Silicon-containing compounds and their applications in organic light-emitting devices

Abstract

The present invention relates to the technical field of organic photoelectric material preparation, and specifically to silicon-containing compounds and their application in organic light-emitting devices. The silicon-containing compounds provided by the present invention have good electron and hole receiving capabilities, can improve the energy transfer performance and thermal stability between the host and the guest; at the same time, the introduction of large sterically hindered fluorene / silicon heterofluorene / germanium heterofluorene groups can weaken the interaction between luminescent molecules; using it as a functional layer, especially as a light-emitting layer in an organic electroluminescent device, its current efficiency is improved, the lighting voltage is reduced, and the life of the device is also greatly improved.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric material preparation, and in particular to silicon-containing compounds and applications thereof in organic light-emitting devices. Background Art

[0002] With the development of multimedia technology and the improvement of information requirements, the requirements for panel display performance are getting higher and higher. Among them, OLED has a series of advantages such as autonomous luminescence, low-voltage DC drive, full curing, wide viewing angle, rich colors, etc., and has attracted widespread attention for its potential application in the new generation of display and lighting technology, and its application prospects are very broad. Organic electroluminescent devices are spontaneous luminescent devices. The mechanism of OLED luminescence is that under the action of an external electric field, electrons and holes are injected from the positive and negative electrodes respectively, and then migrate, recombine and decay in the organic material to produce luminescence. The typical structure of OLED includes one or more functional layers of cathode layer, anode layer, electron injection layer, electron transport layer, hole blocking layer, hole transport layer, hole injection layer and light-emitting layer. Although the research progress of organic electroluminescence is very rapid, there are still many problems to be solved. For example, high-efficiency and long-life blue light materials have always been a problem to be solved by technicians in this field. Summary of the invention

[0003] The purpose of the present invention is to provide a silicon-containing compound and its application in an organic light-emitting device in view of the deficiencies of the prior art. The present invention effectively inhibits the interaction between luminescent molecules by introducing a large steric hindrance group of triphenylsilicon. The prepared silicon-containing compound has good electron and hole receiving ability, can improve the energy transfer performance between the host and the guest, and reduce the concentration of high-energy excitons in the light-emitting layer, thereby realizing a high-efficiency and long-life blue light material. Therefore, this type of silicon-containing compound has important applications in organic light-emitting devices.

[0004] In order to achieve the purpose of the present invention, the technical solution of the present invention is as follows:

[0005] According to one or more embodiments, the present invention provides a silicon-containing compound having a structure represented by the following formula (1):

[0006] ;

[0007] wherein R1-R3 are each independently selected from hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted arylamine; and X is selected from CR a R b 、SiR c R d or GeR e R f; R a -R f Each is independently selected from hydrogen, deuterium, deuterated or undeuterated C1~C24 alkyl, C3~C24 cycloalkyl; X1-X5 are each independently selected from CR4 or N; R4 is each independently selected from hydrogen, deuterium, C1~C24 alkyl, substituted or unsubstituted C3~C24 cycloalkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C3~C30 alkylsilyl, or can be connected with adjacent substituents to form a ring.

[0008] When there is substitution, the substituent is selected from any one or more of deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, and C6-C30 aryl.

[0009] According to one or more embodiments, the R a -R f Each is independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane and cyclohexane, and any hydrogen atom may be replaced by deuterium.

[0010] According to one or more embodiments, R1-R3 are each independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, 1,1,4,4-tetramethylcyclohexane, substituted or unsubstituted diphenylamine; when substituted, the substituent is selected from any one or more of deuterium, tert-butyl, 1,1,4,4-tetramethylcyclohexane, and phenyl.

[0011] Preferably, R2 is selected from hydrogen, deuterium, tert-butyl, substituted or unsubstituted diphenylamine; the substituent is selected from any one or more of deuterium, tert-butyl, 1,1,4,4-tetramethylcyclohexane, and phenyl.

[0012] According to one or more embodiments, X1-X5 are each independently CR4, or at least one is selected from N; R4 can be independently selected from any one or more of hydrogen, deuterium, tert-butyl, phenyl, tert-butylphenyl, 1,1,4,4-tetramethylcyclohexane, and trimethylsilyl each time it appears.

[0013] Preferably, when any one of X1-X5 is selected from N and the others are selected from CR4; R4 is independently selected from any one or more of hydrogen, deuterium, tert-butyl, phenyl, and tert-butylphenyl each time it occurs.

[0014] Preferably, X1-X5 are each independently CR4, and R4, when it appears each time, can be independently selected from any one or more of hydrogen, deuterium, tert-butyl, phenyl, tert-butylphenyl, 1,1,4,4-tetramethylcyclohexane, and trimethylsilyl.

[0015] At least one hydrogen in the compound shown in formula (I) may be substituted by deuterium, tritium, cyano or halogen.

[0016] According to one or more embodiments, the silicon-containing compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

[0017]

[0018] According to one or more embodiments, the present invention also provides use of the silicon-containing compound having the general structure shown in formula (I) above in the preparation of electronic devices.

[0019] Furthermore, the electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0020] According to one or more embodiments, the present invention further provides an organic electroluminescent device, which includes a cathode, an anode and an organic functional layer therebetween; the organic functional layer includes a silicon-containing compound having a general structure as shown in formula (I) above.

[0021] Furthermore, the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a silicon-containing compound having a general structure as shown in the above formula (I), wherein the mass percentage of the silicon-containing compound is 0.1%-50%.

[0022] According to one or more embodiments, the present invention also provides an organic photoelectric device, comprising a first electrode; a second electrode facing the first electrode; and a light-emitting material layer disposed between the first electrode and the second electrode, wherein the light-emitting material layer comprises a silicon-containing compound having a general structure as shown in formula (I) above. For example, the silicon-containing compound can be included in the light-emitting material layer as a guest material or a dopant.

[0023] The present invention also provides a composition, which comprises a silicon-containing compound having a general structure as shown in the above formula (I).

[0024] The present invention also provides a preparation, which comprises a silicon-containing compound having a general structure as shown in the above formula (I) or a composition as described above and at least one solvent. The solvent is not particularly limited, and can be used, for example, unsaturated hydrocarbon solvents, halogenated saturated hydrocarbon solvents, halogenated unsaturated hydrocarbon solvents, ether solvents or ester solvents well known to those skilled in the art; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetralin, n-butylbenzene, sec-butylbenzene or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, hexyl chloride, bromohexane, chlorocyclohexane or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; the ester solvent is an alkyl benzoate.

[0025] The present invention also provides a display or lighting device, wherein the device comprises one or more of the organic electroluminescent devices described above.

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] The silicon-containing compounds involved in the present invention all have good thermal stability. By introducing fluorene / silicon heterofluorene / germanium heterofluorene groups and triphenylsilicon large steric hindrance groups, the interaction between luminescent molecules can be effectively suppressed, thereby improving the efficiency of the device. The silicon-containing compounds involved in the present invention have good electron and hole receiving capabilities, and can improve the energy transfer performance between the host and the guest. Specifically, the organic electroluminescent device made using the silicon-containing compound of the present invention as an organic functional layer, especially as a light-emitting layer, has improved current efficiency, reduced lighting voltage, and greatly improved device life, indicating that after most electrons and holes recombine, energy is effectively transferred to the silicon-containing compound, thereby achieving high luminous efficiency. DETAILED DESCRIPTION

[0028] The content of the present invention is described in detail below. The description of the constituent elements recorded below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. By referring to the following specific embodiments and the examples contained therein, the present disclosure can be more easily understood. Before disclosing and describing the compounds, devices and / or methods of the present invention, it should be understood that, unless otherwise stated, it is not limited to specific synthetic methods or specific reagents, because this can be varied. It should also be understood that the terms used in the present invention are only used to describe specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or test, exemplary methods and materials are now described.

[0029] The term "alkyl" as used herein refers to a monovalent alkyl group having 1 to 24 carbon atoms, preferably 1 to 14 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, etc.

[0030] The "cycloalkyl" of the present invention refers to a cyclic alkyl group having 3 to 24 carbon atoms and a monocyclic or polycyclic condensed ring, preferably 3 to 14 carbon atoms, which can be substituted by 1 to 3 alkyl groups at will. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexane, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, methylcyclohexane, etc., or polycyclic structures such as adamantyl, etc.

[0031] The "aryl" of the present invention refers to an unsaturated aromatic carbon ring having 6-30 carbon atoms and having a monocyclic (such as phenyl) or polycyclic condensation (such as naphthyl or anthracenyl), preferably having 6-18 carbon atoms, more preferably 1-12 carbon atoms. Preferred aryl groups include phenyl, biphenyl, naphthyl, phenanthrenyl, terphenyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 1-3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocyclic, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy.

[0032] The "heteroaryl" mentioned in the present invention refers to a general term for a group having 6-30 carbon atoms and one or more aromatic carbon atoms in the aromatic group are replaced by a heteroatom, preferably 6-18 carbon atoms, and the heteroatom includes but is not limited to oxygen (O), sulfur (S) or nitrogen (N), silicon (Si) or germanium (Ge) atoms. The heteroaryl group can be a monocyclic heteroaryl group or a condensed ring heteroaryl group. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furanyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0033] The substitution in the present invention may be by a single bond or by fusion.

[0034] As used in the specification and the appended claims, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes a mixture of two or more components.

[0035] Unless otherwise stated, all commercial reagents involved in the following experiments were used directly after purchase.

[0036] In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures (Ph is phenyl):

[0037]

[0038] In a preferred embodiment of the present invention, the hole injection layer contained in the OLED device of the present invention. The preferred hole injection layer material of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:

[0039]

[0040] In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but it does not mean that the present invention is limited to the following structures:

[0041]

[0042] The preparation method of the silicon-containing compound, i.e., the guest material, and the luminescent properties of the device are explained in detail in conjunction with the following examples.

[0043] The OLED device of the present invention contains a host material, which can be selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures:

[0044]

[0045] Example 1 Synthesis of Compound 1

[0046]

[0047] (1) Synthesis of Compound 1-3:

[0048] Compound 1-1 (260 mg, 1 mmoL) and compound 1-2 (225 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 24 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:3, to obtain product 1-3 (210 mg, yield 59%). Mass spectrum m / z, theoretical value 357.25; measured value M+H: 358.27;

[0049] (2) Synthesis of Compound 1-6:

[0050] Compound 1-4 (209 mg, 1 mmoL) and compound 1-5 (268 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 48 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:5, to obtain product 1-6 (166 mg, yield 42%). Mass spectrum m / z, theoretical value 397.19; measured value M+H: 398.21;

[0051] (3) Synthesis of Compound 1-8:

[0052] At -78 °C, BuLi (0.5 mL, 1 mmoL, 2M in hexane) was slowly added to a solution of compound 1-7 (396 mg, 1 mmoL) in anhydrous ether (50 mL). After 3 hours of reaction, triphenylsilyl chloride (294 mg, 1 mmoL) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, and then the temperature was raised to 80 °C for 6 hours. After cooling to room temperature, 1 mL of ice water was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:9, to obtain product 1-8 (226 mg, yield 43%). Mass spectrum m / z, theoretical value 525.92; measured value M+H: 526.94;

[0053] (4) Synthesis of Compound 1-9:

[0054] Compound 1-8 (528 mg, 1 mmoL) and compound 1-3 (357 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 48 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:4, to obtain product 1-9 (213 mg, yield 26%). Mass spectrum m / z, theoretical value 803.24; measured value M+H: 804.26;

[0055] (5) Synthesis of Compound 1-10:

[0056] Compound 1-9 (803 mg, 1 mmoL) and compound 1-6 (397 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:7, to obtain product 1-10 (233 mg, yield 21%). Mass spectrum m / z, theoretical value 1120.50; measured value M+H: 1121.52;

[0057] (6) Synthesis of compound 1:

[0058] Under nitrogen atmosphere and zero temperature, tert-butyl lithium (1.25 mL, 1.6 M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compound 1-10 (986 mg, 1 mmoL) in tert-butylbenzene (100 mL). After the system reacted at 60 °C for 4 hours, the temperature was lowered to -50 °C, and then BBr3 (494 mg, 2 mmoL) was added. After reacting at room temperature for 1 hour, N,N-diisopropylethylamine (259 mg, 2 mmoL) was added. The temperature was then raised to 120 °C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:8, to obtain product 1 (245 mg, yield 22%). Mass spectrum m / z, theoretical value 1094.52; measured value M+H: 1095.54.

[0059] Example 2: Synthesis of Compound 3

[0060] Compound 3 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1205.53; measured value M+H: 1206.55.

[0061] Example 3: Synthesis of Compound 6

[0062] Compound 6 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1211.57; measured value M+H: 1212.59.

[0063] Example 4: Synthesis of Compound 12

[0064] Compound 12 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1227.55; measured value M+H: 1228.58.

[0065] Example 5: Synthesis of Compound 18

[0066] Compound 18 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 29%. Mass spectrum m / z, theoretical value 1273.49; measured value M+H: 1274.51.

[0067] Example 6: Synthesis of Compound 19

[0068] Compound 19 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1039.45; measured value M+H: 1040.47.

[0069] Example 7: Synthesis of Compound 30

[0070] Compound 30 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1261.59; measured value M+H: 1262.61.

[0071] Example 8: Synthesis of Compound 36

[0072] Compound 36 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1166.44; measured value M+H: 1167.46.

[0073] Example 9: Synthesis of Compound 43

[0074] Compound 43 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1110.50; measured value M+H: 1111.52.

[0075] Example 10: Synthesis of Compound 45

[0076] Compound 45 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1277.57; measured value M+H: 1278.59.

[0077] Example 11: Synthesis of Compound 59

[0078] Compound 59 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1247.48; measured value M+H: 1248.50.

[0079] Example 12: Synthesis of Compound 62

[0080] Compound 62 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1191.42; measured value M+H: 1192.44.

[0081] Example 13: Synthesis of Compound 66

[0082] Compound 66 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1259.58; measured value M+H: 1260.60.

[0083] Example 14: Synthesis of Compound 69

[0084] Compound 69 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1259.58; measured value M+H: 1260.61.

[0085] Example 15: Synthesis of Compound 70

[0086] Compound 70 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1120.54; measured value M+H: 1121.56.

[0087] Example 16: Synthesis of Compound 75

[0088] Compound 75 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1259.58; measured value M+H: 1260.61.

[0089] Example 17: Synthesis of Compound 78

[0090] Compound 78 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 30%. Mass spectrum m / z, theoretical value 1273.59; measured value M+H: 1274.61.

[0091] Example 18: Synthesis of Compound 79

[0092] Compound 79 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 29%. Mass spectrum m / z, theoretical value 1134.55; measured value M+H: 1135.58.

[0093] Example 19: Synthesis of Compound 83

[0094] Compound 83 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1185.51; measured value M+H: 1186.53.

[0095] Example 20: Synthesis of Compound 87

[0096] Compound 87 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1221.51; measured value M+H: 1222.53.

[0097] Example 21: Synthesis of Compound 88

[0098] Compound 88 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1126.47; measured value M+H: 1127.49.

[0099] Example 22: Synthesis of Compound 92

[0100] Compound 92 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1295.67; measured value M+H: 1296.69.

[0101] Example 23: Synthesis of Compound 96

[0102] Compound 96 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1289.63; measured value M+H: 1290.66.

[0103] Example 24: Synthesis of Compound 100

[0104] Compound 100 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 30%. Mass spectrum m / z, theoretical value 1210.55; measured value M+H: 1211.58.

[0105] Example 25: Synthesis of Compound 103

[0106] Compound 103 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1104.57; measured value M+H: 1105.59.

[0107] Example 26: Synthesis of Compound 107

[0108] Compound 107 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1226.53; measured value M+H: 1227.55.

[0109] Example 27: Synthesis of Compound 117

[0110] Compound 117 was prepared by referring to the preparation method of compound 1 in Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1272.47; measured value M+H: 1273.50.

[0111] Fabrication of OLED devices:

[0112] As a reference preparation method for a device embodiment, the present invention evaporates a p-doped material on the surface of an ITO glass with a light-emitting area of ​​2 mm×2 mm or on an anode, or co-evaporates the p-doped material with a hole transport material at a concentration of 1% to 50% to form a 5-100 nm hole injection layer (HIL), forms a 5-200 nm hole transport layer (HTL) on the hole injection layer, and then co-evaporates a host material and a silicon-containing compound (guest material) prepared by the present invention on the hole transport layer at a volume ratio of 3:97 to form a 10-100 nm light-emitting layer (EML), and finally co-evaporates to form a 35 nm electron transport layer (ETL), and then evaporates 70 nm of cathode Al, thereby manufacturing an organic electroluminescent diode.

[0113] In a preferred specific embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: glass containing ITO is used as the anode, and HIL is sequentially evaporated to be HT-4:P-3 (95:5, v / v%) with a thickness of 10 nanometers; HTL is HT-4 with a thickness of 90 nanometers; EBL is HT-7 with a thickness of 10 nanometers, and EML is the main material (H-3): the silicon-containing compound 1 (97:3, v / v%) provided by the present invention has a thickness of 35 nanometers, and ETL is ET-4:LiQ (50:50, v / v%) with a thickness of 35 nanometers, and then cathode Al is evaporated to be 70 nanometers to prepare an organic electroluminescent diode, which is recorded as Application Example 1.

[0114] Referring to the device structure provided in Application Example 1, the silicon-containing compounds listed in Table 1 were selected as the implementation objects to replace the silicon-containing compound 1, and the silicon-containing compounds were co-evaporated with the host compound at a volume ratio of 3:97 to form a light-emitting layer to prepare an organic electroluminescent diode, which was recorded as Application Example 2 to Application Example 27 and Comparative Example 1. The current efficiency, voltage, life and other characteristics of the device embodiments and comparative examples prepared above were tested by standard methods, and the device light-emitting characteristic data are shown in Table 1.

[0115] The chemical structure of compound BN-1 in Comparative Example 1 is as follows:

[0116]

[0117] Table 1. Device luminescence characteristics data table

[0118]

[0119] As can be seen from Table 1, the compounds of the present invention are used as light-emitting layer materials to prepare electronic devices, which have higher current efficiency and lifespan while reducing the driving voltage. Compared with Comparative Example 1, Application Examples 1 to 27 all show good device performance in terms of current efficiency and lifespan, and the improvement in the performance of each device is achieved based on the better electron transmission ability of the silicon-containing compound material of the present invention. This shows that the silicon-containing compound provided by the present invention has certain commercial application value.

[0120] The above description is only a preferred specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can make equivalent replacements or changes according to the technical scheme and inventive concept of the present invention within the technical scope disclosed by the present invention, which should be covered by the protection scope of the present invention.

Claims

1. A silicon-containing compound, characterized in that The silicon-containing compound has a general structure as shown in the following formula (I): In formula (I), R1 and R3 are independently selected from hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl; R2 is independently selected from substituted or unsubstituted diphenylamine; X is selected from SiR c R d or GeR e R f ; R c -R f Each is independently selected from hydrogen, deuterium, deuterated or undeuterated C1~C24 alkyl, C3~C24 cycloalkyl; X1-X5 are each independently selected from CR4 or N; R4 is each independently selected from hydrogen, deuterium, C1~C24 alkyl, substituted or unsubstituted C3~C24 cycloalkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C3~C30 alkylsilyl; when containing substitution, the substituent is selected from any one or more of deuterium, C1~C24 alkyl, C3~C24 cycloalkyl, C6~C30 aryl.

2. The silicon-containing compound according to claim 1, characterized in that The R c -R f Each is independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane and cyclohexane.

3. The silicon-containing compound according to claim 1, characterized in that The R1 and R3 are each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, and 1,1,4,4-tetramethylcyclohexane.

4. The silicon-containing compound according to claim 1, characterized in that Each occurrence of R4 can be independently selected from any one or more of hydrogen, deuterium, tert-butyl, phenyl, tert-butylphenyl, 1,1,4,4-tetramethylcyclohexyl, and trimethylsilyl.

5. A silicon-containing compound, characterized in that: The silicon-containing compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

6. Use of the silicon-containing compound according to any one of claims 1 to 5 in the preparation of an organic electroluminescent device.

7. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the silicon-containing compound as claimed in any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 7, comprising a cathode, an anode and an organic functional layer therebetween; characterized in that: The organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises the silicon-containing compound according to any one of claims 1 to 5.

9. An organic photoelectric device, comprising a first electrode, a second electrode facing the first electrode, and a light-emitting material layer disposed between the first electrode and the second electrode; characterized in that: The luminescent material layer contains the silicon-containing compound as claimed in any one of claims 1 to 5.

10. A composition, characterized in that The composition comprises the silicon-containing compound according to any one of claims 1 to 5.

11. A preparation, characterized in that The preparation comprises the silicon-containing compound according to any one of claims 1 to 5 and at least one solvent.

12. A display or lighting device, characterized in that: The device comprises one or more of the organic electroluminescent devices according to claim 7.

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