CN115160325A - Organic luminescent material and preparation method and application thereof - Google Patents

Organic luminescent material and preparation method and application thereof Download PDF

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CN115160325A
CN115160325A CN202210833166.6A CN202210833166A CN115160325A CN 115160325 A CN115160325 A CN 115160325A CN 202210833166 A CN202210833166 A CN 202210833166A CN 115160325 A CN115160325 A CN 115160325A
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王辉
陈剑锋
李成录
李洪志
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses an organic luminescent material, a preparation method and application thereof, belonging to the field of organic photoelectric materials, wherein the molecular structure general formula is represented by a formula a:
Figure DDA0003746349010000011
wherein, in the formula a, R is a single substituent, and R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group or the like; r 1 、R 2 、R 3 、R 4 And R 5 Is a mono-or polysubstituent; each independently selected from hydrogen, deuterium, halogenCyano, substituted or unsubstituted C1-C6 alkyl, and the like. The present invention uses the organic light emitting material of the present invention as a host in a light emitting layer, and the efficiency and lifetime of an organic electroluminescent device are significantly improved as compared to conventional organic light emitting materials.

Description

Organic luminescent material and preparation method and application thereof
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to an organic luminescent material, and a preparation method and application thereof.
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 on the market in batch at present. Illumination sources will also be industrialized due to their absolute advantages. Electroluminescent devices have an all-solid-state structure, and organic electroluminescent materials are the core and foundation of the device. The development of new materials is a source for promoting the continuous progress of the electroluminescent technology, and the preparation of the original materials and the optimization of devices are also research hotspots of the current organic electroluminescent industry.
Therefore, the problem to be solved by those skilled in the art is to provide organic light emitting materials with long service life and low cost.
Disclosure of Invention
In view of the above, the present invention provides an organic light emitting material to solve the above problems in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic light emitting material having a molecular structural formula represented by formula a:
Figure BDA0003746346000000011
wherein, in the formula a, R is a single substituent, and R represents any one of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
R 1 、R 2 、R 3 、R 4 and R 5 Is a mono-or polysubstituted radical(ii) a Each independently 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, substituted or unsubstituted C8-C16 fused ring group.
Preferably, the alkyl group is selected from the group consisting of a straight-chain alkyl group, a branched-chain alkyl group, a cyclic alkyl group, a straight-chain alkyl group substituted with 1 or several substituents, a branched-chain alkyl group substituted with 1 or several substituents, and a cyclic alkyl group substituted with 1 or several substituents; wherein the substituents are independently selected from halogen, deuterium, cyano, hydroxy.
Preferably, the aryl group is selected from unsubstituted aryl groups, aryl groups substituted with 1 or several substituents; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy.
Preferably, the aromatic heterocyclic group is selected from the group consisting of an unsubstituted heteroaryl group, an aromatic heterocyclic group substituted with 1 or several substituents; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxyl.
Preferably, said R is 1 、R 2 、R 3 、R 4 And R 5 The substitution position is any position of the ring.
Preferably, said R is 1 、R 2 、R 3 、R 4 And R 5 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 heterocycle, a substituted or unsubstituted C5-C60 spiro ring with other substituents on the ring; r 1 、R 2 、R 3 、R 4 Can mutually form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle, a substituted or unsubstituted C5-C60 spiro ring; the substituent on the aliphatic ring, the aromatic heterocyclic ring and the spiro ring is 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 one of substituted or unsubstituted C5-C60 spiro ringOne or more of the above-mentioned raw materials; the aromatic heterocyclic ring contains one or more heteroatoms selected from B, N, O, S, si and P.
Preferably, R includes, but is not limited to, a group represented by the following structural formula:
Figure BDA0003746346000000031
Figure BDA0003746346000000041
preferably, the specific structural formula of the organic light-emitting material can also be represented by the following structure:
Figure BDA0003746346000000042
Figure BDA0003746346000000051
Figure BDA0003746346000000061
Figure BDA0003746346000000071
Figure BDA0003746346000000081
Figure BDA0003746346000000091
Figure BDA0003746346000000101
a method for preparing an organic luminescent material, the synthetic route for preparing the compound of formula a is as follows:
Figure BDA0003746346000000102
Figure BDA0003746346000000111
wherein X is halogen.
The organic electroluminescent device comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and the raw material of the light-emitting layer comprises a doping material and the organic light-emitting material.
Preferably, the mass ratio of the organic luminescent 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.
According to the technical scheme, compared with the prior art, the invention has the following beneficial effects:
the organic luminescent 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, and meanwhile, a substituent is connected to the R position in the compound structural formula, so that the molecular weight is increased, the intermolecular crystallization and aggregation are not easy, and the material has high photo-thermal stability. Therefore, using the organic light emitting material of the present invention as a host in the light emitting layer, the efficiency and lifetime of the organic electroluminescent device are significantly improved compared to conventional organic light emitting materials. In particular, the organic light emitting material of the present disclosure shows properties more suitable for the current high resolution demand trend by maintaining high efficiency at high luminance and having a significantly improved lifetime.
Detailed Description
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.
Preparation of intermediate a:
Figure BDA0003746346000000121
under the protection of nitrogen, 1-bromo-7-nitronaphthalene (25g, 99.18mmol), aniline (4.62g, 49.59mmol), sodium tert-butoxide (198.36mmol, 19.06g) are weighed and put into a reaction system, 500ml of toluene is added, and catalyst Pd is protected under nitrogen 2 (dba) 3 (1.98mmol, 1.14g) and (50%) P (t-Bu) 3 (3.97mmol, 0.8g), reflux at 110 ℃ for 22h under nitrogen, then cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g silica gel, spinning the organic phase filtrate to no liquid outflow, dissolving with 100ml dichloromethane, column chromatography (200-300 mesh, 800 g) of the solution with DCM: PE =1:1, spinning the receiver to no liquid outflow, and spin-drying to give the indicated compound a-1 (14.1 g, 53.79% yield).
Figure BDA0003746346000000122
Under the protection of nitrogen, A-1 (14g, 52.97mmol), 1-iodo-8-bromonaphthalene (38.8g, 116.54mmol) sodium tert-butoxide (105.95mmol, 10.18g) are weighed and put into a reaction system, 300ml toluene is added, and a catalyst Pd is added under the protection of nitrogen 2 (dba) 3 (1.06mmol, 0.6 g) and (50%) P (t-Bu) 3 (2.12mmol, 0.42g), reaction at 70 deg.C for 22h under nitrogen, cooling to 25 deg.C, passing the organic phase through a silica gel funnel of 100g silica gel, spinning the organic phase filtrate until no liquid flows out, and adding 100ml CH 2 Cl 2 Dissolving, carrying out column chromatography on the solution (200-300 meshes,600g) Developer DCM: PE =1:3, received liquid was spun down to no liquid outflow and spin dried to give the indicated compound a-2 (12.6 g, 50.68% yield).
Figure BDA0003746346000000123
A-2 (12g, 25.57mmol), sodium chloride (24.6g, 0.421mol), aluminum chloride (247.3g, 0.473mol), and benzene (360 ml) were stirred at 0 ℃ for 16h under a nitrogen blanket system. At the end of the reaction, water and NaHCO were used 3 The reaction mixture was washed with an aqueous solution to give compound A-3 as a solid (3.5 g, yield 35.61%).
Figure BDA0003746346000000131
Intermediate A-3 (35g, 91.05mmol), triphenylphosphine (35.82g, 136.58mmol) and o-dichlorobenzene (350 ml) were stirred under reflux for 24 hours. After the reaction is finished, cooling to normal temperature, removing the solvent by reduced pressure distillation, and using CH 2 Cl 2 And (4) extracting. The extract was extracted with MgSO 4 After drying, filtration and concentration, purification was performed by silica gel column chromatography to obtain intermediate a (16.4 g, yield 51.11%). Nuclear magnetic data: 1H-NMR (500MHz, chloroform-d) delta 8.33,8.31,8.22,8.20,8.20,7.81,7.80,7.79,7.67,7.67,7.66,7.66,7.65,7.65,7.65,7.65,7.54,7.53,7.51.
Example 1: preparation of Compound a-5
Figure BDA0003746346000000132
A (16.4 g, 46.54mmol), 2-bromonaphthalene (9.64g, 46.54mmol), and cesium carbonate (139.62mmol, 45.49g) were put into a reaction system under a nitrogen atmosphere, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g) 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, 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 = 1:5) was used as a solvent, and the filtrate was concentrated to precipitate a solid, which was 16.6g of a pale yellow solid, with a yield of 74.54%.
Mass spectrum: calculated as 478.14; the test value was 478.54. Elemental analysis: calculated values are C:90.35 percent; h:3.79 percent; n:5.85 percent; the test values are C:90.36%; h:3.78 percent; n:5.84 percent; nuclear magnetic data: 1H-NMR (500MHz, chloroform-d) delta 8.39,8.38,8.37,8.37,8.34,8.32,8.24,8.23,8.22,8.22,8.17,8.16,8.15,8.15,8.13,8.11,8.04,8.04,8.03,8.02,8.02,8.02,8.01,8.01,8.00,8.00,8.00,7.89,7.87,7.87,7.86,7.81,7.81,7.80,7.79,7.69,7.69,7.68,7.68,7.68,7.67,7.67,7.66,7.66,7.66,7.62,7.62,7.61,7.61,7.61,7.60,7.59,7.59,7.58,7.49,7.48,7.47,7.47,7.46,7.45.
Example 2: preparation of Compound a-8
Figure BDA0003746346000000141
A (16.4g, 46.54mmol), 2-bromobenzo [9,10] phenanthrene (14.3g, 46.54mmol), and cesium carbonate (139.62mmol, 45.49g) were put into a reaction system under a nitrogen atmosphere, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g) 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, 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 = 1:5) was used as a solvent, and the filtrate was concentrated to precipitate a solid, which was 16.2g of a pale yellow solid with a yield of 60%.
Mass spectrum: calculated as 578.17; the test value was 578.65. Elemental analysis: the calculated values are C:91.33%; h:3.83 percent; n:4.84 percent; the test value is C:91.34%; h:3.83; n:4.83 percent.
Example 3: preparation of Compound a-24
Figure BDA0003746346000000142
A (16.4 g, 46.54mmol), 1-bromodibenzothiophene (12.25g, 46.54mmol), and cesium carbonate (139.62mmol, 45.49g) were put into a reaction system under a nitrogen atmosphere, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g) 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, 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) is used as a solvent, and the filtrate is concentrated to precipitate a solid, so that 15.8g of a light yellow solid compound is obtained, and the yield is 63.5%.
Mass spectrum: calculated as 534.11; the test value was 534.62. Elemental analysis: calculated values are C:85.37%; h:3.39 percent; n:5.24 percent; s:6.00 percent; the test value is C:85.38%; h:3.38 percent; n:5.26 percent; s:6.01 percent.
Example 4: preparation of Compound a-28
Figure BDA0003746346000000151
A (16.4 g, 46.54mmol), 1-bromodibenzofuran (11.5g, 46.54mmol), and cesium carbonate (139.62mmol, 45.49g) were placed in a reaction system under a nitrogen atmosphere, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g) 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, 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) is used as a solvent, and the filtrate is concentrated to precipitate a solid, so that 14.2g of a light yellow solid compound is obtained, and the yield is 58.84%.
Mass spectrum: calculated as 518.14; the test value was 518.56. Elemental analysis: calculated values are C:88.01 percent; h:3.5 percent; n:5.40 percent; o:3.09% test value is C:88.02 percent; h:3.49 percent; n:5.40 percent; o:3.08 percent.
Example 5: preparation of Compound a-36
Figure BDA0003746346000000161
A (16.4g, 46.54mmol), (5r, 7r) -2 '-chlorospiro [ adamantane-2,9' -fluorene ] (14.93g, 46.54mmol), and cesium carbonate (139mmol, 45.49g) were put into a reaction system, and then 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g) 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, 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 = 1:5) is used as a solvent, and the filtrate is concentrated and solid is separated out to obtain 11.2g of a light yellow solid compound with the yield of 37.79%.
Mass spectrum: calculated as 636.25; the test value was 636.78. Elemental analysis: calculated values are C:90.54%; h:5.07 percent; n:4.40 percent; the test value is C:90.53 percent; h:5.08 percent; n:4.40 percent.
Example 6: preparation of Compound a-47
Figure BDA0003746346000000162
A (16.4 g, 46.54mmol), 2- (2-bromophenyl) -4,6-diphenyl-1,3,5-triazine (18.07g, 46.54mmol), and cesium carbonate (139.62mmol, 45.49g) were put into a reaction system, followed by addition of 300mL of a dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284 g), heating to 90 ℃, stirring uniformly, and reacting for 24h. 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. Using dichloromethane and petroleum ether mixed solution (V dichloromethane: V petroleum ether = 1:5) as solvent, concentrating the filtrate to precipitate solid, obtaining light yellow solid compound 16.4g, yield 53.41%
Mass spectrum: calculated as 659.21; the test value was 659.73. Elemental analysis: calculated values are C:85.57 percent; h:3.82 percent; n:10.62 percent; the test values are C:85.58 percent; h:3.83 percent; n:3.81 percent.
Example 7: preparation of Compound a-50
Figure BDA0003746346000000171
A (16.4 g, 4.54mmol), 4-bromo-9,9-diphenylfluorene (18.49g, 46.54mmol), and cesium carbonate (139mmol, 45.49g) were put into the reaction system, followed by addition of 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g), heating to 90 ℃, stirring uniformly, and reacting for 24h. 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. Using mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) as solvent, concentrating the filtrate to separate out solid to obtain light yellow solid compound 18.8g with yield 60.4%
Mass spectrum: calculated as 668.22; the test value was 668.78. Elemental analysis: calculated values are C:91.59%; h:4.22 percent; n:4.19 percent; the test value is C:91.58%; h:4.23 percent; n:4.19 percent.
Example 8: preparation of Compound a-51
Figure BDA0003746346000000181
A (16.4g, 46.54mmol), 4-bromo-9,9-spirobifluorene (18.4g, 46.54mmol), and cesium carbonate (139mmol, 45.49g) were put into the reaction system, followed by addition of 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g), heating to 90 ℃, stirring uniformly, and reacting 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. Using mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) as solvent, concentrating the filtrate to separate out solid to obtain light yellow solid compound 19.6g, yield 63.16%
Mass spectrum: calculated as 666.2; the test value was 666.2. Elemental analysis: calculated values are C:91.87 percent; h:3.93 percent; n:4.20 percent; the test value is C:91.88%; h:3.94 percent; n:4.30 percent.
Example 9: preparation of Compound a-59
Figure BDA0003746346000000182
A (16.4 g, 46.54mmol), deuterated bromobenzene (7.54g, 46.54mmol), and cesium carbonate (139.62mmol, 45.49g) were put into the reaction system, followed by addition of 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g), heating at 90 ℃, stirring and reacting for 24h. 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. Using mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) as solvent, concentrating the filtrate to separate out solid to obtain light yellow solid compound 15.2g with yield of 75.34%
Mass spectrum: calculated as 433.16; the test value was 433.51. Elemental analysis: calculated values are C:88.66 percent; h:4.88 percent; n:6.46 percent; the test value is C:88.67 percent; h:4.89%; n:6.45 percent;
example 10: preparation of Compound a-60
Figure BDA0003746346000000191
A (16.4 g, 46.54mmol), 1-phenyl-7-bromodibenzofuran (15.04g, 46.54mmol), and cesium carbonate (139mmol, 45.49g) were put into the reaction system, followed by addition of 300mL of dimethyl sulfoxide solution, 4-dimethylaminopyridine (2.33mmol, 0.284g), heating to 90 ℃, stirring and reaction for 24h. 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. Using mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) as solvent, concentrating the filtrate to separate out solid to obtain light yellow solid compound 19.6g, yield 70.82%
Mass spectrum: calculated as 594.17; the test value was 594.65. Elemental analysis: the calculated values are C:88.87%; h:3.73 percent; n:4.71 percent; o:2.69% test value C:88.87%; h:3.74 percent; n:4.70 percent; o:2.70 percent.
Other examples test data are shown in table 1:
TABLE 1
Figure BDA0003746346000000192
Figure BDA0003746346000000201
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 by using 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
Figure BDA0003746346000000202
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 5 min), 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 (namely N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) is evaporated on an ITO anode in vacuum) Phenyl) -N1-phenylbenzene-1,4-diamine
Figure BDA0003746346000000211
And forming a hole injection layer.
HTL (hole transport layer): NPB (i.e., N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4,4' -diamine) is then vacuum evaporated on the hole injection layer
Figure BDA0003746346000000212
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-evaporated as a light-emitting layer on the hole transport layer, wherein the weight ratio of the host material to the dopant material was 90
Figure BDA0003746346000000213
Wherein the structural formula of the doping material E is as follows;
Figure BDA0003746346000000214
HBL (hole blocking layer): vacuum evaporating bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BALq) on the luminescent layer
Figure BDA0003746346000000215
And forming a hole blocking layer.
ETL (electron transport layer): vacuum deposition of 8-hydroxyquinoline aluminum (Alq 3) on the hole-blocking layer
Figure BDA0003746346000000216
An electron transport layer is formed.
EIL (electron injection layer): depositing LiF on the electron transport layer by vacuum evaporation
Figure BDA0003746346000000217
An electron injection layer is formed.
Cathode: on the electron injection layerDeposition of Al
Figure BDA0003746346000000218
And forming a cathode to obtain the organic electroluminescent device.
Referring to the organic light emitting material and the preparation method thereof provided in example 1, organic light emitting materials a-8, a-12, a-17, a-24, a-28, a-31, a-36, a-47, a-49, 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 light emitting material a-5 provided in practical example 1, and evaporation of a host material was performed to prepare organic electroluminescent devices of corresponding compounds, which are examples 2 to 26 respectively.
Comparative example 1: referring to the organic light emitting material and the method for preparing the same provided in example 1, the organic light emitting material a-5 was replaced with the host material RH, 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 is as follows:
Figure BDA0003746346000000221
performance detection
The organic electroluminescent devices obtained in practical examples 1 to 26 and comparative example 1 were characterized at a luminance of 6000 (nits) for driving voltage, luminous efficiency and lifetime, and the test results are shown in table 2:
TABLE 2
Figure BDA0003746346000000222
Figure BDA0003746346000000231
As can be seen from table 2, compared with comparative example 1, the driving voltage of the organic electroluminescent devices provided in practical examples 1 to 26 of the present invention is 3.2V to 3.6V, which is significantly lower than that of comparative example 1, while the luminous efficiency is much higher than that of comparative example 1, and the lifetime (490 to 580) is 8 to 10 times that of comparative example 1, and thus it can be seen that the organic electroluminescent devices prepared using the organic luminescent materials provided in the present invention as the luminescent layer material have significantly reduced driving voltage and significantly improved luminous efficiency and lifetime compared with the organic electroluminescent devices prepared using the comparative compound RH as the luminescent layer material.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other.
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 light-emitting material, characterized in that its molecular structural general formula is represented by formula a:
Figure FDA0003746345990000011
wherein, in the formula a, 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;
R 1 、R 2 、R 3 、R 4 and R 5 Is 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 C4-C12 aromatic heterocyclic group, substituted or unsubstituted C8-C16 fused ring group.
2. An organic light-emitting material according to claim 1, wherein the alkyl group is selected from a linear alkyl group, a branched alkyl group, a cyclic alkyl group, a linear alkyl group substituted with 1 or several substituents, a branched alkyl group substituted with 1 or several substituents, and a cyclic alkyl group substituted with 1 or several substituents; wherein the substituents are independently selected from halogen, deuterium, cyano, hydroxy.
3. An organic light-emitting material according to claim 1, wherein the aryl group is selected from an unsubstituted aryl group, an aryl group substituted with 1 or more substituents; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy.
4. The organic light-emitting material according to claim 1, wherein the aromatic heterocyclic group is selected from an unsubstituted heteroaryl group, an aromatic heterocyclic group substituted with 1 or several substituents; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxyl.
5. The organic light-emitting material of claim 1, wherein R is 1 、R 2 、R 3 、R 4 And R 5 Each independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-substituted benzene ring with each otherA C60 heteroaromatic ring, a substituted or unsubstituted C5-C60 spirocyclic ring; r is 1 、R 2 、R 3 、R 4 Can mutually form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle, a substituted or unsubstituted C5-C60 spiro ring; the substituent on the aliphatic ring, the aromatic heterocyclic ring and the spiro ring is selected from one or more of 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; the aromatic heterocyclic ring contains one or more heteroatoms selected from B, N, O, S, si and P.
6. The organic light-emitting material of claim 1, wherein R includes but is not limited to a group represented by the following structural formula:
Figure FDA0003746345990000031
Figure FDA0003746345990000041
7. a method for preparing the organic light emitting material as claimed in claim 1, wherein the synthesis route for preparing the compound of formula a is as follows:
Figure FDA0003746345990000051
wherein X is halogen.
8. Use of an organic light-emitting material in an organic electroluminescent device, wherein the organic electroluminescent device comprises an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and the raw material of the light-emitting layer comprises a doping material and the organic light-emitting material according to any one of claims 1 to 6.
9. The application of the organic luminescent material in the organic electroluminescent device is characterized in that the mass ratio of the organic luminescent material to the doping material is (90-99.5) to (0.5-10).
10. The application of the organic light-emitting material in the organic electroluminescent device is characterized in that the organic layer further comprises 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.
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CN114394928A (en) * 2022-01-12 2022-04-26 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN114656475A (en) * 2022-04-11 2022-06-24 吉林奥来德光电材料股份有限公司 Organic electroluminescent material, luminescent device and luminescent device

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* Cited by examiner, † Cited by third party
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CN114394928A (en) * 2022-01-12 2022-04-26 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN114656475A (en) * 2022-04-11 2022-06-24 吉林奥来德光电材料股份有限公司 Organic electroluminescent material, luminescent device and luminescent device

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