CN108558731A - Biindolyl class material containing triaryl amine group - Google Patents
Biindolyl class material containing triaryl amine group Download PDFInfo
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Abstract
The present invention relates to Material Fields, more particularly to a kind of application of the biindolyl class material in organic electroluminescence device and display device containing triaryl amine group.Shown in compound according to the present invention such as formula (1)：
Description
Technical field
The present invention relates to Material Fields, more particularly to a kind of biindolyl class material containing triaryl amine group and its are having
Application in organic electroluminescence devices and display device.
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 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：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, the transmission of carrier normal in organic semiconductor
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
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.Certainly in organic electroluminescence device, most important a variety of colors
Luminescent material will also achieve the purpose that match with adjacent functional material.Therefore, the organic electroluminescence of excellent in efficiency long lifespan
Part is typically device architecture and various organic materials optimize arranging in pairs or groups as a result, this, which is just chemists, designs and develops various structures
Functionalization material provide great opportunities and challenges.
In organic electroluminescence device preparation process, one kind being known as vapour deposition method, i.e., each functional material passes through vacuum
The mode of hot evaporation is plated on substrate and forms a film, this is also the mainstream technology of current industry.But the shortcomings that this technique it is also obvious that
The characteristic of one side organic material itself determines, hot evaporation is carried out under the high temperature conditions for a long time, to the thermal stability of material
It is required that very high；In addition prolonged stability contorting evaporation rate, keep thereon material distribution uniformity be also one very
Important requirement；And high vacuum, high temperature deposition, energy consumption are higher；It is more main, because OLED material production technology itself compares
Complexity, technology content is higher, thus price is more expensive, and prior art is used by vapor deposition mode, the utilization of OLED material
Rate is relatively low, generally below 10%.
In the preparation process of organic electroluminescence device, another is known as solwution method, that is, uses soluble OLED materials
Material, is dissolved in solvent, is coated on substrate by modes such as printing, ink-jet, spin coatings, such to form certain functional layers
Method material is evenly distributed, and saves material, simplifies OLED device production technology, reduces OLED device production cost.
Invention content
The present invention provides a kind of biindolyl class material containing triaryl amine group, the hair of the organic electroluminescence comprising the compound
Optical device and display device with the organic electroluminescence device, including the organic electroluminescence device of the compound have compared with
Low driving voltage and higher luminous efficiency.
And the biindolyl class material provided by the invention containing triaryl amine group has preferable molten in organic solvent
Xie Xing, and have good film forming.In organic electroluminescence device preparation, hole injection layer can be formed by solwution method.
According to an aspect of the present invention, a kind of biindolyl class material containing triaryl amine group is provided, such as formula (1) institute
Show：
Wherein Ar1, Ar2The independent aryl being made of carbon and hydrogen selected from C6~C40, B-1,
In B-1, Ar3, Ar4, Ar5The independent aryl being made of carbon and hydrogen selected from C6~C40, in B-1 * indicate B-1 and
The position of the N atoms connection connected on phenyl ring in formula (1)；And Ar1, Ar2, Ar3, Ar4, Ar5It can be by the alkane of C1~C20
The aryl of base, the alkoxy of C1~C20, C6~C40 being made of carbon and hydrogen is replaced；The substitution can be it is monosubstituted, it is double
Substitution, it is polysubstituted.
Further, the biindolyl class material provided by the invention containing triaryl amine group, the aryl choosing of wherein C6~C40
From：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, fluorenyl, fluoranthene base, indeno fluorenyl, it is Spirofluorene-based,
Benzo fluorenyl, dibenzo fluorenyl, phenyl substituted naphthyl, benzo anthryl；The alkyl of C1~C20 is selected from methyl, ethyl, propyl, fourth
Base, amyl, hexyl, cyclohexyl, heptyl, octyl；The alkoxy of C1~C20 be selected from methoxyl group, ethyoxyl, propoxyl group, butoxy,
Amoxy, hexyloxy, cyclohexyloxy, oxygroup in heptan, octyloxy.
Further, the biindolyl class material provided by the invention containing triaryl amine group, selected from lower structure：
According to another aspect of the present invention, a kind of solution is provided, wherein at least contains triaryl amine comprising of the present invention
The biindolyl class material of group and at least one solvent.The solvent be selected from toluene, dimethylbenzene, chlorobenzene, dichloro-benzenes, diphenyl ether,
It is more than one or two kinds of in chloroform, ethyl acetate, ethyl alcohol, isopropanol, n-butanol.
The preparation method of the solution is：In glove box, under nitrogen atmosphere, the compounds of this invention is dissolved in above-mentioned molten
In agent, then passes through 0.1 micron of membrane filtration and obtain.
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided
Including the biindolyl class material according to the present invention containing triaryl amine group.
Optionally, the hole-injecting material of the organic electroluminescence device is to contain triaryl amine group according to the present invention
Biindolyl class material.
Optionally, the hole mobile material of the organic electroluminescence device is to contain triaryl amine group according to the present invention
Biindolyl class material.
Optionally, the hole injection layer of the organic electroluminescence device is prepared by solwution method.
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.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used as to the hole-injecting material or hole transport material of organic electroluminescence device
Material, improves the luminous efficiency of organic electroluminescence device, reduces the driving voltage of organic electroluminescence device.
During preparing organic electroluminescence device, compound provided by the invention is formed into hole by solwution method
Implanted layer, obtained organic electroluminescence device have lower driving voltage and higher luminous efficiency.
Specific implementation mode
Specific implementation mode 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.
The present invention provides a kind of biindolyl class material containing triaryl amine group, the hair of the organic electroluminescence comprising the compound
Optical device and display device with the organic electroluminescence device, including the organic electroluminescence device of the compound have compared with
Low driving voltage and higher luminous efficiency.
And the biindolyl class material provided by the invention containing triaryl amine group has appropriate molten in organic solvent
Xie Xing, and have good film forming.In organic electroluminescence device preparation, hole injection layer can be formed by solwution method,
The organic electroluminescence device arrived has lower driving voltage and higher luminous efficiency.
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：
In 500 milliliters of there-necked flasks, under nitrogen protection, it is added in 300 milliliters of dry toluene, 28.5 grams (0.05mol)
Compound shown in mesosome 1,20.28 grams of (0.12mol) diphenylamines, 14.4 grams of (0.15mol) sodium tert-butoxides, 0.58 gram
(0.001mol) bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-tert-butylphosphine toluene solution, heating
Room temperature is down to after 8 hours to back flow reaction, dilute hydrochloric acid, liquid separation is added, neutrality is washed with water in organic layer, dry with anhydrous magnesium sulfate
After dry, silica gel post separation, ethyl acetate are crossed：Petroleum ether=1：5 (volume ratios) elute, and eluent is concentrated to dryness, and uses methanol/toluene
Mixed solvent recrystallizes, and obtains 28.6 grams of compound shown in formula P-1, yield 76.58%.
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e of product：746.
Nuclear-magnetism detection is carried out to product shown in obtained formula P-1, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 7.82 (m, 2H), δ 7.56 (m, 4H), δ 7.51 (m, 2H), δ 7.37 (m, 4H), δ
7.33~7.21 (m, 10H), δ 7.11~6.92 (m, 14H), δ 3.81 (s, 6H).
The synthesis of 2 other parts compound of embodiment
The synthetic method of reference compound P-1 only changes diphenylamines therein into corresponding aromatic amine as needed.Tool
Aromatic amine and mass spectrometric data used in precursor reactant are listed as follows：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided
Hole-injecting material be according to the present invention the biindolyl class material containing triaryl amine group.
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 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), there is smaller potential barrier, vapour deposition method to prepare organic electroluminescent with anode or hole-injecting material
When device, it is desirable that material energy vacuum evaporation forms pin-hole free films.Common HIM is aromatic multi-amine class compound, mainly
Derivative of tri-arylamine group.When preparing organic electroluminescence device for solwution method, it is desirable that material has suitable solubility, by solution
After being coated on substrate, after solution evaporation, fine and close, uniform unformed film can be formed on substrate.Common HIM material masters
There is PEDOT：PSS.
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 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 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, 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.When vapour deposition method prepares organic electroluminescence device, electron transfer layer generally uses Alq3
(8-hydroxyquinoline aluminium) either TAZ (3- phenyl -4- (1 '-naphthalene) -5- benzene -1,2,4- triazoles) or TPBi (tri- (N- of 1,3,5-
Phenyl -2- benzimidazoles) benzene) or it is derived from arbitrary two kinds of the collocation of these three materials.
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.
In the preparation process of organic electroluminescence device, all functional layers therein can be all made of vapor deposition legal system
It is standby, one layer therein or multilayer can also be prepared using vapour deposition method, other functional layers are prepared using solwution method, can also be incited somebody to action
All functional layers therein are all made of solwution method preparation.
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 as to the specific of the present invention
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.
The concrete structure of material therefor is seen below in embodiment：
PEDOT：PSS
Embodiment 3
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 is：ITO/HIL02(100nm)/HTL(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, HIL02 makees
Hole injection layer, EM1 make the material of main part of organic luminous layer, and TAZ makees electron injection as electron transport layer materials, LiF/Al
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
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in water, to improve the property on surface, improves and is passed with hole
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 hole transmission layer on hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 40nm.
Organic luminous layers 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 layers of the vacuum evaporation TAZ 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
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as hole transmission layer by upper table
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 4
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 is：ITO/HIL(100nm)/HTL(40nm)/EM1(30nm)/ETL(20nm)/
LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, NPB makees empty
Cave transport layer, EM1 make the material of main part of organic luminous layer, TAZ as electron transport layer materials, LiF/Al make 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
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in water, to improve the property on surface, improves and is passed with hole
The binding ability of defeated layer.
Above-mentioned glass substrate is placed in vacuum chamber, the vacuum evaporation hole injection layer on anode, 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 layers 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 layers of the vacuum evaporation TAZ 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
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as hole injection layer by upper table
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 5
Using the compound of the present invention as hole injection layer material, organic electroluminescence device is prepared by solwution method
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
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in water, to improve the property on surface, improves and is passed with hole
The binding ability of defeated layer.
The above-mentioned glass substrate through over cleaning is placed in glove box, under nitrogen atmosphere, by the solution of the compounds of this invention
(0.5% chlorobenzene solution) using spin coater with the uniform spin coating of the speed of 4000r/min on the glass substrate, then by glass
Vacuum drying removes solvent in 60 minutes at a temperature of glass substrate is placed in 150 degree, and what is prepared is coated with the glass of hole injection layer
Glass substrate.
The above-mentioned glass substrate for being coated with hole injection layer got ready is transferred to vacuum evaporation room, it is true on hole injection layer
Sky vapor deposition NPB is 40nm as hole transmission layer, evaporation rate 0.1nm/s, vapor deposition film thickness.
Organic luminous layers 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 layers of the vacuum evaporation TAZ 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 3：
Table 3
| Hole-injecting material | It is required that brightness cd/m2 | Driving voltage V | Current efficiency cd/A |
| Compound P-21 | 1000 | 6.45 | 1.39 |
| Compound P-22 | 1000 | 6.87 | 1.39 |
| Compound P-25 | 1000 | 7.8 | 1.44 |
| Compound P-26 | 1000 | 5.83 | 1.52 |
| Compound P-28 | 1000 | 5.51 | 1.57 |
| Compound P-29 | 1000 | 5.85 | 1.53 |
| Compound P-32 | 1000 | 5.84 | 1.57 |
| Compound P-36 | 1000 | 5.51 | 1.38 |
| Compound P-37 | 1000 | 7.75 | 1.37 |
| Compound P-38 | 1000 | 5.94 | 1.58 |
| Compound P-40 | 1000 | 7.41 | 1.39 |
| Compound P-41 | 1000 | 7.48 | 1.53 |
| Compound P-42 | 1000 | 7.77 | 1.54 |
| Compound P-43 | 1000 | 6.79 | 1.32 |
Comparative example
Utilize PEDOT：PSS prepares organic electroluminescence device as hole injection layer material, by solwution method.
Preparation method is with reference to embodiment 5, and only when preparing hole injection layer, preparation method is as follows：
Glass substrate through over cleaning is placed in glove box, under nitrogen atmosphere, by PEDOT：The aqueous solution of PSS uses rotation
Turn coating machine with the uniform spin coating of the speed of 4000r/min on the glass substrate, it is true at a temperature of glass substrate is then placed in 150 degree
Sky drying removes solvent in 60 minutes, and what is prepared is coated with the glass substrate of hole injection layer.
Utilize PEDOT：PSS prepares the performance of organic electroluminescence device by solwution method as hole injection layer material
It is shown in Table 4：
Table 4
| Hole-injecting material | It is required that brightness cd/m2 | Driving voltage V | Current efficiency cd/A |
| PEDOT：PSS | 1000 | 8.02 | 1.28 |
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 (3)
1. a kind of biindolyl class material containing triaryl amine group has structure shown in formula (1)：
Wherein Ar1, Ar2The independent aryl being made of carbon and hydrogen selected from C6~C40, B-1,
Ar3, Ar4, Ar5The independent aryl being made of carbon and hydrogen selected from C6~C40, * indicates benzene in B-1 and formula (1) in B-1
The position of the N atoms connection connected on ring；
Ar1, Ar2, Ar3, Ar4, Ar5Can be by the alkyl of C1~C20, the alkoxy of C1~C20, C6~C40 by carbon and hydrogen group
At aryl replaced；The substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted.
2. the biindolyl class material according to claim 1 containing triaryl amine group, the wherein aryl of C6~C40 are selected from：
Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, fluorenyl, fluoranthene base, indeno fluorenyl, Spirofluorene-based, benzo
Fluorenyl, dibenzo fluorenyl, phenyl substituted naphthyl, benzo anthryl；
The alkyl of C1~C20 is selected from methyl, ethyl, propyl, butyl, amyl, hexyl, cyclohexyl, heptyl, octyl；
The alkoxy of C1~C20 is selected from methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, cyclohexyloxy, heptan
Oxygroup, octyloxy.
3. the biindolyl class material according to claim 1 containing triaryl amine group, which is characterized in that the compound choosing
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010225950A (en) * | 2009-03-25 | 2010-10-07 | Toyo Ink Mfg Co Ltd | Organic electroluminescence element using polymer |
| KR20140006707A (en) * | 2012-07-05 | 2014-01-16 | (주)씨에스엘쏠라 | New organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20150109111A (en) * | 2014-03-19 | 2015-10-01 | 삼성전자주식회사 | Condensed compound and organic light emitting device including the same |
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2018
- 2018-05-17 CN CN201810476580.XA patent/CN108558731A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010225950A (en) * | 2009-03-25 | 2010-10-07 | Toyo Ink Mfg Co Ltd | Organic electroluminescence element using polymer |
| KR20140006707A (en) * | 2012-07-05 | 2014-01-16 | (주)씨에스엘쏠라 | New organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20150109111A (en) * | 2014-03-19 | 2015-10-01 | 삼성전자주식회사 | Condensed compound and organic light emitting device including the same |
Non-Patent Citations (3)
| Title |
|---|
| LUIS BERING ET AL.: "Aerobic, Metal-Free, and Catalytic Dehydrogenative Coupling of Heterocycles: En Route to Hedgehog Signaling Pathway Inhibitors", 《ORGANIC LETTERS》 * |
| SUGURU ITO ET AL.: "Two-Step Mechanochromic Luminescence of N,N’-Bis-Boc-3,3’-di(pyren-1-yl)-2,2’-biindole", 《CHEMPLUSCHEM》 * |
| 于军胜主编: "《显示器件技术》", 31 July 2010, 国防工业出版社 * |
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