CN109206368A - A kind of dihydrobenzo indazole class electroluminescent organic material - Google Patents

A kind of dihydrobenzo indazole class electroluminescent organic material Download PDF

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CN109206368A
CN109206368A CN201811069181.8A CN201811069181A CN109206368A CN 109206368 A CN109206368 A CN 109206368A CN 201811069181 A CN201811069181 A CN 201811069181A CN 109206368 A CN109206368 A CN 109206368A
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electroluminescence device
organic electroluminescence
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organic material
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李现伟
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Abstract

The present invention relates to field of display technology, more particularly to a kind of dihydrobenzo indazole class electroluminescent organic material, organic electroluminescence device and display.Shown in compound according to the present invention such as formula (A):

Description

A kind of dihydrobenzo indazole class electroluminescent organic material
Technical field
The present invention relates to field of display technology, more particularly to a kind of dihydrobenzo indazole class electroluminescent organic material, Organic electroluminescence device and display.
Background technique
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 adjustable, at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, gives birth to 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 advantage that 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 Adjust thermal stability, mechanical performance, the luminous and electric conductivity of organic material, the space so that material is significantly improved.
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 make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material The difficulty of charge injection and transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer Number, and so that different organic layers is played 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 inject 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 various 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 service life length Usually device architecture and various organic materials optimization collocation as a result, this is just that chemists design and develop various structures Functionalization material provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode, electron injecting layer, electronics being arranged successively from top to bottom Transport layer (Electron transport Layer, abbreviation ETL), organic luminous layer (Emitting Layer, abbreviation EML), Hole transmission layer, hole injection layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly in organic light emission The formation probability of exciton is improved in layer as far as possible, therefore the organic luminous layer of organic electroluminescence device and electronics adjacent thereto pass The material of defeated layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And it is in the prior art The material of main part of material or organic luminous layer that electron transfer layer is used makes organic electroluminescence device driving electricity with higher Pressure and lower luminous efficiency.
Summary of the invention
The present invention provides a kind of dihydrobenzo indazole class electroluminescent organic material, include the organic electroluminescence of the compound Luminescent device and display device with the organic electroluminescence device, to solve organic electroluminescence device in the prior art High driving voltage and the problem of low luminous efficiency.
According to an aspect of the present invention, a kind of dihydrobenzo indazole class electroluminescent organic material, the compound are provided As shown in formula (A):
Wherein Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from the aryl that carbon atom number is 6-30；The Ar1, Aliphatic alkyl that Ar2, Ar3, Ar4, Ar5 can be 1~20 by one or more carbon atom number, carbon atom number 1 ~20 aliphatic alkoxy, the aryl that carbon atom number is 6~30, trimethyl silicon substrate replace, the substitution can be it is monosubstituted, It is disubstituted, polysubstituted.
Further, Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from phenyl, xenyl, naphthalene, fluorenyl, anthracene It is base, phenanthryl, indeno fluorenyl, triphenylene, fluoranthene base, benzo anthryl, benzo fluorenyl, Spirofluorene-based.
Preferably, Ar1, Ar2Selected from phenyl, Ar1, Ar2Contraposition can by carbon atom number be 1~20 aliphatic alkyl, Carbon atom number be 1~20 aliphatic alkoxy, trimethyl silicon substrate replace, it is described substitution can be it is monosubstituted, disubstituted, take more Generation.
It is furthermore preferred that the compounds of this invention is selected from flowering structure:
Meanwhile the present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device contains this hair The bright dihydrobenzo indazole class electroluminescent organic material.
Further, the hole transport layer material of organic electroluminescence device is dihydrobenzo indazole class of the present invention Electroluminescent organic material.
In other embodiment, the hole injection layer material of organic electroluminescence device is dihydrobenzo of the present invention Indazole class electroluminescent organic material.
Meanwhile the present invention also provides a kind of displays, contain organic electroluminescence device of the invention.
Meanwhile the present invention also provides electronic equipment, the electronic equipment display includes organic electroluminescence hair of the invention Optical device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet computer, has electronical display function Electronic entrance ticket, the onboard instruments etc. of energy.
Beneficial effects of the present invention are as follows:
Compound provided by the invention is used in the hole transmission layer or/and hole injection layer of organic electroluminescence device, It improves the luminous efficiency of organic electroluminescence device, reduce the driving voltage of organic electroluminescence device.
Specific embodiment
Specific embodiment is only the description of the invention, without constituting the limitation to the content of present invention, below in conjunction with Invention is further explained and description for specific embodiment.
In order to which the compound of the present invention is explained in more detail, the synthetic method pair of above-mentioned particular compound will be enumerated below The present invention is further described.
The synthesis of 1 compound P-1 of embodiment
It is as follows to synthesize equation:
(1) synthesis of intermediate M-1
In 1000 milliliters of there-necked flask, under nitrogen protection, 500 milliliters of dry toluene, 37.6 grams are added (0.22mol) 4- toluene bromide, 15.6 grams of (0.1mol) 1,2- dihydrobenzo [cd] indazoles, 28.8 grams of (0.3mol) sodium tert-butoxides, 1.26 grams (0.0022mol) bis- (dibenzalacetone) palladiums, 4.4 grams of (0.0022mol) 10% tri-tert-butylphosphine toluene it is molten Liquid is down to room temperature after being heated to back flow reaction 8 hours, water, liquid separation is added, and organic layer is washed with water neutrality, uses anhydrous slufuric acid After magnesium is dry, with silica gel post separation, use petroleum ether: ethyl acetate (volume ratio 5:1) is eluted as eluant, eluent, obtains formula 18.9 grams of product shown in M-1, yield 56.25%.
To obtained compound M-1, Mass Spectrometer Method, product m/e:336 are carried out.
It is as follows to obtained compound M-1 row nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram:
1HNMR (500MHz, CDCl3): δ 8.35 (m, 2H), δ 7.88 (m, 4H), δ 7.65 (m, 6H), δ 7.28 (d, 2H), δ 2.45 (s, 6H).
(2) synthesis of intermediate M-2
In 500 milliliters of there-necked flasks, compound shown in 3.36 grams of (0.01mol) formula M-1 of addition, 30 milliliters of methylene chloride, 0.2 Gram iron powder is cooled to 0~5 DEG C, and 3 milliliters of dichloromethane solutions of 1.76 grams of (0.011mol) bromines are added dropwise.Drop finishes slowly heating It reacts 4 hours, cools down to 25 DEG C, washing, solution of sodium bisulfite washing, silica gel column chromatography point after organic layer magnesium sulfate is dry From petroleum ether: ethyl acetate (volume ratio 50:1) is eluted as eluant, eluent, obtains 1.65 grams of product shown in formula M-2, Yield is 39.76%.
To obtained compound M-2, Mass Spectrometer Method is carried out, product m/e:414,416.
It is as follows to obtained compound M-2 row nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram: 1HNMR (500MHz, CDCl3): δ 8.34 (m, 1H), δ 8.07 (d, 1H), δ 7.89 (d, 4H), δ 7.61 (m, 5H), δ 7.55 (d, 1H), δ 7.28 (m, 1H), δ 2.45 (s, 6H).
(3) synthesis of intermediate M-3:
100 milliliters of dry tetrahydrofurans, 4.15 grams of (0.01mol) formula M-2 are added in 500 milliliters of there-necked flasks, nitrogen protection Shown compound, is cooled to -78 DEG C, and the butyl lithium solution of 7.5 milliliters of (0.012mol) 1.6M is slowly added dropwise, finishes in -78 DEG C It is kept for 1 hour, is slowly added to 1.56 grams of (0.015mol) trimethylborates, be to slowly warm up to 25 DEG C and kept for 2 hours, add ammonium chloride Solution liquid separation, organic layer are concentrated to dryness, and obtain compound shown in formula M-3, without further purifying, directly carry out the next step.
(4) synthesis of intermediate M-4:
500 milliliters of there-necked flasks, nitrogen protection are added 30 milliliters of toluene, 30 milliliters of ethyl alcohol, 20 milliliters of water, walk not in addition Through it is further proposed that formula M-3 shown in compound, add 7.08 grams of (0.03mol) Isosorbide-5-Nitrae-dibromobenzenes, 0.12 gram (0.0001mol) tetrakis triphenylphosphine palladium, 2.76 grams of (0.02mol) potassium carbonate, is warming up to back flow reaction 8 hours, is down to room temperature, Water is added, liquid separation, neutrality is washed with water in organic layer, with anhydrous magnesium sulfate it is dry after, with silica gel post separation, with petroleum ether: second Acetoacetic ester (volume ratio 50:1) is eluted as eluant, eluent, and obtaining 1.66 grams of product, yield shown in formula M-4 is 33.8%.
To obtained compound M-4, Mass Spectrometer Method is carried out, product m/e:490,492.
(5) synthesis of product P-1:
In 500 milliliters of there-necked flask, under nitrogen protection, 100 milliliters of dry toluene, 4.91 grams are added Compound shown in (0.01mol) M-4,2.03 grams of (0.012mol) diphenylamines, 1.25 grams of (0.013mol) sodium tert-butoxides, 0.126 Gram (0.00022mol) bis- (dibenzalacetone) palladiums, 0.44 gram of (0.00022mol) 10% tri-tert-butylphosphine toluene it is molten Liquid is down to room temperature after being heated to back flow reaction 8 hours, water, liquid separation is added, and organic layer is washed with water neutrality, uses anhydrous slufuric acid After magnesium is dry, with silica gel post separation, use petroleum ether: ethyl acetate (volume ratio 10:1) is eluted as eluant, eluent, is obtained 3.91 grams of product shown in formula P-1, yield 67.4%.
To obtained compound P-1, Mass Spectrometer Method, product m/e:579 are carried out.
It is as follows to obtained compound P-1 row nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram:
1HNMR (500MHz, CDCl3): δ 8.33 (m, 1H), δ 8.28 (d, 1H), δ 7.90 (m, 4H), δ 7.62 (m, 5H), δ 7.55 (m, 2H), δ 7.37 (m, 2H), δ 7.32~7.22 (m, 6H), δ 7.09 (m, 4H), δ 7.02 (m, 2H), δ 2.46 (s, 6H).
Embodiment 2
4- toluene bromide therein is only changed into the bromo-derivative of corresponding type by the synthesis of reference compound P-1 as needed, It changes Isosorbide-5-Nitrae-dibromobenzene therein into corresponding two bromo-derivative, changes diphenylamines therein into corresponding aromatic amine, preparation is following Compound has carried out Mass Spectrometer Method to obtained compound.
The type, the type of two bromo-derivatives, the type of aromatic amine of bromo-derivative used and gained compound in preparation process Mass spectrometric data see the table below:
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device Hole injection layer or/and hole transport layer material are according to the compound of the present invention.
The typical structure of organic electroluminescence device are as follows: substrate/anode/hole injection layer/hole transmission layer (HTL)/has Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light Layer is also possible to multi-luminescent layer.
Wherein, the substrate in conventional organic electroluminescence device can be used in substrate, 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 lesser potential barrier with anode, can vacuum evaporation form pin-hole free films.Commonly 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.Commonly 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 level 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 to control exciton in luminescent layer, there are also with phase Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer is needed by taking dyestuff as an example Have following characteristics: there is 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, is able to carry out vapor deposition 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 level 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- triazole) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazole) benzene) or be derived from this three Any two kinds of collocation of kind material.
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, plate 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.Implementation of the invention Example is not intended as limitation of the present invention only as to specific descriptions of the invention.Below in conjunction with contain chemical combination of the invention The present invention is described further as embodiment for the organic electroluminescence device of object.
Different materials specific structure used in the present invention is seen below:
Embodiment 3
Hole-injecting material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison Electroluminescence device, hole-injecting material select HIL02.
Organic electroluminescence device structure are as follows: ITO/ hole injection layer (100nm)/NPB (40nm)/EM1 (30nm)/Alq3 (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 is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface 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 Hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 100nm；
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；
Organic luminous layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam Plating total film thickness is 30nm；
Electron transfer layer 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 used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 1:
Table 1
As can be seen that under identical brightness conditions, using the compound of the present invention as made from hole-injecting material Organic electroluminescence device with using HIL02 as organic electroluminescence device made from hole-injecting material compared with, with compared with Low driving voltage and higher current efficiency.
Embodiment 4
Hole mobile material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison Electroluminescence device, hole mobile material select NPB.
Organic electroluminescence device structure are as follows: ITO/HIL02 (100nm)/hole transmission layer (40nm)/EM1 (30nm)/ Alq3(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 is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface 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 Hole HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness；
Vacuum evaporation material of the present invention and NPB are distinguished on hole injection layer as hole transmission layer, evaporation rate is 0.1nm/s, vapor deposition film thickness are 40nm；
Organic luminous layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam Plating total film thickness is 30nm；
Electron transfer layer 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 used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 2:
Table 2
As can be seen that under identical brightness conditions, using the compound of the present invention as made from hole mobile material Organic electroluminescence device has lower compared with use NPB is as organic electroluminescence device made from hole mobile material Driving voltage and higher current efficiency.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art Mind 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 (4)

1. a kind of dihydrobenzo indazole class electroluminescent organic material, as shown in formula (A):
Wherein Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from the aryl that carbon atom number is 6-30；Ar1, the Ar2, Aliphatic alkyl that Ar3, Ar4, Ar5 can be 1~20 by one or more carbon atom number, carbon atom number are 1~20 Aliphatic alkoxy, carbon atom number be 6~30 aryl, trimethyl silicon substrate replace.
2. dihydrobenzo indazole class electroluminescent organic material according to claim 1, which is characterized in that Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from phenyl, xenyl, naphthalene, fluorenyl, anthryl, phenanthryl, indeno fluorenyl, triphenylene, glimmering It is anthryl, benzo anthryl, benzo fluorenyl, Spirofluorene-based.
3. dihydrobenzo indazole class electroluminescent organic material according to claim 1, wherein Ar1, Ar2Selected from phenyl, Ar1, Ar2Contraposition can be 1~20 by carbon atom number aliphatic alkyl, carbon atom number be 1~20 aliphatic alkoxy, Trimethyl silicon substrate replaces.
4. dihydrobenzo indazole class electroluminescent organic material according to claim 1, which is characterized in that the compound It is selected from:
CN201811069181.8A 2018-09-13 2018-09-13 A kind of dihydrobenzo indazole class electroluminescent organic material Withdrawn CN109206368A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114702432A (en) * 2022-04-01 2022-07-05 上海钥熠电子科技有限公司 Compound containing acenaphthene and application thereof in organic electroluminescent device
CN114716329A (en) * 2022-04-01 2022-07-08 上海钥熠电子科技有限公司 Organic compound and organic photoelectric device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114702432A (en) * 2022-04-01 2022-07-05 上海钥熠电子科技有限公司 Compound containing acenaphthene and application thereof in organic electroluminescent device
CN114716329A (en) * 2022-04-01 2022-07-08 上海钥熠电子科技有限公司 Organic compound and organic photoelectric device

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