CN114656475A - Organic electroluminescent material, luminescent device and luminescent device - Google Patents
Organic electroluminescent material, luminescent device and luminescent device Download PDFInfo
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Abstract
The organic electroluminescent material provided by the invention has a rigid ring structure consisting of a multi-membered ring, a carbazole ring and a furan ring, phenanthrene and naphthalene increase molecular conjugation, so that the intermolecular charge transition capability is facilitated, meanwhile, a substituent group with triarylamine and the like is connected to the R position of a compound structural formula, the molecular weight is increased, the molecules are not easy to crystallize and aggregate, and the material has higher photo-thermal stability. Therefore, using the organic electroluminescent compounds according to the present invention as a host in the light-emitting layer, the efficiency and lifetime of the resulting light-emitting device are significantly improved as compared to conventional organic electroluminescent compounds. In particular, the organic electroluminescent material of the present invention shows properties more suitable for the current high resolution demand trend by maintaining high efficiency at high luminance and having significantly improved lifetime.
Description
Technical Field
The invention belongs to the technical field of materials, and particularly relates to an organic electroluminescent material, a light-emitting device and a light-emitting device.
Background
The organic electroluminescent device has the characteristics of self-luminescence, wide viewing angle, high contrast, short response time, low driving voltage and the like, can realize a full-color OLED display through three organic electroluminescent materials (red, green and blue), is a latest generation flat panel display technology, can be used for a flat panel display and an illumination light source, and is put into the market in batches at present. Illumination sources will also be industrialized due to their own absolute advantages. The electroluminescent device has an all-solid-state structure, and the organic electroluminescent material is the core and the foundation of the device. The development of new materials is a source power for promoting continuous progress of an electroluminescence technology, and the original material preparation and device optimization are also research hotspots of the current organic electroluminescence industry.
Therefore, the need to provide organic electroluminescent materials with long service life and low cost is a problem to be solved by those skilled in the art.
Disclosure of Invention
The invention provides an organic electroluminescent material, aiming at solving the problems of short service life and low efficiency of the existing organic electroluminescent material.
The invention is realized by the following steps of preparing an organic electroluminescent material, wherein the structure of the organic electroluminescent material is as follows:
wherein R is a single substituent, and R represents any one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group;
R1-R5is a mono-substituent or a polysubstituent, each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 4-12-membered aromatic heterocyclic group, substituted or unsubstituted C8-C16 condensed ring group.
The invention also provides a light-emitting device which comprises the organic electroluminescent material.
The invention also provides a light-emitting device which comprises the organic electroluminescent material or the light-emitting device.
The organic electroluminescent material provided by the invention has a rigid ring structure consisting of a multi-membered ring, a carbazole ring and a furan ring, phenanthrene and naphthalene increase molecular conjugation, so that intermolecular charge transition capacity is facilitated, and meanwhile, a substituent group with triarylamine and the like is connected to the R position in the compound structural formula, so that the molecular weight is increased, intermolecular crystallization and aggregation are not easy, and the material has high photo-thermal stability. Therefore, using the organic electroluminescent compound of the present invention as a host in the light-emitting layer, the efficiency and lifetime of the resulting light-emitting device are significantly improved as compared to conventional organic electroluminescent compounds. In particular, the organic electroluminescent material of the present invention shows properties more suitable for the current high resolution demand trend by maintaining high efficiency at high luminance and having a remarkably improved lifetime.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The invention provides an organic electroluminescent material, which comprises the following chemical formula:
wherein R is a single substituent, and R represents any one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group;
R1-R5is a mono-or polysubstituent; each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 4-12 membered aromatic heterocyclic group, substituted or unsubstituted C8-C16 condensed ring group;
wherein the alkyl is a straight-chain alkyl, a branched-chain alkyl, a cyclic alkyl, a straight-chain alkyl substituted by at least 1 substituent, a branched-chain alkyl substituted by at least 1 substituent, or a cyclic alkyl substituted by at least 1 substituent; wherein, the substituent is one or more of halogen, deuterium, cyano and hydroxyl independently.
The aryl group is preferably an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein, the substituent groups are independently selected from halogen, tritium, amino, cyano, nitro and hydroxyl;
the heteroaromatic heterocyclic group is preferably an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro and hydroxyl;
R1-R5the substitution position is any position of the ring;
R1-R5can independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocyclic ring, a substituted or unsubstituted C5-C60 spiro ring with other substituents on the ring; r1-R4Substituted or unsubstituted C3-C30 aliphatic ring, substituted or unsubstituted C6-C60 aromatic ring, substituted or unsubstituted C2-C60 aromatic heterocycle, substituted or unsubstituted C5-C60 spiro ring; the substituents on the aliphatic ring, the aromatic heterocyclic ring and the spiro ring are at least selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group and substituted or unsubstituted C5-C60 spiro ringOne kind of the material is selected;
the heteroaromatic ring contains at least one heteroatom selected from B, N, O, S, Si and P.
Preferably, R represents any one of the groups shown in the following structural formula, but is not limited to the following structure.
Further, the organic electroluminescent material is selected from any one of the compounds shown in the following structural formula (including but not limited to the compounds shown in the following);
some specific structural forms are listed above, but the series of compounds are not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of the groups and the substitution positions thereof, which is not described in detail herein.
The organic electroluminescent material of the present invention can be prepared by synthetic methods known to those skilled in the art. Alternatively, the following reaction scheme is preferred for the preparation.
Wherein X is halogen.
The invention provides a method for preparing an organic luminescent material, which also comprises a method for synthesizing a raw material A, and comprises the following specific steps:
the invention provides a luminescent device, which is prepared by the organic electroluminescent material;
preferably, the light-emitting device comprises an anode, a cathode and at least one organic layer arranged between the anode and the cathode, wherein the organic layer is prepared from the organic electroluminescent material;
preferably, the organic layer includes a light emitting layer; wherein, the raw materials for forming the luminescent layer comprise doping materials and the organic electroluminescent materials;
preferably, the mass ratio of the organic electroluminescent material to the doping material is (90-99.5): (0.5-10);
preferably, the organic layer further includes a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
The present invention is not limited to the method for manufacturing the light emitting device, and any conventional method in the art may be used, and the present invention preferably forms an anode by depositing metal, conductive oxide, or an alloy thereof on a substrate by using a method such as thin film evaporation, electron beam evaporation, or physical vapor deposition, and then forms an organic layer and a cathode thereon to obtain the light emitting device.
The invention also provides a light-emitting device which comprises the light-emitting device.
Specifically, the above light emitting device may be applied to an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), an electronic paper (e-paper), an Organic Photoreceptor (OPC), an Organic Thin Film Transistor (OTFT), or the like.
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In addition, it should be noted that the numerical values given in the following examples are as precise as possible, but those skilled in the art will understand that each numerical value should be understood as a divisor rather than an absolutely exact numerical value due to measurement errors and experimental operational problems that cannot be avoided.
The synthesis of starting material A used in examples 1-18 is shown below:
intermediate A-1 synthesis:
dissolving 2-fluoro-7-nitronaphthalene (19.1g, 100mmol) in 200mL dichloromethane, dropwise adding liquid bromine (47.9g, 300mmol) under illumination, reacting at normal temperature for 48h, separating aqueous phase with alkaline water, extracting aqueous phase with dichloromethane, combining organic phases, concentrating to obtain solid, separating by column chromatography, and purifying by column chromatography to obtain a solid compound 12.15g, wherein the yield is 45%.
Synthesis of an intermediate A-2:
a-1(27g, 100mmol), potassium carbonate (27.6g, 200mmol), palladium acetate (0.23g, 1mmol) and 150g of 1-butyl-3-methylimidazolium tetrafluoroborate were charged into a 500mL reaction flask, and nitrogen gas was blown through the bottom insert for 10 minutes under magnetic stirring. B- (3-hydroxy-4-phenanthrene) phenylboronic acid (47.6g, 200mmol) was added and the surface purged with nitrogen for 10 minutes. And putting the reaction bottle into an oil bath kettle, heating to 40 ℃, and stirring for 2 hours under heat preservation. Further heating to 150 ℃, and stirring for 5 hours under the condition of heat preservation. The heating was stopped and the temperature was returned to room temperature with stirring.
The reaction solution is directly filtered, the solid is added with water to wash 80g multiplied by 2, then 100mL of ethanol is added to be heated until refluxing and hot beating is carried out for 0.5h, then the heating is stopped, and the reaction solution is returned to the room temperature under the state of magnetic stirring. Suction filtration is carried out, and the filter cake is rinsed by using 30ml of ethanol. Drying to obtain solid 15.9g, yield 44%.
Synthesis of an intermediate A-3:
a-2(36.3g, 100mmol), sodium chloride (97g, 1.65mol), aluminum chloride (247.3g, 1.85mol), and benzene (900mL) were stirred at 0 ℃ for 16 h. At the end of the reaction, water and NaHCO were used3The aqueous solution was washed to obtain 13g of a solid in a yield of 36%.
Synthesis of an intermediate A:
intermediate A-3(26.6g, 73.7mmol), triphenylphosphine (15.3g, 110.5mmol) and o-dichlorobenzene (250ml) were stirred under reflux for 24 h. After completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure, followed by extraction with CH2Cl 2. The extract was washed with MgSO4After drying, filtration and concentration, purification was performed by silica gel column chromatography to obtain intermediate a (16.4g, yield 68%).
Example 1: preparation of Compound a-5
A (16.4g, 50mmol), 2-bromonaphthalene (11.38g, 50mmol), and cesium carbonate (48.8g, 150mmol) were placed in a reaction system under nitrogen protection, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol), heated to 90 ℃, stirred uniformly, and reacted for 24 h. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate solid, so that 34.1g of light yellow solid is obtained, and the yield is 75%.
H-NMR(CDCl3)δ(ppm)＝8.14-8.17(1H)；δ(ppm)＝8.04-8.05(1H)；δ(ppm)＝7.94-7.96(1H)；δ(ppm)＝7.77-7.79(1H)；δ(ppm)＝7.71-7.73(2H)；δ(ppm)＝8.14-8.17(1H)；δ(ppm)＝7.64-7.68(1H)；δ(ppm)＝7.60-7.65(4H)；δ(ppm)＝7.51-7.56(1H)；δ(ppm)＝7.48-7.50(1H)；δ(ppm)＝7.42-7.46(2H)；δ(ppm)＝7.34-7.38(1H)。
Mass spectrum: calculated as 455.5; the test value was 455.7. Elemental analysis: calculated values are C: 89.65%; h: 3.76 percent; n: 3.07 percent; o: 3.51% test value C: 89.66 percent; h: 3.78 percent; n: 3.05 percent; o: 3.51 percent.
Example 2: preparation of Compound a-8
A (16.4g, 50mmol), 2-bromobenzo [9, 10] phenanthrene (16.88g, 55mmol) and cesium carbonate (48.8g, 150mmol) are placed in a reaction system under a nitrogen atmosphere, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol) are added to the reaction system, heated to 90 ℃, stirred uniformly and reacted for 24 h. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 1: 5) was used as a solvent, and the filtrate was concentrated to precipitate a solid, whereby 16.7g of a pale yellow solid was obtained in a yield of 60%.
Mass spectrum: calculated value 555.62; the test value was 555.78. Elemental analysis: calculated values are C: 90.79 percent; h: 3.81 percent; n: 2.52 percent; o: 2.88% test value C: 90.81 percent; h: 3.84 percent; n: 2.5 percent; o: 2.85 percent.
Example 3: preparation of Compound a-24
A (16.4g, 50mmol), 1-bromodibenzothiophene (14.46g, 55mmol) and cesium carbonate (48.8g, 150mmol) are placed into a reaction system under a nitrogen protection system, and then 300mL of dimethyl sulfoxide solution and 4-dimethylaminopyridine (0.3g, 2.5mmol) are added into the reaction system, heated to 90 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 1: 5) was used as a solvent, and the filtrate was concentrated to precipitate a solid, whereby 17.1g of a pale yellow solid compound was obtained in a yield of 67%.
Mass spectrum: calculated value 511.59; the test value was 511.78. Elemental analysis: the calculated values are C: 84.52 percent; h: 3.35 percent; n: 2.74 percent; o: 3.13 percent; s: 6.27% test value C: 84.5 percent; h: 3.37 percent; n: 2.7 percent; o: 3.15 percent; s: 6.29 percent.
Example 4: preparation of Compound a-28
A (16.4g, 50mmol), 1-bromodibenzofuran (13.58g, 55mmol), and cesium carbonate (48.8g, 150mmol) were placed in a reaction system under nitrogen atmosphere, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol), heated to 90 ℃, stirred, and reacted for 24 h. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate a solid, so that 14.3g of a light yellow solid compound is obtained, and the yield is 58%.
Mass spectrum: calculated value 495.53; the test value was 495.65. Elemental analysis: calculated values are C: 87.26%; h: 3.46 percent; n: 2.83 percent; o: 6.46% test values are C: 87.30 percent; h: 3.48 percent; n: 2.8 percent; o: 6.43 percent.
Example 5: preparation of Compound a-36
A (16.4g, 50mmol), (5r, 7r) -2 '-chlorospiro [ adamantane-2, 9' -fluorene ] (17.64g, 55mmol), and cesium carbonate (48.8g, 150mmol) were put into a reaction system, and then 300mL of a dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol) were added to the reaction system, heated to 90 ℃, stirred uniformly, and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, carrying out suction filtration after precipitation is separated out, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate solid, so that 10.9g of a light yellow solid compound is obtained, and the yield is 35.7%.
Mass spectrum: calculated value 613.74; the test value was 613.98. Elemental analysis: calculated values are C: 90.02 percent; h: 5.09%; n: 2.28 percent; o: 2.61% test value C: 90.22 percent; h: 5.04 percent; n: 2.08 percent; o: 2.66 percent.
Example 6: preparation of Compound a-42
A (16.4g, 50mmol), 4-bromo-9, 9-diphenylfluorene (21.78g, 55mmol), and cesium carbonate (48.8g, 150mmol) were put into a reaction system, followed by addition of 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol), heating to 90 ℃, stirring and reaction for 24 h. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate solid, so that 19.5g of a light yellow solid compound is obtained, and the yield is 60.5%.
Mass spectrum: calculated value 645.74; the test value was 645.89. Elemental analysis: calculated values are C: 91.14 percent; h: 4.21 percent; n: 2.17 percent; o: 2.48% test value C: 91.17 percent; h: 4.18 percent; n: 2.15 percent; o: 2.5 percent.
Example 7: preparation of Compound a-55
A (16.4g, 50mmol), 4-bromotriphenylamine (17.83g, 55mmol), and cesium carbonate (48.8g, 150mmol) were put into a reaction system, and then 300mL of a dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol) were added to the reaction system, heated to 90 ℃, stirred uniformly, and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, carrying out suction filtration after precipitation is separated out, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate solid, so that 18.7g of a light yellow solid compound is obtained, and the yield is 65.4%.
Mass spectrum: the calculated value is 572.65; the test value was 572.3. Elemental analysis: calculated values are C: 88.09 percent; h: 4.22 percent; n: 4.89%; o: 2.79% test value is C: 88.15 percent; h: 4.2 percent; n: 4.90 percent; o: 2.82 percent.
Example 8: preparation of Compound a-58
A (16.4g, 50mmol), N- (4-bromophenyl) -N, N-bis- (4-biphenyl) amine (26.2g, 55mmol), and cesium carbonate (48.8g, 150mmol) were put into a reaction system, followed by addition of 300mL of a dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol), heating to 90 ℃, stirring, and reaction for 24 h. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate solid, so that 21.9g of a light yellow solid compound is obtained, and the yield is 60.5%.
Mass spectrum: calculated value 724.84; the test value was 724.35. Elemental analysis: calculated values are C: 89.48 percent; h: 4.45 percent; n: 3.86 percent; o: 2.21% test value is C: 89.30 percent; h: 4.55 percent; n: 3.90 percent; o: 2.25 percent.
Example 9: preparation of Compound a-61
A (16.4g, 50mmol), 4-bromo-4' - (diphenylamino) biphenyl (22.0g, 55mmol), and cesium carbonate (48.8g, 150mmol) were placed in a reaction system, followed by addition of 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (0.3g, 2.5mmol), heating to 90 ℃, stirring, and reaction for 24 h. Cooling to room temperature of 25 ℃ after the reaction is stopped, carrying out suction filtration after precipitation is separated out, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether is 1: 5) is used as a solvent, and the filtrate is concentrated to precipitate a solid, so that 17.8g of a light yellow solid compound is obtained with the yield of 50%.
Mass spectrum: calculated value 648.75; the test value was 648.33. Elemental analysis: calculated values are C: 88.87%; h: 4.35 percent; n: 4.32 percent; o: 2.47% test value C: 88.70 percent; h: 4.40 percent; n: 4.37 percent; o: 2.52 percent.
The synthesis methods of other compounds are the same as those in the above embodiments, and are not repeated herein, and the test data of other embodiments are shown in table 1 below:
TABLE 1
| Examples | Compound (I) | Mass spectrometry | Elemental analysis |
| Example 10 | Compound a-12 | 531.65 | C：90.37；H：3.98；N：2.63；O：3.01 |
| Example 11 | Compound a-17 | 545.58 | C：88.06；H：3.51；N：2.57；O：5.87 |
| Example 12 | Compound a-31 | 571.66 | C：90.34；H：4.41；N：2.45；O：2.8 |
| Example 13 | Compound a-41 | 557.64 | C：90.46；H：4.16；N：2.51；O：2.87 |
| Example 14 | Chemical combinationObject a-44 | 570.64 | C：88.4；H：3.89；N：4.91；O：2.8 |
| Example 15 | Compound a-52 | 587.69 | C：85.84；H：3.6；N：2.38；O：2.72；S：5.46 |
| Example 16 | Compound a-54 | 571.62 | C：88.25；H：3.7；N：2.45；O：5.6 |
| Example 17 | Compound a-56 | 572.65 | C：88.09；H：4.22；N：4.89；O：2.79 |
| Example 18 | Compound a-62 | 648.75 | C：88.87；H：4.35；N：4.32；O：2.47 |
Device example 1
The embodiment provides an organic electroluminescent device, which comprises a first electrode, and a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer and a second electrode which are sequentially arranged on the first electrode. Wherein the first electrode is an ITO anode; the second electrode is a cathode; the light-emitting layer was prepared from the organic electroluminescent compound a-5 prepared in example 1 and the dopant material E.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
an ITO anode: coating with a thickness of
The ITO (indium tin oxide) glass substrate is cleaned in distilled water for 2 times, ultrasonically cleaned for 30min, then repeatedly cleaned for 2 times by distilled water, ultrasonically cleaned for 10min, and after the cleaning is finished, ultrasonically cleaned by methanol, acetone and isopropanol in sequence (each time for 5min), dried, and then transferred to a plasma cleaning machine for cleaning for 5min, so as to obtain the ITO anode.
HIL (hole injection layer): in the evaporator, 2-TNATA (N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine) is vacuum evaporated on the ITO anode
And forming a hole injection layer.
HTL (hole transport layer): then, NPB (i.e., N '-diphenyl-N, N' - (1-naphthyl) -1, 1 '-biphenyl-4, 4' -diamine) was vacuum-evaporated on the hole injection layer
A hole transport layer is formed.
EML (light-emitting layer): a mixed material of the host material and the dopant material E of the compound a-5 obtained in example 1 was vacuum-deposited as a light-emitting layer on the hole transport layer, wherein the weight ratio of the host material to the dopant material was 90: 10, and the thickness thereof was set to be 90: 10
Wherein the structural formula of the doping material E is as follows;
HBL (hole blocking layer): on the luminescent layerVacuum evaporation of bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BALq)
And forming a hole blocking layer.
ETL (electron transport layer): vacuum evaporation of 8-hydroxyquinoline aluminum (Alq3) onto the hole-blocking layer
An electron transport layer is formed.
EIL (electron injection layer): depositing LiF on the electron transport layer by vacuum evaporation
An electron injection layer is formed.
Cathode: vapor plating Al on the electron injection layer
And forming a cathode to obtain the organic electroluminescent device.
Referring to the organic electroluminescent device provided in device example 1 above and the method for manufacturing the same, organic electroluminescent compounds a-8, a-12, a-17, a-24, a-28, a-31, a-36, a-50, a-51, a-52, a-54, a-59, a-60, a-61, a-66, a-69, a-74, a-76, a-79, a-86, a-90, a-92, and a-103 were selected respectively to replace the organic electroluminescent compound a-5 provided in practical example 1, and evaporation of host materials was performed to prepare organic electroluminescent devices of the corresponding compounds, which were device examples 2 to 24 respectively.
Device comparative example 1: referring to the organic electroluminescent device and the method for manufacturing the same provided in device example 1, the organic electroluminescent compound a-5 was replaced with the host material RH-1, and evaporation of the host material was performed to prepare an organic electroluminescent device of a corresponding compound, which was comparative example 1. Wherein the structural formula of the main material RH-1 is as follows:
device comparative example 2: RH-1 was replaced with RH-2 in comparative example 1 above, and the other conditions were not changed. Wherein the structural formula of the main material RH-2 is as follows:
device comparative example 3: RH-1 was replaced with RH-3 in comparative example 1 above, and the other conditions were not changed. Wherein the structural formula of the main material RH-3 is as follows:
and (3) performance detection:
the organic electroluminescent devices obtained in practical examples 1 to 24 of the above-described devices and comparative examples 1 to 3 of the devices were characterized for driving voltage, luminous efficiency and lifetime at a luminance of 6000(nits), and the test results are shown in table 2 below.
TABLE 2
In summary, as can be seen from comparative example 1 and comparative example 3 in table 2, the benzofuran ring contained in the mother ring is higher than the benzothiophene ring contained in the mother ring in voltage, efficiency and lifetime, and then, compared with comparative example 1 and comparative example 2, the driving voltage of the organic electroluminescent devices provided in examples 1 to 18 of the device of the present invention is significantly lower than that of the comparative example, and the luminous efficiency and the device lifetime are higher than those of the comparative example, especially, the triarylamine group-containing compound is slightly higher than other groups in voltage, efficiency and lifetime. Therefore, compared with the organic electroluminescent devices prepared by using the comparative compounds RH-1, RH-2 and RH-3 as the luminescent layer materials, the organic electroluminescent devices prepared by using the organic electroluminescent compound provided by the invention as the luminescent layer materials have the advantages of reduced driving voltage, improved luminous efficiency and prolonged service life.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. An organic electroluminescent material, characterized in that the structure of the organic electroluminescent material is as follows:
wherein R is a single substituent, and R represents any one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group;
R1-R5is a single substituent or multiple substituents, and is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 4-12 membered aromatic heterocyclic group, and substituted or unsubstituted C8-C16 condensed ring group.
2. The organic electroluminescent material according to claim 1, wherein the alkyl group is a linear alkyl group, a branched alkyl group, a cyclic alkyl group, a linear alkyl group substituted with at least 1 substituent, a branched alkyl group substituted with at least 1 substituent, or a cyclic alkyl group substituted with at least 1 substituent;
wherein, the substituent is independently selected from one or more of halogen, deuterium, cyano-group and hydroxyl.
3. The organic electroluminescent material according to claim 1, wherein the aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent;
wherein, the substituent is one or more of halogen, deuterium, amino, cyano, nitro and hydroxyl.
4. The organic electroluminescent material according to claim 1, wherein the heteroaromatic heterocyclic group is an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent;
wherein the heteroatom in the heteroaryl group is one of nitrogen, sulfur or oxygen;
the substituent is independently selected from one or more of halogen, deuterium, amino, cyano, nitro and hydroxyl.
5. The organic electroluminescent material according to claim 1, wherein R is1-R5The substitution position is any position of the ring.
6. The organic electroluminescent material according to claim 1 or 5, wherein R is1-R5Can independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocyclic ring, a substituted or unsubstituted C5-C60 spiro ring with other substituents on the ring;
the R is1-R4Can be mutually substituted or notSubstituted C3-C30 aliphatic rings, substituted or unsubstituted C6-C60 aromatic rings, substituted or unsubstituted C2-C60 aromatic heterocycles, substituted or unsubstituted C5-C60 spirocycles;
the substituent on the aliphatic ring, the aromatic heterocyclic ring and the spiro ring is at least one selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group and substituted or unsubstituted C5-C60 spiro ring.
7. The organic electroluminescent material of claim 5, wherein the aromatic heterocycle contains at least one heteroatom selected from the group consisting of B, N, O, S, Si and P.
8. The organic electroluminescent material according to claim 1, wherein R represents any one of groups represented by the following structural formulae:
9. a light-emitting device characterized in that it comprises the organic electroluminescent material as claimed in any one of claims 1 to 8.
10. A light-emitting device comprising the organic electroluminescent material according to any one of claims 1 to 8 or the light-emitting device according to claim 9.
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| CN116836107A (en) * | 2023-07-05 | 2023-10-03 | 西安欧得光电材料有限公司 | Carbazol eight-membered ring large conjugated structure OLED material and preparation method thereof |
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| CN115160325A (en) * | 2022-07-14 | 2022-10-11 | 吉林奥来德光电材料股份有限公司 | Organic luminescent material and preparation method and application thereof |
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| CN109232596A (en) * | 2018-09-05 | 2019-01-18 | 大连九信精细化工有限公司 | A kind of synthetic method of dibenzofurans carbazole |
| CN115160325A (en) * | 2022-07-14 | 2022-10-11 | 吉林奥来德光电材料股份有限公司 | Organic luminescent material and preparation method and application thereof |
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| CN115160325A (en) * | 2022-07-14 | 2022-10-11 | 吉林奥来德光电材料股份有限公司 | Organic luminescent material and preparation method and application thereof |
| CN116836107A (en) * | 2023-07-05 | 2023-10-03 | 西安欧得光电材料有限公司 | Carbazol eight-membered ring large conjugated structure OLED material and preparation method thereof |
| CN116836107B (en) * | 2023-07-05 | 2024-02-27 | 西安欧得光电材料有限公司 | Carbazol eight-membered ring large conjugated structure OLED material and preparation method thereof |
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