CN109574930A - A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications - Google Patents

A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications Download PDF

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CN109574930A
CN109574930A CN201710898906.3A CN201710898906A CN109574930A CN 109574930 A CN109574930 A CN 109574930A CN 201710898906 A CN201710898906 A CN 201710898906A CN 109574930 A CN109574930 A CN 109574930A
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general formula
compound
raw material
nitrogen
molar ratio
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王立春
庞羽佳
张兆超
李崇
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 compounds of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications, belong to technical field of semiconductors.Shown in the structure of organic compound provided by the invention such as general formula (1):The invention also discloses the preparation method and applications of above compound.Compound 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 applications
Technical field
The present invention relates to a kind of compounds of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications, belong to semiconductor Technical field.
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 inventionization It closes object glass transition temperature with higher and molecule thermal stability, suitable HOMO and lumo energy, higher Eg passes through device junction Structure 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 are not simultaneously 0；Ar1、Ar2It is separately expressed as singly-bound, replaces or does not take The C in generation6-60Arlydene contains one or more heteroatomic substituted or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom For nitrogen, oxygen or sulphur；
In general formula (1), R1、R2Separately it is expressed as structure shown in general formula (2)；
Wherein,Be expressed as _,R3And 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, alkyl-substituted imido grpup or the aryl of alkylidene, aryl substitution that linear or branched alkyl group replaces One of substituted imido grpup；
General formula (3) or general formula (4) independently 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 The branch in 9,9 '-spiral shell, the two fluorenes collocation scope of the invention replaced can effectively improve exciton utilization rate and high fluorescent radiation efficiency, The efficiency roll-off under high current density is reduced, device voltage is reduced, improves current efficiency and the service life of device；Of the invention is organic The branch of compound is the seven-members ring structure of dibenzo, this structure has high triplet (T1), as electronic blocking material Material uses, and can effectively stop the exciton energy of luminescent layer to be transferred in hole transmission layer, and it is compound in luminescent layer to improve exciton Efficiency；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 Utilization rate is measured, 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 appoint It anticipates one kind.
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 H-R2Molar ratio 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； 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, above-mentioned mixed solution 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, the toluene dosage is every gram of original Material I uses 30-50ml toluene, wherein the molar ratio of 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, wherein the Pd (PPh3)4With raw material I Molar ratio be (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, the toluene dosage is every Gram intermediate III uses 30-50ml toluene, wherein the molar ratio of the intermediate III and boronic acid compounds be 1:(1.0~ 1.5)；
5) Pd (PPh is added into the reaction system of step (4)3)4And sodium carbonate, wherein the Pd (PPh3)4With centre The molar ratio of body 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 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 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 the current efficiency for making device in illumination or display original set, 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 9,9 '-spiral shell, the two fluorenes collocation scope of the invention that base replaces can effectively improve exciton utilization rate and high fluorescent radiation effect Rate reduces the efficiency roll-off under high current density, reduces device voltage, improves current efficiency and the service life of device；Of the invention The branch of organic compound is the seven-members ring structure of dibenzo, this structure has high triplet (T1), is hindered as electronics Obstructing material uses, and can effectively stop the exciton energy of luminescent layer to be transferred in hole transmission layer, improves exciton in luminescent layer Combined efficiency；When as luminescent layer material of main part, high triplet state can make energy is sufficiently effective to be transferred in dopant material, mention High-energy utilization 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 apply the current efficiency for making device in illumination or display original set, Power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly, in OLED photophore There is good application effect in part, there is 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, I TO anode layer, 3, hole injection layer, 4, hole transport, 5, electronic barrier layer, 6, shine Layer, 7, hole barrier/electron transfer layer, 8, electron injecting layer, 9, cathode reflection electrode layer.
Fig. 2 is the efficiency curve diagram that OLED device of the present 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, 0.1 raw material I, 0.15mol intermediate Y3 of addition, 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。
(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.
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 3:
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 1, 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 95.8%, yield 75.2%.
HRMS (EI): theoretical value 557.2143, measured value 557.2135.
Embodiment 6: the synthesis of compound 7:
Synthetic route:
(1) 0.04mol raw material B1,0.06mol 1,3- bis- is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL Bromobenzene, 0.12mol sodium tert-butoxide, 4 × 10-4mol Pd2(dba)3, 4 × 10-4Mol tri-tert-butylphosphine, 150mL toluene, are heated back Stream 24 hours samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate G1, HPLC Purity 95.1%, yield 77.4%.
(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 97.2%, yield 69.6%.
(3) 0.01mol raw material A 2,0.015mol intermediate is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL H1, (90mL toluene, 45mL ethyl alcohol) is dissolved 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 94.1%, yield 76.6%.
HRMS (EI): theoretical value 633.2457, measured value 633.2463.
Embodiment 7: the synthesis of compound 12:
Synthetic route:
The preparation method of compound 12 is with embodiment 6, the difference is that replacing 1,3- dibromobenzene with Isosorbide-5-Nitrae-dibromobenzene, uses Intermediate C1 replaces raw material B1, replaces raw material A 2 with raw material A 3；Gained target product HPLC purity 92.4%, yield 68.7%.
HRMS (EI): theoretical value 723.2562, measured value 723.2579.
Embodiment 8: the synthesis of compound 28:
Synthetic route:
The preparation method of compound 28 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 2, with intermediate C2 Replace raw material B1；Gained target product HPLC purity 95.1%, yield 70.4%.
HRMS (EI): theoretical value 673.2770, measured value 673.2761.
Embodiment 9: the synthesis of compound 29:
Synthetic route:
The preparation method of compound 29 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 3, with intermediate C2 Replace raw material B1；Gained target product HPLC purity 94.8%, yield 69.5%.
HRMS (EI): theoretical value 673.2770, measured value 673.2784.
Embodiment 10: the synthesis of compound 31:
Synthetic route:
The preparation method of compound 31 is with embodiment 6, the difference is that raw material B1 is replaced with intermediate C2, with raw material A 3 Replace raw material A 2；Gained target product HPLC purity 90.2%, yield 76.8%.
HRMS (EI): theoretical value 749.3083, measured value 749.3065.
Embodiment 11: the synthesis of compound 38:
Synthetic route:
The preparation method of compound 38 is with embodiment 5, the difference is that replacing raw material B1 with intermediate C3；Gained target Product HPLC purity 92.4%, yield 73.7%.
HRMS (EI): theoretical value 673.2770, measured value 673.2777.
Embodiment 12: the synthesis of compound 42:
Synthetic route:
The preparation method of compound 42 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 2, with intermediate C4 Replace raw material B1；Gained target product HPLC purity 95.7%, yield 77.5%.
HRMS (EI): theoretical value 797.3083, measured value 797.3066.
Embodiment 13: the synthesis of compound 54:
Synthetic route:
The preparation method of compound 54 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 2, with intermediate D1 Replace raw material B1；Gained target product HPLC purity 88.5%, yield 70.2%.
HRMS (EI): theoretical value 737.2355, measured value 737.2371.
Embodiment 14: the synthesis of compound 62:
Synthetic route:
The preparation method of compound 62 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 3, with intermediate D2 Replace raw material B1；Gained target product HPLC purity 91.1%, yield 75.7%.
HRMS (EI): theoretical value 789.3396, measured value 789.3412.
Embodiment 15: the synthesis of compound 79:
Synthetic route:
The preparation method of compound 79 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 4, with intermediate C5 Replace raw material B1；Gained target product HPLC purity 93.3%, yield 72.8%.
HRMS (EI): theoretical value 705.2490, measured value 705.2471.
Embodiment 16: the synthesis of compound 84:
Synthetic route:
The preparation method of compound 84 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 2, with intermediate C6 Replace raw material B1；Gained target product HPLC purity 90.7%, yield 73.5%.
HRMS (EI): theoretical value 715.3239, measured value 715.3250.
Embodiment 17: the synthesis of compound 90:
Synthetic route:
The preparation method of compound 90 is with embodiment 5, the difference is that raw material A 1 is replaced with raw material A 2, with intermediate E 1 Replace raw material B1；Gained target product HPLC purity 96.6%, yield 75.2%.
HRMS (EI): theoretical value 673.2406, measured value 673.2426.
Embodiment 18: the synthesis of compound 110:
Synthetic route:
The preparation method of compound 110 is with embodiment 6, the difference is that 1,3- dibromobenzene is replaced with Isosorbide-5-Nitrae-dibromobenzene, Raw material B1 is replaced with intermediate F1；Gained target product HPLC purity 91.7%, yield 74.9%.
HRMS (EI): theoretical value 733.2770, measured value 733.2788.
Embodiment 19: the synthesis of compound 117:
Synthetic route:
The preparation method of compound 117, the difference is that replacing raw material A 1 with raw material A 2, uses intermediate with embodiment 5 F2 replaces raw material B1；Gained target product HPLC purity 93.9%, yield 77.5%.
HRMS (EI): theoretical value 707.2613, measured value 707.2632.
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.The test of hot property, T1 energy level, HOMO energy level, testing result such as 2 institute of table are carried out to the compounds of this invention Show.
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 and minimum occupied molecular orbital lumo energy is surveyed by photoelectron emissions spectrometer (AC-2 type PESA) Examination, is 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.Therefore, originally Invention after the different function layer for being applied to OLED device, can effectively improve device with the compound of nitrogen-containing hetero heptatomic ring derivative Luminous efficiency and service life.
In the devices below by way of device embodiments 1~15 and comparative example 1 OLED material that the present invention will be described in detail synthesizes Application effect.The production work of device embodiments 2~15 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 1-2 is the compounds of this invention as hole mobile material application；Device 3-9 is to be made using material of the present invention For electronic blocking layer material application；Device 10-15 is to use material of the present invention as emitting layer material application.Each embodiment The performance test results of 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 3, 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 7 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 mobile material of electroluminescent device is NPB, Electronic blocking layer material is the compound 12 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 4
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 28 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 5
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 29 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 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 31 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 38 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 42 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 84 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, Luminescent layer material of main part becomes the compound 54 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 9 mass ratio is 10:90, and the detection data of gained electroluminescent device is shown in Table 3.
Device embodiments 11
This 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 become the compound 62 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And change The mass ratio for closing object 9 is 10:90, and 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 79 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 9 mass ratio is 10:90, 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 90 of preparation of the embodiment of the present invention, and dopant material is Ir (ppy)3, Ir (ppy)3And compound 9 mass ratio is 10:90, 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 110 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 9 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 117 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 9 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 1~15 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 18.8 Device embodiments 9 29.7
Device embodiments 2 19.1 Device embodiments 10 40.4
Device embodiments 3 27.7 Device embodiments 11 39.5
Device embodiments 4 26.7 Device embodiments 12 39.6
Device embodiments 5 27.5 Device embodiments 13 40.5
Device embodiments 6 28.2 Device embodiments 14 41.1
Device embodiments 7 27.8 Device embodiments 15 40.7
Device embodiments 8 30.7 Device comparative example 1 8.5
From the data of table 4 it is found that device embodiments 1~15 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 1,7,13 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 1,7,13 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 are not simultaneously 0；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-,=or；R3And 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 atom, selenium are former Son, C1-10Alkylidene, alkyl-substituted imido grpup or the aryl of alkylidene, aryl substitution that linear or branched alkyl group replaces replace One of imido grpup；
General formula (3) or general formula (4) independently 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 in singly-bound One kind.
3. 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 (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 H-R2Molar ratio 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；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 are rubbed You are than being (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, above-mentioned mixed solution reacts to 10 under the conditions of 95~110 DEG C of temperature~for 24 hours, from It is so cooled to room temperature, and filtering reacting solution, filtrate rotates to solvent-free, crosses neutral silica gel column, obtains target compound；
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, the toluene dosage is every gram of raw material I Use 30-50ml toluene, wherein the molar ratio of 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, wherein the Pd (PPh3)4With rubbing for raw material I You are than being (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, the toluene dosage is in every gram Mesosome III uses 30-50ml toluene, wherein 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, wherein the Pd (PPh3)4With intermediate III Molar ratio 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 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 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.
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