CN110526874A - Fluorenes and phenazene derivative and preparation method thereof and OLED device - Google Patents
Fluorenes and phenazene derivative and preparation method thereof and OLED device Download PDFInfo
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- CN110526874A CN110526874A CN201910802835.1A CN201910802835A CN110526874A CN 110526874 A CN110526874 A CN 110526874A CN 201910802835 A CN201910802835 A CN 201910802835A CN 110526874 A CN110526874 A CN 110526874A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Optics & Photonics (AREA)
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- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of fluorenes and phenazene derivatives, functional group's collocation is obtained by specific, by the fluorenyl with excellent hole transport performance and upper azophenlyene group, key is even with arylamine group again, the hole mobile material with high mobility is designed, there is excellent current efficiency and external quantum efficiency with the OLED device that this is prepared.
Description
Technical field
The present invention relates to OLED material fields, and in particular to a kind of fluorenes and phenazene derivative and preparation method thereof and OLED device
Part.
Background technique
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is shone not with its active
Need that backlight, luminous efficiency are high, visible angle is big, fast response time, Acclimation temperature range are big, production and processing technology is relatively simple
The advantages that list, driving voltage are low, and energy consumption is small, lighter and thinner, Flexible Displays and huge application prospect, have attracted numerous researchs
The concern of person.
For in top emission OLED device used at present, hole mobile material as most thick one layer, energy level and
Hole mobility always exists contradictory relationship, and exploitation matches energy level and the hole mobile material of high mobility is extremely urgent.
Summary of the invention
The present invention provides a kind of fluorenes and phenazene derivative, hole mobility with higher, as hole transport material
The OLED device of material has high luminous efficiency and quantum efficiency.
To solve the above problems, in a first aspect, the present invention provides a kind of fluorenes and phenazene derivative, the fluorenes and azophenlyene is derivative
Object has structure shown in general formula (1):
Wherein, R1For C12-30Aryl amine,
R2For C1-10Alkyl or C6-20Aryl,
N is 0,1,2,3 or 4, and when n is 2,3 or 4, multiple R2It is identical or not identical.
Further, the R1In following structural formula any one:
Further, the R2In methyl, ethyl, propyl, butyl, phenyl, xenyl, naphthalene and anthryl at least
One.
Second aspect, the present invention also provides the preparation methods of a kind of fluorenes and phenazene derivative, include the following steps:
S1: the first reactant, the second reactant, palladium catalyst and organophosphorus ligand are added into reaction unit, then exists
Be added alkali in anhydrous and oxygen-free environment, first reactant, the second reactant, palladium catalyst, organophosphorus ligand and alkali mole
Than for 1:(1-1.5): (0.01-0.1): (0.1-0.5): (1-5),
First reactant has structure shown in general formula (1), and second reactant has knot described in general formula (2)
Structure:
Wherein, R1For C12-30Aryl amine,
R2For C1-10Alkyl or C6-20Aryl,
N is 0,1,2,3 or 4, and when n is 2,3 or 4, multiple R2 are identical or not identical,
And X is halogen；
S2: under inert gas protection, the solvent of water removal deoxygenation is added in Xiang Suoshu reaction unit, is warming up to the first temperature
Reaction at the first time, after being cooled to second temperature, obtains the first reaction solution；
S3: separation and purification operation is carried out to get product to first reaction solution.
Further, the palladium catalyst is tris(dibenzylideneacetone) dipalladium, palladium acetate and 1,1'- bis- (diphenyl phosphine)
Any one in ferrocene palladium chloride (II).
Further, the organophosphorus ligand is tri-tert-butylphosphine, tri-tert-butylphosphine tetrafluoroborate and bis- (2- diphenyl
Phosphine) any one in phenylate.
Further, the alkali is any one in sodium tert-butoxide, potassium tert-butoxide, cesium carbonate, sodium carbonate and potassium carbonate.
Further, the first temperature described in S2 step is 80-140 DEG C, and the second temperature is 20-60 DEG C, described the
One time was 12-48h.
Further, separation and purification operation described in S3 step includes: that first reaction solution is added in ice water, is used
Methylene chloride extracts 2-5 times, merges organic phase, and revolving reuses methylene chloride and n-hexane mixed liquor and carries out as eluent
The volume ratio of column chromatography, the methylene chloride and n-hexane is 1:(1-10).
In addition, the present invention also provides a kind of OLED device, including first electrode and second electrode, the first electrode and the
It include hole transmission layer, luminescent layer and electron transfer layer between two electrodes, the hole transmission layer includes above-mentioned fluorenes and azophenlyene spreads out
Biology.
The utility model has the advantages that the present invention obtains functional group's collocation by specific, simultaneously by the fluorenyl with excellent hole transport performance
Upper azophenlyene group, then key design the hole mobile material with high mobility, can realize high efficiency with this even with arylamine group
The preparation of organic electroluminescence device.
Detailed description of the invention
To describe the technical solutions in the embodiments of the present invention more clearly, make required in being described below to embodiment
Attached drawing is briefly described, it should be apparent that, drawings in the following description are only some embodiments of the invention, for
For those skilled in the art, without creative efforts, it can also be obtained according to these attached drawings other attached
Figure.
Fig. 1 is that the embodiment of the present invention provides a kind of OLED device structural schematic diagram.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, those skilled in the art's every other implementation obtained without creative efforts
Example, shall fall within the protection scope of the present invention.
In order to can be realized any person skilled in the art and use the present invention, gives and be described below.It is retouched following
In stating, details is listed for purposes of explanation.It should be appreciated that those skilled in the art will realize that In
The present invention also may be implemented in the case where without using these specific details.In other examples, will not be to well known structure and mistake
Journey is described in detail, and so that description of the invention is become obscure to avoid unnecessary details.Therefore, the present invention is not intended to limit
The embodiment shown in, but it is consistent with the widest scope for meeting principle and feature disclosed in the present application.
Embodiment 1
Target compound 1 is prepared, route is as follows:
Raw material 1 (3.06g, 5mmol) is added into bis- mouthfuls of bottles of 250mL, carbazole (1.00g, 6mmol), palladium acetate (45mg,
0.2mmol) with tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol), NaOt-Bu is then added in glove box
(0.58g, 6mmol) squeezes into the toluene that 100mL removes water deoxygenation in advance under argon atmosphere, reacts 24 hours at 120 DEG C.It is cooling
To room temperature, reaction solution is poured into 200mL ice water, methylene chloride extracts three times, merges organic phase, revolving, and column chromatographs (dichloromethane
Alkane: n-hexane, v:v, 1:5) it isolates and purifies, obtain white powder 2.0g, yield 57%.
MS(EI)m/z:[M]+:699.36。
Embodiment 2
Target compound 2 is prepared, route is as follows:
Raw material 1 (3.06g, 5mmol) is added into bis- mouthfuls of bottles of 250mL, diphenylamines (1.01g, 6mmol), palladium acetate
(45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol), is then added NaOt-Bu in glove box
(0.58g, 6mmol) squeezes into the toluene that 100mL removes water deoxygenation in advance under argon atmosphere, reacts 24 hours at 120 DEG C.It is cooling
To room temperature, reaction solution is poured into 200mL ice water, methylene chloride extracts three times, merges organic phase, rotation is at silica gel, column chromatography (two
Chloromethanes: n-hexane, v:v, 1:5) it isolates and purifies, obtain white powder 2.2g, yield 63%.
MS(EI)m/z:[M]+:701.33。
Embodiment 3
Target compound 3 is prepared, route is as follows:
Raw material 1 (3.06g, 5mmol) is added into bis- mouthfuls of bottles of 250mL, 9,9 '-dimethyl acridiniums (1.26g, 6mmol), vinegar
Sour palladium (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol), are then added in glove box
NaOt-Bu (0.58g, 6mmol) squeezes into the toluene that 100mL removes water deoxygenation in advance under argon atmosphere, small in 120 DEG C of reactions 24
When.It is cooled to room temperature, reaction solution is poured into 200mL ice water, methylene chloride extracts three times, merges organic phase, revolves into silica gel, column
Chromatography (methylene chloride: n-hexane, v:v, 1:5) isolates and purifies, and obtains white powder 2.3g, yield 62%.
MS(EI)m/z:[M]+:741.32。
The test of HOMO/LUMO energy level is carried out to the compound 1-3 of above-mentioned preparation, the results are shown in Table 1:
Table 1
| HOMO(eV) | LUMO(eV) | |
| Compound 1 | -5.58 | -2.56 |
| Compound 2 | -5.61 | -2.58 |
| Compound 3 | -5.66 | -2.57 |
Application Example 1
OLED device 1 is prepared, as shown in Figure 1, on substrate 1, sequentially forming anode 2, hole injection layer 3, sky in order
Cave transport layer 4, electronic barrier layer 5, organic luminous layer 6, hole blocking layer 7, electron transfer layer 8, electron injecting layer 9, cathode 10
And optical coupling output layer 11:
The anode 2 is the lamination film layer structure of ITO/Ag/ITO (15/140/15nm)；
The hole injection layer 3 is six cyano -1,4,5,8,9,12- of 2,3,6,7,10,11-, six azepine of 100nm thickness
Benzophenanthrene (HATCN)；
The hole transmission layer 4 is the compound 1 of the above-mentioned preparation of 130nm thickness；
The electronic barrier layer 5 is the (4- [1- [4- [two (4- aminomethyl phenyl) amino] phenyl] cyclohexyl]-of 5nm thickness
N- (3- aminomethyl phenyl)-N- (4- aminomethyl phenyl) aniline (TAPC)；
The organic luminous layer 6 is that 4,4 '-two (9- carbazyl) biphenyl of 40nm thickness and three (2- phenylpyridines) close iridium
(III) mass ratio that mixture, described 4,4 '-two (9- carbazyl) biphenyl and three (2- phenylpyridines) close iridium (III) is 9:1；
The hole blocking layer 7 be 15nm thickness 3,3'- [5'- [3- (3- pyridyl group) phenyl] [and 1,1':3', 1 "-three
Biphenyl] -3,3 "-diyl] two pyridines (TMPyPb)；
The electron transfer layer 8 is the mixture of 8-hydroxyquinoline-lithium (LiQ) and TMPyPb of 30nm thickness, the LiQ
Mass ratio with TMPyPb is 1:1；
The electron injecting layer 9 is the ytterbium of 1nm thickness；
The cathode 10 is the magnesium silver mixture of 11nm thickness, and the magnesium and silver-colored mass ratio are 1:10；
The optical coupling output layer 11 is 4,4', 4 "-three (carbazole -9- base) triphenylamines (TCTA) of 100nm thickness,
The specific preparation method of above-mentioned device is not particularly limited, no longer superfluous herein using the conventional selection of this field
It states.
Application Example 2
OLED device 2 is prepared, in addition to using the compound 2 of above-mentioned preparation to replace compound 1 as hole transport layer material
Except, other are identical with Application Example 1.
Application Example 3
OLED device 3 is prepared, in addition to using the compound 3 of above-mentioned preparation to replace compound 1 as hole transport layer material
Except, other are identical with Application Example 1.
The device 1-3 of above-mentioned preparation is tested for the property, data are as shown in table 2:
Table 2
| Device | Hole transmission layer | Maximum current efficiency (cd/A) | (CIEx,CIEy) | Maximum external quantum efficiency (%) |
| Device 1 | Compound 1 | 43.3 | (0.685,0.290) | 41.9% |
| Device 2 | Compound 2 | 42.1 | (0.685,0.290) | 40.3% |
| Device 3 | Compound 3 | 42.8 | (0.685,0.290) | 40.8% |
Above-mentioned data reflect, using a kind of fluorenes provided by the present invention and phenazene derivative is as hole mobile material, and
The OLED device of preparation has excellent performance, is embodied in it with considerable current efficiency and external quantum efficiency.
Fluorenes and phenazene derivative and preparation method thereof is provided for the embodiments of the invention above to carry out with OLED device
It is discussed in detail, used herein a specific example illustrates the principle and implementation of the invention, above embodiments
Illustrate to be merely used to help understand method and its core concept of the invention；Meanwhile for those skilled in the art, according to this
The thought of invention, there will be changes in the specific implementation manner and application range, in conclusion the content of the present specification is not answered
It is interpreted as limitation of the present invention.
Claims (10)
1. a kind of fluorenes and phenazene derivative, which is characterized in that simultaneously phenazene derivative has structure shown in general formula (1) to the fluorenes:
Wherein, R1For C12-30Aryl amine,
R2For C1-10Alkyl or C6-20Aryl,
N is 0,1,2,3 or 4, and when n is 2,3 or 4, multiple R2It is identical or not identical.
2. fluorenes as described in claim 1 and phenazene derivative, which is characterized in that the R1It is any one in following structural formula
Kind:
3. fluorenes as claimed in claim 1 or 2 and phenazene derivative, which is characterized in that the R2Selected from methyl, ethyl, propyl,
At least one of butyl, phenyl, xenyl, naphthalene and anthryl.
4. the preparation method of a kind of fluorenes and phenazene derivative, which comprises the steps of:
S1: the first reactant, the second reactant, palladium catalyst and organophosphorus ligand are added into reaction unit, then anhydrous
Be added alkali in oxygen-free environment, first reactant, the second reactant, palladium catalyst, organophosphorus ligand and alkali molar ratio be
1:(1-1.5): (0.01-0.1): (0.1-0.5): (1-5),
First reactant has structure shown in general formula (1), and second reactant has structure described in general formula (2):
Wherein, R1For C12-30Aryl amine,
R2For C1-10Alkyl or C6-20Aryl,
N is 0,1,2,3 or 4, and when n is 2,3 or 4, multiple R2 are identical or not identical,
And X is halogen；
S2: under inert gas protection, the solvent of water removal deoxygenation is added in Xiang Suoshu reaction unit, is warming up to the first thermotonus
At the first time, after being cooled to second temperature, the first reaction solution is obtained；
S3: separation and purification operation is carried out to get product to first reaction solution.
5. preparation method as claimed in claim 4, which is characterized in that palladium catalyst described in S1 step is three (dibenzylidenes
Acetone) any one in two palladiums, palladium acetate and 1,1'- bis(diphenylphosphino) ferrocene dichloropalladium (II).
6. preparation method as claimed in claim 4, which is characterized in that organophosphorus ligand described in S1 step is tri-tert
Any one in phosphine, tri-tert-butylphosphine tetrafluoroborate and bis- (2- diphenylphosphine) phenylates.
7. preparation method as claimed in claim 4, which is characterized in that alkali described in S1 step be sodium tert-butoxide, potassium tert-butoxide,
Any one in cesium carbonate, sodium carbonate and potassium carbonate.
8. the preparation method as described in claim 4-7 any one, which is characterized in that the first temperature described in S2 step is
80-140 DEG C, the second temperature is 20-60 DEG C, and the first time is 12-48h.
9. the preparation method as described in claim 4-7 any one, which is characterized in that separation and purification operation described in S3 step
Include: that first reaction solution is added in ice water, make to be extracted with dichloromethane 2-5 times, merge organic phase, revolving reuses
Methylene chloride and n-hexane mixed liquor carry out column chromatography as eluent, and the volume ratio of the methylene chloride and n-hexane is 1:
(1-10)。
10. a kind of OLED device, including first electrode and second electrode include that hole passes between the first electrode and second electrode
Defeated layer, luminescent layer and electron transfer layer, which is characterized in that the hole transmission layer includes described in claim 1-3 any one
Fluorenes and phenazene derivative.
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| CN201910802835.1A CN110526874A (en) | 2019-08-28 | 2019-08-28 | Fluorenes and phenazene derivative and preparation method thereof and OLED device |
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| CN201910802835.1A CN110526874A (en) | 2019-08-28 | 2019-08-28 | Fluorenes and phenazene derivative and preparation method thereof and OLED device |
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| CN110105330A (en) * | 2019-05-31 | 2019-08-09 | 武汉华星光电半导体显示技术有限公司 | It is a kind of efficiently bluish-green to orange light thermal activation delayed fluorescence material and its preparation method and application |
| CN110128323A (en) * | 2019-03-08 | 2019-08-16 | 武汉尚赛光电科技有限公司 | A kind of fluorenes simultaneously carbazole derivates, preparation method and application |
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2019
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Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000059884A1 (en) * | 1999-01-26 | 2000-10-12 | Dana-Farber Cancer Institute, Inc. | Pharmaceutically active compounds and methods of use thereof |
| US7365198B2 (en) * | 2006-03-02 | 2008-04-29 | Canon Kabushiki Kaisha | Silyl compound, light emitting material, and organic light emitting device using the same |
| KR20140141970A (en) * | 2013-06-03 | 2014-12-11 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| CN106554322A (en) * | 2015-09-30 | 2017-04-05 | 北京鼎材科技有限公司 | A kind of phenazene derivative and its application in organic electroluminescence device |
| CN109942541A (en) * | 2019-03-08 | 2019-06-28 | 武汉尚赛光电科技有限公司 | A kind of fluorenes and carbazole derivates and its preparation method and application |
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