CN108948028A - A kind of organic electro-optic device of oxygen-containing thia ring triarylamine compounds and its application - Google Patents
A kind of organic electro-optic device of oxygen-containing thia ring triarylamine compounds and its application Download PDFInfo
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Abstract
The present invention provides a kind of organic electro-optic device of oxygen-containing thia ring triarylamine compounds and its application, which includes organic electroluminescence device (OLED), organic field effect tube (OFET), organic solar batteries etc..Contain oxygen-containing thia ring triarylamine compounds in hole injection layer, hole transmission layer, electronic barrier layer or luminescent layer especially in organic electroluminescence device (OLED).Since oxygen-containing thia ring triarylamine compounds have, 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
Technical field
The invention belongs to organic photoelectric technical field more particularly to a kind of organic light of oxygen-containing thia ring triarylamine compounds
Electrical part 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.
Containing triarylamine compounds have and the matched energy level of anode, excellent cavity transmission ability is current organic photoelectric
A kind of material being most widely used in device.When triarylamine compounds are as organic electro-optic device hole-transporting layer material
When, require the HOMO energy level of material higher, generally so that hole is injected from anode or by hole transport into anode.?
In OLED device, cavitation material will have higher HOMO energy level, and material is needed to have certain triplet.Early period
Hole injection layer, hole transmission layer and electronic barrier layer are taken on by different compounds respectively in OLED device, this makes OLED
The structure of device becomes complicated, while preparing and mating required for such OLED device also become complicated, it is necessary to multiple systems
Standby storehouse is affected to the yields of device simultaneously because multilayer makes respectively.If there is a kind of material can be simultaneously as sky
Cave implanted layer, hole transmission layer and electronic barrier layer use, and will greatly simplify the structure of OLED device and its manufacturing process, drop
Low cost of manufacture.In order to solve the above technical problem, the present invention is obtained by such as benzofuran, the benzothiophene introducing of oxygen, thia ring
The oxygen thia ring triarylamine compounds obtained, their planar structure improve the HOMO energy level of material, increase charge transfer efficiency,
Improve the thermodynamic stability of material.The connection replaced simultaneously by meta position guarantees that its triplet meets wanting for exciton confinement
It asks.A kind of organic electro-optic device of oxygen-containing thia ring triarylamine compounds of the invention, especially OLED device oxygen thia ring three
Aromatic amine compound is applied in hole injection layer, hole transmission layer and electronic barrier layer, can obviously simplify device architecture, increases
Luminous efficiency.
Summary of the invention
In order to solve the problems in the prior art, the purpose of the present invention is to provide a kind of oxygen-containing thia ring triaryl amine chemical combination
The organic electro-optic device of object includes oxygen-containing thia ring triarylamine compounds in organic function layer.The HOMO of these compounds
Level-density parameter is good, dramatically increases charge transfer efficiency, and material has high thermodynamic stability, and triplet meets exciton
The requirement of constraint.The oxygen-containing thia ring three of the hole injection layer or hole transmission layer or electronic barrier layer or luminescent layer of OLED device
The advantages that aromatic amine compound can obviously simplify device architecture, increase luminous efficiency, extend device service life.
A kind of organic electro-optic device of oxygen-containing thia ring triarylamine compounds, the organic electro-optic device include:
First electrode；Second electrode, it is facing with the first electrode；Organic function layer is located in the first electrode
Between the second electrode；The organic function layer includes oxygen-containing thia ring triarylamine compounds；The oxygen-containing thia ring
The general structure of triarylamine compounds is as follows:
Wherein, in chemical formula (1) and chemical formula (2), X is one of S or O；Ar1, Ar2 are not take selected from substitution or
One of the aryl in generation, biaryl, fused ring aryl；L is selected from one of following substituent group:
It is alkyl, alkoxy, silylation, virtue with 1~36 C atom that R, which is selected from one of H, D, F, CN or R,
One of race or heteroaromatic ring system；X is one of S or O；N is 0,1,2,3,4 or 5；* it indicates and adjacent atom phase vicinal
It sets.
Preferably, chemical formula (1) is selected from one of chemical formula (3), chemical formula (4), chemical formula (5), chemical formula (2)
For selected from one of chemical formula (6), chemical formula (7), chemical formula (8)
Preferably, the Ar1, Ar2 are selected from one of following substituent group:
Wherein, it is alkyl, alkoxy, silane with 1~36 C atom that R, which is selected from one of H, D, F, CN or R,
One of base, aromatics or heteroaromatic ring system；N is 0,1,2,3,4 or 5；* it indicates and adjacent atom connected position.
Preferably, the aromatics or the heteroaromatic one of the following that independent can be selected from: substituted or unsubstituted phenyl,
Alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxyl phenyl, halogenated alkoxy phenyl, cyano-phenyl, silicon substrate benzene
Base, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, benzothienyl, benzofuranyl, dibenzothiophenes
Base, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, imidazole radicals, phenanthryl, terphenyl, terphenyl support group or fluoranthene
Base.
Preferably, described Ar1, Ar2, L and X take following group respectively:
Application of the oxygen-containing thia ring triarylamine compounds in production organic electro-optic device is also claimed in the present invention, described
Organic electro-optic device includes: first electrode；Second electrode, it is facing with the first electrode；Organic function layer is located in described
Between first electrode and the second electrode；The organic function layer includes oxygen-containing thia ring triarylamine compounds；It is described to contain
The general structure of oxygen thia ring triarylamine compounds is as follows:
Ar1, Ar2 are selected from one of substitution or unsubstituted aryl, biaryl, fused ring aryl；L is selected from following
One of substituent group:
It is alkyl, alkoxy, silylation, virtue with 1~20 C 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 can it is independent be selected from one of the following: replace or do not take
Phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxyl phenyl, halogenated alkoxy phenyl, the cyano benzene in generation
Base, silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, benzothienyl, benzofuranyl, two
Benzothienyl, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, imidazole radicals, phenanthryl, terphenyl, terphenyl support
Base or fluoranthene base；N is 0,1,2,3,4 or 5；* it indicates and adjacent atom connected position；X is one of S or O.
Preferably, the organic electro-optic device includes organic electroluminescence device, organic field effect tube, organic film
Transistor, organic solar batteries, dye sensitization organic solar batteries, organic optical detector, light-emitting electrochemical cell 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, the electronic barrier layer in OLED device
And luminescent layer.
Organic electro-optic device of the invention, functional layer include oxygen thia ring triarylamine compounds.Especially in OLED device
In, unique material structure design of the present invention, such as simultaneously heterocycle introduces, meta position connection design makes material with higher three for oxygen, sulphur
Line state energy level, high thermal decomposition temperature and high glass-transition temperature, HOMO energy level and anode matching are more preferable, while having very well
Hole injection and transmittability.Layer material such as NPB is transmitted with conventional hole, TPD etc. obtains compound conduct compared to the present invention
Hole transport layer material can be promoted effectively when organic electronic device operates in use, due to its high glass-transition temperature
Thermal stability meets the processing technologys such as the encapsulation of subsequent organic illuminating element.These compounds are infused with good hole simultaneously
Enter and transmittability, the efficiency of organic illuminating element can be obviously improved, reduce the operation voltage of element.Due to its high triplet
Energy level can be removed from and use TCTA etc. as electronic barrier layer.In application examples, reference organic illuminating element R1 is using NPB as sky
Cave transport layer, TCTA is as electronic barrier layer.Material in the present invention can be injected directly as hole or hole transmission layer, and
It does not need the other materials such as TCTA and simplifies 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.
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.
The preparation of material
Embodiment 1
Intermediate oxygen heterocycle-boronic acid intermediate O synthesis:
Intermediate O-1 synthesis
1) under nitrogen atmosphere in 250ml round-bottomed flask by dibenzofurans -4- boric acid (S1) (2g) and 2- Nitrobromobenzene
(2g) is dissolved completely in 60ml tetrahydrofuran, adds 2M aqueous sodium carbonate 40ml, then adds four-(triphenylphosphines) again
Palladium (0.2g), by mixture heating stirring 8 hours.It is cooled to room temperature, removes water layer.Be added methylene chloride 100ml, then be saturated
Saline solution 30ml is washed twice.Dichloromethane layer is dry with anhydrous magnesium sulfate, is concentrated in vacuo.Then petroleum ether: acetic acid is used
Ethyl ester (20:1~2:1) carries out purifies and separates as eluent on a silica gel column, obtains S2 (yield 84%)；
2) S2 (6g) and triethyl phosphite (16g) are dissolved completely in neighbour in 250ml round-bottomed flask under nitrogen atmosphere
In dichloro-benzenes (120ml), it is heated to reflux 6-10 hours.Vacuum distillation removes o-dichlorohenzene (70-90ml), and dilute salt is poured into after cooling
In acid, extracted 2 times with methylene chloride 30ml.Dichloromethane layer is dry with anhydrous magnesium sulfate, is concentrated in vacuo.Then dichloro is used
Methane: methanol (20:1~2:1) carries out purifies and separates as eluent on a silica gel column, obtains S3 (yield 70%)；
3) S3 (5g) and iodobenzene (6g) are dissolved completely in dimethylbenzene in 250ml round-bottomed flask under nitrogen atmosphere
After in (120ml), 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, made with petroleum ether: methylene chloride (20:1~2:1)
Purifies and separates are carried out on a silica gel column for eluent, obtain S4 (yield 82%)；
4) S3 (6g) is dissolved completely in anhydrous tetrahydro furan (120ml) in 250ml round-bottomed flask under nitrogen atmosphere,
- 40 degree or less are cooled to liquid nitrogen/alcohol mixture.N-BuLi-the hexane solution of 2 times of equivalents is added, lower than -40 degree
It reacts 2 hours below.It is cooled to -78 degree again hereinafter, the trimethylborate of 3 times of equivalents is added, after the reaction was continued 1 hour, heats up
To room temperature reaction 6-12 hours.After reaction, 0 degree is cooled to hereinafter, carefully with saturated aqueous ammonium chloride quenching reaction, and
With room temperature reaction 2-6 hours.It isolates dry with anhydrous magnesium sulfate after organic layer, is concentrated to dryness, with methylene chloride: methanol (20:
1~1:1) it is used as eluent to carry out purifies and separates on a silica gel column, obtain O-1 (yield 73%)；
By the iodobenzene in step 3), 1- iodine naphthalene, 2- iodine naphthalene, 2- phenyl iodobenzene, 3- phenyl iodobenzene or 4- phenyl iodobenzene are changed into
Etc. can be obtained serial oxygen heterocycle-boronic acid intermediate.
The synthesis of intermediate S-1
By intermediate O-1 synthesis step 1) in dibenzofurans -4- boric acid change dibenzothiophenes -4- boric acid into, through 1) -
It 4), can be with after implementing
It obtains S-1 (yield 65%).
Compound 3-1 to 8-100 can be synthesized by the following to obtain by selecting different intermediate:
Embodiment 2: the preparation of compound 3-1
Two fluorenes -2- boric acid (6.8g) of spiral shell and MO-1 (10g) are dissolved completely in 250ml round-bottomed flask under nitrogen atmosphere
In 120ml toluene/tetrahydrofuran (1:1), 2M aqueous sodium carbonate 80ml is added, then adds four-(triphenylphosphine) palladiums again
(0.2g), by mixture heating stirring 8 hours.It is cooled to room temperature, removes water layer.Methylene chloride 200ml 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: dichloro is used
(20:1~1:1) carries out purifies and separates as eluent on a silica gel column, obtains compound 12.3g, (yield 75.8%).It measures
MS (ESI): 815.2
Embodiment 3: the preparation of compound 3-11
By shown in embodiment 1, after MO-1 is replaced with MO-2, compound 3-11 is obtained, yield 70.2% is separated, measures MS
(ESI):891.3。
Embodiment 4: the preparation of compound 3-21
By shown in embodiment 1, it after MO-1 is replaced with MO-3, can get compound 3-21, separate yield 73.6%, measure
MS(ESI):891.4。
Embodiment 5: the preparation of compound 5-11
By step shown in embodiment 1, two fluorenes -4- boric acid of spiral shell reacts to obtain compound 5-11 with intermediate MO-2, and separation produces
Rate 66.8%.It measures MS (ESI): 891.2.Embodiment 6: the preparation of compound 5-12
By step shown in embodiment 1, two fluorenes -4- boric acid of spiral shell reacts to obtain compound 5-12 with intermediate MO-4, and separation produces
Rate 56%.It surveys
It obtains MS (ESI): 907.2.
Embodiment 7: the preparation of compound 6-11
By step shown in embodiment 1, intermediate O-1 is reacted to obtain compound 6-11 with intermediate M-1, separates yield
68%.It measures MS (ESI): 891.3.Embodiment 8: the preparation of compound 6-12
By step shown in embodiment 1, intermediate S-1 is reacted to obtain compound 6-11 with intermediate M-1, separates yield
63.5%.It measures MS (ESI): 907.4.
Embodiment 9: the preparation of compound 8-11
By step shown in embodiment 1, intermediate O-1 is reacted to obtain compound 8-11 with intermediate M-2, separates yield
78%.It measures MS (ESI): 891.3.
Embodiment 10: the preparation of compound 8-12
By step shown in embodiment 1, intermediate S-1 is reacted to obtain compound 8-12 with intermediate M-2, separates yield
69%.It measures MS (ESI): 907.4.
Embodiment 11
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)
Or the compound in chemical formula (2) can be used alone, can also will contain compound in chemical formula (1) or chemical formula (2) has
It include one or more p-type dopants in machine layer.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) or chemical formula (2) can be single
The solely luminescent layer as OLED device, can also be used as dopant and another organic compound forms luminescent layer, more preferably make
For fluorescence or the material of main part of phosphorescent compound, the dopant is preferably one or more phosphorescent dopants, can preferably be selected from
Any known and unknown structure of the complex compound of iridium (Ir), copper (Cu) or 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
With cathode 110.
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 oxygen-containing thia ring triarylamine compounds, which is characterized in that the organic electro-optic device packet
It includes:
First electrode；Second electrode, it is facing with the first electrode；Organic function layer is located in the first electrode and institute
It states between second electrode；The organic function layer includes oxygen-containing thia ring triarylamine compounds；Three virtue of oxygen-containing thia ring
The general structure of amine compounds is as follows:
Ar1, Ar2 are selected from one of substitution or unsubstituted aryl, biaryl, fused ring aryl；L is selected from following substitution
One of base:
R is selected from one of H, D, F, CN or R be alkyl with 1~36 C atom, alkoxy, silylation, aromatics or
One of heteroaromatic ring system, the aromatics or it is heteroaromatic can it is independent be selected from one of the following: it is substituted or unsubstituted
Phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxyl phenyl, halogenated alkoxy phenyl, cyano-phenyl,
Silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, benzothienyl, benzofuranyl, hexichol
Bithiophene base, 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；X is one of S or O.
2. the organic electro-optic device of oxygen-containing thia ring triarylamine compounds according to claim 1, which is characterized in that chemistry
Formula (1) is selected from one of chemical formula (3), chemical formula (4), chemical formula (5), and chemical formula (2) is selected from chemical formula (6), changes
One of formula (7), chemical formula (8):
。
3. the organic electro-optic device of oxygen-containing thia ring triarylamine compounds according to claim 1, which is characterized in that described
Ar1, Ar2 are selected from one of following substituent group:
Wherein, it is alkyl, alkoxy, silylation, virtue with 1~36 C 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 can it is independent be selected from one of the following: replace or do not take
Phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxyl phenyl, halogenated alkoxy phenyl, the cyano benzene in generation
Base, silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, benzothienyl, benzofuranyl, two
Benzothienyl, aryl thiazole base, dibenzofuran group, fluorenyl, carbazyl, imidazole radicals, phenanthryl, terphenyl, terphenyl support
Base or fluoranthene base；N is 0,1,2,3,4 or 5；* it indicates and adjacent atom connected position.
4. the organic electro-optic device of oxygen-containing thia ring triarylamine compounds according to claim 1, which is characterized in that described
Ar1, Ar2, L and X take following group respectively:
。
5. the organic electro-optic device of oxygen-containing thia ring triarylamine compounds according to claim 1-4, feature
It is, the organic electro-optic device includes organic electroluminescence device (OLED), organic field effect tube, organic thin-film transistor
Pipe, organic solar batteries, dye sensitization organic solar batteries, organic optical detector, light-emitting electrochemical cell or organic
Laser diode.
6. the organic electro-optic device of oxygen-containing thia ring triarylamine compounds according to claim 1-4, feature
It is, the organic function layer also contains other organic compounds, metal or metallic compound as dopant.
7. the organic electro-optic device of oxygen-containing thia ring triarylamine compounds according to claim 1-4, feature
It is, the organic function layer includes hole injection layer, hole transmission layer, electronics resistance in organic electroluminescence device (OLED)
Barrier and luminescent layer.
8. a kind of application of oxygen-containing thia ring triarylamine compounds in production organic electro-optic device, which is characterized in that described to have
Machine photoelectric device includes:
First electrode；Second electrode, it is facing with the first electrode；Organic function layer is located in the first electrode and institute
It states between second electrode；The organic function layer includes oxygen-containing thia ring triarylamine compounds；Three virtue of oxygen-containing thia ring
The general structure of amine compounds is as follows:
Ar1, Ar2 are selected from one of substitution or unsubstituted aryl, biaryl, fused ring aryl；L is selected from following substitution
One of base:
R is selected from one of H, D, F, CN or R be alkyl with 1~20 C atom, alkoxy, silylation, aromatics or
One of heteroaromatic ring system, the aromatics or it is heteroaromatic can it is independent be selected from one of the following: it is substituted or unsubstituted
Phenyl, alkyl phenyl, xenyl, alkyl biphenyl base, halogenophenyl, alkoxyl phenyl, halogenated alkoxy phenyl, cyano-phenyl,
Silicon substrate phenyl, naphthalene, alkyl naphthalene, halogenated naphthalene, cyanonaphthyl, silicon substrate naphthalene, benzothienyl, benzofuranyl, hexichol
Bithiophene base, 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；X is one of S or O.
9. application of the oxygen-containing thia ring triarylamine compounds according to claim 8 in production organic electro-optic device,
It is characterized in that, the organic electro-optic device includes organic electroluminescence device, organic field effect tube, organic thin-film transistor
Pipe, organic solar batteries, dye sensitization organic solar batteries, organic optical detector, light-emitting electrochemical cell or organic
Laser diode.
10. application of the oxygen-containing thia ring triarylamine compounds according to claim 8 in production organic electro-optic device,
It is characterized in that, the organic function layer includes hole injection layer, hole transmission layer, electricity in organic electroluminescence device (OLED)
Sub- barrier layer and luminescent layer.
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| TWI720788B (en) * | 2020-01-20 | 2021-03-01 | 立業精密材料股份有限公司 | Tertiary butyl helical bifluorene ring compound and organic light emitting element |
| CN113135829A (en) * | 2020-01-17 | 2021-07-20 | 浙江华显光电科技有限公司 | Tert-butyl spiral bifluorene ring compound and organic light-emitting element |
| CN113563204A (en) * | 2021-08-30 | 2021-10-29 | 上海钥熠电子科技有限公司 | Triarylamine compound and application thereof in organic electroluminescent display device |
| KR20230036732A (en) * | 2021-09-08 | 2023-03-15 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113135829A (en) * | 2020-01-17 | 2021-07-20 | 浙江华显光电科技有限公司 | Tert-butyl spiral bifluorene ring compound and organic light-emitting element |
| TWI720788B (en) * | 2020-01-20 | 2021-03-01 | 立業精密材料股份有限公司 | Tertiary butyl helical bifluorene ring compound and organic light emitting element |
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| KR102598520B1 (en) * | 2021-09-08 | 2023-11-07 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using same |
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