CN106349106B - A kind of organic photoelectrical material and the organic electroluminescence device comprising the material - Google Patents

A kind of organic photoelectrical material and the organic electroluminescence device comprising the material Download PDF

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CN106349106B
CN106349106B CN201610711611.6A CN201610711611A CN106349106B CN 106349106 B CN106349106 B CN 106349106B CN 201610711611 A CN201610711611 A CN 201610711611A CN 106349106 B CN106349106 B CN 106349106B
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compound
electroluminescence device
luminescent
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CN106349106A (en
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高自良
张成新
冯鑫
石宇
王元贵
王新涛
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Valiant Co Ltd
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Abstract

The present invention relates to a kind of organic photoelectrical material, it is characterised in that aryl is introduced centered on anthraquinone ring, and at 2 of anthraquinone ring and 6, shown in the general structure such as formula (I) of the organic photoelectrical material：Wherein, Ar1And Ar2It independently is the aryl containing substituent or without substituent.The invention further relates to the preparation method of above-mentioned organic photoelectrical material.The invention further relates to the organic electroluminescence device that the organic photoelectrical material has been used in luminescent layer.The present invention by the organic photoelectrical material and BEP prepares luminescent layer so that prepared OLED luminescent devices open bright voltage and high-high brightness all obtains vast improvement, there is good application effect, there is good industrialization prospect.

Description

A kind of organic photoelectrical material and the organic electroluminescence device comprising the material
Technical field
The present invention relates to materials science field, more specifically it relates to a kind of organic photoelectrical material and include the material Organic electroluminescence device.
Background technology
Organic electroluminescent diode (OLED) results from the eighties in last century, and organic light emitting diode (OLED) has certainly Luminous, wide viewing angle, fast response time, many advantages, such as Flexible Displays can be achieved, by the development of more than two decades, the technology by Step moves to maturity, and at present, organic electroluminescent technology, is mainly used in two fields, respectively full-color display and white light Illumination, based on the commodity of OLED Display Techniques, has been done step-by-step industrialization, such as, in commodity such as smart mobile phone, curved surface TVs In, this technology is applied widely.
In order to realize full-color display, the luminescent device of three kinds of colors of red, green, blue is respectively necessary for, with red device and green glow Device is compared, and blue luminescent device is still not mature enough, and device lifetime and efficiency are relatively low.People pass through ultra clean technology, encapsulate skill Art, there is blue light material of high glass-transition temperature etc. to improve the life-span of blue-light device for exploitation, and doping techniques and exploitation New material with the two poles of the earth structure, then it is the direction for improving device efficiency.
Doping techniques be by the way that luminescent material (guest materials) is dispersed in into other materials (material of main part) among, to reduce The concentration of luminescent material, so as to avoid intermolecular aggregation and concentration quenching, and then realize and improve device efficiency, improve electroluminescent Excitation, extend the purpose of device lifetime.
The content of the invention
To solve above technical problem, the invention provides a kind of organic photoelectrical material, its centered on anthraquinone ring, and 2 of the anthraquinone ring and 6 introducing aryl, shown in the general structure such as formula (I) of the organic photoelectrical material：
Wherein, Ar1And Ar2It independently is the aryl containing substituent or without substituent.
Preferably, the Ar1And Ar2Molecular weight independently between 60-500.
Preferably, the Ar1And Ar2Independently selected from the phenyl containing substituent or without substituent, naphthyl, phenanthryl, anthracene Base, fluoranthene base, fluorenyl, pyrenyl, Sanya phenyl, dibenzofuran group, dibenzothiophenes base, carbazyl, N- substituted carbazole bases.
Preferably, the structural formula of the organic photoelectrical material is：
Present invention also offers a kind of preparation method of above-mentioned organic photoelectrical material, comprise the following steps：
1) based on 2,6- dibromo-anthraquinones, synthetic intermediate 1, reaction equation is as follows：
2) compound 1 is synthesized with the intermediate 1, reaction equation is as follows：
3) it is raw material with the compound 1, carries out fork coupling reaction with the aromatic compounds of boronate substitution, obtain described Luminous organic material.
Present invention also offers a kind of organic electroluminescence device, and it includes luminescent layer, and the luminescent layer is by above-mentioned luminous Material and BEP compositions.
Preferably, the luminescent material and the BEP mass ratio are 9:1.
Preferably, the organic electroluminescence device is passed by ITO Conducting Glass, hole transmission layer, luminescent layer, electronics Defeated layer, electron injecting layer and cathode layer, which stack gradually, to be formed.Wherein, hole transmission layer is made up of NPB, and electron transfer layer is by TPBI It is made, electron injecting layer is made up of lithium fluoride, and cathode layer is made of aluminum.
Brief description of the drawings
Fig. 1 is the Rotating fields schematic diagram of the electroluminescent device of the present invention.
101st, ITO Conducting Glass, 102, hole transmission layer, 103, luminescent layer, 104, electron transfer layer, 105, electronics Implanted layer, 106 cathode layers.
Embodiment
The principle and feature of the present invention are described below in conjunction with accompanying drawing and example, example is served only for explaining this hair It is bright, it is not intended to limit the scope of the present invention.
COMPOUNDS EXAMPLE
1. the preparation of compound 1：
1) intermediate 1 is prepared
Add 2,6- dibromo-anthraquinones (73.2g, 0.20mol) in 1L three-necked flasks, ethylene glycol (14.9g, 0.24mol), 2.5g p-methyl benzenesulfonic acid, 400mL dimethylbenzene, is heated to reflux, and fraction water device water-dividing flows back 12 hours.After reaction terminates, washing, divide Liquid, organic phase removed under reduced pressure solvent, column chromatography, toluene pet ether recrystallization, obtain white solid intermediate 1, HPLC purity 99.6%, yield 68.63%, MS (m/s)：407.9.
2) prepare compound 1
The preparation of intermediate 2：In the 1L there-necked flasks equipped with constant pressure funnel, addition magnesium metal (5.1g, 0.21mol), bromobenzene (31.4g, 0.20mol) is dissolved in 200g tetrahydrofurans, be placed in constant pressure funnel, used Nitrogen is protected, and is heated temperature in there-necked flask to bottle and is reached 65 DEG C, the tetrahydrofuran to bromo-iodobenzene is added by constant pressure funnel Solution, 50mL being firstly added, after question response triggers, slowly instills remainder, 1h is added dropwise, and reacts 2h under reflux temperature, Be down to after room temperature be transferred to it is stand-by in constant pressure funnel.Intermediate 1 (82.0g, 0.20mol) is dissolved among 200g tetrahydrofurans It is added in 2L there-necked flasks, above-mentioned stand-by solution is then slowly added dropwise, 3h is reacted under reflux temperature, after reaction terminates, is cooled to 25 DEG C, above reaction solution is slowly poured into the watery hydrochloric acid that 200g mass concentrations are 10%, stirs 15min, liquid separation, collect organic Phase, decompression slough solvent, obtain thick liquid, without refining, are directly used in reacting in next step.
250g benzene is added into above-mentioned gained thick liquid, it is molten to stir lower addition 1.42g (0.01mol) BFEE Liquid, 60~65 DEG C of reaction 4h, is quenched reaction, removed under reduced pressure solvent, column chromatography obtains intermediate 2, HPLC purity 99.6%, yield 45.88%, MS (m/s)：546.0.
The preparation of intermediate 3：Above intermediate 2 (54.8g, 0.1mol) is collected, adds 250mL toluene and 50mL 85% Formic acid, be warming up to backflow, insulation reaction 10 hours.Liquid separation, washing, organic phase removed under reduced pressure solvent, column chromatography, obtains white Solid is intermediate 3, HPLC purity 99.6%, yield 85.22%, MS (m/s)：502.0.
The preparation of compound 1：In 1L there-necked flasks, under nitrogen protection, intermediate 3 (40.3g, 0.08mol) is added, the third two Nitrile (6.6g, 0.10mol), 500mL anhydrous methylene chlorides, ice bath are cooled to interior 0-5 DEG C of temperature, slowly instill 22mL (0.20mol) Titanium tetrachloride, it is added dropwise within about 0.5 hour, is slowly dropped into 70mL pyridines, is added dropwise within about 1.0 hours, is added dropwise and removes ice Bath, 20-25 DEG C of stirring reaction of nitrogen protection lower room temperature 24 hours.Above reaction solution is slowly poured into 300g mass concentrations as 10% Watery hydrochloric acid in, stir 10min, liquid separation, collect organic phase, decompression sloughs solvent, obtains yellow solid, after glacial acetic acid recrystallization Obtained yellow solid i.e. compound 1, HPLC purity 99.5%, yield 73.58%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C29H16Br2N2, theoretical value 549.9680, test value, 549.9683.Elementary analysis (C29H16Br2N2), theoretical value C：63.07 H：2.92 N：5.07, measured value C：63.08 H： 2.94 N：5.05.
The compound C01 of embodiment 1 preparation
In 250mL there-necked flasks, addition compound 1 (2.76g, 0.005mol), phenyl boric acid (1.34g, 0.011mol), K2CO3(2.07g, 0.015mol), toluene (60mL), deionized water (20mL), N2Protection, add Pd (PPh3)4(17 5mg), rise Temperature is reacted 10 hours to flowing back, stops reacting, and is cooled, and liquid separation, 50mL deionizations are washed 1 time, is collected organic phase, is sloughed solvent, institute Obtain crude product to purify using silica gel column chromatography, obtain object C01, HPLC purity 99.8%, yield 84.55%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H26N2, theoretical value 546.2096, test value 546.2092.Elementary analysis (C41H26N2), theoretical value C：90.08 H：4.80 N：5.12, measured value C：90.05 H：4.82 N：5.13.
The compound C02 of embodiment 2 preparation
With embodiment 1, difference is to use raw material 1- naphthalene boronic acids alternative embodiment 1 compound C02 preparation method In phenyl boric acid.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C49H30N2, theoretical value 646.2409, test value 646.2403.Elementary analysis (C49H30N2), theoretical value C：90.99 H：4.68 N：4.33, measured value C：90.96 H：4.67 N：4.37.
The compound C04 of embodiment 3 preparation
With embodiment 1, difference is to use raw material 4- biphenylboronic acid alternative embodiments compound C04 preparation method Phenyl boric acid in 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H34N2, theoretical value 698.2722, test value 698.2726.Elementary analysis (C53H34N2), theoretical value C：91.09 H：4.90 N：4.01, measured value C：91.11 H：4.88 N：4.01.
The compound C07 of embodiment 4 preparation
With embodiment 1, difference is to use raw material 9- phenanthrene boric acid alternative embodiment 1 compound C07 preparation method In phenyl boric acid.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C57H34N2, theoretical value 746.2722, test value 746.2725.Elementary analysis (C57H34N2), theoretical value C：91.66 H：4.59 N：3.75, measured value C：91.68 H：4.58 N：3.74.
The compound C08 of embodiment 5 preparation
With embodiment 1, difference is to use raw material 9- anthracene boric acid alternative embodiment 1 compound C08 preparation method In phenyl boric acid.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C57H34N2, theoretical value 746.2722, test value 746.2728.Elementary analysis (C57H34N2), theoretical value C：91.66 H：4.59 N：3.75, measured value C：91.67 H：4.57 N：3.76.
The compound C09 of embodiment 6 preparation
With embodiment 1, difference is to replace using raw material 10- phenylanthracene -9- boric acid compound C09 preparation method Phenyl boric acid in embodiment 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C69H42N2, theoretical value 898.3348, test value 898.3345.Elementary analysis (C69H42N2), theoretical value C：92.18 H：4.71 N：3.11, measured value C：92.16 H：4.73 N：3.11.
The compound C10 of embodiment 7 preparation
With embodiment 1, difference is to replace using raw material fluoranthene -3- boric acid to be implemented compound C10 preparation method Phenyl boric acid in example 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C61H34N2, theoretical value 794.2722, test value 794.2723.Elementary analysis (C61H34N2), theoretical value C：92.16 H：4.32 N：3.52, measured value C：92.14 H：4.33 N：3.53.
The compound C12 of embodiment 8 preparation
With embodiment 1, difference is to use raw material 9,9- dimethyl fluorene -2- boric acid compound C12 preparation method Phenyl boric acid in alternative embodiment 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C59H42N2, theoretical value 778.3348, test value 778.3345.Elementary analysis (C59H42N2), theoretical value C：90.97 H：5.43 N：3.60, measured value C：90.94 H：5.41 N：3.65.
The compound C13 of embodiment 9 preparation
With embodiment 1, difference is to use raw material pyrene -1- boric acid alternative embodiment 1 compound C13 preparation method In phenyl boric acid.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C61H38N2, theoretical value 798.3035, test value 798.3039.Elementary analysis (C61H38N2), theoretical value C：91.70 H：4.79 N：3.51, measured value C：91.73 H：4.78 N：3.49.
The compound C14 of embodiment 10 preparation
With embodiment 1, difference is to replace in fact using raw material triphenylene -2- boric acid compound C14 preparation method Apply the phenyl boric acid in example 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C65H38N2, theoretical value 846.3035, test value 846.3039.Elementary analysis (C65H38N2), theoretical value C：92.17 H：4.52 N：3.31, measured value C：92.14 H：4.54 N：3.32.
The compound C17 of embodiment 11 preparation
With embodiment 1, difference is to replace using raw material dibenzofurans -4- boric acid compound C17 preparation method The phenyl boric acid changed in embodiment 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H30N2O2, theoretical value 726.2307, test value 726.2310.Elementary analysis (C53H30N2O2), theoretical value C：87.58 H：4.16 N：3.85 O：4.40, measured value C： 87.55 H：4.18 N：3.88 O：4.39.
The compound C19 of embodiment 12 preparation
With embodiment 1, difference is to replace using raw material N- phenyl carbazole -3- boric acid compound C19 preparation method The phenyl boric acid changed in embodiment 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C65H40N4, theoretical value 876.3253, test value 876.3257.Elementary analysis (C65H40N4), theoretical value C：89.01 H：4.60 N：6.39, measured value C：89.05 H：4.57 N：6.38.
Device embodiments
The present invention chooses compound C02, compound C04, compound C07, compound C08, compound C09, compound C10, compound C12, compound C13, compound C14, compound C17, compound C19 make organic electroluminescence device, by This is prepared for embodiment 13-23 organic electroluminescence device respectively.
All embodiments prepare blue organic electroluminescent device by the following method：
A) ITO (tin indium oxide) glass substrate (101) is cleaned：Respectively ITO is cleaned with deionized water, acetone, EtOH Sonicate Each 30 minutes of glass, then handled 5 minutes in plasma cleaner；
B) vacuum evaporation hole transmission layer (102) NPB, thickness 50nm on anode ito glass substrate (101)；
C) on hole transmission layer NPB, one of above-claimed cpd as luminescent layer (103) of vacuum mixing evaporation with BEP, the compound and BEP mass ratio 9:1, thickness 30nm；
D) on luminescent layer (103), the vacuum evaporation TPBI as electron transfer layer (104), thickness 30nm；
E) on electric transmission (104) layer TPBI, vacuum evaporation electron injecting layer (105) LiF, thickness 1nm；
F) on electron injecting layer (105) LiF, vacuum evaporation negative electrode (106) Al, thickness 100nm.
The structure of device is ITO/NPB (50nm)/compound：BEP=9:1, (W/W, 30nm)/TPBI (30nm)/ LiF(1nm)/Al(100nm)。
All device embodiments of the present invention are identical with the manufacture craft of comparative example, and employed identical base Plate material and electrode material, the thickness of electrode material are also consistent, except that the main body material to the luminescent layer in device Material converts.The composition structure of each device is as shown in table 1.The test result of device is shown in Table 2.
The device architecture of table 1
The device detection result of table 2
The result of table 2 can be seen that compound of the present invention can make using with OLED luminescent devices, and compared with Example is compared, and is either opened bright voltage or high-high brightness and is obtained larger change than known OLED material.Material of the present invention There is good application effect in OLED luminescent devices, there is good industrialization prospect.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent substitution and improvements made etc., it should be included in the scope of the protection.

Claims (6)

1. a kind of organic photoelectrical material, it is characterised in that the structural formula of the organic photoelectrical material is：
2. the preparation method of the organic photoelectrical material any one of claim 1, it is characterised in that comprise the following steps：
1) based on 2,6- dibromo-anthraquinones, synthetic intermediate 1, reaction equation is as follows：
2) compound 1 is synthesized with the intermediate 1, reaction equation is as follows：
3) it is raw material with the compound 1, carries out fork coupling reaction with the aromatic compounds of boronate substitution, obtain described organic Luminescent material.
3. a kind of organic electroluminescence device, including luminescent layer, it is characterised in that the luminescent layer is by any in claim 1 Luminescent material and BEP compositions described in.
4. organic electroluminescence device according to claim 3, it is characterised in that the luminescent material is with the BEP's Mass ratio is 9:1.
5. organic electroluminescence device according to claim 3, it is characterised in that the organic electroluminescence device by ITO Conducting Glass, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer, which stack gradually, to be formed.
6. organic electroluminescence device according to claim 5, it is characterised in that the hole transmission layer is made up of NPB, The electron transfer layer is made up of TPBI, and the electron injecting layer is made up of lithium fluoride, and the cathode layer is made of aluminum.
CN201610711611.6A 2016-08-24 2016-08-24 A kind of organic photoelectrical material and the organic electroluminescence device comprising the material Active CN106349106B (en)

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