CN109734607A - A kind of organic compound and its organic electroluminescence device and organic luminescent device - Google Patents
A kind of organic compound and its organic electroluminescence device and organic luminescent device Download PDFInfo
- Publication number
- CN109734607A CN109734607A CN201811439378.6A CN201811439378A CN109734607A CN 109734607 A CN109734607 A CN 109734607A CN 201811439378 A CN201811439378 A CN 201811439378A CN 109734607 A CN109734607 A CN 109734607A
- Authority
- CN
- China
- Prior art keywords
- organic
- layer
- unsubstituted
- substituted
- organic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of organic compound and its organic electroluminescence device and organic luminescent device.Belong to organic photoelectrical material technical field.A kind of organic compound provided by the invention, general formula of molecular structure is as shown in structural formula I:Wherein, Ar1、Ar2、Ar3One of aryl, the heteroaryl of substituted or unsubstituted C3~C30 selected from substituted or unsubstituted C6~C30；L is selected from substituted or unsubstituted fluorenes, dibenzothiophenes, dibenzofurans, carbazole, phenthazine, acridine derivatives；R1One of the aryl of alkyl, substituted or unsubstituted C6~C30 selected from substituted or unsubstituted C1~C15, heteroaryl of substituted or unsubstituted C3~C30.Solve the technical problem for the luminescent properties differences such as organic photoelectrical material luminous efficiency is low in the prior art, driving voltage is higher, service life is short.Compared with prior art, of the invention based on the organic luminescent device containing a kind of organic compound, luminescent properties are obviously improved, and are a kind of excellent OLED materials.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of organic compound and its organic electroluminescence device
Part and organic luminescent device.
Background technique
General organic luminescent device (OLED) is the organic matter layer by being inserted between cathode, anode and cathode and anode
It constitutes, the composition of device is transparent ITO anode, hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EL), sky
The cathodes such as cave barrier layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl are formed, it can omit 1 as needed~
2 organic matter layers.Voltage is formed between two electrodes of device injects hole, electricity from cathode injection electronics another side anode on one side
Son and hole are when luminescent layer is in conjunction with excitation state is formed, and then excitation state returns to stable ground state using energy as releasing
Light.
Luminescent material is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is adulterated in fluorescent host material
The method of doping fluorescent (organic matter including nitrogen) dopant in the method and fluorescent host material of phosphor material (organic metal)
And has the methods of existing long wavelength using dopant (methylene chloride, Rubrene, DCJTB etc.) in illuminator.Mixing in this way
The factors such as miscellaneous improvement emission wavelength, efficiency, driving voltage, service life.Generally forming emitting layer material is with benzene, naphthalene, fluorenes, spiral shell
The ligands such as the centerbodies such as two objects, anthracene, pyrene, carbazole and benzene, biphenyl, naphthalene, heterocycle；And contraposition, meta position, ortho position binding site
Replace structure with amine, cyanogen, fluorine, methyl, tert-butyl etc..
Present oled panel develops to enlargement, needs high performance luminescent material, in addition to launch wavelength chromaticity coordinates it
It is outer to need low driving voltage, high luminous efficiency and the good high glass transition temperature material of thermal stability.
The blue light dopant generally used is the pyrene as patent 10-1192519,10-1358494,10-1333443
1,6 positions (symmetric position of pyrene) link amine series material, can only by 1,6 positions of halide and the response characteristic pyrene of amine
Link same aminate.The present invention be intermediate (Wherein X and Y are different halide) synthesis when it is direct
Generating asymmetric structure and linking same amine is also to ultimately generate dissymmetrical structure.The asymmetric architectural characteristic of invention substance
Guarantee the performances such as thermal stability, dissolubility and film forming and improves luminous efficiency.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence device compound and its use the organic electroluminescence of the compound
Device, the present invention can provide the organic electroluminescence device compound of excellent performance and including the compound by pyrene compound
Organic electroluminescence device and display device including the organic electroluminescence device.
Hereinafter, various embodiments of the present invention be will be described in.It is clear for this specification when describing the present invention
Chu Qijian will omit the explanation to known function or configuration.
As described in this description, " replace " unless otherwise defined, substituent group refers at least one hydrogen in substitution or compound
It is selected from deuterium, halogen radical, hydroxyl, amino, substituted or unsubstituted amido, nitro, substituted or unsubstituted silicon substrate, C1~C30
Alkyl, the silylation of C1~C10, C3~C30 naphthenic base, C6~C30 aryl, the alkoxy of C1~C20, fluorine-based, C1~
The fluoroform alkyl of C10, the trifluoroalkyl of C1~C10 or cyano replace.
In addition, the substituted halogen radical, hydroxyl, amino, substituted or unsubstituted amido, nitro, it is substituted or unsubstituted
Silicon substrate, the alkyl of C1~C30, the silylation of C1~C10, C3~C30 naphthenic base, C6~C30 aryl, C1~C20 alcoxyl
Two adjacent substituent group fusions can in base, fluorine-based, C1~C10 fluoroform alkyl, the trifluoroalkyl of C1~C10 or cyano
To form a ring.
In this specification, " heterocycle " refers to one to three hetero atom that N, O, S and P are selected from a functional group,
Remaining is carbon.
In this specification, " alkyl " refers to aliphatic hydrocarbyl.Alkyl can be the " saturation without any double bond or triple bond
Alkyl ".
Alkyl can be the alkyl of C1~C20.More specifically, alkyl can be the alkyl of C1~C10 or the alkane of C1~C6
Base.For example, the alkyl of C1~C4 means to include 1 to 4 carbon atom and including methyl, ethyl, propyl, different in alkyl chain
It is selected in propyl, normal-butyl, isobutyl group, sec-butyl and tert-butyl.
The alkyl be specific example include methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tert-butyl, amyl,
Hexyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc..
" aryl " refers to the substitution that all elements of cyclic substituents all have p- track and p- track forms conjugation
Base, it includes monocycle, condensed ring or polycyclic functional group.
" heterocyclic aryl " is the hetero atom that 1 to 3 N, O, S and P are selected from aryl, remaining is carbon.When heteroaryl is condensed ring
When, 1 to 4 hetero atom can be contained in each of which ring.
" arlydene " is can to apply the description of above-mentioned aryl other than bilvalent radical.
" inferior heteroaryl " is can to apply the description of above-mentioned heteroaryl other than bilvalent radical.
Working embodiment according to the present invention provides the compound of the organic electronic device of the expression of formula 1.
Technical scheme is as follows, a kind of organic compound structure general formula are as follows:
Wherein, Ar1、Ar2、Ar3Aryl, substituted or unsubstituted C3~C30 selected from substituted or unsubstituted C6~C30
One of heteroaryl；
L is selected from substituted or unsubstituted fluorenes, dibenzothiophenes, dibenzofurans, carbazole, phenthazine, acridine derivatives；
R1The aryl of alkyl, substituted or unsubstituted C6~C30 selected from substituted or unsubstituted C1~C15, replace or
One of the heteroaryl of unsubstituted C3~C30.
The present invention is by connecting aromatic amine compound on L base different location, wherein L base (fluorenes, dibenzothiophenes, dibenzo
Furans, carbazole, phenthazine, acridine derivatives etc.) there is certain electrophilic characteristic, arylamine has certain hole transport energy
Power, the finally obtained fluorene compound that contains is a kind of bipolar materials, has good electronics and cavity transmission ability, can be effective
The electron transport ability of material is improved, improves hole and electronics in the recombination rate of luminescent layer, to improve its organic luminescent device
Luminous efficiency.
Contain asymmetric structure in luminescent material structure, not only there is higher triplet and wider energy gap,
And the glass transition temperature of itself is higher, is not easy to crystallize, and passes through connection fluorenes, dibenzothiophenes, dibenzo furan in molecule
It mutters, the groups such as carbazole, phenthazine, acridine derivatives, increases cavity transmission ability, so that carrier transport balances.
Further, L is selected from following group:
Wherein, R2、R3The virtue of alkyl, substituted or unsubstituted C6~C30 selected from substituted or unsubstituted C1~C15
One of base, heteroaryl of substituted or unsubstituted C3~C30.
Further, the Ar1、Ar2、Ar3Independently selected from following group:
The independent alkyl selected from substituted or unsubstituted C1~C15 of R4, R5, R6, substituted or unsubstituted C6~C30
Aryl, one of the heteroaryl of substituted or unsubstituted C3~C30.
Further, any one of the organic compound in chemical structure as follows:
A kind of organic electroluminescence device using the organic compound, including first electrode, second electrode and be placed in described
One or more organic compound layers between two electrodes, at least one organic compound layer use at least one organic electroluminescence
Device compound.
Further, the organic compound layer includes luminescent layer, hole transmission layer, hole injection layer, electron-transport
The organic electroluminescence device selected in the group of layer, electron injecting layer, hole blocking layer and combinations thereof.
Further, organic electroluminescence device includes organic luminescent device (OLED), organic photovoltaic cell (OSC), Electronic Paper
(e-Paper), Organophotoreceptor (OPC) or Organic Thin Film Transistors (OTFT).
The present invention provides a kind of organic luminescent device, if including anode, cathode and between anode and cathode
Dry organic matter layer, which is characterized in that at least contain organic compound containing described one kind in the organic matter layer.
Preferably, organic matter layer, including luminescent layer, hole transmission layer, hole injection layer, electron transfer layer, electron injection
The organic electroluminescence device selected in the group of layer, hole blocking layer and combinations thereof.
Preferably, the organic electroluminescence device further include organic electro-optic device, organic luminescent device, organic sun device,
The organic electroluminescence device selected in the group of Organophotoreceptor, Electronic Paper and organic memory device and combinations thereof.
Preferably, the display device of organic electroluminescence device is provided.
In the present invention, the organic compound is single or is included in organic matter with other compound mixture forms
In layer.
In the present invention, the organic electroluminescence device preferably includes anode, cathode and between anode and cathode
Several organic matter layers, " organic matter layer " refer to the whole layers disposed between organic electroluminescence device Anodic and cathode
Term.The organic matter layer can be the layer with hole characteristic and the layer with characteristic electron.For example, the organic matter
Layer include hole injection layer, hole transmission layer, both had hole injection but also with the technical ability layer of hole transport, electronic barrier layer,
Luminescent layer, electron transfer layer, electron injecting layer, had both had electron-transport but also with the technical ability of electron injection at hole blocking layer
One or more of layer.
In the present invention, the hole injection layer, hole transmission layer, both had hole injection but also with hole transport
Conventional hole injecting material, hole transporting material can be used in technical ability layer, both had hole injection but also with hole transport
It again include electronics-generation substance other than the substance of technical ability.
For example, it includes luminescent layer that the organic matter layer, which is, the luminescent layer be include phosphorescence host, fluorescent host, phosphorescence
One or more of doping and fluorescence doping.In the present invention, can using the organic electroluminescence device use compound as
Fluorescent host can also be used as fluorescence doping, and adulterate simultaneously as fluorescent host and fluorescence.
In the present invention, the luminescent layer can be red, yellow or blue light-emitting layer.In the present invention, described to shine
When layer is blue light-emitting layer, compound is used to adulterate as blue main body or blue using organic electroluminescence device described above, it can
Obtain high efficiency, high-resolution, high brightness and the organic electroluminescence of long-life device.
In the present invention, the organic matter layer preferably includes electron transfer layer, and the electron transfer layer includes above-mentioned technology
Organic electroluminescence device compound described in scheme.In the present invention, it is also preferable to include metal compounds for the electron transfer layer
Object.
In the present invention, the organic matter layer preferably includes luminescent layer and electron transfer layer, and the luminescent layer and electronics pass
Defeated layer is containing organic electroluminescence device compound described in above-mentioned technical proposal, in the luminescent layer and electron transfer layer
Organic compound can be the same or different.
The present invention does not have special limitation to the preparation method of the organic electroluminescence device, in addition to using the organic of formula (I)
Except electroluminescent device compound, it is prepared into using the preparation method and material of luminescent device well known to those skilled in the art
It arrives.
Organic electroluminescence device of the present invention is organic photovoltaic devices, organic luminescent device (OLED), organic sun electricity
Pond (OSC), Electronic Paper (e-paper), Organophotoreceptor (OPC), Organic Thin Film Transistors (OTFT) and organic memory device
Any one in (Organic Memory Element).
In the present invention, organic electroluminescence device is available with the side such as sputtering, electron beam evaporation, vacuum evaporation
Method evaporation metal or conductive oxide and their alloy on substrate form anode；In the sun being prepared
Hole injection layer, hole transmission layer, luminescent layer, air barrier and electron transfer layer is deposited in pole surface in order, steams again later
Plate the method preparation of cathode.By cathode, organic matter layer, anode sequence vapor deposition production organic electroluminescence on substrate other than above method
Device.The organic matter layer be also may include hole injection layer, hole transmission layer, luminescent layer, hole blocking layer and electronics
The multilayered structures such as transport layer.Organic matter layer is using high molecular material by solvent engineering (spin-coating (spin- in the present invention
Coating), strip forms (tape-casting), scraping blade method (doctor-blading), silk-screen printing (Screen-
Printing), ink jet printing or thermal imaging (Thermal-Imaging) etc.) substitution evaporation coating method preparation, it is possible to reduce device
The number of plies.
Material used in organic electroluminescence device according to the present invention can be divided into top emitting, low transmitting or dual emission.
The compound of organic electroluminescence device according to embodiments of the present invention can be suitable for organic with the similar principle of organic luminescent device
Solar battery, the OLED of illumination, flexibility OLED, Organophotoreceptor, the electroluminescent device aspect such as Organic Thin Film Transistors.
Of the invention is a little: the present invention is used by the organic electroluminescence device that pyrene compound can provide excellent performance
Compound and the organic electroluminescence device including the compound and the display device including the organic electroluminescence device.Solve existing skill
The technical problem for the luminescent properties differences such as organic photoelectrical material luminous efficiency is low in art, driving voltage is higher, service life is short.With
The prior art is compared, and of the invention based on the organic luminescent device containing a kind of organic compound, luminescent properties are obviously improved, and is
A kind of excellent OLED material.
Specific embodiment
In order to be easy to understand the technical means, the creative features, the aims and the efficiencies achieved by the present invention, below
In conjunction with synthetic route and specific embodiment, the present invention is further explained.
The synthetic route of intermediate L is as follows:
1, the synthesis of intermediate L-1
The synthesis of L-1-3:
Add L-1-1, L-1-2, Pd (OAc) in round-bottomed flask under a nitrogen atmosphere2、Bis- diphenylphosphine -9,9- the diformazans of 4,5- Base xanthene, cesium carbonate, flow back 6 hours after toluene solvant.After reaction terminates, separation have it is several layers of, it is logical after being concentrated under reduced pressure
Column is crossed to chromatograph to obtain L-1-3 compound.
The synthesis of L-1-4:
L-1-3 is added in round-bottomed flask under a nitrogen, diisopropyl ether is added, R is slowly added dropwise1MgBr.After dropwise addition, it will mix
Object is closed to stir at 50 DEG C.When the reactions are completed, reaction product is layered, it is to remove water layer, mixture is dense under reduced pressure
Contracting, and obtain compound L -1-4.
The synthesis of L-1-5:
In round-bottomed flask, L-1-4 (0.087mol) and phosphoric acid is added, and mixture is stirred at 60 DEG C.Work as reaction
When completion, water will be added to continue to stir in products therefrom.By being washed after filtering with water and methanol.It is obtained by column chromatography
L-1-5
The synthesis of L-1:
With L-1-3, same method obtains L-1 compound.
2, the synthesis of intermediate L-2
The synthesis of L-2-3:
Add L-2-1, L-2-2, Pd in reaction vessel2(PPh3)4And K2CO3, dissolved with THF and a small amount of water, reflux 24 is small
When.After the reaction was completed, reaction mixture is cooled to room temperature, CH is added2Cl2There are several layers of separation with water, by organic layer MgSO4
It is dry, it is concentrated under reduced pressure, with silica gel column purification, obtains product L-2-3.
The synthesis of L-2:
L-2-3, acetic acid and phosphoric acid are mixed, and mixture is stirred 3 hours at 50 DEG C.It is cooled to room temperature, will be mixed
Object is neutralized with NaOH aqueous solution and is extracted with EA.With magnesium sulfate drying and it is evaporated under reduced pressure.Obtain product L-2.
3, the synthesis of intermediate L-3
The synthesis of L-3-3:
With L-2-3, same method obtains L-3-3 compound.
The synthesis of L-3-4:
By L-3-3 and triphenylphosphine dissolved in o-dichlorohenzene and flow back 24 hours.When after the reaction was completed, passing through decompression
After solvent is distilled off, the product being concentrated by pillar layer separation obtains required L-3-4.
The synthesis of L-3:
L-3-4 and R is added under a nitrogen atmosphere1Halide, NaO (t-Bu), Pd2(dba)3、 P(t-Bu)3, then returning
Flow down stirring 24 hours.It is extracted with methylene chloride and distilled water, and organic layer is subjected to silica gel filtering.Take out organic solution simultaneously
It pours out residue to handle by silica gel column chromatography, obtains required L-3.
4, the synthesis of intermediate L-4
The synthesis of L-4-3:
Add L-4-1, L-4-2, KOH and 1.2L EtOH in reaction vessel under nitrogen flowing, is stirred at room temperature 3 hours.
After the reaction was completed, it is distilled with methylene chloride, organic layer is then subjected to silica gel filtering.Remove organic solvent and with hexane: acetic acid
Ethyl ester is washed to 7:3 (v/v), is carried out column chromatography to product, is obtained L-4-3.
The synthesis of L-4-4:
With L-3-4, same method obtains L-4-4 compound.
The synthesis of L-4:
With L-3, same method obtains L-4 compound.
5, the synthesis of intermediate L-5
The synthesis of L-5-3:
With L-2-3, same method obtains L-5-3 compound.
The synthesis of L-5:
L-5-3 is dissolved in trifluoromethanesulfonic acid and is stirred at room temperature 48 hours.Reaction terminating.Reactant is poured into
The in the mixed solvent of water and pyridine simultaneously flows back 20 minutes.Reaction temperature is cooled to room temperature, CH is used2Cl2It extracts and wipes.With nothing
Water MgSO4A small amount of water is removed, is filtered under diminished pressure, concentration organic solvent uses column chromatography separation product, obtains required L-5.
6, the synthesis of intermediate L-6
The synthesis of L-6-3:
With L-2-3, same method obtains L-6-3 compound.
The synthesis of L-6-4:
L-6-3 is dissolved in methylene chloride, and uses 1M BBr at -78 DEG C3CH2Cl2It is slowly added to after processing.It will mix
It closes object to stir 30 minutes at -78 DEG C, then be stirred at room temperature 24 hours.After the reaction was completed, NaHCO is used3Aqueous solution is quenched
It goes out, is extracted with dichloromethane, organic layer is separated with silica gel, obtains product L-6-4.
The synthesis of L-6:
Potassium carbonate and NMP are added in L-6-4, reacts 12 hours, is extracted with methylene chloride and distilled water, it will
Organic layer is separated into silica gel.Residue is separated by silica gel, obtains product L-6 (C).
Wherein, X, Y are selected from one of F, Cl, Br, I；
R1、R2It is independent selected from hydrogen atom, the alkyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C6~
One of the aryl of C30, heteroaryl of substituted or unsubstituted C6~C30.
Embodiment 1: the preparation of compound 8
Step1. L1 (23.09g, 75mmol) sodium tert-butoxide (21.62g, 225mmol) is added in three-necked flask, is added
Enter the displacement of toluene (500mL) nitrogen twice, A1 (26.21g, 75mmol) and catalyst Pd is added2(dba)3(2.06g,
2.25mmol), N2Displacement three times, is injected tri-tert-butylphosphine (0.36mL, 15mmol), is warming up to 110 DEG C, reacts 1h.Reaction solution
Cooling, washing crosses diatomite and removes palladium catalyst, be evaporated, recrystallized with methylene chloride/petroleum ether, obtain yellow solid, then use
45 DEG C of toluene/ethyl acetate mixed solvent are washed 2h, are filtered, are obtained B1 (36.73g, 85%).The compound of generation is by using LC-MS
It determines.Experiment value m/z:393.13 (theoretical value 393.92)
Step2. B1 (43.21g, 75mmol) sodium tert-butoxide (21.62g, 225mmol) is added in three-necked flask, is added
Enter the displacement of toluene (500mL) nitrogen twice, A1 (26.21g, 75mmol) and catalyst Pd is added2(dba)3(2.06g,
2.25mmol), N2Displacement three times, is injected tri-tert-butylphosphine (0.36mL, 15mmol), is warming up to 110 DEG C, reacts 1h.Reaction solution
Cooling, washing crosses diatomite and removes palladium catalyst, be evaporated, recrystallized with methylene chloride/petroleum ether, obtain yellow solid, then use
45 DEG C of toluene/ethyl acetate mixed solvent are washed 2h, are filtered, are obtained 8 (53.31g, 80%).The compound of generation is by using LC-MS
It determines.Mass spectrum m/z, theoretical value: 889.17；Measured value: 888.45.Theoretical elemental content (%) C67H56N2: C, 90.50；H,
6.35；N,3.15.The above results confirm that obtaining product is target product.
Embodiment 2: the preparation of compound 23
By the synthetic method in embodiment 1, compound 23 is obtained.Mass spectrum m/z, theoretical value: 878.37；Measured value:
879.16.Theoretical elemental content (%) C64H50N2S:C, 87.43；H, 5.73；N,3.19；S,3.65.The above results confirmation obtains
Obtaining product is target product.
Embodiment 3: the preparation of compound 26
By the synthetic method in embodiment 1, compound 26 is obtained.Mass spectrum m/z, theoretical value: 890.16；Measured value:
889.44 theoretical elemental content (%) C66H55N3:C, 89.05；H,6.23；N, 4.72.The above results confirm that obtaining product is
Target product.
Embodiment 4: the preparation of compound 44
By the synthetic method in embodiment 1, compound 44 is obtained.Mass spectrum m/z, theoretical value: 863.09；Measured value:
862.39.Theoretical elemental content (%) C64H50N2O:C, 89.06；H, 5.84；N,3.25；O,1.85.The above results confirmation obtains
Obtaining product is target product.
Embodiment 5: the preparation of compound 64
By the synthetic method in embodiment 1, compound 64 is obtained.Mass spectrum m/z, theoretical value: 718.90；Measured value:
718.24.Theoretical elemental content (%) C52H34N2S:C, 86.88；H, 4.77；N,3.90；S,4.46.The above results confirmation obtains
Obtaining product is target product.
Embodiment 6: the preparation of compound 77
By the synthetic method in embodiment 1, compound 77 is obtained.Mass spectrum m/z, theoretical value: 778.98；Measured value:
778.33.Theoretical elemental content (%) C59H42N2:C, 90.97；H,5.43；N,3.60.The above results confirm that obtaining product is
Target product.
Embodiment 7: the preparation of compound 118
By the synthetic method in embodiment 1, compound 118 is obtained.Mass spectrum m/z, theoretical value: 702.84 measured values:
702.27 theoretical elemental content (%) C52H34N2O:C, 88.86；H,4.88；N, 3.99；O,2.28.The above results confirmation obtains
Obtaining product is target product.
<experimental example>
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic wave
Washing 30 minutes, then cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleans, using isopropyl
Alcohol, acetone, methanol solvate carry out drying after ultrasonic washing in order, and the substrate after drying is transferred to plasma clean
In machine, aforesaid substrate washing is sent in evaporator after five minutes.
Hole injection layer 2-TNATA evaporation thickness is successively deposited on cleaned ito transparent electrode is
Hole transmission layer a-NPD evaporation thickness isBD1~the BD3 or this hair of ADN (9,10- bis- (2- naphthalene) anthracene) and 5%
A kind of bright organic compound evaporation thickness isHole blocking layer and electron transfer layer TPBi evaporation thickness areLiF evaporation thickness isIt is with Al evaporation thicknessForm cathode；Above process organic matter vaporization plating speed
Degree is keptThe evaporation rate of LiF is notThe evaporation rate of Al is not
Table 1 is the performance test results for the organic luminescent device that the embodiment of the present invention and comparative example are prepared.
[table 1]
From above-mentioned 1 result of table, organic electroluminescence device is prepared with compound using organic electroluminescence device provided by the invention
Part, the luminous efficiency and life characteristic of organic electroluminescence device significantly improve.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, various changes and improvements may be made to the invention without departing from the spirit and scope of the present invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent defines.
Claims (10)
1. a kind of organic compound, which is characterized in that its general formula of molecular structure is as shown in structural formula I:
Wherein, Ar1、Ar2、Ar3Aryl, substituted or unsubstituted C3~C30 selected from substituted or unsubstituted C6~C30 it is miscellaneous
One of aryl；
L is selected from substituted or unsubstituted fluorenes, dibenzothiophenes, dibenzofurans, carbazole, phenthazine, acridine derivatives；
R1It is the aryl of alkyl, substituted or unsubstituted C6~C30 selected from substituted or unsubstituted C1~C15, substituted or unsubstituted
One of the heteroaryl of C3~C30.
2. organic compound according to claim 1, which is characterized in that L is selected from following group:
Wherein, R2、R3The aryl of alkyl, substituted or unsubstituted C6~C30 selected from substituted or unsubstituted C1~C15 replaces
Or one of heteroaryl of unsubstituted C3~C30.
3. organic compound according to claim 1, it is characterised in that: the Ar1、Ar2、Ar3Independently selected from following base
Group:
The virtue of the independent alkyl selected from substituted or unsubstituted C1~C15 of R4, R5, R6, substituted or unsubstituted C6~C30
One of base, heteroaryl of substituted or unsubstituted C3~C30.
4. organic compound according to claim 1 to 3, which is characterized in that the organic compound is selected from such as
Descend any one in shown chemical structure:
5. a kind of organic electroluminescence device using organic compound described in claim 1-4 any one, including first electrode,
Two electrodes and the one or more organic compound layers being placed between two electrode, it is characterised in that: at least one organises
It closes nitride layer and uses at least one organic compound.
6. organic electroluminescence device according to claim 5, it is characterised in that: the organic compound layer includes shining
It is selected in the group of layer, hole transmission layer, hole injection layer, electron transfer layer, electron injecting layer, hole blocking layer and combinations thereof
Organic electroluminescence device.
7. organic electroluminescence device according to claim 6, it is characterised in that: the organic electroluminescence device includes organic hair
Optical device, organic photovoltaic cell, Electronic Paper, Organophotoreceptor or Organic Thin Film Transistors.
8. a kind of organic luminescent device using organic compound described in claim 1-4 any one, including first electrode,
Two electrodes and the one or more organic compound layers being placed between two electrode, it is characterised in that: at least one organises
It closes nitride layer and uses at least one organic compound.
9. organic luminescent device according to claim 8, it is characterised in that: the organic compound layer includes shining
It is selected in the group of layer, hole transmission layer, hole injection layer, electron transfer layer, electron injecting layer, hole blocking layer and combinations thereof
Organic electroluminescence device.
10. organic luminescent device according to claim 9, it is characterised in that: the organic electroluminescence device further includes organic
Photoelectric device, organic luminescent device, organic sun device, Organophotoreceptor, Electronic Paper and organic memory device and combinations thereof
The organic electroluminescence device selected in group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811439378.6A CN109734607B (en) | 2018-11-29 | 2018-11-29 | Organic compound, organic electroluminescent device and organic light-emitting device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811439378.6A CN109734607B (en) | 2018-11-29 | 2018-11-29 | Organic compound, organic electroluminescent device and organic light-emitting device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109734607A true CN109734607A (en) | 2019-05-10 |
| CN109734607B CN109734607B (en) | 2022-04-08 |
Family
ID=66358270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811439378.6A Active CN109734607B (en) | 2018-11-29 | 2018-11-29 | Organic compound, organic electroluminescent device and organic light-emitting device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109734607B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112300052A (en) * | 2019-07-23 | 2021-02-02 | 北京鼎材科技有限公司 | Compound, application thereof and organic electroluminescent device comprising compound |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101172963A (en) * | 2006-11-03 | 2008-05-07 | 上海拓引数码技术有限公司 | Compound for organic luminescent material and method for producing the same |
| JP2011173973A (en) * | 2010-02-24 | 2011-09-08 | Toyo Ink Sc Holdings Co Ltd | Material for organic electroluminescent element and application thereof |
| US20140353617A1 (en) * | 2013-06-04 | 2014-12-04 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting diode including the same |
| CN106565705A (en) * | 2016-10-26 | 2017-04-19 | 北京绿人科技有限责任公司 | Organic compound, and application thereof in electroluminescent device |
| CN108290875A (en) * | 2015-12-01 | 2018-07-17 | 德山新勒克斯有限公司 | Organic electronic element compound, organic electronic element and its electronic device using it |
| CN111511734A (en) * | 2017-12-21 | 2020-08-07 | 德山新勒克斯有限公司 | Compound for organic electric element, organic electric element using same, and electronic device using same |
-
2018
- 2018-11-29 CN CN201811439378.6A patent/CN109734607B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101172963A (en) * | 2006-11-03 | 2008-05-07 | 上海拓引数码技术有限公司 | Compound for organic luminescent material and method for producing the same |
| JP2011173973A (en) * | 2010-02-24 | 2011-09-08 | Toyo Ink Sc Holdings Co Ltd | Material for organic electroluminescent element and application thereof |
| US20140353617A1 (en) * | 2013-06-04 | 2014-12-04 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting diode including the same |
| CN108290875A (en) * | 2015-12-01 | 2018-07-17 | 德山新勒克斯有限公司 | Organic electronic element compound, organic electronic element and its electronic device using it |
| CN106565705A (en) * | 2016-10-26 | 2017-04-19 | 北京绿人科技有限责任公司 | Organic compound, and application thereof in electroluminescent device |
| CN111511734A (en) * | 2017-12-21 | 2020-08-07 | 德山新勒克斯有限公司 | Compound for organic electric element, organic electric element using same, and electronic device using same |
Non-Patent Citations (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112300052A (en) * | 2019-07-23 | 2021-02-02 | 北京鼎材科技有限公司 | Compound, application thereof and organic electroluminescent device comprising compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109734607B (en) | 2022-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107089990B (en) | It is a kind of using fluorenes as the organic compound of core and its application on organic electroluminescence device | |
| KR20100129101A (en) | Materials for organic electroluminescent devices | |
| KR20130007934A (en) | Organic electroluminescence device using the triphenylene derivative | |
| KR20100009523A (en) | Compounds for organic electronic devices | |
| CN106543123B (en) | A kind of anthracene compound and preparation method thereof and organic luminescent device | |
| CN105418485B (en) | A kind of new green light host compound and its preparation method and application | |
| TW201309675A (en) | Compound for organic electroluminescent device and organic electroluminescent devices using the same | |
| CN107337680B (en) | It is a kind of using fluorenes as the organic compound of core and its application in OLED device | |
| CN109734608A (en) | A kind of organic compound and its organic electroluminescence device using the compound | |
| CN109761877A (en) | A kind of organic compound and its organic electroluminescence device using the compound | |
| CN107057681A (en) | A kind of photoelectric material containing xanthene structure and its application in OLED fields | |
| CN106146538B (en) | A kind of amine compounds and preparation method thereof and luminescent device | |
| CN106187963A (en) | One is containing anthracene compounds and preparation method thereof and a kind of organic luminescent device | |
| CN108623430A (en) | Dinaphthalene derivatives, material and organic electroluminescence device comprising the dinaphthalene derivatives | |
| CN106749050B (en) | It is a kind of using cyclic diketones as the hot activation delayed fluorescence OLED material of core and its application | |
| CN108165264A (en) | A kind of organic luminescent compounds and its preparation method and application | |
| CN109734648A (en) | Organic electroluminescence device compound and its organic electroluminescence device for using the compound | |
| CN109734607A (en) | A kind of organic compound and its organic electroluminescence device and organic luminescent device | |
| CN108264487A (en) | A kind of novel glyoxaline compound and its application | |
| CN106565434A (en) | Anthracene compound, preparing method of anthracene compound and organic light-emitting device | |
| CN108949152A (en) | It is a kind of that acridine is joined as the thermal activities delayed fluorescence organic compound of donor and its preparation and application using carbazole | |
| CN108727375A (en) | A kind of delayed fluorescence compound and preparation method thereof and organic electroluminescence device | |
| CN114736148A (en) | Triarylamine compound, organic material containing triarylamine compound, and organic light-emitting device | |
| CN106588592A (en) | Dianthranide derivative, preparation method, and application thereof | |
| CN108264486A (en) | A kind of novel glyoxaline compound and its preparation and electroluminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: An organic compound and its organic electro-device and organic light-emitting device Effective date of registration: 20220831 Granted publication date: 20220408 Pledgee: China Merchants Bank Co.,Ltd. Shanghai Branch Pledgor: UIV CHEM-YURUI (SHANGHAI) CHEMICAL CO.,LTD. Registration number: Y2022310000223 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |