CN114685482A - Organic electroluminescent compound and application thereof - Google Patents

Organic electroluminescent compound and application thereof Download PDF

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CN114685482A
CN114685482A CN202011583717.5A CN202011583717A CN114685482A CN 114685482 A CN114685482 A CN 114685482A CN 202011583717 A CN202011583717 A CN 202011583717A CN 114685482 A CN114685482 A CN 114685482A
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unsubstituted
organic electroluminescent
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aryl
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李祥智
蔡烨
丁欢达
魏定纬
陈志宽
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Ningbo Lumilan Advanced Materials Co Ltd
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Ningbo Lumilan Advanced Materials Co Ltd
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Abstract

The invention provides an organic electroluminescent compound and application thereof, wherein the organic electroluminescent compound has a structure shown in a formula I. The organic electroluminescent compound of the invention is used as a main material of a luminescent layer in an organic electroluminescent device, can improve the luminous efficiency and the service life, and reduce the driving voltage.

Description

Organic electroluminescent compound and application thereof
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to an organic electroluminescent compound and application thereof.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage direct current drive, full curing, wide viewing angle, light weight, simple composition and process and the like, and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle, low power, 1000 times of response speed of the liquid crystal display, and lower manufacturing cost than the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research of efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The phosphorescent host materials used at present have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts. The single carrier transport ability causes mismatching of electrons and holes in the light emitting layer, resulting in severe roll-off of efficiency and shortened lifetime.
However, materials used in organic electroluminescent devices have room for improvement, and organic electroluminescent materials having superior luminescent properties, longer lifetime, and higher efficiency are urgently desired in the industry. In the process of using a phosphorescent host, the problem of unbalanced carriers of a single host material is solved through the research of the host material, but the performance is not satisfactory, and a new luminescent host material still needs to be developed.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic electroluminescent compound and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic electroluminescent compound having a structure represented by formula I:
Figure BDA0002865734150000011
wherein X1Selected from NR2、CR3R4，
Ring a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, q is 1 or 2 (i.e., ring a is one or two);
ring B is selected from the group consisting of substituted or unsubstituted pyridyl,
R1selected from hydrogen, deuterium, tritium, cyano, nitro, halogen, substituted or unsubstituted C1-C10 straight chain alkyl, substituted or unsubstituted C3-C10 branched chain alkyl, substituted or unsubstituted C2-C10 alkylene, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
Figure BDA0002865734150000021
The dotted line represents the attachment site of the group,
n is an integer of 0 to 2,
R2selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, -L2NAr2Ar3，
R3-R4Each independently selected from substituted or unsubstituted C1-C4 straight chain or branched chain alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, R3-R4Independently exist or are adjacent to each other to form a ring D,
ring D is selected from substituted or unsubstituted fluorenyl,
R5-R6each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, Ar1Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, -L2NAr2Ar3，
L1、L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
Ar2-Ar3each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and m is an integer from 0 to 3 (e.g., 0, 1, 2, or 3, preferably an integer from 1 to 2).
Preferably, the organic electroluminescent compound is a compound having the following structure:
Figure BDA0002865734150000022
wherein the groups are as defined in formula I;
preferably, ring a is a substituted or unsubstituted benzene ring.
Preferably, the organic electroluminescent compound is a compound having the following structure:
Figure BDA0002865734150000031
wherein the groups are as defined in formula I;
preferably, Ar1Or R2Each independently selected from
Figure BDA0002865734150000032
Wherein Z is1-Z20Each independently selected from N or C-RY，
T1Selected from O, S, N-RT1Or CRT2RT3，
RY、RT1、RT2、RT3、R7、R8、R9、R10、R11、R12、R13Each independently selected from hydrogen, deuterium, tritium, cyano, nitro, halogen, substituted or unsubstituted C1-C4 linear or branched alkyl, substituted or unsubstituted C1-C4 linear or branched alkoxy, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl,
substitutionRadical RYAt least 2 substituents which are not linked or adjacent to each other are linked by a chemical bond to form ring E,
R5、R6、R7、R8at least 2 substituents which are not linked or adjacent to each other are chemically bonded to form a ring F,
Z20is selected from the group consisting of O, S,
preferably, ring E is selected from phenyl, pyridyl; more preferably phenyl;
preferably, ring F is selected from phenyl, naphthyl, pyridyl; more preferably a naphthyl group;
preferably, Ar1Or R2Each independently selected from the group consisting of: -L2NAr2Ar3、
Figure BDA0002865734150000033
Figure BDA0002865734150000041
Figure BDA0002865734150000051
Wherein the wavy line represents the attachment site of the group;
RY、RT1、RT2、RT3、R3、R4、R5each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C4 straight or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
RYindependently or adjacently form a ring D, RT2、RT3Independently exist or are adjacent to each other to form a ring E,
the ring D is preferably selected from benzene ring and naphthalene ring, and the ring E is preferably fluorene ring;
preferably, RY、RT1、RT2、RT3、R3、R4、R5、Ar2、Ar3Independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl or any one of the following groups:
Figure BDA0002865734150000052
Figure BDA0002865734150000061
wherein the wavy line represents the attachment site of the group.
Preferably, L1、L2Each independently selected from the group consisting of a single bond, substituted or unsubstituted: phenyl, biphenyl, naphthyl, terphenyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, carbazolyl.
In the present invention, when the group is a substituted group as described above, the substituent is selected from deuterium, halogen, cyano, nitro, unsubstituted or R ' substituted C1-C4 straight chain or linear alkyl, unsubstituted or R ' substituted C6-C20 aryl, unsubstituted or R ' substituted C3-C20 heteroaryl, C6-C20 arylamine;
r' is selected from deuterium, halogen, cyano or nitro.
Preferably, the organic electroluminescent compound is any one of the following compounds:
Figure BDA0002865734150000062
Figure BDA0002865734150000071
Figure BDA0002865734150000081
Figure BDA0002865734150000091
Figure BDA0002865734150000101
Figure BDA0002865734150000111
Figure BDA0002865734150000121
Figure BDA0002865734150000131
Figure BDA0002865734150000141
Figure BDA0002865734150000151
Figure BDA0002865734150000161
Figure BDA0002865734150000171
Figure BDA0002865734150000181
Figure BDA0002865734150000191
the alkyl group in the invention can be any one of a straight chain and a branched chain, and optionally, the alkyl group includes but is not limited to methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl and tert-butyl.
Cycloalkyl groups described herein include, but are not limited to, cyclopropane, cyclobutane, cyclohexane.
The alkenyl group in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds and having 2 to 40 carbon atoms. Examples include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
The aryl groups of the present invention include monocyclic, polycyclic, fused ring aromatic groups, which rings may be interrupted by short nonaromatic units such as methylene. The aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthryl, anthracenyl, indenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, chrysenyl, fused tetraphenyl, fluoranthenyl or spirobifluorenyl.
The heteroaryl groups of the present invention include monocyclic, polycyclic, fused ring groups, and the rings may be interrupted by short nonaromatic units such as methylene, O, S, N. The heteroaryl group is selected from furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl or dihydroacridinyl.
In the present invention, the definition of a group defines a range of carbon numbers that is any integer within the defined range, such as a C6-C30 aryl group, and the number of carbon atoms representing an aryl group can be any integer within the range encompassed by 6-30, such as 6, 8, 10, 15, 20, or 30, and the like.
In the present invention, the preparation route of the organic electroluminescent compound is:
Figure BDA0002865734150000201
Figure BDA0002865734150000211
wherein X is halogen, preferably bromine or chlorine; bpin is pinacol borate, and the other groups are defined as in formula I.
In another aspect, the present invention provides an organic electroluminescent composition comprising any one or a combination of at least two of the organic electroluminescent compounds as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer comprising any one or a combination of at least two of the organic electroluminescent compounds as described above.
Preferably, the organic layer comprises a light-emitting layer comprising any one of or a combination of at least two of the organic electroluminescent compounds as described above.
Preferably, the light-emitting layer comprises a host material and a guest material, and the host material of the light-emitting layer comprises any one of the organic electroluminescent compounds or a combination of at least two of the organic electroluminescent compounds or the organic electroluminescent composition.
Preferably, the guest material includes a phosphorescent dopant.
Preferably, the phosphorescent dopant is a metal complex comprising Ir, Pt, Ni, Au, Os, Re, Rh, Zn, Ag, Fe or W.
In another aspect, the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device comprises at least two organic electroluminescent devices stacked to form a series structure.
In another aspect, the invention provides an optoelectronic product comprising an organic electroluminescent device as described above.
In the present invention, the organic electroluminescent device or the photoelectric product as described above can be applied to optoelectronics, medicine, biotechnology, optical fiber, lighting device, electrophotographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light-emitting field-effect transistor, image sensor, and dye laser.
Compared with the prior art, the invention has the following beneficial effects:
the organic electroluminescent compound of the invention is used as a main material of a luminescent layer in an organic electroluminescent device, can improve the luminous efficiency and the service life, and reduce the driving voltage.
Detailed Description
The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation example 1
Figure BDA0002865734150000221
Synthesis of intermediates 1-2: a 25 ml three-neck bottle is taken, a stirrer and an upper reflux pipe are placed in the bottle, nitrogen is filled in the bottle, raw material 1(1mmol), raw material 2(1mmol), potassium carbonate (1.2mmol), tetrakis (triphenylphosphine) palladium (0.05mmol), toluene (10ml), water (3 ml) are added, the mixture reacts at 60 ℃ for 10 hours under the protection of nitrogen, after the reaction is finished, the mixture is cooled to room temperature, 3 ml of ice water is added for quenching, dichloromethane (10 multiplied by 3 ml) is used for extraction, magnesium sulfate is sequentially added to obtained extract liquid for drying, filtering and spin-drying, and the crude product is purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain intermediate 1-2(0.27 g, 73% yield).
Synthesis of intermediate 2-2: taking a 25 ml double-neck round-bottom bottle, putting a stirrer and an upper reflux pipe, drying, introducing nitrogen, respectively adding an intermediate 1-2(1mmol), triphenylphosphine (2mmol) and 1, 2-dichlorobenzene (10ml), heating at 180 ℃ for reaction for 12 hours, cooling to room temperature after the reaction is finished, concentrating a reaction system, and purifying a crude product by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain an intermediate 2-2(0.23 g, yield 70%).
Synthesis of Compound 2: A25-mL two-necked round-bottomed flask was taken, a stirrer and an upper reflux tube were placed in the flask, nitrogen was introduced after drying, intermediate 2-2(1mmol), raw material 3(1mmol), cesium carbonate (1.5mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.055mmol) were added respectively, toluene was then added, the mixture was refluxed for 12 hours, cooled to room temperature after reaction, the reaction system was filtered and concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain compound 2(0.49 g, yield 80%).
Elemental analysis: c44H30N4Theoretical value: c, 85.97, H, 4.92, N, 9.11, found: c, 86.01, H, 4.90, N, 9.09, HRMS (ESI) M/z (M +): theoretical value: 614.2470, found: 614.2463.
preparation example 2
Figure BDA0002865734150000222
Synthesis of intermediates 1 to 21: in a 25 mL three-necked flask, the starting material 4(1mmol), Boc anhydride (1.1mmol) and tetrahydrofuran (10mL) were charged, nitrogen gas was introduced, and after stirring, 4-dimethylaminopyridine (0.2mmol) was added, the temperature was raised to 70 ℃ to react for 2 hours, and after cooling to room temperature, the solvent was distilled off under reduced pressure, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (vol.%)) to obtain intermediates 1 to 21(0.37g, yield 94%).
Synthesis of intermediates 2 to 21: A25-mL two-necked round-bottomed flask was taken, and a stirrer and an upper reflux tube were placed in the flask, and after drying, nitrogen gas was introduced, and then, 1 to 21(1mmol) as an intermediate, 2 to 2(1mmol) as an intermediate, cesium carbonate (1.8mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.06mmol) were added, followed by addition of toluene, reflux of the mixture for 12 hours, reaction was then cooled to room temperature, the reaction system was filtered and concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain 2 to 21 as an intermediate (0.46 g, yield 71%).
Synthesis of intermediates 3 to 21: taking a 25 ml round-bottom flask, taking the intermediate 2-21(1mmol), adding 15 ml tetrahydrofuran and 1 ml hydrochloric acid, stirring at room temperature, after the reaction is finished, pouring an aqueous solution of sodium bicarbonate, extracting for 5 times by using dichloromethane, and removing the solvent to obtain a product 3-21 for later use.
Synthesis of compound 21: A25-mL two-necked round-bottom flask was placed in a stirrer and an upper reflux tube, nitrogen was introduced after drying, 3-21 parts of the product obtained in the previous step, 5 parts of the raw material (1mmol), cesium carbonate (1.2mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.055mmol) were added, toluene was then added, the mixture was refluxed for 12 hours, cooled to room temperature after reaction, the reaction system was filtered and concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain 21 parts of compound (0.65 g, 83% yield).
Elemental analysis: c55H36N6Theoretical value: c, 84.59, H, 4.65, N, 10.76, found: c, 84.63, H, 4.64, N, 10.73, HRMS (ESI) M/z (M +): theoretical value: 780.3001, found: 780.3008.
preparation example 3
Figure BDA0002865734150000231
Synthesis of intermediates 1 to 42: in a 25 mL three-necked flask, the raw material 6(1mmol), Boc anhydride (1.1mmol) and tetrahydrofuran (10mL) were charged, nitrogen gas was introduced, and after stirring, 4-dimethylaminopyridine (0.2mmol) was added, the temperature was raised to 70 ℃ to react for 2 hours, and after cooling to room temperature, the solvent was distilled off under reduced pressure, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (vol.%)) to obtain intermediates 1 to 42(0.37g, 93% yield).
Synthesis of intermediates 2 to 42: in a 25 ml three-necked flask, intermediate 1-42(1mmol), tetrahydrofuran (10ml) were added, the reaction was cooled to-78 ℃, n-butyllithium (1mmol) was slowly added, followed by addition of 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane (1mmol), the reaction was warmed to room temperature, stirring was continued for 10 hours, after completion of the reaction, quenching was performed with water, the product was washed with water, extracted with ethyl acetate 3 times, the organic layer was dried over anhydrous magnesium sulfate, the organic solvent was removed, and the crude product was separated by column chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to give intermediate 2-42(0.27 g, yield 61%).
Synthesis of intermediates 3-42: in a 25 ml three-necked flask, intermediate 2-42(1mmol), 2-bromo-3-nitropyridine (1mmol), tetrakis (triphenylphosphine) palladium (0.05mmol), tetrabutylammonium bromide (0.05mmol), sodium carbonate (1.5mmol), toluene 10ml, ethanol (2 ml), and water (2 ml) were added, the system was warmed to 80 ℃ and reacted for 12 hours, after completion of the reaction, the system was cooled to room temperature, water was added, ethyl acetate was extracted, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed, and the crude product was separated by column chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain intermediate 3-42(0.29 g, yield 67%).
Synthesis of intermediates 4 to 42: taking a 25 ml double-neck round-bottom bottle, putting a stirrer and an upper reflux pipe, drying, introducing nitrogen, respectively adding an intermediate 3-42(1mmol), triphenylphosphine (2mmol) and 1, 2-dichlorobenzene (10ml), heating at 180 ℃ for reaction for 12 hours, cooling to room temperature after the reaction is finished, concentrating a reaction system, and purifying a crude product by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain an intermediate 4-42(0.27 g, yield 66%).
Synthesis of intermediates 5 to 42: A25-mL two-necked round-bottomed flask was taken, a stirrer and an upper reflux pipe were placed in the flask, nitrogen was introduced after drying, intermediates 4 to 42(1mmol), bromobenzene (1mmol), cesium carbonate (1.2mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.055mmol) were added respectively, toluene was then added, the mixture was refluxed for 12 hours, cooled to room temperature after reaction, the reaction system was filtered and concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain intermediates 5 to 42(0.36 g, yield 75%).
Synthesis of intermediates 6 to 42: taking a 25 ml round-bottom flask, taking the intermediate 5-42(1mmol), adding 10ml tetrahydrofuran and 1 ml hydrochloric acid, stirring at room temperature, after the reaction is finished, pouring an aqueous solution of sodium bicarbonate, extracting for 5 times by using dichloromethane, and removing the solvent to obtain a product 6-42 for later use.
42, synthesis: A25-mL two-necked round-bottom flask was placed in a stirrer and an upper reflux tube, nitrogen was introduced after drying, 6 to 42 parts of the product obtained in the previous step, 7(1mmol) as a raw material, cesium carbonate (1.2mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.055mmol) were added, toluene was then added, the mixture was refluxed for 12 hours, cooled to room temperature after reaction, the reaction system was filtered and concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain 42(0.50 g, 85% yield).
Elemental analysis: c41H25N5Theoretical value: c, 83.79, H, 4.29, N, 11.92, found: c, 83.84, H, 4.27, N, 11.89, HRMS (ESI) M/z (M +): theoretical value: 587.2110, found: 587.2117.
preparation example 4
Figure BDA0002865734150000251
Synthesis of intermediates 1 to 108: the same synthesis as intermediates 5-42, except substituting bromobenzene with starting material 8, gave intermediates 1-108 (71% yield).
Synthesis of intermediates 2 to 108: the difference is that intermediates 1-108 are used to replace intermediates 5-42 to obtain intermediates 2-108.
Synthesis of compound 108: compound 108 was synthesized (0.63 g, 83% yield) with the exception that starting material 9 was used instead of starting material 7 and intermediates 2-108 were used instead of intermediates 6-42.
Element classificationAnd (3) analysis: c53H34N6Theoretical value: c, 84.33, H, 4.54, N, 11.13, found: c, 84.28, H, 4.56, N, 11.16, HRMS (ESI) M/z (M +): theoretical value: 754.2845, found: 754.2853.
preparation example 5
Figure BDA0002865734150000252
Synthesis of intermediates 1 to 73: the same synthesis as intermediates 5-42, except substituting bromobenzene with starting material 12, gave intermediates 1-73 (82% yield).
Synthesis of intermediates 2 to 73: the difference is that the intermediate 1-73 is used to replace the intermediate 5-42 to obtain the intermediate 2-73.
Synthesis of compound 73: synthesis of compound 42 was performed except that starting material 13 was used instead of starting material 7 and intermediates 2-73 were used instead of intermediates 6-42 to give compound 73(0.65 g, 84% yield).
Elemental analysis: c56H37N5Theoretical values are as follows: c, 86.24, H, 4.78, N, 8.98, found: c, 86.28, H, 4.76, N, 8.96, HRMS (ESI) M/z (M +): theoretical value: 779.3049, found: 779.3054.
preparation example 7
Figure BDA0002865734150000261
Synthesis of compound 69: synthesis of Compound 42, except that starting material 7 was replaced with starting material 14, gave Compound 69 (77% yield).
Elemental analysis: c43H25N5S theoretical value: c, 80.23, H, 3.91, N, 10.88, S, 4.98, found: c, 80.29, H, 3.90, N, 10.85, S, 4.96, hrms (esi) M/z (M +): theoretical value: 643.1831, found: 643.1839.
Comparative preparation example 1
Figure BDA0002865734150000262
And (3) synthesizing an intermediate 1-Ref-1: in a 50 ml three-necked flask, under the protection of nitrogen, 15(1mmol) as a raw material, 16(1mmol) as a raw material, 12mmol of potassium carbonate, 20 ml of toluene, 2 ml of water and 0.05mmol of tetrakis (triphenylphosphine) palladium were added, stirred at 100 ℃ for 6 hours, and then cooled to room temperature after reaction. Adding water into the reaction system, extracting by ethyl acetate, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10, vol.) to give intermediate 1-Ref-1(0.24 g, 59% yield).
And (3) synthesizing an intermediate 2-Ref-1: taking a 25 ml double-neck round-bottom bottle, putting a stirrer and an upper reflux pipe, drying, introducing nitrogen, respectively adding an intermediate 1-Ref-1(1mmol), triphenylphosphine (2mmol) and 1, 2-dichlorobenzene (10ml), heating at 180 ℃ for reaction for 12 hours, cooling to room temperature after the reaction is finished, concentrating a reaction system, and purifying a crude product by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain an intermediate 2-Ref-1(0.26 g, yield 68%).
Synthesis of Ref-1: a25 ml two-neck round-bottom flask is taken, a stirrer and an upper reflux pipe are placed in the flask, nitrogen is filled after drying, an intermediate 2-Ref-1(1mmol), a raw material 7(1mmol), cesium carbonate (1.5mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.055mmol) are respectively added, then toluene is added, the mixture is refluxed for 12 hours, after reaction, the mixture is cooled to room temperature, after reaction system filtration, concentration is carried out, and a crude product is subjected to chromatography purification (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain a compound Ref-1(0.47 g, yield 80%).
Elemental analysis: c41H25N5Theoretical value: c, 83.79, H, 4.29, N, 11.92, found: c, 83.84, H, 4.27, N, 11.89, HRMS (ESI) M/z (M +): theoretical value: 587.2110, found: 587.2101.
comparative preparation example 2
Figure BDA0002865734150000271
And (3) synthesizing an intermediate 1-Ref-2: A25-mL three-necked flask was charged with 10(1mmol) as a starting material, 11(1mmol) as a starting material, tetrakis (triphenylphosphine) palladium (0.05mmol), tetrabutylammonium bromide (0.05mmol), sodium carbonate (1.5mmol), toluene (10mL), ethanol (2 mL), water (2 mL), and the system was heated to 80 ℃ to react for 12 hours, after completion of the reaction, the system was cooled to room temperature, water was added, ethyl acetate was extracted, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed, and the crude product was isolated by column chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)), whereby 1-Ref-2 as an intermediate (0.23 g, yield: 64%) was obtained.
And (3) synthesizing an intermediate 2-Ref-2: taking a 25 ml double-neck round-bottom bottle, putting a stirrer and an upper reflux pipe, drying, introducing nitrogen, respectively adding an intermediate 1-Ref-2(1mmol), triphenylphosphine (2mmol) and 1, 2-dichlorobenzene (10ml), heating at 180 ℃ for reaction for 12 hours, cooling to room temperature after the reaction is finished, concentrating a reaction system, and purifying a crude product by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain an intermediate 2-Ref-2(0.23 g, yield 68%).
Synthesis of Ref-2: a25-milliliter two-neck round-bottom flask is taken and placed into a stirrer and an upper connecting reflux pipe, nitrogen is introduced after drying, an intermediate 2-Ref-2(1mmol), a raw material 5(1mmol), cesium carbonate (1.5mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol) and 2-dicyclohexylphosphorus-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.055mmol) are respectively added, then toluene is added, the mixture is refluxed for 12 hours, the reaction system is cooled to room temperature after reaction, the reaction system is concentrated after filtration, and a crude product is purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain a compound Ref-2(0.44 g, 78% yield).
Elemental analysis: c39H27N5Theoretical values are as follows: c, 82.81, H, 4.81, N, 12.38, found: c, 82.85, H, 4.82, N, 12.33, HRMS (ESI) M/z (M +): theoretical values are as follows: 565.2266, found: 565.2273.
device embodiments
Subsequent device examples 1 to 5 (see table 1) provide for the use of the materials of the invention in OLEDs.
OLEDs have essentially the following layer structure: a base (indium tin oxide (ITO) coated glass substrate)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/emissive layer (EML)/Electron Transport Layer (ETL)/optional Electron Injection Layer (EIL), and finally a cathode. The cathode 8 is made of a mixed material of metal Mg and Ag, wherein the mass ratio of the metal Mg to the Ag is 9:1, and the thickness of the metal Mg to the Ag is 80 nm. The host materials in the light-emitting layer are the compounds 2, 21, 42, 69, 73 and 108 prepared by the invention and the comparative example compounds Ref-1, Ref-2 and Ref-3, and are specifically shown in Table 1.
The precise structure of the OLED can be seen in table 1. The materials required to make an OLED are shown in the following formula.
Figure BDA0002865734150000281
The preparation of the organic electroluminescent device comprises the following steps:
1) substrate cleaning:
carrying out ultrasonic treatment on the glass substrate 1 coated with the ITO transparent electrode in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are that glycol solvent is less than or equal to 10wt percent, and triethanolamine is less than or equal to 1wt percent), washing in deionized water, and carrying out ultrasonic treatment in a water-based solvent system under the conditions of acetone: ultrasonically removing oil in an ethanol mixed solvent (volume ratio is 1: 1), baking in a clean environment until water is completely removed, and then cleaning by using ultraviolet light and ozone;
2) evaporation:
placing the glass substrate 1 with the anode 2 in a vacuum chamber, and vacuumizing to 1 × 10-6To 2X 10-4Pa, vacuum evaporating a hole injection layer 3 material on the anode layer film in a co-evaporation mode, wherein the evaporation thickness is 10 nm;
3) evaporating a hole transport layer 4 on the hole injection layer 3, wherein the thickness of the evaporated film is 80 nm;
4) evaporating a luminescent layer 5 on the hole transport layer 4, and evaporating a luminescent host material and an object material in vacuum in a co-evaporation mode, wherein the total film thickness is 30 nm;
5) vacuum-evaporating an electron transport layer 6 on the light-emitting layer 5 to a total thickness of 30 nm;
6) an electron injection layer 7 is evaporated on the electron transport layer 6 in vacuum, and the total film thickness of the evaporation is 1 nm;
7) a cathode 8 was deposited on the electron injection layer 7 to a total thickness of 80 nm.
TABLE 1
Figure BDA0002865734150000291
Figure BDA0002865734150000301
Testing the performance of the device:
the instrument comprises the following steps: the characteristics of the device such as current, voltage, brightness, luminescence spectrum and the like are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
and (3) testing conditions are as follows: the current density is 20 mA/cm2Room temperature.
And (3) testing the service life: the time (in hours) was recorded when the device brightness dropped to 98% of the original brightness.
The device performance test results are shown in table 2:
TABLE 2
Drive voltage (V) Current efficiency (Cd/A) Life (h) CIE x CIE y
1 4.7 22 187 0.668 0.326
2 4.6 25 177 0.670 0.324
3 4.9 29 174 0.665 0.329
4 4.8 21 150 0.670 0.321
5 4.8 27 165 0.661 0.326
6 4.7 28 176 0.664 0.329
Comparative example 1 4.9 15 89 0.668 0.327
Comparative example 2 4.8 16 102 0.667 0.326
Comparison 3 4.9 18 76 0.663 0.325
It can be seen from table 2 that the naphthoindolizinozolinazole structure has appropriate LUMO and HOMO energy levels, and can limit carriers in the light-emitting layer to prevent electron leakage, and meanwhile, the twisted molecular structure prevents molecules from being stacked, so that hole mobility is reduced, electron mobility is balanced, light-emitting efficiency is improved, and service life is prolonged.
The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent compounds and their applications, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must be implemented by means of the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (10)

1. An organic electroluminescent compound having a structure represented by formula I:
Figure FDA0002865734140000011
wherein X1Selected from NR2、CR3R4，
Ring A is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, q is 1 or 2;
ring B is selected from the group consisting of substituted or unsubstituted pyridyl,
R1selected from hydrogen, deuterium, tritium, cyano, nitro, halogen, substituted or unsubstituted C1-C10 straight-chain alkyl, substituted or unsubstituted C3-C10 branched-chain alkyl, substituted or unsubstituted C2-C10 alkylene, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
Figure FDA0002865734140000012
The dotted line represents the attachment site of the group,
n is an integer of 0 to 2,
R2selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, -L2NAr2Ar3，
R3-R4Each independently selected from substituted or unsubstituted C1-C4 straight chain or branched chain alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, R3-R4Independently exist or are adjacent to each other to form a ring D,
ring D is selected from a substituted or unsubstituted fluorenyl group,
R5-R6each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
Ar1selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, -L2NAr2Ar3，
L1、L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
Ar2-Ar3each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
m is an integer of 0 to 3.
2. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is a compound having the following structure:
Figure FDA0002865734140000021
wherein the groups are as defined in formula I;
preferably, ring a is a substituted or unsubstituted benzene ring.
3. The organic electroluminescent compound according to claim 1 or 2, wherein the organic electroluminescent compound is a compound having the following structure:
Figure FDA0002865734140000031
wherein the groups are as defined in formula I;
preferably, Ar1Or R2Each independently selected from
Figure FDA0002865734140000032
Wherein Z is1-Z20Each independently selected from N or C-RY，
T1Selected from O, S, N-RT1Or CRT2RT3，
RY、RT1、RT2、RT3、R7、R8、R9、R10、R11、R12、R13Each independently selected from hydrogen, deuterium, tritium, cyano, nitro, halogen, substituted or unsubstituted C1-C4 linear or branched alkyl, substituted or unsubstituted C1-C4 linear or branched alkoxy, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl,
substituent RYAt least 2 substituents which are not linked or adjacent to each other are linked by a chemical bond to form ring E,
R5、R6、R7、R8at least 2 substituents which are not linked or adjacent to each other are linked by a chemical bond to form a ring F,
Z20is selected from the group consisting of O, S,
preferably, ring E is selected from phenyl, pyridyl; more preferably phenyl;
preferably, ring F is selected from phenyl, naphthyl, pyridyl; more preferably a naphthyl group;
preferably, Ar1Or R2Each independently selected from the group consisting of: -L2NAr2Ar3、
Figure FDA0002865734140000041
Figure FDA0002865734140000051
Wherein the wavy line represents the attachment site of the group;
RY、RT1、RT2、RT3、R3、R4、R5each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C4 straight or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
RYindependently or adjacently form a ring D, RT2、RT3Independently exist or are adjacent to each other to form a ring E,
the ring D is preferably selected from benzene ring and naphthalene ring, and the ring E is preferably selected from fluorene ring.
4. The organic electroluminescent compound according to any one of claims 1 to 3, wherein R isY、RT1、RT2、RT3、R3、R4、R5、Ar2、Ar3Independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl or any one of the following groups:
Figure FDA0002865734140000052
Figure FDA0002865734140000061
wherein the wavy line represents the attachment site of the group.
5. The organic electroluminescent compound according to any one of claims 1 to 4, wherein L is1、L2Each independently selected from the group consisting of a single bond, substituted or unsubstituted: phenyl, biphenyl, naphthyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, carbazolyl;
preferably, when the group is a substituted group, the substituent is selected from deuterium, halogen, cyano, nitro, unsubstituted or R ' substituted C1-C4 straight chain or straight chain alkyl, unsubstituted or R ' substituted C6-C20 aryl, unsubstituted or R ' substituted C3-C20 heteroaryl, and C6-C20 arylamine;
r' is selected from deuterium, halogen, cyano or nitro.
6. The organic electroluminescent compound according to any one of claims 1 to 5, wherein the organic electroluminescent compound is any one of the following compounds:
Figure FDA0002865734140000071
Figure FDA0002865734140000081
Figure FDA0002865734140000091
Figure FDA0002865734140000101
Figure FDA0002865734140000111
Figure FDA0002865734140000121
Figure FDA0002865734140000131
Figure FDA0002865734140000141
Figure FDA0002865734140000151
Figure FDA0002865734140000161
Figure FDA0002865734140000171
Figure FDA0002865734140000181
Figure FDA0002865734140000191
Figure FDA0002865734140000201
Figure FDA0002865734140000211
Figure FDA0002865734140000221
7. an organic electroluminescent composition comprising any one of the organic electroluminescent compounds according to any one of claims 1 to 6 or a combination of at least two thereof.
8. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, the organic layer comprising any one or a combination of at least two of the organic electroluminescent compounds as claimed in any one of claims 1 to 6;
preferably, the organic layer comprises a light-emitting layer comprising any one of the organic electroluminescent compounds as claimed in any one of claims 1 to 6 or a combination of at least two thereof;
preferably, the light-emitting layer comprises a host material and a guest material, the light-emitting layer host material comprises any one of the organic electroluminescent compounds according to any one of claims 1 to 6 or a combination of at least two of the organic electroluminescent compounds or the organic electroluminescent composition according to claim 7;
preferably, the guest material comprises a phosphorescent dopant;
preferably, the phosphorescent dopant is a metal complex comprising Ir, Pt, Ni, Au, Os, Re, Rh, Zn, Ag, Fe or W.
9. An organic electroluminescent device, wherein at least two organic electroluminescent devices as claimed in claim 8 are stacked to form a series structure.
10. An optoelectronic product comprising the organic electroluminescent device according to claim 8.
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Cited By (1)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110386946A (en) * 2018-04-19 2019-10-29 江苏三月光电科技有限公司 It is a kind of using ketone as compound of core and the preparation method and application thereof
CN112094169A (en) * 2019-06-18 2020-12-18 北京鼎材科技有限公司 Organic electroluminescent material and application thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110386946A (en) * 2018-04-19 2019-10-29 江苏三月光电科技有限公司 It is a kind of using ketone as compound of core and the preparation method and application thereof
CN112094169A (en) * 2019-06-18 2020-12-18 北京鼎材科技有限公司 Organic electroluminescent material and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115925714A (en) * 2022-12-30 2023-04-07 宁波卢米蓝新材料有限公司 Organic electroluminescent compounds and use thereof

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