CN116253725A - Electron transport material and organic electroluminescent device - Google Patents
Electron transport material and organic electroluminescent device Download PDFInfo
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- CN116253725A CN116253725A CN202111501975.9A CN202111501975A CN116253725A CN 116253725 A CN116253725 A CN 116253725A CN 202111501975 A CN202111501975 A CN 202111501975A CN 116253725 A CN116253725 A CN 116253725A
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- 239000000463 material Substances 0.000 title claims abstract description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 8
- 125000000732 arylene group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- BGTFRFFRQKBWLS-UHFFFAOYSA-M lithium;quinolin-2-olate Chemical compound [Li+].C1=CC=CC2=NC([O-])=CC=C21 BGTFRFFRQKBWLS-UHFFFAOYSA-M 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012536 packaging technology Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an electron transport material and an organic electroluminescent device, which are provided with a compound
Wherein R is 1 Is hydrogen, deuterium, a halogen atom, cyano, nitro, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted amino, or substituted or unsubstituted aryl; l is a direct bond, a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene; ar (Ar) 1 And Ar is a group 2 Each independently is a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl; x is X 1 To X 3 Are identical or different from one another and are each independently N or CR ', where R' is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substitutedOr unsubstituted aryl or substituted or unsubstituted heteroaryl. The technical scheme of the invention not only has lower voltage, but also has higher efficiency.
Description
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to an electron transport material and an organic electroluminescent device with the electron transport material.
Background
The organic electroluminescence refers to a phenomenon in which a light emitting material converts electric energy into light energy under the action of an electric field. Compared with the inorganic electroluminescence with earlier development, the organic electroluminescence has the advantages of wide material selectivity, realization of full-color display from a blue light area to a red light area, low driving voltage, high luminous brightness and luminous efficiency, wide viewing angle, high response speed, relatively simple manufacturing process, low cost, realization of flexible display and the like.
The Organic Light Emitting Diode (OLED) is mainly applied to aspects of organic flat panel display (OLED), organic solar cells, organic electronic circuits and the like, and the material selection range is quite wide. Since the visual information accounts for about 70% of the total information, the display technology is the main bridge for connecting modern society people and information, and along with the rapid development of the information technology, people are urgent to demand a lighter and thinner high-performance flat panel display device.
As a member of flat panel display, organic electroluminescent devices (OLED), particularly white organic electroluminescent devices, have been under a strong potential advantage in full color display, backlight of liquid crystal, solid state lighting, and the like, and have been under a strong research on the global scale in recent years.
Although the progress of the industrialization of organic electroluminescent display devices has been greatly advanced, there are still many important basic problems in the light emitting materials, colorization technology, film formation technology, active driving technology, packaging technology, etc. of the OLED. This results in shorter device life, lower efficiency, and high cost due to the immaturity of the process.
Therefore, the invention provides the electron transport material with the advantages of low voltage, high efficiency and the like and the organic electroluminescent device with the electron transport material.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide an electron transport material and an organic electroluminescent device with the electron transport material, which not only have lower voltage, but also have higher efficiency.
According to an aspect of the present invention, there is provided an electron transport material, a compound having a structure represented by formula I:
wherein R is 1 Is hydrogen, deuterium, a halogen atom, cyano, nitro, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted amino, or substituted or unsubstituted aryl;
l is a direct bond, a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene;
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
X 1 to X 3 Are identical or different from one another and are each independently N or CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
Preferably: the R is 1 Is a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted heteroarylamino group, or a substituted or unsubstituted heteroaryl group.
Preferably: the R is 1 Is alkyl, cyano, aryl or heteroaryl.
Preferably: the R is 1 Is a heteroarylene group containing an N atom.
Preferably: and L is a heteroarylene group containing an N atom.
Preferably: the X is 1 To X 3 At least two of which are N.
Preferably: the X is 1 To X 3 At least one of which is CR ', R' is hydrogen, deuterium, aryl or heteroaryl containing an N atom.
Preferably: the Ar is as follows 1 And Ar is a group 2 Each independently is a heteroaryl group containing N, O or S.
Preferably: the compound shown in the formula I is:
according to another aspect of the present invention, there is also provided an organic electroluminescent device in which the above electron transport material is doped.
Preferably: the electron transport material is doped in the electron transport layer of the device.
The electron transport material and the organic electroluminescent device with the electron transport material have low voltage and high efficiency.
Detailed Description
Example embodiments will now be described more fully with reference to the examples. However, the example embodiments may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art.
In an embodiment of the present invention, there are provided an electron transport material and an organic electroluminescent device having the same, a compound having a structure represented by formula I:
wherein L is a directly bonded, substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.
R 1 Is hydrogen, deuterium, halogen atom, cyano, nitro, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted silyl, substituted or unsubstituted aminoUnsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
Ar 1 And Ar is a group 2 Each independently is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
X 1 To X 3 Are identical or different from one another and are each independently N or CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
The electron transport material and the organic electroluminescent device with the electron transport material have the advantages of low voltage and high efficiency.
In embodiments of the present invention, the preferred compounds of the structure shown in formula I are:
the following specific examples illustrate the invention:
the synthetic formulas for preparing compounds 1-26 are as follows:
compound 1
The synthetic method for preparing compound 1 is as follows:
into a 200mL three-necked flask, 0.85g of intermediate A,1g of anhydrous cesium carbonate powder and 0.2g of Pd2dba3 were successively added, followed by addition of 100mL of anhydrous 1, 4-dioxane, and stirring was carried out uniformly. During the process, nitrogen is supplemented and vacuum is pumped, so that the reaction is in nitrogen atmosphere. Heating and maintaining the temperature at 140 ℃, dropwise adding 0.46g of the intermediate B, carrying out light-proof reflux reaction for 18h, and tracking a spot plate until the reaction is complete. After recrystallization at a reduced temperature, chromatography on a column gave 1.07g of Compound 1 (yield 83%).
Compounds 2-26
The synthetic method for preparing the compounds 2-26 is similar to the compound 1, and only the corresponding different intermediates A and B are added, and corresponding reaction conditions are selected.
Control test
Examples 1 to 8
The organic light emitting elements 1 to 8 are sequentially prepared by the compounds 1 to 8 prepared by the method.
The organic light-emitting element 1-8 comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode from bottom to top.
The constituent materials of the layers of the organic light emitting elements 1 to 8 are as follows:
anode: ITO (indium tin oxide) with thickness of
Hole injection layer: hexanitrile Hexaazatriphenylene (HAT) with a thickness of
Hole transport layer: n4, N4, N4', N4' -tetrakis ([ 1,1' -biphenyl) of the formula]-4-yl) - [1,1' -biphenyl]-4,4' -diamine of thickness of
Light emitting layer: the mass ratio of the host material BH to the guest material BD is 25:1, a step of; thickness is as follows
Electron transport layer: host material compounds 1-8, guest material LiQ, mass ratio of host and guest materials is 1:1, a step of; thickness of (L)
And (3) cathode: liF and aluminum.
The method comprises the following steps:
coating the material with a certain thickness
The glass substrate of the Indium Tin Oxide (ITO) film was put into distilled water in which a detergent was dissolved, and washed using ultrasonic waves. In this case, a product manufactured by Fischer co. Was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore c. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice using distilled water for 10 minutes. After the washing with distilled water was completed, ultrasonic washing was performed using isopropanol, acetone and methanol solvents, and the resultant product was dried and then transferred to a plasma washing machine. Furthermore, the substrate was cleaned for 5 minutes by using oxygen plasmaWhich is then patented to a vacuum depositor.
Thermal vacuum deposition onto transparent electrodes thus prepared using hexanitrile Hexaazabenzophenanthrene (HAT)
Thereby forming a hole injection layer. />
The compound N4, N4, N4', N4' -tetrakis ([ 1,1' -biphenyl) was used]-4-yl) - [1,1' -biphenyl]-4,4' -diamine
Vacuum deposition is performed on the hole injection layer, thereby forming a hole transport layer.
Subsequently, BH and BD were used to vacuum deposit onto the hole transport layer to a weight ratio of 25:1
To thereby form a light emitting layer.
Vacuum depositing a compound 1 and a compound LiQ (lithium quinolinolate) on the light-emitting layer at a weight ratio of 1:1, thereby forming a film having a thickness of
Electron injection and transport layers of (a) are provided.
Sequentially depositing lithium fluoride (LiF) and aluminum on the electron injection and transport layers, respectively
And->
Thereby forming a negative electrode.
In the foregoing process, the deposition rate of the organic material is maintained at
To->
By negatively chargingThe deposition rates of lithium fluoride and aluminum of the pole are maintained at +.>
To->
And the vacuum degree during deposition is maintained at 2×10 -7 To 5X 10 -6 The support, thereby manufacturing the organic light emitting device.
Comparative example 1
The organic light emitting element 9 is prepared. The organic light-emitting elements 1 to 8 prepared from the compounds 1 to 8 are different in that: ET1 was used in place of the compounds 1 to 8 in the electron transport layer in the organic light-emitting element 9, and the rest was the same.
Performance testing
The organic light emitting elements 1 to 8 prepared in examples 1 to 8 of the present invention and the organic light emitting element 9 prepared in comparative example 1 were subjected to the following performance tests:
when a current was applied to the organic light-emitting elements 1 to 9, a voltage (V@10mA/cm was measured 2 ) Efficiency (Cd/A@10mA/cm) 2 ) And service life. Where T95 refers to the time taken for the luminance to decrease to 95% of the initial luminance (5000 nit).
The performance test results are shown in table 1:
table 1: test results
| Classification | Electron transport layer | Voltage (V) | Efficiency of | T95 (hours) |
| Organic light-emitting element 1 | Compound 1 LiQ | 3.71 | 5.51 | 480 |
| Organic light-emitting element 2 | Compound 2:LiQ | 3.83 | 5.62 | 450 |
| Organic light-emitting element 3 | Compound 3 LiQ | 3.72 | 5.74 | 430 |
| Organic light-emitting element 4 | Compound 4 LiQ | 3.90 | 5.80 | 490 |
| Organic light-emitting element 5 | Compound 5 LiQ | 3.74 | 5.76 | 470 |
| Organic light-emitting element 6 | Compound 6 LiQ | 3.53 | 5.55 | 480 |
| Organic light-emitting element 7 | Compound 7 LiQ | 3.68 | 5.65 | 460 |
| Organic light-emitting element 8 | Compound 8 LiQ | 3.75 | 5.69 | 465 |
| Organic light-emitting element 9 | ET1:LiQ | 4.05 | 4.96 | 310 |
As can be seen from the performance data of table 1, the organic light emitting element made of the material of the example of the present invention exhibits better performance in terms of current efficiency, driving voltage and service life than the comparative example.
In summary, the electron transport material and the organic electroluminescent device with the electron transport material have low voltage and high efficiency.
The foregoing is a further detailed description of the invention in connection with the preferred embodiments, and it is not intended that the invention be limited to the specific embodiments described. It will be apparent to those skilled in the art that several simple deductions or substitutions may be made without departing from the spirit of the invention, and these should be considered to be within the scope of the invention.
Claims (10)
1. An electron transport material characterized by a compound having a structure represented by formula I:
wherein R is 1 Is hydrogen, deuterium, a halogen atom, cyano, nitro, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted amino, or substituted or unsubstituted aryl;
l is a direct bond, a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene;
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
X 1 to X 3 Are identical or different from one another and are each independently N or CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
2. The electron transport material according to claim 1, wherein: the R is 1 Is a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted heteroarylamino group, or a substituted or unsubstituted heteroaryl group.
3. The electron transport material according to claim 1, wherein: the R is 1 Is alkyl, cyano, aryl or heteroaryl.
4. The electron transporting material according to claim 3, whereinThe method comprises the following steps: the R is 1 Is a heteroarylene group containing an N atom.
5. The electron transport material according to claim 1, wherein: and L is heteroaryl containing N atoms.
6. The electron transport material according to claim 1, wherein: the X is 1 To X 3 At least two of which are N.
7. The electron transport material according to claim 1, wherein: the X is 1 To X 3 At least one of which is CR ', R' is hydrogen, deuterium, aryl or heteroaryl containing an N atom.
8. The electron transport material according to claim 1, wherein: the Ar is as follows 1 And Ar is a group 2 Each independently is a heteroaryl group containing N, O or S.
9. The electron transport material according to claim 1, wherein: the compound shown in the formula I is:
10. an organic electroluminescent device, characterized in that: an organic electroluminescent device doped with an electron transporting material according to any one of claims 1 to 9.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111501975.9A CN116253725A (en) | 2021-12-09 | 2021-12-09 | Electron transport material and organic electroluminescent device |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111501975.9A CN116253725A (en) | 2021-12-09 | 2021-12-09 | Electron transport material and organic electroluminescent device |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107001334A (en) * | 2014-12-12 | 2017-08-01 | 默克专利有限公司 | Organic compound with soluble groups |
| CN107522705A (en) * | 2017-09-29 | 2017-12-29 | 江苏三月光电科技有限公司 | A kind of oxa anthracenes organic compound and its application on OLED |
| CN107556297A (en) * | 2017-09-29 | 2018-01-09 | 江苏三月光电科技有限公司 | A kind of oxa anthracenes organic compound and its application |
| CN107652297A (en) * | 2017-09-29 | 2018-02-02 | 江苏三月光电科技有限公司 | A kind of oxa anthracenes organic compound and its application in OLED |
-
2021
- 2021-12-09 CN CN202111501975.9A patent/CN116253725A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107001334A (en) * | 2014-12-12 | 2017-08-01 | 默克专利有限公司 | Organic compound with soluble groups |
| CN107522705A (en) * | 2017-09-29 | 2017-12-29 | 江苏三月光电科技有限公司 | A kind of oxa anthracenes organic compound and its application on OLED |
| CN107556297A (en) * | 2017-09-29 | 2018-01-09 | 江苏三月光电科技有限公司 | A kind of oxa anthracenes organic compound and its application |
| CN107652297A (en) * | 2017-09-29 | 2018-02-02 | 江苏三月光电科技有限公司 | A kind of oxa anthracenes organic compound and its application in OLED |
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