CN114105954A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
- Publication number
- CN114105954A CN114105954A CN202010898673.9A CN202010898673A CN114105954A CN 114105954 A CN114105954 A CN 114105954A CN 202010898673 A CN202010898673 A CN 202010898673A CN 114105954 A CN114105954 A CN 114105954A
- Authority
- CN
- China
- Prior art keywords
- compound
- hours
- substituted
- layer
- electron transport
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a compound and application thereof, wherein the compound has a structure shown in a formula I, and the compound can be used as an electron transport material, and not only has higher stability, but also has high charge transfer capacity and high glass transition temperature. The organic electroluminescent device has high luminous efficiency, low driving voltage and long service life. The compound of the invention is used as an electron transport material, so that the current efficiency of the organic electroluminescent device is more than or equal to 5.8Cd/A, the driving voltage is less than or equal to 3.9V, and the service life LT95 is more than or equal to 116 h.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to a compound and application thereof.
Background
The organic electroluminescent element has a structure in which a light-emitting layer containing a light-emitting material is sandwiched between a hole-transporting layer and an electron-transporting layer, and an anode and a cathode are attached to both outer sides of the sandwich structure. Organic electroluminescent devices are devices that emit light (fluorescence or phosphorescence) when excitons generated by recombination of holes and electrons injected into a light-emitting layer are deactivated, and are used for displays and the like.
In order for the organic light emitting device to have sufficiently excellent characteristics, materials forming the organic material layer, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like, first need to be supported by stable and effective materials, however, the development of stable and effective materials for the organic material layer currently used for the organic light emitting device is still insufficient.
CN109180581A discloses an organic luminescent compound, wherein acridine functional groups with high electron hole transport efficiency and triarylamine with excellent hole transport performance are combined to form a compound with high thermal stability and excellent luminescent efficiency, and introduction of different substituents can change electron transition and adjust the luminescent peak position of the compound.
In the art, there is an important significance to the continuous development of materials capable of making organic light emitting devices have sufficiently excellent characteristics.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a compound and application thereof. The compound can be used as an electron transport material, and not only has higher stability, but also has high charge transfer capacity and high glass transition temperature.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a compound having the structure shown in formula I below:
wherein X1-X4Each independently is hydrogen or nitrogen, and at least one is nitrogen; r1And R2Independently selected from hydrogen, substituted or unsubstituted C6-C60Aryl radical, substituted or unsubstituted C6-C60Heteroaryl radical, substituted or unsubstituted C1-C50An alkyl group.
In the present invention, the substituted or unsubstituted C6-C60 aryl group may be a substituted or unsubstituted C6, C8, C10, C12, C15, C18, C20, C23, C25, C28, C30, C33, C35, C38, C40, C43, C45, C48, C50, C53, C55, C58, or C60 aryl group. The substituted or unsubstituted C6-C60 heteroaryl group may be a substituted or unsubstituted C6, C8, or C8 heteroaryl group, and the substituted or unsubstituted C8-C8 alkyl group may be a substituted or unsubstituted C8, or C8 alkyl group.
Preferably, R1And R2Independently selected from any one of hydrogen, phenyl, naphthyl, anthryl, phenanthryl, quinonyl, fluorenyl, spirofluorenyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, benzofuryl, benzimidazolyl, quinolyl, isoquinolyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Preferably, when R is1And R2Independently selected from substituted C6-C60Aryl radical, substituted C6-C60Heteroaryl radical or substituted C1-C50In the case of alkyl groups, the substituents are selected from phenyl, naphthyl, anthracenyl, diphenylpyrimidine, benzimidazole, carbazole, methyl, ethyl or tert-butyl.
Preferably, R1And R2Independently hydrogen, phenyl, tert-butyl or
Wherein the wavy line indicates the linkage of the group.
Preferably, the compound is selected from any one of compounds a-D:
in the present invention, the compounds of formula I can be prepared according to the following synthetic route:
reacting the compound 1 in the step (a) with a brominating agent to obtain a compound 2.
Preferably, the brominating reagent is N-bromosuccinimide.
Preferably, the molar ratio of compound 1 to brominating reagent is 1:2 to 2.5, e.g. 1:2, 1:2.1, 1:2.2, 1:2.3, 1:2.4, 1: 2.5.
Preferably, the temperature of the reaction of step (a) is 70-90 ℃, e.g. 70 ℃, 73 ℃, 75 ℃, 78 ℃, 80 ℃, 82 ℃, 85 ℃, 88 ℃ or 90 ℃. The reaction was monitored by HPLC until completion.
Preferably, in step (b), compound 2 is dissolved in tetrahydrofuran solution containing furan, and sec-butyl potassium oxide is added to react to obtain compound 3.
Preferably, the volume ratio of furan to tetrahydrofuran is 2: 1.
Preferably, the molar ratio of sec-butyl potassium oxide to compound 2 in step (b) is 3-5:1, such as 3:1, 3.3:1, 3.5:1, 3.8:1, 4:1, 4.3:1, 4.5:1, 4.8:1 or 5: 1.
Preferably, the reaction of step (b) is stirred at 0 ℃ for 1 to 3 hours (e.g. 1 hour, 1.5 hours, 2 hours, 2.5 hours or 3 hours) and then warmed to room temperature for 5 to 12 hours (e.g. 5 hours, 7 hours, 9 hours, 10 hours or 12 hours).
Preferably, in step (C) compound 3 is hydrogenated under Pd/C catalysis to give compound 4.
Preferably, the reaction of step (c) is carried out at room temperature for a reaction time of 3 to 6 hours, such as 3 hours, 4 hours, 5 hours or 6 hours.
And (d) heating the compound 4 and p-toluenesulfonic acid for reflux reaction to obtain a compound 5.
Preferably, the molar ratio of compound 4 to p-toluenesulfonic acid is 1:2 to 2.5, such as 1:2, 1:2.1, 1:2.2, 1:2.3, 1:2.4, 1: 2.5.
Preferably, the heating reflux reaction is carried out for a period of 5 to 12 hours, such as 5 hours, 7 hours, 9 hours, 10 hours or 12 hours.
The compound 6 in the step (e) reacts with the compound 5 in the presence of n-butyllithium to obtain a compound 7.
Preferably, the molar ratio of compound 6 to compound 5 is 1:1 to 1.5, such as 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4 or 1: 1.5.
Preferably, the n-butyllithium is added to the reaction system at-78 ℃.
Preferably, the reaction of step (e) is carried out at room temperature for a period of 5 to 12 hours, for example 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours or 12 hours.
In the step (f), the compound 7 is subjected to ring-closing reaction under acidic conditions to obtain a compound 8.
Preferably, the acidic condition is carried out in the presence of a mixed acid of hydrochloric acid and acetic acid.
Preferably, the reaction of step (f) is carried out at reflux for a period of 5 to 12 hours, for example 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours or 12 hours.
Reacting the compound 8 with the compound 9 in the step (g) to obtain the compound shown in the formula I.
Preferably, the molar ratio of compound 8 to compound 9 is 1:1 to 1.5, such as 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4 or 1: 1.5.
Preferably, the reaction medium of the reaction of step (g) is a mixture of dioxane and cesium fluoride.
Preferably, the reaction of step (g) is carried out over a bis (tricyclohexylphosphine) palladium dichloride catalyst.
Preferably, the reaction of step (g) is carried out under reflux for a period of 10 to 48 hours, for example 10 hours, 12 hours, 15 hours, 18 hours, 20 hours, 24 hours, 28 hours, 30 hours, 33 hours, 36 hours, 38 hours, 40 hours, 46 hours, 48 hours.
In another aspect, the present invention provides an electron transport material comprising a compound as described above.
In another aspect, the present invention provides the use of an electron transport material as described above in an organic electroluminescent device.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode and an organic functional layer between the anode and the cathode, wherein an electron transport layer of the organic functional layer comprises a compound as described above.
Preferably, the compound as described above is used as a host material in the electron transport layer.
Preferably, the organic functional layer further comprises any one or a combination of at least two of a light emitting layer, an electron blocking layer, an electron injection layer, a hole blocking layer or a hole transport layer.
Compared with the prior art, the invention has the following beneficial effects:
the compound of the invention can be used as an electron transport material, and has high stability, high charge transfer capacity and high glass transition temperature. The organic electroluminescent device has high luminous efficiency, low driving voltage and long service life. The compound of the invention is used as an electron transport material, so that the current efficiency of the organic electroluminescent device is more than or equal to 5.8Cd/A, the driving voltage is less than or equal to 3.9V, and the service life LT95 is more than or equal to 116 h.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The reagents used in the following synthesis examples are commercially available and the test instruments used to characterize the structure of the compounds are as follows:
(1) melting Point
The melting point of the product was measured by a Differential Scanning Calorimeter (DSC) model PE Instruments DSC 2920, manufactured by Xiamen Star Ed corporation, with the following test parameters: the test range is 50-400 ℃, and the heating rate is 10 ℃/min.
(2) Chemical structure and purity
The product was tested for its hydrogen nuclear magnetic resonance spectrum by an AVANCE 800 nuclear magnetic resonance apparatus (NMR) manufactured by Bruker, Switzerland (R) ((R))1HNMR), the solvents adopted by the nuclear magnetic resonance spectrum test are all CDCl3The magnetic field intensity of the hydrogen atomic nuclear magnetic resonance spectrum test is 400MHz, the chemical structure and the purity of the product are judged by the spectrogram, and the purity is recorded as [1- (the ratio of the area of the hetero peak to the area of the product peak)]×100％。
Example 1
The synthesis method of the compound A comprises the following steps:
(a) 354mmol of compound 1, 708mmol of N-bromosuccinimide and 3.54mmol of benzoyl peroxide were dissolved in carbon tetrachloride (430ml), the mixture was heated to 85 ℃ and the reaction was monitored by HPLC, after completion of the reaction, the precipitate was removed by filtration and washed with methanol, followed by purification by recrystallization, and the purified product was concentrated to dryness to give compound 2.
(b) 289mmol of compound 2 is dissolved in furan/tetrahydrofuran (2/1,960 ml in volume ratio), the reaction is cooled to 0 ℃, 867mmol of sec-butyl potassium oxide is added, the reaction is stirred for 1 hour at 0 ℃ and then warmed to room temperature and stirred for 12 hours, after the reaction is completed, the reaction is stopped by deionized water, an organic layer is extracted by a solvent and dried by sodium sulfate, the solvent is removed from the organic layer by reduced pressure distillation, the generated residue is purified by silica gel tube column chromatography, and the purified product is concentrated and dried to finally obtain the compound 3.
(c) 173mmol of compound 3 and 4mmol, 5% Pd/C in 535ml ethyl acetate were suspended, the reaction was stirred under hydrogen for 3-6 hours, the resulting mixture was filtered through celite and washed with ethyl acetate, and the filtrate was concentrated under reduced pressure to give compound 4.
(d) After heating 170mmol of compound 4 and 340mmol of p-toluenesulfonic acid in 530ml of toluene under reflux for 12 hours, the mixture was cooled to room temperature, quenched with a saturated aqueous solution of sodium bicarbonate, extracted with dichloromethane, the organic layer was washed with water and brine in this order, dried over anhydrous sodium sulfate, and the resulting solution was concentrated under reduced pressure and purified by silica gel column chromatography using dichloromethane/hexane (volume ratio 1/1) as a eluent, to give compound 5.
(e) 64mmol of compound 6 are introduced into 400ml of THF at-78 ℃. At this temperature 30ml of BuLi (2M in hexane) were added dropwise. After 1 hour, 200ml of THF containing 94mmol of compound 5 are added dropwise. The batch was allowed to stir at room temperature overnight, added to ice-water and extracted with dichloromethane. The combined organic phases were washed with water and dried over sodium sulfate. Removal of the solvent in vacuo afforded the crude compound 7.
(f) The crude compound 7 was heated under reflux at 100 ℃ overnight with 30ml HCl and 300ml AcOH. After cooling, the precipitated solid is filtered off with suction, washed once with 100ml of water, three times with 100ml of ethanol each time and subsequently recrystallized from heptane to give compound 8.
(g) 46.3mmol of compound 8 and 46.3mmol of compound 9 are suspended in 300ml of dioxane and 92.6mmol of cesium fluoride. To the suspension was added 5.56mmol of bis (tricyclohexylphosphine) palladium dichloride, and the reaction mixture was heated at reflux for 24 hours. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 100ml of water and subsequently evaporated to dryness. After filtration of the crude product through silica gel with toluene, the residue left is recrystallized from heptane/toluene and finally sublimed in high vacuum to give compound a.
The yield of compound a was 82%. Characterization data: melting point (DSC)319 deg.C, purity 99.9%;1H NMR(400MHz,CDCl3)δ(ppm)：8.53-7.87(m,2H),7.54-7.40(m,8H),7.34-7.28(m,9H),7.22-7.15(m,5H),7.13-6.89(m,4H).
example 2
The synthesis of compound B is similar to that of compound a in example 1, except for the starting materials used.
The yield of compound B was 78%. Characterization data: melting point (DSC) of 328 ℃ and purity of 99.9 percent;1H NMR(400MHz,CDCl3)δ(ppm)：8.54-7.54(m,6H),7.50-7.40(m,6H),7.37-3.31(m,5H),7.29-7.22(m,7H),7.17-6.89(m,7H).
example 3
The synthesis of compound C was similar to that of compound a in example 1, except that only the starting material was used.
The yield of compound C was 86%. Characterization data: melting point (DSC)267 deg.C, purity 99.9%;1H NMR(400MHz,CDCl3)δ(ppm)：8.57-7.48(m,6H),7.36-7.28(m,7H),7.24-7.14(m,5H),7.12-7.08(m,5H).
example 4
The synthesis of compound D is similar to that of compound a in example 1, except for the starting materials used.
The yield of compound D was 89%. Characterization data: melting point (DSC)253 ℃ and purity 99.9%;1H NMR(400MHz,CDCl3)δ(ppm)：9.01(s,1H),8.29-7.36(m,6H),7.28-7.10(m,9H),7.04(s,1H),1.34(s,9H).
application examples 1 to 4 and comparative example 1
The preparation method of the OLED device comprises the following steps: an ITO anode is formed on a substrate with a reflecting layer, and an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, an electron transport layer, an electron injection layer, a cathode and a covering layer are sequentially evaporated.
The constituent materials of the layers were as follows:
hole injection layer: HAT-CN with a thickness of 10 nm;
hole transport layer: NPD with a thickness of 120 nm;
an electron blocking layer: TCTA with a thickness of 10 nm;
light-emitting layer: the material comprises a host material ADN and a guest material t-Bu-Perylene, wherein the mole percentage content of the guest material is 5%; the thickness is 30 nm;
electron transport layer: the host material is the compound or BPhen of the invention, the guest material Liq, the host material and the guest material, and the thickness and the molar percentage content thereof are shown in Table 1;
cathode: Mg/Ag with the ratio of 9:1 and the thickness of 15 nm;
covering layer: the covering material DNTPD is 65nm thick.
TABLE 1
| Serial number | Thickness of electron transport layer | Host and guest materials for electron transport layers |
| Application example 1 | 35nm | The compound A (50%) is Liq (50%) |
| Application example 2 | 35nm | The compound B (50%) is Liq (50%) |
| Application example 3 | 35nm | The compound C (50%) is Liq (50%) |
| Application example 4 | 35nm | Compound D (50%) Liq (50%) |
| Comparative example 1 | 35nm | BPhen(50％):Liq(50％) |
In the above application examples and comparative examples, the abbreviations for the materials correspond to the following structural formulae:
testing the performance of the device:
the OLED devices provided in the application examples and comparative examples were subjected to a test of luminous efficiency, which includes efficiency, driving voltage, and lifetime (LT95, time for luminance to decay to 95%).
Wherein, the photoelectric performance data of the device is 10mA/cm at the current density2Measured at a current density of 25mA/cm for life (LT95) data2Calculated under the condition.
The results of the performance tests are shown in table 2 below:
TABLE 2
| Item | Efficiency (Cd/A) | V(V) | LT95(hr) |
| Application example 1 | 6.3 | 3.9 | 172 |
| Application example 2 | 6.2 | 3.7 | 123 |
| Application example 3 | 6.6 | 3.7 | 116 |
| Application example 4 | 5.8 | 3.8 | 186 |
| Comparative example 1 | 4.8 | 4.0 | 100 |
As can be seen from the performance data in the table, the material of the present invention is highly suitable for use as an electron transport material in OLED devices and has good electron transport properties. Compared with the BPhen material of a comparative example, the material of the invention has higher efficiency (more than or equal to 5.8Cd/A), lower voltage (less than or equal to 3.9V) and longer service life (more than or equal to 116 h).
The applicant states that the invention is illustrated by the above examples of the compounds of the invention and their use, but the invention is not limited to the above examples, i.e. it is not intended that the invention necessarily depends on the above examples for its practice. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A compound having the structure shown in formula I:
wherein X1-X4Each independently is hydrogen or nitrogen, and at least one is nitrogen; r1And R2Independently selected from hydrogen, substituted or unsubstituted C6-C60Aryl radical, substituted or unsubstituted C6-C60Heteroaryl radical, substituted or unsubstituted C1-C50An alkyl group.
2. A compound of claim 1, wherein R is1And R2Independently selected from any one of hydrogen, phenyl, naphthyl, anthryl, phenanthryl, quinonyl, fluorenyl, spirofluorenyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, benzofuryl, benzimidazolyl, quinolyl, isoquinolyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
3. A compound according to claim 1 or 2, wherein when R is1And R2Independently selected from substituted C6-C60Aryl radical, substituted C6-C60Heteroaryl radical or substituted C1-C50In the case of alkyl groups, the substituents are selected from phenyl, naphthyl, anthracenyl, diphenylpyrimidine, benzimidazole, carbazole, methyl, ethyl or tert-butyl.
4. The method of any one of claims 1-3Characterized in that R is1And R2Independently hydrogen, phenyl, tert-butyl or
Wherein the wavy line indicates the linkage of the group.
5. A compound according to any one of claims 1 to 4, wherein the compound is selected from any one of compounds A to D:
6. an electron transport material comprising the compound according to any one of claims 1 to 5.
7. Use of the electron transport material according to claim 6 in an organic electroluminescent device.
8. An organic electroluminescent device comprising an anode, a cathode and an organic functional layer located between the anode and the cathode, wherein an electron transport layer of the organic functional layer comprises a compound according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 8, wherein the compound is used as a host material in an electron transport layer.
10. The organic electroluminescent device according to claim 8 or 9, wherein the organic functional layer further comprises any one or a combination of at least two of a light-emitting layer, an electron blocking layer, an electron injection layer, a hole blocking layer, or a hole transport layer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010898673.9A CN114105954A (en) | 2020-08-31 | 2020-08-31 | Compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010898673.9A CN114105954A (en) | 2020-08-31 | 2020-08-31 | Compound and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114105954A true CN114105954A (en) | 2022-03-01 |
Family
ID=80359924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010898673.9A Withdrawn CN114105954A (en) | 2020-08-31 | 2020-08-31 | Compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114105954A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115677767A (en) * | 2022-10-26 | 2023-02-03 | 京东方科技集团股份有限公司 | Organic electron transport material and organic electroluminescent device |
-
2020
- 2020-08-31 CN CN202010898673.9A patent/CN114105954A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115677767A (en) * | 2022-10-26 | 2023-02-03 | 京东方科技集团股份有限公司 | Organic electron transport material and organic electroluminescent device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111808042B (en) | Triarylamine compound and organic electroluminescent device thereof | |
| KR100940938B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2022205592A1 (en) | Benzothiophene benzo five-membered heterocycle material, preparation method therefor, and application thereof | |
| KR20220167774A (en) | Triarylamine derivative and organic electroluminescent device thereof | |
| CN114478499A (en) | Spirofluorene anthracene compound and application thereof | |
| CN114989069A (en) | Nitrogen-containing compound, electronic component, and electronic device | |
| CN110526900B (en) | Organic electroluminescent material and device | |
| CN114105954A (en) | Compound and application thereof | |
| CN110835346A (en) | Organic electroluminescent material and preparation method and application thereof | |
| CN115368370A (en) | Condensed nitrogen heterocyclic compound, application thereof and organic electroluminescent device containing compound | |
| CN114014851B (en) | Fluorene azole structural compound and application thereof | |
| CN114106003B (en) | Compound and application thereof | |
| CN109928961B (en) | Photoelectric material containing 4-sulfosulfonyl aryl dibenzofuran and application thereof | |
| CN112574254A (en) | Compound for organic luminescence and application thereof | |
| CN114133392A (en) | Compound and application thereof | |
| CN113387917B (en) | Organic compound containing spirofluorene derivative, organic electroluminescent device and display panel | |
| KR20210017428A (en) | Multicyclic compound and organic light emitting device comprising same | |
| CN113631546B (en) | Anthracene compound and organic light emitting device including the same | |
| CN111116658A (en) | Organic light-emitting material and OLED device comprising same | |
| CN114497424B (en) | Organic electroluminescent device and electronic device including the same | |
| CN115010701B (en) | Preparation method of nitrogen-containing heterocyclic derivative | |
| CN114437086B (en) | Dicarbazole compound and preparation method and application thereof | |
| CN113582986B (en) | Spiro compound, preparation method thereof, luminescent auxiliary material and organic electroluminescent device | |
| CN115490659B (en) | Nitrogen-containing compound, organic electroluminescent device and electronic device | |
| CN114805319B (en) | Compound taking triazine derivative as core and organic electroluminescent device comprising same |
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 | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20220301 |