CN109574931A - A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its application on organic electroluminescence device - Google Patents

A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its application on organic electroluminescence device Download PDF

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CN109574931A
CN109574931A CN201710900168.1A CN201710900168A CN109574931A CN 109574931 A CN109574931 A CN 109574931A CN 201710900168 A CN201710900168 A CN 201710900168A CN 109574931 A CN109574931 A CN 109574931A
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general formula
compound
nitrogen
raw material
molar ratio
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庞羽佳
唐丹丹
张兆超
张小庆
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

The invention discloses a kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its applications on organic electroluminescence device, belong to technical field of semiconductors.Shown in the structure of organic compound provided by the invention such as general formula (1):Application the invention also discloses the preparation method of above compound and its on organic electroluminescence device.The compounds of this invention provided by the invention glass transition temperature with higher and molecule thermal stability, suitable HOMO and lumo energy, higher Eg are optimized by device architecture, can effectively promote the photoelectric properties of OLED device and the service life of OLED device.

Description

A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its in Organic Electricity Application on electroluminescence device
Technical field
The present invention relates to a kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its in organic electroluminescence Application on part, belongs to technical field of semiconductors.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is very extensive.
Structure of the OLED luminescent device like sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together. As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity Depending on etc. large scales application field extension, still with actual products application require compare, the luminous efficiency of OLED device, use The performances such as service life also need further to be promoted.
Proposing high performance research for OLED luminescent device includes: the driving voltage for reducing device, improves shining for device Efficiency improves the service life etc. of device.In order to realize OLED device performance continuous promotion, not only need from OLED device The innovation of structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out higher performance OLED Functional material.
Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two major classes, i.e. charge injection transmission from purposes Material and luminescent material further can also inject charge into transmission material and be divided into electron injection transmission material, electronic blocking material Luminescent material, can also be divided into main body luminescent material and dopant material by material, hole injection transmission material and hole barrier materials.
In order to make high performance OLED luminescent device, it is desirable that various organic functional materials have good photoelectric characteristic, For example, as charge transport materials, it is desirable that have good carrier mobility, high-vitrification conversion temperature etc., as luminous The material of main part of layer requires material to have good bipolarity, HOMO/LUMO energy rank appropriate etc..
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, applies in industry OLED device structure then includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography A variety of film layers such as defeated layer, electron injecting layer, that is to say, that the photoelectric functional material applied to OLED device is infused including at least hole Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form with rich and more The characteristics of sample.In addition, used photoelectric functional material has stronger for the collocation of the OLED device of different structure Selectivity, performance of the identical material in different structure device, it is also possible to completely totally different.
Therefore, for the industry application requirement of current OLED device and the different function film layer of OLED device, device Photoelectric characteristic demand, it is necessary to which selection is more suitable for, and OLED functional material or combination of materials with high performance are just able to achieve device High efficiency, the overall characteristic of long-life and low-voltage.For current OLED shows the actual demand of Lighting Industry, OLED at present The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, as the organic of material enterprise development higher performance Functional material is particularly important.
Summary of the invention
An object of the present invention is to provide a kind of compound of nitrogen-containing hetero heptatomic ring derivative.Provided by the invention Invention compound glass transition temperature with higher and molecule thermal stability, suitable HOMO and lumo energy, higher Eg pass through Device architecture optimization, can effectively promote the photoelectric properties of OLED device and the service life of OLED device
The technical scheme to solve the above technical problems is that a kind of compound of nitrogen-containing hetero heptatomic ring derivative, Shown in the structure of the compound such as general formula (1):
Wherein, o, p are equal to 0 or 1, and o, p are not 0 simultaneously；Ar1、Ar2Separately be expressed as singly-bound, replace or not Substituted C6-60Arlydene contains one or more heteroatomic substituted or unsubstituted 5~60 yuan of heteroarylidenes；The miscellaneous original Son is nitrogen, oxygen or sulphur；
In general formula (1), R1、R2Separately it is expressed as structure shown in general formula (2)；
Wherein,Be expressed as-,=orR3And R4Independently be expressed as hydrogen atom, general formula (3) or general formula (4) structure shown in；
In general formula (3), a is selected fromOne of；X1、X2、X3Respectively oxygen atom, Sulphur atom, selenium atom, C1-10Alkylidene, the alkyl-substituted imines of alkylidene, aryl substitution that linear or branched alkyl group replaces One of the imido grpup that base or aryl replace；
General formula (3) or general formula (4) separately pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL’1-CL’2Key, CL’2-CL’3Key or CL’3-CL’4Key is connect with general formula (2).
The structure of organic compound provided by the invention balances electrons and holes more in the distribution of luminescent layer, proper When HOMO energy level under, improve hole injection and transmission performance；Under suitable lumo energy, and play electronic blocking Effect promotes combined efficiency of the exciton in luminescent layer；When light emitting functional layer materials'use as OLED luminescent device, aryl Branch in the substituted fluorenes collocation scope of the invention can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduce high current Efficiency roll-off under density reduces device voltage, improves current efficiency and the service life of device；The branch of organic compound of the invention Chain is nitrogen-containing hetero heptatomic ring derivant structure, this structure has high triplet (T1), uses as electron-blocking materials, It can effectively stop the exciton energy of luminescent layer to be transferred in hole transmission layer, improve combined efficiency of the exciton in luminescent layer；Make When for luminescent layer material of main part, high triplet state can make energy is sufficiently effective to be transferred in dopant material, improve energy utilization Rate, to improve device light emitting efficiency.
Based on the above technical solution, the present invention can also be improved as follows.
Further, in general formula (1), the Ar1、Ar2Independently indicate are as follows: Or one of singly-bound.
Further, the compound is selected from the compound of general formula (5), general formula (6), general formula (7) or general formula (8),
Symbol used in it and label have the meaning provided in claim 1.
Further, the compound is selected from the compound of general formula (9), general formula (10), general formula (11) or general formula (12),
Symbol used in it and label have the meaning provided in claim 1.
Further, the compound is selected from the compound of general formula (13), general formula (14), general formula (15) or general formula (16),
Symbol used in it and label have the meaning provided in claim 1.
Further, the compound is selected from the compound of general formula (17), general formula (18), general formula (19) or general formula (20),
Symbol used in it and label have the meaning provided in claim 1.
Further, the general formula (2) is selected from general formula (21), general formula (22) or general formula (23),
Symbol used in it and label have the meaning provided in claim 1.
Further, the concrete structure formula of the compound are as follows:
In any one.
The second object of the present invention is to provide the preparation method of the compound of above-mentioned nitrogen-containing hetero heptatomic ring derivative.This hair The preparation method of bright organic compound is simple, wide market, is suitble to large-scale promotion application.
The technical scheme to solve the above technical problems is that a kind of chemical combination of above-mentioned nitrogen-containing hetero heptatomic ring derivative The preparation method of object, comprising:
Work as Ar1、Ar2When for singly-bound, the reaction equation that occurs in preparation process are as follows:
Specific preparation process the following steps are included:
1) raw material I and H-R are weighed1, toluene dissolution；Wherein, the raw material I and H-R1Molar ratio be 1:(1.2~1.5)；
2) Pd is added in Xiang Shangshu reaction system2(dba)3, tri-tert-butylphosphine and sodium tert-butoxide, obtain mixed solution；Wherein, Pd2(dba)3Be (0.006~0.02) with the molar ratio of raw material I: 1, the molar ratio of tri-tert-butylphosphine and raw material I be (0.006~ 0.02): 1, the molar ratio of sodium tert-butoxide and raw material I is (2.0~3.0): 1；
3) under an inert atmosphere, the mixed solution of above-mentioned reactant is reacted to 10~24 at 95~110 DEG C of reaction temperature Hour, cooling and filtering reacting solution, filtrate revolving crosses silicagel column, obtains intermediate II；
4) by intermediate II and H-R2It is dissolved with toluene；Wherein, the intermediate II and the molar ratio of H-R2 are 1:(1.2 ~1.5)；
5) Pd is added into the reaction system in step 4)2(dba)3, tri-tert-butylphosphine and sodium tert-butoxide, obtain mixed solution； Wherein, the Pd2(dba)3It is (0.005~0.01) with the molar ratio of intermediate II: 1, the tri-tert-butylphosphine and intermediate II Molar ratio be (0.005~0.02): 1, the molar ratio of the sodium tert-butoxide and intermediate II is (1.5~3.0): 1；
6) under the protection of inert gas, the mixed solution of step 5) is reacted 10 under the conditions of 95~110 DEG C of temperature ~for 24 hours, cooled to room temperature, and filtering reacting solution, filtrate rotates to solvent-free, crosses neutral silica gel column, obtains targeted Close object；
Work as Ar1、Ar2When not being singly-bound, the reaction equation that occurs in preparation process are as follows:
Specific preparation process the following steps are included:
1) with raw material I and boronic acid compounds R1-Ar1-B(OH)2For raw material, toluene dissolution；Wherein, the toluene dosage is The molar ratio of every gram of use 30-50ml toluene of raw material I, the raw material I and boronic acid compounds is 1:(1.0~1.5)；
2) Pd (PPh is added into the reaction system of step 1)3)4And sodium carbonate, obtain mixed solution；Wherein, the Pd (PPh3)4Molar ratio with raw material I is (0.005~0.01): 1, the molar ratio of the sodium carbonate and raw material I is (1.5~3.0): 1；
3) it under nitrogen protection, by above-mentioned mixed solution in 95~110 DEG C, reacts 10~24 hours, naturally cools to room Temperature, and filtering reacting solution, filtrate carry out vacuum rotary steam, cross neutral silica gel column, obtain intermediate III；
4) with intermediate III and boronic acid compounds R2-Ar2-B(OH)2For raw material, toluene dissolution；Wherein, the toluene dosage For every gram of use 30-50ml toluene of intermediate III, the molar ratio of the intermediate III and boronic acid compounds is 1:(1.0~1.5)；
5) Pd (PPh is added into the reaction system of step 4)3)4And sodium carbonate, obtain mixed solution；Wherein, the Pd (PPh3)4It is (0.005~0.01) with the molar ratio of intermediate III: 1, the molar ratio of the sodium carbonate and intermediate III is (1.5 ~3.0): 1；
6) it under nitrogen protection, by the mixed solution of step 5) in 95~110 DEG C, reacts 10~24 hours, natural cooling To room temperature, and filtering reacting solution, filtrate carry out vacuum rotary steam, cross neutral silica gel column, obtain target compound.
The third object of the present invention is to provide a kind of organic electroluminescence device.Organic compound provided by the invention exists OLED device can keep high membranous layer stability, can effectively promote the photoelectricity of OLED device in application, by device architecture optimization The service life of performance and OLED device.Compound of the present invention has good application effect and production in OLED luminescent device Industry prospect.
The technical scheme to solve the above technical problems is that a kind of organic electroluminescence device, at least one layer of function Ergosphere contains the compound of above-mentioned nitrogen-containing hetero heptatomic ring derivative.
Based on the above technical solution, the present invention can also be improved as follows.
Further, the functional layer is luminescent layer and/or electronic barrier layer and/or hole transmission layer.
The fourth object of the present invention is to provide a kind of illumination or display element.Organic electroluminescence device of the invention can To apply in illumination or display original set, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Together When, device lifetime is promoted clearly, there is good application effect in OLED luminescent device, there is good industry Change prospect.
The technical scheme to solve the above technical problems is that a kind of illumination or display element, including it is as described above Organic electroluminescence device.
The beneficial effects of the present invention are:
1. the structure of organic compound provided by the invention balances electrons and holes more in the distribution of luminescent layer, Under appropriate HOMO energy level, hole injection and transmission performance are improved；Under suitable lumo energy, and play electronic blocking Effect, promote combined efficiency of the exciton in luminescent layer；When light emitting functional layer materials'use as OLED luminescent device, virtue The branch in the fluorenes collocation scope of the invention that base replaces can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduce high electricity Efficiency roll-off under current density reduces device voltage, improves current efficiency and the service life of device；Organic compound of the invention Branch is nitrogen-containing hetero heptatomic ring derivant structure, this structure has high triplet (T1), makes as electron-blocking materials With can effectively stop the exciton energy of luminescent layer to be transferred in hole transmission layer, improve combined efficiency of the exciton in luminescent layer； When as luminescent layer material of main part, high triplet state can make energy is sufficiently effective to be transferred in dopant material, improve energy benefit With rate, to improve device light emitting efficiency.
2. the preparation method of organic compound of the invention is simple, wide market, it is suitble to large-scale promotion application.
3. organic compound provided by the invention, in application, by device architecture optimization, can be kept high in OLED device Membranous layer stability can effectively promote the photoelectric properties of OLED device and the service life of OLED device.Compound of the present invention exists There is good application effect and industrialization prospect in OLED luminescent device.
4. organic electroluminescence device of the invention can be applied in illumination or display original set, the current efficiency of device, function Rate efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly, in OLED luminescent device In have good application effect, have good industrialization prospect.
Detailed description of the invention
Fig. 1 is the structural schematic diagram that material cited by the present invention is applied to OLED device, wherein representated by each label Component is as follows:
1, transparent substrate layer, 2, ito anode layer, 3, hole injection layer, 4, hole transport/electronic barrier layer, 5, luminescent layer, 6, hole barrier/electron transfer layer, 7, electron injecting layer, 8, cathode reflection electrode layer.
Fig. 2 is the efficiency curve diagram that OLED device of the invention measures at different temperatures.
Specific embodiment
The principle and features of the present invention will be described below with reference to the accompanying drawings, and the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the invention.
Embodiment 1: the synthesis of intermediate Cn:
(1) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, addition 0.1mol raw material I, 0.15mol raw material J, 0.3mol sodium tert-butoxide, 1 × 10-3mol Pd2(dba)3、1×10-3Mol tri-tert-butylphosphine, 150mL toluene, are heated to 95 DEG C, Back flow reaction 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate Sn。
(2) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, be added 150mL liquefied ammonia, 0.05mol intermediate Sn, Reaction solution is placed under 500w xenon lamp and carries out photochemical reaction 1 hour by 0.15mol potassium tert-butoxide, and ammonium nitrate is added and is quenched instead It answers, liquefied ammonia is evaporated rear residue and water is added, and water phase is extracted with dichloromethane, and anhydrous magnesium sulfate is dry, and filtrate revolving crosses silica gel Column obtains intermediate Cn.
Embodiment 2: the synthesis of intermediate Dn:
(1) raw material K, phenyl boric acid are weighed, be (2~3) with volume ratio: 1 toluene alcohol mixed solvent dissolves, in indifferent gas Under atmosphere, wet chemical, four triphenyl phosphorus palladiums is added, reacts 10~24 hours, is cooled to room temperature, mistake at 95~110 DEG C Filter, filtrate revolving, crosses silicagel column, obtains intermediate Tn；Wherein raw material K and phenyl boric acid molar ratio are 1:(1.2~1.5)；Bromine The molar ratio of compound raw material K and potassium carbonate is 1:(2.0~3.0)；The molar ratio of raw material K and four triphenyl phosphorus palladiums is 1:(0.01 ~0.02)；
(2) stannous chloride is dissolved in the concentrated hydrochloric acid of 50mL, the concentrated hydrochloric acid solution of stannous chloride is slowly dropped into intermediate It in Tn, is stirred at room temperature, sampling contact plate is until the reaction is complete；The aqueous solution of 2M NaOH is added dropwise to reaction mixture, until pH Modulation 8~10, filtering, filter residue are dissolved with methylene chloride, and saturated sodium chloride solution is added and washs 3~5 times, takes organic phase, depressurizes Revolving obtains intermediate Un；The ratio of the stannous chloride and intermediate Tn are (2~4): 1；
(3) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, addition 0.1mol intermediate Un, 0.15mol raw material L, 0.3mol sodium tert-butoxide, 1 × 10-3mol Pd2(dba)3、1×10-3Mol tri-tert-butylphosphine, 150mL toluene, are heated to 95 DEG C, Back flow reaction 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate Vn。
(4) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, be added 150mL liquefied ammonia, 0.05mol intermediate Vn, Reaction solution is placed under 500w xenon lamp and carries out photochemical reaction 1 hour by 0.15mol potassium tert-butoxide, and ammonium nitrate is added and is quenched instead It answers, liquefied ammonia is evaporated rear residue and water is added, and water phase is extracted with dichloromethane, and anhydrous magnesium sulfate is dry, and filtrate revolving crosses silica gel Column obtains intermediate Dn.
Embodiment 3: the synthesis of intermediate E n:
(1) raw material M1, raw material N1 are weighed, aqueous potassium phosphate solution, copper nano-particle and toluene is added, reacts 2 at 110 DEG C Hour, it is cooled to room temperature, is extracted through ethyl acetate, it is dry by washing, silicagel column is crossed, intermediate Y1 is obtained；Wherein raw material M1 It is 1:(1.0~1.4 with raw material N1 molar ratio)；The molar ratio of raw material M1 and potassium phosphate is 1:(2.0~3.0)；
(2) in the case where 0 DEG C is passed through nitrogen atmosphere tetrahydro furan is added in methylpyridinium iodide magnesium and intermediate Y1 by the there-necked flask of 250mL In muttering, 2h is stirred at room temperature, and reaction mixture is cooled to 0 DEG C, saturated ammonium chloride quenching reaction is added, 30min is stirred, true Aerial volatilization.Residue is extracted with chloroform, and anhydrous magnesium sulfate dries, filters, solvent flashing in vacuum, and acetic acid second is added in crude product In the mixed solution of ester and acetic acid, 3h is stirred at room temperature, and volatilizable object of going out in vacuum borine tetrahydrofuran is complexed at 0 DEG C Object and tetrahydrofuran are added in crude product, stir 1h at room temperature, after being cooled to 0 DEG C, hydrogen peroxide and sodium hydroxide are mixed molten Liquid is carefully added into wherein, is stirred 30min at room temperature, is then poured into water reaction mixture, is then extracted with dichloromethane, after Through water, salt washing, anhydrous magnesium sulfate is dried, filtered, and is crossed silicagel column, is obtained intermediate Y2；Wherein methylpyridinium iodide magnesium and intermediate Y1 molar ratio is 2:(1.0~1.3).
(3) intermediate Y2, phosphorus pentoxide, toluene, heating is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL Flow back 20min, and mixture is cooled to room temperature, after the dense salt that mass fraction is 20% is slowly added into solution in ice-water bath Water, layering, organic phase is dry with anhydrous magnesium sulfate, crosses silicagel column, obtains intermediate Y3；Wherein intermediate Y2 and phosphorus pentoxide Molar ratio is 1:(14~18).
(4) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, addition 0.1mol raw material I, 0.15mol intermediate Y3, 0.3mol sodium tert-butoxide, 1 × 10-3mol Pd2(dba)3、1×10-3Mol tri-tert-butylphosphine, 150mL toluene, are heated to 95 DEG C, Back flow reaction 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate Y4, HPLC purity 98.4%, yield 77.3%.
(5) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, be added 150mL liquefied ammonia, 0.05mol intermediate Y4, Reaction solution is placed under 500w xenon lamp and carries out photochemical reaction 1 hour by 0.15mol potassium tert-butoxide, and ammonium nitrate is added and is quenched instead It answers, liquefied ammonia is evaporated rear residue and water is added, and water phase is extracted with dichloromethane, and anhydrous magnesium sulfate is dry, and filtrate revolving crosses silica gel Column obtains intermediate E 1, HPLC purity 95.3%, yield 74.8%.
Embodiment 4: the synthesis of intermediate Fn:
(1) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, addition 0.1mol raw material O, 0.15mol raw material P, 0.3mol sodium tert-butoxide, 1 × 10-3mol Pd2(dba)3、1×10-3Mol tri-tert-butylphosphine, 150mL toluene, are heated to 95 DEG C, Back flow reaction 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate Wn。
(2) there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, be added 150mL liquefied ammonia, 0.05mol intermediate Wn, Reaction solution is placed under 500w xenon lamp and carries out photochemical reaction 1 hour by 0.15mol potassium tert-butoxide, and ammonium nitrate is added and is quenched instead It answers, liquefied ammonia is evaporated rear residue and water is added, and water phase is extracted with dichloromethane, and anhydrous magnesium sulfate is dry, and filtrate revolving crosses silica gel Column obtains intermediate Fn.
Such as table 1 of intermediate product synthesis material needed for embodiment.
Intermediate product synthesis material needed for 1 embodiment of table
Embodiment 5: the synthesis of compound 2:
Synthetic route:
(1) 0.04mol raw material B1,0.06mol1,4- dibromo is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL Benzene, 0.12mol sodium tert-butoxide, 4 × 10-4mol Pd2(dba)3、4×10-4Mol tri-tert-butylphosphine, 150mL toluene, are heated to reflux 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate G1, HPLC is pure Degree 97.3%, yield 79.3%.
(2) 0.02mol intermediate G1,40mL tetrahydrofuran is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL Dissolution completely, is cooled to -78 DEG C, and the tetrahydrofuran that the 1.6mol/L n-BuLi of 15mL is then added into reaction system is molten Liquid is added 0.024mol triisopropyl borate ester after reacting 3h at -78 DEG C, reacts 2h, reaction system is then risen to 0 DEG C, is added Entering the 2mol/L hydrochloric acid solution of 50mL, stirs 3h, ether extraction is added in fully reacting, and anhydrous magnesium sulfate drying is added in extract liquor, Revolving, is recrystallized with alcohol solvent, obtains intermediate H1, HPLC purity 98.9%, yield 65.7%.
(3) 0.01mol raw material A 1,0.015mol intermediate is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL H1 dissolves (90mL toluene, 45mL ethyl alcohol) with mixed solvent, 0.03mol Na is then added2CO3Aqueous solution (2M), logical nitrogen stir It mixes 1 hour, 0.0001mol Pd (PPh is then added3)4, it is heated to reflux 15 hours, samples contact plate, fully reacting.Natural cooling, Filtering, filtrate revolving, crosses silicagel column, obtains target product, HPLC purity 97.5%, yield 71.6%.
HRMS (EI): theoretical value 635.2613, measured value 635.2636.
Embodiment 6: the synthesis of compound 3:
Synthetic route:
By the synthetic method prepare compound 3 in embodiment 5, difference is to replace Isosorbide-5-Nitrae-dibromo with 1,3- dibromobenzene Benzene；Gained target product HPLC purity 97.4%, yield 70.1%.
HRMS (EI): theoretical value 635.2613, measured value 635.2629.
Embodiment 7: the synthesis of compound 5:
Synthetic route:
The there-necked flask of 250mL, under the atmosphere for being passed through nitrogen, addition 0.04mol raw material B1,0.06mol raw material A 2, 0.12mol sodium tert-butoxide, 4 × 10-4mol Pd2(dba)3、4×10-4Mol tri-tert-butylphosphine, 150mL toluene, are heated to reflux 24 Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, HPLC purity 98.7%, yield 72.4%.
HRMS (EI): theoretical value 559.2300, measured value 559.2316.
Embodiment 8: the synthesis of compound 8:
Synthetic route:
The preparation method of compound 8, the difference is that 2- dibromobenzene replaces Isosorbide-5-Nitrae-dibromobenzene with 1, is used with embodiment 5 Raw material A 2 replaces raw material A 1；Gained target product HPLC purity 90.7%, yield 68.2%.
HRMS (EI): theoretical value 635.2613, measured value 635.2636.
Embodiment 9: the synthesis of compound 9:
Synthetic route:
The preparation method of compound 9 is with embodiment 7, the difference is that replacing raw material B1 with intermediate C1；With raw material A 1 Replace raw material A 2；Gained target product HPLC purity 97.2%, yield 78.2%.
HRMS (EI): theoretical value 649.2406, measured value 649.2422.
Embodiment 10: the synthesis of compound 15:
Synthetic route:
The preparation method of compound 15 is with embodiment 7, the difference is that replacing raw material B1 with intermediate C2；With raw material A 1 Replace raw material A 2；Gained target product HPLC purity 91.5%, yield 63.1%.
HRMS (EI): theoretical value 675.2926, measured value 675.2917.
Embodiment 11: the synthesis of compound 18:
Synthetic route:
The preparation method of compound 18 is with embodiment 7, the difference is that replacing raw material B1 with intermediate C3；With raw material A 1 Replace raw material A 2；Gained target product HPLC purity 91.5%, yield 58.1%.
HRMS (EI): theoretical value 799.3239, measured value 799.3226.
Embodiment 12: the synthesis of compound 39:
Synthetic route:
The preparation method of compound 39, the difference is that 3- dibromobenzene replaces Isosorbide-5-Nitrae-dibromobenzene with 1, is used with embodiment 5 Intermediate C4 replaces raw material B1, replaces raw material A 1 with raw material A 2；Gained target product HPLC purity 91.5%, yield 63.7%.
HRMS (EI): theoretical value 800.3191, measured value 800.3176.
Embodiment 13: the synthesis of compound 63:
Synthetic route:
The preparation method of compound 63, the difference is that 3- dibromobenzene replaces Isosorbide-5-Nitrae-dibromobenzene with 1, is used with embodiment 5 Intermediate D1 replaces raw material B1, replaces raw material A 1 with raw material A 2；Gained target product HPLC purity 95.7%, yield 69.2%.
HRMS (EI): theoretical value 815.2824, measured value 815.2811.
Embodiment 14: the synthesis of compound 67:
Synthetic route:
The preparation method of compound 67 is with embodiment 7, the difference is that replacing raw material B1 with intermediate D2；With raw material A 1 Replace raw material A 2；Gained target product HPLC purity 91.4%, yield 69.2%.
HRMS (EI): theoretical value 791.3552, measured value 791.3568.
Embodiment 15: the synthesis of compound 80:
Synthetic route:
The preparation method of compound 80, the difference is that 3- dibromobenzene replaces Isosorbide-5-Nitrae-dibromobenzene with 1, is used with embodiment 5 Intermediate C5 replaces raw material B1；Gained target product HPLC purity 92.7%, yield 65.2%.
HRMS (EI): theoretical value 767.3188, measured value 767.3105.
Embodiment 16: the synthesis of compound 90:
Synthetic route:
The preparation method of compound 90, the difference is that 3- dibromobenzene replaces Isosorbide-5-Nitrae-dibromobenzene with 1, is used with embodiment 5 Intermediate C6 replaces raw material B1；Gained target product HPLC purity 97.1%, yield 61.2%.
HRMS (EI): theoretical value 741.2668, measured value 741.2685.
Embodiment 17: the synthesis of compound 96:
Synthetic route:
The preparation method of compound 96 is with embodiment 7, the difference is that replacing raw material A 2 with raw material A 1；With intermediate C7 Replace raw material B1.Gained target product HPLC purity 97.1%, yield 63.5%.
HRMS (EI): theoretical value 717.3396, measured value 717.3383.
Embodiment 18: the synthesis of compound 108:
Synthetic route:
The preparation method of compound 108 is with embodiment 7, the difference is that replacing raw material B1 with intermediate E 1.
HRMS (EI): theoretical value 675.2562, measured value 675.2547；Gained target product HPLC purity 95.7%, yield 64.1%.
Embodiment 19: the synthesis of compound 113:
Synthetic route:
The preparation method of compound 113 is with embodiment 5, the difference is that replacing raw material B1 with intermediate F1；In with 1, 3- dibromobenzene replaces 1,4- dibromobenzene；Gained target product HPLC purity 91.7%, yield 54.2%.
HRMS (EI): theoretical value 685.2770, measured value 685.2759.
Embodiment 20: the synthesis of compound 124:
Synthetic route:
The preparation method of compound 124 is with embodiment 7, the difference is that replacing raw material B1 with intermediate F2；Gained mesh Mark product HPLC purity 94.8%, yield 53.1%.
HRMS (EI): theoretical value 659.2613, measured value 659.2630.
Embodiment 21: the synthesis of compound 127:
Synthetic route:
The preparation method of compound 127 is with embodiment 7, the difference is that replacing raw material B1 with intermediate F3；Gained mesh Mark product HPLC purity 91.4%, yield 68.4%.
HRMS (EI): theoretical value 759.2926, measured value 759.2943.
The compounds of this invention uses in luminescent device, can be used as electronic blocking layer material, can also be used as luminescent layer Subjective and Objective materials'use.To the compounds of this invention 2,3,5,8,9,15,18,39,63,67,80,90,96,108,113,124, 127 carry out the test of hot property, T1 energy level, HOMO energy level respectively, and testing result is as shown in table 2.
2 testing result of table
Note: the "/" in upper table is expressed as not carrying out this test (height of the fluorescence quantum efficiency of electronic blocking layer material Influence to OLED device performance is smaller)；Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimeter) measurement, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is weightless in nitrogen atmosphere 1% temperature is measured, nitrogen flow 20mL/min on the TGA-50H thermogravimetric analyzer of Japanese Shimadzu Corporation；Three lines State energy level T1 is tested by the F4600 Fluorescence Spectrometer of Hitachi, and the test condition of material is 2 × 10-5Toluene solution；Highest accounts for It according to molecular orbit HOMO energy level is tested by photoelectron emissions spectrometer (AC-2 type PESA), tested as atmospheric environment.
By upper table data it is found that organic compound of the invention has high glass transition temperature, material membrane phase can be improved State stability further increases device service life；With high T1 energy level, luminescent layer energy loss can be stopped, to mention Rise device light emitting efficiency；Suitable HOMO energy level can solve the injection problem of carrier, can reduce device voltage；It is higher glimmering The luminous efficiency of OLED device can be improved in photo-quantum efficiency and refractive index.Therefore, the present invention is being answered by the compound of core of fluorenes After the different function layer of OLED device, the luminous efficiency and service life of device can be effectively improved.
In the devices below by way of device embodiments 1~17 and comparative example 1 OLED material that the present invention will be described in detail synthesizes Application effect.The production work of device embodiments 2~17 of the present invention, the device compared with device embodiments 1 of comparative example 1 Skill is identical, and uses identical baseplate material and electrode material, and the film thickness of electrode material is also consistent, and institute is not Same is that device 1-5 is the compounds of this invention as hole mobile material application；Device 6-10 is to use material of the present invention As electronic blocking layer material application；Device 11-17 is to use material of the present invention as emitting layer material application.It is each to implement The performance test results of example obtained device are as shown in table 3.
Device embodiments 1
As shown in Figure 1, a kind of electroluminescent device, preparation step include:
A) the ito anode layer 2 on transparent substrate layer 1 is cleaned, cleans each 15 with deionized water, acetone, EtOH Sonicate respectively Minute, then handled 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited by vacuum evaporation mode, with a thickness of 10nm, This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material is deposited by vacuum evaporation mode, uses embodiment of the present invention system Standby compound 2, with a thickness of 60nm, which is hole transmission layer 4；
D) on hole transmission layer 4, electronic blocking layer material TAPC is deposited by vacuum evaporation mode, with a thickness of 20nm, The layer is electronic barrier layer 5；
E) luminescent layer 6 is deposited on electronic barrier layer 5, uses known compound CBP as material of main part, Ir (ppy)3As dopant material, Ir (ppy)3Mass ratio with CBP is 10:90, with a thickness of 30nm；
F) on luminescent layer 6, electron transport material TPBI is deposited by vacuum evaporation mode, with a thickness of 40nm, this layer Organic material is used as hole barrier/electron transfer layer 7；
G) on hole barrier/electron transfer layer 7, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electricity Sub- implanted layer 8；
H) on electron injecting layer 8, vacuum evaporation cathode Al (100nm), the layer is cathode reflection electrode layer 9.
After the production for completing electroluminescent device according to above-mentioned steps, the current efficiency of measurement device and service life, result It is shown in Table 3.The molecular structural formula of associated materials is as follows:
Device embodiments 2
The present embodiment and device embodiments 1 the difference is that: the hole transport layer material of electroluminescent device is this The compound 3 of inventive embodiments preparation, the detection data of gained electroluminescent device are shown in Table 3.
Device embodiments 3
The present embodiment and device embodiments 1 the difference is that: the hole transport layer material of electroluminescent device is this The compound 5 of inventive embodiments preparation, the detection data of gained electroluminescent device are shown in Table 3.
Device embodiments 4
The present embodiment and device embodiments 1 the difference is that: the hole transport layer material of electroluminescent device is this The compound 113 of inventive embodiments preparation, the detection data of gained electroluminescent device are shown in Table 3.
Device embodiments 5
The present embodiment and device embodiments 1 the difference is that: the hole transport layer material of electroluminescent device is this The compound 124 of inventive embodiments preparation, the detection data of gained electroluminescent device are shown in Table 3.
Device embodiments 6
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Electronic blocking layer material is the compound 63 of preparation of the embodiment of the present invention, and the detection data of gained electroluminescent device is shown in Table 3 institutes Show.
Device embodiments 7
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Electronic blocking layer material is the compound 80 of preparation of the embodiment of the present invention, and the detection data of gained electroluminescent device is shown in Table 3 institutes Show.
Device embodiments 8
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Electronic blocking layer material is the compound 90 of preparation of the embodiment of the present invention, and the detection data of gained electroluminescent device is shown in Table 3 institutes Show.
Device embodiments 9
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Electronic blocking layer material is the compound 96 of preparation of the embodiment of the present invention, and the detection data of gained electroluminescent device is shown in Table 3 institutes Show.
Device embodiments 10
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Electronic blocking layer material is the compound 108 of preparation of the embodiment of the present invention, and the detection data of gained electroluminescent device is shown in Table 3 institutes Show.
Device embodiments 11
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 9 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3With compound 9 Mass ratio be 10:90, the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 12
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 15 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 15 mass ratio is 12:88, and the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 13
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 18 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 18 mass ratio is 8:92, and the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 14
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 39 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 39 mass ratio is 10:90, and the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 15
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 67 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 67 mass ratio is 7:93, and the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 16
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 8 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3With compound 8 Mass ratio be 10:90, the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 17
The present embodiment and device embodiments 1 the difference is that: the hole mobile material of electroluminescent device is NPB, Luminescent layer material of main part becomes the compound 127 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And chemical combination The mass ratio of object 127 is 10:90, and the detection data of gained electroluminescent device is shown in Table 3.
Device comparative example 1
The present embodiment and device embodiments 1 the difference is that: the material of the hole transmission layer of electroluminescent device becomes Detection data for known compound NPB, gained electroluminescent device is shown in Table 3.
The detection data of 3 electroluminescent device of table
Note: life-span test system is owner of the present invention and the OLED device life test that Shanghai University is studied jointly Instrument.
The compound of nitrogen-containing hetero heptatomic ring derivative of the present invention can be applied to OLED it can be seen from the result of table 3 Luminescent device production, and compared with comparative example, either efficiency or service life obtain larger change than known OLED material, Especially the life time decay of device obtains biggish promotion.
Further, the OLED device of material preparation of the present invention is able to maintain the long-life at high temperature, and device is implemented In 85 DEG C of progress high temperature driven life tests, acquired results are as shown in table 4 for example 1~17 and device comparative example 1.
4 high temperature driven life test of table
Device number The high temperature LT95 service life (Hr) Device number The high temperature LT95 service life (Hr)
Device embodiments 1 19.8 Device embodiments 10 31.2
Device embodiments 2 21.5 Device embodiments 11 40.6
Device embodiments 3 18.7 Device embodiments 12 41.6
Device embodiments 4 19.7 Device embodiments 13 44.4
Device embodiments 5 19.5 Device embodiments 14 39.2
Device embodiments 6 30.2 Device embodiments 15 42.7
Device embodiments 7 26.8 Device embodiments 16 35.9
Device embodiments 8 26.7 Device embodiments 17 40.8
Device embodiments 9 30.9 Device comparative example 1 8.5
From the data of table 4 it is found that device embodiments 1~17 are the device architecture of material of the present invention and known materials collocation, It is compared with device comparative example 1, under high temperature, OLED device provided by the invention has the driving service life well.
Further, work limitation rate is also more stable at low temperature for the OLED device of material preparation of the present invention, by device Embodiment 2,8,15 and device comparative example 1 are in -10~80 DEG C of sections progress efficiency tests, and acquired results are as shown in table 5 and Fig. 2.
5 efficiency test result of table
From the data of table 5 it is found that device embodiments 2,8,15 are the device architecture of material of the present invention and known materials collocation, It is compared with device comparative example 1, not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency is steadily increased.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.

Claims (13)

1. a kind of compound of nitrogen-containing hetero heptatomic ring derivative, which is characterized in that shown in the structure of the compound such as general formula (1):
Wherein, o, p are equal to 0 or 1, and o, p are not 0 simultaneously；Ar1、Ar2Separately it is expressed as singly-bound, substituted or unsubstituted C6-60Arlydene contains one or more heteroatomic substituted or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom is Nitrogen, oxygen or sulphur；
In general formula (1), R1、R2Separately it is expressed as structure shown in general formula (2)；
Wherein,Be expressed as-,=orR3And R4Independently be expressed as hydrogen atom, general formula (3) or general formula (4) institute The structure shown；
In general formula (3), a is selected fromOne of；X1、X2、X3Respectively oxygen atom, sulphur are former Son, selenium atom, C1-10Linear or branched alkyl group replace alkylidene, aryl replace alkylidene, alkyl-substituted imido grpup or One of the imido grpup that aryl replaces；
General formula (3) or general formula (4) separately pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL’1-CL’2Key, CL’2-CL’3 Key or CL’3-CL’4Key is connect with general formula (2).
2. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that in general formula (1), The Ar1、Ar2Independently indicate are as follows: Or singly-bound One of.
3. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the compound Selected from general formula (5), general formula (6), general formula (7) or general formula (8),
Symbol used in it and label have the meaning provided in claim 1.
4. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the compound Compound selected from general formula (9), general formula (10), general formula (11) or general formula (12),
Symbol used in it and label have the meaning provided in claim 1.
5. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the compound Compound selected from general formula (13), general formula (14), general formula (15) or general formula (16),
Symbol used in it and label have the meaning provided in claim 1.
6. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the compound Compound selected from general formula (17), general formula (18), general formula (19) or general formula (20),
Symbol used in it and label have the meaning provided in claim 1.
7. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the general formula (2) it is selected from general formula (21), general formula (22) or general formula (23),
Symbol used in it and label have the meaning provided in claim 1.
8. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the general formula (1) R in1、R2It indicates are as follows:
In any one.
9. a kind of compound of nitrogen-containing hetero heptatomic ring derivative according to claim 1, which is characterized in that the compound Concrete structure formula are as follows:
In any one.
10. a kind of preparation method of such as compound of the described in any item nitrogen-containing hetero heptatomic ring derivatives of claim 1-9, special Sign is, comprising:
Work as Ar1、Ar2When for singly-bound, the reaction equation that occurs in preparation process are as follows:
Specific preparation process the following steps are included:
1) raw material I and H-R are weighed1, toluene dissolution；Wherein, the raw material I and H-R1Molar ratio be 1:(1.2~1.5)；
2) Pd is added in Xiang Shangshu reaction system2(dba)3, tri-tert-butylphosphine and sodium tert-butoxide, obtain mixed solution；Wherein, Pd2 (dba)3Be (0.006~0.02) with the molar ratio of raw material I: 1, the molar ratio of tri-tert-butylphosphine and raw material I be (0.006~ 0.02): 1, the molar ratio of sodium tert-butoxide and raw material I is (2.0~3.0): 1；
3) under an inert atmosphere, the mixed solution of above-mentioned reactant is reacted 10~24 hours at 95~110 DEG C of reaction temperature, Cooling and filtering reacting solution, filtrate revolving, crosses silicagel column, obtains intermediate II；
4) by intermediate II and H-R2It is dissolved with toluene；Wherein, the intermediate II and the molar ratio of H-R2 be 1:(1.2~ 1.5)；
5) Pd is added into the reaction system in step 4)2(dba)3, tri-tert-butylphosphine and sodium tert-butoxide, obtain mixed solution；Its In, the Pd2(dba)3It is (0.005~0.01) with the molar ratio of intermediate II: 1, the tri-tert-butylphosphine and intermediate II Molar ratio is (0.005~0.02): 1, the molar ratio of the sodium tert-butoxide and intermediate II is (1.5~3.0): 1；
6) under the protection of inert gas, the mixed solution of step 5) reacts to 10 under the conditions of 95~110 DEG C of temperature~ For 24 hours, cooled to room temperature, and filtering reacting solution, filtrate rotate to solvent-free, cross neutral silica gel column, obtain target chemical combination Object；
Work as Ar1、Ar2When not being singly-bound, the reaction equation that occurs in preparation process are as follows:
Specific preparation process the following steps are included:
1) with raw material I and boronic acid compounds R1-Ar1-B(OH)2For raw material, toluene dissolution；Wherein, the toluene dosage is every gram The molar ratio of the use 30-50ml toluene of raw material I, the raw material I and boronic acid compounds is 1:(1.0~1.5)；
2) Pd (PPh is added into the reaction system of step 1)3)4And sodium carbonate, obtain mixed solution；Wherein, the Pd (PPh3)4With The molar ratio of raw material I is (0.005~0.01): 1, the molar ratio of the sodium carbonate and raw material I is (1.5~3.0): 1；
3) it under nitrogen protection, by above-mentioned mixed solution in 95~110 DEG C, reacts 10~24 hours, cooled to room temperature, and Filtering reacting solution, filtrate carry out vacuum rotary steam, cross neutral silica gel column, obtain intermediate III；
4) with intermediate III and boronic acid compounds R2-Ar2-B(OH)2For raw material, toluene dissolution；Wherein, the toluene dosage is every Gram intermediate III uses 30-50ml toluene, and the molar ratio of the intermediate III and boronic acid compounds is 1:(1.0~1.5)；
5) Pd (PPh is added into the reaction system of step 4)3)4And sodium carbonate, obtain mixed solution；Wherein, the Pd (PPh3)4With The molar ratio of intermediate III is (0.005~0.01): 1, the molar ratio of the sodium carbonate and intermediate III is (1.5~3.0): 1；
6) it under nitrogen protection, by the mixed solution of step 5) in 95~110 DEG C, reacts 10~24 hours, naturally cools to room Temperature, and filtering reacting solution, filtrate carry out vacuum rotary steam, cross neutral silica gel column, obtain target compound.
11. a kind of organic electroluminescence device, which is characterized in that at least one layer of functional layer contains any one of claim 1-9 institute The compound for the nitrogen-containing hetero heptatomic ring derivative stated.
12. a kind of organic electroluminescence device according to claim 11, which is characterized in that the functional layer is luminescent layer And/or electronic barrier layer and/or hole transmission layer.
13. a kind of illumination or display element, which is characterized in that including the organic electroluminescence as described in claim 11 or 12 Part.
CN201710900168.1A 2017-09-28 2017-09-28 A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its application on organic electroluminescence device Pending CN109574931A (en)

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CN109574930A (en) * 2017-09-28 2019-04-05 江苏三月光电科技有限公司 A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications
CN109574996A (en) * 2017-09-28 2019-04-05 江苏三月光电科技有限公司 It is a kind of using spiral shell xanthene fluorenes as the compound of core and its application on organic electroluminescence device
CN111499657A (en) * 2020-03-24 2020-08-07 蚌埠学院 Synthetic method of isoquinoline oxazolidine
WO2020262865A1 (en) * 2019-06-24 2020-12-30 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic apparatus thereof

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KR20160091734A (en) * 2015-01-26 2016-08-03 주식회사 두산 Organic light-emitting compound and organic electroluminescent device using the same
CN106688848A (en) * 2016-11-29 2017-05-24 云南省农业科学院药用植物研究所 Efficient exercising technique for Bletilla striata tissue culture seedlings

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KR20160091734A (en) * 2015-01-26 2016-08-03 주식회사 두산 Organic light-emitting compound and organic electroluminescent device using the same
CN106688848A (en) * 2016-11-29 2017-05-24 云南省农业科学院药用植物研究所 Efficient exercising technique for Bletilla striata tissue culture seedlings

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109574930A (en) * 2017-09-28 2019-04-05 江苏三月光电科技有限公司 A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications
CN109574996A (en) * 2017-09-28 2019-04-05 江苏三月光电科技有限公司 It is a kind of using spiral shell xanthene fluorenes as the compound of core and its application on organic electroluminescence device
WO2020262865A1 (en) * 2019-06-24 2020-12-30 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic apparatus thereof
CN111499657A (en) * 2020-03-24 2020-08-07 蚌埠学院 Synthetic method of isoquinoline oxazolidine

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