CN105968041B - Xenyl bis-carbazole compound and preparation method thereof and the organic luminescent device made of the compound - Google Patents
Xenyl bis-carbazole compound and preparation method thereof and the organic luminescent device made of the compound Download PDFInfo
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Abstract
The present invention relates to a kind of xenyl bis-carbazole compound and preparation method thereof and the organic luminescent devices made of the compound, belong to electroluminescent organic material technical field.Solve thermal stability of the existing aromatic amine compound as electroluminescent material when, quick hole degree of excursion, illuminator efficiency and service life all poor technical problem.Xenyl bis-carbazole compound provided by the invention is used to prepare organic luminescent device, and device light emitting efficiency and life characteristic obtained increase significantly, better heat stability.Organic luminescent device of good performance made of xenyl bis-carbazole compound using preparation method provided by the invention preparation can be applied to the high OLED industry of practicability, flat panel show, planar illuminant, illumination face illuminating OLED illuminator, flexibility illuminator, duplicator, printer, LCD backlight lamp or light source, display board, the mark of dosing machine class etc., have a good application prospect.
Description
Technical field
The present invention relates to electroluminescent organic material technical fields, and in particular to a kind of xenyl bis-carbazole compound and
Preparation method and the organic luminescent device made of the compound.
Background technique
Organic electroluminescence device (OLED) is used as a kind of flat panel display, has such as self-luminous, high brightness, wide view
The many merits such as angle, ultra-thin, low energy consumption, fast response time, rollable, achievable Full color.Therefore, in most recent two decades,
The device achieves the development advanced by leaps and bounds, and the process of industrialization is also in continuous forward impelling.Electroluminescent organic material pair
The performance of organic luminescent device plays very important effect.According to the size of electroluminescent organic material molecular weight, Ke Yifen
For small molecule electroluminescent organic material and macromolecule electroluminescent organic material.In presently disclosed luminescent material, due to small
The fluorescence quantum efficiency of molecule electroluminescent material is high, is easily purified, light emission luminance and excitation purity are also superior to high molecular material, institute
With small molecule electroluminescent material is applied to luminescent device and has started to realize commercialization.
Aromatic amine compound is a kind of important small molecule electroluminescent organic material, such as TPD, α-NPD and public affairs
Compound disclosed in the number of opening US20150014657 is as follows:
But these presently disclosed aromatic amine compounds as electroluminescent material when thermal stability, quickly
Hole degree of excursion, illuminator efficiency and service life are all poor.
Summary of the invention
Thermal stability, quick hole when the invention solves existing aromatic amine compounds as electroluminescent material
Degree of excursion, illuminator efficiency and service life all poor technical problem provide a kind of xenyl bis-carbazole compound and its system
Preparation Method and the organic luminescent device made of the compound.
In order to solve the above-mentioned technical problem, technical solution of the present invention is specific as follows:
A kind of xenyl bis-carbazole compound, the general molecular formula of the compound is such as shown in [chemical formula 1]:
[chemical formula 1]
In formula, Ar1Substituent group is selected from substituted or unsubstituted C18~C24 xenyl, substituted or unsubstituted C10~C18
Heterocycle, substituted or unsubstituted C10~C18 condensed ring radical, phenyl or triphenylamine base；
R1Substituent group is hydrogen, phenyl, propyl or isobutyl group.
In the above-mentioned technical solutions, the xenyl bis-carbazole compound is appointed in following chemical formula 2-1~2-11
The specific compound that a chemical formula of anticipating indicates:
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
[chemical formula 2-5]
[chemical formula 2-6]
[chemical formula 2-7]
[chemical formula 2-8]
[chemical formula 2-9]
[chemical formula 2-10]
[chemical formula 2-11]
In the above-mentioned technical solutions, the xenyl bis-carbazole compound is any one in following A -1~A-74
The specific compound that chemical formula indicates:
A kind of preparation method of xenyl bis-carbazole compound, comprising the following steps:
It takes bromo- 3,5- bis- (9- carbazole) biphenyl of 3'-, contain Ar1-R1The boronic acid compounds of substituent group, tetra-triphenylphosphine palladium and
Potassium carbonate dissolves them in toluene: H2The in the mixed solvent of O=2:1,80 DEG C of stirring 5h, nitrogen protection are anti-to TLC monitoring
It after answering, is cooled to room temperature, is evaporated after organic phase anhydrous magnesium sulfate drying after being extracted with methylene chloride and water, product column layer
Analyse to obtain xenyl bis-carbazole compound.
In the above-mentioned technical solutions, the specific preparation method of bromo- 3,5- bis- (9- carbazole) biphenyl of the 3'- are as follows: the bromo- 3- fluorobenzene of 1-
8.9mmol, (3,5- bis- (9H- carbazole -9- base) phenyl) boric acid 9.8mmol, tetra-triphenylphosphine palladium 0.3mmol and potassium carbonate
0.02mol is dissolved in the toluene of 100mL: H2O=2:1 in the mixed solvent, 80 DEG C of stirring 5h, nitrogen protection are monitored to TLC and are reacted
After, it is cooled to room temperature, with being evaporated after organic phase anhydrous magnesium sulfate drying after methylene chloride and water extraction, product column is chromatographed
Obtain bromo- 3,5- bis- (9- carbazole) biphenyl of 3'-.
The organic luminescent device made of xenyl bis-carbazole compound, including first electrode, second electrode and be placed in
One or more organic compound layers between two electrode, which is characterized in that at least one organic compound layer includes extremely
A kind of few xenyl bis-carbazole compound.
Above-mentioned xenyl bis-carbazole compound is single form or is included in other material mixing forms above-mentioned organic
In compound layer.
Above-mentioned organic compound layer includes at least hole injection layer, hole transmission layer, had both had hole injection but also with sky
It transmits technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both has electronics biography in cave
Defeated any one layer but also in electron injection technical ability layer.
Above-mentioned hole injection layer, hole transmission layer and both have hole injection but also in hole transport technical ability layer at least one
It is a be usual hole injecting material, hole transporting material and both have hole injection but also with other than hole transport technical ability substance also
Including being electronically generated substance.
" organic compound layer " refers to disposing between organic luminescent device first electrode and second electrode in the present invention
The term of whole layers.
For example, including luminescent layer in above-mentioned organic compound layer, above-mentioned organic compound layer includes phosphorescence host, fluorescence master
More than one in body, phosphorescence doping and fluorescence doping, including xenyl bis-carbazole compound above-mentioned in above-mentioned luminescent layer,
I) above-mentioned fluorescent host can be above-mentioned xenyl bis-carbazole compound；Ii) above-mentioned fluorescence doping can be above-mentioned xenyl
Bis-carbazole compound；Iii) above-mentioned fluorescent host and fluorescence doping can be above-mentioned xenyl bis-carbazole compound.
Above-mentioned luminescent layer can be red, yellow or cyan luminescent layer.For example, above-mentioned xenyl when above-mentioned luminescent layer cyan
The use of bis-carbazole compound adulterates purposes in cyan main body or cyan, provides high efficiency, high brightness, high-resolution and long-life
Organic luminescent device.
And above-mentioned organic compound level includes electron transfer layer, and above-mentioned electron transfer layer includes the double clicks of above-mentioned xenyl
Azole compounds.It includes the change containing metal that wherein above-mentioned electron transfer layer is other than above-mentioned xenyl bis-carbazole compound again
Close object.
Above-mentioned organic compound layer all includes luminescent layer and electron transfer layer, and above-mentioned luminescent layer and electron transfer layer the inside are each
Including above-mentioned xenyl bis-carbazole compound (the above-mentioned xenyl bis-carbazole for including in above-mentioned luminescent layer and electron transfer layer
Compound can be the same or different).
Above-mentioned organic luminescent device utilizes the xenyl bis-carbazole compound of chemical formula 1, with common organic electronic device
Part manufacturing method and materials synthesis.
Another aspect of the present invention is that above-mentioned device can be used in organic luminescent device (OLED), organic sun with same principle
Battery (OSC), Electronic Paper (e-paper), Organophotoreceptor (OPC) or Organic Thin Film Transistors (OTFT).
Above-mentioned organic luminescent device is to utilize the methods of film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) on substrate
Evaporation metal and conductive oxide and their alloy form anode, above-mentioned hole injection layer, hole transmission layer, hair
The method synthesis of evaporation cathode again after photosphere, hole blocking layer and electron transfer layer.Cathode object on substrate other than above method
Matter starts organic matter layer, anode material and production organic luminescent device is deposited in order.
Above-mentioned organic compound layer also may include hole injection layer, hole transmission layer, luminescent layer, hole blocking layer and electricity
The multilayered structure of sub- transport layer, and above-mentioned organic compound layer is the high molecular material solvent engineering substitution vapor deposition using multiplicity
Method, such as: spin-coating (spin-coating), strip form (tape-casting), scraping blade method (doctor-
Blading), the methods of silk-screen printing (Screen-Printing), ink jet printing or thermal imaging (Thermal-Imaging) subtract
Few number of plies manufacture.
Organic luminescent device according to the present invention is by the material used can front shines, back side illuminated or two sides are sent out
Light.
The compound of the present invention can be adapted for organic photovoltaic cell, illumination with OLED, flexibility OLED, Organophotoreceptor,
In the organic assemblies such as organic transistor, it is readily applicable to organic luminescent device and is applicable in the device of similar principle.
The beneficial effects of the present invention are:
The luminous efficiency of the organic luminescent device of xenyl bis-carbazole compound preparation provided by the invention and service life are special
Property increases significantly, better heat stability.
Organic hair of good performance made of xenyl bis-carbazole compound using preparation method provided by the invention preparation
Optical device can be applied to the high OLED industry of practicability, flat panel is shown, planar illuminant, illumination face illuminating OLED shine
Body, flexible illuminator, duplicator, printer, LCD backlight lamp or light source, display board, the mark of dosing machine class etc., have fine
Application prospect.
Specific embodiment
Xenyl bis-carbazole compound provided by the invention is with bromo- 3,5-, bis- (9- carbazole) biphenyl of 3'- for raw material, even
It connects containing Ar1-R1The boronic acid compounds of substituent group generate the xenyl bis-carbazole compound containing different substituents.Synthesize road
Line is as follows:
Embodiment 1
The preparation of bromo- 3,5- bis- (9- carbazole) biphenyl of intermediate 3'-:
The bromo- 3- fluorobenzene 8.9mmol of 1-, (3,5- bis- (9H- carbazole -9- base) phenyl) boric acid 9.8mmol, tetra-triphenylphosphine palladium
0.3mmol and potassium carbonate 0.02mol is dissolved in the toluene of 100mL: H2O=2:1 in the mixed solvent, 80 DEG C of stirring 5h, nitrogen are protected
Shield after reaction to TLC monitoring is cooled to room temperature, dry with organic phase anhydrous magnesium sulfate after methylene chloride and water extraction
After be evaporated, product column chromatographs to obtain bromo- 3,5- bis- (9- carbazole) the biphenyl 7.92mmol of 3'-, yield 89%.Mass spectrum: 563.52.
The synthesis of final products xenyl bis-carbazole compound (A-1), synthetic route are as follows:
Bromo- 3,5- bis- (9- carbazole) biphenyl 8.9mmol, the 9- anthracene boric acid 9.8mmol, tetra-triphenylphosphine palladium 0.3mmol of 3'- and
Potassium carbonate 0.02mol is dissolved in the toluene of 100mL: H2O=2:1 in the mixed solvent, 80 DEG C of stirring 5h, nitrogen protection are supervised to TLC
It surveys after reaction, is cooled to room temperature, be evaporated after organic phase anhydrous magnesium sulfate drying after being extracted with methylene chloride and water, product
Column chromatographs to obtain 9,9'- (3'- (anthracene -9- base)-[1,1'- biphenyl] -3,5- diyl) two (9H- carbazole) (A-1) 7.83mmol, yield
88%.Mass spectrum: 660.80.
Embodiment 2-74
For the synthetic method of embodiment 2-74 with embodiment 1, reactive material used in each embodiment generates substance and yield converges
Always (it is shown in Table 1).
1 embodiment 2-74 reactive material of table, generation substance and yield summarize
Organic luminescent device prepares embodiment:
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic wave is washed
It washs 30 minutes, is cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleans, isopropanol, acetone, first
Ultrasonic washing is later dry in order for alcohol equal solvent, is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes,
It is sent in evaporator.
Hole injection layer 2-TNATA vapor deposition is deposited on the ito glass substrate having had been prepared forHole transmission layer
The xenyl bis-carbazole compound for the embodiment preparation recorded in a-NPD or table 2(9,10- is bis- by blue main body A ND
(2- naphthalene) anthracene), dopant material TPPDA (N1, N1, N6, N6- tetraphenyl pyrene -1,6- diamines) 5% is mixedThickness steams
Plating, hole blocking layer and hole transmission layerCathode LiF5Above process organic matter vaporization plating
Speed is to maintainLiF isAl is
The organic luminescent device that the present invention is prepared is using 2400 type source measuring unit of KEITHLEY Keithley, CS-
2000 spectroradio luminance meters are tested, to evaluate driving voltage, light emission luminance, luminous efficiency and the luminous face of luminescent device
Color；Characteristics of luminescence test to obtained device the results are shown in Table 2, and table 2 is the xenyl bis-carbazole of preparation of the embodiment of the present invention
Compound and the characteristics of luminescence test result for comparing luminescent device prepared by substance.
The characteristics of luminescence table of 2 device of table
The new xenyl bis-carbazole chemical combination provided by the invention with 1 structure of chemical formula can be found out from 2 result of table
The luminous efficiency and life characteristic of the organic luminescent device of object preparation increase significantly.
Organic luminescent device available luminous efficiency and longevity of the present invention using the preparation of xenyl bis-carbazole compound
Order good as a result, therefore compound provided by the invention can be applied to the high OLED industry of practicability.Organic hair of the invention
Optical device is applicable to flat panel and shows, planar illuminant, illumination face illuminating OLED illuminator, flexible illuminator, duplicates
Machine, printer, LCD backlight lamp or light source, display board, the mark of dosing machine class etc..
The explanation of above embodiments is only applicable to facilitate the understanding of the method and its core concept of the invention.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (4)
1. a kind of xenyl bis-carbazole compound, which is characterized in that it is that any one following chemical formula indicate specific
Compound:
2. the preparation method of xenyl bis-carbazole compound according to claim 1, which is characterized in that including following step
It is rapid:
It takes bromo- 3,5- bis- (9- carbazole) biphenyl of 3'-, contain Ar1-R1Boronic acid compounds, tetra-triphenylphosphine palladium and the carbonic acid of substituent group
Potassium dissolves them in toluene: H2The in the mixed solvent of O=2:1,80 DEG C of stirring 5h, nitrogen protection monitor reaction knot to TLC
Shu Hou is cooled to room temperature, and with being evaporated after organic phase anhydrous magnesium sulfate drying after methylene chloride and water extraction, product column is chromatographed
Xenyl bis-carbazole compound；
Wherein, containing Ar1-R1The boronic acid compounds of substituent group are one of having structure:
3. the preparation method of xenyl bis-carbazole compound according to claim 2, which is characterized in that the 3'- is bromo-
The specific preparation method of 3,5- bis- (9- carbazole) biphenyl are as follows: the bromo- 3- fluorobenzene 8.9mmol of 1-, (3,5- bis- (9H- carbazole -9- base) phenyl)
Boric acid 9.8mmol, tetra-triphenylphosphine palladium 0.3mmol and potassium carbonate 0.02mol are dissolved in the toluene of 100mL: H2O=2:1 mixing
In solvent, 80 DEG C of stirring 5h, nitrogen protection after reaction to TLC monitoring is cooled to room temperature, and is extracted with methylene chloride and water
It is evaporated after organic phase anhydrous magnesium sulfate drying afterwards, product column chromatographs to obtain bromo- 3,5- bis- (9- carbazole) biphenyl of 3'-.
4. the organic luminescent device made of xenyl bis-carbazole compound described in claim 1, including first electrode,
Two electrodes and the one or more organic compound layers being placed between two electrode, which is characterized in that at least one organises
Closing nitride layer includes at least one xenyl bis-carbazole compound.
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| CN1895004A (en) * | 2003-12-15 | 2007-01-10 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
| JP2012019176A (en) * | 2010-07-09 | 2012-01-26 | Fujifilm Corp | Organic electroluminescent element |
| WO2014017094A1 (en) * | 2012-07-25 | 2014-01-30 | 出光興産株式会社 | Organic electroluminescence element |
| WO2016105138A2 (en) * | 2014-12-26 | 2016-06-30 | 주식회사 두산 | Organic compound and organo-electroluminescent device including same |
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| CN1895004A (en) * | 2003-12-15 | 2007-01-10 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
| JP2012019176A (en) * | 2010-07-09 | 2012-01-26 | Fujifilm Corp | Organic electroluminescent element |
| WO2014017094A1 (en) * | 2012-07-25 | 2014-01-30 | 出光興産株式会社 | Organic electroluminescence element |
| WO2016105138A2 (en) * | 2014-12-26 | 2016-06-30 | 주식회사 두산 | Organic compound and organo-electroluminescent device including same |
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