CN110407834A - A kind of OLED material of main part and the preparation method and application thereof - Google Patents
A kind of OLED material of main part and the preparation method and application thereof Download PDFInfo
- Publication number
- CN110407834A CN110407834A CN201910682856.4A CN201910682856A CN110407834A CN 110407834 A CN110407834 A CN 110407834A CN 201910682856 A CN201910682856 A CN 201910682856A CN 110407834 A CN110407834 A CN 110407834A
- Authority
- CN
- China
- Prior art keywords
- main part
- oled
- oled material
- compound
- organic
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The present invention relates to a kind of OLED material of main parts, have the structure as shown in general formula I.Novel OLED material provided by the invention is centered on dibenzofurans, since dibenzofurans is a preferable electron-transport unit, therefore the material has hole transporting property and electronic transport property simultaneously, the tangible transmission balance for transmitting hole and electronics in luminescent layer;Triplet also with higher effectively prevents energy in luminescence process from returning to material of main part, to improve its luminous efficiency.
Description
Technical field
The present invention relates to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical fields, and in particular to a kind of new organic materials and its organic
Application in electroluminescent device.
Background technique
Application of organic electroluminescent (OLED) material in the fields such as information display material, organic optoelectronic material has
Great researching value and fine application prospect.With the development of multimedia information technology, to flat-panel display device performance
It is required that higher and higher.Current main display technology has plasma display apparatus, field emission display and organic electroluminescent
Display device (OLED).Wherein, OLED has itself luminous, low-voltage direct-current driving, all solidstate, the wide, various colors in visual angle etc.
Series of advantages, compared with liquid crystal display device, OLED does not need backlight, and visual angle is wider, low in energy consumption, and response speed is liquid
1000 times of crystal display device, therefore, OLED have broader practice prospect.
Efficient commercialization Organic Light Emitting Diode applies the phosphor containing organic metal complex of iridium, because they can
To capture singlet and triplet excitons, to realize 100% internal quantum efficiency.However, due to Transition metal complexes
The excitation state exciton lifetime of object is relatively too long, and is easy to happen the concentration quenching effect of luminescent material, leads to unnecessary three
Line state-triplet state (T1-T1) is quenched in device real work, and in order to overcome this problem, researchers often send out triplet state
Light object is doped in organic host material.In recent years, efficient phosphorescent devices are seldom, and main cause is a lack of while having preferably
Carrier transmission performance and higher triplet material of main part.
Summary of the invention
The purpose of the present invention is to provide the OLED compounds that can carry out low voltage drive, long-life, and have used this
The OLED element of class compound and high efficiency.
In order to develop the compound with aforesaid properties and use the OLED element of such compound, as a result, it has been found that, lead to
The compound indicated using general formula I is crossed, can reach above-mentioned purpose.
That is, there is the structure as shown in general formula I the invention proposes a kind of OLED material of main part:
In dibenzofurans main structure shown in general formula I, any one phenyl ring is simultaneously by 1 aromatic group Ar and m F
Atom replaces, and the m can be selected from 1,2 or 3.
As a preferred solution of the present invention, structure shown in general formula I is as follows:
Wherein, m represents the substitution number of F atom on phenyl ring, can be selected from 1,2 or 3.
Specifically, 1,2 or 3 F atom may replace Formulas I ' shown in structure 1,2 or No. 3 position on hydrogen atom.
As m=1, F atom may replace Formulas I ' shown in hydrogen atom on 1,2, the 3 of structure any one position, i.e., it is described
Structure shown in optional ' -1 of the Formulas I freely~I ' -3 of organic material, the structure shown in ' -2 preferably such as Formulas I.
As m=2, F atom may replace Formulas I ' shown in structure 1,2, No. 3 any two position on hydrogen atom, i.e. institute
State structure shown in optional ' -4 of the Formulas I freely~I ' -6 of organic material.
As m=3, F atom may replace Formulas I ' shown in 1,2 and No. 3 of the structure hydrogen atom on totally three positions, i.e., it is described
Structure shown in optional ' -7 of Formulas I freely of organic material:
Ar represents the aromatic group containing n phenyl ring and/or heteroaromatic in the general formula I.The aromatic group can be
Substituted or unsubstituted mononuclear aromatics is also possible to substituted or unsubstituted polycyclic aromatic hydrocarbon;The polycyclic aromatic hydrocarbon can be more benzene
For rouge hydrocarbon, biphenyl type polycyclic aromatic hydrocarbon or condensed-nuclei aromatics.The n represents 1,2,3,4 or 5, preferably 3,4 or 5.It can be in the Ar
Containing S atom and/or N atom, 1~3 N atom is preferably comprised.
The present invention carries out preferably, to further increase the comprehensive performance of material the group that Ar is represented.Specifically, Ar can
Selected from following group:
Preferably, Ar can be selected from following group:
It is further preferred that Ar can be selected from following group:
In above-mentioned each substituent group,It indicates to replace position.
Organic material shown in the further preferred general formula I of the present invention is selected from following general formula I-1~I-8 compound represented:
In the general formula I-1~I-8, m is independently represented each other 1,2 or 3, the specific substitution mode of F atom institute for example above
It states.
Since dibenzofurans is a preferable electron-transport unit, material provided by the invention has sky simultaneously
Cave transport property and electronic transport property realize the transmission balance of hole and electronics in transmission luminescent layer, also with higher
Triplet effectively prevents energy in luminescence process from returning to material of main part, to improve its luminous efficiency.It is taken with fluorine
It can change packing of molecules for the atom on phenyl ring, significantly reduce self-quenching when higher-doped concentration, improve luminous efficiency.Draw
The volatility of compound can also be improved by entering C-F key, make it easy to the preparation of device.HOMO-LUMO energy gap can also pass through fluorine
Change to change, to optimize the injection of carrier, adjusts the operating voltage and efficiency of electroluminescent device.
Invention also provides the preparation methods of material shown in general formula I.
The reaction mechanism mechanism of reaction of the preparation method is as follows:
Include the following steps:
Using compound A as starting material, withCoupling reaction occurs, obtains compound I;Wherein, m is 1 to 3
Integer.
Known common approach can be used to realize in above-mentioned step those skilled in the art, such as selects suitable catalysis
Agent, solvent determine suitable reaction temperature, and time etc., the present invention is not particularly limited this.
As a preferred solution of the present invention, above-mentioned preparation method includes the following steps:
Using compound A as starting material, using toluene as solvent, using Pd132 as catalyst, sodium carbonate is alkali, nitrogen protection,
70-100 DEG C of temperature control, compound A withCoupling reaction occurs, obtains compound I.
The raw materials such as above-mentioned solvent, catalyst, alkali can be closed by public commercial source or methods known in the art
At obtaining.
Invention further provides application of the OLED material of main part in organic electroluminescence device shown in general formula I.
The preferably described OLED material of main part of the present invention is used as the light emitting host material of luminescent layer in organic electroluminescence device.
It include shown in general formula I of the present invention the present invention also provides a kind of organic electroluminescence device, in organic function layer
OLED material of main part.The preferably described OLED material of main part of the present invention is used as the light emitting host of organic luminous layer in organic function layer
Material.The thickness of the organic luminous layer can be 10~100nm, preferably 40~80nm.
As a preferred solution of the present invention, above-mentioned organic electroluminescence device successively includes transparent base from the bottom to top
Piece, anode layer, hole transmission layer, using compound shown in general formula I as the organic luminous layer of material of main part, electron transfer layer, electricity
Sub- implanted layer and cathode layer.
Wherein, glass substrate or flexible substrate can be selected in the material for constituting the transparent substrate, and tradition specifically can be used
Substrate in organic luminescent device, such as glass substrate or plastic base, preferably use glass substrate.
Inorganic material can be selected in the material for constituting the anode layer, and tin indium oxide (ITO), zinc oxide, oxygen specifically can be selected
Change at least one of tin zinc, gold, silver or copper, preferably tin indium oxide (ITO).
The material for constituting the hole transmission layer is made of cavitation material, and the cavitation material can be selected in following compound
Any one:
The material of main part for constituting the organic luminous layer is general formula I compound represented of the present invention.The organic luminous layer
In also contain luminescent material, can be selected Ir (PiQ)3, structure is as follows:
The material for constituting the electron transfer layer can be selected from any one in following compound:
The material for constituting the electron injecting layer can be selected from LiF, Li2O、MgO、Al2O3One of, preferably LiF.
The material choosing for constituting the cathode can be from one of lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin, preferably
Aluminium.
In order to ensure playing synergistic effect in the luminescent device between the material of each layer, the present invention is also to the photophore
The thickness of each layer carries out preferably in part, so that the luminescent device plays optimal resultant effect.
Specifically, the thickness of the hole transmission layer can be 10~50nm, preferably 27~33nm;Organic hair
The thickness of photosphere can be 10~100nm, preferably 40~80nm;The thickness of the electron transfer layer can be 10~30nm,
Preferably 18~22nm;The thickness of the electron injecting layer can be 5~30nm, preferably 9~11nm;The thickness of the cathode layer
Degree can be 50~200nm, preferably 100~200nm.
Novel OLED material provided by the invention is centered on dibenzofurans, since dibenzofurans is one preferable
Electron-transport unit, therefore the material has hole transporting property and electronic transport property simultaneously, tangible transmission luminescent layer is hollow
The transmission of cave and electronics balances;Triplet also with higher effectively prevents energy in luminescence process from returning to main body
Material, to improve its luminous efficiency.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
Embodiment 1
The synthesis of compound I-7-2
Synthetic route is as follows:
Specific synthesis step are as follows:
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium carbonate 19.93g (0.188mol), (4- after nitrogen displacement
(diphenylamino) phenyl) boric acid 28.91g (purity 99%, 0.1mol) and toluene 100ml.It is sequentially added after nitrogen displacement again
0.23g Pd132.After adding, it is heated to 80 DEG C.Start to be added dropwise (pure by 39.76g bromo- 2- fluorine dibenzofurans containing 4-
Spend 99%, 0.15mol) and 100ml toluene form solution, 75-80 DEG C of temperature control.It is cooled to room temperature, 100m deionized water is added
Hydrolysis is stirred 10 minutes, and filtering, filter cake is boiled several times repeatedly with DMF, obtains 38.65g white product, purity 99%, yield
80%.
Product MS (m/e): 429.48;Elemental analysis (C30H20FNO): theoretical value C:83.80%, H:4.69%, F:
4.43%, N:3.26%, O:3.72%;Measured value C:83.89%, H:4.70%, F:4.43%, N:3.26%, O:3.72%.
Embodiment 2
The synthesis of compound I-6-2
Synthetic route is as follows:
Specific synthesis step are as follows:
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium carbonate 19.93g (0.188mol), (4- after nitrogen displacement
(4,6- diphenyl -1,3,5-triazines -2- base) phenyl) boric acid 35.3g (purity 99%, 0.1mol) and toluene 100ml.Nitrogen again
0.23g bis-triphenylphosphipalladium palladium dichloride is sequentially added after gas displacement.After adding, it is heated to 80 DEG C.Start be added dropwise by
The solution of 39.76g bromo- 2- fluorine dibenzofurans containing 4- (purity 99%, 0.15mol) and 100ml toluene composition, temperature control 75-80
℃.It is cooled to room temperature, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF, obtained
33.52g white product, purity 99%, yield 91%.
Product MS (m/e): 493.53;Elemental analysis (C33H20FN3O): theoretical value C:80.31%, H:4.08%, F:
3.85%, N:8.51%, O:3.24%;Measured value C:80.30%, H:4.09%, F:3.85%, N:8.51%, O:3.24%.
Embodiment 3
The synthesis of compound I-4-2
Synthetic route is as follows:
Specific synthesis step are as follows:
500 milliliters of there-necked flasks, match magnetic agitation, nitrogen displacement after sequentially add sodium carbonate 19.93g (0.188mol),
(9H- carbazole -3- base) boric acid 21.10g (purity 99%, 0.1mol) and toluene 100ml.It is sequentially added after nitrogen displacement again
0.23g bis-triphenylphosphipalladium palladium dichloride.After adding, it is heated to 80 DEG C.Start to be added dropwise by 39.76g bromo- 2- fluorine two containing 4-
The solution of benzofuran (purity 99%, 0.15mol) and 100ml toluene composition, 75-80 DEG C of temperature control.It is cooled to room temperature, is added
The hydrolysis of 100m deionized water, is stirred 10 minutes, and filtering, filter cake is boiled several times repeatedly with DMF, obtains 38.04g white product, pure
Degree 99%, yield 89%.
Product MS (m/e): 427.46;Elemental analysis (C24H14FNO): theoretical value C, 84.29%;H, 4.24%;F,
4.44%;N, 3.28%;O, 3.74%;Measured value C:84.28%, H:4.25%, F, 4.44%;N, 3.28%;O, 3.74%.
The raw materials such as intermediate (4- (diphenylamino) phenyl) boric acid can be from Beijing swallowization set associative light used in the process of test
Power technology Co., Ltd purchase gained.
According to embodiment 1, the technical solution of embodiment 2 and embodiment 3, it is only necessary to which the corresponding raw material of simple replacement does not change
Become any substantive operations, following compound can be synthesized:
Embodiment 4
The present embodiment prepares OLED device in accordance with the following steps:
(1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water
It washes, at acetone/ethanol in the mixed solvent ultrasound 30 minutes, is baked to is completely dried under a clean environment, use ultraviolet rays cleaning
Machine irradiates 10 minutes, and with low energy cation beam bombarded surface;
(2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa, In
It is hole transmission layer that one layer of NPB is deposited on above-mentioned anode tunic, and evaporation rate 0.2nm/s, vapor deposition film thickness is 30nm;
(3) continue to be deposited the compound I-7-2 provided in embodiment 1 on the hole transport layer as material of main part, Ir
(PiQ)3As dopant material (i.e. luminescent material), doping concentration 5% forms the organic luminous layer of device, and evaporation rate is
The film thickness of 0.2nm/s, vapor deposition gained organic luminous layer are 30nm;
(4) continue that electron transfer layer of the one layer of compound BCP as device is deposited on organic luminous layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 40nm;
(5) continue that electron injecting layer of the one layer of LiF as device is deposited on electron transfer layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 10nm;
(6) continue that cathode of the one layer of Al as device is deposited on electron injecting layer, evaporation rate 0.2nm/s steams
Plating film thickness is 60nm;OLED device provided by the invention is obtained, OLED-1 is denoted as.
According to upper identical step, by the compound I-7-2 in step (3) replace with embodiment 2 preparation gained chemical combination
Object I-6-2 obtains OLED-2 provided by the invention.
According to upper identical step, by the compound I-7-2 in step (3) replace with embodiment 3 preparation gained chemical combination
Object I-4-2 obtains OLED-3 provided by the invention.
According to upper identical step, the compound I-7-2 in step (3) is replaced with control compounds 1, and (structure is as follows
It is shown), obtain comparative device OLED-4.
The performance test results of obtained device OLED-1 to OLED-4 are as shown in table 1.
The performance test results of table 1:OLED-1 to OLED-4
It can be seen from the above result that the device OLED-1 being prepared into using organic material shown in Formulas I provided by the invention is extremely
The operating voltage of OLED-3 is lower, brightness under the same conditions, current efficiency obviously than control compounds 1 be used as organic light emission
The device OLED-4 of material of main part is much higher.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of OLED material of main part, which is characterized in that have the structure as shown in general formula I:
In the general formula I, m represents the number of F atom substitution, selected from 1~3 integer;Ar, which is represented, contains n phenyl ring and/or virtue
The aromatic group of heterocycle, the n represent 1~5 integer.
2. OLED material of main part according to claim 1, which is characterized in that have and tied shown in following I ' -1~I ' -7
Structure:
3. OLED material of main part according to claim 1 or 2, which is characterized in that Ar is selected from following group:
4. OLED material of main part according to claim 1 or 2, which is characterized in that Ar is selected from following group:
5. OLED material of main part described in any one according to claim 1~4, which is characterized in that the n represent 3~5 it is whole
Number;
Preferably, the Ar is containing 3~5 phenyl ring and/or heteroaromatic and atom containing N, the fragrance for preferably containing 1~3 N atom
Group.
6. OLED material of main part according to claim 5, which is characterized in that Ar is selected from following group:
7. OLED material of main part according to claim 1, which is characterized in that be selected from following particular compound:
8. the preparation method of OLED material of main part described in claim 1~7 any one, which is characterized in that the reaction mechanism mechanism of reaction is as follows:
Include the following steps:
Using compound A as starting material, withCoupling reaction occurs, obtains compound I;Wherein, m is integer of 1 to 3;
Preferably include following steps:
Using compound A as starting material, using toluene as solvent, using Pd as catalyst, sodium carbonate is alkali, nitrogen protection, temperature control 70-
100 DEG C, compound A withCoupling reaction occurs, obtains compound I.
9. application of the OLED material of main part in organic electroluminescence device described in claim 1~7 any one;
Preferably, the OLED material of main part is used as the light emitting host material of luminescent layer in organic electroluminescence device.
It include OLED described in claim 1~7 any one in organic function layer 10. a kind of organic electroluminescence device
Material of main part;
Preferably, the OLED material of main part is used as the light emitting host material of organic luminous layer in organic function layer;
It is highly preferred that the organic luminous layer with a thickness of 10~100nm, preferably 40~80nm.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910682856.4A CN110407834A (en) | 2019-07-26 | 2019-07-26 | A kind of OLED material of main part and the preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910682856.4A CN110407834A (en) | 2019-07-26 | 2019-07-26 | A kind of OLED material of main part and the preparation method and application thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CN110407834A true CN110407834A (en) | 2019-11-05 |
Family
ID=68363575
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910682856.4A Pending CN110407834A (en) | 2019-07-26 | 2019-07-26 | A kind of OLED material of main part and the preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110407834A (en) |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012049518A (en) * | 2010-07-27 | 2012-03-08 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, compound, organic electroluminescent element, display device, and luminaire |
CN102823016A (en) * | 2010-03-31 | 2012-12-12 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
WO2014065236A1 (en) * | 2012-10-22 | 2014-05-01 | コニカミノルタ株式会社 | Transparent electrode, electronic device, and organic electroluminescence element |
JP2015122247A (en) * | 2013-12-25 | 2015-07-02 | コニカミノルタ株式会社 | Transparent electrode and electronic device |
CN105609649A (en) * | 2014-11-19 | 2016-05-25 | 三星显示有限公司 | Organic electroluminescent device |
KR20170082459A (en) * | 2016-01-06 | 2017-07-14 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
JP2018090561A (en) * | 2016-02-15 | 2018-06-14 | 国立大学法人山形大学 | Novel triazine compound, and organic electronic element and plant-growing lighting that use the same |
WO2018116152A1 (en) * | 2016-12-19 | 2018-06-28 | Idemitsu Kosan Co., Ltd. | Specifically substituted ladder type compounds for organic light emitting devices |
KR20180136377A (en) * | 2017-06-14 | 2018-12-24 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
CN109641916A (en) * | 2016-12-14 | 2019-04-16 | 株式会社Lg化学 | Heterocyclic compound and organic luminescent device comprising it |
-
2019
- 2019-07-26 CN CN201910682856.4A patent/CN110407834A/en active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102823016A (en) * | 2010-03-31 | 2012-12-12 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
JP2012049518A (en) * | 2010-07-27 | 2012-03-08 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, compound, organic electroluminescent element, display device, and luminaire |
WO2014065236A1 (en) * | 2012-10-22 | 2014-05-01 | コニカミノルタ株式会社 | Transparent electrode, electronic device, and organic electroluminescence element |
JP2015122247A (en) * | 2013-12-25 | 2015-07-02 | コニカミノルタ株式会社 | Transparent electrode and electronic device |
CN105609649A (en) * | 2014-11-19 | 2016-05-25 | 三星显示有限公司 | Organic electroluminescent device |
KR20170082459A (en) * | 2016-01-06 | 2017-07-14 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
JP2018090561A (en) * | 2016-02-15 | 2018-06-14 | 国立大学法人山形大学 | Novel triazine compound, and organic electronic element and plant-growing lighting that use the same |
CN109641916A (en) * | 2016-12-14 | 2019-04-16 | 株式会社Lg化学 | Heterocyclic compound and organic luminescent device comprising it |
WO2018116152A1 (en) * | 2016-12-19 | 2018-06-28 | Idemitsu Kosan Co., Ltd. | Specifically substituted ladder type compounds for organic light emitting devices |
KR20180136377A (en) * | 2017-06-14 | 2018-12-24 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
Non-Patent Citations (2)
Title |
---|
JI GWANG YU ET AL.: "A novel molecular design employing a backbone freezing linker for improved efficiency, sharpened emission and long lifetime in thermally activated delayed fluorescence emitters", 《JOURNAL OF MATERIALS CHEMISTRY C: MATERIALS FOR OPTICAL AND ELECTRONIC DEVICES》 * |
MINA JUNG ET AL.: "The effect of frontier orbital distribution of the core structure on the photophysics and device performances of thermally activated delayed fluorescence emitters", 《JOURNAL OF MATERIALS CHEMISTRY C: MATERIALS FOR OPTICAL AND ELECTRONIC DIVICES》 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Wan et al. | Multifunctional electron-transporting indolizine derivatives for highly efficient blue fluorescence, orange phosphorescence host and two-color based white OLEDs | |
TWI614252B (en) | Compound and organic electroluminescence device using the same | |
CN110563746B (en) | Novel SO2 spiro-structure-containing compound and application thereof in OLED (organic light emitting diode) device | |
CN109776395A (en) | A kind of cavitation material and the preparation method and application thereof that fluorine-containing spiral shell two is fluorene structured | |
CN109776396A (en) | A kind of organic compound and the preparation method and application thereof fluorene structured with spiral shell two | |
WO2020211126A1 (en) | Thermally activated delayed fluorescent material, preparation method thereof and organic electroluminescent diode device | |
CN110526901A (en) | A kind of luminous organic material and its application for preparing organic electroluminescence device | |
CN109970577A (en) | It is a kind of with the compound and the preparation method and application thereof fluorene structured containing methylspiro two | |
CN109942440A (en) | A kind of OLED material and the preparation method and application thereof fluorene structured with spiral shell two | |
CN109608383A (en) | A kind of electroluminescent organic material and the preparation method and application thereof | |
CN110003020A (en) | A kind of electroluminescent organic material and the preparation method and application thereof fluorene structured with spiral shell two | |
CN109970578A (en) | A kind of organic compound and the preparation method and application thereof fluorene structured with 9,9 '-spiral shells two | |
CN109879763A (en) | A kind of organic light emission cavitation material and the preparation method and application thereof fluorene structured with spiral shell two | |
CN109776397A (en) | A kind of organic compound and the preparation method and application thereof fluorene structured with 9,9 '-spiral shells two | |
CN110372683A (en) | A kind of electroluminescent organic material and the preparation method and application thereof | |
CN110372676A (en) | A kind of dibenzofurans human subject material and the preparation method and application thereof | |
CN109206368A (en) | A kind of dihydrobenzo indazole class electroluminescent organic material | |
CN110128280A (en) | A kind of organic compound and the preparation method and application thereof | |
CN110143884A (en) | A kind of organic compound and the preparation method and application thereof fluorene structured containing spiral shell two | |
CN110407834A (en) | A kind of OLED material of main part and the preparation method and application thereof | |
CN110143885A (en) | A kind of organic compound and its application fluorene structured with spiral shell two | |
CN110317187A (en) | A kind of organic host material and the preparation method and application thereof | |
CN109678730A (en) | A kind of organic electroluminescent cavitation material and its preparation and application | |
CN110467625B (en) | OLED bipolar main body material and application thereof in device | |
CN110511234A (en) | A kind of new type heterocycle spirane structure compound and its application in OLED device |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20191105 |