CN110372676A - A kind of dibenzofurans human subject material and the preparation method and application thereof - Google Patents
A kind of dibenzofurans human subject material and the preparation method and application thereof Download PDFInfo
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Abstract
The present invention relates to a kind of dibenzofurans human subject materials, have the structure as shown in general formula I.Novel material of main part 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, realizes the transmission balance of hole and electronics in transmission 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 dibenzofurans human subject material:
In dibenzofurans main structure shown in general formula I, any one phenyl ring is simultaneously by 1 aromatic group Ar and m
Methyl replaces, and the m can be selected from 1,2,3 or 4.
As a preferred solution of the present invention, structure shown in general formula I is as follows:
Wherein, m represents the substitution number of methyl on phenyl ring, can be selected from 1,2,3 or 4.
Specifically, 1,2,3 or 4 methyl may replace Formulas I ' shown in structure 1,2,3 and/or No. 4 position on hydrogen it is former
Son.
As m=1, methyl may replace Formulas I ' shown in hydrogen atom on 1,2,3, the 4 of structure any one position, i.e., it is described
Structure shown in optional ' -1 of the Formulas I freely~I ' -4 of organic material, the structure shown in ' -2 preferably such as Formulas I.
As m=2, methyl may replace Formulas I ' shown in structure 1,2,3, No. 4 any two position on hydrogen atom, i.e. institute
State structure shown in optional ' -5 of the Formulas I freely~I ' -10 of organic material.
As m=3, methyl may replace Formulas I ' shown in structure 1,2,3, No. 4 any three position on hydrogen atom, i.e. institute
State structure shown in optional ' -11 of the Formulas I freely~I ' -14 of organic material:
As m=4, methyl may replace Formulas I ' shown in structure 1,2,3, No. 4 four position of whole on hydrogen atom, i.e. institute
State structure shown in optional ' -15 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 1,2,3 or 4, the specific substitution mode of methyl 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.HOMO-
LUMO energy gap can also be changed by being alkylated, to optimize the injection of carrier, adjust the work electricity of electroluminescent device
Pressure and efficiency.
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 comprises the following specific steps that:
Using compound A as starting material, using toluene as solvent, using Pd as catalyst, sodium carbonate is alkali, nitrogen protection, control
Warm 70-100 DEG C, 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 material shown in general formula I in organic electroluminescence device.The present invention is excellent
The material is selected to be 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
Material.The preferably described material of the present invention is used as the light emitting host material of organic luminous layer in organic function layer.Organic hair
The thickness of photosphere 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, realizes in transmission luminescent layer
The transmission of hole and electronics balances；Triplet also with higher effectively prevents energy in luminescence process from returning to master
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-6-2)
Synthetic route is as follows:
The synthesis of compound I-6-2
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 bis-triphenylphosphipalladium palladium dichloride.After adding, it is heated to 80 DEG C.Start to be added dropwise (pure by 39.17g A containing compound
Spend 99%, 0.15mol) and 100ml toluene form solution, 80-100 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 38.29g white product, purity 99%, yield
80%.
Product MS (m/e): 425.52；Elemental analysis (C31H23NO): theoretical value C:87.50%, H:5.45%, N:
3.29%, O:3.76%；Measured value C:87.49%, H:5.46%, N:3.29%, O:3.76%.
Embodiment 2
The synthesis of (compound I-8-2)
Synthetic route is as follows:
The synthesis of compound I-8-2
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 39.17g A containing compound (purity 99%, 0.15mol) and 100ml toluene composition, 80-100 DEG C of temperature control.It is cooled to room
Temperature is added the hydrolysis of 100m deionized water, stirs 10 minutes, and filtering, filter cake is boiled several times repeatedly with DMF, obtains 44.55g white
Product, purity 99%, yield 91%.
Product MS (m/e): 489.57；Elemental analysis (C33H23N3O): theoretical value C:83.41%, H:4.74%, N:8.58；
O:3.27%；Measured value C:83.40%, H:4.75%, N:8.58；O:3.27%.
Embodiment 3
The synthesis of (compound I-4-2)
Synthetic route is as follows:
The synthesis of compound I-4-2
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 (pure by 39.17g A containing compound
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 37.69g white product, purity 99%, yield
89%.
Product MS (m/e): 423.50；Elemental analysis (C31H21NO): theoretical value C:87.92%, H:5.00%, N:
3.31%, O:3.78%；Measured value C:87.90%, H:5.02%, N:3.31%, O:3.78%.
Intermediate (4- (diphenylamino) phenyl) boric acid etc. can be from Beijing swallowization set associative photoelectricity skill used in the process of test
Art 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,
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-6-2 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-6-2 in step (3) replace with embodiment 2 preparation gained chemical combination
Object I-8-2 obtains OLED-2 provided by the invention.
According to upper identical step, by the compound I-6-2 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-6-2 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 dibenzofurans human subject material, which is characterized in that have the structure as shown in general formula I:
In the general formula I, m represents methyl substituted number, selected from 1~4 integer；Ar represents miscellaneous containing n phenyl ring and/or virtue
The aromatic group of ring, the n represent 1~5 integer.
2. material of main part according to claim 1, which is characterized in that have structure shown in following I ' -1~I ' -15:
3. material of main part according to claim 1 or 2, which is characterized in that Ar is selected from following group:
4. material of main part according to claim 1 or 2, which is characterized in that Ar is selected from following group:
5. material of main part described in any one according to claim 1~4, which is characterized in that the n represents 3~5 integer；
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. material of main part according to claim 5, which is characterized in that Ar is selected from following group:
7. 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 material of main part described in claim 1~7 any one in organic electroluminescence device；
Preferably, the material of main part is used as the light emitting host material of luminescent layer in organic electroluminescence device.
It include main body described in claim 1~7 any one in organic function layer 10. a kind of organic electroluminescence device
Material；
Preferably, the 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.
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| WO2022220346A1 (en) * | 2021-04-14 | 2022-10-20 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
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