CN105368445B - A kind of electroluminescent organic material and preparation method thereof - Google Patents
A kind of electroluminescent organic material and preparation method thereof Download PDFInfo
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- CN105368445B CN105368445B CN201510746404.XA CN201510746404A CN105368445B CN 105368445 B CN105368445 B CN 105368445B CN 201510746404 A CN201510746404 A CN 201510746404A CN 105368445 B CN105368445 B CN 105368445B
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Abstract
The invention discloses a kind of electroluminescent organic material, with structure as shown below：
Description
Technical field
The invention belongs to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field, more particularly, to electroluminescent organic material and its preparation
Methods and applications.
Background technology
Organic Light Emitting Diode（OLED）It is that Deng Qingyun of Kodak in 1987 et al. uses multi-layer film structure, just first
The Display Technique of the high-quantum efficiency, high-luminous-efficiency, high brightness and the low driving voltage that work out, this breakthrough makes
OLED turns into the focus of luminescent device research.Compared with traditional luminous and Display Technique, OLED has that driving voltage is low, body
The advantages of product is small, lightweight, material category is abundant, and easily realize large area preparation, wet method preparation and flexible device
Prepare.But, organic electroluminescence device is still present short life, the low problems of luminous efficiency, and awaiting us is carried out
It is further to explore.
Organic Light Emitting Diode（OLED the luminous organic material for) using is divided into two kinds：A kind of is small point of dyestuff and pigment
Sub- material, another kind is conjugacy macromolecular material.The OLED of small molecule structure respectively has with macromolecule OLED in material property
An eternal lasting, but with prior art development from the point of view of, such as the reliability of monitor, electrical characteristic and production stability on from the point of view of, it is small
Molecule OLEDs maintain the leading position, the OLED components of current input volume production, are entirely to use small molecule luminous organic material.
Hole-transporting type material of main part is mainly the injection and transmission balance for improving device hole, improves the luminous effect of device
Rate and life-span, as hole transmission layer, it is necessary to which meeting has the spies such as good mobility, heat endurance, suitable HUMO energy levels
Point.Although existing various hole mobile materials newly developed are applied to electroluminescent device, can simultaneously have electronics high concurrently and move
The hole mobile material of shifting rate and high stability is also rare.
The content of the invention
It is an object of the invention to improve the deficiency of prior art and providing a kind of can be effectively improved having for device efficiency
Electroluminescent material and preparation method.
The object of the present invention is achieved like this, a kind of above-mentioned electroluminescent organic material, and its feature is that this above-mentioned has
Electroluminescent material has structure as shown below：
。
The preparation method of above-mentioned electroluminescent organic material, is characterized in：By the dibenzothiophenes tetraphenyl with alkoxy
Silicon bromo-derivative and pyridine -4- boric acid, with 1mol：The ratio of 1.0 ~ 3.0mol is added in reaction system；Add catalytic amount
The palladium catalyst and PSQ silicon substrate co-catalysts of organic microporous polymer load；Potassium carbonate or sodium carbonate and mixed solvent are added, in
5 ~ 10h is reacted under the conditions of 50 ~ 100 DEG C, the derivative of silicon tetraphenyl and dibenzothiophenes is obtained, mixed solvent is toluene+ethanol
System or THF+ aqueous systems, syntheti c route are as follows：
。
Application of the above-mentioned electroluminescent organic material in new energy field.
Application of the above-mentioned electroluminescent organic material in OLED fields.
Design of the invention is the silicon tetraphenyl alkane derivatives according in OLED the characteristics of hole-transporting type material of main part
It is inertia material of main part that a class has energy gap high, this is because its Si atom is with sp3Hydridization, has effectively blocked being total to for intramolecular
Yoke, so that with energy gap and triplet higher wider, but the mobility ratio with carrier is relatively low, heat endurance
Poor the shortcomings of.The present invention is exactly with silicon tetraphenyl as agent structure, in order to preferably adjust HOMO energy levels, in dibenzo thiophene
The alkoxy with electron donation is introduced in fen, improves the HOMO energy levels of material, improve its heat endurance and with higher
Triplet introduce the pyridine ring of strong electrophilicity due to and the periphery of molecule, electron injection/transmittability is obtained
It is greatly enhanced.NPB is one of hole mobile material for being widely used always, Tg=98 DEG C of its glass transition temperature, Tm=290
DEG C, mobility is 5.1 × 10-4cm2/ Vs, in order to improve the heat endurance of molecule, this patent have devised with silicon tetraphenyl and
The derivative of dibenzothiophenes.
Beneficial effects of the present invention are as follows：
1. the present invention is using dibenzothiophenes of the silicon tetraphenyl group connection with cavity transmission ability and carries alkoxy
Side chain, it is possible to reduce intermolecular reunion and interaction.
2. the present invention introduces strong electrophilicity and the pyridine with electronic transmission structures on the body construction, and electron injection/
Transmittability is greatly improved.
3. the present invention has preferable heat endurance, and wherein decomposition temperature is 449 DEG C, and glass transition temperature is 129 DEG C.
4. branched amoxy functional group of dibenzothiophenes institute in the present invention, carbon number is odd number, is contained than adjacent
The stability of even-numbered carbon atom is high, stronger than the structure electron donation with even-numbered carbon atom, but if carbon number is long again
If, intermolecular interaction can be hindered, it is impossible to closely effectively pile up.
5. the present invention as OLED hole-transporting type material of main part, with Ir（ppy）3As guest materials, device
Maximum current efficiency, power efficiency and external quantum efficiency are respectively is 88.2cd/A, 80.1Im/W, 29%；In high electric field（1×
106V/cm）When mobility be 2 × 10-5cm-2/ Vs, shows that the derivative has electron mobility.
Compound see the table below with NPB correction datas in the present invention：
| Compound name | Molecular weight | Fusing point/DEG C | Glass transition temperature/DEG C | |
| NPB | 589 | 290 | 98 | |
| Ⅶ | 768 | 321 | 129 |
As shown by data, hole-transporting type material of main part of the invention has excellent hole transport performance, while having electronics
Transmission characteristic, can be used for OLED and shows.
Specific embodiment
The present invention is further described with reference to embodiments, it is necessary to explanation is following embodiment only for clearly
The present invention is understood, the invention is not restricted to the embodiment.
Properties of product test event and tester：
Thermogravimetric analysis is tested by Oniversal V2.4F TA Instruments types thermogravimetric analyzer, and DSC is by TA DSC
Q20 type differential scannings instrument is determined.
Absorption spectrum is determined by UV-4802 type dual-beams ultraviolet-uisible spectrophotometer, and fluorescence spectrum and fluorescent quantum are imitated
Rate is by 970CRT fluorescence spectrophotometer measurements.
The measurement of fluorescence quantum efficiency using PBD as standard substance, its Ф=1.0, fluorescence quantum efficiency is according to following public affairs
Formula is calculated：Ф v=(As/Au) Ф s, wherein As, Au distinguish the integral area of determinand and reference material emission spectrum, and Ф s are
The luminous efficiency of reference material.
Japanese Shimadzu LC-10ATvp types high pressure liquid chromatograph (methyl alcohol：Acetonitrile=2：1, flow velocity 1ml/min)；Day island proper
Tianjin GC-14C, GC-17A gas chromatograph（DB-1 type pillars）；Japanese Shimadzu GCMS-2014C type mass spectrographs.
A kind of embodiment 1, electroluminescent organic material, material has structure as shown below：
,
The material has hole transporting properties, can be used for OLED and shows.
The syntheti c route of above-mentioned material is as follows：
The wherein preparation of chemical compounds I：
It is cold to Isosorbide-5-Nitrae-'-dibromobiphenyl 14.87g, tetrahydrofuran 210 mL is sequentially added in there-necked flask under argon gas protection
But to -78 DEG C, 26.25 mL n-BuLis are added dropwise, completion of dropping is stirred 1 hour, then 7.59 g are slowly added dropwise at -78 DEG C
Dichloro base silane, completion of dropping insulation reaction automatic heating after 1 hour, reaction is overnight.Add water and reaction is quenched, boil off molten
Agent, adds dichloromethane and water dissolves residue, and washing separates organic layer, and organic layer adds water washing twice to neutral, organic layer
With anhydrous sodium sulfate drying, methylene chloride is steamed, through column chromatography for separation, leacheate is petroleum ether to residue：Chloroform=
35:1 (V/V), boils off solvent, after drying, obtains 11.0 g white crystalline powders, and yield is 74.2%.
The preparation of compound ii：
20 ~ 30 are cooled to addition dichloromethane 200ml, alchlor 32.0g, dibenzothiophenes 18.4g in reaction bulb,
After stirring 10min, start that chloroacetic chloride 17.27g is added dropwise, process temperature control is added dropwise, completion of dropping reaction 2h is added in reaction system
10% hydrochloric acid 200ml, stirring reaction 2h, are stood, and separate organic phase, and organic phase is washed with water three times to neutrality, and anhydrous magnesium sulfate is done
Dry, filtering, concentration filtrate obtains crude product 28.0g to solvent is not gone out, and crude product obtains II 20.1g through recrystallizing methanol, and yield is 75%.
The preparation of compound III：
To glacial acetic acid 200ml, II product 13.4g, ammonium persulfate 31.9g is added in there-necked flask, 0.5h is stirred, then stirred
Concentrated sulfuric acid 23.5g is added dropwise to system under state, completion of dropping continues to react 10h, and filtering reacting liquid obtains crude product 11.0g, ethanol weight
Crystallization obtains III 9.19g, and yield is 85%.
The preparation of compounds Ⅳ：
To pyridine 250ml, III 21.6g, stirring and dissolving is sequentially added in there-necked flask, bromo pentane silane 33.23g is added dropwise, then returns
Stream reaction 3h, system cooling, filtering concentrates filtrate, obtains product 29.3g, and IV 25.3g is obtained with recrystallisation from isopropanol, and yield is
71%。
The preparation of compound V：
Under argon gas protection, to IV 53.5g, tetrahydrofuran 100ml is sequentially added in there-necked flask, -78 DEG C are cooled to, be added dropwise
112.5mL n-BuLis, completion of dropping is stirred 1 hour at -78 DEG C, then butyl borate 62.14g, completion of dropping is slowly added dropwise
Insulation reaction automatic heating after 1 hour, reaction is overnight.Water 300ml, concentrated hydrochloric acid 300ml, petroleum ether are added in reaction bulb
300ml, stirring 2h.Organic layer washing boils off solvent twice to neutral, by product under stirring, is poured slowly into water, analyses
Go out solid, filter, drying obtains V 33.0g after filter cake petroleum ether wash-out.Yield is 55%.
The preparation of compound VI：
To adding two in there-necked flask（4- bromophenyls）- diphenyl silane 9.9 g, V 8.0 g, polymer support load
Pd catalyst 0.1mol%, PSQ type silicon substrate co-catalyst 0.05mol%, the g of Anhydrous potassium carbonate 2.76, the mL of tetrahydrofuran 50,
The mL of water 50, under argon gas protection, 70 DEG C of stirring reactions 2 hours, reaction is finished.Solvent is boiled off, with dichloromethane and water-soluble
Solution residue, washing separates organic layer, and organic layer 100mL is washed twice to neutrality, and after boiling off solvent, toluene wash-out is done
9.0 g white powders are obtained after dry, yield is 59%.
The preparation of compound VII：
To addition VI 15.40 g, the g of pyridine -4- boric acid 2.46, polymer support Pt-supported catalyst in there-necked flask
0.1mol%, PSQ type silicon substrate co-catalyst 0.05mol%, the g of Anhydrous potassium carbonate 2.76, the mL of tetrahydrofuran 50, water 50 mL, 70
DEG C stirring reaction 8 hours, with 100 mL dichloromethane and 100 mL water dissolves residues, washing separates organic layer, has
Machine layer is washed with water twice to neutrality, and after boiling off solvent, ethanol elution obtains white powder 10.44g after drying, and yield is 68%.
A kind of embodiment 2, electroluminescent organic material, material has structure as shown below：
,
The derivative has hole transporting properties, can be used for OLED and shows.
The syntheti c route of said derivative is as follows：
The wherein preparation of chemical compounds I：
It is cold to Isosorbide-5-Nitrae-'-dibromobiphenyl 37.17g, tetrahydrofuran 630 mL is sequentially added in there-necked flask under argon gas protection
But to -78 DEG C, 78.76 mL n-BuLis are added dropwise, completion of dropping is stirred 1 hour, then 19.0 g are slowly added dropwise at -78 DEG C
Dichloro base silane, completion of dropping insulation reaction automatic heating after 1 hour, reaction is overnight.Add water and reaction is quenched, boil off molten
Agent, adds dichloromethane and water dissolves residue, and washing separates organic layer, and organic layer adds water washing twice to neutral, organic layer
With anhydrous sodium sulfate drying, methylene chloride is steamed, through column chromatography for separation, leacheate is petroleum ether to residue：Chloroform=
35:1 (V/V), boils off solvent, after drying, obtains 26.7 g white crystalline powders, and yield is 72%.
The preparation of compound ii：
To adding dichloromethane 500ml, alchlor 80.0g, dibenzothiophenes 46g to be cooled to 20 ~ 30 in reaction bulb, stir
After mixing 10min, start that chloroacetic chloride 43.17g is added dropwise, process temperature control is added dropwise, completion of dropping reaction 2h is added in reaction system
10% hydrochloric acid 500ml, stirring reaction 2h, are stood, and separate organic phase, and organic phase is washed with water three times to neutrality, and anhydrous magnesium sulfate is done
Dry, filtering, concentration filtrate obtains crude product 70.0g to solvent is not gone out, and crude product obtains II 51.59g through recrystallizing methanol, and yield is
77%。
The preparation of compound III：
To glacial acetic acid 600ml, II product 40.2g, ammonium persulfate 95.7g is added in there-necked flask, 0.5h is stirred, then stirred
Concentrated sulfuric acid 70.5g is added dropwise to system under state, completion of dropping continues to react 10h, and filtering reacting liquid obtains crude product 35.0g, ethanol weight
Crystallization obtains III 26.9g, and yield is 83%.
The preparation of compounds Ⅳ：
To pyridine 750ml, III 64.8g, stirring and dissolving is sequentially added in there-necked flask, bromo pentane silane 99.7g is added dropwise, is then refluxed for
Reaction 3h, system cooling, filtering concentrates filtrate, obtains product 87.9g, and IV 78.0g is obtained with recrystallisation from isopropanol, and yield is
73%。
The preparation of compound V：
Under argon gas protection, to IV 64.2g, tetrahydrofuran 150ml is sequentially added in there-necked flask, -78 DEG C are cooled to, be added dropwise
135mL n-BuLis, completion of dropping is stirred 1 hour at -78 DEG C, then butyl borate 74.57g, completion of dropping is slowly added dropwise
Insulation reaction automatic heating after 1 hour, reaction is overnight.Water 400ml, concentrated hydrochloric acid 400ml, petroleum ether are added in reaction bulb
500ml, stirring 2h.Organic layer washing boils off solvent twice to neutral, by product under stirring, is poured slowly into water, analyses
Go out solid, filter, drying obtains V 43.2.0g after filter cake petroleum ether wash-out.Yield is 60%.
The preparation of compound VI：
To adding two in there-necked flask（4- bromophenyls）The g of-diphenyl silane 14.58, V 12.0 g, polymer support is born
Carry Pd catalyst 0.1mol%, PSQ type silicon substrate co-catalyst 0.05mol%, the g of Anhydrous potassium carbonate 4.14, tetrahydrofuran 75
ML, the mL of water 75, under argon gas protection, 70 DEG C of stirring reactions 2 hours, reaction is finished.Solvent is boiled off, with dichloromethane and water
Dissolution residual substance, washing separates organic layer, and organic layer 150mL is washed twice to neutrality, after boiling off solvent, toluene wash-out,
14.19 g white powders are obtained after drying, yield is 62%.
The preparation of compound VII：
To addition VI 24.64 g, the g of pyridine -4- boric acid 3.94, polymer support Pt-supported catalyst in there-necked flask
0.1mol%, PSQ type silicon substrate co-catalyst 0.05mol%, the g of Anhydrous potassium carbonate 4.42, the mL of tetrahydrofuran 100, the mL of water 100,
70 DEG C of stirring reactions 8 hours, with 200 mL dichloromethane and 200 mL water dissolves residues, washing separates organic layer,
Organic layer is washed with water twice to neutrality, and after boiling off solvent, ethanol elution obtains white powder 11.7g after drying, and yield is 70%.
Compound VII：H NMR (400 MHz, CDCl3) δ=8.69 (dd, J=4.5：1.6 Hz, 2H, Ar-H)： 8.24–
8.10 (m, 2H, Ar-H), 7.89-7.73 (m, 7H, Ar-H), 7.74-7.62 (m, 6H, Ar-H), 7.62-7.40
(m, 12H, Ar-H), 3.94（M, 4H, OCH2-H）, 1.29-1.71（M, 12H, CH2-H）, 0.96 (m, 6H, Me-H）；LC-
MS （ESI）：767 [M-H]-, elementary analysis measured value（Calculated value）/%：C79.75（79.01）, H6.43（5.47）, N1.82
（2.03）, O4.17（4.70）, S4.17（4.70）, Si3.66（4.10）.
Fusing point：321 DEG C, glass transition temperature：129 DEG C, decomposition temperature：449℃
Absorption spectrum：λmax=299nm
Fluorescence spectrum：λmax=395nm
Hole mobility：4.9×10--3 cm-2/Vs
Identification confirms that the compound of synthesis is 4-（4-{[4-（The amoxys of 2,8- bis-）Dibenzo [b, d] thienyl] phenyl two
Phenyl silicon substrate } phenyl）Pyridine.
Claims (4)
1. a kind of electroluminescent organic material, it is characterized in that the electroluminescent organic material has structure as shown below：
,
The material has hole transporting properties, can be used for OLED and shows.
2. the preparation method of the electroluminescent organic material described in a kind of claim 1, it is characterized in that：By the hexichol with alkoxy
Bithiophene silicon tetraphenyl bromo-derivative and pyridine -4- boric acid, with 1mol：The ratio of 1.0 ~ 3.0mol is added in reaction system；Plus
Enter the palladium catalyst and PSQ silicon substrate co-catalysts of organic microporous polymer load of catalytic amount；Add potassium carbonate or sodium carbonate
And mixed solvent, 5 ~ 10h is reacted under the conditions of 50 ~ 100 DEG C, the derivative of silicon tetraphenyl and dibenzothiophenes is obtained, mix molten
Agent is toluene+ethanol system or THF+ aqueous systems.
3. application of a kind of electroluminescent organic material described in claim 1 in new energy field.
4. application of a kind of electroluminescent organic material described in claim 1 in OLED fields.
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| US8563145B2 (en) * | 2006-06-02 | 2013-10-22 | Idemitsu Kosan Co., Ltd. | Material containing two or three dibenzofuran groups, dibenzothiophene groups, or a combination thereof, which is operable for organic electroluminescence elements, and organic electroluminescence elements using the material |
| US8748012B2 (en) * | 2011-05-25 | 2014-06-10 | Universal Display Corporation | Host materials for OLED |
| CN102391301B (en) * | 2011-09-07 | 2014-02-05 | 武汉大学 | Phosphorescent main body material |
| JP2015117210A (en) * | 2013-12-19 | 2015-06-25 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Silane compound and organic el element |
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