A boron-nitrogen compound having a polybasic condensed ring, an OLED having the compound, and an organic light-emitting device

Abstract

The present application relates to the technical field of organic photoelectric material preparation, and particularly relates to a boron-nitrogen compound with a multi-membered ring, an OLED with the compound and an organic light-emitting device. The boron-nitrogen compound of the present application, by collocating a fused heterocyclic structure with a limited group such as a tert-butyl group and a cycloalkyl group, can improve the thermal stability of the compound and has excellent light-emitting characteristics. The boron-nitrogen compound provided by the present application, as a light-emitting layer material, can effectively make the organic light-emitting device have a lower driving voltage and maintain the stability of the voltage, and the light-emitting efficiency is improved.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to a boron-nitrogen compound with multiple fused rings, an OLED having the compound, and an organic light-emitting device. Background Technology

[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting devices, are a technology that converts electrical energy into light energy through organic light-emitting materials. This technology involves applying voltage to an organic light-emitting element to inject holes from the anode and electrons from the cathode into the light-emitting layer. The injected holes and electrons then recombine to form excitons, causing light to be emitted.

[0003] Most OLED devices use a host-guest light-emitting system in their emissive layers, which involves doping a guest material into the host material. Currently, boron-nitrogen heterocyclic fused ring molecules are the focus of research in green light doping materials, but the types and quantities of existing materials are still relatively limited, making it difficult to study the structure-property relationship. Furthermore, in applications, display technology still suffers from high driving voltage and short display lifetime, which seriously affects the further practical application of this technology.

[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low voltage drive, high brightness and long lifespan, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems is a long-term need in this field. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides a boron-nitrogen compound with multi-component fused rings, an OLED, and a display or lighting device incorporating this compound. This boron-nitrogen compound, through the combination of boron-nitrogen fused heterocycles and defined groups, can improve luminous efficiency and thermal stability, and its molecular structure is easily modified. As a light-emitting layer material, the boron-nitrogen compound provided by this invention can effectively enable organic light-emitting devices to have lower driving voltages while maintaining voltage stability, and also improve luminous efficiency.

[0006] The boron-nitrogen compound with multiple fused rings provided by this invention is achieved through the following technical solution:

[0007] A boron-nitrogen compound with multiple fused rings,

[0008] Represented by Equation I:

[0009] ;

[0010] In Formula I, X is selected from C or Si; Y1 and Y3 represent the absence or presence of the substance; when Y1 and / or Y3 represent the presence of the substance, Y1 and Y3 are each independently selected from single bonds, O, S, C(CH3)2, and Si(CH3)2; ring M1 and ring M2 each independently represent one or more of C3-C20 cycloalkyl, C6-C30 aromatic ring, and C5-C36 heteroaromatic ring.

[0011] R1-R4, R6, and R7 represent unsubstituted, monosubstituted, or polysubstituted substances;

[0012] R1-R4, R 4' Each of the substituents is selected from one or more of hydrogen, deuterium, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and any two adjacent substituents may form a saturated or unsaturated C3-C12 membered ring.

[0013] R5 is selected from either hydrogen or deuterium, while R 5' R5 is independently selected from one or more of deuterium, substituted C6-C30 aryl, substituted or unsubstituted C5-C36 heteroaryl, and C6-C36 arylsilyl; or R5 is selected from deuterium, C1-C20 alkyl, and C6-C30 aryl, while R... 5' With R 4' Bonded into a ring; or R5, R 5' Simultaneously selected from deuterium;

[0014] R6-R7 are each selected from hydrogen, deuterium, C1-C20 alkyl, C1-C20 alkylamino, and C6-C36 arylamino, either identically or differently.

[0015] When R1-R7, R 4' R 5' When a substitution is included, the substitution is selected from one or more of deuterium, C1-C20 alkyl, C3-C20 cycloalkyl, and C6-C18 aryl.

[0016] Optionally, any two adjacent substituents can form a saturated or unsaturated C3-C12 membered ring.

[0017] In the compound shown in Formula I of this invention, the hydrogen atom can be replaced by deuterium, tritium, cyano, or halogen atoms.

[0018] Preferably, the present invention provides a boron-nitrogen compound having a multi-component fused ring structure, represented by Formula II:

[0019] ;

[0020] In Formula II, X and X1 are selected from C or Si; Y3 is selected from single bond, O, S, C(CH3)2, Si(CH3)2; Y4 is selected from single bond, O, S; rings M1, M2, M3, and M4 each independently represent one or more of C6-C30 aromatic rings and C3-C20 cycloalkyl groups; when X and X1 are both selected from Si, at least one of rings M1-M4 is a C6-C30 aromatic ring fused with C3-C20 cycloalkyl groups.

[0021] R1-R4 represent unsubstituted, monosubstituted, or polysubstituted products;

[0022] R1-R4 are each selected from one or more of hydrogen, deuterium, C1-C20 alkyl, C1-C20 alkyl-substituted or unsubstituted C3-C20 cycloalkyl, and any two adjacent substituents can form a saturated or unsaturated C3-C12 membered ring;

[0023] R5 is selected from hydrogen, deuterium, C1-C20 alkyl, and C6-C30 aryl;

[0024] R6-R7 are each selected from hydrogen, deuterium, C1-C20 alkyl, C1-C20 alkylamino, and C6-C36 arylamino, respectively, or are selected from one or more of hydrogen, deuterium, and C1-C20 alkyl.

[0025] Preferably, in Formula I or Formula II, rings M1, M2, M3, and M4 each independently represent phenyl, naphthyl, or tetrahydronaphthyl.

[0026] Preferably, R1-R4 in Formula I or Formula II are each selected from hydrogen, deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, adamantyl, methyl-substituted fused cyclopentyl, methyl-substituted fused cyclohexyl, tert-butyl-substituted or unsubstituted phenyl.

[0027] Preferably, in Formula I, R5 is selected from hydrogen or deuterium, while R... 5' R5 in Formula II is independently selected from one or more of deuterium, deuterated phenyl, tert-butylphenyl, terphenyl, triphenylsilyl, tetraphenylsilyl, biphenyl, tert-butyl-substituted biphenyl, carbazolyl, and N-phenylcarbazolyl; R5 in Formula II is independently selected from one or more of hydrogen, deuterium, tert-butyl, and phenyl.

[0028] Preferably, each of R6-R7 is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, dimethylamino, and diphenylamino.

[0029] Preferably, the structure described in Formula I is selected from any one of the following structures from Formula I-1 to Formula I-2:

[0030] ;

[0031] In equations I-1 to I-2, rings M1, M2, X, Y3, R1-R7, and R... 4' R 5' The substitution range is the same as defined in Equation I above.

[0032] According to one or more embodiments, the present invention provides a boron-nitrogen compound having a multi-component fused ring, wherein the compound is selected from any of the following chemical structures, where "tBu" represents tert-butyl, "Ph" represents phenyl, and "Ad" represents adamantyl: .

[0034] The present invention also provides the application of the boron nitrogen compound with multi-component fused rings as described above in the preparation of organic electroluminescent devices.

[0035] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising:

[0036] Substrate layer;

[0037] A first electrode is located on the substrate;

[0038] An organic light-emitting functional layer is disposed on the first electrode;

[0039] The second electrode is located on the organic light-emitting functional layer;

[0040] The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer contains a boron-nitrogen compound with multi-component fused rings as described above.

[0041] The present invention also provides a composition comprising a boron nitrogen compound having a multi-component fused ring as described in Formula I.

[0042] This invention also provides a formulation comprising a boron-nitrogen compound having a multi-component fused ring structure as shown in Formula I above, or a composition as described above, and at least one solvent. The solvent is not particularly limited and may be any solvent well known to those skilled in the art, such as unsaturated hydrocarbon solvents, halogenated saturated hydrocarbon solvents, halogenated unsaturated hydrocarbon solvents, ether solvents, or ester solvents; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetrahydronaphthalene, n-butylbenzene, sec-butylbenzene, or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene, or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; and the ester solvent is an alkyl benzoate ester.

[0043] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices. Preferably, the organic electroluminescent device prepared by the present invention is used in smartphones, tablets, smart wearable devices, televisions, VR, microdisplays, and automotive center console screens or taillights.

[0044] The present invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices described above.

[0045] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0046] This invention combines a boron-nitrogen fused heterocyclic structure with a spirocyclic fragment to create a large conjugated system in the boron-nitrogen compound. Modification with alkyl and cycloalkyl groups further enhances the structural stereochemistry, resulting in a structure with excellent thermal stability and film-forming properties. This structure exhibits superior hole and electron transport capabilities, effectively improving energy transfer performance between the host and guest components. When the boron-nitrogen compound provided by this invention is used to prepare organic light-emitting devices, it effectively enables lower driving voltages while maintaining voltage stability, while also improving luminous efficiency and extending the device's lifespan. Detailed Implementation

[0047] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0048] The term "alkyl" refers to and includes both straight-chain and branched alkyl groups. Preferred alkyl groups are those containing 1-20 carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc. Additionally, the alkyl group may optionally be substituted.

[0049] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 20 ring carbon atoms, more preferably those containing 3 to 12 ring carbon atoms, and particularly preferably those containing 3 to 6 ring carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Additionally, the cycloalkyl group may optionally be substituted.

[0050] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. A polycyclic system may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group; for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups are those containing six to thirty carbon atoms, more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Additionally, the aryl group may optionally be substituted.

[0051] The term "heteroaryl" refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group can be a monocyclic or fused-ring heteroaryl group, and can have 5 to 36 carbon atoms, preferably 6 to 20 carbon atoms. Examples include pyridyl, pyrrole, pyridinyl, thiophene, furanyl, indolyl, quinolinyl, isoquinolinyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, etc., but are not limited to these.

[0052] In this invention, the terms "optionally" or "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent..." means that the two substituents may or may not form a ring, that is, it includes both the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0053] Throughout this specification, unless explicitly stated otherwise, the term "including" any component will be understood to imply the inclusion of other components, not to exclude any other components. Furthermore, it should be understood that throughout this specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "above" another element, it may be "directly on" the other element, or there may be intermediate elements present. Additionally, "on" or "above" means located above the target portion, and not necessarily above it in the direction of gravity.

[0054] One object of the present invention is to provide an electroluminescent device, the organic electroluminescent device comprising: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; a second electrode on the organic light-emitting functional layer; the organic light-emitting functional layer comprising a light-emitting layer comprising a boron nitrogen compound having a multi-component fused heterocyclic segment.

[0055] In one embodiment of the present invention, the light-emitting layer of the organic electroluminescent (OLED) device comprises one or more compounds as light-emitting dopant materials as shown in the above general formula I.

[0056] In a preferred embodiment of the present invention, an OLED is provided, comprising a substrate, an anode, a cathode, and an organic light-emitting functional layer, wherein the organic light-emitting functional layer may include a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc., or may only include a light-emitting layer and one or more other layers; wherein the light-emitting layer comprises a light-emitting dopant material composed of one or more compounds represented by the above general formula (I). Optionally, a capping layer, a protective layer, and / or an encapsulation layer are further provided above the organic light-emitting functional layer.

[0057] The substrate described in this invention can be any substrate typically used in organic light-emitting devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties.

[0058] In a preferred embodiment of the present invention, the OLED device includes a hole injection layer, wherein the p-type dopant material in the hole injection layer may be selected from known or unknown materials, particularly preferably from the following structures, but this does not mean that the present invention is limited to the following structures:

[0059] .

[0060] In a preferred embodiment of the present invention, the OLED device includes a hole transport layer, which may be selected from known or unknown materials, particularly preferably from the following structures, but this does not mean that the present invention is limited to the following structures:

[0061] .

[0062] In a preferred embodiment of the present invention, the OLED device includes an electron transport layer, which may be selected from known or unknown materials, particularly preferably from the following structures, but this does not mean that the present invention is limited to the following structures:

[0063]

[0064] As a host material capable of producing green fluorescence, it not only needs to possess extremely high fluorescence quantum luminescence efficiency, but also needs to have an appropriate energy level to effectively coordinate with the excitation energy of the guest material to emit light. The host material can be selected from known or unknown materials.

[0065] The present invention will now be described in detail with reference to specific embodiments. Unless otherwise specified, all raw materials and solvents used in the synthesis embodiments are commercially available, and the solvents were used directly without further processing.

[0066] Example

[0067] Example 1: Synthesis of Compound 15

[0068] Synthesis route:

[0069] ;

[0070] 1) Compound SM1 (1 mmol) and CsCO3 (2 mmol) were dissolved in 50 mL of anhydrous DMF solution and stirred for 20 min. Compound SM2 (1 mmol) was added under a nitrogen atmosphere, and the mixture was heated to 120 °C for 15 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 over sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography using dichloromethane:petroleum ether = 1:4 as the eluent. Intermediate product S1;

[0071] 2) Dissolve intermediate product S1 (1 mmol) in 50 mL of THF solution. Under nitrogen atmosphere and low temperature, add n-butyllithium (2 mmol) solution and stir until dissolved. Then slowly add compound SM3 (1 mmol) in THF solution. Continue stirring the reaction solution at room temperature for 12 hours. After the reaction is complete, add 0.5 mol / L HCl solution, H2O, and EA. Extract with EA multiple times. Wash the organic phase with anhydrous DMF and dry with sodium sulfate. Rotary distillation through a column yields intermediate product S2.

[0072] 3) Dissolve intermediates S3 (1 mmol) and S2 (1 mmol) in 50 mL of toluene solution. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography using dichloromethane:petroleum ether = 1:4 as the eluent to obtain intermediate product S4.

[0073] 4) The intermediate S4 (1 mmol) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to -78 °C, and BuLi (1 mL, 2 mmol, 2 M in hexane) was slowly added. After reacting at -78 °C for 4 hours, BBr3 (247 mg, 1 mmol) was slowly added. After reacting at -50 °C for 1 hour, the temperature was raised to room temperature, and N,N-diisopropylethylamine (387 mg, 3 mmol) was added. The mixture was then heated to 120 °C and reacted 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 vacuum distillation, and the crude product was purified by silica gel column chromatography using dichloromethane:petroleum ether = 1:8 as the eluent to give the final product compound 15.

[0074] The structure of the target product compound 15 was tested: the theoretical value was 994.63 and the measured value was 995.25 by liquid chromatography-mass spectrometry (LC-MS).

[0075] Example 2: Synthesis of Compound 23

[0076] Following the synthesis steps and reaction conditions of Example 1, compound 23 was synthesized. The LC-MS (m / z) values ​​obtained by liquid chromatography-mass spectrometry were 974.61 and 975.23, respectively.

[0077] Example 3: Synthesis of Compound 46

[0078] Following the synthesis steps and reaction conditions of Example 1, compound 46 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1402.82 and a measured value of 1403.78 (m / z).

[0079] Example 4: Synthesis of Compound 47

[0080] Following the synthesis steps and reaction conditions of Example 1, compound 47 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1222.73 and a measured value of 1223.51 (m / z).

[0081] Example 5: Synthesis of Compound 55

[0082] Following the synthesis steps and reaction conditions of Example 1, compound 55 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1048.63 and a measured value of 1049.35 (m / z).

[0083] Example 6: Synthesis of Compound 61

[0084] Following the synthesis steps and reaction conditions of Example 1, compound 61 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1142.66 and a measured value of 1143.40 (m / z).

[0085] Example 7: Synthesis of Compound 65

[0086] Following the synthesis steps and reaction conditions of Example 1, compound 65 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1122.70 and a measured value of 1123.32 (m / z).

[0087] Example 8: Synthesis of Compound 68

[0088] Following the synthesis steps and reaction conditions of Example 1, compound 68 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1280.75 and a measured value of 1281.67 (m / z).

[0089] Example 9: Synthesis of Compound 69

[0090] Following the synthesis steps and reaction conditions of Example 1, compound 69 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1179.76 and a measured value of 1180.50 (m / z).

[0091] Example 10: Synthesis of Compound 70

[0092] Following the synthesis steps and reaction conditions of Example 1, compound 70 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1248.69 and a measured value of 1249.57 (m / z).

[0093] Example 11: Synthesis of Compound 72

[0094] Following the synthesis steps and reaction conditions of Example 1, compound 72 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1103.73 and a measured value of 1104.41 (m / z).

[0095] Example 12: Synthesis of Compound 75

[0096] Following the synthesis steps and reaction conditions of Example 1, compound 75 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1202.76 and a measured value of 1203.50 (m / z).

[0097] Example 13: Synthesis of Compound 77

[0098] Following the synthesis steps and reaction conditions of Example 1, compound 77 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 966.60 and a measured value of 967.12 (m / z).

[0099] Example 14: Synthesis of Compound 94

[0100] Following the synthesis steps and reaction conditions of Example 1, compound 94 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1076.66 and a measured value of 1077.38 (m / z).

[0101] Example 15: Synthesis of Compound 97

[0102] Following the synthesis steps and reaction conditions of Example 1, compound 97 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1134.71 and a measured value of 1135.47 (m / z).

[0103] Example 16: Synthesis of Compound 98

[0104] Following the synthesis steps and reaction conditions of Example 1, compound 98 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1382.77 and a measured value of 1383.65 (m / z).

[0105] Example 17: Synthesis of Compound 99

[0106] Following the synthesis steps and reaction conditions of Example 1, compound 99 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1183.69 and a measured value of 1184.41 (m / z).

[0107] Example 18: Synthesis of Compound 103

[0108] Following the synthesis steps and reaction conditions of Example 1, compound 103 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1309.74 and a measured value of 1310.60 (m / z).

[0109] Example 19: Synthesis of Compound 107

[0110] Following the synthesis steps and reaction conditions of Example 1, compound 107 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1164.56 and a measured value of 1165.28 (m / z).

[0111] Example 20: Synthesis of Compound 108

[0112] Following the synthesis steps and reaction conditions of Example 1, compound 108 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1012.49 and a measured value of 1013.11 (m / z).

[0113] Example 21: Synthesis of Compound 111

[0114] Following the synthesis steps and reaction conditions of Example 1, compound 111 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1180.68 and a measured value of 1181.42 (m / z).

[0115] Example 22: Synthesis of Compound 112

[0116] Following the synthesis steps and reaction conditions of Example 1, compound 112 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1460.99 and a measured value of 1461.97 (m / z).

[0117] Example 23: Synthesis of Compound 116

[0118] Following the synthesis steps and reaction conditions of Example 1, compound 116 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1040.52 and a measured value of 1041.14 (m / z).

[0119] Example 24: Synthesis of Compound 119

[0120] Following the synthesis steps and reaction conditions of Example 1, compound 119 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1188.74 and a measured value of 1189.26 (m / z).

[0121] Example 25: Synthesis of Compound 120

[0122] Following the synthesis steps and reaction conditions of Example 1, compound 120 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1032.63 and a measured value of 1033.21 (m / z).

[0123] Example 26: Synthesis of Compound 124

[0124] Following the synthesis steps and reaction conditions of Example 1, compound 124 was synthesized. The LC-MS (m / z) values ​​obtained by liquid chromatography-mass spectrometry were: theoretical value 1014.51, measured value 1015.11.

[0125] Example 27: Synthesis of Compound 127

[0126] Following the synthesis steps and reaction conditions of Example 1, compound 127 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 996.48 and a measured value of 997.02 (m / z).

[0127] Example 28: Synthesis of Compound 128

[0128] Following the synthesis steps and reaction conditions of Example 1, compound 128 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1028.44 and a measured value of 1029.18 (m / z).

[0129] Example 29: Synthesis of Compound 130

[0130] Following the synthesis steps and reaction conditions of Example 1, compound 130 was synthesized. The LC-MS (m / z) values ​​obtained by liquid chromatography-mass spectrometry were: theoretical value 1007.55, measured value 1008.13.

[0131] Example 30: Synthesis of Compound 131

[0132] Following the synthesis steps and reaction conditions of Example 1, compound 131 was synthesized. The LC-MS (m / z) values ​​obtained by liquid chromatography-mass spectrometry were 1031.51 and 1032.15, respectively.

[0133] Example 31: Synthesis of Compound 132

[0134] Following the synthesis steps and reaction conditions of Example 1, compound 132 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1023.52 and a measured value of 1024.16 (m / z).

[0135] Example 32: Synthesis of Compound 133

[0136] Following the synthesis steps and reaction conditions of Example 1, compound 133 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1184.71 and a measured value of 1185.35 (m / z).

[0137] Example 33: Synthesis of Compound 138

[0138] Following the synthesis steps and reaction conditions of Example 1, compound 138 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1404.93 and a measured value of 1405.87 (m / z).

[0139] Example 34: Synthesis of Compound 141

[0140] Following the synthesis steps and reaction conditions of Example 1, compound 141 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1436.88 and a measured value of 1438.00 (m / z).

[0141] The following are several examples of applications of the boron nitride compounds described in this invention in OLED devices to further illustrate the beneficial effects of the compounds. The materials used in the examples were either commercially available or synthesized in-house.

[0142] Manufacturing of OLED devices:

[0143] As a reference fabrication method for one embodiment of the device, this invention involves depositing a 50-500 nm ITO / Ag / ITO layer as the anode on an alkali-free glass substrate. Then, a hole injection layer (5 nm-20 nm), a hole transport layer (50-120 nm), a light-emitting auxiliary layer (5-120 nm), a light-emitting layer (20-50 nm), a hole blocking layer (5-20 nm), an electron transport layer (20-80 nm), and an electron injection layer (1-10 nm) are deposited on the anode. Next, Mg and Ag (weight ratio 1:9, 100-150 nm) are co-deposited to form a semi-transparent cathode, followed by the deposition of a capping compound. Finally, the light-emitting device is encapsulated using epoxy resin adhesive under a nitrogen atmosphere.

[0144] In a preferred embodiment, the OLED device provided by the present invention has the following structure: first, an alkali-free glass substrate is washed with isopropanol for 15 minutes using an ultrasonic cleaner, and then subjected to UV ozone washing treatment in the air for 30 minutes. The prepared substrate was vacuum-deposited with ITO / Ag / ITO 100nm as the anode. Then, a hole injection layer (HT:PD, 10nm, 2%), a hole transport layer (HT, 130nm), a light-emitting auxiliary layer (GP, 5nm), a green light-emitting layer (body material: dopant material = compound GHN01: GHP01: compound GD1: compound 1 (weight ratio 66:30:3:1, 30nm)), a hole blocking layer (compound HBL, 5nm), an electron transport layer (compound ET: Liq = 1:1, 30nm), and an electron injection layer (Yb, 1nm) were sequentially deposited. Mg and Ag (weight ratio 1:9, 130nm) were then co-deposited to form a semi-transparent cathode. Finally, compound CPL (65nm) was deposited as a capping layer. The light-emitting device was then encapsulated with epoxy resin adhesive under a nitrogen atmosphere, as described in Application Example 1. The molecular structural formulas of the relevant materials are shown below (particularly preferably selected from the following structures, but this does not mean that the invention is limited to the following structures):

[0145] .

[0146] Application Examples 2-34 and Comparative Examples 1-4 were prepared according to the method provided in Application Example 1 above, the only difference being that the compounds listed in Table 1 were used as dopant materials to replace compound 1 in Application Example 1. The dopant materials in Comparative Examples 1-4 are as follows:

[0147] Performance evaluation of OLED devices:

[0148] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and then the current density of the OLED device at different voltages was obtained by dividing the current by the emitting area. The brightness and radiant energy flux density of the OLED device at different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and brightness of the OLED device at different voltages, the current density (10 mA / cm²) at the same voltage was obtained. 2 The operating voltage (Volt) and current efficiency were measured. The test data are shown in Table 1, and are compared with the data from Comparative Example 1.

[0149] Table 1 Organic electroluminescent devices and their electron emission characteristics

[0150]

[0151] As shown in Table 1, compared with Comparative Examples 1-4, Application Examples 1 to 34 exhibit comparable operating voltage, higher BI luminous efficiency, and longer lifespan. Compared with Application Examples 1-2, when only Y3 is present, the compound exhibits better performance in the device through substitution transformations of R1-R4 on the boron-nitrogen core. Compared with Application Examples 3-34, the symmetrical fused structure formed on both sides above the boron-nitrogen core, combined with the selective combination of R1-R5 and rings M1-M4, further enhances the application performance of the resulting compound, especially in terms of luminous efficiency. The performance improvements in each application example are based on the fact that this invention, through the combination of different multi-component fused heterocyclic structures with limiting groups such as tert-butyl and cycloalkyl, enables boron-nitrogen compound materials to have better luminous efficiency. Furthermore, the good compatibility of the doped materials in this invention allows for better balance in electron and hole transport and exciton conversion in the luminescent layer, reducing device power consumption and extending lifespan.

[0152] This specific embodiment is merely an explanation of the present invention and is not intended to limit the invention. After reading this specification, those skilled in the art can make modifications to this embodiment without contributing any inventive step, but such modifications are protected by patent law as long as they are within the scope of the claims of the present invention.

Claims

1. A boron-nitrogen compound having a multi-component fused ring structure, characterized in that, Selected from any of the chemical structures shown below, where "tBu" represents tert-butyl and "Ph" represents phenyl: 。 2. The application of the boron-nitrogen compound with multi-component fused rings as described in claim 1 in the preparation of organic electroluminescent devices.

3. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: Substrate layer; A first electrode is located on the substrate; An organic light-emitting functional layer is disposed on the first electrode; The second electrode is located on the organic light-emitting functional layer; The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes a boron-nitrogen compound having a multi-component fused ring as described in claim 1.

4. A composition, characterized in that, The composition comprises a boron nitrogen compound having a multi-component fused ring as described in claim 1.

5. A formulation, characterized in that, The formulation comprises a boron nitrogen compound having a multi-component fused ring as described in claim 1 or a composition as described in claim 4 and at least one solvent.

6. A display or lighting device, characterized in that, The device includes the organic electroluminescent device as described in claim 3.

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