CN108822021A - Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device - Google Patents

Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device Download PDF

Info

Publication number
CN108822021A
CN108822021A CN201810406960.6A CN201810406960A CN108822021A CN 108822021 A CN108822021 A CN 108822021A CN 201810406960 A CN201810406960 A CN 201810406960A CN 108822021 A CN108822021 A CN 108822021A
Authority
CN
China
Prior art keywords
organic electroluminescence
electroluminescence device
layer
carbon
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
CN201810406960.6A
Other languages
Chinese (zh)
Inventor
不公告发明人
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wang Meini
Original Assignee
Wang Meini
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wang Meini filed Critical Wang Meini
Priority to CN201810406960.6A priority Critical patent/CN108822021A/en
Publication of CN108822021A publication Critical patent/CN108822021A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention relates to field of display technology, contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device more particularly to one kind.Shown in compound according to the present invention such as formula (I)：

Description

Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device And display device
Technical field
The present invention relates to field of display technology, contain unsaturated nitrogenous heterocyclic dihydroanthracene chemical combination more particularly to one kind Object, organic electroluminescence device and display device.
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 following advantages 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 functional 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 hole 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 Hole transmission layer or organic luminous layer make organic electroluminescence device driving voltage with higher and lower luminous efficiency.
Summary of the invention
The present invention provides a kind of containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, includes the organic of the compound Electroluminescent device and display device with the organic electroluminescence device, to solve organic electroluminescent in the prior art The problem of high driving voltage of device and low luminous efficiency.
According to an aspect of the present invention, it provides a kind of containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, the change It closes shown in object such as formula (I)：
Wherein Ar1Unsaturated nitrogen-containing heterocycle, carbon atom 12~40 selected from carbon atoms 3~60 it is unsaturated oxygen-containing The unsaturated sulfur heterocyclic ring of heterocycle, carbon atom 12~40, the Ar1Can by the aliphatic alkyl of carbon atoms 1-30, contain Replaced the aliphatic alkoxy of carbon atom 1-30, the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen.
And Ar1It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen1Direct and dihydro anthracene nucleus On C atom connection, be also possible to Ar1Pass through the C on the aromatic radical being made of carbon and hydrogen and dihydro anthracene nucleus of carbon atom 6-40 Atom connection, is illustrated below：
Work as Ar1Selected from pyridyl group, when the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from phenyl, Ar1Directly and two When C atom on hydrogen anthracene nucleus connects, shown in obtained compound such as formula (II)：
Work as Ar1Selected from pyridyl group, when the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from phenyl, Ar1Pass through carbon original Sub- 6-40's is connected with the aromatic radical that hydrogen forms with the C atom on dihydro anthracene nucleus by carbon, obtained compound such as formula (III) institute Show：
Further, Ar1It is selected from：Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, hexichol And furyl, benzo benzo furyl, dinaphtho furyl, Ar1Can by methyl, ethyl, propyl, butyl, amyl, hexyl, Heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, the third oxygen Base, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, cyclopropyl oxygroup, cyclobutoxy group, penta oxygen of ring Base, cyclohexyloxy, two cyclohexyloxies, phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene replace；The rouge of carbon atom 1-30 Fat race alkyl is selected from：Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, Cyclopenta, cyclohexyl, dicyclohexyl；The aliphatic alkoxy of carbon atoms 1-30 is selected from：Methoxyl group, ethyoxyl, propoxyl group, fourth Oxygroup, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, cyclopropyl oxygroup, cyclobutoxy group, cyclopentyloxy, ring Hexyloxy, two cyclohexyloxies；The aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from：Phenyl, xenyl, naphthalene, anthryl, It is phenanthryl, triphenylene, 9,9- dimethyl fluorenyl, 9,9- diphenyl amyl, Spirofluorene-based.
In addition, of the invention contains unsaturated nitrogenous heterocyclic dihydroanthracene compound, Ar1It can be by carbon atoms 1-30 Aliphatic alkyl, carbon atoms 1-30 aliphatic alkoxy replaced, wherein the substitution, can be monosubstituted, double take Generation or it is polysubstituted.
Optionally, according to the present invention to be selected from containing unsaturated nitrogenous heterocyclic dihydroanthracene compound：
It should be noted that the connection type of adjacent group is unique, such as in P- in specific structure listed above In 50, the phenyl ring contraposition connected on dihydro anthracene nucleus is replaced by dibenzofurans, in fact, between the phenyl ring connected on dihydro anthracene nucleus Position by dibenzofurans replace and dihydro anthracene nucleus on the ortho position of phenyl ring that connects replaced by dibenzofurans and be formed by chemical combination Object, shown in following (a), (b)：
It can achieve effect of the invention, belong to the content of the invention to be disclosed and be protected.Such the position of substitution Change, there is no the main structures for changing the compounds of this invention, without influence on the application technology effect of the compounds of this invention.
Therefore, in the logical formula (I) of the present invention
In, Ar1The change of connection type, belongs to the present invention between representative inside configuration difference or identical group Disclosure and protection within the scope of.
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound comprising according to the present invention.
Optionally, the material of main part of the organic luminous layer of the organic electroluminescence device or/and electron transport material Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound to be according to the present invention.
Optionally, organic electroluminescence device according to the present invention, the organic luminous layer are blue light-emitting layer, green hair Photosphere, Yellow luminous layer or red light emitting layer.
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having Organic electroluminescence devices.
Meanwhile the present invention also provides a kind of electronic equipment, which contains electronic display screen.
Further, above-mentioned electronic equipment is selected from：Mobile phone, computer, tablet computer, wrist-watch, VR display, digital camera, Bracelet, counter, electronic watch.
Beneficial effects of the present invention are as follows：
By compound provided by the invention be used for organic electroluminescence device electron transfer layer or/and organic luminous layer Material of main part, improve 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 compound P-1
In 500 milliliters of there-necked flask, under nitrogen protection, 200 milliliters of dry dimethyl sulfoxides of addition, 1.8 grams Under stirring, the sodium hydride of 3.2 grams of (0.08mol) contents 60% is added portionwise in (0.01mol) 9,10- dihydroanthracene, is stirred in 30 DEG C 30 minutes, 14.04 grams of (0.06mol) 2- phenyl -5- bromopyridines are added, 60 DEG C is warming up to and reacts 1 hour, then be warming up to 80 DEG C Reaction 1 hour, then be warming up to 120 DEG C and react 1 hour, it reheats to 160 DEG C and reacts 8 hours, be down to room temperature, a small amount of methanol point is added Excessive sodium hydride is solved, ammonium chloride solution is then added, is filtered, obtained solid washing, methanol washing, then with silicagel column point From using petroleum ether：Ethyl acetate (volume ratio 3：1) it is eluted as eluant, eluent, obtains product 2.58 shown in formula P-1 Gram, yield 32.6%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：792.
Nuclear-magnetism detection is carried out to obtained compound P-1, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 8.21 (m, 8H), δ 8.17 (d, 4H), δ 7.60 (d, 4H), δ 7.50~7.36 (m, 12H), δ 7.18 (m, 4H), δ 7.13~6.99 (m, 8H).Elemental analysis has been carried out to obtained compound P-1, has been surveyed Value % (C, 87.68；H, 5.10；N, 7.06), calculated value (C, 87.85；H,5.08；N,7.07).
The synthesis of other parts compound of the present invention
Synthetic method referring to P-1 synthetic method, only according to needing to change 2- phenyl -5- bromopyridine therein accordingly into Bromo-derivative has carried out Mass Spectrometer Method to obtained compound, and raw material used in synthesis process and product Mass Spectrometer Method result are shown in Following table：
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device The material of main part or electron transport material of organic luminous layer are according to the compound of the present invention.
Organic electroluminescence device according to the present invention, the organic luminous layer are blue light-emitting layer, green light emitting layer, Huang Color luminescent layer or red light emitting layer.
The typical structure of organic electroluminescence device is：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 HIM 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：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, 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 device is provided, which includes according to the present invention having Organic electroluminescence devices
It can be seen that the optional factor of compound according to the present invention, organic electroluminescence device and display device is more, Claim according to the present invention can be combined into different embodiments.The embodiment of the present invention is only used as to of the invention specific Description, is not intended as limitation of the present invention.Make below in conjunction with the organic electroluminescence device containing the compound of the present invention For embodiment, the present invention is described further.
Different materials specific structure used in the present invention is seen below：
Embodiment 1
Material of main part in using the compound of the present invention as red phosphorescent OLED organic electroluminescence device, 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 To completely removing moisture content, 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 is 100:5；
Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s on luminescent layer, are steamed Plating 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 is shown in Table 1：
Table 1
Can see by upper table, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Embodiment 2
Material of main part in using the compound of the present invention as green phosphorescent OLED organic electroluminescence device, as a comparison Organic electroluminescence device, green light material of main part selects CBP respectively.
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 To completely removing moisture content, 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 is 100:7；
Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s on luminescent layer, are steamed Plating 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 is shown in Table 2：
Table 2
Can see by upper table, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Embodiment 3
Electron transfer layer in using the compound of the present invention as organic electroluminescence device, organic electroluminescence as a comparison Luminescent device, electron transport material select TAZ.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/ETL (20nm)/LiF(0.5nm)/Al(150nm)。
Glass substrate is selected in organic electroluminescence device production in the present embodiment, ITO makees anode material, and HIL02 makees Hole injection layer, NPB make hole transmission layer, and EM1 makees the material of main part of organic luminous layer, and LiF/Al makees electron injecting layer/cathode Material.
Organic electroluminescence device preparation process in the present embodiment 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 passed with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface The binding ability of defeated 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；
The vacuum evaporation NPB on hole injection layer, evaporation rate 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；
The vacuum evaporation electron transport material on organic luminous layer, the electron-transport as organic electroluminescence device Layer；Its evaporation 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 3：
Table 3
It can see by upper table, organic electroluminescence can be improved using the compound of the present invention as electron transfer layer The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
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 (10)

1. one kind is containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, as shown in formula (I)：
Wherein Ar1Unsaturated nitrogen-containing heterocycle selected from carbon atoms 3~60, the Ar1It can be by the fat of carbon atoms 1-30 Race's alkyl, the aliphatic alkoxy of carbon atoms 1-30, carbon atom 6-40 the aromatic radical being made of carbon and hydrogen replaced, and Ar1It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen1C atom directly and on dihydro anthracene nucleus connects It connects, is also possible to Ar1Pass through being connected with the aromatic radical that hydrogen forms with the C atom on dihydro anthracene nucleus by carbon for carbon atom 6-40；
The Ar1Selected from triazine radical.
2. it is according to claim 1 containing unsaturated nitrogenous heterocyclic dihydroanthracene compound,
The Ar1It can be by methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, ring fourth It is base, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, pungent Oxygroup, nonyl epoxide, decyloxy, cyclopropyl oxygroup, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies, phenyl, biphenyl Base, naphthalene, anthryl, phenanthryl, triphenylene replace.
The aliphatic alkyl of carbon atoms 1-30 is selected from：Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl Base, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl；
The aliphatic alkoxy of carbon atoms 1-30 is selected from：Methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, Heptan oxygroup, octyloxy, nonyl epoxide, decyloxy, cyclopropyl oxygroup, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies；
The aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from：Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene, It is 9,9- dimethyl fluorenyls, 9,9- diphenyl amyl, Spirofluorene-based.
3. according to claim 1 contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, Ar1It can be by carbon atoms Replaced the aliphatic alkyl of 1-30, the aliphatic alkoxy of carbon atoms 1-30, wherein the substitution, can be it is monosubstituted, It is disubstituted or polysubstituted.
4. it is according to claim 1 containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, selected from flowering structure：
5. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device contains claim 1-4 Described contains unsaturated nitrogenous heterocyclic dihydroanthracene compound.
6. organic electroluminescence device according to claim 5, which is characterized in that the organic electroluminescence device has The material of main part of machine luminescent layer or/and the material of electron transfer layer are described in claim 1-4 is any containing unsaturated nitrogenous The dihydroanthracene compound of heterocycle.
7. organic electroluminescence device according to claim 6, which is characterized in that the organic luminous layer is blue-light-emitting Layer, green light emitting layer, Yellow luminous layer or red light emitting layer.
8. a kind of display device, which is characterized in that including the organic electroluminescence device as described in claim 5~7 is any.
9. a kind of electronic equipment includes display device described in claim 8.
10. electronic equipment according to claim 9, the electronic equipment is selected from mobile phone, computer, tablet computer, wrist-watch, VR Display, digital camera, bracelet, counter, electronic watch.
CN201810406960.6A 2018-05-01 2018-05-01 Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device Withdrawn CN108822021A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810406960.6A CN108822021A (en) 2018-05-01 2018-05-01 Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810406960.6A CN108822021A (en) 2018-05-01 2018-05-01 Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device

Publications (1)

Publication Number Publication Date
CN108822021A true CN108822021A (en) 2018-11-16

Family

ID=64147734

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810406960.6A Withdrawn CN108822021A (en) 2018-05-01 2018-05-01 Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device

Country Status (1)

Country Link
CN (1) CN108822021A (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103503188A (en) * 2011-05-05 2014-01-08 默克专利有限公司 Compounds for electronic devices

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103503188A (en) * 2011-05-05 2014-01-08 默克专利有限公司 Compounds for electronic devices

Similar Documents

Publication Publication Date Title
CN108586430A (en) A kind of electroluminescent organic material, organic electroluminescence device and display device
CN107936952A (en) A kind of electroluminescent organic material, luminescent device and display
CN108821984A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN108456195A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN108516959A (en) Acridine compound, organic electroluminescence device and display device
CN108329254A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN107973795A (en) A kind of electroluminescent organic material, luminescent device and display
CN108623515A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN109336861A (en) Dihydrobenzo indazole class electroluminescent organic material
CN109206368A (en) A kind of dihydrobenzo indazole class electroluminescent organic material
CN109206367A (en) A kind of organic electroluminescence device and display
CN108586314A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN108586316A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN109206414A (en) Dihydrobenzo indazole class electroluminescent organic material
CN109336862A (en) A kind of organic electroluminescence device and display
CN109206412A (en) A kind of organic electroluminescence device and display
CN109053687A (en) A kind of biindolyl class display material
CN108997318A (en) Biindolyl class electroluminescent organic material
CN108822016A (en) A kind of synthetic method of biindolyl class material
CN108586269A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN108822022A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN108822021A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN108794384A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN108752264A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN109206403A (en) A kind of organic electroluminescence device and display

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20181116