CN103772291A - Aniline-containing organic semiconductor material and preparation method therefor and organic electroluminescent device - Google Patents
Aniline-containing organic semiconductor material and preparation method therefor and organic electroluminescent device Download PDFInfo
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- CN103772291A CN103772291A CN201210410061.6A CN201210410061A CN103772291A CN 103772291 A CN103772291 A CN 103772291A CN 201210410061 A CN201210410061 A CN 201210410061A CN 103772291 A CN103772291 A CN 103772291A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract
The invention provides an aniline-containing organic semiconductor material and a preparation method therefor and an organic electroluminescent device. The aniline-containing organic semiconductor material is the compound P with a structural formula shown in the specification, wherein R is hydrogen, methyl or ethyl. The compound P is prepared through a Suzuki coupling reaction. The aniline-containing organic semiconductor material comprises triphenylamine and pyrimidine groups, has good bipolar transmission performance and thermal stability, has excellent dissolving property and film forming property, and is helpful to prolong a service life of a luminescent device and raise device luminous efficiency.
Description
Technical field
The present invention relates to field of photovoltaic materials, particularly relate to a kind of organic semiconductor material containing aniline and preparation method thereof and organic electroluminescence device.
Background technology
Along with the development of information age, the organic EL display (OLEDs) of efficient, energy-conservation, lightweight and big area white-light illuminating more and more receive people's concern.OLED technology is paid close attention to by global scientist, and relevant enterprise and laboratory are all in the research and development of carrying out this technology.As a kind of novel LED technology, there is active illuminating and light, thin, good contrast, energy consumption organic electroluminescence device low, that can be made into the features such as flexible device has proposed higher requirement to organic semiconductor material.
1987, the Tang of Eastman Kodak company of the U.S. and VanSlyke reported the breakthrough in organic electroluminescent research, and will realize the application purposes such as panchromatic demonstration and illumination, and luminescent device must have certain efficiency and life-span.Current heat-staple blue light material lacks, and this has influence on life-span and the development thereof of white light parts.
Summary of the invention
The problem lacking for solving the organic electroluminescent blue light material of above-mentioned efficient stable, the present invention aims to provide a kind of organic semiconductor material containing aniline, this organic semiconductor material has good carrier transmission performance, there is higher thermostability simultaneously, be beneficial to the work-ing life that extends luminescent device.
The organic electroluminescence device that the present invention also provides the preparation method of this organic semiconductor material and contains this organic semiconductor material.
On the one hand, the invention provides a kind of organic semiconductor material containing aniline, the described organic semiconductor material containing aniline is the compound P shown in following structural formula:
Wherein, R is hydrogen, methyl or ethyl.
In the present invention, both contained trianilino group containing in the organic semiconductor material of aniline, contain again pyrimidine group, wherein, triphenylamine is a kind of electron rich group, and the organic semiconductor material that the existence of its group makes the present invention contain aniline has good hole transport performance, pyrimidine has good electronic transmission performance, these two kinds of groups are combined and can make material have bipolarity transmission performance, and its structure itself is the structure of a vertical structure of rotation simultaneously, makes material have certain thermostability.The present invention has good bipolarity transmission performance and thermostability containing the organic semiconductor material of aniline.
On the other hand, the invention provides the preparation method of the above-mentioned organic semiconductor material containing aniline, comprise the steps:
The compd A and the compd B that provide respectively following structural formula to represent:
Wherein, R is hydrogen, methyl or ethyl;
In anaerobic state and atmosphere of inert gases, described compd A, described compd B are mixed with organic catalyst, then add basic solution and organic solvent, Suzuki coupling reaction is carried out in heating, make the following organic semiconductor material containing aniline of structural formula, i.e. compound P
Wherein, R is hydrogen, methyl or ethyl.
Preferably, the mol ratio of described compd A and compd B is 1:2 ~ 1:3.
Preferably, described organic catalyst is tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
Preferably, the mol ratio of described organic catalyst and compd A is 0.001:1 ~ 0.1: 1.
Preferably, the temperature of reaction of described Suzuki coupling reaction is 75～120 ℃, and the reaction times is 24～48 hours.
Preferably, described basic solution is cesium carbonate (Cs
2cO
3) solution, salt of wormwood (K
2cO
3) solution or sodium carbonate (Na
2cO
3) solution; The mole dosage of described basic solution is 20～25 times of compd A mole dosage.
Preferably, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
Preferably, in described atmosphere of inert gases, gas is nitrogen or argon gas.
Preferably, the preparation method of the described organic semiconductor material (being compound P) containing aniline further comprises the step of separation and purification, the step of described separation and purification is as follows: the reaction solution of the organic semiconductor material containing aniline is poured in saturated aqueous ammonium chloride, with dichloromethane extraction, organic phase is washed with sodium chloride aqueous solution, dry, revolves to steam except after desolventizing to obtain crude product, subsequently crude product is carried out to silica gel column chromatography separating-purifying, obtain the organic semiconductor material that product contains aniline.
The third aspect, the invention provides a kind of organic electroluminescence device, comprises anode, functional layer, luminescent layer and negative electrode, and the material of described luminescent layer is the organic semiconductor material containing aniline shown in following structural formula, i.e. compound P:
Wherein, wherein, R is hydrogen, methyl or ethyl.
A kind of organic semiconductor material containing aniline provided by the invention and preparation method thereof and application, have following beneficial effect:
The invention provides a kind of organic semiconductor material containing aniline, in the structure of this organic semiconductor material, triphenylamine is electron rich group, form conjugated structure together with pyrimidine, make the organic semiconductor material containing aniline of the present invention there is good carrier transmission performance and thermostability, be beneficial to and extend the work-ing life of luminescent device and improve device luminous efficiency.
In addition, the organic semiconductor material containing aniline of the present invention has good solubility property and film forming properties in common solvent (as toluene, methylene dichloride, trichloromethane or tetrahydrofuran (THF)).
The present invention utilizes the organic semiconductor material of Suzuki reaction preparation containing aniline, and preparation method is simple and ripe, and productive rate is high, mild condition, and product is easy to control.
Accompanying drawing explanation
Fig. 1 is the structure iron of the organic electroluminescence device of the organic semiconductor material that contains aniline of Application Example.
Embodiment
The following stated is the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention; can also make some improvements and modifications, these improvements and modifications are also considered as protection scope of the present invention.
In following examples, compd A can reference literature (reference Advanced Materials, 2012,24(21): 2922 – 2928.) disclosed method is synthetic, and compd B can be bought (Taiwan Jiguang Technology Corporation) from the market.
Wherein, R is hydrogen, methyl or ethyl.
Embodiment mono-
A kind of organic semiconductor material 4,5 '-(3,3 '-(pentanoic) phenyl)-(2-phenyl pyrimidine) (called after TPAPPy) containing aniline, the compound P1 for shown in following structural formula:
The preparation method of the above-mentioned organic semiconductor material compound P1 containing aniline, comprises the steps:
(1) the bromo-2-of compd A 1(5-(4-bromophenyl) pyrimidine that provides respectively following structural formula to represent) and compd B (3-(pentanoic) phenyl-boron dihydroxide),
(2) by bromo-compd A 1(5-2-(4-bromophenyl) pyrimidine) 4.0mmol, compd B (3-(pentanoic) phenyl-boron dihydroxide) 8.0mmol, catalyzer tetrakis triphenylphosphine palladium 0.4mmol joins in reaction flask, vacuumize, after logical nitrogen circulation 3 times, make reaction system in anaerobic state, under nitrogen protection, add the Na of tetrahydrofuran solution 60mL, 2mol/L
2cO
3aqueous solution 40ml, mixed solution heating is carried out to Suzuki coupling reaction, 75 ℃ of back flow reaction 24h, make and contain the organic semiconductor material 4 of P1 containing aniline, 5 '-(3, 3 '-(pentanoic) phenyl)-the reaction solution of (2-phenyl pyrimidine), described reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain the solid product 4 after purifying, 5 '-(3, 3 '-(pentanoic) phenyl)-(2-phenyl pyrimidine) (TPAPPy).
In the present embodiment, 4,5 '-(3,3 '-(pentanoic) phenyl)-(2-phenyl pyrimidine) productive rate (TPAPPy) is 87%, and mass spectrometric measurement result is: MS:m/z 643 (M
+), results of elemental analyses is C, 85.91; H, 5.34; N, 8.76, corresponding molecular formula is C
46h
34n
4.By the molecular structure of mass spectrometric measurement, results of elemental analyses and reactant, confirm that product has described structure.
Embodiment bis-
A kind of organic semiconductor material 4,5 '-(3,3 '-(pentanoic) phenyl)-(2-(3-tolyl) pyrimidine) (called after TPAMPPy) containing aniline, the compound P2 for shown in following structural formula:
The preparation method of the above-mentioned organic semiconductor material compound P2 containing aniline, comprises the steps:
(1) the bromo-2-of compd A 2(5-(the bromo-3-tolyl of the 4-) pyrimidine that provides respectively following structural formula to represent) and compd B (3-(pentanoic) phenyl-boron dihydroxide),
(2) by bromo-compd A 2(5-2-(the bromo-3-tolyl of 4-) pyrimidine) 4.0mmol, compd B (3-(pentanoic) phenyl-boron dihydroxide) 8.5mmol, catalyzer three (dibenzalacetone) two palladium 0.004mmol join in reaction flask, vacuumize, after logical nitrogen circulation 3 times, make reaction system in anaerobic state, under nitrogen protection, add the K of glycol dimethyl ether 65mL, 2mol/L
2cO
3aqueous solution 45ml, mixed solution heating is carried out to Suzuki coupling reaction, 95 ℃ of back flow reaction 40h, make and contain the organic semiconductor material 4 of P2 containing aniline, 5 '-(3, 3 '-(pentanoic) phenyl)-the reaction solution of (2-(3-tolyl) pyrimidine), described reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain the solid product 4 after purifying, 5 '-(3, 3 '-(pentanoic) phenyl)-(2-(3-tolyl) pyrimidine) (TPAMPPy).
In the present embodiment, 4,5 '-(3,3 '-(pentanoic) phenyl)-(2-(3-tolyl) pyrimidine) productive rate (TPAMPPy) is 90%, and mass spectrometric measurement result is: MS:m/z 657 (M
+), results of elemental analyses is C, 85.99; H, 5.50; N, 8.51, corresponding molecular formula is C
47h
36n
4.By the molecular structure of mass spectrometric measurement, results of elemental analyses and reactant, confirm that product has described structure.
Embodiment tri-
A kind of organic semiconductor material 4,5 '-(3,3 '-(pentanoic) phenyl)-(2-(3-ethylbenzene) pyrimidine) (called after TPAEPPy) containing aniline, the compound P3 for shown in following structural formula:
The preparation method of the above-mentioned organic semiconductor material (being compound P3) containing aniline, comprises the steps:
(1) compound A-13 (the bromo-2-of 5-(the bromo-3-ethylbenzene of 4-) pyrimidine) and the compd B (3-(pentanoic) phenyl-boron dihydroxide) that provide respectively following structural formula to represent,
(2) by compound A-13 (the bromo-2-of 5-(the bromo-3-ethylbenzene of 4-) pyrimidine) 4.0mmol, compd B (3-(pentanoic) phenyl-boron dihydroxide) 12.0mmol, two (triphenylphosphine) palladium chloride 0.12mmol of catalyzer join in reaction flask, vacuumize, after logical nitrogen circulation 3 times, make reaction system in anaerobic state, under nitrogen protection, add the Cs of toluene solution 60mL, 2mol/L
2cO
3aqueous solution 50ml, mixed solution heating is carried out to Suzuki coupling reaction, 120 ℃ of back flow reaction 48h, make and contain the organic semiconductor material 4 of P3 containing aniline, 5 '-(3, 3 '-(pentanoic) phenyl)-the reaction solution of (2-(3-ethylbenzene) pyrimidine), described reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain the solid product 4 after purifying, 5 '-(3, 3 '-(pentanoic) phenyl)-(2-(3-ethylbenzene) pyrimidine) (TPAEPPy).
In the present embodiment, 4,5 '-(3,3 '-(pentanoic) phenyl)-(2-(3-ethylbenzene) pyrimidine) productive rate (TPAEPPy) is 92%, and mass spectrometric measurement result is: MS:m/z 610 (M
+).Results of elemental analyses is C, 85.90; H, 5.70; N, 8.37, corresponding molecular formula is C
48h
38n
4.By the molecular structure of mass spectrometric measurement, results of elemental analyses and reactant, confirm that product has described structure.Test implementation example
For supporting beneficial effect of the present invention, provide carrier transmission performance testing method and the data of the organic semiconductor material containing aniline of the present invention below.
By time of flight method (Time ofFlight, TOF), respectively 7.0 × 10
5vcm
-1with 4.0 × 10V
5cm
-1in electric field, test field-effect hole mobility and the electronic mobility of the organic semiconductor material containing aniline of the embodiment of the present invention one ~ tri-preparation, the results are shown in Table 1, wherein, P1 represents the organic semiconductor material containing aniline of preparation in embodiment mono-, be compound P1, by that analogy.
Field-effect hole mobility and the electronic mobility of table 1 organic semiconductor material containing aniline of the present invention
From table 1 data, strength of electric field is 7.0 × 10
5vcm
-1time, the hole mobility of the field-effect of the organic semiconductor material containing aniline prepared by the present invention is 8.4 × 10
-5cm
2(Vs)
-1above; Be 4.0 × 10 at electric field
5vcm
-1time, the electronic mobility of compound is 3.9 × 10
-6cm
2(Vs)
-1above, illustrate that the present invention has the performance of bipolarity transmission containing the organic semiconductor material of aniline.
Application Example
Containing the organic electroluminescence device containing the organic semiconductor material of aniline, is the electroluminescent device of the compound P2 for preparing of the application embodiment of the present invention two as luminescent layer material, and Fig. 1 is shown in by structure iron.General organic electroluminescence device comprises anode, functional layer, luminescent layer and negative electrode, and functional layer comprises hole injection layer, hole transmission layer, electron supplying layer and electron injecting layer, and luminescent layer is between hole transmission layer and electron supplying layer.
As shown in Figure 1, the organic electroluminescence device of the present embodiment is straticulate structure, comprise successively glass substrate 1, anode 2, hole transmission layer 3, blue light-emitting layer 4, hole blocking layer 5, electron transfer layer 6, buffer layer 7 and negative electrode 8, wherein, the material of luminescent layer 4 is P2 and two (4, 6-difluorophenyl pyridine-N, C2) pyridine carboxylic acid closes the mixing material of iridium (FIrpic), P2 is donor material, two (4, 6-difluorophenyl pyridine-N, C2) to close iridium be acceptor material to pyridine carboxylic acid, two (4, 6-difluorophenyl pyridine-N, C2) to close the massfraction of iridium in mixing material be 10% to pyridine carboxylic acid, except glass substrate, 2 ~ 8 material is followed successively by: ITO/NPB/P2:FIrpic/BCP/Alq
3/ LiF/Al, the organic semiconductor material compound P2 structural formula containing aniline prepared by embodiment 2 is:
In addition, the material of anode 2 is preferably the ITO(tin indium oxide that square resistance is 10-20 Ω/mouth), thickness is 150nm, the material of hole transmission layer 3 is NPB, i.e. N, N '-bis-(Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines, thickness is 40nm, the material of hole blocking layer 5 is BCP, 2, and 9-dimethyl-4,7-phenylbenzene-9,10-phenanthroline, thickness is 10nm, the material of electron transfer layer 6 is Alq
3, i.e. three (oxine) aluminium, thickness is 40nm, the material of buffer layer 7 is LiF, i.e. lithium fluoride, thickness is 1nm, and the material of negative electrode 8 is aluminium, and thickness is 120nm.
Above-mentioned organic electroluminescence device adopts the method preparation of vacuum evaporation, first evaporation anode 2 on glass substrate 1, then evaporation hole transmission layer 3 successively, blue light-emitting layer 4, hole blocking layer 5, electron transfer layer 6, buffer layer 7, last evaporation negative electrode 8, obtains organic electroluminescence device, and each layer can adopt existing method to form.
Under room temperature, atmospheric environment, test, this blue light OLED device has been obtained the maximum light efficiency of 19.3lm/W, has higher luminous efficiency, can be widely used in the luminous field such as blueness or white.
The above is the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention; can also make some improvements and modifications, these improvements and modifications are also considered as protection scope of the present invention.
Claims (10)
1. containing an organic semiconductor material for aniline, it is characterized in that the compound P for shown in following structural formula:
Wherein, R is hydrogen, methyl or ethyl.
2. containing a preparation method for the organic semiconductor material of aniline, it is characterized in that comprising the steps: the compd A and the compd B that provide respectively following structural formula to represent:
Wherein, R is hydrogen, methyl or ethyl;
In anaerobic state and atmosphere of inert gases, described compd A, described compd B are mixed with organic catalyst, then add basic solution and organic solvent, Suzuki coupling reaction is carried out in heating, make the following organic semiconductor material containing aniline of structural formula, i.e. compound P
Wherein, R is hydrogen, methyl or ethyl.
3. the preparation method of the organic semiconductor material containing aniline as claimed in claim 2, is characterized in that, the mol ratio of described compd A and compd B is 1:2 ~ 1:3.
4. the preparation method of the organic semiconductor material containing aniline as claimed in claim 2, it is characterized in that, described organic catalyst is tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
5. the preparation method of the organic semiconductor material containing aniline as claimed in claim 4, is characterized in that, the mol ratio of described organic catalyst and compd A is 0.001:1 ~ 0.1: 1.
6. the preparation method of the organic semiconductor material containing aniline as claimed in claim 2, is characterized in that, the temperature of reaction of described Suzuki coupling reaction is 75～120 ℃, and the reaction times is 24～48 hours.
7. the preparation method of the organic semiconductor material containing aniline as claimed in claim 2, is characterized in that, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
8. the preparation method of the organic semiconductor material containing aniline as claimed in claim 2, it is characterized in that, described basic solution is cesium carbonate solution, solution of potassium carbonate or sodium carbonate solution, and described basic solution mole dosage is 20～25 times of compd A mole dosage.
9. the preparation method of the organic semiconductor material containing aniline as claimed in claim 2, is characterized in that, the gas in atmosphere of inert gases is nitrogen or argon gas.
10. an organic electroluminescence device, comprises anode, functional layer, luminescent layer and negative electrode successively, it is characterized in that, the material of described luminescent layer is the organic semiconductor material containing aniline shown in following structural formula claimed in claim 1, i.e. compound P:
Wherein, R is hydrogen, methyl or ethyl.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016091887A3 (en) * | 2014-12-09 | 2017-05-11 | Cynora Gmbh | Ambipolar host materials and use thereof |
| CN112876368A (en) * | 2021-02-19 | 2021-06-01 | 复旦大学 | Diphenylamine organic neutral radical electroluminescent material and preparation and application thereof |
-
2012
- 2012-10-24 CN CN201210410061.6A patent/CN103772291A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016091887A3 (en) * | 2014-12-09 | 2017-05-11 | Cynora Gmbh | Ambipolar host materials and use thereof |
| CN112876368A (en) * | 2021-02-19 | 2021-06-01 | 复旦大学 | Diphenylamine organic neutral radical electroluminescent material and preparation and application thereof |
| CN112876368B (en) * | 2021-02-19 | 2022-08-23 | 复旦大学 | Diphenylamine organic neutral radical electroluminescent material and preparation and application thereof |
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Application publication date: 20140507 |