An organic compound and its application, an organic electroluminescent device

Abstract

The present invention relates to the field of organic electroluminescent devices, and discloses an organic compound, its application, and an organic electroluminescent device. The compound has a structure represented by formula (I). When used as an electron transport material in an organic electroluminescent device, the organic compound of the present invention exhibits a lower driving voltage and higher device luminous efficiency. When used as an electron blocking material in an organic electroluminescent device, the organic compound exhibits a lower driving voltage and higher device luminous efficiency. #imgabs0#

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent devices, and in particular to an organic compound and application thereof, and an organic electroluminescent device. Background Art

[0002] The phenomenon of organic electroluminescence was first discovered by Pope et al. in 1963. They found that a single-layer crystal of anthracene could emit a faint blue light when driven by a voltage above 100V. However, due to the high driving voltage and the large thickness of the single-crystal anthracene, it did not attract widespread attention.

[0003] It was not until 1987 that Dr. Qingyun Deng and others from Eastman Kodak reported that they had prepared a double-layer organic electroluminescent device (OLED) by vacuum thermal evaporation based on two organic semiconductor materials: 8-hydroxyquinoline aluminum with high fluorescence efficiency and good electron transport properties and aromatic diamine with good hole transport properties.

[0004] At a driving voltage of less than 10V, the external quantum efficiency of the aforementioned OLED reached 1%, and the brightness was as high as 1000Cd / m 2 , which set off a boom in OLED research and prompted further research on organic electroluminescent materials.

[0005] In recent years, OLED has gradually entered people's field of vision as a new generation of display technology. Its broad application prospects and rapid technological progress have made OLED one of the hottest research areas in the display field and scientific research product development.

[0006] At present, OLED or screen still has the defects of high driving voltage and low current efficiency. In order to improve these defects, on the one hand, the device structure and manufacturing process need to be further optimized, and on the other hand, the performance of each functional layer material also needs to be improved.

[0007] Electron transport materials and electron blocking layer materials play a vital role in the driving voltage and luminous efficiency of the device.

[0008] Therefore, the market urgently needs to develop high-performance electron transport materials and electron blocking layer materials to reduce the driving voltage of the device and improve the luminous efficiency of the device. Summary of the Invention

[0009] The purpose of the present invention is to overcome the defects of the OLED provided by the prior art, such as high driving voltage and low luminous efficiency.

[0010] In order to achieve the above object, the first aspect of the present invention provides an organic compound having a structure shown in formula (I):

[0011]

[0012] Wherein, in formula (I),

[0013] X1, X2, X3 are each independently selected from O, S, N, -C(R1)-; R1 is selected from C 1-12 Alkyl, C 3-12 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0014]

[0015] R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituted or unsubstituted group provided by the structure represented by formula (A), -L-, a substituted or unsubstituted group provided by the structure represented by formula (A); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein two of them are not simultaneously substituted or unsubstituted groups provided by the structure shown in formula (A) or -L- substituted or unsubstituted groups provided by the structure shown in formula (A); and when R 41 and R 42 When one of them is a substituted or unsubstituted group provided by the structure represented by formula (A) or -L- is a substituted or unsubstituted group provided by the structure represented by formula (A), R 21 、R 22 、R 31 、R 32 All are H;

[0016] L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene; and any bondable position in the structure represented by formula (A) is connected to the parent core structure, or any bondable position in the structure represented by formula (A) is connected to the parent core structure through L;

[0017] At least two of Y1, Y2, Y3, Y4, Y5, and Y6 are N, and the remaining atoms are optionally C atoms substituted by R5;

[0018] Each R5 is independently selected from H, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl; or R5 on any two adjacent Cs are cyclized to form a phenyl group;

[0019] The substituents optionally present in the structure represented by formula (A) are each independently selected from phenyl, naphthyl, C 1-12 Alkyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl.

[0020] The second aspect of the present invention provides use of the organic compound described in the first aspect in an organic electroluminescent device.

[0021] The third aspect of the present invention provides an organic electroluminescent device comprising one or more of the organic compounds described in the first aspect, wherein the organic compound is present in at least one of the electron transport layer, the light emitting layer, and the hole blocking layer of the organic electroluminescent device;

[0022] Preferably, the organic compound is present in the light-emitting layer of the organic electroluminescent device.

[0023] When the organic compound of the present invention is used as an electron transport material in an organic electroluminescent device, it has a lower driving voltage and a higher device luminous efficiency.

[0024] In addition, the organic compound of the present invention has a lower driving voltage and a higher device luminous efficiency when used as an electron blocking material in an organic electroluminescent device. DETAILED DESCRIPTION

[0025] The endpoints of the ranges and any values ​​disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoints of each range, the endpoints of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered to be specifically disclosed herein.

[0026] The "deuterated C" of the present invention 1-6 Alkyl, deuterated C 1-6 The term "cycloalkyl, deuterated phenyl, deuterated naphthyl and deuterated biphenyl" means that a deuterium atom can replace a H atom in any substitutable position of the group.

[0027] The present invention's "C 3-8 The term "cycloalkyl group" refers to a cycloalkyl group having 3 to 8 carbon atoms, for example, a C3 cycloalkyl group, a C4 cycloalkyl group, a C5 cycloalkyl group, a C6 cycloalkyl group, a C7 cycloalkyl group and a C8 cycloalkyl group.

[0028] The present invention's "C 1-6 The term "alkyl" refers to an alkyl group having a total carbon atom count of 1 to 6, for example, a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group and a C6 alkyl group; and includes straight-chain alkyl groups and branched-chain alkyl groups.

[0029] In formula (I) and formula (A) of the present invention, “○” therein represents a conjugated structure, and a double bond can be formed at any place where a double bond can be formed.

[0030] As mentioned above, one aspect of the present invention provides an organic compound having a structure shown in formula (I):

[0031]

[0032] Wherein, in formula (I),

[0033] X1, X2, X3 are each independently selected from O, S, N, -C(R1)-; R1 is selected from C 1-12 Alkyl, C 3-12 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0034]

[0035] R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituted or unsubstituted group provided by the structure represented by formula (A), -L-, a substituted or unsubstituted group provided by the structure represented by formula (A); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein two of them are not simultaneously substituted or unsubstituted groups provided by the structure shown in formula (A) or -L- substituted or unsubstituted groups provided by the structure shown in formula (A); and when R 41 and R 42 When one of them is a substituted or unsubstituted group provided by the structure represented by formula (A) or -L- is a substituted or unsubstituted group provided by the structure represented by formula (A), R 21 、R 22 、R 31 、R 32 All are H;

[0036] L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene; and any bondable position in the structure represented by formula (A) is connected to the parent core structure, or any bondable position in the structure represented by formula (A) is connected to the parent core structure through L;

[0037] At least two of Y1, Y2, Y3, Y4, Y5, and Y6 are N, and the remaining atoms are optionally C atoms substituted by R5;

[0038] Each R5 is independently selected from H, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl; or R5 on any two adjacent Cs are cyclized to form a phenyl group;

[0039] The substituents optionally present in the structure represented by formula (A) are each independently selected from phenyl, naphthyl, C 1-12 Alkyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl.

[0040] According to a preferred embodiment, in formula (I),

[0041]

[0042] X1 is O or S; X2 is C; X3 is N; R1 is selected from C 1-12 Alkyl, C 3-12 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0043] R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), and a substituent represented by formula (Q5); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein each of the two is not simultaneously any one of the substituent represented by formula (Q1), the substituent represented by formula (Q2), the substituent represented by formula (Q3), the substituent represented by formula (Q4), and the substituent represented by formula (Q5); and when R41 and R 42 When one of the substituents is a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), or a substituent represented by formula (Q5), R 21 、R 22 、R 31 、R 32 All are H;

[0044] In formula (Q1), formula (Q2), formula (Q3), formula (Q4), and formula (Q5),

[0045] wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene;

[0046] At least two of Y1, Y2 and Y3 are N, and optionally the remaining one is C;

[0047] R 51 and R 52 Each is independently selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl;

[0048] R6 and R7 are each independently selected from H, phenyl, naphthyl, C 1-12 Alkyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl;

[0049] Preferably,

[0050] In formula (I),

[0051] X1 is O or S; X2 is C; X3 is N;

[0052] R1 is selected from C 1-6 Alkyl, C 3-8 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0053] R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), and a substituent represented by formula (Q5); and R 21and R 22 , R 31 and R 32 , R 41 and R 42 wherein each of the two is not simultaneously any one of the substituent represented by formula (Q1), the substituent represented by formula (Q2), the substituent represented by formula (Q3), the substituent represented by formula (Q4), and the substituent represented by formula (Q5); and when R 41 and R 42 When one of the substituents is a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), or a substituent represented by formula (Q5), R 21 、R 22 、R 31 、R 32 All are H;

[0054] In formula (Q1), formula (Q2), formula (Q3), formula (Q4), and formula (Q5),

[0055] wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene;

[0056] At least two of Y1, Y2 and Y3 are N, and optionally the remaining one is C;

[0057] R 51 and R 52 Each is independently selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl;

[0058] R6 and R7 are each independently selected from H, phenyl, naphthyl, C 1-6 Alkyl, 9,9-dimethylfluorenyl, dibenzothiophene.

[0059] According to another preferred embodiment, in formula (I),

[0060] X1 is O or S; X2 is C; X3 is N;

[0061] R1 is selected from C 1-6 Alkyl, C 3-8 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0062] R 21 、R 22 、R31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q1); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 In the formula (Q1), each of the two is not the same; and when R 41 and R 42 When one of them is a substituent represented by formula (Q1), R 21 、R 22 、R 31 、R 32 All are H;

[0063] In formula (Q1),

[0064] wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene;

[0065] At least two of Y1, Y2 and Y3 are N, and optionally the remaining one is C;

[0066] R 51 and R 52 Each is independently selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, and 9,9-dimethylfluorenyl.

[0067] According to a particularly preferred embodiment, the compound of the structure shown in formula (I) is selected from any one of the following:

[0068]

[0069]

[0070]

[0071]

[0072] Preferably, in formula (I),

[0073] X1 is O or S; X2 is C; X3 is N;

[0074] R1 is selected from C 1-6 Alkyl, C 3-8 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0075] R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), and a substituent represented by formula (Q5); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein each of the two is not simultaneously any one of the substituent represented by formula (Q2), the substituent represented by formula (Q3), the substituent represented by formula (Q4), and the substituent represented by formula (Q5); and when R 41 and R 42 When one of the substituents is any one of the substituents represented by formula (Q2), the substituents represented by formula (Q3), the substituents represented by formula (Q4), and the substituents represented by formula (Q5), R 21 、R 22 、R 31 、R 32 All are H;

[0076] In formula (Q2), formula (Q3), formula (Q4), and formula (Q5),

[0077] wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene;

[0078] R6 and R7 are each independently selected from H, phenyl, naphthyl, C 1-6 Alkyl, 9,9-dimethylfluorenyl, dibenzothiophene.

[0079] More preferably, the compound of the structure represented by formula (I) is selected from any one of the following:

[0080]

[0081]

[0082]

[0083]

[0084] According to a particularly preferred embodiment, the compound having the structure shown in formula (I) is selected from any one of the following:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] The present invention has no particular limitation on the specific method for preparing the aforementioned compounds. Those skilled in the art can obtain the aforementioned compounds of the present invention based on the specific structural formula provided by the present invention in combination with conventional process routes in the field of organic synthesis. In addition, several examples are exemplarily listed later in the present invention to illustrate the preparation methods of the compounds of the present invention. Those skilled in the art can also obtain the specific preparation methods of all other compounds by replacing the types of raw materials according to the preparation methods of the compounds in the present invention. The present invention no longer describes the preparation methods of all compounds in detail, and those skilled in the art should not be understood as limiting the present invention.

[0093] As mentioned above, the second aspect of the present invention provides use of the organic compound described in the first aspect in an organic electroluminescent device.

[0094] According to a preferred embodiment, the present invention provides an organic electroluminescent device, comprising: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein the one or more organic material layers contain at least one of the aforementioned compounds of the present invention.

[0095] In the present invention, one of the first electrode and the second electrode is an anode, and the other is a cathode.

[0096] According to a preferred embodiment of the present invention, the organic electroluminescent device of the present invention includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron injection layer, etc. as organic material layers.

[0097] As mentioned above, the third aspect of the present invention provides an organic electroluminescent device comprising one or more of the organic compounds described in the first aspect, wherein the organic compound is present in at least one of the electron transport layer, the light emitting layer, and the hole blocking layer of the organic electroluminescent device;

[0098] Preferably, the organic compound is present in the light-emitting layer of the organic electroluminescent device.

[0099] Preferably, the organic compound exists as a red light host material in the light-emitting layer of the organic electroluminescent device.

[0100] The inventors of the present invention have found that when the compound of the present invention is used as a red light host material in the light-emitting layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency.

[0101] Preferably, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer stacked in sequence.

[0102] The organic electroluminescent device of the present invention is preferably coated with one or more layers by means of a sublimation method. In this case, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The compounds provided by the present invention are applied by vapor deposition at an initial pressure of 1.5 Pa.

[0103] The organic electroluminescent device of the invention is also preferably coated with one or more layers by an organic vapor deposition method or by means of carrier gas sublimation. -6 The compound is applied at a pressure of 100 Pa to 100 Pa. A particular example of this method is an organic vapor deposition printing method, in which the compound provided by the present invention is directly applied through a nozzle to form a device structure.

[0104] The organic electroluminescent device of the present invention preferably comprises the compound of the present invention formulated into a solution, and is formed into a layer or a plurality of layers by spin coating or by any printing method, such as screen printing, flexographic printing, inkjet printing, lithographic printing, more preferably photoinduced thermal imaging or inkjet printing. Generally, when multiple layers are produced in this way, damage between the layers is likely to occur. That is, when one layer is completed and another layer is produced using the solution, the solvent in the solution will destroy the already formed layer, which is not conducive to the production of the organic electroluminescent device. However, the compound provided by the present invention can undergo cross-linking under heating or ultraviolet exposure, thereby maintaining the intact layer without being destroyed. The compound of the present invention can also be applied from a solution and fixed in the corresponding layer by subsequent cross-linking in the polymer network.

[0105] The organic electroluminescent device of the invention can be produced as a hybrid system by applying one or more layers by solution and one or more other layers by vapor deposition.

[0106] According to some embodiments of the present invention, the anode material forming the anode is generally preferably a material with a large work function. For example, the anode material used in the present invention is selected from one or more of the following materials: metals, such as vanadium, chromium, copper and gold, or other alloys: metal oxides, such as zinc oxide, indium oxide, indium tin oxide, indium zinc oxide and tin dioxide, combinations of metals and oxides, such as zinc oxide: aluminum, but not limited thereto.

[0107] According to some embodiments of the present invention, the material forming the hole injection layer has the ability to transport holes. Therefore, the material of the hole injection layer has an effect of injecting holes into the anode, has an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and further has excellent thin film forming ability. The HOMO of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0108] According to some embodiments of the present invention, the material forming the hole transport layer is a material that can receive holes from the anode or the hole injection layer, move the holes to the light emitting layer, and has high mobility for holes.

[0109] According to some embodiments of the present invention, the hole injection material and the hole transport material include at least one of aromatic amine derivatives (such as NPB, SqMA1), hexaazatriphenylene derivatives (such as HACTN), indolecarbazole derivatives, conductive polymers (such as PEDOT / PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorene amine, and spirodifluorene amine, but are not limited thereto.

[0110] According to some embodiments of the present invention, the hole injection layer and the hole transport layer may be formed using, for example, aromatic amine derivatives of the following general formula:

[0111]

[0112] The groups R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolecarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.

[0113] According to some embodiments of the present invention, the material for forming the electron blocking layer is not particularly limited. Generally, compounds that meet the first and / or second conditions below can be considered:

[0114] First: It has a shallower LUMO energy level (smaller absolute value), the purpose of which is to reduce the number of electrons leaving the light-emitting layer, thereby increasing the probability of electron and hole recombination in the light-emitting layer.

[0115] Second: It has a larger triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby improving the efficiency of exciton conversion to luminescence.

[0116] According to some embodiments of the present invention, the materials forming the electron blocking layer include but are not limited to aromatic amine derivatives (such as NPB) and spirobifluorenamine (such as SpMA2), wherein some electron blocking materials have similar structures to hole injection materials and hole transport materials.

[0117] According to some embodiments of the present invention, the light-emitting material of the light-emitting layer is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining the holes and electrons, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.

[0118] According to some embodiments of the present invention, the light emitting layer may include a host material and a guest material.

[0119] According to some embodiments of the present invention, the guest material is preferably a compound that produces emission via at least one of phosphorescence, fluorescence, TADF (thermally activated delayed fluorescence), MLCT (metal to ligand charge transfer), HLCT (with hybrid CT states) and triplet-triplet annihilation methods.

[0120] According to some embodiments of the present invention, the guest material in the light-emitting layer may include derivatives of perylene, derivatives of anthracene, fluorene derivatives, distyryl aromatic derivatives, aromatic amine derivatives, organic silicon derivatives, organic boron derivatives, carbazole-triazine derivatives, acridine derivatives, ketone derivatives, sulfone derivatives, cyano derivatives and xanthene derivatives, but is not limited thereto.

[0121] In some preferred embodiments of the present invention, the sulfone derivative has the general formula shown below:

[0122]

[0123] The ketone derivatives have the general formula shown below:

[0124]

[0125] In the general formulas of the above-mentioned sulfone derivatives and ketone derivatives, R 20 、R 21 、R 22 and R 23Each is independently selected from a single bond, hydrogen, deuterium, an alkyl group, benzene, diphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolecarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and a group represented by a substituent thereof.

[0126] According to some embodiments of the present invention, the material of the hole blocking layer may also preferably be a compound having the following first and / or second conditions:

[0127] First: It has a deeper HOMO energy level (larger absolute value), the purpose of which is to reduce the number of holes leaving the light-emitting layer, thereby increasing the probability of electrons and holes being recombined in the light-emitting layer.

[0128] Second: It has a larger triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby improving the efficiency of exciton conversion to luminescence.

[0129] According to some embodiments of the present invention, the material forming the hole blocking layer may include, for example, phenanthroline derivatives (eg, Bphen, BCP), triphenylene derivatives, and benzimidazole derivatives, but is not limited thereto.

[0130] The electron transport layer receives electrons from the electron injection layer and transfers them to the light-emitting layer. Suitable electron transport materials include materials that can receive electrons from the cathode, transfer them to the light-emitting layer, and have high electron mobility. Examples of electron transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; and hydroxyflavone-metal complexes.

[0131] According to some embodiments of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film forming ability. Examples of electron injection layer materials include, but are not limited to, LiF, CsF, Cs2CO3, and LiQ.

[0132] According to some embodiments of the present invention, the cathode material is preferably formed of a material with a small work function, which can smoothly inject electrons into the organic material layer. The cathode material that can be used in the present disclosure can be selected from one or more of the following materials, one or more of Al, Mg and Ag.

[0133] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, all raw materials used are common commercially available products.

[0134] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are common commercial products. Unless otherwise specified, the room temperature described below refers to 25±1°C.

[0135] Preparation Example 1

[0136]

[0137] Synthesis of Intermediate N-1-1: In a 500 mL three-necked flask, oxazole (0.145 mol) was dissolved in anhydrous THF (100 ml). After complete dissolution, the mixture was cooled to -30°C, and then 1 M lithium diisopropylamide (LDA) solution (45 mL) was slowly added. The reaction was continued at -20°C for 2 h. Then, iodomethane (0.145 mol) was added, and the temperature was slowly raised to room temperature, and the reaction was continued for 3 h. The reaction was quenched with saturated aqueous sodium bisulfite solution, and extracted three times with dichloromethane. The organic phases were combined, dried, filtered, and then spin-dried. Column chromatography was performed to obtain Intermediate N-1-1 as a white solid (yield: 64%).

[0138] The following compounds can be obtained in a similar manner, except that oxazole and iodomethane are replaced by the corresponding reactants in Table 1.

[0139]

[0140] Synthesis of Intermediate N-1: In a 500 mL three-necked flask, intermediate N-1-1 (0.09 mol) was added to dichloromethane (75 mL). Br2 (0.18 mol) was added dropwise at room temperature with stirring. The reaction mixture was allowed to react overnight at room temperature. After the reaction of the starting material was complete, water (200 mL) was added dropwise to the reaction solution. The mixture was extracted three times with dichloromethane. The residue was filtered and purified by column chromatography to obtain intermediate N-1 (yield 58%).

[0141] Mass spectrum: C4H3BrNO, theoretical value: 238.86, found value: 238.85. Elemental analysis: theoretical value: C: 19.94%, H: 1.26%, N: 5.81%; found value: C: 19.95%, H: 1.25%, N: 5.82%.

[0142] The synthesis method of intermediate N-2, intermediate N-3, intermediate N-4, intermediate N-5, intermediate N-6, and intermediate N-7 is the same as the synthesis method of intermediate N-1, except that intermediate N-1-1 is replaced by the corresponding product in Table 1 to obtain intermediate N-2, intermediate N-3, intermediate N-4, intermediate N-5, intermediate N-6, and intermediate N-7, respectively.

[0143]

[0144] Intermediate N-2: Mass spectrum: C5H5Br2NO, theoretical value: 252.87, found value: 252.85. Elemental analysis: theoretical value: C: 23.56%, H: 1.98%, N: 5.49%; found value: C: 23.60%, H: 1.95%, N: 5.50%.

[0145] Intermediate N-3: Mass spectrum: C7H9Br2NO, theoretical value: 280.91, found value: 280.85. Elemental analysis: theoretical value: C: 29.71%, H: 3.21%, N: 4.95%; found value: C: 29.70%, H: 3.20%, N: 4.96%.

[0146] Intermediate N-4: mass spectrum: C9D5Br2NO, theoretical value: 305.91, found value: 305.90.

[0147] Intermediate N-5: Mass spectrum: C9H5Br2NS, theoretical value: 316.85, found value: 316.80. Elemental analysis: theoretical value: C: 33.88%, H: 1.58%, N: 4.39%; found value: C: 33.90%, H: 1.60%, N: 4.40%.

[0148] Intermediate N-6: mass spectrum: C9D5Br2NS, theoretical value: 321.88, found value: 321.85.

[0149] Intermediate N-7: mass spectrum: C4D3Br2NS, theoretical value: 257.85, found value: 257.90.

[0150] Table 1

[0151]

[0152] Preparation Example 2

[0153]

[0154] Synthesis of Intermediate M: Under nitrogen, a 500 mL three-necked flask was charged with 2,3-dibromoquinoxaline (70 mmol), phenylboronic acid (70 mmol), isopropyl alcohol, water (a mixture of isopropyl alcohol and water in a volume ratio of 3:1) (200 mL), anhydrous potassium carbonate (175 mmol), and bis(triphenylphosphine)palladium dichloride (0.7 mmol). Stirring was initiated and the mixture was heated to 80°C and refluxed for 4 h. The reaction mixture was cooled to room temperature and separated. The organic phase was washed with saturated sodium chloride until neutral. The organic phase was then passed through a silica gel column with toluene as the eluent, eluting with 500 mL of toluene. The solvent was removed from the organic phase using a rotary evaporator to obtain Intermediate M (yield: 85%).

[0155] Mass spectrum: C14H9BrN2, theoretical value: 283.99, found value: 283.95. Elemental analysis: theoretical value: C: 58.97%, H: 3.18%, N: 9.82%; found value: C: 58.95%, H: 3.20%, N: 9.80%.

[0156] Preparation Example 3

[0157]

[0158] Synthesis of intermediate Aa-2: In a 500 mL three-necked flask, p-chlorophenylhydrazine hydrochloride (112 mmol), 1,2-cyclohexanedione (112 mmol), and ethanol (200 mL) were added in sequence. Concentrated sulfuric acid (50 mmol) was added dropwise over 3 min. Under nitrogen protection, the mixture was heated with stirring to 65°C. The reaction was completed after 4 h. The mixture was cooled to room temperature, filtered, washed with ethanol / oil ether, and recrystallized to obtain a brown solid (yield: 83%).

[0159] Synthesis of intermediate Aa-3: In a 500 mL three-necked flask, add intermediate Aa-2 (90 mmol), acetic acid (220 mL), and trifluoroacetic acid (270 mmol). Under nitrogen protection, heat and stir, and raise the temperature to reflux. The reaction is complete after 8 hours. Cool to room temperature, filter, and recrystallize with acetic acid / oil ether to obtain intermediate Aa-3 (yield: 76%).

[0160] Synthesis of intermediate Aa-4: In a 500 mL three-necked flask, under nitrogen protection, intermediate Aa-3 (68 mmol), carbonylbenzyl chloride (Cbz) (68 mmol), activated copper powder (136 mmol), 18-crown-6 (13.6 mmol), potassium carbonate (170 mmol) and o-dichlorobenzene (240 mL) were added in sequence, heated with stirring, and the temperature was raised to reflux for 62 h. The reaction solution was cooled to room temperature, 250 mL of toluene was added, filtered, and the filtrate was evaporated under reduced pressure. Column chromatography was performed using petroleum ether / ethyl acetate as eluent to obtain intermediate Aa-4 (yield: 78%).

[0161] Synthesis of intermediate Aa-5: In a 500 mL three-necked flask, add p-chlorophenylhydrazine hydrochloride (52 mmol), intermediate Aa-4 (52 mmol), and ethanol (180 mL). Add concentrated sulfuric acid (23 mmol) dropwise within 3 min. Protect with nitrogen and heat with stirring. Raise the temperature to 65°C. The reaction is complete after 3 h. Cool to room temperature, filter, wash with ethanol / oil ether and recrystallize to obtain intermediate Aa-5 (yield: 79%).

[0162] Synthesis of intermediate Aa-6: In a 500 mL three-necked flask, add intermediate Aa-5 (40 mmol), acetic acid (200 mL), and trifluoroacetic acid (120 mmol). Under nitrogen protection, heat and stir, and raise the temperature to reflux. The reaction is complete after 6 hours. Cool to room temperature, filter, and recrystallize with acetic acid / oil ether to obtain intermediate Aa-6 (yield: 73%).

[0163] Synthesis of intermediate Aa-7: In a 500 mL three-necked flask, under nitrogen protection, intermediate Aa-6 (44 mmol), intermediate N-1 (44 mmol), activated copper powder (88 mmol), 18-crown-6 (8.8 mmol), potassium carbonate (110 mmol) and o-dichlorobenzene (200 ml) were added in sequence, heated with stirring, and the temperature was raised to reflux for 55 h. The reaction solution was cooled to room temperature, 200 mL of toluene was added, filtered, and the filtrate was dried under reduced pressure. Column chromatography was performed using petroleum ether / ethyl acetate as eluent to obtain intermediate Aa-7 (yield: 75%).

[0164] Synthesis of intermediate Aa-8: In a 500 mL three-necked flask, under nitrogen protection, add intermediate Aa-7 (30 mmol) and methanol (185 mL). After stirring and dissolving, add formic acid (9 mmol) and palladium acetate (0.6 mmol). Heat with stirring and raise the temperature to reflux. After reacting for 2 h, the reaction solution is cooled to room temperature and triethylamine is added to adjust the pH of the solution to 7. The solution is dried under reduced pressure and the residue is separated by silica gel chromatography to obtain intermediate Aa-8 (yield: 83%).

[0165] Synthesis of intermediate Aa: In a 500 mL three-necked flask, under nitrogen protection, intermediate Aa-8 (44 mmol), intermediate N-1 (44 mmol), activated copper powder (88 mmol), 18-crown-6 (8.8 mmol), potassium carbonate (110 mmol) and o-dichlorobenzene (200 mL) were added in sequence, heated with stirring, and the temperature was raised to reflux for 55 h. The reaction solution was cooled to room temperature, 200 mL of toluene was added, filtered, and the filtrate was evaporated under reduced pressure. Column chromatography was performed using petroleum ether / ethyl acetate as eluent to obtain intermediate Aa (yield: 75%).

[0166] Mass spectrum: C23H13Cl2N3O, theoretical value: 417.04, found value: 417.05. Elemental analysis: theoretical value: C: 66.04%, H: 3.13%, N: 10.05%; found value: C: 66.05%, H: 3.10%, N: 10.00%.

[0167] The synthesis method of intermediate Ab, intermediate Ac, intermediate Ad and intermediate Ae is the same as the synthesis method of Aa above, except that different raw materials are used to obtain intermediate Ab, intermediate Ac, intermediate Ad and intermediate Ae.

[0168]

[0169] Intermediate Ab: Mass spectrum: C27H13Cl2N3S, theoretical value: 481.02, found value: 481.05. Elemental analysis: theoretical value: C: 67.23%, H: 2.72%, N: 8.71%; found value: C: 67.25%, H: 2.70%, N: 8.70%.

[0170] Intermediate Ac: Mass spectrum: C22H8D3Cl2N3S, theoretical value: 422.02, found value: 422.05. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.32~7.36 (2H, d), 7.44~7.50 (2H, m), 7.98~8.07 (2H, m), 8.44~8.48 (1H, d), 8.59~8.63 (1H, d).

[0171] Intermediate Ad: Mass spectrum: C27H8D5Cl2N3O, theoretical value: 470.07, found value: 470.05. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.32~7.36 (2H, d), 7.47~7.51 (2H, m), 7.96~7.98 (1H, d), 8.07~8.09 (1H, d), 8.49~8.52 (1H, d), 8.69~8.72 (1H, d).

[0172] Intermediate Ae: Mass spectrum: C22H11Cl2N3O, theoretical value: 403.03, found value: 403.05. Elemental analysis: theoretical value: C: 65.36%, H: 2.74%, N: 10.39%; found value: C: 65.35%, H: 2.75%, N: 10.40%.

[0173] Preparation Example 4

[0174]

[0175] Synthesis of intermediate Ba-1: The synthesis method of intermediate Ba-1 is the same as that of intermediate Aa-5, except that p-chlorophenylhydrazine hydrochloride is replaced by phenylhydrazine hydrochloride to obtain intermediate Ba-1 (yield: 82%).

[0176] Synthesis of intermediate Ba-2: The synthesis method of intermediate Ba-2 is the same as that of intermediate Aa-6, except that intermediate Aa-5 is replaced by intermediate Ba-1 to obtain intermediate Ba-2 (yield: 75%).

[0177] Synthesis of intermediate Ba-3: The synthesis method of intermediate Ba-3 is the same as that of intermediate Aa-7, except that intermediate Aa-6 is replaced by intermediate Ba-2 to obtain intermediate Ba-3 (yield: 72%).

[0178] Synthesis of intermediate Ba-4: The synthesis method of intermediate Ba-4 is the same as that of intermediate Aa-8, except that intermediate Aa-7 is replaced by intermediate Ba-3 to obtain intermediate Ba-4 (yield: 85%).

[0179] Synthesis of intermediate Ba: The synthesis method of intermediate Ba is the same as that of intermediate Aa, except that intermediate Aa-8 is replaced by intermediate Ba-4 to obtain intermediate Ba (yield: 73%).

[0180] Mass spectrum: C22H12ClN3O, theoretical value: 369.07, found value: 369.05.

[0181] Elemental analysis: Theoretical value: C: 71.45%, H: 3.27%, N: 11.36%; Found value: C: 71.40%, H: 3.30%, N: 11.35%.

[0182] The synthesis method of intermediates Bb, Bc and Bd is the same as the above-mentioned synthesis method of Ba, except that different raw materials are used to obtain intermediates Bb, Bc and Bd.

[0183]

[0184] Intermediate Bb: Mass spectrum: C27H9D5ClN3O, theoretical value: 436.11, found value: 436.10. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.13 ~ 7.24 (2H, m), 7.31 ~ 7.49 (3H, m), 7.94 ~ 7.97 (1H, d), 8.15 ~ 8.22 (1H, m), 8.40 ~ 8.45 (1H, d), 8.56 ~ 8.60 (1H, d).

[0185] Intermediate Bc: Mass spectrum: C27H14ClN3S, theoretical value: 447.06, found value: 447.05. Elemental analysis: theoretical value: C: 72.40%, H: 3.15%, N: 9.38%; found value: C: 72.35%, H: 3.20%, N: 9.35%.

[0186] Intermediate Bd: Mass spectrum: C25H18ClN3O, theoretical value: 411.11, found value: 411.10. Elemental analysis: theoretical value: C: 72.90%, H: 4.40%, N: 10.20%; found value: C: 72.95%, H: 4.42%, N: 10.25%.

[0187] Preparation Example 5

[0188]

[0189] Synthesis of intermediate Ca-2: The synthesis of intermediate Ca-2 is the same as that of intermediate Aa-2, except that p-chlorophenylhydrazine hydrochloride is replaced by phenylhydrazine hydrochloride to obtain intermediate Ca-2 (yield: 86%).

[0190] Synthesis of intermediate Ca-3: The synthesis of intermediate Ca-3 is the same as that of intermediate Aa-3, except that intermediate Aa-2 is replaced by intermediate Ca-2 to obtain intermediate Ca-3 (yield: 78%).

[0191] Synthesis of intermediate Ca-4: The synthesis of intermediate Ca-4 is the same as that of intermediate Aa-4, except that intermediate Aa-3 is replaced by intermediate Ca-3 to obtain intermediate Ca-4 (yield: 74%).

[0192] Synthesis of intermediate Ca-5: The synthesis of intermediate Ca-5 is the same as that of intermediate Aa-5, except that intermediate Aa-4 is replaced by intermediate Ca-4 to obtain intermediate Ca-5 (yield: 80%).

[0193] Synthesis of intermediate Ca-6: The synthesis of intermediate Ca-6 is the same as that of intermediate Aa-6, except that intermediate Aa-5 is replaced by intermediate Ca-5 to obtain intermediate Ca-6 (yield: 77%).

[0194] Synthesis of intermediate Ca-7: The synthesis of intermediate Ca-7 is the same as that of intermediate Aa-7, except that intermediate Aa-6 and intermediate N-1 are replaced by intermediate Ca-6 and intermediate N-4 to obtain intermediate Ca-7 (yield: 78%).

[0195] Synthesis of intermediate Ca-8: The synthesis of intermediate Ca-8 is the same as that of intermediate Aa-8, except that intermediate Aa-7 is replaced by intermediate Ca-7 to obtain intermediate Ca-8 (yield: 81%).

[0196] Synthesis of intermediate Ca: The synthesis of intermediate Ca is the same as that of intermediate Aa, except that intermediate Aa-8 is replaced by intermediate Ca-8 to obtain intermediate Ca (yield: 76%).

[0197] Mass spectrum: C27H9D5ClN3O, theoretical value: 436.11, found value: 436.10. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.14~7.24 (2H, m), 7.31~7.36 (1H, d), 7.37~7.44 (1H, m), 7.50~7.55 (1H, m), 8.05~8.08 (1H, d), 8.16~8.23 (1H, m), 8.33~8.38 (1H, d), 8.56~8.61 (1H, d).

[0198]

[0199] The synthesis method of intermediate Cb is the same as the synthesis method of Ca mentioned above, except that different raw materials are used to obtain intermediate Cb.

[0200] Mass spectrum: C27H9D5ClN3S, theoretical value: 452.09, found value: 452.10. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.12~7.22 (2H, m), 7.30~7.42 (2H, d), 7.53~7.58 (1H, d), 8.11~8.21 (2H, m), 8.37~8.42 (1H, d), 8.60~8.64 (1H, d).

[0201] Preparation Example 6

[0202]

[0203] Synthesis of intermediate Ea-1: The synthesis of intermediate Ea-1 is the same as that of intermediate Aa-5, except that intermediate Aa-4 and p-chlorophenylhydrazine hydrochloride are replaced by intermediate Ca-4 and phenylhydrazine hydrochloride to obtain intermediate Ea-1 (yield: 77%).

[0204] Synthesis of intermediate Ea-2: The synthesis of intermediate Ea-2 is the same as that of intermediate Aa-6, except that intermediate Aa-5 is replaced by intermediate Ea-1 to obtain intermediate Ea-2 (yield: 76%).

[0205] Synthesis of intermediate Ea-3: In a 500ml three-necked flask, under nitrogen protection, the intermediate Ea-2 (25mmol) was dissolved in N,N-dimethylformamide (100ml), and N,N-dimethylformamide solution (45ml) containing NBS (25mmol) was added dropwise. After the addition was completed, the temperature was raised to 100℃ and stirred for 18h. HPLC detection showed that the reaction of the raw materials was basically completed. The reaction solution was cooled to room temperature and water (200ml) was added dropwise. After stirring for 30min, the crude product was filtered and purified by column chromatography to obtain intermediate Ea-3 (yield 63%).

[0206] Synthesis of intermediate Ea-4: The synthesis of intermediate Ea-4 is the same as the synthesis method of intermediate Aa-7, except that intermediate Aa-6 and intermediate N-1 are replaced by intermediate Ea-3 and intermediate N-4 to obtain intermediate Ea-4 (yield: 80%).

[0207] Synthesis of intermediate Ea-5: The synthesis of intermediate Ea-5 is the same as that of intermediate Aa-8, except that intermediate Aa-7 is replaced by intermediate Ea-4 to obtain intermediate Ea-5 (yield: 86%).

[0208] Synthesis of intermediate Ea: The synthesis of intermediate Ea is the same as that of intermediate Aa, except that intermediate Aa-8 is replaced by intermediate Ea-5 to obtain intermediate Ea (yield: 78%).

[0209] Mass spectrum: C27H9D5BrN3O, theoretical value: 480.06, found value: 480.05. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.15~7.22 (4H, m), 7.38~7.42 (2H, m), 8.17~8.21 (2H, m), 8.28~8.31 (1H, s).

[0210] Example 1: Synthesis of Compound 2:

[0211]

[0212] Synthesis of intermediate 2-1: In a 500 mL three-necked flask, nitrogen was introduced, and intermediate Aa (36 mmol), 1,4-dioxane solvent (150 mL), diboron pinacol ester (72 mmol), potassium acetate (180 mmol) and [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (1.08 mmol) were added in sequence under stirring, and the temperature was raised to reflux for 5 h. HPLC detected that the reaction of the raw materials was complete. After the reaction solution was cooled to room temperature, the reaction solution was evaporated to dryness under reduced pressure to obtain a crude product. The crude product was dissolved in toluene solvent, heated with stirring, and heated to reflux. It was heated to a silica gel column for decolorization. The filtrate was evaporated to dryness under reduced pressure until a small amount of solvent remained. Ethanol (250 mL) was added for slurrying and recrystallized from toluene / ethanol to obtain intermediate 2-1 (yield: 87%).

[0213] Synthesis of Compound 2: In a 500 mL three-necked flask, under nitrogen, were added intermediate 2-1 (30 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (60 mmol), toluene (180 mL), dicyclohexyl(2',4',6'-triisopropyl-(1,1'-biphenyl)-2-yl)phosphonic acid (3 mmol), PD2(DBA)3 (tris(dibenzylideneacetone)dipalladium, 0.9 mmol), and 50 mL of an aqueous solution containing potassium dihydrogen phosphate (150 mol). Stirring was initiated and the mixture was heated to 90°C overnight. After 17 hours, the temperature was lowered to 40°C and then to 0°C for 3 hours. The crude product was filtered to obtain the crude product, which was then washed with water (270 mL) and then with methanol (270 mL). The resulting solid was separated by silica gel column chromatography using toluene as the eluent to obtain Compound 2 (yield: 90%).

[0214] Mass spectrum: C53H33N9O, theoretical value: 811.28, found value: 811.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.22~1.28 (1H, m), 3.32~3.41 (1H, m), 7.46~7.50 (8H, m), 7.50~7.53 (6H, m), 7.57~7.61 (2H, m), 8.32~8.36 (5H, m), 8.36~8.41 (3H, m), 8.55~8.59 (2H, m), 8.73~8.74 (1H, d), 8.82~8.85 (1H, d).

[0215] Example 2: Synthesis of Compound 16:

[0216]

[0217] Synthesis of intermediate 16-1: The synthesis method is the same as that of intermediate 2-1 to obtain intermediate 16-1 (yield: 85%).

[0218] Synthesis of Compound 16: The synthesis method was the same as that of Compound 2 to obtain Compound 16 (yield: 88%).

[0219] Mass spectrum: C63H38N6O2S, theoretical value: 875.26, found value: 875.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.40~7.44 (2H, m), 7.47~7.48 (1H, m), 7.49~7.54 (14H, m), 7.54~7.56 (1H, m), 7.80~7.84 (2H, d), 7.94~7.95 (1H, d), 7.99~8.07 (2H, m), 8.32~8.40 (8H, m), 8.63~8.67 (1H, d), 9.03~9.04 (1H, d).

[0220] Example 3: Synthesis of Compound 27:

[0221]

[0222] Synthesis of Intermediate 27-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 27-1 (yield: 83%).

[0223] Synthesis of Compound 27: The synthesis method was the same as that of Compound 2 to obtain Compound 27 (yield: 87%).

[0224] Mass spectrum: C43H26N6O, theoretical value: 642.22, found value: 642.25. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.61~2.63 (3H, s), 7.13~7.21 (2H, m), 7.22~7.23 (1H, m), 7.26~7.27 (1H, m), 7.37~7.41 (1H, s), 7.46~7.53 (7H, m), 7.56~7.60 (1H, d), 7.93~7.98 (2H, m), 8.15~8.22 (1H, m), 8.29~8.39 (6H, m), 8.48~8.52 (1H, d).

[0225] Example 4: Synthesis of Compound 57:

[0226]

[0227] Synthesis of Intermediate 57-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 57-1 (yield: 82%).

[0228] Synthesis of Compound 57: The synthesis method was the same as that of Compound 2 to obtain Compound 57 (yield: 90%).

[0229] Mass spectrum: C54H30D3N7S, theoretical value: 814.27, found value: 814.30. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.45~7.49 (2H, m), 7.49~7.57 (11H, m), 7.57~7.61 (3H, m), 7.91~7.97 (8H, m), 8.22~8.24 (2H, s), 8.49~8.55 (2H, m), 8.58~8.59 (1H, d), 8.75~8.79 (1H, d).

[0230] Example 5: Synthesis of Compound 73:

[0231]

[0232] Synthesis of Intermediate 73-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 73-1 (yield: 82%).

[0233] Synthesis of Compound 73: The synthesis method was the same as that of Compound 2 to obtain Compound 73 (yield: 89%).

[0234] Mass spectrum: C49H24D5N5O, theoretical value: 708.27, found value: 708.30. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.14~7.24 (2H, m), 7.37~7.44 (1H, m), 7.44~7.63 (9H, m), 7.67~7.74 (1H, m), 7.91~7.97 (4H, m), 8.17~8.24 (2H, m), 8.30~8.32 (1H, m), 8.35~8.41 (3H, m), 8.59~8.63 (1H, d).

[0235] Example 6: Synthesis of Compound 102:

[0236]

[0237] Synthesis of Intermediate 102-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 102-1 (yield: 81%).

[0238] Synthesis of Compound 102: The synthesis method was the same as that of Compound 2 to obtain Compound 102 (yield: 88%).

[0239] Mass spectrum: C55H26D5N7O, theoretical value: 810.29, found value: 810.30. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.44~7.49 (2H, s), 7.50~7.54 (3H, m), 7.55~7.58 (2H, m), 7.59~7.68 (5H, m), 7.75~7.82 (6H, m), 8.02~8.06 (2H, s), 8.10~8.14 (2H, s), 8.55~8.56 (1H, d), 8.73~8.77 (1H, d), 8.90~8.95 (1H, d), 9.60~9.62 (1H, d).

[0240] Example 7: Synthesis of Compound 114:

[0241]

[0242] Synthesis of Intermediate 114-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 114-1 (yield: 83%).

[0243] Synthesis of Compound 114: The synthesis method was the same as that of Compound 2 to obtain Compound 114 (yield: 91%).

[0244] Mass spectrum: C47H27N5S, theoretical value: 693.20, found value: 693.30. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.14-7.24 (2H, m), 7.38-7.46 (2H, m), 7.47-7.60 (5H, m), 7.61-7.73 (4H, m), 7.76-7.84 (4H, m), 7.94~7.98 (1H, m), 7.99~8.07 (2H, m), 8.11~8.15 (1H, m), 8.17~8.21 (1H , m), 8.32~8.34 (1H, m), 8.35~8.40 (1H, m), 8.44~8.48 (2H, m), 8.72~8.76 (1H, d).

[0245] Example 8: Synthesis of Compound 118:

[0246]

[0247] Synthesis of Intermediate 118-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 118-1 (yield: 82%).

[0248] Synthesis of Compound 118: The synthesis method was the same as that of Compound 2 to obtain Compound 118 (yield: 85%).

[0249] Mass spectrum: C45H31N5O, theoretical value: 657.25, found value: 657.30. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 1.34 ~ 1.36 (9H, s), 7.16 ~ 7.22 (2H, m), 7.38 ~ 7.42 (1H, d), 7.45 ~ 7.53 (5H, m), 7.57 ~ 7.69 (3H, m), 7.77 ~ 7.83 (2H, m), 8.04 ~ 8.08 (1H, m), 8.14 ~ 8.21 (2H, m), 8.31 ~ 8.39 (3H, m), 8.45 ~ 8.49 (1H, d), 8.67 ~ 8.68 (1H, d), 8.73 ~ 8.77 (1H, d).

[0250] Example 9: Synthesis of Compound 121:

[0251]

[0252] Synthesis of Intermediate 121-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 121-1 (yield: 81%).

[0253] Synthesis of Compound 121: The synthesis method was the same as that of Compound 2 to obtain Compound 121 (yield: 86%).

[0254] Mass spectrum: C47H22D5N5S, theoretical value: 698.23, found value: 698.25. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.14-7.21 (2H, m), 7.23-7.24 (1H, m), 7.26-7.28 (1H, m) 7.37-7.44 (2H, m), 7.45-7.5 8(2H,m), 7.61~7.69(2H,m), 7.76~7.84(4H,m), 7.93~8.00(3H,m), 8.11~8.15(1H , m), 8.17~8.21(1H,m), 8.34~8.38(1H,d), 8.55~8.56(1H,d), 8.61~8.65(1H,d).

[0255] Example 10: Synthesis of Compound 132:

[0256]

[0257] Synthesis of Intermediate 132-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 132-1 (yield: 80%).

[0258] Synthesis of Compound 132: The synthesis method was the same as that of Compound 2 to obtain Compound 132 (yield: 86%).

[0259] Mass spectrum: C41H18D5N5O, theoretical value: 606.22, found value: 606.20. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.14~7.24 (4H, m), 7.36~7.44 (2H, m), 7.45~7.58 (2H, m), 7.61~7.69 (2H, m), 7.76~7.83 (3H, m), 7.98~8.03 (1H, m), 8.11~8.15 (1H, m), 8.15~8.24 (2H, m), 8.69~8.70 (1H, s).

[0260] Example 11: Synthesis of Compound 139:

[0261]

[0262] Synthesis of Intermediate 139-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 139-1 (yield: 79%).

[0263] Synthesis of Compound 139: The synthesis method was the same as that of Compound 2 to obtain Compound 139 (yield: 88%).

[0264] Mass spectrum: C50H29N7O, theoretical value: 743.24, found value: 743.25. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.61~2.63 (3H, m), 7.28~7.36 (4H, m), 7.55~7.71 (8H, m), 7.76~7.84 (4H, m), 8.00~8.08 (6H, m), 8.13~8.17 (1H, m), 8.33~8.37 (1H, m), 8.56~8.60 (2H, m).

[0265] Example 12: Synthesis of Compound 153:

[0266]

[0267] Synthesis of Intermediate 153-1: The synthesis method was the same as that of Intermediate 2-1 to obtain Intermediate 153-1 (yield: 82%).

[0268] Synthesis of Compound 153: The synthesis method was the same as that of Compound 2 to obtain Compound 153 (yield: 87%).

[0269] Mass spectrum: C41H18D5N5O, theoretical value: 606.22, found value: 606.20. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.13 ~ 7.24 (2H, m), 7.28 ~ 7.43 (3H, m) 7.55 ~ 7.70 (4H, m), 7.76 ~ 7.83 (2H, m), 8.00 ~ 8.08 (3H, m), 8.14 ~ 8.23 ​​(1H, m), 8.33 ~ 8.34 (1H, d), 8.67 ~ 8.72 (1H, d), 8.76 ~ 8.78 (1H, d).

[0270] Device Example 1

[0271] The glass plates coated with an ITO transparent conductive layer were ultrasonically treated, rinsed in deionized water, ultrasonically degreased in a 1:1 acetone:ethanol mixed solvent, baked in a clean environment to completely remove moisture, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0272] The glass substrate with the anode was placed in a vacuum chamber and evacuated to 1×10 -4 Pa, HAT-CN was vacuum evaporated on the above anode layer as a hole injection layer at a deposition rate of 0.1 nm / s and a total deposition thickness of 5 nm; then NPB was evaporated at a deposition rate of 0.1 nm / s and a thickness of 60 nm; TCTA was vacuum evaporated on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a thickness of 10 nm;

[0273] The light-emitting layer of the device is vacuum-deposited on the hole transport layer. The light-emitting layer includes a host material and a guest material. The multi-source co-evaporation method is used to adjust the evaporation rate of the host material compound 2 to 0.1 nm / s, and the evaporation rate of the guest material (piq)2Ir(acac) is set at 5% of the evaporation rate of the host material. The total film thickness of the evaporation is 30 nm.

[0274] The hole blocking layer TPBi of the device was vacuum-deposited on top of the light-emitting layer at a rate of 0.1 nm / s and a thickness of 5 nm. The electron transport layer was then evaporated using a multi-source co-evaporation method, with the evaporation rate of both ET-1 and ET-2 adjusted to 0.1 nm / s, and the total film thickness was 30 nm.

[0275] LiF with a thickness of 1 nm was vacuum evaporated on the electron transport layer (ETL) as the electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.

[0276]

[0277] Device Examples 2 to 12

[0278] Organic light-emitting devices of Device Examples 2 to 12 were prepared using a method similar to that of Device Example 1, except that Compound 2 in Device Example 1 was replaced with the corresponding compound in Table 2.

[0279] Device Comparative Example 1

[0280] An organic electroluminescent device of Comparative Example 1 was prepared by a method similar to that of Device Example 1, except that Compound 2 in Device Example 1 was replaced by RH-1.

[0281]

[0282] Test Example 1

[0283] At a brightness of 2000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1 to 12 and device comparative example 1 were measured. The results are shown in Table 2.

[0284] Table 2

[0285] Red light main material Driving voltage (V) Efficiency (cd / A) <![CDATA[Brightness (cd / m 2 )]]> Device Example 1 Compound 2 4.46 11.9 2000 Device Example 2 Compound 16 4.42 11.6 2000 Device Example 3 Compound 27 4.38 10.5 2000 Device Example 4 Compound 57 4.33 11.5 2000 Device Example 5 Compound 73 4.35 10.3 2000 Device Example 6 Compound 102 4.03 12.8 2000 Device Example 7 Compound 114 4.07 11.3 2000 Device Example 8 Compound 118 4.12 11.0 2000 Device Example 9 Compound 121 4.17 10.8 2000 Device Example 10 Compound 132 4.20 10.7 2000 Device Example 11 Compound 139 4.23 12.5 2000 Device Example 12 Compound 153 4.28 10.4 2000 Device Comparative Example 1 RH-1 4.63 8.6 2000

[0286] It can be seen from the experimental results shown in Table 2 that when the compound of the present invention is used as the red light host material of the organic electroluminescent device, it has a lower driving voltage and a higher luminous efficiency compared with the prior art.

[0287] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, various simple variations of the technical solution of the present invention may be made, including combining the various technical features in any other appropriate manner. These simple variations and combinations should also be regarded as disclosed in the present invention and fall within the scope of protection of the present invention.

Claims

1. An organic compound, characterized in that The compound has the structure shown in formula (I): Wherein, in formula (I), X1 is O or S; X2 is C; X3 is N; R1 is selected from C 1-12 Alkyl, C 3-12 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl; R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), and a substituent represented by formula (Q5); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein each of the two is not simultaneously any one of the substituent represented by formula (Q1), the substituent represented by formula (Q2), the substituent represented by formula (Q3), the substituent represented by formula (Q4), and the substituent represented by formula (Q5); and when R 41 and R 42 When one of the substituents is a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), or a substituent represented by formula (Q5), R 21 、R 22 、R 31 、R 32 All are H; In formula (Q1), formula (Q2), formula (Q3), formula (Q4), and formula (Q5), wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene; At least two of Y1, Y2 and Y3 are N, and optionally the remaining one is C; R 51 and R 52 Each is independently selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl; R6 and R7 are each independently selected from H, phenyl, naphthyl, C 1-12 Alkyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl.

2. The compound according to claim 1, wherein In formula (I), X1 is O or S; X2 is C; X3 is N; R1 is selected from C 1-6 Alkyl, C 3-8 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl; R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), and a substituent represented by formula (Q5); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein each of the two is not simultaneously any one of the substituent represented by formula (Q1), the substituent represented by formula (Q2), the substituent represented by formula (Q3), the substituent represented by formula (Q4), and the substituent represented by formula (Q5); and when R 41 and R 42 When one of the substituents is a substituent represented by formula (Q1), a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), or a substituent represented by formula (Q5), R 21 、R 22 、R 31 、R 32 All are H; In formula (Q1), formula (Q2), formula (Q3), formula (Q4), and formula (Q5), wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene; At least two of Y1, Y2 and Y3 are N, and optionally the remaining one is C; R 51 and R 52 Each is independently selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl; R6 and R7 are each independently selected from H, phenyl, naphthyl, C 1-6 Alkyl, 9,9-dimethylfluorenyl, dibenzothiophene.

3. The organic compound according to claim 1 or 2, wherein In formula (I), X1 is O or S; X2 is C; X3 is N; R1 is selected from C 1-6 Alkyl, C 3-8 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl; R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q1); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 In the formula (Q1), each of the two is not the same; and when R 41 and R 42 When one of them is a substituent represented by formula (Q1), R 21 、R 22 、R 31 、R 32 All are H; In formula (Q1), wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene; At least two of Y1, Y2 and Y3 are N, and optionally the remaining one is C; R 51 and R 52 Each is independently selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, and 9,9-dimethylfluorenyl.

4. The organic compound according to claim 1 or 2, wherein In formula (I), X1 is O or S; X2 is C; X3 is N; R1 is selected from C 1-6 Alkyl, C 3-8 Cycloalkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, deuterated C 1-6 Alkyl, deuterated C 1-6 Any one of cycloalkyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl; R 21 、R 22 、R 31 、R 32 、R 41 and R 42 are each independently selected from H, a substituent represented by formula (Q2), a substituent represented by formula (Q3), a substituent represented by formula (Q4), and a substituent represented by formula (Q5); and R 21 and R 22 , R 31 and R 32 , R 41 and R 42 wherein each of the two is not simultaneously any one of the substituent represented by formula (Q2), the substituent represented by formula (Q3), the substituent represented by formula (Q4), and the substituent represented by formula (Q5); and when R 41 and R 42 When one of the substituents is any one of the substituents represented by formula (Q2), the substituents represented by formula (Q3), the substituents represented by formula (Q4), and the substituents represented by formula (Q5), R 21 、R 22 、R 31 、R 32 All are H; In formula (Q2), formula (Q3), formula (Q4), and formula (Q5), wherein L is present or absent, and the optional L is a linking group provided by at least one structure selected from benzene, biphenyl, naphthalene, dibenzofuran, and dibenzothiophene; R6 and R7 are each independently selected from H, phenyl, naphthyl, C 1-6 Alkyl, 9,9-dimethylfluorenyl, dibenzothiophene.

5. An organic compound, characterized in that The organic compound is selected from any one of the following:

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

7. An organic electroluminescent device comprising one or more organic compounds selected from the group consisting of the organic compounds of claims 1 to 5, characterized in that: The organic compound is present in the light-emitting layer of the organic electroluminescent device.

8. The organic electroluminescent device according to claim 7, wherein: The organic compound serves as a red light host material and exists in the light-emitting layer of the organic electroluminescent device.

9. The organic electroluminescent device according to claim 7 or 8, wherein: The organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer which are stacked in sequence.

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