CN112624959A - Heterocyclic compound containing indolone and application thereof - Google Patents

Heterocyclic compound containing indolone and application thereof Download PDF

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Publication number
CN112624959A
CN112624959A CN202011497122.8A CN202011497122A CN112624959A CN 112624959 A CN112624959 A CN 112624959A CN 202011497122 A CN202011497122 A CN 202011497122A CN 112624959 A CN112624959 A CN 112624959A
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group
substituted
unsubstituted
indolone
heterocyclic compound
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Inventor
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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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Priority to CN202011497122.8A priority Critical patent/CN112624959A/en
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Abstract

The invention relates to the technical field of organic electroluminescent display, in particular to a heterocyclic compound containing indolone and application thereof. The indole ketone-containing heterocyclic 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 and used as a red light main body material.

Description

Heterocyclic compound containing indolone and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to a heterocyclic compound containing indolone 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. Therefore, the phosphorescent material is often incorporated as a guest into the host material to reduce the concentration quenching phenomenon itself. 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 a stable and efficient main material which can be used for a red phosphorescent organic electroluminescent device, wherein the main material has a high triplet state energy level, a good carrier mobility, high thermal stability and film forming stability, and can be matched with an adjacent energy level; the material is applied to corresponding red phosphorescent OLED devices, can reduce driving voltage and improve the luminous efficiency of the devices.
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 a strong electron donating arylamine group, can be used as a red light main body material, is applied to an OLED device, can reduce the driving voltage, and improves the luminous efficiency of the device.
The invention provides an indolone-containing heterocyclic compound, which has a structure shown as a general formula (I):
Figure BDA0002842512830000021
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
Figure BDA0002842512830000031
R1、R2May be the same or different;
n is an integer of 1 to 8.
Preferably, Ar is1、Ar2Each independently represents a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring, and Ar1、Ar2May be the same or different; ar is1、Ar2Can be independently existed, can be condensed with adjacent benzene ring or heterocyclic ring, or two adjacent positions can be connected to form a ring, or form a ring through NR, CR 'R', O, S;
the R, R 'and R' are each independently selected from hydrogen, C1～C8Alkyl of (C)5～C10Cycloalkyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of the heterocyclic aryl groups of (a), or a combination thereof.
Preferably, when the above groups are substituted, the substituents are selected from: 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 is1Represents a single bond; ar is1、Ar2Each independently represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted C4～C6Substituted or unsubstituted polyphenyl aliphatic hydrocarbon, substituted or unsubstituted condensed ring aromatic hydrocarbon, substituted or unsubstituted condensed heterocyclic aromatic hydrocarbon, substituted or unsubstituted biaryl hydrocarbon, substituted or unsubstituted spirobifluorene group; when the above groups are substituted, the substituents are selected from: deuterium atom, linear or branched alkyl group, cycloalkyl group, aryl group, amino group, alkylamino group, arylamino group, heteroaryl group, monocyclic aryl group, benzo group, pyrido group, phenanthro group, naphtho group, indo group (e.g., N-phenylindo group), benzothieno group, benzofuro group;the number of the substituent groups is an integer from 1 to 7; n is 1 or 2.
In the above-mentioned technical solutions, the straight or branched alkyl group is preferably C1～C5Linear or branched alkyl.
Preferably, L is1Represents a single bond; ar is1、Ar2Each independently represents a substituted or unsubstituted benzene ring, C4～C6Heteroaromatic rings, biphenyl, indene, naphthalene, acenaphthylene, fluorene, spirobifluorene, phenanthrene, anthracene, fluoranthene, pyrene, triphenylene, benzo (a) anthracene, benzo (b) fluoranthene, benzo (k) fluoranthene, benzo (a) pyrene, xanthene, acridine, carbazole, dibenzofuran, or dibenzothiophene; when the above groups are substituted, the substituents are selected from: deuterium atom, C1～C5Linear or branched alkyl, C3～C6Cycloalkyl, phenyl, diphenylamino, benzo, pyrido, phenanthro, naphtho, indolo (e.g.N-benzaindolo), benzothieno, benzofuro; the number of the substituent groups is an integer of 1-3; n is 1.
Preferably, the
Figure BDA0002842512830000041
Selected from the group consisting of:
Figure BDA0002842512830000042
Figure BDA0002842512830000051
further, the
Figure BDA0002842512830000052
Selected from the group consisting of:
Figure BDA0002842512830000053
Figure BDA0002842512830000061
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 BDA0002842512830000062
Figure BDA0002842512830000071
Figure BDA0002842512830000081
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 a proper position in the matrix structure, namely, an arylamine structure or benzo heterocyclic structure with strong electron donating capability is introduced into the structure, so that a novel structure OLED material is obtained; the red light-emitting material is applied to an OLED device and used as a red 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 provide the application of the heterocyclic compound containing the indolone in an organic electroluminescent device;
preferably, the indolone heterocyclic compound is used as a red host material of an electroluminescent layer in an organic electroluminescent device.
The third purpose of the invention is to provide an organic electroluminescent device, which comprises an electroluminescent layer containing the indole ketone-containing heterocyclic compound.
Preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer containing the heterocyclic compound containing the indolone, 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 and used as a red light main body material.
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 suitable catalyst, solvent, and halide, and determining suitable reaction temperature, time, material ratio, etc., which is 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 in use
Figure BDA0002842512830000101
The synthesis route is as follows:
Figure BDA0002842512830000102
(2) when R is1And R2In a different sense, R1Is composed of
Figure BDA0002842512830000103
The synthesis route is as follows:
Figure BDA0002842512830000104
(3) when R is1And R2In a different sense, R2Is composed of
Figure BDA0002842512830000105
The synthesis route is as follows:
Figure BDA0002842512830000106
(4) when R is1And R2Different from each other are
Figure BDA0002842512830000107
The synthesis route is as follows:
Figure BDA0002842512830000108
EXAMPLE 1 Synthesis of Compound I-1
Figure BDA0002842512830000111
The synthetic route is as follows:
Figure BDA0002842512830000112
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (28.8g, 0.3mol), diphenylamine (33.8g, 0.2mol) and 400ml of toluene were added in this order. 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 53.2g pale yellow solid with about 83% yield.
Product MS (m/e): 641.25, respectively; elemental analysis (C)46H31N3O): theoretical value C: 86.09%, H: 4.87%, N: 6.55 percent; found value C: 86.18%, H: 4.94%, N: 6.41 percent.
EXAMPLE 2 Synthesis of Compound I-14
Figure BDA0002842512830000113
The synthetic route is as follows:
Figure BDA0002842512830000121
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 was equipped with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (14.4g, 0.15mol), bis (4-isopropylphenyl) amine (25.3g, 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 (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 59.3g pale yellow solid with yield about 79%.
Product MS (m/e): 750.36, respectively; elemental analysis (C)55H46N2O): theoretical value C: 87.97%, H: 6.17%, N: 3.73 percent; found value C: 87.90%, H: 6.26%, N: 3.68 percent.
EXAMPLE 3 Synthesis of Compound I-19
Figure BDA0002842512830000131
The synthetic route is as follows:
Figure BDA0002842512830000132
into a 1L three-necked flask, M3(51.9g, 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. 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, ethyl acetate is pulped, 51.0g of light yellow solid I-19-1 is obtained by filtration, and the yield is about 90 percent.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium tert-butoxide (14.4g, 0.15mol), dinaphthylamine (26.9g, 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 (56.7g, 0.1mol) I-19-1 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 56.0g pale yellow solid with yield of about 70%.
Product MS (m/e): 800.28, respectively; elemental analysis (C)60H36N2O): theoretical value C: 89.97%, H: 4.53%, N: 3.50 percent; found value C: 89.92%, H: 4.66%, N: 3.43 percent.
EXAMPLE 4 Synthesis of Compound I-22
Figure BDA0002842512830000141
The synthetic route is as follows:
Figure BDA0002842512830000142
A2L three-necked flask was stirred with magnetic stirring and then purged with nitrogen, followed by sequentially adding sodium t-butoxide (28.8g, 0.3mol), bis ([1,1' -biphenyl ] -4-yl) amine (64.2g, 0.2mol) and toluene 400 ml. 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) M4 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 72.8g pale yellow solid with yield of about 77%.
Product MS (m/e): 945.37, respectively; elemental analysis (C)70H47N3O): theoretical value C: 88.86%, H: 5.01%, N: 4.44 percent; found value C: 88.92%, H: 5.08%, N: 4.31 percent.
EXAMPLE 5 Synthesis of Compound I-30
Figure BDA0002842512830000151
The synthetic route is as follows:
Figure BDA0002842512830000152
into a 1L three-necked flask, M5(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 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 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 29.9g of light yellow solid I-30-1 is obtained through filtration, and the yield is about 69%.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (14.4g, 0.15mol), N- (9, 9-dimethyl-9H-fluoren-2-yl) triphenyl-2-amine (43.5g, 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 (43.4g, 0.1mol) I-30-1 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 61.6g pale yellow solid with yield of about 74%.
Product MS (m/e): 833.35, respectively; elemental analysis (C)62H39D3N2O): theoretical value C: 89.29%, H: 5.44%, N: 3.36 percent; found value C: 89.35%, H: 5.50%, N: 3.20 percent.
EXAMPLE 6 Synthesis of Compound I-40
Figure BDA0002842512830000161
The synthetic route is as follows:
Figure BDA0002842512830000162
m6(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). 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, 46.0g of light yellow solid I-40-1 is obtained after filtration, and the yield is about 88%.
A2L three-necked flask was magnetically stirred, and then sodium t-butoxide (14.4g, 0.15mol), N- (9, 9-dimethyl-9H-fluoren-2-yl) dibenzo [ b, d ] furan-2-amine (37.5g, 0.1mol) and 400ml of toluene were added in this order after nitrogen substitution. 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-40-1 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 56.9g pale yellow solid with yield of about 66%.
Product MS (m/e): 862.27, respectively; elemental analysis (C)61H38N2OS): theoretical value C: 84.89%, H: 4.44%, N: 3.25 percent; found value C: 84.93%, H: 4.50%, N: 3.11 percent.
EXAMPLE 7 Synthesis of Compound I-41
Figure BDA0002842512830000171
The synthetic route is as follows:
Figure BDA0002842512830000172
into a 1L three-necked flask, M7(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, and ethyl acetate were charged150mL of alcohol and 150mL of water, replacing and protecting the reaction system by nitrogen, and adding 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 filtration is carried out to obtain 45.8g of light yellow solid I-41-1 with the yield of about 86%.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (14.4g, 0.15mol), 3, 7-dimethyl-10H-phenothiazine (22.7g, 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 (53.3g, 0.1mol) I-41-1 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 43.4g pale yellow solid with yield of about 60%.
Product MS (m/e): 724.25, respectively; elemental analysis (C)51H36N2OS): theoretical value C: 84.50%, H: 5.01%, N: 3.86 percent; found value C: 84.55%, H: 5.09%, N: 3.73 percent.
EXAMPLE 8 Synthesis of Compound I-43
Figure BDA0002842512830000181
The synthetic route is as follows:
Figure BDA0002842512830000191
into a 1L three-necked flask, M8(41.9g, 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 was purged with nitrogen and Pd (PPh) was added3)4(11.5g, 10 mmol). The reaction was stopped by heating and refluxing the reaction mixture (at a temperature of about 78 ℃ C.) for 3 hours. 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 38.8g of light yellow solid I-43-1 with the yield of about 76%.
A2L three-necked flask was stirred with magnetic stirring, and after nitrogen substitution, sodium t-butoxide (14.4g, 0.15mol), 10H-phenoxazine (18.3g, 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 of (58.9g, 0.1mol) M3-1 and 100ml toluene was added dropwise, and the reaction was terminated by controlling the temperature at 80-120 ℃ for 4 hours. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 54.5g pale yellow solid I-43 with yield about 83%.
Product MS (m/e): 657.25, respectively; elemental analysis (C)47H27D3N2O2): theoretical value C: 85.82%, H: 5.06%, N: 4.26 percent; found value C: 85.90%, H: 5.14%, N: 4.11 percent.
EXAMPLE 9 Synthesis of Compound I-55
Figure BDA0002842512830000201
The synthetic route is as follows:
Figure BDA0002842512830000202
under the protection of nitrogen, a 2L three-mouth bottle is stirred by magnetic force, M8(41.9g, 0.1mol), N- ([ [1,1' -biphenyl ] -4-yl ] dibenzo [ b, d ] furan-3-amine (33.5g, 0.1mol), copper powder (6.3g, 0.1mol), 18-crown-6 (26.4g, 0.1mol), potassium carbonate (20.7g, 0.15mol) and o-dichlorobenzene (800 ml) are added in sequence after nitrogen replacement, heating and reflux reaction are carried out for 20 hours under the protection of nitrogen, the temperature is reduced after the reaction is finished, water is added, o-dichlorobenzene is evaporated, a solid product is washed by water, filtered and dried, and subjected to column chromatographic separation to obtain 32.4g of light yellow solid I-55-1 with the yield of about 48 percent.
A2L three-necked flask was magnetically stirred, and then sodium t-butoxide (14.4g, 0.15mol), N1, N1-diphenyl-N4- (p-tolyl) benzene-1, 4-diamine (35.0g, 0.1mol) and toluene (400 ml) were added in this order after nitrogen substitution. 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 (67.4g, 0.1mol) I-55-1 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 76.1g pale yellow solid I-55 with yield of about 77%.
Product MS (m/e): 988.38, respectively; elemental analysis (C)71H48N4O2): theoretical value C: 86.21%, H: 4.89%, N: 5.66 percent; found value C: 86.26%, H: 4.94%, N: 5.52 percent.
EXAMPLE 10 Synthesis of Compound I-56
Figure BDA0002842512830000211
The synthetic route is as follows:
Figure BDA0002842512830000212
under the protection of nitrogen, a 2L three-necked flask was equipped with magnetic stirring, and after nitrogen replacement, M9(42.0g, 0.1mol), N- (9, 9-dimethyl-9H-fluoren-2-yl) dibenzo [ b, d ] furan-2-amine (37.5g, 0.1mol), copper powder (6.3g, 0.1mol), 18-crown-6 (26.4g, 0.1mol), potassium carbonate (20.7g, 0.15mol), and 800ml of o-dichlorobenzene were sequentially added. And heating and refluxing for reaction for 20 hours under the protection of nitrogen, and finishing the reaction. Cooling, adding water, and distilling off o-dichlorobenzene. The solid product is washed by water, filtered and dried, and is separated by column chromatography and dried to obtain 32.2g of light yellow solid I-56-1 with the yield of about 45 percent.
A2L three-necked flask is stirred by magnetic stirring, and after nitrogen replacement, sodium tert-butoxide (14.4g, 0.15mol), N- (naphthalene-2-yl) -9-phenyl-9H-carbazole-3-amine (38.4g, 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 (71.5g, 0.1mol) I-56-1 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 74.4g pale yellow solid I-56 with yield of about 70%.
Product MS (m/e): 1063.39, respectively; elemental analysis (C)76H49N5O2): theoretical value C: 85.77%, H: 4.64%, N: 6.58 percent; found value C: 85.83%, H: 4.70%, N: 6.44 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 red host materials
The embodiment provides a group of OLED red 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 BDA0002842512830000221
the preparation method comprises the following steps:
(1) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating the second hole injection layer HT01The speed is 0.1nm/s, and the thickness is 40 nm; then evaporating a hole transport layer at the evaporation rate of 0.1nm/s and the evaporation film thickness of 20 nm;
(3) EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises the red main body material I-1 and the dye material, the evaporation rate of the main body material is adjusted to be 0.1nm/s by utilizing a multi-source co-evaporation method, and the dye material Ir (piq)2The acac concentration is 5%, and the total film thickness of evaporation plating is 30 nm; PRH01 was used as a contrast material for the host material;
(4) taking Bphen as an electron transport layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40 nm;
(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-19, I-22, I-30, I-40, I-41, I-43, I-55 and I-56 respectively, and using the materials as red light host materials to obtain OLED-2-OLED-10 provided by the invention respectively.
Comparative example OLED-11 provided by the present invention was obtained by following the same procedure as above, replacing only I-1 in step (3) with commercial PRH01 (comparative compound). The PRH01 has the following structure:
Figure BDA0002842512830000231
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 BDA0002842512830000241
From the above, the performance of the devices prepared by using the organic material containing the arylamine structure shown in the formula I as the red light main body material is basically consistent with that of the devices 9 and 10; the current efficiency of the devices 2, 5, 6 and 8 is higher, and the working voltage is lower than that of the contrast device under the condition of the same brightness; the devices 1, 3, 4, 7 have the best performance, are obviously superior to the comparison device in the aspects of working voltage and current efficiency, and are red light 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 indolone-containing heterocyclic compound having a structure represented by general formula (I):
Figure FDA0002842512820000011
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
Figure FDA0002842512820000012
R1、R2May be the same or different;
n is an integer of 1 to 8.
2. The indolone-containing heterocyclic compound according to claim 1, wherein Ar is1、Ar2Each independently represents a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ringGroup of Ar1、Ar2May be the same or different; ar is1、Ar2Can be independently existed, can be condensed with adjacent benzene ring or heterocyclic ring, or two adjacent positions can be connected to form a ring, or form a ring through NR, CR 'R', O, S;
the R, R 'and R' are each independently selected from hydrogen, C1～C8Alkyl of (C)5～C10Cycloalkyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of the heterocyclic aryl groups of (a), or a combination thereof.
3. The indolone containing heterocyclic compound according to claim 1 or 2, wherein when the above group is substituted, the substituent is selected from the group consisting of: 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).
4. The indolone-containing heterocyclic compound according to any one of claims 1 to 3, wherein L is1Represents a single bond; ar is1、Ar2Each independently represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted C4～C6Substituted or unsubstituted polyphenyl aliphatic hydrocarbon, substituted or unsubstituted condensed ring aromatic hydrocarbon, substituted or unsubstituted condensed heterocyclic aromatic hydrocarbon, substituted or unsubstituted biaryl hydrocarbon, substituted or unsubstituted spirobifluorene group; when the above groups are substituted, the substituents are selected from: deuterium atom, linear or branched alkyl group, cycloalkyl group, aryl group, amino group, alkylamino group, arylamino group, heteroaryl group, monocyclic aryl group, benzo group, pyrido group, phenanthro group, naphtho group, indo group, benzothiopheno group, benzofuro group; the number of the substituent groups is an integer from 1 to 7; n is 1 or 2.
5. The indolone-containing heterocyclic compound according to any one of claims 1 to 3, wherein L is1Represents a single bond; ar is1、Ar2Each independently represents a substituted or unsubstituted benzene ring, C4～C6Heteroaromatic rings, biphenyl, indene, naphthalene, acenaphthylene, fluorene, spirobifluorene, phenanthrene, anthracene, fluoranthene, pyrene, triphenylene, benzo (a) anthracene, benzo (b) fluoranthene, benzo (k) fluoranthene, benzo (a) pyrene, xanthene, acridine, carbazole, dibenzofuran, or dibenzothiophene; when the above groups are substituted, the substituents are selected from: deuterium atom, C1～C5Linear or branched alkyl, C3～C6Cycloalkyl, phenyl, diphenylamino, benzo, pyrido, phenanthro, naphtho, indolo, benzothieno, benzofuro; the number of the substituent groups is an integer of 1-3; n is 1.
6. The indolone-containing heterocyclic compound according to any one of claims 1 to 5, wherein the indolone-containing heterocyclic compound is
Figure FDA0002842512820000021
Selected from the group consisting of:
Figure FDA0002842512820000022
Figure FDA0002842512820000031
Figure FDA0002842512820000041
preferably, the
Figure FDA0002842512820000042
Selected from the group consisting of:
Figure FDA0002842512820000043
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
7. The indolone-containing heterocyclic 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 FDA0002842512820000044
Figure FDA0002842512820000051
Figure FDA0002842512820000061
Figure FDA0002842512820000071
8. use of the heterocyclic compound containing an indolone according to any one of claims 1 to 7 in an organic electroluminescent device;
preferably, the indolone heterocyclic compound is used as a red host material of an electroluminescent layer in an organic electroluminescent device.
9. An organic electroluminescent element comprising an electroluminescent layer containing the indole ketone-containing heterocyclic 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 heterocyclic compound containing indolone 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.
CN202011497122.8A 2020-12-17 2020-12-17 Heterocyclic compound containing indolone and application thereof Pending CN112624959A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101205210A (en) * 2007-12-19 2008-06-25 华东理工大学 Indole derivatives and uses thereof
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
CN106458997A (en) * 2014-05-08 2017-02-22 罗门哈斯电子材料韩国有限公司 An electron transport material and an organic electroluminescence device comprising the same
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101205210A (en) * 2007-12-19 2008-06-25 华东理工大学 Indole derivatives and uses thereof
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
CN106458997A (en) * 2014-05-08 2017-02-22 罗门哈斯电子材料韩国有限公司 An electron transport material and an organic electroluminescence device comprising the same
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

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Application publication date: 20210409