CN116496308A - Condensed cyclic compound and organic light-emitting device comprising the same - Google Patents
Condensed cyclic compound and organic light-emitting device comprising the same Download PDFInfo
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Abstract
The invention relates to the technical field of preparation of organic photoelectric materials, in particular to a condensed-cyclic compound and an organic light-emitting device containing the condensed-cyclic compound. The disclosed fused ring compound has a structure represented by the following formula (1):
Description
Technical Field
The invention relates to the technical field of preparation of organic photoelectric materials, in particular to a condensed-cyclic compound and an organic light-emitting device containing the condensed-cyclic compound.
Background
With the development of multimedia technology and the improvement of informatization requirements, the requirements on the performance of panel displays are higher and higher. The OLED has a series of advantages of autonomous luminescence, low-voltage direct current drive, full solidification, wide viewing angle, rich colors and the like, and is widely paid attention to potential application in a new-generation display and illumination technology, so that the OLED has a very wide application prospect. The organic electroluminescent device is a spontaneous luminescent device, and the mechanism of OLED luminescence is that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and decay in an organic material under the action of an external electric field to generate luminescence. Typical structures of OLEDs include one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer. Although the research of organic electroluminescence is very rapid, there are still many problems to be solved, and at present, the search for a blue light material with high efficiency and long service life is still an important point of attention of those skilled in the art.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a condensed-cyclic compound and an organic light-emitting device containing the condensed-cyclic compound. The invention effectively inhibits the interaction between luminescent molecules by introducing large steric hindrance groups such as diphenyl benzene, triphenyl silicon and the like. The prepared condensed ring compound has better electron and hole receiving capability, can improve the energy transmission performance between a host and an object, reduces the concentration of high-energy excitons in a luminescent layer, and is a blue light material with high efficiency and long service life. Has important application in organic light emitting devices.
In order to achieve the purpose of the invention, the technical scheme of the invention is as follows:
according to one or more embodiments, the present invention provides a condensed-cyclic compound having a structure represented by the following formula (1):
in the formula (1), the D ring and the C ring are each independently a substituted or unsubstituted aryl ring or a heteroalkyl ring; when containing a substituent, the substituent is one or more substitutions, and the substituent is selected from the group consisting of H, deuterium, si, O, N, aryl with 6-20 carbon atoms, alkyl with 1-24 carbon atoms and cycloalkyl with 3-14 carbon atoms;
R 1 、R 2 、R 3 each independently selected from the group consisting of H, deuterium, oxygen, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms, a diarylamino group having 12 to 30 carbon atoms, a diheteroarylamino group having 12 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, and a cycloalkyl group having 3 to 14 carbon atoms.
According to one or more embodiments, the fused ring compound of the present invention has a structure represented by formula (2) or (3):
in the formula (2) or the formula (3), the D ring and the C ring are each independently a substituted or unsubstituted aryl ring or a heteroalkyl ring; when containing a substituent, the substituent is one or more substitutions, and the substituent is selected from the group consisting of H, deuterium, si, O, N, aryl with 6-20 carbon atoms, alkyl with 1-24 carbon atoms and cycloalkyl with 3-14 carbon atoms;
R 1 、R 2 、R 3 each independently selected from the group consisting of H, deuterium, oxygen, aryl of 6 to 20 carbon atoms, heteroaryl of 6 to 20 carbon atoms, diarylamino of 12 to 30 carbon atoms, diheteroarylamino of 12 to 30 carbon atoms, alkyl of 1 to 24 carbon atoms, and cycloalkyl of 3 to 14 carbon atoms; r is R 4 n ，R 5 n ，R 6 n ，R 7 n ，R 8 n ，R 9 n ，R 10 n Is a polysubstituted group, wherein n is the number of substituents, which may be 1 or 2 or 3 or 4 or 5; r is R 4 n -R 10 n Each independently selected from the group consisting of hydrogen, deuterium, alkyl groups of 1 to 24 carbon atoms,Cycloalkyl groups having 3 to 14 carbon atoms and aryl groups having 6 to 20 carbon atoms.
According to one or more embodiments, the fused ring compound of the present invention has a structure represented by formula (4):
wherein R is 1 、R 2 、R 3 、R 9 n Each independently selected from the group consisting of hydrogen, deuterium, alkyl groups having 1 to 24 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, aryl groups having 6 to 20 carbon atoms.
According to one or more embodiments, the fused ring compounds of the present invention are selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
in one aspect, the invention also provides application of the condensed-cyclic compound with the general structure shown in the formula (I) in an electronic device.
Further, the electronic device includes an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quench device (O-FQD), a light emitting electrochemical cell (LEC), and an organic laser diode (O-laser).
In another aspect, the invention also provides an organic electroluminescent device comprising a fused ring compound of the general structure shown in formula (I).
Further, the organic electroluminescent device comprises a cathode, an anode and an organic functional layer between the cathode and the anode; the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a condensed ring compound with a general formula structure shown in the formula (I). The mass percentage of the condensed ring compound is 0.1% -50%.
In another aspect, the present invention also provides an organic optoelectronic device, including a first electrode; a second electrode facing the first electrode; and a luminescent material layer disposed between the first electrode and the second electrode, wherein the luminescent material layer comprises a condensed ring compound having a general structure as shown in formula (I) above. For example, the condensed-cyclic compound may be included as a dopant in the light-emitting material layer.
The invention also provides a composition which comprises the condensed-cyclic compound with the general structure shown in the formula (I).
The invention also provides a preparation which comprises the fused ring compound with the general structure shown in the formula (I) or the composition and at least one solvent. The solvent is not particularly limited, and for example, an unsaturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetrahydronaphthalene, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, a halogenated saturated hydrocarbon solvent such as carbon tetrachloride, chloroform, methylene chloride, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene, an ether solvent such as tetrahydrofuran, tetrahydropyran, an ester solvent such as an alkyl benzoate, and the like, which are known to those skilled in the art, can be used.
The invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices as described above.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, by introducing large steric hindrance groups such as diphenyl benzene, triphenyl silicon and the like, the interaction between luminescent molecules can be effectively inhibited, so that the device efficiency is improved. The fused ring compound provided by the invention has better electron and hole receiving capability, and can improve the energy transmission performance and the thermal stability between a host and an object; when the light-emitting layer is used as a functional layer, particularly as a light-emitting layer in an organic electroluminescent device, the current efficiency is improved, the lighting voltage is reduced, and meanwhile, the service life of the device is also greatly prolonged. It is stated that after most of the electrons and holes are recombined, energy is efficiently transferred to the condensed-cyclic compound for light emission, not heat generation.
Detailed Description
The following describes the present invention in detail. The following description of the constituent elements may be based on the representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples.
The present disclosure may be understood more readily by reference to the following detailed description and the examples included therein. Before the present compounds, devices and/or methods are disclosed and described, it is to be understood that, unless otherwise indicated, they are not limited to specific synthetic methods or specific reagents as such may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing, the exemplary methods and materials are now described.
As used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes a mixture of two or more components. Unless otherwise indicated, all commercial reagents referred to in the following experiments were used directly after purchase.
General synthetic route
The general synthetic route for the compounds of formula (2) of the present invention is shown below:
the general synthetic route for the compounds of formula (3) disclosed in the present invention is shown below:
the general synthetic route for the compounds of formula (4) of the present invention is shown below:
the preparation method of the condensed-cyclic compound, i.e., the guest compound, and the light emitting performance of the device are explained in further detail with reference to the following examples.
Example 1: synthesis of Compound 6
Compound 6-1 (315 mg,1 mmol) and compound 6-2 (274 mg,1 mmol) were dissolved in 50mL of toluene. Under nitrogen atmosphere, 10mL of aqueous sodium carbonate (2M) and tetrakis (triphenylphosphine) palladium (57 mg,0.05 mmoL) were added. After the reaction system was refluxed for 48 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:10 to give product 6-3 (198 mg, yield 47%). Mass spectrum m/z, theory 418.01; actual measurement value M+H:419.14.
synthesis of Compound 6-5: compound 6-3 (418 mg,1 mmol) and compound 6-4 (225 mg,1 mmol) were dissolved in 50mL of toluene. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:3 to give product 6-5 (307 mg, yield 55%). Mass spectrum m/z, theory 563.24; actual measurement value M+H:564.29.
synthesis of Compounds 6-7: compound 6-5 (563.24 mg,1 mmol) and compound 6-6 (268 mg,1 mmol) were dissolved in 50mL of toluene solution. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. After the reaction system was refluxed for 48 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:5 to give product 6-7 (300 mg, yield 43%). Mass spectrum m/z, theory 695.24; actual measurement value M+H:696.30.
synthesis of Compounds 6-9: compound 6-7 (695.24 mg,1 mmol) and compound 6-8 (745 mg,5 mmol) were dissolved in 50mL of toluene. Sodium tert-butoxide (960 mg,10 mmoL), palladium acetate (12 mg,0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:2 to give product 6-9 (338 mg, yield 39%). Mass spectrum m/z, theory 864.45; actual measurement value M+H:865.48.
synthesis of Compounds 6-11: compound 6-9 (864.45 mg,1 mmol) and compound 6-10 (1.69 mg,5 mmol) were dissolved in 50mL of toluene solution. Sodium tert-butoxide (960 mg,10 mmoL), palladium acetate (12 mg,0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmoL) were added under nitrogen atmosphere. The reaction system was heated to reflux for 72 hours and cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give product 6-11 (402 mg, yield 38%). Mass spectrum m/z, theory 1074.45; actual measurement value M+H:1075.48.
synthesis of Compound 6: compounds 6-11 (1.074 g,1 mmol) were dissolved in 60mL dry tert-butylbenzene. The reaction was cooled to-78℃and BuLi (1mL,2mmoL,2M in hexane) was slowly added. After 4 hours of reaction at-78 ℃, BBr is slowly added 3 (247 mg,1 mmol). After 1 hour of reaction at-50 ℃, the temperature was raised to room temperature, then N, N-diisopropylethylamine (387 mg,3 mmoL) was added, followed by heating to 120℃for reaction for 12 hours. Cooling to room temperatureAfter that, 5mL of an aqueous sodium acetate solution (1M) was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:8 to give product 6 (325 mg, yield 32%). Mass spectrum m/z, theory 1004.53; actual measurement value M+H:1005.57.
EXAMPLE 2 Synthesis of Compound 25
Synthesis of Compound 25-3: compound 25-1 (1.71 g,10 mmoL) and compound 25-2 (2.54 g,10 mmoL) were dissolved in 100mL of toluene solution. Under nitrogen atmosphere, 30mL of aqueous sodium carbonate (2M) and tetrakis (triphenylphosphine) palladium (346.5 mg,0.3 mmoL) were added. After the reaction system was refluxed for 48 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give 25-3 (2.13 g, yield 71%). Mass spectrum m/z, theory 301.18; actual measurement value M+H:302.23.
synthesis of Compound 25-5: compound 25-4 (2.81 g,10 mmoL) and compound 25-2 (2.54 g,10 mmoL) were dissolved in 100mL of toluene solution. Under nitrogen atmosphere, 30mL of aqueous sodium carbonate (2M) and tetrakis (triphenylphosphine) palladium (346.5 mg,0.3 mmoL) were added. After the reaction system was refluxed for 48 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:30, to give 25-5 (1.56 g, yield 43%). Mass spectrum m/z, theory 364.08; actual measurement value M+H:365.13.
synthesis of Compound 25-6: compound 25-3 (301 mg,1 mmol) and compound 25-5 (284 mg,1 mmol) were dissolved in 50mL of toluene. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:3 to give the product 25-6 (332 mg, yield 57%). Mass spectrum m/z, theory 585.34; actual measurement value M+H:586.36.
synthesis of Compound 25-8: compound 25-6 (585 mg,1 mmol) and compound 25-7 (324 mg,1 mmol) were dissolved in 50mL of toluene. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:5, yield 25-6 (302 mg, 36% yield). Mass spectrum m/z, theory 829.31; actual measurement value M+H:830.35.
synthesis of Compound 25-11: compound 25-9 (0.225 g,1 mmol) and compound 25-10 (0.267 g,1 mmol) were dissolved in 50mL of toluene solution. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give the product 25-11 (265 mg, yield 64%). Mass spectrum m/z, theory 413.22; actual measurement value M+H:414.25.
synthesis of Compounds 25-12: compound 25-8 (0.829 g,1 mmol) and compound 25-11 (0.413 g,1 mmol) were dissolved in 50mL of toluene solution. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:8 to give 25-12 (312 mg, yield 27%). Mass spectrum m/z, theory 1162.60; actual measurement value M+H:1163.64.
synthesis of Compound 25: tert-butyllithium (1.25 mL,1.6M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compounds 25-12 (1.163 g,1 mmoL) in tert-butylbenzene (100 mL) under nitrogen at zero. The system is reacted for 4 hours at 60 ℃, cooled to-50 ℃, and then BBr is added 3 (494 mg,2 mmol). After 1 hour of reaction at room temperature, N-diisopropylethylamine (299 mg,2 mmol) was added. Then the temperature is raised to 120 ℃ for reaction for 12 hours. After cooling to room temperature, 5mL of aqueous sodium acetate (1M) was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:8 to give product 25 (256 mg, yield 23%). Mass spectrum m/z, theory 1136.62; actual measurement value M+H:1137.71.
example 3: synthesis of Compound 37
Synthesis of Compound 37-3: compound 37-1 (0.323 g,1 mmol) and compound 37-2 (0.281g, 1 mmol) are dissolved in 50mL of toluene. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was heated to reflux for 72 hours and cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give the product 37-3 (356 mg, yield 68%). Mass spectrum m/z, theory 525.18; actual measurement value M+H:526.23.
synthesis of Compound 37-5: compound 37-3 (0.525 g,1 mmol) and compound 37-4 (0.149 g,1 mmol) are dissolved in 50mL of toluene. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was heated to reflux for 72 hours and cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:6, to give a product 37-5 (298 mg, yield 50%). Mass spectrum m/z, theory 594.37; actual measurement value M+H:595.43.
synthesis of Compound 37-7:
BuLi (0.5mL,1mmoL,2M in hexane) was slowly added to a solution of compound 37-6 (211 mg,1 mmol) in tetrahydrofuran (50 mL) at-78deg.C. After 3 hours of reaction, triphenylchlorosilane (295 mg,1 mmol) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, then allowed to react at 80℃for 6 hours. After cooling to room temperature, ice water 1mL was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:9, yield 37-7 (225 mg, 57% yield). Mass spectrum m/z, theory 392.10; actual measurement value M+H:393.18.
synthesis of Compound 37-8:
to a solution of compound 37-7 (390 mg,1 mmol) in 50mL of DMF was slowly added NBS (178 mg,1 mmol). After reacting for 12 hours at room temperature, the temperature is raised to 80 ℃ for reacting for 12 hours. After cooling to room temperature, the solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:9, yield 37-8 (258 mg, 55% yield). Mass spectrum m/z, theory 470.02; actual measurement value M+H:471.12.
synthesis of Compound 37-9: lithium diisopropylamide (0.5mL,1mmoL,2.0M solution in THF/n-heptane) was slowly added to a solution of compound 37-8 (470 mg,1 mmol) in tetrahydrofuran (50 mL) at-78deg.C. After 3 hours of reaction at-78 ℃, the reaction was allowed to proceed to room temperature for 12 hours, and then 1mL of ice water was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:9 to give product 37-9 (208 mg, yield 44%). Mass spectrum m/z, theory 470.02; actual measurement value M+H:471.07.
synthesis of Compounds 37-10: compound 37-5 (0.594 g,1 mmol) and compound 37-9 (0.470 g,1 mmol) were dissolved in 50mL of toluene solution. Sodium tert-butoxide (192 mg,2 mmol), palladium acetate (12 mg,0.05 mmol) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmol) were added under nitrogen. The reaction system was heated to reflux for 72 hours and cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:5 to give the product 37-10 (324 mg, yield 33%). Mass spectrum m/z, theory 984.46; actual measurement value M+H:985.51.
synthesis of Compound 37: tert-butyllithium (1.25 mL,1.6M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compound 37-10 (984 mg,1 mmoL) in tert-butylbenzene (100 mL) under nitrogen at zero degrees. The system is reacted for 4 hours at 60 ℃, cooled to-50 ℃, and then BBr is added 3 (494 mg,2 mmol). After 1 hour of reaction at room temperature, N-diisopropylethylamine (299 mg,2 mmol) was added. Then the temperature is raised to 120 ℃ for reaction for 12 hours. After cooling to room temperature, 5mL of aqueous sodium acetate (1M) was added. General purpose medicineThe solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3X 100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:7 to give product 37 (238 mg, yield 25%). Mass spectrum m/z, theory 958.49; actual measurement value M+H:959.52.
example 4: synthesis of Compound 5
Compound 5 was synthesized referring to the synthetic route for compound 6. The yield of the final product was 23%. Mass spectrum m/z, theory 1040.62; actual measurement value M+H:1041.64.
example 5: synthesis of Compound 4
Compound 4 was synthesized referring to the synthetic route for compound 6. The yield of the final product was 31%. Mass spectrum m/z, theory 928.50; actual measurement value M+H:929.52.
example 6: synthesis of Compound 19
Compound 19 was synthesized referring to the synthetic route for compound 6. The yield of the final product was 33%. Mass spectrum m/z, theory 1151.63; actual measurement value M+H:1152.65.
example 7: synthesis of Compound 17
Compound 17 was synthesized referring to the synthetic route for compound 6. The yield of the final product was 28%. Mass spectrum m/z, theory 1060.59; actual measurement value M+H:1061.66.
example 8: synthesis of Compound 29
Compound 29 was synthesized referring to the synthetic route for compound 6. The yield of the final product was 30%. Mass spectrum m/z, theory 1090.64; actual measurement value M+H:1091.66.
example 9: synthesis of Compound 38
Compound 38 was synthesized referring to the synthetic route for compound 37. The yield of the final product was 29%. Mass spectrum m/z, theory 978.46; actual measurement value M+H:979.49.
example 10: synthesis of Compound 33
Compound 33 was synthesized referring to the synthetic route for compound 25. The yield of the final product was 26%. Mass spectrum m/z, theory 1114.64; actual measurement value M+H:1115.68.
manufacturing of OLED device:
the OLED device of the present invention contains a hole transporting layer, and the hole transporting material may preferably be selected from known or unknown materials, particularly preferably from the following structures, but does not represent that the present invention is limited to the following structures (Ph is phenyl):
the OLED device of the present invention comprises a hole injection layer which may be selected from known or unknown materials, particularly preferably from the following structures, but is not meant to limit the present invention to the following structures:
the OLED device of the present invention contains a host material, which may be selected from known or unknown materials, particularly preferably selected from the following structures, but does not represent the limitation of the present invention to the following structures:
the OLED device of the present invention comprises an electron transport layer which may be selected from known or unknown materials, particularly preferably from the following structures, but is not meant to limit the present invention to the following structures:
as a preferred embodiment of the device, HT-1 and P-3 are co-evaporated or evaporated to form a 10nm Hole Injection Layer (HIL) (wherein the volume ratio of HT-1 to P-3 is 95:5), a 90nm Hole Transport Layer (HTL) on the surface or anode of ITO glass with a light emitting area of 2mm by 2mm, HT-8 is then evaporated to form an Electron Blocking Layer (EBL) with a thickness of 10nm, then a host material H-1 and a fused ring compound 6 (guest material) prepared in example 1 of the present invention are co-evaporated to form a 35nm light emitting layer (EML) (the volume ratio of fused ring compound to host material is 3:97), and finally an 35nm Electron Transport Layer (ETL) (wherein the volume ratio of ET-3 to LiQ is 1:1) is co-evaporated to form a 35nm Electron Transport Layer (ETL) with ET-3 and then a cathode Al is evaporated to 70nm on the hole transport layer, thereby manufacturing an organic electroluminescent diode, which is the first embodiment of the device.
Referring to the method provided in the first device example, the prepared condensed-cyclic compounds 4, 5, 17, 19, 25, 29, 33, 37 and 38 are selected as the substitute compounds 6 to be implemented, and the organic electroluminescent diode is prepared by co-evaporating the substitute compounds and the host compound in a volume ratio of 3:97 to form a luminescent layer, which is denoted as device examples two to ten.
Production of comparative examples 1 to 2
Comparative examples 1 to 2 were prepared by the method provided in device example one above, except that BN-1, BN-2 was used as the guest material of the light-emitting layer in place of the condensed-cyclic compound of the present invention in comparative examples 1 to 2, respectively. The chemical structures of the compounds BN-1, BN-2 in the comparative examples are as follows:
the characteristics of the device examples and comparative examples prepared above, such as current efficiency, voltage and lifetime, were tested by standard methods, and the device luminescence characteristic data are shown in table 1.
TABLE 1 light emission characteristics data sheet for devices
As can be seen from table 1, the specific condensed-cyclic compound disclosed by the invention is applied to the organic electroluminescent device as the dopant of the luminescent layer, and compared with the comparative example, better starting voltage is obtained, and the luminescent efficiency and the service life of the device are obviously improved. The condensed-cyclic compound disclosed by the invention can optimize the performance of devices and has a certain commercial application value.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.
Claims (12)
1. A condensed-cyclic compound characterized by having a structure represented by the following formula (1):
in the formula (1), the D ring and the C ring are each independently a substituted or unsubstituted aryl ring or a heteroalkyl ring; when containing a substituent, the substituent is one or more substitutions, and the substituent is selected from the group consisting of H, deuterium, si, O, N, aryl with 6-20 carbon atoms, alkyl with 1-24 carbon atoms and cycloalkyl with 3-14 carbon atoms;
R 1 、R 2 、R 3 each independently selected from the group consisting of H, deuterium, oxygen, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms, a diarylamino group having 12 to 30 carbon atoms, a diheteroarylamino group having 12 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, and a cycloalkyl group having 3 to 14 carbon atoms.
2. The fused ring compound according to claim 1, wherein the fused ring compound has a structure represented by formula (2) or formula (3):
in the formula (2) or the formula (3), the D ring and the C ring are each independently a substituted or unsubstituted aryl ring or a heteroalkyl ring; when containing a substituent, the substituent is one or more substitutions, and the substituent is selected from the group consisting of H, deuterium, si, O, N, aryl with 6-20 carbon atoms, alkyl with 1-24 carbon atoms and cycloalkyl with 3-14 carbon atoms;
R 1 、R 2 、R 3 each independently selected from the group consisting of H, deuterium, oxygen, aryl of 6 to 20 carbon atoms, heteroaryl of 6 to 20 carbon atoms, diarylamino of 12 to 30 carbon atoms, diheteroarylamino of 12 to 30 carbon atoms, alkyl of 1 to 24 carbon atoms, and cycloalkyl of 3 to 14 carbon atoms; r is R 4 n ，R 5 n ，R 6 n ，R 7 n ，R 8 n ，R 9 n ，R 10 n Is a polysubstituted group, wherein n is a substituent number and may be 1 or 2 or3 or 4 or 5; r is R 4 n -R 10 n Each independently selected from the group consisting of hydrogen, deuterium, alkyl groups having 1 to 24 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, aryl groups having 6 to 20 carbon atoms.
3. The fused ring compound according to claim 1, wherein the fused ring compound has a structure represented by formula (4):
wherein R is 1 、R 2 、R 3 、R 9 n Each independently selected from the group consisting of hydrogen, deuterium, alkyl groups having 1 to 24 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, aryl groups having 6 to 20 carbon atoms.
4. The fused ring compound according to claim 1, wherein the fused ring compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
5. use of the fused ring compound according to any one of claims 1 to 4 in an electronic device.
6. The use according to claim 5, wherein the electronic device is an organic electroluminescent device, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quench device, a light emitting electrochemical cell and/or an organic laser diode.
7. An organic electroluminescent device comprising the fused ring compound according to any one of claims 1 to 4.
8. The organic electroluminescent device of claim 7, comprising a cathode, an anode, and an organic functional layer therebetween; the organic functional layer comprises a light-emitting layer, wherein the light-emitting layer comprises the condensed cyclic compound according to any one of claims 1 to 4.
9. An organic photoelectric device including a first electrode, a second electrode facing the first electrode, and a light emitting material layer disposed between the first electrode and the second electrode; a light-emitting material layer comprising the condensed cyclic compound according to any one of claims 1 to 4.
10. A composition comprising the fused ring compound of any one of claims 1-4.
11. A formulation comprising the fused ring compound of any one of claims 1-4 and at least one solvent.
12. A display or lighting device, characterized in that it comprises one or more of the organic electroluminescent devices of claim 9.
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