CN108191744A - Benzfluorene class electroluminescent organic material, luminescent device and display - Google Patents

Benzfluorene class electroluminescent organic material, luminescent device and display Download PDF

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CN108191744A
CN108191744A CN201711271335.7A CN201711271335A CN108191744A CN 108191744 A CN108191744 A CN 108191744A CN 201711271335 A CN201711271335 A CN 201711271335A CN 108191744 A CN108191744 A CN 108191744A
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carbon atom
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electroluminescence device
organic electroluminescence
aryl
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李现伟
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Abstract

The present invention relates to display technology field, more particularly to benzfluorene class electroluminescent organic material, organic electroluminescence device and display.Shown in compound according to the present invention such as formula (1)：

Description

Benzfluorene class electroluminescent organic material, luminescent device and display
Technical field
The present invention relates to display technology fields, are sent out more particularly to benzfluorene class electroluminescent organic material, organic electroluminescence Optical device and display.
Background technology
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as novel Plate display is compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), has thin, light, wide viewing angle, master It is dynamic shine, luminescent color is continuously adjusted, is at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, raw Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair Luminescent material, electroluminescent organic material have the following advantages：Organic material processing performance is good, can pass through vapor deposition or the side of spin coating Method forms a film on any substrate；The diversity of organic molecular structure allow to by Molecular Design and the method for modification come It adjusts the thermal stability of organic material, mechanical performance, shine and electric conductivity so that material is significantly improved space.
What the generation of organic electroluminescent was leaned on is the carrier (electrons and holes) transmitted in organic semiconducting materials Recombination.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued in organic semiconductor, the transmission of carrier is normal It is described with jump theory.In order to which organic electroluminescence device is made to reach breakthrough in application aspect, it is necessary to overcome organic material Charge injects and the difficulty of transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer Number, and different organic layers is made to play the part of different device layers, such as the functional material having can promote electronics from cathode Injection, some functional materials can promote hole to be injected from anode, and some materials can promote the transmission of charge, and some materials are then It can play the role of stopping electronics or hole transport, the hair of most important a variety of colors certainly in organic electroluminescence device Luminescent material will also achieve the purpose that match with adjacent functional material, therefore, the organic electroluminescence device of excellent in efficiency long lifespan Typically device architecture and various organic materials optimize arranging in pairs or groups as a result, this just designs and develops various structures for chemists Functionalization material provides great opportunities and challenges.
Invention content
The present invention provides benzfluorene class electroluminescent organic material, the organic electroluminescence device comprising the compound and Display device with the organic electroluminescence device.
According to an aspect of the present invention, benzfluorene class electroluminescent organic material, the compound such as formula (1) institute are provided Show：
Wherein X is selected from the aliphatic alkyl that carbon atom number is 1~20, and carbon atom number is the aryl of 6-30, and substituted carbon is former Subnumber is the aryl of 6-30, and the carbon atom on two X can connect cyclization；Y be selected from carbon atom number be 3~10 it is nitrogenous Heterocycle, substituted carbon atom number are 3~10 nitrogen heterocyclic ring； Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It is independently selected from carbon original Aryl of the subnumber for 6-30, and Ar3And Ar4Between can pass through carbon atom thereon connection cyclization, Ar5And Ar6Between can To connect cyclization by carbon atom thereon；Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It can be by one or more carbon atom Count the aryl, three that the aliphatic alkyl for 1~20, the aliphatic alkoxy that carbon atom number is 1~20, carbon atom number are 6~30 Methylsilyl replaces；M, n independence are selected from 0,1.
Further, shown in the compounds of this invention such as formula (2)~formula (5)：
Further, Y be selected from carbon atom number be 3~10 nitrogen heterocyclic ring, substituted carbon atom number be 3~10 it is nitrogenous Heterocycle；Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It is independently selected from the aryl that carbon atom number is 6-30, and Ar3And Ar4Between Can cyclization, Ar be connected by carbon atom thereon5And Ar6Between can pass through carbon atom thereon connection cyclization；Ar1, Ar2, Ar3, Ar4, Ar5, Ar6Can be 1 by aliphatic alkyl that one or more carbon atom number is 1~20, carbon atom number~ 20 aliphatic alkoxy, the aryl that carbon atom number is 6~30, the substitution of trimethyl silicon substrate；M, n independence are selected from 0,1.
Further, Y is selected from triazine, the benzene that pyridine, quinoline, pyrimidine, triazine, the aryl that carbon atom number is 6-30 replace And the benzimidazole that the aryl that imidazoles, carbon atom number are 6-30 replaces；Ar1, Ar2, Ar3, Ar4, Ar5, Ar6Choosing independently From phenyl, naphthalene, xenyl, fluorenyl, Spirofluorene-based, dibenzofuran group, dibenzothiophene, carbazyl, N- phenyl carbazoles base, Phenanthryl, indeno carbazyl, two indeno carbazyls；Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It can be by one or more carbon original Aryl that aliphatic alkoxy that aliphatic alkyl that subnumber is 1~20, carbon atom number are 1~20, carbon atom number are 6~30, Trimethyl silicon substrate replaces；M, n independence are selected from 0,1.
Optionally, electroluminescent organic material according to the present invention is selected from：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Benzfluorene class electroluminescent organic material containing the present invention.
Optionally, the guest materials of the organic luminous layer of the organic electroluminescence device and/or hole mobile material and/ Or material of main part is the electroluminescent organic material according to the present invention.Optionally, benzfluorene class organic electroluminescence according to the present invention Luminescent material is blue-fluorescence guest materials in organic electroluminescence device.Optionally, benzfluorene class according to the present invention has Electroluminescent material is phosphorescent light body material in organic electroluminescence device.
According to another aspect of the present invention, a kind of display is provided, which includes according to the present invention organic Electroluminescent device.
According to another aspect of the present invention, a kind of electronic equipment is provided, the electronic equipment display includes the present invention The organic electroluminescence device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet electricity Brain, the electronic entrance ticket with electronic display function, onboard instruments.
Beneficial effects of the present invention are as follows：
Compound provided by the invention can be used in the guest materials and/or hole mobile material of organic electroluminescence device And/or material of main part.
Specific embodiment
Specific embodiment is only the description of the invention, without forming the limitation to the content of present invention, below in conjunction with Specific embodiment is further described and describes to the present invention.
In order to which the compound of the present invention is explained in more detail, synthetic method pair that will enumerate above-mentioned particular compound below The present invention is further described.
The synthesis of 1 compound A-1 of embodiment
It is as follows to synthesize equation：
The synthesis of intermediate M-1
1000 milliliters of there-necked flasks, nitrogen protection, add in chloro- 7, the 7- bis- of the bromo- 5- of 9- shown in 35.7 grams of (0.1mol) formula M-0 Methyl -7H- benzos [c] fluorenes (is purchased from Hebei Delongtai Chemicals Co., Ltd.), and 400 milliliters of dry tetrahydrofurans are cooled to -78 DEG C, the hexane solution of the butyl lithium of 62.5 milliliters of (0.1mol) 1.6mol/L is slowly added dropwise, is added dropwise, is kept for -78 DEG C 30 Minute, 20.9 grams of (0.11mol) triisopropyl borate esters are then added dropwise, finish, are slowly raised to room temperature, is kept for 3 hours, is slowly added to Dilute hydrochloric acid, liquid separation, organic layer are concentrated to dryness, and obtain chloro- 7,7- dimethyl -7H- benzos [c] fluorenes -9- boric acid of 5- shown in formula M-01, Directly carry out the next step.
In the 1000 milliliters of there-necked flasks protected to nitrogen, chloro- 7, the 7- bis- of 5- shown in the formula M-01 being prepared are walked in addition Methyl -7H- benzos [c] fluorenes -9- boric acid, 15.8 grams of (0.1mol) 3- bromopyridines, 200 milliliters of toluene, 200 milliliters of ethyl alcohol, 160 Milliliter 27.6 grams of (0.2mol) potassium carbonate of water, 5.78 grams of (0.005mol) tetra-triphenylphosphine palladiums finish and are to slowly warm up to 70 DEG C, instead It answers 4 hours, cools down.Add moisture liquid, organic layer washing, anhydrous sodium sulfate is dried, and silicagel column decolorization, eluent is concentrated into It is dry, obtain intermediate M-1 crude products.It is dry by above-mentioned M-1 crude products recrystallizing methanol, 25.5 grams of intermediate M-1 fine work is obtained, Yield 71.63%.
MS tests, molecular weight product m/e are carried out to intermediate shown in obtained formula M-1：355.
Nuclear-magnetism detection is carried out to intermediate shown in obtained formula M-1, the parsing data of obtained nuclear-magnetism figure are as follows：
1HNMR (500MHz, CDCl3)：δ 9.24 (d, 1H), δ 8.83 (m, 1H), δ 8.70 (m, 1H), δ 8.43 (d, 1H), δ 8.33 (m, 1H), δ 8.19 (m, 1H), δ 8.12 (d, 1H), δ 7.97 (m, 1H), δ 7.71 (s, 1H), δ 7.47 (t, 1H), δ 7.32 (m, 2H), δ 1.75 (s, 6H).
The synthesis of compound A--1
In 500 milliliters of there-necked flask, under nitrogen protection, add in 120 milliliters of dry toluene, 10.68 grams Intermediate shown in (0.03mol) formula M-1,5.58 grams of (0.033mol) diphenylamines, 3.84 grams of (0.04mol) sodium tert-butoxides, 0.56 Gram (0.001mol) bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-tert-butylphosphine toluene solution, add Heat is down to room temperature after 16 hours to back flow reaction, adds in dilute hydrochloric acid, liquid separation, and organic layer is washed with water neutrality, uses anhydrous slufuric acid After magnesium drying, with silica gel post separation, petroleum ether is used：Ethyl acetate (volume ratio 5：5) it is eluted as eluant, eluent, obtains formula 8.8 grams of product shown in A-1, yield 60.1%.
To obtained compound A-1, Mass Spectrometer Method, product m/e are carried out：488.
Nuclear-magnetism detection is carried out to product shown in obtained formula A-1, the parsing data of obtained nuclear-magnetism figure are as follows：1HNMR (500MHz, CDCl3)：δ 9.24 (d, 1H), δ 8.85 (m, 1H), δ 8.70 (m, 1H), δ 8.43 (d, 1H), δ 8.33 (m, 1H), δ 8.15 (m, 1H), δ 8.11 (d, 1H), δ 7.97 (m, 1H), δ 7.58 (s, 1H), δ 7.47 (t, 1H), δ 7.32~7.20 (m, 6H), δ 7.08 (m, 4H), δ 7.00 (m, 2H), δ 1.74 (s, 6H).
Embodiment 2
The synthesis of reference compound A-1 is reacted using intermediate M-1 and corresponding diarylamines, prepares following chemical combination Object has carried out Mass Spectrometer Method to obtained compound, and mass spectrometric data see the table below：
The synthesis of 3 compound B-1 of embodiment
The synthesis of reference compound A-1 only changes chloro- 7,7- dimethyl -7H- benzos [c] fluorenes of the bromo- 5- of 9- therein into Chloro- 7,7- diphenyl -7H- benzos [c] fluorenes of the bromo- 5- of 9- shown in formula M-02 (is purchased from Hebei Delongtai Chemicals Co., Ltd.), prepares Obtain compound B-1.
To obtained compound B-1, Mass Spectrometer Method, product m/e are carried out：612.
Nuclear-magnetism detection is carried out to product shown in obtained formula B-1, the parsing data of obtained nuclear-magnetism figure are as follows：1HNMR (500MHz, CDCl3)：δ 9.24 (d, 1H), δ 8.92 (m, 1H), δ 8.71 (m, 1H), δ 8.43 (d, 1H), δ 8.33 (m, 2H), δ 8.16 (m, 1H), δ 7.97 (m, 1H), δ 7.78 (s, 1H), δ 7.47 (t, 1H), δ 7.36~7.16 (m, 12H), δ 7.12 ~7.06 (m, 8H), δ 7.00 (m, 2H),.
Embodiment 4
The synthesis of reference compound B-1 is reacted using intermediate M-2 and corresponding diarylamines, prepares following chemical combination Object has carried out Mass Spectrometer Method to obtained compound, and mass spectrometric data see the table below：
The synthesis of 5 compound C-1 of embodiment
The synthesis of reference compound A-1 only changes chloro- 7,7- dimethyl -7H- benzos [c] fluorenes of the bromo- 5- of 9- therein into The bromo- 5- chlorine spiral shells of 9- shown in M-03 [benzo [c] fluorenes -7,9'- fluorenes] (are purchased from Hebei Delongtai Chemicals Co., Ltd.), being prepared Close object C-1.
To obtained compound C-1, Mass Spectrometer Method, product m/e are carried out：610.
Nuclear-magnetism detection is carried out to product shown in obtained formula C-1, the parsing data of obtained nuclear-magnetism figure are as follows：1HNMR (500MHz, CDCl3)：δ 9.24 (d, 1H), δ 8.90 (m, 1H), δ 8.70 (m, 1H), δ 8.43 (d, 1H), δ 8.38 (m, 1H), δ 8.15 (m, 2H), δ 7.97 (m, 1H), δ 7.89 (m, 2H), δ 7.70 (m, 2H), δ 7.60 (s, 1H), δ 7.47 (t, 1H), δ 7.36~7.23 (m, 10H), δ 7.07 (m, 4H), δ 7.01 (m, 2H).
Embodiment 6
The synthesis of reference compound C-1 is reacted using intermediate M-3 and corresponding diarylamines, prepares following chemical combination Object has carried out Mass Spectrometer Method to obtained compound, and mass spectrometric data see the table below：
The synthesis of 7 compound D-1 of embodiment
The synthesis of reference compound A-1 only changes chloro- 7,7- dimethyl -7H- benzos [c] fluorenes of the bromo- 5- of 9- therein into The bromo- 5- chlorine spiral shells of 9- shown in M-04 [benzo [c] fluorenes -7,1'- hexamethylene] (are purchased from Hebei Delongtai Chemicals Co., Ltd.), are prepared into To compound D-1.
To obtained compound D-1, Mass Spectrometer Method, product m/e are carried out：528.
Nuclear-magnetism detection is carried out to product shown in obtained formula D-1, the parsing data of obtained nuclear-magnetism figure are as follows：1HNMR (500MHz, CDCl3)：δ 9.26 (d, 1H), δ 8.86 (m, 1H), δ 8.71 (m, 1H), δ 8.43 (d, 1H), δ 8.33 (m, 1H), δ 8.15 (m, 1H), δ 8.12 (d, 1H), δ 7.97 (m, 1H), δ 7.58 (s, 1H), δ 7.47 (t, 1H), δ 7.30~7.20 (m, 6H), δ 7.08 (m, 4H), δ 7.00 (m, 2H), δ 2.41 (m, 2H), δ 2.17 (m, 2H), δ 1.50 (m, 6H).
Embodiment 8
The synthesis of reference compound D-1 is reacted using intermediate M-4 and corresponding diarylamines, prepares following chemical combination Object has carried out Mass Spectrometer Method to obtained compound, and mass spectrometric data see the table below：
Embodiment 9
The synthesis of reference compound A-1 only changes 3- bromopyridines therein into corresponding bromo-derivative, by it as needed In diphenylamines change corresponding diarylamines compound into and prepare following compound, mass spectrum has been carried out to obtained compound Detection, mass spectrometric data see the table below：
The synthesis of 10 compound F-1 of embodiment
The synthesis of reference compound A-1 only changes 3- bromopyridines therein into bromo- 4, the 6- diphenyl -1,3 of 2-, 5- tri- Piperazine changes diphenylamines therein into two (3,4- 3,5-dimethylphenyl) amine, compound F-1 is prepared.
To obtained compound F-1, Mass Spectrometer Method, product m/e are carried out：698.
Nuclear-magnetism detection is carried out to product shown in obtained formula F-1, the parsing data of obtained nuclear-magnetism figure are as follows：1HNMR (500MHz, CDCl3)：δ 8.85 (m, 1H), δ 8.43 (d, 1H), δ 8.37 (m, 5H), δ 8.15 (m, 1H), δ 7.97 (m, 1H), δ 7.59 (s, 1H), δ 7.51 (m, 6H), δ 7.26 (m, 2H), δ 7.20 (d, 2H), δ 7.03 (m, 2H), δ 6.95 (d, 2H), δ 2.21 (s, 6H), δ 2.19 (s, 6H), δ 1.75 (s, 6H).
Embodiment 11
The synthesis of reference compound F-1, only as needed by bromo- 4, the 6- diphenyl -1,3 of 2- therein, 5- triazines are changed Into corresponding bromo-derivative, it is following to change therein two (3,4- 3,5-dimethylphenyl) amine into corresponding diarylamines compound preparation Compound has carried out obtained compound Mass Spectrometer Method, and the mass spectrometric data for preparing gained compound see the table below：
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device Guest materials and/or hole mobile material and/or material of main part are the electroluminescent organic material according to the present invention.
The typical structure of organic electroluminescence device is：Substrate/anode/hole injection layer/hole transmission layer (HTL)/has Machine luminescent layer material of main part：Luminescent layer guest materials/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescent Device architecture can be that single-shot photosphere can also be multi-luminescent layer.
Wherein, substrate can use the substrate in conventional organic electroluminescence device, such as：Glass or plastics.Anode can be with Using transparent high conductivity material, such as：Indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO)。
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable that there is height Thermal stability (high Tg), have a smaller potential barrier with anode, can vacuum evaporation form pin-hole free films.Common HTM is Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
The hole mobile material (Hole Transport Material, abbreviation HTM) of hole transmission layer, it is desirable that there is height Thermal stability (high Tg), higher cavity transmission ability, can vacuum evaporation formed pin-hole free films.Common HTM is Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, such as is contaminated Material, material of main part need to have following characteristics：Reversible electrochemical redox current potential, with adjacent hole transmission layer and electronics The HOMO energy levels and lumo energy that transport layer matches, the good and hole to match and electron transport ability are good high Thermal stability and film forming and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer, also with phase Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer by taking dyestuff as an example, needs Have following characteristics：With high fluorescence or phosphorescence quantum efficiency；The absorption spectrum of dyestuff and the emission spectrum of main body have Overlapping, i.e. main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff；The emission peak of red, green, blue to the greatest extent may be used Can be narrow, with the excitation purity obtained；Stability is good, can be deposited etc..
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy levels and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with Hole blocking ability；Higher electron transport ability, the film forming and thermal stability having had.ETM is typically electron deficient knot The aromatic compound of the conjugate planes of structure.Electron transfer layer uses Alq3 (8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4- (1 '-naphthalene) -5- benzene -1,2,4- triazoles) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazoles) benzene) or it is derived from this Arbitrary two kinds of collocation of three kinds of materials.
According to another aspect of the present invention, a kind of display is provided, which includes Organic Electricity according to the present invention Electroluminescence device.
According to another aspect of the present invention, a kind of electronic equipment is provided, the electronic equipment display includes the present invention The organic electroluminescence device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet electricity Brain, the electronic entrance ticket with electronic display function.
It can be seen that compound according to the present invention, organic electroluminescence device, display and the electricity with display device The optional factor of sub- device is more, and claim according to the present invention can be combined into different embodiments.The implementation of the present invention Example only as the specific descriptions to the present invention, is not intended as limitation of the present invention.Below in conjunction with the chemical combination containing the present invention The present invention is described further as embodiment for the organic electroluminescence device of object.
The different materials concrete structure used in the present invention is seen below：
Embodiment 12
Luminescent layer guest materials in using the compound of the present invention as organic electroluminescence device, as a comparison organic Electroluminescent device, luminescent layer guest materials select BD-1 and BD-2.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/NPB(40nm)/EM1：Luminescent layer guest materials [5%] (30nm)/ETL (20nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely Water with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface, to improve the property on surface, is improved and is noted with hole Enter the binding ability of layer；
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness；
Vacuum evaporation NPB is as hole transmission layer on hole injection layer, and evaporation rate 0.1nm/s, film thickness, which is deposited, is 40nm；
Vacuum evaporation light emitting host material and guest materials on hole transmission layer, as organic electroluminescence device Luminescent layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；Wherein EM1：Luminescent layer guest materials [5%] " refers to send out The weight part ratio of the doping ratio of photosphere guest materials, i.e. material of main part and luminescent layer guest materials is 100:5；
Electron transfer layers of the vacuum evaporation Alq3 as organic electroluminescence device on organic luminous layer；Speed is deposited in it Rate is 0.1nm/s, and vapor deposition total film thickness is 20nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is as cathode on electron injecting layer.
Organic electroluminescence device performance see the table below：
As can be seen that under identical brightness conditions, compound using the present invention is made as luminescent layer guest materials Organic electroluminescence device with using BD-1 and BD-2 as organic electroluminescence device phase made from luminescent layer guest materials Than having relatively low driving voltage and higher current efficiency.
Embodiment 13
Material of main part in using the compound of the present invention as red phosphorescent OLED organic electroluminescence devices, as a comparison Organic electroluminescence device, feux rouges material of main part select CBP.
Organic electroluminescence device structure is：ITO/NPB (20nm)/feux rouges material of main part (30nm)：Ir(piq) 3 [5%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；Wherein " Ir (piq) 3 [5%] " refers to the doping ratio of red dye The weight part ratio of example, i.e. feux rouges material of main part and Ir (piq) 3 are 100:5；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, It is respectively 10nm and 15nm that film thickness, which is deposited,；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that, using chemical combination of the present invention as red phosphorescent main body organic electroluminescence device relative to Preferable effect is obtained as the organic electroluminescence device of main body using CBP, obtains higher current efficiency and relatively low Driving voltage.
Embodiment 14
Material of main part in using the compound of the present invention as green phosphorescent OLED organic electroluminescence devices, as a comparison Organic electroluminescence device, green light material of main part select CBP.
Organic electroluminescence device structure is：ITO/NPB (20nm)/green light material of main part (30nm)：Ir(ppy) 3 [7%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；Wherein " Ir (ppy) 3 [7%] " refers to the doping ratio of green light dyestuff The weight part ratio of example, i.e. green light material of main part and Ir (ppy) 3 are 100:7；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, It is respectively 10nm and 15nm that film thickness, which is deposited,；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that, using chemical combination of the present invention as green phosphorescent main body organic electroluminescence device relative to Preferable effect is obtained as the organic electroluminescence device of main body using CBP, obtains higher current efficiency and relatively low Driving voltage.
Embodiment 15
Hole mobile material in using the compound of the present invention as red phosphorescent OLED organic electroluminescence devices, as The organic electroluminescence device of comparison, hole mobile material use NPB.
Organic electroluminescence device structure is：ITO/ hole mobile materials (20nm)/CBP (30nm)：Ir(piq) 3 [5%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation hole transmission layer on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；Wherein " Ir (piq) 3 [5%] " refers to the doping ratio of red dye The weight part ratio of example, i.e. feux rouges material of main part and Ir (piq) 3 are 100:5；
The vacuum evaporation electron transfer layer on luminescent layer, electron transfer layer use TPBI and Alq3, and evaporation rate is equal For 0.1nm/s, vapor deposition film thickness is respectively 10nm and 15nm；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that：Using chemical combination of the present invention as hole mobile material organic electroluminescence device relative to Using organic electroluminescence devices of the NPB as hole mobile material, higher current efficiency and relatively low driving electricity are obtained Pressure.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art God and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies Within, then the present invention is also intended to include these modifications and variations.

Claims (10)

1. benzfluorene class electroluminescent organic material, which is characterized in that shown in the compound such as formula (1)：
Wherein X is selected from the aliphatic alkyl that carbon atom number is 1~20, aryl of the carbon atom number for 6-30, substituted carbon atom number For the aryl of 6-30, and the carbon atom on two X can connect cyclization；
Y is selected from the nitrogen heterocyclic ring that carbon atom number is 3~10, and substituted carbon atom number is 3~10 nitrogen heterocyclic ring,
Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It is independently selected from the aryl that carbon atom number is 6-30, and Ar3And Ar4Between can To connect cyclization, Ar by carbon atom thereon5And Ar6Between can pass through carbon atom thereon connection cyclization；The Ar1, Ar2, Ar3, Ar4, Ar5, Ar6Can be by aliphatic alkyl that one or more carbon atom number is 1~20, carbon atom number 1~20 aliphatic alkoxy, the aryl that carbon atom number is 6~30, the substitution of trimethyl silicon substrate；
M, n independence are selected from 0,1.
2. benzfluorene class electroluminescent organic material according to claim 1, which is characterized in that the compound such as formula (2) shown in~formula (5)：
Y is selected from the nitrogen heterocyclic ring that carbon atom number is 3~10, and substituted carbon atom number is 3~10 nitrogen heterocyclic ring；
Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It is independently selected from the aryl that carbon atom number is 6-30, and Ar3And Ar4Between can To connect cyclization, Ar by carbon atom thereon5And Ar6Between can pass through carbon atom thereon connection cyclization；The Ar1, Ar2, Ar3, Ar4, Ar5, Ar6Can be by aliphatic alkyl that one or more carbon atom number is 1~20, carbon atom number 1~20 aliphatic alkoxy, the aryl that carbon atom number is 6~30, the substitution of trimethyl silicon substrate；
M, n independence are selected from 0,1.
3. benzfluorene class electroluminescent organic material according to claim 3, wherein：
Y is selected from triazine, benzimidazole, the carbon atom number that pyridine, quinoline, pyrimidine, triazine, the aryl that carbon atom number is 6-30 replace The benzimidazole that aryl for 6-30 replaces；
Ar1, Ar2, Ar3, Ar4, Ar5, Ar6It is independently selected from phenyl, naphthalene, xenyl, fluorenyl, Spirofluorene-based, dibenzo furan It mutters base, dibenzothiophene, carbazyl, N- phenyl carbazoles base, phenanthryl, indeno carbazyl, two indeno carbazyls；
The Ar1, Ar2, Ar3, Ar4, Ar5, Ar6Can by one or more carbon atom number be 1~20 aliphatic alkane Aryl that aliphatic alkoxy that base, carbon atom number are 1~20, carbon atom number are 6~30, the substitution of trimethyl silicon substrate；
M, n independence are selected from 0,1.
4. benzfluorene class electroluminescent organic material according to claim 1, which is characterized in that the compound is selected from：
5. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device contains claim 1-4 The benzfluorene class electroluminescent organic material.
6. organic electroluminescence device according to claim 5, which is characterized in that the visitor of the organic electroluminescence device Body material is any benzo fluorene analogue electroluminescent materials of claim 1-4.
7. organic electroluminescence device according to claim 5, which is characterized in that the sky of the organic electroluminescence device Hole transport materials are any benzo fluorene analogue electroluminescent materials of claim 1-4.
8. organic electroluminescence device according to claim 5, which is characterized in that the master of the organic electroluminescence device Body material is any benzo fluorene analogue electroluminescent materials of claim 1-4.
9. a kind of display, which is characterized in that including the organic electroluminescence device as described in claim 5-8 is any.
10. a kind of electronic equipment, the electronic equipment display includes the organic electroluminescent as described in claim 5-7 is any Device；
The electronic equipment include TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet computer, with electronic display function Electronic entrance ticket, onboard instruments.
CN201711271335.7A 2017-12-05 2017-12-05 Benzfluorene class electroluminescent organic material, luminescent device and display Pending CN108191744A (en)

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JP2021014444A (en) * 2019-07-12 2021-02-12 長春海譜潤斯科技有限公司 Amine derivative and organic electroluminescent element thereof
WO2022100704A1 (en) * 2020-11-13 2022-05-19 阜阳欣奕华材料科技有限公司 Compound, organic electroluminescent apparatus and display device

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WO2019185061A1 (en) * 2018-03-29 2019-10-03 江苏三月光电科技有限公司 Bis(dimethylfluorene)-based compound, preparation method therefor and use thereof
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