CN107502343A - A kind of electroluminescent organic material and application - Google Patents

A kind of electroluminescent organic material and application Download PDF

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CN107502343A
CN107502343A CN201710788243.XA CN201710788243A CN107502343A CN 107502343 A CN107502343 A CN 107502343A CN 201710788243 A CN201710788243 A CN 201710788243A CN 107502343 A CN107502343 A CN 107502343A
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yellow solid
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高树坤
邹广辉
李银花
盛磊
胡葆华
周银波
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Valiant Co Ltd
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Abstract

The invention belongs to field of organic electroluminescence, more particularly to a kind of electroluminescent organic material and application.The present invention is reacted by coupling, cyclization etc., it is prepared for a kind of compound using biacridine derivatives and five-membered ring as core, this quasi-molecule has suitable molecular weight (400~1200), wider energy gap (being in 3.5~4.0eV), higher glass transition temperature Tg (more than 120 DEG C), is suitable as luminescent layer material of main part.In the molecular structure of such material, electron donating group is connected with drawing electron group by simultaneously ring structure, the configuration of this distortion, increases the stereoeffect of whole molecule, the electronics being more beneficial in luminescent layer and the conduction in hole and combination, it is significant to improving current efficiency.Compared with the material of main part CBP of commercialization, using material of the present invention as material of main part, the organic electroluminescence device of making, current efficiency improves 20%, and device lifetime improves 75%.

Description

A kind of electroluminescent organic material and application
Technical field
The invention belongs to field of organic electroluminescence, more particularly to a kind of electroluminescent organic material and application.
Background technology
Pope et al. is found that the Electroluminescence Properties of monocrystalline anthracene in nineteen sixty-five first, and this is the first electricity of organic compound Photoluminescence phenomenon.By continuous development for many years, organic electroluminescence device can both be used for manufacturing new display product, also may be used For making novel illumination product, it is expected to substitute available liquid crystal to show and fluorescent lighting.
The infrastructure element that OLED is shown is OLED, and OLED can be divided into glimmering according to the difference of luminous mechanism Two kinds of optical device and phosphorescent devices.Fluorescent device is that a kind of singlet state (singlet) is luminous, and phosphorescent devices are a kind of triplets (triplet) light, according to hole and the computational theory of the spin state of electronics, in theory, phosphorescent devices generally have higher Luminous efficiency.
Since Forrest in 1997 et al. realizes electroluminescent phosphorescence, the phosphorescent light-emitting materials based on heavy metal complex are just Developed rapidly, up to the present, existing many review articles are summarized summary to phosphorescent complexes, with Re, Ru, Os, Ir with the metal organic complex centered on Pt DengV lll races heavy metal atoms there is strong spin-orbit lotus root to cooperate With.
Lighted to obtain phosphorescence, in luminescent material, it is necessary to above-mentioned so-called " heavy atom " effect is introduced, heavy atom The molecular orbit of out orbit and light emitting molecule intercouples, and the transition section that can make to be prohibited originally releases, so that phosphorus Light is luminous to be possibly realized, and at present, selected heavy atom is based on metal iridium, because iridium is a kind of rare metal, therefore phosphorescence The price of material is generally very expensive, such as green light material Ir (ppy)3(CAS-RN:94928-86-6), day blue light material Flrpic (CAS-RN:376367-93-0) etc., its price is all higher than 10000 yuan/g.In the phosphorescent emitter reported, people are especially It is interested in the complex centered on trivalent metal iridium, and the complex of iridium being most widely studied also has transmitting blue light FIrpic, (ppy) of green glow2Ir (acac) and feux rouges (piq)2Ir(acac)。
In addition to price factor, another problem of phosphorescent light-emitting materials, is concentration quenching under high doping be present, when phosphor material is dense When spending high, phosphorescence is luminous to be quenched, for this reason, it may be necessary among phosphorescent light-emitting materials are dispersed in into another material, carry out " dilute Release ", here it is " doping " technology, by doping, tends to be obviously improved device efficiency, extends device lifetime, and obtain more Good spectrum excitation.In device is adulterated, phosphorescent light-emitting materials are referred to as " guest materials " or " dopant ", play peptizaiton Material is referred to as " material of main part ".
Although material of main part is not directly luminous, material of main part has for the overall performance of device to be significantly affected. Therefore, new effective material of main part is developed to seem and guest materials no less important.Generally, using the main body material with commercial device Material needs have suitable triplet energy level, higher glass transition temperature, preferable heat endurance, and has necessarily Carrier transport ability.
4,4'- bis- (9- carbazoles) biphenyl (CAS-RN:58328-31-7, abbreviation CBP, structural formula are as follows：
CBP is common commercialization phosphorescent light body material, and the material has a good triplet energy level, heat endurance compared with It is good, but because the whole molecules of CBP excessively " thin ", molecular weight are smaller, therefore, its glass transition temperature only has 62 DEG C.
The content of the invention
The technical problem to be solved by the invention is to provide a kind of electroluminescent organic material, such material has suitable Molecular entergy level, higher glass transition temperature, green phosphorescent material of main part can be used as, apply organic electroluminescent lead In domain.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of electroluminescent organic material, its structural formula is such as Under：
Wherein, X is any one of oxygen atom or C1-10 aliphatic groups；R1For any one of C5-30 aryl；R2For Any one of C5-30 aryl or C1-10 aliphatic groups；R3For any of C5-30 aryl, C1-10 aliphatic groups or hydrogen atom It is a kind of；R4For any one of C5-30 aryl, C1-10 aliphatic groups or hydrogen atom.
Preferably, X is oxygen atom or isopropyl；R1For phenyl or 4- xenyls；R2For phenyl or methyl；R3For phenyl, uncle Butyl or hydrogen atom；R4For phenyl, the tert-butyl group or hydrogen atom.
Above-mentioned electroluminescent organic material, its structural formula are：
Second object of the present invention is to provide a kind of above-mentioned electroluminescent organic material as emitting layer material, is making Make the application in organic electroluminescence device field.
The beneficial effects of the invention are as follows：
1st, the present invention by coupling, cyclization etc. react, be prepared for it is a kind of using biacridine derivatives simultaneously five-membered ring as core Compound, this quasi-molecule have suitable molecular weight (400~1200), wider energy gap (being in 3.5~4.0eV), higher Glass transition temperature Tg (more than 120 DEG C), be suitable as luminescent layer material of main part.
2nd, in the molecular structure of such material, electron donating group is connected with drawing electron group by simultaneously ring structure, this The configuration of distortion, increase the stereoeffect of whole molecule, the electronics being more beneficial in luminescent layer and the conduction in hole with With reference to significant to improving current efficiency.
3rd, using such material as material of main part, existing luminescent material GD-19, Ir (PPy) are adulterated respectively3、GD-PACTZ As luminescent layer, the current efficiency of prepared organic electroluminescence device and device lifetime are obviously improved.
4th, compared with the material of main part CBP of commercialization, using material of the present invention as material of main part, making it is organic Electroluminescent device, current efficiency improve 20%, and device lifetime improves 75%.
Brief description of the drawings
Fig. 1 is the structural representation of organic electroluminescence device of the present invention；
In figure, 1, transparent substrate layer；2nd, ito anode layer；3rd, hole injection layer；4th, hole transmission layer；5th, luminescent layer；6th, it is electric Sub- transport layer；7th, electron injecting layer；8th, negative electrode layer.
Embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit Determine the scope of the present invention.
The compound C01 of embodiment 1 preparation
The preparation of compound 1：In 1000mL there-necked flasks, addition 2,8- dibromos dibenzofurans (32.6g, 0.1mol), Aniline (18.6g, 0.2mol), sodium tert-butoxide (28.8g, 0.3mol), dimethylbenzene (750mL), palladium (0.245g) and three uncles Butyl phosphorus tetrafluoroborate (0.580g), under nitrogen protection, backflow is warming up to, insulation reaction 10h, is down to room temperature, to reaction bulb Middle addition 200mL deionized waters, 15min is stirred, liquid separation, 300mL deionized waters washing organic phase 3 times, collects organic phase, it is anhydrous Na2SO450cm thickness silicagel columns are crossed after drying, 1L toluene elution pillar, merged post liquid desolventizing, gained yellow solid uses first Benzene：Petroleum ether=1:6 backflow mashing purifying, filter and dry after cooling, obtain compound 1, faint yellow solid 26.6g, yield 75.8%, MS (m/z)：350.1；
The preparation of compound 2：In 1000mL there-necked flasks, compound 1 (17.5g, 0.05mol), o-bromobenzoic acid are added Methyl esters (21.5g, 0.1mol), sodium tert-butoxide (14.4g, 0.15mol), dimethylbenzene (700mL), palladium (0.122g) and three uncles Butyl phosphorus tetrafluoroborate (0.290g), under nitrogen protection, backflow is warming up to, insulation reaction 15h, is down to room temperature, to reaction bulb Middle addition 150mL deionized waters, 15min is stirred, liquid separation, 200mL deionized waters washing organic phase 3 times, collects organic phase, it is anhydrous Na2SO440cm thickness silicagel columns are crossed after drying, 1.5L toluene elution pillar, merged post liquid desolventizing, gained yellow solid uses Toluene：Petroleum ether=1:6 backflow mashing purifying, filter and dry after cooling, obtain compound 2, faint yellow solid 24.2g, receive Rate 78.3%, MS (m/z)：618.2；
The preparation of compound 3：In 500mL there-necked flasks, magnesium chips (2.7g, 0.11mol) is added, under nitrogen protection, heating To 100 DEG C, insulation reaction 1h, room temperature is down to, an iodine is added into reaction bulb, a small amount of iodomethane solution (14.2g is added dropwise (0.10mol) iodomethane is formulated with 150g methyl tertiary butyl ether(MTBE)s), after reaction triggers, continue that remaining iodomethane solution is added dropwise, Warm 35-40 DEG C in control, about 1h drops finish, and 40 DEG C of insulation 2h, system is grey black clear solution.Temperature is added dropwise to 30-35 DEG C in drop 12.4g (0.02mol) compound 2 and 15g methyl tertiary butyl ether(MTBE)s, the solution of 50g tetrahydrofurans, heat release, system gradually bleach, and produce Anger is steeped, and warm 35-45 DEG C in control, about 1h drops finish, 50-55 DEG C of insulation 1h；After reaction completely, into system, dropwise addition 100mL satisfies And aqueous ammonium chloride solution, heat release, temperature is less than 40 DEG C in control；0.5h is stirred, system is limpid, is added after liquid separation into organic phase 100g running water stirs 30min, liquid separation, organic phase anhydrous sodium sulfate drying, after desolventizing weak yellow liquid, petroleum ether return Stream mashing purifying, filters and dries after cooling, obtain compound 3, faint yellow solid 5.6g, yield 45.3%, MS (m/z)： 618.3；
The preparation of compound 4：In 250mL there-necked flasks, compound 3 (6.2g, 0.01mol) and dichloromethane are added (100g), after stirring and dissolving, be down to -5-5 DEG C, to reaction bulb liquid level under be passed through dry hydrogen chloride gas；, will after ventilation 12h Reaction solution is poured into 100ml frozen water, stirs 15min, and organic phase, anhydrous Na are collected in liquid separation2SO430cm thickness silicagel columns are crossed after drying, 300g eluent methylene chloride pillars, merged post liquid desolventizing, and gained yellow solid, flowed back using petroleum ether and be beaten purifying, it is cold But filter and dry afterwards, obtain compound 4, yellow solid 5.7g, yield 87.6%, MS (m/z)：654.2；
Compound C01 preparation：In 500mL there-necked flasks, alchlor powder (1.33g, 0.01mol) and chlorobenzene are added (70g), under nitrogen protection, system is down to 5-10 DEG C, and compound 4 (6.56g, 0.01mol) and chlorobenzene are added dropwise into reaction bulb The solution of (200g), drip 30-50 DEG C of insulation 6-8h after finishing；After reaction terminates, reaction solution is poured into watery hydrochloric acid, liquid separation is simultaneously collected Organic phase, anhydrous Na2SO4Dry, filtering, slough solvent, crude product crosses silica gel column chromatography purifying, and eluant, eluent is toluene：Petroleum ether= 1:3, obtain compound C01, faint yellow solid 3.81g, yield 65.4%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C42H34N2O, theoretical value 582.2671, test value 582.2725.Elementary analysis (C42H34N2O), theoretical value C：86.57 H：5.87 N：4.81 O：2.75, measured value C：86.55, H：5.88 N：4.83 O：2.74.
The compound C03 of embodiment 2 preparation
The preparation of compound 5：Compound C01 (11.7g, 0.02mol) is dissolved in the DMF of 100g dryings, be transferred to In 250ml there-necked flasks, under nitrogen protection, dissolving is stirred at room temperature, slowly in batches addition NBS solid powders (7.1g, 0.04mol), 120 DEG C of insulation reaction 5h, system are quickly turned to the transparent system of claret, and insulation, which is finished, naturally cools to room temperature, adds 200g toluene and 150g water, 0.5h is stirred, liquid separation, organic phase is collected, sloughs solvent, obtain the crude product of compound 5, gained is thick Product is solvent recrystallization using equal proportion toluene/ethanol, obtains the fine work of compound 5, faint yellow solid 10.6g, yield 71.6%, MS (m/s)：740.1；
Compound C03 preparation：In 250mL there-necked flasks, compound 5 (7.41g, 0.01mol), phenyl boric acid are added (2.67g, 0.022mol), potassium carbonate (3.45g, 0.025mol), toluene (150g), ethanol (50g) and deionized water (65g), Under nitrogen protection, Pd (PPh are added3)4(0.116g) and Xantphos (0.116g), it is warming up to backflow, insulation reaction 8h, cooling To 30 DEG C, liquid separation, organic phase is washed once with 120g water, liquid separation, and organic phase is after the drying of 50g anhydrous magnesium sulfates, quick mistake Silicagel column thick 25cm, cross post liquid desolventizing and obtain faint yellow solid crude product, crude product is crossed silicagel column, petroleum ether elution, collected containing single One product component crosses post liquid, and petroleum ether is beaten after precipitation, and suction filtration obtains compound C03, white solid 5.18g, yield 70.5%；
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C54H42N2O, theoretical value 734.3297, test value 734.3553.Elementary analysis (C54H42N2O), theoretical value C：88.25 H：5.76 N：3.81 O：2.18, measured value C：88.27, H：5.74 N：3.82 O：2.17.
The compound C04 of embodiment 3 preparation
Compound C04 preparation：In 500mL there-necked flasks, tertiary butyl chloride (0.93g, 0.01mol), chlorobenzene are added (70g), under nitrogen protection, system is down to 5-10 DEG C, and compound C01 (5.83g, 0.01mol) and chlorobenzene are added dropwise into reaction bulb The solution of (200g), drip 30-50 DEG C of insulation 6-8h after finishing；After reaction terminates, reaction solution is poured into watery hydrochloric acid, liquid separation is simultaneously collected Organic phase, anhydrous Na2SO4Dry, filtering, slough solvent, crude product crosses silica gel column chromatography purifying, and eluant, eluent is toluene：Petroleum ether= 1:3, obtain compound C04, faint yellow solid 4.9g, yield 76.9%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C46H42N2O, theoretical value 638.3297, test value 638.3159.Elementary analysis (C46H42N2O), theoretical value C：86.48 H：6.63 N：4.39 O：2.50, measured value C：86.50, H：6.61 N：4.38 O：2.51.
The compound C05 of embodiment 4 preparation
The preparation method of compound 6 with compound 5 in embodiment 2 preparation, difference be NBS dosages for (3.6g, 0.02mol), the fine work of compound 6, faint yellow solid 9.7g, yield 73.6%, MS (m/s) are obtained：660.2；
For compound C05 preparation method with the preparation of compound C03 in embodiment 2, difference is phenyl boric acid dosage For (1.34g, 0.011mol), compound C05, faint yellow solid 3.83g, yield 58.1% are obtained.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C48H38N2O, theoretical value 658.2984, test value 658.2730.Elementary analysis (C48H38N2O), theoretical value C：87.51 H：5.81 N：4.25 O：2.43, measured value C：87.53, H：5.79 N：4.24 O：2.44.
The compound C07 of embodiment 5 preparation
Preparation of the preparation method of compound 7 with compound 1 in embodiment 1：Difference be by aniline (18.6g, 4- benzidine (33.8g, 0.2mol) 0.2mol) is replaced by, obtains compound 7, faint yellow solid 40.2g, yield 80.0%, MS (m/z)：502.2；
Preparation of the preparation method of compound 8 with compound 2 in embodiment 1：Difference is compound 1 (17.5g, 0.05mol) is replaced by compound 7 (25.1g, 0.05mol), obtains compound 8, faint yellow solid 30.5g, yield 79.1%, MS (m/z)：770.3；
Preparation of the preparation method of compound 9 with compound 3 in embodiment 1：Difference is compound 2 (12.4g, 0.02mol) is replaced by compound 8 (15.4g, 0.02mol), obtains compound 9, faint yellow solid 7.2g, yield 46.7%, MS (m/z)：770.4；
Preparation of the preparation method of compound 10 with compound 4 in embodiment 1：Difference is compound 3 (6.2g, 0.01mol) is replaced by compound 9 (7.7g, 0.01mol), obtains compound 10, yellow solid 7.2g, yield 89.1%, MS (m/z)：806.3；
Preparation of the compound C07 preparation method with compound C01 in embodiment 1：Difference is compound 4 (6.56g, 0.01mol) is replaced by compound 10 (8.08g, 0.01mol), obtains compound C07, faint yellow solid 4.72g, receives Rate 64.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C54H42N2O, theoretical value 734.3297, test value 734.3441.Elementary analysis (C42H34N2O), theoretical value C：88.25 H：5.76 N：3.81 O：2.18, measured value C：88.27, H：5.77 N：3.80 O：2.16.
The compound C11 of embodiment 6 preparation
Preparation of the preparation method of compound 11 with compound 3 in embodiment 1：Difference is 14.2g (0.10mol) iodomethane is replaced by 20.4g (0.10mol) iodobenzene, obtains compound 11, faint yellow solid 8.8g, yield 50.7%, MS (m/z)：866.4；
Preparation of the preparation method of compound 12 with compound 4 in embodiment 1：Difference is compound 3 (6.2g, 0.01mol) is replaced by compound 11 (8.7g, 0.01mol), obtains compound 12, yellow solid 7.5g, yield 83.3%, MS (m/z)：902.3；
Preparation of the compound C11 preparation method with compound C01 in embodiment 1：Difference is compound 4 (6.56g, 0.01mol) is replaced by compound 12 (9.04g, 0.01mol), obtains compound C11, faint yellow solid 5.23g, receives Rate 62.9%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C62H42N2O, theoretical value 830.3297, test value 830.3512.Elementary analysis (C62H42N2O), theoretical value C：89.61 H：5.09 N：3.37 O：1.93, measured value C：89.62, H：5.09 N：3.37 O：1.92.
The compound C16 of embodiment 7 preparation
Preparation of the preparation method of compound 13 with compound 1 in embodiment 1：Difference is 2,8- dibromo hexichol It is light and furans (32.6g, 0.1mol) is replaced by bromo- 9, the 9- dimethyl fluorenes (35.2g, 0.1mol) of 3,6- bis-, obtains compound 13 Yellow solid 29.5g, yield 78.5%, MS (m/z)：376.2；
Preparation of the preparation method of compound 14 with compound 2 in embodiment 1：Difference is compound 1 (17.5g, 0.05mol) is replaced by compound 13 (18.8g, 0.05mol), obtains compound 14, faint yellow solid 25.7g, receives Rate 79.7%, MS (m/z)：644.3；
Preparation of the preparation method of compound 15 with compound 3 in embodiment 1：Difference is compound 2 (12.4g, 0.02mol) is replaced by compound 14 (12.9g, 0.02mol), obtains compound 15, faint yellow solid 6.0g, yield 46.5%, MS (m/z)：644.3；
Preparation of the preparation method of compound 16 with compound 4 in embodiment 1：Difference is compound 3 (6.2g, 0.01mol) is replaced by compound 15 (6.4g, 0.01mol), obtains compound 16, yellow solid 5.7g, yield 83.8%, MS (m/z)：680.3；
Preparation of the compound C16 preparation method with compound C01 in embodiment 1：Difference is compound 4 (6.56g, 0.01mol) is replaced by compound 16 (6.82g, 0.01mol), obtains compound C16, faint yellow solid 3.96g, receives Rate 65.0%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C45H40N2, theoretical value 608.3191, test value 608.3352.Elementary analysis (C45H40N2), theoretical value C：88.78 H：6.62 N：4.60, measured value C：88.76 H：6.63 N： 4.61。
The compound C20 of embodiment 8 preparation
Preparation of the preparation method of compound 17 with compound 6 in embodiment 4：Difference is compound C01 (11.7g, 0.02mol) is replaced by compound C16 (12.2g, 0.02mol), obtains the fine work of compound 17, faint yellow solid 10.1g, yield 73.6%, MS (m/s)：686.2；
Preparation of the compound C20 preparation method with compound C05 in embodiment 4：Difference is compound 6 (6.6g, 0.01mol) is replaced by compound 17 (6.9g, 0.01mol), obtains compound C20, faint yellow solid 4.12g, yield 60.1%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C51H44N2, theoretical value 684.3504, test value 684.3772.Elementary analysis (C51H44N2), theoretical value C：89.43 H：6.48 N：4.09, measured value C：89.45 H：6.47 N： 4.08。
The compound C22 of embodiment 9 preparation
Preparation of the preparation method of compound 18 with compound 7 in embodiment 5：Difference is 2,8- dibromo hexichol It is light and furans (32.6g, 0.1mol) is replaced by bromo- 9, the 9- dimethyl fluorenes (35.2g, 0.1mol) of 3,6- bis-, obtains compound 18 Yellow solid 38.3g, yield 72.4%, MS (m/z)：528.3；
Preparation of the preparation method of compound 19 with compound 8 in embodiment 5：Difference is compound 7 (25.1g, 0.05mol) is replaced by compound 18 (25.1g, 0.05mol), obtains compound 19, faint yellow solid 28.3g, receives Rate 71.0%, MS (m/z)：796.3；
Preparation of the preparation method of compound 20 with compound 9 in embodiment 5：Difference is will compound 8 (15.4g, 0.02mol) is replaced by compound 19 (15.4g, 0.02mol), obtains compound 20, faint yellow solid 7.1g, yield 44.7%, MS (m/z)：796.4；
Preparation of the preparation method of compound 21 with compound 10 in embodiment 5：Difference is compound 9 (7.7g, 0.01mol) is replaced by compound 20 (7.7g, 0.01mol), obtains compound 21, yellow solid 7.0g, yield 83.6%, MS (m/z)：832.3；
Preparation of the compound C22 preparation method with compound C07 in embodiment 5：Difference is compound 10 (8.08g, 0.01mol) is replaced by compound 21 (8.08g, 0.01mol), obtains compound C22, faint yellow solid 4.44g, receives Rate 58.3%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C57H48N2, theoretical value 760.3817, test value 760.3654.Elementary analysis (C57H48N2), theoretical value C：89.96 H：6.36 N：3.68, measured value C：89.98 H：6.34 N： 3.68。
The compound C30 of embodiment 10 preparation
Preparation of the preparation method of compound 22 with compound 20 in embodiment 9：Difference is iodomethane (14.2g, 0.10mol) is replaced by iodobenzene (20.4g, 0.10mol), obtains compound 22, faint yellow solid 11.3g, yield 54.0%, MS (m/z)：1044.5；
Preparation of the preparation method of compound 23 with compound 21 in embodiment 9：Difference is compound 20 (7.7g, 0.01mol) is replaced by compound 22 (10.2g, 0.01mol), obtains compound 23, yellow solid 8.7g, yield 80.4%, MS (m/z)：1080.4；
Preparation of the compound C30 preparation method with compound C20 in embodiment 9：Difference is being replaced by Compound 21 (8.08g, 0.01mol) is replaced by compound 23 (10.56g, 0.01mol), obtains compound C30, faint yellow solid 7.16g, yield 70.9%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C77H56N2, theoretical value 1008.4443, test value 1008.4231.Elementary analysis (C77H56N2), theoretical value C：91.63 H：5.59 N：2.78, measured value C：91.61 H：5.60 N：2.79.
The compound of the invention synthesized is described in detail in the devices as hair below by way of application examples 1-8 and comparative example 1-3 The application effect of photosphere material of main part.Application examples 2-8 of the present invention, comparative example 1-3 compared with application examples 1, the device Manufacture craft is identical, and employed identical baseplate material and electrode material, the thickness of electrode material also keep one Cause, except that being converted to the luminescent layer material of main part in device.The structure composition of device is as shown in table 1；Gained device The test result of part is shown in Table 2.
Application examples 1
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (compound C01 and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5：5 weight is than blending, thickness 30nm)/electronics Transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).Point of each compound Subformula is as follows：
Specific preparation process is as follows：
(1) transparent substrate layer 1 uses transparent material, such as glass；Ito anode layer 2 (thickness 150nm) is washed, Ultraviolet-ozone washing is carried out again after carrying out neutralizing treatment, high-purity water washing, drying successively, to remove having for transparent ITO surfaces Machine residue；
(2) on ito anode layer 2 after wash, using vacuum deposition apparatus, the molybdenum trioxide that thickness is 10nm is deposited MoO3Used as hole injection layer 3；And then the TAPC of 80nm thickness is deposited as hole transmission layer 4；
(3) after above-mentioned hole mobile material evaporation terminates, the luminescent layer 5 of OLED luminescent devices is made, its structure includes changing Compound C01 is as material of main part and GD-19 as dopant material, and dopant material doping ratio is 5% weight ratio, luminescent layer thickness For 30nm；
(4) after above-mentioned luminescent layer 5, it is TPBI to continue vacuum evaporation electron transport layer materials, and the vacuum of the material is steamed Plating thickness is 40nm, and this layer is electron transfer layer 6；
(5) on electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer that thickness is 1nm, this layer are made For electron injecting layer 7；
(6) on electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer that thickness is 80nm is made, this layer is the moon Pole reflection electrode layer 8 uses.
After completing OLED luminescent devices as described above, anode and negative electrode are connected with known drive circuit, surveyed The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.
Application examples 2
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (compound C03 and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electronics Transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Application examples 3
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness 80nm)/luminescent layer 5 (compound C06 and Ir (PPy)3According to 100:10 weight is than blending, thickness 30nm)/ Electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Application examples 4
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness 80nm)/luminescent layer 5 (compound C07 and Ir (PPy)3According to 100:10 weight is than blending, thickness 30nm)/ Electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Application examples 5
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (compound C15 and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electricity Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Application examples 6
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (compound C16 and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electricity Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Application examples 7
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness 80nm)/luminescent layer 5 (compound C22, GH-204 and Ir (PPy)3According to 70:30:10 weight is thick than blending Spend 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Application examples 8
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (compound C30, GH-204 and GD-PACTZ are according to 70 for (TAPC, thickness 80nm)/luminescent layer 5:30:5 weight is thick than blending Spend 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Comparative example 1
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (CBP and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Comparative example 2
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness 80nm)/luminescent layer 5 (CBP and Ir (PPy)3According to 100:10 weight is than blending, thickness 30nm)/electronics biography Defeated layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Comparative example 3
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4 (CBP and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electric transmission Layer (LiF, thickness the 1nm)/negative electrode layer 8 (Al) of 6 (TPBI, thickness 40nm)/electron injecting layer 7.
The device architecture of table 1
Table 2
Explanation:The current efficiency of comparative example 1 is 6.5cd/A (@10mA/cm2), startup voltage is 4.3V (@1cd/m2), LT95 life time decays are 3.8Hr under 5000nit brightness；The current efficiency of comparative example 2 is 24.6cd/A (@10mA/cm2), LT95 life time decays are 4.3Hr under 5000nit brightness；The current efficiency of comparative example 3 is 25.1cd/A (@10mA/cm2), start Voltage is 3.5V (@1cd/m2), and LT95 life time decays are 7.8Hr under 5000nit brightness.
From the results shown in Table 2, compound of the present invention can be applied to OLED hairs as luminescent layer material of main part Optical device makes, and compared with comparative example 1-3, either efficiency or life-span obtain larger change than known OLED material See, the driving life-span of particularly device obtains larger lifting.
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 (8)

1. a kind of electroluminescent organic material, it is characterised in that its structural formula is as follows：
Wherein, X is any one of oxygen atom or C1-10 aliphatic groups；R1For any one of C5-30 aryl；R2For C5-30 Any one of aryl or C1-10 aliphatic groups；R3For any one of C5-30 aryl, C1-10 aliphatic groups or hydrogen atom；R4 For any one of C5-30 aryl, C1-10 aliphatic groups or hydrogen atom.
2. electroluminescent organic material according to claim 1, it is characterised in that X is oxygen atom or isopropyl.
3. electroluminescent organic material according to claim 1, it is characterised in that R1For phenyl or 4- xenyls.
4. electroluminescent organic material according to claim 1, it is characterised in that R2For phenyl or methyl.
5. electroluminescent organic material according to claim 1, it is characterised in that R3For phenyl, the tert-butyl group or hydrogen atom.
6. electroluminescent organic material according to claim 1, it is characterised in that R4For phenyl, the tert-butyl group or hydrogen atom.
7. electroluminescent organic material according to claim 1, it is characterised in that its structural formula is：
8. a kind of any one of the claim 1-7 electroluminescent organic material is making organic electroluminescence as emitting layer material The application of light emitting device field.
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