CN112521327A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN112521327A
CN112521327A CN202011497167.5A CN202011497167A CN112521327A CN 112521327 A CN112521327 A CN 112521327A CN 202011497167 A CN202011497167 A CN 202011497167A CN 112521327 A CN112521327 A CN 112521327A
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organic compound
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aromatic group
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梁现丽
刘阳
范洪涛
陈婷
杭德余
段陆萌
曹占广
班全志
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Abstract

The invention relates to the technical field of organic electroluminescent display, in particular to an organic compound and application thereof; the organic compound has a structure shown as a general formula (I); the novel OLED material provided by the invention takes an indolone heterocyclic structure compound as a matrix, and an electron-donating group is introduced into the matrix structure, so that the novel OLED material which has a high triplet state energy level, a good carrier mobility, high thermal stability and high film forming stability and can be matched with an adjacent energy level is obtained; the material can be applied to the field of organic electroluminescence, can be used as a green light main body material, and can effectively improve the photoelectric property of a device.

Description

Organic compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to an organic compound and application thereof.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has a wider application prospect.
Since OLEDs were first reported, many scholars have been working on how to improve device efficiency and stability. Forrest and Thompson research groups find that the transition metal complex can be applied to Ph OLEDs (phosphorescent OLEDs), the phosphorescent material has strong spin-orbit coupling effect, and singlet excitons and triplet excitons can be simultaneously utilized, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100%. However, phosphorescent materials have a longer excited state lifetime, and are prone to form triplet-triplet quenching and triplet-polaron- quenching when the triplet exciton concentration is higher. Phosphorescent materials are often incorporated as guest into host materials to reduce self-concentration quenching processes. Therefore, it is also an important matter to select a suitable host material in Phosphorescent organic electroluminescent devices (Ph OLEDs). Essential characteristics of the host material: (1) possesses a triplet energy level higher than that of the guest dye; (2) the carrier mobility is better and can be matched with the energy level of the adjacent layer; (3) has high thermal stability and film forming stability.
At present, OLED display and illumination are widely commercialized and applied, the requirements of a client terminal on the photoelectricity and service life of an OLED screen body are continuously improved, in order to meet the requirements, in addition to the refinement and refinement on the OLED panel manufacturing process, the development of OLED materials capable of meeting higher device indexes is very important. Therefore, a stable and efficient main body material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the method has important practical application value.
Disclosure of Invention
The invention aims to provide an OLED main body material which has higher triplet state energy level, better carrier mobility, higher thermal stability and film forming stability and can be matched with adjacent energy levels, and application of the organic material in an OLED device.
In order to develop the compound with the properties, the invention discovers a novel compound containing the heterocyclic structure of the indolone, which can be used for an organic electroluminescent device, through systematic quantitative theoretical calculation and intensive experimental research work; the parent nucleus of the series of compounds has an electron withdrawing effect, is connected with five-membered heterocyclic groups such as carbazole, furan, thiophene and the like with electron donating capacity, can be used as a green light main body material, has good thermal stability, can be well applied to OLED devices, is represented by a general formula (I), and can be applied to the OLED devices to achieve the purposes.
The first purpose of the invention is to provide an organic compound, which has a structure shown as a general formula (I):
Figure BDA0002842517600000021
wherein:
L1、L2each independently represents a single bond, substituted or unsubstituted C6～C30Arylene of (a), substituted or unsubstituted C3～C30The heterocyclylene aryl of (a);
R1、R2each independently represents a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring, and at least one group is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; r1、R2May be the same or different;
n is an integer of 1 to 8.
Preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle contains at least one five-membered heterocycle, preferably one, two or three five-membered heterocycles; the five-membered heterocyclic ring contains at least one heteroatom, preferably one, two or three heteroatoms; the heteroatom is optionally selected from the group consisting of N atoms, S atoms, and O atoms; when the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains a plurality of hetero atoms, the respective hetero atoms may be the same as each other, may be partially the same as each other, or may be different from each other.
Preferably, when the above groups are substituted, the substituents are selected from: halogenElement, deuterium atom, cyano group, C1～C10Alkyl or cycloalkyl of, C2～C6Alkenyl or cycloalkenyl of1～C6Alkoxy or thioalkoxy of C6～C30Arylene of, C3～C30The heteroaryl group of (a).
Preferably, L is1、L2Represents a single bond; the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from: substituted or unsubstituted carbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl; n is 1 or 2.
Preferably, in the substituted aromatic group containing a five-membered heterocyclic ring, the substituent used for substitution may be arbitrarily selected from: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, indolo (e.g., N-benzindolo), benzothieno, benzofuro; the number of the substituent groups is an integer of 1 to 5, preferably an integer of 1 to 3.
Preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002842517600000031
Figure BDA0002842517600000041
Figure BDA0002842517600000051
Figure BDA0002842517600000061
further, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002842517600000062
Figure BDA0002842517600000071
still further, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002842517600000072
Figure BDA0002842517600000081
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
Preferably, the general formula (I) is selected from the compounds represented by the following formulae I-1 to I-56:
Figure BDA0002842517600000082
Figure BDA0002842517600000091
Figure BDA0002842517600000101
Figure BDA0002842517600000111
the organic compound takes an indolone heterocyclic structure as a matrix, the matrix structure has good thermal stability and simultaneously has proper HOMO and LUMO energy levels and Eg, and a group with strong electron donating capability is introduced into an active position in the matrix structure, namely five-membered heterocyclic structures such as carbazole, furan, thiophene and the like with strong electron donating capability are introduced into the structure, so that a novel structure OLED material is obtained; the material is applied to an OLED device and used as a green light main body material, so that the photoelectric property of the device can be effectively improved; the device can be applied to the field of display or illumination.
The second purpose of the invention is to propose the application of the organic compound in an organic electroluminescent device;
preferably, the organic compound is used as a green host material of an electroluminescent layer in an organic electroluminescent device.
A third object of the present invention is to propose an organic electroluminescent device comprising an electroluminescent layer containing the organic compound.
Preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer containing the organic compound, an electron transport layer, an electron injection layer and a cathode layer from bottom to top in sequence;
furthermore, the thickness of the electroluminescent layer can be 10-50 nm, preferably 20-40 nm.
It is a fourth object of the present invention to provide a display apparatus including the organic electroluminescent device.
A fifth object of the present invention is to provide a lighting apparatus including the organic electroluminescent device.
The novel OLED material provided by the invention takes an indolone heterocyclic structure compound as a matrix, and an electron-donating group is introduced into the matrix structure, so that the novel OLED material which has a high triplet state energy level, a good carrier mobility, high thermal stability and high film forming stability and can be matched with an adjacent energy level is obtained; the material can be applied to the field of organic electroluminescence, can be used as a green light main body material, and can effectively improve the photoelectric property of a device.
Detailed Description
The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting a suitable catalyst and a suitable solvent, and determining a suitable reaction temperature, a suitable reaction time, a suitable material ratio, and the like, which are not particularly limited in the present invention. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
The synthesis method of the present invention is briefly described below.
(1) When R is1And R2Similarly, and when linked to the parent nucleus via a C-N bond, the synthetic route is as follows:
Figure BDA0002842517600000121
(2) when R is1And R2In contrast, and when linked to the parent nucleus via a C-N bond, the synthetic route is as follows:
Figure BDA0002842517600000131
(3) when R is1And R2Similarly, and when linked to the parent nucleus via a C-C bond, the synthetic route is as follows:
Figure BDA0002842517600000132
(4) when R is1And R2In contrast, and when linked to the parent nucleus via a C-C bond, the synthetic pathway is as follows (Cl and Br adjusted as required):
Figure BDA0002842517600000133
(5) when R is1And R2In contrast, when they are linked to the parent nucleus via C-C bond and C-N bond, respectively, the synthetic route is as follows (Cl and Br are adjusted as required):
Figure BDA0002842517600000134
EXAMPLE 1 Synthesis of Compound I-1
Figure BDA0002842517600000135
The synthetic route is as follows:
Figure BDA0002842517600000141
A2L three-necked flask is stirred by magnetic stirring, and after nitrogen replacement, sodium tert-butoxide (28.8g, 0.3mol), 9H-carbazole (33.4g, 0.2mol) and 400ml of toluene are added in sequence. After nitrogen replacement again, (0.8g, 4mmol) of tri-tert-butylphosphine and (0.5g, 2mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. And (3) beginning to dropwise add a solution consisting of (37.5g, 0.1mol) M1 and 100ml of toluene, controlling the temperature to be 80-120 ℃ and reacting for 4 hours, and finishing the reaction. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 54.1g pale yellow solid with yield of about 85%.
Product MS (m/e): 637.22, respectively; elemental analysis (C)46H27N3O): theoretical value C: 86.63%, H: 4.27%, N: 6.59 percent; found value C: 86.69%, H: 4.35%, N: 6.43 percent.
EXAMPLE 2 Synthesis of Compound I-14
Figure BDA0002842517600000142
The synthetic route is as follows:
Figure BDA0002842517600000151
into a 1L three-necked flask, M2(41.9g, 0.1mol), (9, 9-dimethyl-9H-fluoren-2-yl) boronic acid (23.8g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is evaporated off, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating mode, ethyl acetate is pulped, and filtration is carried out to obtain 45.8g of light yellow solid I-14-1 with the yield of about 86%.
A2L three-necked flask is stirred by magnetic stirring, and after nitrogen replacement, sodium tert-butoxide (14.4g, 0.15mol), 3, 6-diphenyl-9H-carbazole (31.9g, 0.1mol) and toluene 400ml are added in sequence. After nitrogen replacement again, (0.4g, 2mmol) of tri-tert-butylphosphine and (0.23g, 1mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. A solution consisting of (53.3g, 0.1mol) I-14-1 and 100ml toluene is added dropwise, the temperature is controlled between 80 ℃ and 120 ℃ to react for 4 hours, and the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 66.1g pale yellow solid with yield of about 81%.
Product MS (m/e): 816.31, respectively; elemental analysis (C)61H40N2O): theoretical value C: 89.68%, H: 4.94%, N: 3.43 percent; found value C: 89.75%, H: 4.98%, N: 3.30 percent.
EXAMPLE 3 Synthesis of Compound I-16
Figure BDA0002842517600000161
The synthetic route is as follows:
Figure BDA0002842517600000162
into a 1L three-necked flask, M3(34.3g, 0.1mol), (4'- (methyl-d 3) - [1,1' -biphenyl) was charged]-3-yl) boronic acid (21.5g, 0.1mol),Sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, water 150mL, the reaction system with nitrogen replacement protection, then added Pd (PPh)3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is evaporated, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating mode, the ethyl acetate is pulped, and 31.2g of light yellow solid I-16-1 is obtained after filtration, and the yield is about 72%.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium tert-butoxide (14.4g, 0.15mol), 7H-dibenzo [ c, g ] carbazole (26.7g, 0.1mol) and 400ml of toluene were added in this order. After nitrogen replacement again, (0.4g, 2mmol) of tri-tert-butylphosphine and (0.23g, 1mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. A solution consisting of (43.4g, 0.1mol) I-16-1 and 100ml toluene is added dropwise, the temperature is controlled between 80 ℃ and 120 ℃ to react for 4 hours, and the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 51.9g pale yellow solid with yield about 78%.
Product MS (m/e): 665.25, respectively; elemental analysis (C)49H27D3N2O): theoretical value C: 88.39%, H: 5.00%, N: 4.21 percent; found value C: 88.43%, H: 5.06%, N: 4.08 percent.
EXAMPLE 4 Synthesis of Compound I-18
Figure BDA0002842517600000171
The synthetic route is as follows:
Figure BDA0002842517600000172
m4(41.9g, 0.1mol), dibenzo [ b, d ] was charged into a 1L three-necked flask]Thiophen-3-ylboronic acid (22.8g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene (150 mL), ethanol (150 mL), and water (150 mL), and Pd (PPh) was added after the reaction system was purged with nitrogen3)4(11.5g, 10 mmol). Heating reflux reaction (in the system)The reaction was stopped at a temperature of about 78 ℃ for 3 hours. The solvent is evaporated off, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating way, the ethyl acetate is pulped, 46.0g of light yellow solid I-18-1 is obtained by filtration, and the yield is about 88%.
A2L three-necked flask is stirred by magnetic force, sodium tert-butoxide (14.4g, 0.15mol), 10H-phenanthrene [9,10-b ] carbazole (31.7g, 0.1mol) and toluene 400ml are added in sequence after nitrogen replacement. After nitrogen replacement again, (0.4g, 2mmol) of tri-tert-butylphosphine and (0.23g, 1mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. Beginning to dropwise add a solution consisting of (52.3g, 0.1mol) I-18-1 and 100ml of toluene, controlling the temperature to be 80-120 ℃ and reacting for 4 hours, and finishing the reaction. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 57.9g pale yellow solid with yield about 72%.
Product MS (m/e): 804.22, respectively; elemental analysis (C)58H32N2OS): theoretical value C: 86.54%, H: 4.01%, N: 3.48 percent; found value C: 86.59%, H: 4.06%, N: 3.36 percent.
EXAMPLE 5 Synthesis of Compound I-24
Figure BDA0002842517600000181
The synthetic route is as follows:
Figure BDA0002842517600000182
into a 1L three-necked flask, M5(49.6g, 0.1mol), 2-naphthylboronic acid (17.2g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. Distilling off solvent, extracting with dichloromethane, drying with anhydrous magnesium sulfate, filtering, performing petroleum ether/ethyl acetate (2:1) column chromatography, spin-drying solvent, pulping with ethyl acetate, filtering to obtain 41.3g pale yellow solid I-24-1,the yield thereof was found to be about 76%.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (14.4g, 0.15mol), 7H-benzofuran [2,3-b ] carbazole (25.7g, 0.1mol) and 400ml of toluene were added in this order. After nitrogen replacement again, (0.4g, 2mmol) of tri-tert-butylphosphine and (0.23g, 1mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. Beginning to dropwise add a solution consisting of (54.4g, 0.1mol) I-24-1 and 100ml of toluene, controlling the temperature to be 80-120 ℃ and reacting for 4 hours, and finishing the reaction. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 52.8g pale yellow solid with yield of about 69%.
Product MS (m/e): 765.24, respectively; elemental analysis (C)55H31N3O2): theoretical value C: 86.26%, H: 4.08%, N: 5.49 percent; found value C: 86.32%, H: 4.15%, N: 5.26 percent.
EXAMPLE 6 Synthesis of Compound I-27
Figure BDA0002842517600000191
The synthetic route is as follows:
Figure BDA0002842517600000192
A1L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, M6(37.5g, 0.1mol), (9-phenyl-9H-carbazol-3-yl) boronic acid (57.4g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml were sequentially added, followed by stirring. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) tris (dibenzylideneacetone) dipalladium were added. And after the addition is finished, heating, raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 61.5g of pale yellow solid with the yield of about 78%.
Product MS (m/e): 789.28, respectively; elemental analysis (C)58H35N3O): theoretical value C: 88.19%, H: 4.47%, N: 5.32 percent; found value C: 88.26 percent，H：4.54％，N：5.11％。
EXAMPLE 7 Synthesis of Compound I-35
Figure BDA0002842517600000201
The synthetic route is as follows:
Figure BDA0002842517600000202
m7(41.9g, 0.1mol), dibenzo [ b, d ] furan-3-ylboronic acid (21.2g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged in a 1L three-necked flask, and Pd (PPh3)4(11.5g, 10mmol) was added after the reaction system was purged with nitrogen. The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is evaporated off, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating mode, ethyl acetate is pulped, and filtration is carried out to obtain 35.5g of light yellow solid I-35-1 with the yield of about 70%.
A2L three-necked flask is stirred by magnetic stirring, and after nitrogen replacement, sodium tert-butoxide (14.4g, 0.15mol), 3, 6-diphenyl-9H-carbazole (31.9g, 0.1mol) and toluene 400ml are added in sequence. After nitrogen replacement again, (0.4g, 2mmol) of tri-tert-butylphosphine and (0.23g, 1mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. Beginning to dropwise add a solution consisting of (50.7g, 0.1mol) I-35-1 and 100ml of toluene, controlling the temperature to be 80-120 ℃ and reacting for 4 hours, and finishing the reaction. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 64.0g pale yellow solid with yield of about 81%.
Product MS (m/e): 790.26, respectively; elemental analysis (C)58H34N2O2): theoretical value C: 88.08%, H: 4.33%, N: 3.54 percent; found value C: 88.15%, H: 4.40%, N: 3.33 percent.
EXAMPLE 8 Synthesis of Compound I-43
Figure BDA0002842517600000211
The synthetic route is as follows:
Figure BDA0002842517600000212
A1L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, M1(37.5g, 0.1mol), (3-phenylbenzo [ b ] thiophen-2-yl) boronic acid (50.8g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml were added in this order, and stirring was started. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) tris (dibenzylideneacetone) dipalladium were added. And after the addition is finished, heating, raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 60.0g pale yellow solid with about 83% yield.
Product MS (m/e): 723.17, respectively; elemental analysis (C)50H29NOS2): theoretical value C: 82.96%, H: 4.04%, N: 1.93 percent; found value C: 82.90%, H: 4.10%, N: 1.85.
EXAMPLE 9 Synthesis of Compounds I-49
Figure BDA0002842517600000221
The synthetic route is as follows:
Figure BDA0002842517600000222
to a 1L three-necked flask, M8(46.9g, 0.1mol), dinaphtho [2, 1-b: 1', 2' -d]Furan-5-ylboronic acid (31.2g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL, the reaction system was purged with nitrogen and Pd (PPh) was added3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent was evaporated off, extracted with dichloromethane and dried over anhydrous magnesium sulfateFiltering, performing petroleum ether/ethyl acetate (2:1) column chromatography, spin-drying the solvent, pulping the ethyl acetate, and filtering to obtain 46.6g of a light yellow solid I-49-1 with the yield of about 71%.
A1L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, I-49-1(65.7g, 0.1mol), (9, 9-dimethyl-9H-fluoren-2-yl) boronic acid (23.8g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane 400ml were added in this order, followed by stirring. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. And after the addition is finished, heating, raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 65.2g of pale yellow solid with the yield of about 80%.
Product MS (m/e): 815.28, respectively; elemental analysis (C)61H37NO2): theoretical value C: 89.79%, H: 4.57%, N: 1.72 percent; found value C: 89.79%, H: 4.57%, N: 1.72 percent.
EXAMPLE 10 Synthesis of Compound I-54
Figure BDA0002842517600000231
The synthetic route is as follows:
Figure BDA0002842517600000241
into a 1L three-necked flask, M9(46.9g, 0.1mol), (9-phenyl-9H-carbazol-3-yl) boronic acid (28.7g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and Pd (PPh) was added after the reaction system was protected by nitrogen substitution3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is evaporated, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating mode, the ethyl acetate is pulped, and filtration is carried out to obtain 41.1g of light yellow solid I-54-1 with the yield of about 65%.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (14.4g, 0.15mol), 7H-benzofuran [2,3-b ] carbazole (25.7g, 0.1mol) and 400ml of toluene were added in this order. After nitrogen replacement again, (0.4g, 2mmol) of tri-tert-butylphosphine and (0.23g, 1mmol) of palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. Beginning to dropwise add a solution consisting of (63.2g, 0.1mol) I-54-1 and 100ml of toluene, controlling the temperature to be 80-120 ℃ and reacting for 4 hours, and finishing the reaction. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 60.6g pale yellow solid with yield about 71%.
Product MS (m/e): 853.27, respectively; elemental analysis (C)62H35N3O2): theoretical value C: 87.20%, H: 4.13%, N: 4.92 percent; found value C: 87.25%, H: 4.16%, N: 4.79 percent.
According to the technical schemes of the examples 1 to 10, other compounds I-1 to I-56 can be synthesized by simply replacing corresponding raw materials without changing any substantial operation.
Device examples the compounds of the invention were used as green host materials
The embodiment provides a group of OLED green light devices OLED-1, and the structures of the devices are as follows:
ITO/HATCN (1nm)/HT01(40nm)/NPB (20nm)/EML (30nm) (containing I-1)/Bphen (40nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
Figure BDA0002842517600000251
(1) ultrasonically cleaning a glass substrate coated with an ITO transparent conductive film in cleaning solution, ultrasonically treating the glass substrate in deionized water, ultrasonically removing oil in a mixed solution of acetone and ethanol (the volume ratio is 1: 1), baking the glass substrate in a clean environment until the water is completely removed, carrying out etching and ozone treatment by using an ultraviolet lamp, and bombarding the surface by using low-energy cation beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa on the anode layer filmCarrying out vacuum evaporation on HATCN serving as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm; then evaporating a hole transport layer NPB with the evaporation rate of 0.1nm/s and the evaporation film thickness of 20 nm;
(3) EML is vacuum evaporated on the hole transport layer to be used as a light emitting layer of the device, the EML comprises the green light host material (I-1) and the dye material, the host material used as the light emitting layer is placed in a chamber of vacuum vapor deposition equipment by utilizing a multi-source co-evaporation method, and Ir (ppy) used as a dopant3Placing in another chamber of vacuum vapor deposition equipment, and adjusting evaporation rate of main material to 0.1nm/s, Ir (ppy)3The concentration of (2) is 10%, and the total film thickness of evaporation plating is 30 nm;
(4) evaporating Bphen on the luminescent layer in vacuum to form an electron transport layer with the thickness of 40nm, wherein the evaporation rate is 0.1 nm/s;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
According to the same steps as the above, only replacing I-1 in the step (3) with I-14, I-16, I-18, I-24, I-27, I-35, I-43, I-49 and I-54 respectively to obtain the OLED-2 to OLED-10 provided by the invention.
Following the same procedure as above, only replacing I-1 in step (3) with CBP (comparative compound), comparative example OLED-11 provided by the present invention was obtained. The structure of the CBP is specifically as follows:
Figure BDA0002842517600000261
the performance of the obtained devices OLED-1 to OLED-11 is detected, and the detection results are shown in Table 1.
Table 1: performance test result of OLED device
Figure BDA0002842517600000262
Figure BDA0002842517600000271
As can be seen from the above, the performances of the devices 8 and 9 of the devices OLED-1 to OLED-10 prepared by using the organic material shown in the formula I provided by the invention are basically consistent with those of the comparative devices; the current efficiency of the devices 4, 5, 7 and 10 is higher, and the working voltage is lower than that of the device OLED-11 taking CBP as the main material under the condition of the same brightness; the devices 1, 2,3 and 6 have obviously better operating voltage and current efficiency than the comparative examples, and are green host materials with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. An organic compound having a structure represented by general formula (I):
Figure FDA0002842517590000011
wherein:
L1、L2each independently represents a single bond, substituted or unsubstituted C6～C30Arylene of (a), substituted or unsubstituted C3～C30The heterocyclylene aryl of (a);
R1、R2each independently represents a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring, and at least one group is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; r1、R2May be the same or different;
n is an integer of 1 to 8.
2. An organic compound according to claim 1, wherein the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains at least one five-membered heterocyclic ring, preferably one, two or three five-membered heterocyclic rings; the five-membered heterocyclic ring contains at least one heteroatom, preferably one, two or three heteroatoms; the heteroatom is optionally selected from the group consisting of N atoms, S atoms, and O atoms; when the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains a plurality of hetero atoms, the respective hetero atoms may be the same as each other, may be partially the same as each other, or may be different from each other.
3. An organic compound according to claim 1 or 2, wherein when said group is substituted, the substituent is selected from the group consisting of: halogen, deuterium atom, cyano, C1～C10Alkyl or cycloalkyl of, C2～C6Alkenyl or cycloalkenyl of1～C6Alkoxy or thioalkoxy of C6～C30Arylene of, C3～C30The heteroaryl group of (a).
4. The organic compound according to any one of claims 1 to 3, wherein L is1、L2Represents a single bond; the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from: substituted or unsubstituted carbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl; n is 1 or 2.
5. The organic compound according to any one of claims 1 to 4, wherein in the substituted aromatic group containing a five-membered heterocycle, a substituent used for substitution is optionally selected from: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, indolo, benzothieno, benzofuro; the number of the substituent groups is an integer of 1 to 5, preferably an integer of 1 to 3.
6. An organic compound according to any one of claims 1 to 5, wherein the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure FDA0002842517590000021
Figure FDA0002842517590000031
Figure FDA0002842517590000041
Figure FDA0002842517590000051
preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure FDA0002842517590000052
Figure FDA0002842517590000061
more preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure FDA0002842517590000062
Figure FDA0002842517590000071
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
7. The organic compound according to claim 1, wherein the general formula (I) is selected from the group consisting of compounds represented by the following formulae I-1 to I-56:
Figure FDA0002842517590000072
Figure FDA0002842517590000081
Figure FDA0002842517590000091
8. use of the organic compound according to any one of claims 1 to 7 in an organic electroluminescent device;
preferably, the organic compound is used as a green host material of an electroluminescent layer in an organic electroluminescent device.
9. An organic electroluminescent element comprising an electroluminescent layer containing the organic compound according to any one of claims 1 to 7;
preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer containing the organic compound according to any one of claims 1 to 7, an electron transport layer, an electron injection layer and a cathode layer in sequence from bottom to top;
more preferably, the thickness of the electroluminescent layer may be 10 to 50nm, preferably 20 to 40 nm.
10. A display device or an illumination device, characterized by comprising the organic electroluminescent device according to claim 9.
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Publication number Priority date Publication date Assignee Title
CN104725296A (en) * 2013-12-24 2015-06-24 北京鼎材科技有限公司 Indole derivative and application thereof to organic electroluminescence
CN111233867A (en) * 2018-11-29 2020-06-05 江苏三月光电科技有限公司 Organic compound with carbazole derivative as core and application thereof in organic electroluminescent device
CN111557122A (en) * 2018-01-25 2020-08-18 默克专利有限公司 Material for organic electroluminescent device
CN111662298A (en) * 2020-07-10 2020-09-15 北京燕化集联光电技术有限公司 Novel compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104725296A (en) * 2013-12-24 2015-06-24 北京鼎材科技有限公司 Indole derivative and application thereof to organic electroluminescence
CN111557122A (en) * 2018-01-25 2020-08-18 默克专利有限公司 Material for organic electroluminescent device
CN111233867A (en) * 2018-11-29 2020-06-05 江苏三月光电科技有限公司 Organic compound with carbazole derivative as core and application thereof in organic electroluminescent device
CN111662298A (en) * 2020-07-10 2020-09-15 北京燕化集联光电技术有限公司 Novel compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device

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Application publication date: 20210319