CN105153135A - Photoelectric material containing furan structure and application thereof - Google Patents

Photoelectric material containing furan structure and application thereof Download PDF

Info

Publication number
CN105153135A
CN105153135A CN201510562632.1A CN201510562632A CN105153135A CN 105153135 A CN105153135 A CN 105153135A CN 201510562632 A CN201510562632 A CN 201510562632A CN 105153135 A CN105153135 A CN 105153135A
Authority
CN
China
Prior art keywords
layer
compound
photoelectric material
hole injection
organic electroluminescence
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.)
Granted
Application number
CN201510562632.1A
Other languages
Chinese (zh)
Other versions
CN105153135B (en
Inventor
付文岗
林存生
王子宁
高树坤
孟凡民
李祟
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.)
Valiant Co Ltd
Original Assignee
Valiant Co Ltd
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 Valiant Co Ltd filed Critical Valiant Co Ltd
Priority to CN201510562632.1A priority Critical patent/CN105153135B/en
Publication of CN105153135A publication Critical patent/CN105153135A/en
Application granted granted Critical
Publication of CN105153135B publication Critical patent/CN105153135B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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

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 invention relates to a photoelectric material containinga furan structure and application thereof. The structural formula of the photoelectric material is shown in the specification, wherein R1 and R2 are selected from any one of aromatic hydrocarbyl, aromatic hydrocarbon, aromatic heterocyclic, a substituted aryl group having no substituent with the carbon atom number of 6-36, aromatic heterocyclic radical, aryl containing a substituent radical or aryl without a substituent radical; the R1 and R2 are the same or not. The invention further provides application of the material in an organic electroluminescence device. An experiment result shows that the material has high thermal stability and glass transition temperature, and when the material is used as a hole injection material of an OLED (Organic Light Emitting Diode) device, the effects of high brightness, high efficiency and low voltage can be realized.

Description

A kind of photoelectric material and application thereof containing furan structure
Technical field
The present invention relates to a kind of photoelectric material and the application thereof that contain furan structure, belong to organic photoelectrical material field.
Background technology
The correlative study of organic electroluminescence device is initiated at the sixties in 19th century, until the end of the eighties, OLED was just flourish.OLED have all solid state, low-voltage driving, active illuminating, response fast, large, the emission wavelength of wide viewing angle, light-emitting area covers the advantages such as whole visible region and rich color, there is very large advantage realizing panchromatic large-area displays field, become the flat-panel display device having prospect.The luminosity of organic electroluminescence device is proportional to the product of the concentration of hole and electronics and the probability of recombination of exciton, go for higher luminous efficiency, not only need hole and electronics effectively to inject, transmit and compound and require that hole and electron injection reach balance.Therefore, in organic electroluminescence device, between organic layer and organic layer and two electrodes can be with mate device recombination luminescence extremely important.
In order to optimize the properties with balancing device, people introduce the functional layer of multiple not same-action, such as hole injection layer, hole blocking layer etc.The effect adding hole injection layer between ito anode and hole transmission layer is mainly manifested in reduction interface potential barrier, increases the Adhering capacity of hole transmission layer and ITO electrode, improves in its stability and balance electronic and hole injection etc.
Electron transport material and hole-injecting material or hole mobile material are the larger obstacles stopping that OLED versatility is practical, and it directly limit luminous efficiency and work-ing life and the operating voltage etc. of device.At present except triarylamine derivative or carbazole derivative, can be used as hole injection and be mainly six azepine triphenylene derivative, especially cyano group substituents (HaT-CN, WO01/049806).But its work-ing life, efficiency and operating voltage etc. also need to improve always.
Therefore, it is vital in organic electroluminescence device, finding efficient and long-life hole-injecting material.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide a kind of photoelectric material and the application thereof that contain furan structure, this photoelectric material can be raised the efficiency and the life-span, makes the driving life-span of device obtain larger lifting.The furans photoelectric material of the present invention's synthesis, has higher second-order transition temperature and molecular heat stability, easily forms good amorphous thin film, and easily, cost is lower, thus can well be applied in electroluminescent device technical field in preparation.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of photoelectric material containing furan structure, and its general structure is as follows:
Wherein, R 1and R 2all be selected from carbonatoms be 6 ~ 36 aromatic hydrocarbyl, aromatic heterocyclic radical, containing substituent aryl or containing any one in substituent aryl, R 1and R 2identical or different.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described R 1and R 2all be selected from one of following structural formula, R 1and R 2identical or different:
Wherein, the symbol * in above-mentioned each structural formula, represents the tie point with the parent be substituted.
Further, the described photoelectric material containing furan structure, is selected from one of following structural formula:
Due to a series of photoelectric material containing furan structure provided by the invention, with 1, centered by 4-difuryl phenyl group, introduce polyaromatic conjugated structure group for 3,5 at furans, experimental result shows, this material has high thermal stability and second-order transition temperature, as the hole-injecting material of OLED, uses such material to realize high brightness, high-level efficiency, the effect of low voltage.
Further, lower voltage is set in the course of the work and the high thermal stability itself had and second-order transition temperature, is applied in electroluminescent device, more stable effect and longer work-ing life can be obtained.
Because the preparation method of furan derivative provided by the invention is comparatively simple, therefore there is lower cost, more easily prepare in the industrial production and obtain, lower as material cost.
The present invention also provides a kind of application of the photoelectric material containing furan structure, in organic electroluminescence device, has a functional layer at least, containing the above-mentioned photoelectric material containing furan structure.
The present invention also provides a kind of organic electroluminescence device, comprise: the luminescent layer between anode layer and cathode layer, and the hole injection layer between described anode layer and described luminescent layer, wherein, the material of described hole injection layer is the above-mentioned photoelectric material containing furan structure.
Accompanying drawing explanation
Fig. 1 is the structural representation of organic electroluminescence device prepared by the present invention;
In accompanying drawing, the list of parts representated by each label is as follows:
1, transparent substrate layer, 2, anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, electron transfer layer, 7, electron injecting layer, 8, cathode layer.
Embodiment
Be described principle of the present invention and feature below, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Compound containing furan structure provided by the present invention, its synthetic route is as follows, R 1and R 2all be selected from carbonatoms be 6 ~ 36 aromatic hydrocarbyl, aromatic heterocyclic radical, containing substituent aryl or containing any one in substituent aryl, R 1and R 2identical or different.
As implied above, a kind of preparation method of the photoelectric material containing furan structure, with raw material 1 for starting raw material, after reacting with n-BuLi/Hex, after adding Isosorbide-5-Nitrae-hexichol formaldehyde reaction, then obtain target compound by acidic substance process (such as trifluoroacetic acid).
Above reaction raw materials material, catalyzer and provide the material of alkaline environment to be the art to commonly use material or easy commercially material.
Preparation embodiment
The part-structure of the concrete furans photoelectric material of the present invention's synthesis is as follows:
For ease of quoting hereafter, by numeric suffix under the structural formula of each compound above, and it is corresponding with compound in embodiment, such as, the compound (i.e. compound 1) of the corresponding embodiment 1 of structural formula 1, the compound (i.e. compound 2) of the corresponding embodiment 2 of structural formula 2, remaining by that analogy.In addition, after the molecular formula in each embodiment, also there is corresponding mark.
The synthesis of embodiment 1 compound 1:
19.90g (40mmol) 7-phenyl-5-((2-phenyl-1 is added in there-necked flask; 3-dimercapto-2-base) ethynyl) THF of-7H-benzo [c] carbazole and 200mL drying; under nitrogen protection; slow cooling is to-78 DEG C; drip 16mL (2.5mol/L) butyllithium hexane solution; within 1.0 hours, drip and finish, insulation reaction 3.0hrs.In controlling, temperature is less than-78 DEG C, drips the 100mLTHF solution of 2.68g (20mmol) Isosorbide-5-Nitrae-terephthal aldehyde, within 30 minutes, drips and finishes.Drip after finishing, system-78 DEG C of insulated and stirred 1.0 hours, are then slowly warming up to 20 ~ 25 DEG C, stirring reaction 2 hours.And backward reaction solution adds 3mL (39mmol) trifluoroacetic acid, then reaction solution 20 ~ 25 DEG C stirs 10.0 hours, adds saturated aqueous ammonium chloride cancellation reaction.Successively with the sodium bicarbonate aqueous solution of massfraction 10%, saturated aqueous common salt and deionized water wash.Anhydrous sodium sulfate drying, decompression desolventizing is extremely without cut, and gained crude product, by Gossypol recrystallized from chloroform, obtains 10.9g compound 1, yield 27.7%.DEI-MS is used to identify this compound, molecular formula C 70h 44n 2o 2, detected value [M+1] +=946.49, calculated value 945.11.
The synthesis of embodiment 2 compound 2
With 2-phenyl-2-((4-phenylnaphthalene-1-base) ethynyl)-1,3-dimercapto replaces 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepare by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 58h 38o 2, detected value [M+1] +=767.56, calculated value 766.92.
The synthesis of embodiment 3 compound 3
With 2-([1,1'-xenyl]-4-base-ethynyl)-2-phenyl-1,3-dimercapto replaces 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepares by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 50h 34o 2, detected value [M+1] +=667.93, calculated value 666.80.
The synthesis of embodiment 4 compound 4
With 2-((7,7-dimethyl-7H-benzo [c] fluorenes-5-base) ethynyl)-2-phenyl-1,3-dimercapto replaces 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepare by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 64h 46o 2, detected value [M+1] +=847.69, calculated value 847.05.
The synthesis of embodiment 5 compound 5
With 7-phenyl-5-(2-(phenylene-ethynylene)-1,3-dimercapto-2-base)-7H-benzo [c] carbazole replacement 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepare by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 70h 44n 2o 2, detected value [M+1] +=946.41, calculated value 945.11.
The synthesis of embodiment 6 compound 6
With 2-(7,7-dimethyl-7H-benzo [c] fluorenes-5-base)-2-(phenylene-ethynylene)-1,3-dimercapto replaces 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepare by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 64h 46o 2detected value [M+1] +=847.82, calculated value 847.05.
The synthesis of embodiment 7 compound 7
With 2-([1,1'-xenyl]-4-base)-2-(this ethyl-acetylene base)-1,3-dimercapto replaces 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepare by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 50h 34o 2detected value [M+1] +=667.31, calculated value 666.80.
The synthesis of embodiment 8 compound 8
With 2-(phenylene-ethynylene)-2-(4-phenylnaphthalene-1-base)-1,3-dimercapto replaces 7-phenyl-5-((2-phenyl-1,3-dimercapto-2-base) ethynyl)-7H-benzo [c] carbazole, prepare by the synthetic method of compound 1 in embodiment 1.DEI-MS is used to identify this compound, molecular formula C 58h 38o 2detected value [M+1] +=767.84, calculated value 766.92.
Embodiment prepared by device
Describe below in conjunction with Fig. 1.Organic electroluminescence device comprises transparent substrate layer 1, anode layer 2, hole injection layer 3, hole transmission layer 4, luminescent layer 5, electron transfer layer 6, electron injecting layer 7 and cathode layer 8, and each Rotating fields presses the order arrangement of transparent substrate layer 1, anode layer 2, hole injection layer 3, hole transmission layer 4, luminescent layer 5, electron transfer layer 6, electron injecting layer 7 and cathode layer 8 from bottom to up.
Making such electro-luminescence display device can use all known or be expected to the material that develops future as the material forming each layer, and material is made film to be formed by methods such as vapour deposition method, spin-coating method or teeming practices by each layer.The thickness of each layer formed in this way is not particularly limited, and may correspond to the character of material and is suitable for setting, being generally 2nm ~ 5000nm.Moreover, the method for luminescent material thin-film is easily obtained uniform rete and not easily generates the experience of pin hole, preferred vapour deposition method.Evaporation condition is generally preferred at boat, Heating temperature 50 DEG C ~ 400 DEG C, vacuum tightness 10 -6pa ~ 10 -3pa, evaporation rate 0.01nm/s ~ 50nm/s, substrate temperature-150 DEG C ~ 300 DEG C, thickness 5nm ~ 5um.
Anode layer 2 has function hole being injected into hole transmission layer 4, and anode layer 2 is made up of following material usually: as metals such as aluminium, gold and silver, nickel, palladium or platinum; As metal oxides such as Indium sesquioxide, stannic oxide, zinc oxide, indium tin composite oxides, indium zinc composite oxides; As metal halides such as cupric iodides; Carbon black; Or partially conductive polymer etc.
Hole injection layer 3 can be used for promoting that holes from anode is injected into luminescent layer 5, and according to device architecture of the present invention, hole injection layer 3 can use material provided by the invention to be formed.
Hole transmission layer 3 is high-level efficiency from anode layer 2 injected hole and effectively can transmits the material of injected holes.Therefore, needing that the ionizing potential of this material is low, high to the perviousness of visible ray, hole mobility is high, stable in properties, also needing the light not easily produced when preparing or use to become the impurity of trap (trap).In addition owing to contacting with luminescent layer 5, hole transmission layer 4 is needed not make the light delustring of light emitting layer 5, and not and form exciplex between luminescent layer 5 and the common hole mobile material that lowers efficiency can enumerate with, N, N '-phenylbenzene-N, N '-(1-naphthyl)-1, the aromatic diamine containing plural tertiary amine that 1 '-biphenyl-4,4 '-diamines (NPB) is representative, triphen amine have the aromatic amine compounds, carbazoles derivative etc. of star radial configuration.
Luminescent layer 5 is formed by luminophore, wherein, between the electrode being applied with electric field, this luminophore because of hole and electronics combination again and excite, thus show strong luminescence.Usual luminescent layer 5 is containing as the doping type material of luminophore and substrate material.In order to obtain high-level efficiency electroluminescent device, the adoptable a kind of dopant material of its luminescent layer 5, or adopt multiple dopant material.Dopant material can be simple fluorescence or phosphor material, or is formed by different fluorescence and phosphorescence matched combined, and luminescent layer 5 can be single emitting layer material, also can for the recombination luminescence layer material be superimposed.
The material of main part of luminescent layer 5 not only needs to possess ambipolar transferring charge character, need appropriate energy rank simultaneously, excitation energy is delivered to guest emitting material effectively, and the material of this class can enumerate diphenylethyllene aryl derivatives, stibene derivative, carbazole derivative, triarylamine derivatives, anthracene derivant, pyrene derivatives, coronene derivative etc.
Relative to material of main part, the weight of mixing of guest materials is preferably 0.01%-20%.The material of this class can enumerate the metal complexes of iridium, nail, platinum, rhenium, palladium etc.
Form the material of the electron transfer layer 6 of above-mentioned electroluminescent device, can select to use arbitrarily by the electroluminescent material possessing electronic transport property, such material can be enumerated as 1,3, the benzimidazoles derivatives such as 5-tri-(1-naphthyl-1H-benzimidazolyl-2 radicals-Ji) benzene (TPBI), three (oxine) aluminium (Alq 3) etc. metal complexes, 2-(4 ,-trimethylphenylmethane base)-5-(4 ,-xenyl)-1,3,4-oxadiazoles (oxadiazole derivative such as PBD) Deng, the phenanthroline derivatives such as 4,7-phenylbenzene-1,10-phenanthroline (BPhen), triazole derivative, quinoline, quinoxaline derivatives etc.
The optional work function of above-mentioned electroluminescent device spendable cathode layer 8 material is less than the metal of 4eV, alloy, conductive compound and their mixture.Its concrete example is aluminium, calcium, magnesium, lithium, magnesium alloy, aluminium alloy etc.In order to obtain electroluminescence efficiently, comparatively ideal is that the transmitance of at least one of electrode is set to more than 10%.Cathode layer 8 by dry method as vacuum evaporation, vapour deposition or sputtering formed.
Device embodiments and device comparative example
Below, describing compound provided by the present invention in detail by device embodiments 1-8 and comparative example 1 and 2 is material, prepares organic electroluminescence device provided by the invention and effect thereof.Wherein, device embodiments 1-8 using compound provided by the invention as the material of hole injection layer, and proves its beneficial effect with comparative example 1 and 2.
In addition, due to the method provided according to device embodiments 1, select compound provided by the invention to be the material of hole injection layer, can prepare, so summary.
Device embodiments 1
In conjunction with preparation method and the Figure of description of device, and compound provided by the invention is selected to be used as hole injection layer 3, its application and result in organic electroluminescence device hole injection layer 3 outstanding.
A) anode layer 2 on transparent substrate layer 1 is cleaned: clean each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, then in plasma cleaner, process 2 minutes;
B) evaporation hole injection layer 3 on anode layer 2, compound 1 prepared by the embodiment of the present invention 1 is as the material of hole injection layer 3, and thickness is 30nm;
C) on hole injection layer 3, by vacuum evaporation mode evaporation TCTA, its thickness is 10nm, and this layer of organic materials uses as hole transmission layer 4.
D) on hole transmission layer 4 co-evaporation luminescent layer 5, CBP as material of main part, Ir (ppy) 3as phosphorescence dopant material, phosphor material doping ratio is 5% (phosphor material: material of main part=5wt%:95wt%), and thickness is 30nm;
E) on doping type luminescent layer compound, by vacuum evaporation mode evaporating Al q 3, thickness is 30nm, and this layer of organic materials uses as electron transfer layer 6;
F) on electron transfer layer 6, vacuum evaporation electron injecting layer LiF, thickness is 0.5nm, and this layer is electron injecting layer 7;
G) on electron injecting layer 7, vacuum evaporation negative electrode Al layer, thickness is 100nm, and this layer is cathode layer 8.
After completing electroluminescent device as above-mentioned, the driving voltage of measuring element, quantum yield, current efficiency, power efficiency and brightness, its result in Table 1.
Device embodiments 2
The difference of the present embodiment and device embodiments 1 is: the compound 2 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 2 is for material.The result of the organic electroluminescence device made by device embodiments 2 in Table 1.
Device embodiments 3
The difference of the present embodiment and device embodiments 1 is: the compound 3 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 3 is for material.The result of the organic electroluminescence device made by device embodiments 3 in Table 1.
Device embodiments 4
The difference of the present embodiment and device embodiments 1 is: the compound 4 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 4 is for material.The result of the organic electroluminescence device made by device embodiments 4 in Table 1.
Device embodiments 5
The difference of the present embodiment device and device embodiments 1 is: the compound 5 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 5 is for material.The result of the organic electroluminescence device made by device embodiments 5 in Table 1.
Device embodiments 6
The difference of the present embodiment device and device embodiments 1 is: the compound 6 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 6 is for material.The result of the organic electroluminescence device made by device embodiments 6 in Table 1.
Device embodiments 7
The difference of the present embodiment device and device embodiments 1 is: the compound 7 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 7 is for material.The result of the organic electroluminescence device made by device embodiments 7 in Table 1.
Device embodiments 8
The difference of the present embodiment and device embodiments 1 is: the compound 8 that the hole injection layer of the organic electroluminescence device of preparation is prepared with the embodiment of the present invention 8 is for material.The result of the electroluminescent device made by device embodiments 8 in Table 1.
Device comparative example 1
Device comparative example 1 and device embodiments 1 unlike: the hole injection layer of organic electroluminescence device is using HAT-CN as hole-injecting material.
Device comparative example 2
Device comparative example 2 and device embodiments 1 unlike: the organic electroluminescence device of preparation, does not form hole injection layer.
The result of the electroluminescent device made by device comparative example 1 and 2 in Table 1.
Table 1
Seen by table 1, photoelectric material of the present invention can be applicable to electroluminescent device and makes, and can obtain good performance.Device comparative example 1 uses existing conventional Hat-CN as hole-injecting material, and its driving voltage is significantly better than the device comparative example 2 without hole injection layer, and its driving voltage about reduces 16%; Material of the present invention uses as the hole-injecting material of electroluminescent device simultaneously, and its driving voltage is much better than device comparative example 1 and 2, and compared to device comparative example 2, the driving voltage of device embodiments 1 to 8 reduces 31%-38%;
In addition, compare with 2 with device comparative example 1, the quantum yield of device embodiments 1 to 8, current efficiency, power efficiency and brightness all obtain obvious improvement.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.

Claims (5)

1. the photoelectric material containing furan structure, it is characterized in that, its general structure is as follows:
Wherein, R 1and R 2all be selected from carbonatoms be 6 ~ 36 aromatic hydrocarbyl, aromatic heterocyclic radical, containing substituent aryl or containing any one in substituent aryl, R 1and R 2identical or different.
2. photoelectric material according to claim 1, is characterized in that, described R 1and R 2all be selected from one of following structural formula, R 1and R 2identical or different:
3. photoelectric material according to claim 2, is characterized in that, described photoelectric material is selected from one of following structural formula:
4. an application for the photoelectric material containing furan structure, is characterized in that, in organic electroluminescence device, having a functional layer at least, containing the arbitrary described photoelectric material containing furan structure of claim 1-3.
5. an organic electroluminescence device, it is characterized in that, comprise: the luminescent layer between anode layer and cathode layer, and the hole injection layer between described anode layer and described luminescent layer, wherein, the material of described hole injection layer is the arbitrary described photoelectric material containing furan structure of claim 1-3.
CN201510562632.1A 2015-09-07 2015-09-07 A kind of photoelectric material containing furan structure and its application Active CN105153135B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510562632.1A CN105153135B (en) 2015-09-07 2015-09-07 A kind of photoelectric material containing furan structure and its application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510562632.1A CN105153135B (en) 2015-09-07 2015-09-07 A kind of photoelectric material containing furan structure and its application

Publications (2)

Publication Number Publication Date
CN105153135A true CN105153135A (en) 2015-12-16
CN105153135B CN105153135B (en) 2017-12-29

Family

ID=54794226

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510562632.1A Active CN105153135B (en) 2015-09-07 2015-09-07 A kind of photoelectric material containing furan structure and its application

Country Status (1)

Country Link
CN (1) CN105153135B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112979623A (en) * 2021-02-22 2021-06-18 吉林奥来德光电材料股份有限公司 Five-membered heterocyclic compound, preparation method thereof, organic electroluminescent device and element

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101508687A (en) * 2009-03-30 2009-08-19 中国广州分析测试中心 Polysubstituted furfuran compound and uses of the same as effective luminous element in LED aspect

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101508687A (en) * 2009-03-30 2009-08-19 中国广州分析测试中心 Polysubstituted furfuran compound and uses of the same as effective luminous element in LED aspect

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WENBIN FAN ET AL.: "Dinaphtho-s-indacene-based copolymers for inverted organic solar cells with high open-circuit voltages", 《POLYMER》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112979623A (en) * 2021-02-22 2021-06-18 吉林奥来德光电材料股份有限公司 Five-membered heterocyclic compound, preparation method thereof, organic electroluminescent device and element

Also Published As

Publication number Publication date
CN105153135B (en) 2017-12-29

Similar Documents

Publication Publication Date Title
Zheng et al. Highly efficient non-doped deep-blue organic light-emitting diodes based on anthracene derivatives
Chen et al. Synthesis and characterization of n‐type materials for non‐doped organic red‐light‐emitting diodes
Yoo et al. A new electron transporting material for effective hole-blocking and improved charge balance in highly efficient phosphorescent organic light emitting diodes
CN103694277A (en) Red-phosphorescence organic light emitting diode (LED)
CN102031104B (en) Bipolar phosphorescent main material containing anthracene derivatives of tetraphenyl silicane and carbazole and organic electroluminescent device
CN110078754A (en) Compound, display panel and display device
CN102775398A (en) Novel bipolar material and application thereof
CN104513662A (en) Organic light-emitting material and application thereof
KR101415734B1 (en) Hole transporting material using new arylamine and organic electroluminescent device comprising the same
CN104449671A (en) Organic neutral radical electroluminescence material and organic electroluminescence device prepared by using material
KR101794796B1 (en) Electron transporting material and Organic electroluminescent display device using the same
Bao et al. New carbazole-based bipolar hosts for efficient green phosphorescent organic light-emitting diodes
CN104649956A (en) Fluoro-carbazole derivative and application thereof in organic light-emitting device
CN111233840A (en) Quinoxaline derivative and application thereof in organic light-emitting device
CN106898709A (en) A kind of red phosphorescent organic electroluminescence device
US8941099B2 (en) Organic light emitting device and materials for use in same
CN105348300A (en) Organic photoelectric material and applications thereof
CN105176519A (en) OLED optoelectronic material and applications thereof
CN114437032B (en) Compound containing tetrabiphenyl and application thereof
CN105237520A (en) Compound material containing pyrazoline structure and application of compound material
CN105837570B (en) A kind of electron transport material and its preparation method and application
CN105153135B (en) A kind of photoelectric material containing furan structure and its application
CN109438469B (en) Organic photoelectric material containing thiophene structure and application thereof
KR102128299B1 (en) Novel organic electroluminescent compound, organic electroluminescent device including the same and electric apparatus
Zhao et al. The facile synthesis and high efficiency of the red electroluminescent dopant DCINB: A promising alternative to DCJTB

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
PE01 Entry into force of the registration of the contract for pledge of patent right

Denomination of invention: A photoelectric material containing furan structure and its application

Effective date of registration: 20211202

Granted publication date: 20171229

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PE01 Entry into force of the registration of the contract for pledge of patent right
PC01 Cancellation of the registration of the contract for pledge of patent right

Date of cancellation: 20220823

Granted publication date: 20171229

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PC01 Cancellation of the registration of the contract for pledge of patent right