Organic compound containing polysubstituted carbazole and organic electroluminescent device thereof

Abstract

The invention relates to an organic compound containing polysubstituted carbazole. The organic compound can be used as a phosphorescent host material to be applied to a light-emitting layer of an OLED device, and by taking carbazole as a parent nucleus and introducing substitution of a plurality of specific groups on carbazole, a molecular conjugated system is effectively prolonged, carrier migration localization is avoided, and the carrier mobility is effectively improved, so that the light-emitting efficiency of the device is improved.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent device materials, in particular to an organic compound containing multi-substituted carbazole and an organic electroluminescent device thereof. Background Art

[0002] Organic electroluminescent devices (OLEDs) are considered to be the new flat-panel display technology with the greatest development potential. They have many advantages, such as all-solid-state, active luminescence, high contrast, ultra-thinness, low power consumption, no viewing angle limitation, fast response speed, wide operating temperature range, easy realization of flexible display and 3D display, etc. OLEDs also have excellent shock resistance, potential low manufacturing cost and environmentally friendly design, etc., and are the fastest growing new flat-panel display technology in the future.

[0003] OLED adopts a sandwich structure, that is, the organic layer is sandwiched between the anode and cathode on both sides. The organic layer is divided into a hole transport layer, an electron transport layer, a light-emitting layer (including a main material and a guest material), a hole blocking layer and an electron blocking layer according to the different photoelectric properties of various materials. Its working principle is: when a certain magnitude of external bias is applied to the device, electrons and holes are injected from the cathode and anode and enter the electron transport layer and the hole transport layer respectively. Then, driven by the external electric field, the charge continues to be transferred to the interface between the electron transport layer and the hole transport layer. Because there is an energy level difference between the molecules of the two materials at the interface, charge accumulation occurs at the interface. When electrons and holes overcome the energy barrier and enter the light-emitting layer to recombine to form excitons, the excitons are unstable, and molecular luminescence is achieved through radiation attenuation.

[0004] The OLED light-emitting layer generally includes a light-emitting material (guest) and a host material. The guest material is evenly dispersed in the host material, which can simultaneously improve the photoluminescence efficiency of the light-emitting layer and reduce exciton quenching. In the light-emitting layer, the content of the guest material is generally low, so the dominant host material determines the physical properties of the light-emitting layer to a large extent and directly affects the performance of the light-emitting device, especially the driving voltage and power efficiency of the device. Therefore, the selection of the host material is very important.

[0005] In order to enhance the luminous efficiency, driving voltage and life characteristics of OLED devices, various host materials for organic electroluminescent devices have been proposed, but there are still technical problems with luminous efficiency and device life. Therefore, it is necessary to continue to develop new host materials to further improve the performance of organic electroluminescent devices. Summary of the invention

[0006] The object of the present invention is to provide an organic compound containing polysubstituted carbazole, which is used as a main material in an organic electroluminescent device to improve the photoelectric performance of the device.

[0007] To achieve the purpose of the present invention, the technical solution is as follows:

[0008] A polysubstituted carbazole organic compound having a structure as shown in the general formula (I):

[0009] (I);

[0010] Where: Ar 3 ,Ar 4 ,Ar 5 Independently selected from the group (A):

[0011] (A)

[0012] n is selected from 0 or 1; m is selected from 0 or 1; and n+m≥1;

[0013] And Ar 3 ,Ar 4 ,Ar 5 At least one of the following is selected from group (B):

[0014] (B)

[0015] R1 and R2 are independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 10 carbon atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by the above groups;

[0016] Ar 1 independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms;

[0017] Ar 2 independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms;

[0018] The term "substituted or unsubstituted" means that the group is not substituted or is substituted with one or more substituents R. 0 Substitution, the R 0 Each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by the above groups;

[0019] * indicates the attachment site.

[0020] The present invention also provides a mixture, which comprises the above-mentioned polysubstituted carbazole organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials or host materials.

[0021] The present invention also provides a composition, which comprises the above-mentioned polysubstituted carbazole-containing organic compound or the above-mentioned mixture, and at least one organic solvent.

[0022] The present invention also provides an organic electroluminescent device, which comprises at least one functional layer, wherein the at least one functional layer comprises the above-mentioned multi-substituted carbazole-containing organic compound or mixture.

[0023] Compared with the prior art, the present invention has the following beneficial effects:

[0024] The polysubstituted carbazole organic compound of the present invention can be used as a phosphorescent host material in the light-emitting layer of an OLED device. By using carbazole as a parent core and introducing multiple specific groups to replace carbazole, on the one hand, the molecular conjugation system is effectively extended, the localization of carrier migration is avoided, and the carrier mobility is effectively improved, thereby improving the luminous efficiency of the device. On the other hand, the polysubstituted carbazole organic compound has higher thermal stability and film-forming properties when evaporating the device, which is conducive to improving the life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0026] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to an embodiment of the device of the present invention.

[0027] Among them, 1-substrate; 2-anode; 3-hole injection layer; 4-first hole transport layer; 5-second hole transport layer; 6-light-emitting layer; 7-electron transport layer; 8-electron injection layer; 9-cathode layer. DETAILED DESCRIPTION

[0028] For ease of understanding of the present invention, the present invention will be described more fully below with reference to relevant embodiments. Preferred embodiments of the present invention are provided in the embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0029] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art of the present invention. The terms used herein in the specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0030] In the present invention, composition and printing ink, or ink have the same meaning and can be interchanged.

[0031] In the present invention, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0032] In the present invention, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0033] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0034] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0035] In the present invention, the "number of ring atoms" refers to the number of atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0036] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms" refers to aromatic groups containing 6 to 20 carbon atoms, preferably substituted or unsubstituted aromatic groups having 6 to 14 ring atoms, further selected from substituted or unsubstituted aromatic groups having 6 to 10 ring atoms, and the hydrogen atoms on the aromatic group are optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof.

[0037] "Heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 20 ring atoms" means a heteroaryl having 5 to 20 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl having 6 to 10 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, triazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoline, Oxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzothiophenyl, benzofuranyl, indolyl, carbazolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, o-naphthyl, quinoxalinyl, phenanthridinyl, primary pyridinyl, quinazolinyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0038] In the present invention, "alkyl" may refer to a linear, branched or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 10, or 1 to 6, or 1 to 4. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, and the like.

[0039] In the present invention, "*" connected to a single bond indicates a connection or fusion site.

[0040] In the present invention, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0041] In the present invention, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are used as the fusion site.

[0042] In the present invention, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other. , 6 R on the benzene ring 1 May be the same as or different from each other.

[0043] In the present invention, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0044] The “combination thereof”, “any combination thereof”, “combination of groups”, “combination” and the like used in the present invention include all suitable combinations of any two or more items in the listed groups.

[0045] In the present invention, “further”, “furthermore”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0046] In the present invention, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel solutions of "yes" or "no". If multiple "options" appear in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction, each "optional" is independent.

[0047] In the present invention, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0048] The present invention relates to a polysubstituted carbazole organic compound having a structure as shown in the general formula (I):

[0049] (I)

[0050] Where: Ar 3 ,Ar 4 ,Ar 5 Independently selected from the group (A):

[0051] (A)

[0052] n is selected from 0 or 1; m is selected from 0 or 1; and n+m≥1;

[0053] And Ar 3 ,Ar 4 ,Ar 5 At least one of the following is selected from group (B):

[0054] (B)

[0055] R1 and R2 are independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 10 carbon atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by the above groups;

[0056] Ar 1 independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms;

[0057] Ar 2 independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms;

[0058] The term "substituted or unsubstituted" means that the group is not substituted or is substituted with one or more substituents R. 0 Substitution, the R 0Each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by the above groups;

[0059] * indicates the attachment site.

[0060] Furthermore, the Ar 2 Independently selected from a substituted or unsubstituted aromatic group having 6 to 14 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0061] Furthermore, the Ar 2 Independently selected from the following groups:

[0062] ;

[0063] in:

[0064] Each occurrence of X is independently selected from C, CR3 or N;

[0065] R3 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by the above groups;

[0066] When X is a fusion site, X is selected from C.

[0067] Preferably, the Ar 2 Selected from the following groups:

[0068]

[0069] Wherein: # represents a fusion site, and the fusion site is selected from C atoms.

[0070] According to the present invention, a polysubstituted carbazole organic compound has a structure as shown in any one of the general formulas (II-1) to (II-5):

[0071] .

[0072] Further, in the general formula (II-1)-(II-5), X is selected from CR3; preferably, each occurrence of R3 is independently selected from -H, -D, or an alkyl group having 1 to 10 carbon atoms. More preferably, each occurrence of R3 is independently selected from -H, -D, methyl, isopropyl, tert-butyl, methyl substituted by one or more -D, isopropyl substituted by one or more -D, or tert-butyl substituted by one or more -D.

[0073] In one embodiment, the Ar 1 is independently selected from substituted or unsubstituted N-containing heteroaromatic groups having 5 to 14 ring atoms. 1 Selected from any of the following groups:

[0074] ;

[0075] Wherein: R4 is independently selected from unsubstituted or R * substituted aromatic group having 6 to 20 carbon atoms, or unsubstituted or replaced by R * Substituted heteroaromatic groups having 5 to 20 ring atoms;

[0076] The R * Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, -CN, an alkyl group having 1-6 carbon atoms, an aromatic group having 6-10 carbon atoms, or a heteroaromatic group having 6-10 ring atoms, or a group formed by a combination of the above groups.

[0077] Preferably, the R * Each occurrence of -D is independently selected from -D, an alkyl group having 1 to 6 carbon atoms, a phenyl group, a naphthyl group, or a group formed by a combination of the foregoing groups.

[0078] Further, each occurrence of R4 is independently selected from unsubstituted or replaced by R * Substituted phenyl, unsubstituted or R * Substituted naphthyl, unsubstituted or R * Substituted phenylbenzene, unsubstituted or R * Substituted biphenyl, unsubstituted or R * substituted binaphthyl; said R * Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, -CN, or an alkyl group having 1 to 6 carbon atoms.

[0079] In a specific embodiment, the Ar 1 Selected from any of the following groups, but not limited to:

[0080] .

[0081] In one embodiment, the group (A) is selected from any of the following structures:

[0082] .

[0083] Furthermore, the group (B) is selected from the following structures:

[0084] .

[0085] In one embodiment, Ar 3 ,Ar 4 ,Ar 5 Only one of them is selected from group (B), and the remaining two are selected from .

[0086] In one embodiment, Ar 3 Selected from or ;Ar 4 ,Ar 5 Selected from .

[0087] In another embodiment, Ar 4 Selected from or ; Ar 3 ,Ar 5 Selected from .

[0088] In another embodiment, Ar 5 Selected from or ; Ar 3 ,Ar 4 Selected from .

[0089] In a specific embodiment, the Each time it appears, select or .

[0090] Further, R1 and R2 are independently selected from -H, -D, -F, -CF3, -Cl, -Br, -I, -CN, an alkyl group having 1 to 6 carbon atoms, an unsubstituted or substituted R # Substituted phenyl, unsubstituted or R # Substituted biphenyl, unsubstituted or R # substituted pyridyl, unsubstituted or R # substituted pyrimidinyl, unsubstituted or R # Substituted naphthyl, or a group formed by the above groups; said R # Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, -CN, or an alkyl group having 1 to 6 carbon atoms.

[0091] Furthermore, the Each time it appears, select , .

[0092] In a specific embodiment, the polysubstituted carbazole organic compound according to the present invention is selected from the following structures but not limited thereto:

[0093] .

[0094] In one embodiment, the polysubstituted carbazole organic compound according to the present invention can be used as a host material in a light-emitting layer.

[0095] The present invention also provides a mixture, the mixture comprising the above-mentioned polysubstituted carbazole-containing organic compound and at least one organic functional material; the organic functional material is preferably selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials or host materials. Preferably, the organic functional material is selected from electron transport materials, hole transport materials, luminescent host materials or luminescent guest materials.

[0096] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode and at least one functional layer located between the cathode and the anode, wherein the at least one functional layer comprises the above-mentioned multi-substituted carbazole organic compound.

[0097] Preferably, the at least one functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a guest material, and the host material comprises the polysubstituted carbazole organic compound as described above.

[0098] The organic electroluminescent device according to the present invention comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked in sequence from bottom to top; the light-emitting layer comprises the polysubstituted carbazole organic compound as described above.

[0099] The present invention also relates to the application of organic electroluminescent devices in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

[0100] The present invention is described below in conjunction with examples of compound preparation and device characterization, but the present invention is not limited to the following examples. It should be understood that the attached claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0101] Synthesis Example of Organic Compounds Containing Polysubstituted Carbazole

[0102] Synthesis Example 1: Synthesis of Compound (2)

[0103]

[0104] Synthesis of compound 2-1:

[0105] Accurately weigh 2-nitrobenzeneboric acid (16.7g, 0.1mol) and compound 3,4-dichloro-2-fluorobromobenzene (24.4g, 0.1mol) and add them to a 500ml three-necked flask, then add 200ml of anhydrous toluene and 50ml of potassium carbonate (4mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (1.15g 1mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 10h, cool to room temperature after the raw materials react completely, distill the reaction solution under reduced pressure to remove toluene, then add dichloromethane to extract three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then separate with a mixed solvent column chromatography of petroleum ether and dichloromethane to obtain about 15.73g of compound 2-1, with a yield of 54.8%. MS: 286.75.

[0106] Synthesis of compound 2-2:

[0107] Accurately weigh compound 2-1 (14.3g, 50mmol) and phenylboronic acid (12.2g, 100mol) and add them to a 500ml three-necked flask, then add 150ml of anhydrous toluene and 60ml of potassium carbonate (4mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (2.3g 2mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 24h, cool to room temperature after the raw materials are basically reacted, remove toluene from the reaction solution by vacuum distillation, then add dichloromethane to extract three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then separate with a mixed solvent column chromatography of petroleum ether and dichloromethane to obtain about 12.39g of compound 2-2, with a yield of 66.9%. MS: 370.11.

[0108] Synthesis of compound 2-3:

[0109] Accurately weigh compound 2-2 (11.1 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask, add about 150 mL of anhydrous DMF, replace nitrogen three times and heat to 120 ° C for 6 hours. After the raw materials are completely reacted, cool to room temperature, pour the reaction solution into 500 ml of water, precipitate a large amount of solid, filter, rinse the filter cake with 50 ml of deionized water and 50 ml of ethanol in turn, then slurry with a mixed solvent of petroleum ether and dichloromethane at room temperature for 30 minutes, filter, and obtain about 11.16 g of compound 2-3, with a yield of 72.0%. MS: 516.49.

[0110] Synthesis of compound 2-4:

[0111] Accurately weigh compound 2-3 (10.9 g, 21 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask, add about 120 mL of o-dichlorobenzene, replace nitrogen three times, and heat to 180 ° C for 4 hours. After the raw materials react completely, cool to 120 ° C, remove o-dichlorobenzene by vacuum distillation of the reaction solution, slurry the residue with 200 ml of petroleum ether for 30 min, filter, and obtain a solid product. Add 100 ml of toluene and heat to dissolve, filter the silica gel hot, and then add 100 ml of anhydrous ethanol to the filtrate to precipitate a large amount of solids, filter, and rinse the filter cake with 50 ml of ethanol and dry to obtain about 8.37 g of compound 2-4 with a yield of 82.3%. MS: 484.35.

[0112] Synthesis of compound (2):

[0113] Accurately weigh compound 2-4 (7.3 g, 15 mmol), sodium tert-butoxide (3 g 30 mmol) and compound 2-5 (5.7 g, 15 mmol) and add them to a 250 mL three-necked flask, then add 100 ml of anhydrous toluene to the reaction flask, add X-Phos (428.4 mg 90 mmol) and Pd(dba)2 (259 mg, 0.45 mmol) under nitrogen protection, replace nitrogen three times, and then heat to reflux for 4 hours. After the raw materials react completely, cool to 120 ° C, distill the reaction solution under reduced pressure to remove toluene, separate the residue with 300 ml of dichloromethane and 100 ml of water, extract the aqueous phase with dichloromethane three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, distill the filtrate under reduced pressure to remove the solvent, and dissolve the residue with 100 ml of toluene by heating and cooling to precipitate and recrystallize to obtain about 8.57 g of compound (2) with a yield of 69.0%. MS:827.61.

[0114] Synthesis Example 2: Synthesis of Compound (12)

[0115]

[0116] Synthesis of compound 12-1:

[0117] Accurately weigh 2-nitrobenzeneboric acid (16.7g, 0.1mol) and compound 2,4-dichloro-3-fluorobromobenzene (24.4g, 0.1mol) and add them to a 500ml three-necked flask, then add 200ml of anhydrous toluene and 50ml of potassium carbonate (4mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (1.15g 1mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 10h, cool to room temperature after the raw materials react completely, distill the reaction solution under reduced pressure to remove toluene, then add dichloromethane to extract three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then separate with a mixed solvent column chromatography of petroleum ether and dichloromethane to obtain about 14.87g of compound 12-1, with a yield of 51.9%. MS: 286.53.

[0118] Synthesis of compound 12-2:

[0119] Accurately weigh compound 12-1 (14.3g, 50mmol) and phenylboronic acid (12.2g, 100mol) and add them to a 500ml three-necked flask, then add 150ml of anhydrous toluene and 60ml of potassium carbonate (4mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (2.3g 2mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 24h, cool to room temperature after the raw materials are basically reacted, remove toluene from the reaction solution by vacuum distillation, then add dichloromethane to extract three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then separate with a mixed solvent column chromatography of petroleum ether and dichloromethane to obtain about 11.82g of compound 12-2, with a yield of 63.9%. MS: 369.78.

[0120] Synthesis of compound 12-3:

[0121] Accurately weigh compound 12-2 (11.1 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask, add about 150 mL of anhydrous DMF, replace nitrogen three times and heat to 120 ° C for 6 hours. After the raw materials are completely reacted, cool to room temperature, pour the reaction solution into 500 ml of water, precipitate a large amount of solid, filter, rinse the filter cake with 50 ml of deionized water and 50 ml of ethanol in turn, then slurry with a mixed solvent of petroleum ether and dichloromethane at room temperature for 30 minutes, filter, and obtain about 11.7 g of compound 12-3, with a yield of 75.4%. MS: 517.39.

[0122] Synthesis of compound 12-4:

[0123] Accurately weigh compound 12-3 (10.9 g, 21 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask, add about 120 mL of o-dichlorobenzene, replace nitrogen three times, and heat to 180 ° C for 4 hours. The raw materials reacted completely, cooled to 120 ° C, and the reaction solution was distilled under reduced pressure to remove o-dichlorobenzene. The residue was slurried with 200 ml of petroleum ether for 30 minutes and filtered to obtain a solid product. 100 ml of toluene was added to heat and dissolve, and the silica gel was filtered hot. Then 100 ml of anhydrous ethanol was added to the filtrate to precipitate a large amount of solids, which were filtered and dried to obtain about 8.02 g of compound 12-4 with a yield of 78.9%. MS: 484.21.

[0124] Synthesis of compound (12):

[0125] Accurately weigh compound 12-4 (7.3 g, 15 mmol), sodium tert-butoxide (3 g 30 mmol) and compound 2-5 (5.7 g, 15 mmol) and add them to a 250 mL three-necked flask, then add 100 ml of anhydrous toluene to the reaction flask, add X-Phos (428.4 mg 90 mmol) and Pd(dba)2 (259 mg, 0.45 mmol) under nitrogen protection, replace nitrogen three times, and then heat to reflux for 4 hours. After the raw materials react completely, cool to 120 ° C, distill the reaction solution under reduced pressure to remove toluene, separate the residue with 300 ml of dichloromethane and 100 ml of water, extract the aqueous phase with dichloromethane three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, distill the filtrate under reduced pressure to remove the solvent, and dissolve the residue with 100 ml of toluene by heating and cooling to precipitate and recrystallize to obtain about 8.14 g of compound (12) with a yield of 65.5%. MS:828.45.

[0126] Synthesis Example 3: Synthesis of Compound (14)

[0127]

[0128] Synthesis of compound (14):

[0129] Accurately weigh compound 12-4 (7.3 g, 15 mmol), sodium tert-butoxide (2.3 g 30 mmol) and compound 14-1 (5.16 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (12) to obtain about 8.76 g of compound (14) with a yield of 73.7%. MS: 792.42.

[0130] Synthesis Example 4: Synthesis of Compound (18)

[0131]

[0132] Synthesis of compound (18):

[0133] Accurately weigh compound 12-4 (7.3 g, 15 mmol), sodium tert-butoxide (3 g 30 mmol) and compound 18-1 (3.61 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (12) to obtain about 6.89 g of compound (18) with a yield of 66.7%. MS: 689.12.

[0134] Synthesis Example 5: Synthesis of Compound (21)

[0135]

[0136] Synthesis of compound 21-1:

[0137] Accurately weigh 2-nitrobenzeneboric acid (16.7 g, 0.1 mol) and compound 2,3-dichloro-4-bromofluorobenzene (24.4 g, 0.1 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-1 to obtain about 16.81 g of compound 21-1 with a yield of 58.1%. MS: 286.39.

[0138] Synthesis of compound 21-2:

[0139] Accurately weigh compound 21-1 (14.3 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them to a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-2 to obtain about 13.55 g of compound 21-2, with a yield of 73.3%. MS: 369.52.

[0140] Synthesis of compound 21-3:

[0141] Accurately weigh compound 21-2 (11.1 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-3 to obtain about 12.36 g of compound 21-3 with a yield of 79.7%. MS: 516.97.

[0142] Synthesis of compound 21-4:

[0143] Accurately weigh compound 21-3 (10.9 g, 21 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-4 to obtain about 7.68 g of compound 21-4 with a yield of 75.4%. MS: 485.04.

[0144] Synthesis of compound (21):

[0145] Accurately weigh compound 21-4 (7.3 g, 15 mmol), sodium tert-butoxide (3 g 30 mmol) and compound 21-5 (4.8 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (12) to obtain about 8.93 g of compound (21) with a yield of 77.8%. MS: 765.63.

[0146] Synthesis Example 6: Synthesis of Compound (34)

[0147]

[0148] Synthesis of compound 34-1:

[0149] Accurately weigh 3-nitro-2-naphthaleneboronic acid (21.7 g, 0.1 mol) and compound 2,3-dichloro-4-bromofluorobenzene (24.4 g, 0.1 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-1 to obtain about 17.95 g of compound 34-1, with a yield of 53.3%. MS: 336.80.

[0150] Synthesis of compound 34-2:

[0151] Accurately weigh compound 34-1 (16.8 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them to a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-2 to obtain about 12.83 g of compound 34-2 with a yield of 61.1%. MS: 419.82.

[0152] Synthesis of compound 34-3:

[0153] Accurately weigh compound 34-2 (12.6 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-3 to obtain about 11.62 g of compound 34-3 with a yield of 68.4%. MS: 566.45.

[0154] Synthesis of compound 34-4:

[0155] Accurately weigh compound 34-3 (11.3 g, 20 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-4 to obtain about 8.28 g of compound 34-4 with a yield of 77.5%. MS: 534.01.

[0156] Synthesis of compound (34):

[0157] Accurately weigh compound 34-4 (8 g, 15 mmol), sodium tert-butoxide (3 g, 30 mmol) and compound 21-5 (4.8 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (12) to obtain about 8.79 g of compound (34) with a yield of 71.8%. MS: 816.56.

[0158] Synthesis Example 7: Synthesis of Compound (36)

[0159]

[0160] Synthesis of compound 36-1:

[0161] Accurately weigh 2-nitro-1-naphthaleneboronic acid (21.7 g, 0.1 mol) and compound 2,4-dichloro-3-fluorobromobenzene (24.4 g, 0.1 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-1 to obtain about 21.42 g of compound 36-1, with a yield of 63.8%. MS: 336.07.

[0162] Synthesis of compound 36-2:

[0163] Accurately weigh compound 36-1 (16.8 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-2 to obtain about 15.18 g of compound 36-2 with a yield of 72.4%. MS: 419.18.

[0164] Synthesis of compound 36-3:

[0165] Accurately weigh compound 36-2 (12.6 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-3 to obtain about 12.86 g of compound 36-3 with a yield of 75.6%. MS: 567.33.

[0166] Synthesis of compound 36-4:

[0167] Accurately weigh compound 36-3 (11.3 g, 20 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-4 to obtain about 9.01 g of compound 36-4 with a yield of 84.2%. MS: 534.82.

[0168] Synthesis of compound (36):

[0169] Accurately weigh compound 36-4 (8 g, 15 mmol), sodium tert-butoxide (3 g, 30 mmol) and compound 36-5 (4 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (12) to obtain about 7.74 g of compound (36) with a yield of 67.4%. MS: 765.58.

[0170] Synthesis Example 8: Synthesis of Compound (39)

[0171]

[0172] Synthesis of compound 39-1:

[0173] Accurately weigh 3-nitro-2-naphthaleneboronic acid (21.7 g, 0.1 mol) and compound 2,4-dichloro-3-fluorobromobenzene (24.4 g, 0.1 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-1 to obtain about 19.73 g of compound 39-1, with a yield of 58.8%. MS: 335.46.

[0174] Synthesis of compound 39-2:

[0175] Accurately weigh compound 39-1 (16.8 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them to a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-2 to obtain about 17.41 g of compound 39-2 with a yield of 82.9%. MS: 420.05.

[0176] Synthesis of compound 39-3:

[0177] Accurately weigh compound 39-2 (12.6 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-3 to obtain about 11.69 g of compound 39-3 with a yield of 68.7%. MS: 567.14.

[0178] Synthesis of compound 39-4:

[0179] Accurately weigh compound 39-3 (11.3 g, 20 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 12-4 to obtain about 8.37 g of compound 39-4 with a yield of 78.2%. MS: 535.18.

[0180] Synthesis of compound (39):

[0181] Accurately weigh compound 39-4 (8 g, 15 mmol), sodium tert-butoxide (3 g, 30 mmol) and compound 14-1 (5.2 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (12) to obtain about 9.24 g of compound (39) with a yield of 73.2%. MS: 841.81.

[0182] Synthesis Example 9: Synthesis of Compound (49)

[0183]

[0184] Synthesis of compound 49-1:

[0185] Accurately weigh 1-nitro-2-naphthaleneboronic acid (21.7 g, 0.1 mol) and compound 3,4-dichloro-2-fluorobromobenzene (24.4 g, 0.1 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 2-1 to obtain about 17.28 g of compound 49-1 with a yield of 51.4%. MS: 336.14.

[0186] Synthesis of compound 49-2:

[0187] Accurately weigh compound 49-1 (16.8 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 2-2 to obtain about 12.94 g of compound 49-2 with a yield of 61.7%. MS: 419.26.

[0188] Synthesis of compound 49-3:

[0189] Accurately weigh compound 49-2 (12.6 g, 30 mmol), carbazole (5 g 30 mmol) and cesium carbonate (14.6 g, 45 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 2-3 to obtain about 11.37 g of compound 49-3 with a yield of 66.9%. MS: 566.28.

[0190] Synthesis of compound 49-4:

[0191] Accurately weigh compound 49-3 (11.3 g, 20 mmol) and triphenylphosphine (26 g, 100 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 2-4 to obtain about 8.69 g of compound 49-4 with a yield of 81.3%. MS: 534.36.

[0192] Synthesis of compound (49):

[0193] Accurately weigh compound 49-4 (8 g, 15 mmol), sodium tert-butoxide (2.98 g 30 mmol) and compound 49-5 (4.8 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (2) to obtain about 8.27 g of compound (49) with a yield of 67.8%. MS: 815.64.

[0194] Synthesis Example 10: Synthesis of Compound (55)

[0195]

[0196] Synthesis of compound 55-1:

[0197] Accurately weigh o-nitrobenzeneboric acid (16.7g, 0.1mol) and compound 1.2-dibromo-3-chloro-4-iodobenzene (39.6g, 0.1mol) and add them to a 500ml three-necked flask, then add 200ml of anhydrous toluene and 50ml of potassium carbonate (4mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (1.15g, 1mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 10h, cool to room temperature after the raw materials react completely, distill the reaction solution under reduced pressure to remove toluene, then add dichloromethane to extract three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then separate with a mixed solvent column chromatography of petroleum ether and dichloromethane to obtain about 19.85g of compound 55-1, with a yield of 50.7%. MS: 391.18.

[0198] Synthesis of compound 55-2:

[0199] Accurately weigh compound 55-1 (19.6 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them to a 500 ml three-necked flask, then add 150 ml of anhydrous toluene and 60 ml of potassium carbonate (4 mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (2.3 g 2 mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 24 hours, cool to room temperature after the raw materials are basically reacted, remove toluene from the reaction solution by vacuum distillation, then add dichloromethane to extract three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then separate with a mixed solvent column chromatography of petroleum ether and dichloromethane to obtain about 11.05 g of compound 55-2, with a yield of 57.2%. MS: 386.54.

[0200] Synthesis of compound 55-3:

[0201] Accurately weigh compound 55-2 (9.7 g, 25 mmol) and triphenylphosphine (32.7 g, 125 mmol) and add them to a 250 mL three-necked flask, add about 120 mL of o-dichlorobenzene, replace nitrogen three times, and heat to 180 ° C for 4 hours. The raw materials reacted completely, cooled to 120 ° C, and the reaction solution was distilled under reduced pressure to remove o-dichlorobenzene. The residue was slurried with 200 ml of petroleum ether for 30 minutes and filtered to obtain a large amount of solid. 100 ml of toluene was added and heated to dissolve, and the silica gel was filtered hot. Then 100 ml of anhydrous ethanol was added to the filtrate to precipitate a large amount of solid, which was filtered and the filter cake was rinsed with 50 ml of ethanol and dried to obtain about 7.12 g of compound 55-3 with a yield of 80.6%. MS: 353.41.

[0202] Synthesis of compound 55-4:

[0203] Accurately weigh compound 55-3 (7 g, 20 mmol) and 4-(9H-carbazole-9-yl)phenylboronic acid (5.7 g, 20 mmol) and add them to a 500 ml three-necked flask, then add 200 ml of anhydrous toluene and 50 ml of potassium carbonate (4 mol / L) aqueous solution to the reaction flask, add tetrakistriphenylphosphine palladium (1.15 g 1 mmol) under nitrogen protection, replace nitrogen three times, heat and reflux for 10 hours, cool to room temperature after the raw materials react completely, remove toluene by vacuum distillation of the reaction solution, then add dichloromethane for extraction three times, combine the organic phases, wash with saturated brine, dry with anhydrous sodium sulfate, filter, concentrate the filtrate to remove the solvent, and then recrystallize from toluene to obtain about 7.91 g of compound 55-4, with a yield of 70.4%. MS: 561.42.

[0204] Synthesis of compound (55):

[0205] Compound 55-4 (6.7 g, 12 mmol), sodium tert-butoxide (2.3 g, 24 mmol) and compound 18-1 (2.9 g, 12 mmol) were accurately weighed and added to a 250 mL three-necked flask, and then 100 ml of anhydrous toluene was added to the reaction flask. X-Phos (342.72 mg, 72 mmol) and Pd(dba)2 (207 mg, 0.36 mmol) were added under nitrogen protection to replace nitrogen three times, and then the temperature was raised to reflux for reaction for 4 hours. After the raw materials reacted completely, the temperature was lowered to 120°C, and the reaction solution was distilled under reduced pressure to remove toluene. The residue was separated by 300 ml of dichloromethane and 100 ml of water. The aqueous phase was extracted three times with dichloromethane, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was distilled under reduced pressure to remove the solvent. The residue was dissolved by heating with 100 ml of toluene, cooled and precipitated, and recrystallized to obtain about 6.37 g of compound (55) with a yield of 69.4%. MS:765.18.

[0206] Synthesis Example 11: Synthesis of Compound (58)

[0207]

[0208] Synthesis of compound 58-1

[0209] Accurately weigh o-nitrobenzeneboric acid (16.7 g, 0.1 mol) and compound 1.3-dibromo-2-chloro-4-iodobenzene (39.6 g, 0.1 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 55-1 to obtain about 22.38 g of compound 58-1; the yield is 57.1%. MS: 392.05.

[0210] Synthesis of compound 58-2

[0211] Accurately weigh compound 58-1 (19.6 g, 50 mmol) and phenylboronic acid (12.2 g, 100 mol) and add them into a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 55-2 to obtain about 13.44 g of compound 58-2; the yield is 69.6%. MS: 386.02.

[0212] Synthesis of compound 58-3

[0213] Accurately weigh compound 58-2 (9.7 g, 25 mmol) and triphenylphosphine (32.7 g, 125 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 55-3 to obtain about 7.69 g of compound 58-3; the yield is 86.8%. MS: 354.16.

[0214] Synthesis of compound 58-4

[0215] Accurately weigh compound 58-3 (7 g, 20 mmol) and 4-(9H-carbazole-9-yl)phenylboronic acid (5.7 g, 20 mmol) and add them to a 500 ml three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound 55-4 to obtain about 9.58 g of compound 58-4; the yield is 85.4%. MS: 561.14.

[0216] Synthesis of compound (58):

[0217] Accurately weigh compound 58-4 (8.4 g, 15 mmol), sodium tert-butoxide (2.98 g 30 mmol) and compound 14-1 (5.2 g, 15 mmol) and add them to a 250 mL three-necked flask. The subsequent synthesis steps refer to the synthesis steps of compound (55) to obtain about 7.86 g of compound (58); the yield is 60.4%. MS: 867.96.

[0218] Preparation of OLED devices:

[0219] The following is an example of preparing an OLED device using the compound of the present application. The specific device structure, preparation process and device performance test experimental operation are as follows:

[0220] Device Example 1

[0221] like Figure 1 As shown, the device structure is shown, and the device preparation method includes the following steps:

[0222] a. Cleaning of ITO conductive glass substrate: Provide an ITO conductive glass substrate, clean the substrate with a cleaning agent, and then perform ultraviolet ozone treatment. The cleaning agent may include but is not limited to one or more of chloroform, acetone or isopropyl alcohol.

[0223] b. Preparation of hole injection layer 3: The ITO conductive glass substrate was moved into a vacuum vapor deposition device and placed in a high vacuum (1×10 -6 HATCN was evaporated by resistance heating evaporation at 100 mbar to form a hole injection layer with a thickness of 10 nm.

[0224] c. Preparation of the first hole transport layer 4: HTM-1 was evaporated on the hole injection layer 3 to form a first hole transport layer 4 with a thickness of 60 nm.

[0225] d. Preparation of the second hole transport layer 5: HTM-2 was evaporated on the first hole transport layer 4 to form a second hole transport layer 5 with a thickness of 10 nm.

[0226] e. Preparation of the light-emitting layer 6: On the second hole transport layer 5, the host material and the guest material are co-evaporated at a mass ratio of 95:5 to form a light-emitting layer 6 with a thickness of 25 nm. The host material is selected from the polysubstituted carbazole organic compound (2), and the guest material is selected from EM1.

[0227] f. Preparation of electron transport layer 7: Electron transport materials ET and Liq (ET to Liq mass ratio of 5:5) are deposited on the light emitting layer 6 by vacuum evaporation to form an electron transport layer 7 with a thickness of 30 nm;

[0228] g. Forming the electron injection layer 8: The electron injection layer 8 is formed on the electron transport layer 7 by vacuum evaporation of an electron injection material Liq, with a thickness of 1 nm.

[0229] h. Forming the cathode layer 9: Al is deposited on the electron injection layer 8 by vacuum evaporation to obtain an Al cathode layer 9 with a thickness of 100 nm.

[0230] i. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0231]

[0232] Device Examples 2-11:

[0233] The preparation methods of device examples 2-11 are the same as those of device example 1, except that: the main material in the light-emitting layer 6 is selected differently. Specifically, the main material containing polysubstituted carbazole organic compound (2) in the light-emitting layer 6 of device example 1 is replaced by polysubstituted carbazole organic compound (12), polysubstituted carbazole organic compound (14), polysubstituted carbazole organic compound (18), polysubstituted carbazole organic compound (21), polysubstituted carbazole organic compound (34), polysubstituted carbazole organic compound (36), polysubstituted carbazole organic compound (39), polysubstituted carbazole organic compound (49), polysubstituted carbazole organic compound (55) and polysubstituted carbazole organic compound (58). See Table 1 for details.

[0234] Device Comparison Example 1:

[0235] The preparation method of device comparative example 1 is the same as that of device example 1, except that the main material of the light-emitting layer 6 containing the polysubstituted carbazole organic compound (2) is replaced by the organic compound Ref

[0236]

[0237] The current-voltage (JV) characteristics of the above-mentioned OLED devices were characterized by a characterization device, and the LT95 lifetime and luminous efficiency were recorded at the same time. LT95 represents the time required for the device brightness to decay to 95% of the initial brightness. The device lifetime LT95 in device comparative example 1 was recorded as 1, and the ratios of the corresponding indicators of device examples 1-11 and device comparative example 1 were calculated respectively, as shown in Table 1.

[0238] Table 1

[0239]

[0240] It can be seen from the results in Table 1 that the polysubstituted carbazole organic compound provided by the present invention is used as a phosphorescent host material in an organic electroluminescent device. Compared with the device comparison example 1, both the luminous efficiency and the life span are significantly improved, indicating that the polysubstituted carbazole organic compound provided by the present invention is a class of materials with excellent performance and has a good application prospect.

[0241] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A polysubstituted carbazole organic compound, characterized in that: The polysubstituted carbazole organic compound has a structure as shown in the general formula (I): （I）； Where: Ar 3 ,Ar 4 ,Ar 5 Independently selected from the group (A): （A） n is selected from 0 or 1; m is selected from 0 or 1; and n+m≥1; And Ar 3 ,Ar 4 ,Ar 5 At least one of the following is selected from group (B): （B） R1 and R2 are independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 10 carbon atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by the above groups; Ar 1 independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms; Ar 2 independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms; The term "substituted or unsubstituted" means that the group is not substituted or is substituted with one or more substituents R. 0 Substitution, the R 0 Each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by the above groups; * indicates the attachment site.

2. The polysubstituted carbazole organic compound according to claim 1, characterized in that: The Ar 2 Independently selected from any of the following groups: ； in: Each occurrence of X is independently selected from C, CR3 or N; R3 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by the above groups; When X is a fusion site, X is selected from C.

3. The polysubstituted carbazole organic compound according to claim 2, characterized in that: The general formula (I) is selected from any one of the structures shown in general formulas (II-1) to (II-5): 。 4. The polysubstituted carbazole organic compound according to any one of claims 1 to 3, characterized in that: The Ar 1 Selected from any of the following groups: ； wherein each occurrence of R4 is independently selected from unsubstituted or replaced by R * Substituted aromatic groups having 6 to 20 carbon atoms, or unsubstituted or replaced by R * Substituted heteroaromatic groups having 5 to 20 ring atoms; The R * Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, -CN, an alkyl group having 1-6 carbon atoms, an aromatic group having 6-10 carbon atoms, or a heteroaromatic group having 6-10 ring atoms, or a group formed by a combination of the above groups.

5. The polysubstituted carbazole organic compound according to claim 1, characterized in that: The group (A) is selected from any of the following structures: ； The group (B) is selected from the following structures: 。 6. The polysubstituted carbazole organic compound according to claim 5, characterized in that: When Ar 3 Selected from or When Ar 4 ,Ar 5 Selected from ; When Ar 4 Selected from or When Ar 3 ,Ar 5 Selected from ; When Ar 5 Selected from or When Ar 3 ,Ar 4 Selected from .

7. The polysubstituted carbazole organic compound according to claim 1, characterized in that: The polysubstituted carbazole organic compound is selected from any of the following structures: 。 8. A mixture, characterized in that: The mixture comprises a polysubstituted carbazole organic compound as described in any one of claims 1 to 7, and at least one organic functional material, wherein the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent guest material or a host material.

9. A composition, characterized in that: The composition comprises the polysubstituted carbazole-containing organic compound according to any one of claims 1 to 7 or the mixture according to claim 8, and at least one organic solvent.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises at least one functional layer, and the at least one functional layer comprises the polysubstituted carbazole-containing organic compound according to any one of claims 1 to 7 or the mixture according to claim 8.

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