl support group or fluoranthene base；
N is 0,1,2,3,4 or 5；
* it indicates and adjacent atom connected position.
3. the organic electro-optic device of the fused heterocyclic compound according to claim 1 to 2 containing connection, which is characterized in that the chemical combination The X of object is respectively O or S, and Ar1, Ar2 are respectively selected from the substituent group in following table：
4. a kind of preparation, which is characterized in that the preparation includes at least one described in any item condensed hetero rings of claim 1-3 Compound and at least one solvent.
5. a kind of organic electro-optic device, which is characterized in that the organic electro-optic device includes：
First electrode；
Second electrode, it is facing with the first electrode；
Organic function layer is located between the first electrode and the second electrode；
Wherein, organic function layer includes the system in the described in any item fused heterocyclic compounds of claim 1-3 or claim 4 Agent.
6. organic electro-optic device according to claim 5, which is characterized in that the organic electro-optic device includes organic electroluminescence Luminescent device (OLED), organic field effect tube, Organic Thin Film Transistors, organic solar batteries, dye sensitization are organic too Positive energy battery, organic optical detector, light-emitting electrochemical cell or organic laser diode.
7. organic electro-optic device according to claim 6, which is characterized in that it is organic that the organic function layer also contains other Compound, metal or metallic compound are as dopant.
8. according to the described in any item organic electro-optic devices of claim 5-7, which is characterized in that the organic function layer includes sky Cave implanted layer, hole transmission layer, electronic barrier layer and luminescent layer.
9. a kind of application of compound in production organic electro-optic device, which is characterized in that the organic electro-optic device includes Organic electroluminescence devices, organic field effect tube, Organic Thin Film Transistors, organic solar batteries, dye sensitization are organic too Positive energy battery, organic optical detector, light-emitting electrochemical cell or organic laser diode；Wherein, the compound is right It is required that the described in any item fused heterocyclic compounds of 1-3.
10. application according to claim 9, which is characterized in that the organic electro-optic device includes：
First electrode；
Second electrode, it is facing with the first electrode；
Wherein, organic function layer includes and makes described in the described in any item fused heterocyclic compounds of claim 1-3 or claim 4 Agent；
Hole injection layer, hole transmission layer, electronic barrier layer and the luminescent layer that the organic function layer includes.
CN201810959100.5A 2018-08-22 2018-08-22 It is a kind of containing connection fused heterocyclic compound organic electro-optic device and its application Pending CN108899434A (en)

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CN103249722A (en) * 2010-10-13 2013-08-14 罗门哈斯电子材料韩国有限公司 Novel compounds for organic electronic material and organic electroluminescent device using the same
CN107033167A (en) * 2017-05-22 2017-08-11 上海大学 With the cuprous ion complex of thermal activation delayed fluorescence and its preparation and application
CN108203427A (en) * 2016-12-19 2018-06-26 江苏三月光电科技有限公司 It is a kind of using carbazole as the compound of core and its application on organic electroluminescence device

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103249722A (en) * 2010-10-13 2013-08-14 罗门哈斯电子材料韩国有限公司 Novel compounds for organic electronic material and organic electroluminescent device using the same
CN108203427A (en) * 2016-12-19 2018-06-26 江苏三月光电科技有限公司 It is a kind of using carbazole as the compound of core and its application on organic electroluminescence device
CN107033167A (en) * 2017-05-22 2017-08-11 上海大学 With the cuprous ion complex of thermal activation delayed fluorescence and its preparation and application

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