CN108752262A - A kind of biindolyl class electroluminescent organic material - Google Patents

A kind of biindolyl class electroluminescent organic material Download PDF

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CN108752262A
CN108752262A CN201810766425.1A CN201810766425A CN108752262A CN 108752262 A CN108752262 A CN 108752262A CN 201810766425 A CN201810766425 A CN 201810766425A CN 108752262 A CN108752262 A CN 108752262A
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organic electroluminescence
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赵东敏
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Abstract

The present invention relates to display technology fields, more particularly to a kind of biindolyl class material, organic electroluminescence device and display device.Shown in compound according to the present invention such as formula (1)：

Description

A kind of biindolyl class electroluminescent organic material
Technical field
The present invention relates to display technology fields, more particularly to a kind of biindolyl class electroluminescent organic material, Organic Electricity Electroluminescence device 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
Have the present invention provides a kind of biindolyl class material, the organic electroluminescence device comprising the compound and with this The display device of organic electroluminescence devices, including the organic electroluminescence device of the compound have lower driving voltage and compared with High luminous efficiency.
According to an aspect of the present invention, a kind of biindolyl class material is provided, as shown in formula (1)：
Wherein A is selected from the aryl of singly-bound, C6~C40 being made of carbon and hydrogen；B is selected from carbazyl, benzo carbazole base, hexichol And carbazyl, indeno carbazyl, indolocarbazole base, indoles and Spirofluorene-based, acridan base, dihydrophenazine base, 10H- pheno thiophenes Piperazine base, 10H- phenoxazine bases；A, B can be by the alkyl of C1~C20, the alkoxy of C1~C20, C6~C40 by carbon and hydrogen group At aryl, B-1 replaced；The substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted：
Ar1, Ar2The independent aryl being made of carbon and hydrogen selected from C6~C40, * indicates that B connects in B-1 and formula (1) in B-1 The position connect；Ar1, Ar2It can be by the alkyl of C1~C20, the alkoxy of C1~C20, the virtue of C6~C40 being made of carbon and hydrogen Base is replaced；The substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted.
Further, the wherein aryl of C6~C40 is selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, three Phenylene, 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 alcoxyl of C1~C20 Base is selected from methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, cyclohexyloxy, oxygroup in heptan, octyloxy.
Further, biindolyl class material provided by the invention, selected from lower structure：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Including biindolyl class material according to the present invention.
Optionally, the hole mobile material of the organic electroluminescence device is the biindolyl class material according to the present invention.
Optionally, the hole-injecting material of the organic electroluminescence device is the biindolyl class material according to the present invention.
Optionally, the material of main part of the luminescent layer of the organic electroluminescence device is the biindolyl class material according to the present invention Material.
Further, the luminescent layer of the organic electroluminescence device is phosphorescence luminescent 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.
Beneficial effects of the present invention are as follows：
By hole-injecting material of the compound provided by the invention as organic electroluminescence device or/and hole transport Material or luminescent layer material of main part improve the luminous efficiency of organic electroluminescence device, reduce organic electroluminescent The driving voltage of device.
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.
Have the present invention provides a kind of biindolyl class material, the organic electroluminescence device comprising the compound and with this The display device of organic electroluminescence devices, including the organic electroluminescence device of the compound have lower driving voltage and compared with High 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, 300 milliliters of dry toluene, 19.2 grams of (0.05mol) 3 are added, 3'- diphenyl -1H, 1'H-2,2'- biindolyl, 38.6 grams of (0.12mol) N- (4- bromophenyls) carbazoles, 14.4 grams (0.15mol) The tri-tert-butylphosphine of sodium tert-butoxide, 0.58 gram (0.001mol) bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% Toluene solution, be down to room temperature after being heated to back flow reaction 8 hours, dilute hydrochloric acid, liquid separation, during organic layer is washed with water be added Property, after being dried with anhydrous magnesium sulfate, cross silica gel post separation, ethyl acetate：Petroleum ether=1：5 (volume ratios) elute, and eluent is dense Be reduced to it is dry, with methanol/toluene mixed solvent recrystallize, obtain 29.1 grams of compound shown in formula P-1, yield 67.1%.
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e of product：866.
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 8.56 (m, 2H), δ 8.19 (m, 4H), δ 7.90 (s, 8H), δ 7.52 (m, 6H), δ 7.48 (t, 4H), δ 7.43 (m, 4H), δ 7.35 (m, 2H), δ 7.29 (m, 2H), δ 7.22~7.13 (m, 8H), δ 7.11 (m, 2H).
The synthesis of 2 other parts compound of embodiment
The synthetic method of reference compound P-1 only changes N- therein (4- bromophenyls) carbazole accordingly into as needed Bromo compound, other of the invention compounds can be synthesized.
The specific reaction bromo compound used in part and obtained the compound of the present invention mass spectrometric data is set forth below：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Hole-injecting material/hole mobile material/luminescent layer material of main part be according to the present invention biindolyl class material.
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.
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：
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
The compound of the present invention is as the material of main part in red phosphorescent OLED organic electroluminescence devices：
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)。
One of them is comparison organic electroluminescence device, and feux rouges material of main part selects CBP, other 7 organic electroluminescences hairs Optical device selects the material of the present invention.
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 Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to, Vacuum evaporation hole transmission layer NPB on above-mentioned 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；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as cathode.
Organic electroluminescence device performance is shown in Table 3：
Table 3
By upper table it can be seen that, 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 6：
The compound of the present invention is as the material of main part in green phosphorescent OLED organic electroluminescence devices：
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)。
One of them is comparison organic electroluminescence device, and green light material of main part selects CBP, other 8 organic electroluminescences hairs Optical device selects the material of the present invention.
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 Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to, Vacuum evaporation hole transmission layer NPB on above-mentioned 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；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
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 4：
Table 4
By upper table it can be seen that, 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.
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 has structure shown in formula (1)：
Wherein A is selected from the aryl of singly-bound, C6~C40 being made of carbon and hydrogen；
B be selected from carbazyl, benzo carbazole base, dibenzo-carbazole base, indeno carbazyl, indolocarbazole base, indoles and it is Spirofluorene-based, Acridan base, dihydrophenazine base, 10H- phenothiazinyls, 10H- phenoxazine bases；
A, B can be by the alkyl of C1~C20, the alkoxy of C1~C20, the aryl of C6~C40 being made of carbon and hydrogen, B-1 institutes Substitution；The substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted：
Ar1, Ar2The independent aryl being made of carbon and hydrogen selected from C6~C40, * indicates what B-1 was connected with B in formula (1) in B-1 Position；
Ar1, Ar2It can be taken by the alkyl of C1~C20, the aryl of the alkoxy of C1~C20, C6~C40 being made of carbon and hydrogen Generation；The substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted.
2. biindolyl class material according to claim 1, the wherein aryl of C6~C40 are selected from：Phenyl, xenyl, three Phenyl, 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 be 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. biindolyl class material according to claim 1, which is characterized in that the compound is selected from：
CN201810766425.1A 2018-07-12 2018-07-12 A kind of biindolyl class electroluminescent organic material Withdrawn CN108752262A (en)

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Application publication date: 20181106