Anthracene organic compound and application thereof

Abstract

The invention provides an anthracene organic compound and application thereof. The anthracene organic compound has a structure as shown in a formula I. In the invention, the anthracene organic compound which can be used as a blue fluorescence electroluminescent material is obtained by designing the structure of the anthracene organic compound, and the comprehensive performance of the organic electroluminescent device can be further improved by taking the anthracene organic compound as a luminescent layer main body material.

Description

Technical Field

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

[0002] Organic electroluminescent (OLED) display technology is a new generation of display technology based on electroluminescence after CRT and LCD. As a new generation of display technology, it has the advantages of good display effect, low power consumption, high flexibility and ultra-thinness, and is widely used in mobile phones, cars, smart wearable devices and other product screens.

[0003] The basic device structure of OLED includes cathode, electron injection layer, electron transport layer, organic light-emitting layer, hole transport layer, hole injection layer, anode and substrate. The color of OLED light depends on the type of organic molecules in the light-emitting layer. Placing several organic films on the same OLED will form a color display. The brightness or intensity of light depends on the performance of the light-emitting material and the size of the applied current. For the same OLED, the greater the current, the higher the brightness of the light.

[0004] At present, various new organic electroluminescent materials with excellent performance have been developed one after another, but with the rapid development of information technology, people have also put forward new goals and requirements for the performance of information display systems, especially in terms of efficiency, life, voltage, etc. Therefore, how to design a new organic electroluminescent material to meet the needs of its use in high-performance OLED devices is a key research topic for researchers in this field. Summary of the invention

[0005] In view of the shortcomings of the prior art, the purpose of the present invention is to provide an anthracene organic compound and its application. In the present invention, by designing the structure of the anthracene organic compound, an anthracene organic compound that can be used as a main material of the light-emitting layer is obtained. By using the anthracene organic compound as the main material of the light-emitting layer, the comprehensive performance of the organic electroluminescent device can be further improved.

[0006] To achieve this object, the present invention adopts the following technical solutions:

[0007] In a first aspect, the present invention provides an anthracene organic compound having a structure shown in the following formula I:

[0008]

[0009] Wherein, Ar1 is selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene group, a benzofuranyl group or a benzothiophenyl group;

[0010] Ar2 is selected from a single bond or a substituted or unsubstituted C6-C20 arylene group;

[0011] R1-R4 are each independently selected from any one of a hydrogen atom, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C6-C30 heteroaryl group;

[0012] The substituents in Ar1, Ar2, R1-R4 are each independently selected from any one of -F, -CN, a deuterium atom, a C1-C10 alkyl group or a C6-C20 aryl group.

[0013] In the present invention, anthracene organic compounds that can be used as blue fluorescent electroluminescent materials are obtained by designing the structure of anthracene organic compounds. The anthracene organic compounds are used as the main material of the light-emitting layer, which not only prolongs the luminous life of the device but also ensures that the luminous efficiency does not decrease. At the same time, the driving voltage is optimized and the energy consumption is reduced, so that the organic electroluminescent device has significant improvements in driving voltage, luminous efficiency, luminous life, etc.

[0014] It should be noted that, in the present invention, if R1 and R2 are both hydrogen atoms, Ar1 is selected from any one of a single bond, a substituted or unsubstituted C6-C20 aryl group, a benzofuranyl group or a benzothiophenyl group. Similarly, if R3 and R4 are both hydrogen atoms, Ar2 is selected from a single bond or a substituted or unsubstituted C6-C20 aryl group.

[0015] It should be noted that, in the present invention, "D" represents a deuterium atom, and the same applies hereinafter.

[0016] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0017] As a preferred technical solution of the present invention, the compound of formula I meets at least one of the following conditions:

[0018] (1) The compound of formula I does not contain deuterium atoms;

[0019] (2) In the compound of formula I, all hydrogen atoms on R1 and R2 are replaced by deuterium atoms;

[0020] (3) In the compound of formula I, Ar1 is not a single bond, and all hydrogen atoms on Ar1 are replaced by deuterium atoms;

[0021] (4) In the compound of formula I, all hydrogen atoms on the anthracene ring are replaced by deuterium atoms;

[0022] (5) In the compound of formula I, Ar2 is not a single bond, and all hydrogen atoms on Ar2 are replaced by deuterium atoms;

[0023] (6) In the compound of formula I, all hydrogen atoms on R3 and R4 are replaced by deuterium atoms.

[0024] Preferably, the compound of formula I meets conditions (2) and (3).

[0025] As a preferred technical solution of the present invention, the C6-C20 arylene group is selected from any one of a phenylene group, a naphthylene group, a biphenylene group or a terphenylene group.

[0026] Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl or terphenyl.

[0027] Preferably, the C6-C30 heteroaryl group is selected from any one of benzofuranyl, benzothiophenyl, naphthobenzofuranyl, dibenzofuranyl and dibenzothiophenyl.

[0028] Preferably, the C1-C10 alkyl group is selected from any one of methyl, ethyl, propyl, butyl and cyclohexyl.

[0029] As a preferred technical solution of the present invention, Ar1 is selected from any one of a single bond, a phenylene group, a benzofuranyl group or a benzothiophenyl group.

[0030] Preferably, said R1 is selected from a hydrogen atom.

[0031] Preferably, R2 is selected from any one of naphthoxybenzofuranyl, benzofuranyl, dibenzofuranyl and dibenzothiophenyl.

[0032] Preferably, Ar2 is selected from a single bond or a phenylene group.

[0033] Preferably, said R3 is selected from a hydrogen atom.

[0034] Preferably, said R2 is selected from naphthyl.

[0035] As a preferred technical solution of the present invention, the compound of formula I includes the following substituted or unsubstituted compounds:

[0036]

[0037]

[0038] Wherein, X1-X7 are each independently selected from O or S;

[0039] The substitution means that the hydrogen atoms in the above compounds can be independently replaced by deuterium atoms (-D, the same below).

[0040] As a preferred technical solution of the present invention, all hydrogen atoms on the anthracene group in the compound of formula I are replaced by deuterium atoms.

[0041] Preferably, all hydrogen atoms on Ar1 in the compound of formula I are replaced by deuterium atoms.

[0042] Preferably, in the compound of formula I, all hydrogen atoms on R1 and R2 are replaced by deuterium atoms.

[0043] Preferably, the compound of formula I includes the following substituted or unsubstituted compounds:

[0044]

[0045] Wherein, X1-X7 are each independently selected from O or S;

[0046] The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

[0047] In the present invention, deuterium atoms are introduced into specific sites in the compound of formula I. Since the carbon-deuterium bond has a short bond length and a large bond energy, the energy of the luminescent material is reduced, thereby significantly enhancing the stability and life of the luminescent device.

[0048] It should be noted that, in the compound of formula I, (D) 4 means that the corresponding 4 hydrogen atoms on the benzene ring are replaced by deuterium atoms, (D) 3 means that the corresponding 3 hydrogen atoms on the benzene ring are replaced by deuterium atoms, and (D) 6 means that the corresponding 6 hydrogen atoms on the naphthalene ring are replaced by deuterium atoms.

[0049] As a preferred technical solution of the present invention, the compound of formula I is selected from any one of compounds 1-178:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] Preferably, the compound of formula I is selected from any one of the following compounds:

[0062]

[0063] In a second aspect, the present invention provides an intermediate, wherein the intermediate comprises the following substituted or unsubstituted compound:

[0064]

[0065] Wherein, Y1, Y4, Y5, and Y6 each independently represent a halogen atom, preferably Br or I;

[0066] Y2 and Y3 are each independently selected from any one of a hydrogen atom, a halogen atom, or -B(OH)2;

[0067] The substitution means that the hydrogen atoms in the above compounds can each independently be replaced by deuterium atoms;

[0068] The intermediate is used to prepare the anthracene organic compound as described in the second aspect.

[0069] Preferably, Y1, Y4, Y5 and Y6 each independently represent Br or I.

[0070] Preferably, the intermediate includes the following compounds:

[0071]

[0072]

[0073] It should be noted that there is no special limitation on the preparation methods of the compound of formula I and the intermediates mentioned above in the present invention, and the commonly used preparation methods in the art are applicable.

[0074] In a third aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode;

[0075] The material of the organic thin film layer includes at least one anthracene organic compound as described in the first aspect.

[0076] As a preferred technical solution of the present invention, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer comprises at least one anthracene organic compound as described in the first aspect;

[0077] Preferably, the organic thin film layer further includes at least one of a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0078] The method for manufacturing the organic electroluminescent device comprises the following steps:

[0079] (1) The anode material is laminated onto the surface of the substrate by conventional methods to form an anode. The substrate used is a glass substrate or a transparent plastic substrate with good transparency, surface smoothness, operability and water resistance. In addition, the anode material can be transparent and conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc.

[0080] (2) vacuum thermal deposition or spin coating of a hole injection layer material (HIL) on the surface of the anode by conventional methods to form a hole injection layer;

[0081] The hole injection layer material can be CuPc, m-MTDATA, m-MTDAPB, TCTA of star amine, 2-TNATA, or IDE406'' available from Idemitsu Kosan Co., Ltd. of Japan.

[0082] (3) vacuum thermal deposition or spin coating of a hole transport layer material (HTL) on the surface of the hole injection layer by conventional methods to form a hole transport layer;

[0083] The hole transport layer material can be α-NPD, NPB or TPD;

[0084] (4) vacuum thermal deposition or spin coating of an emitting layer material (EML) on the surface of the hole transport layer by conventional methods to form an emitting layer;

[0085] Furthermore, an electron blocking layer (EBL) may be added between the hole transport layer and the light emitting layer.

[0086] (5) vacuum thermal deposition or spin coating of an electron transport layer material (ETL) on the surface of the light-emitting layer by conventional methods to form an electron transport layer;

[0087] There is no particular limitation on the electron transport layer material in the present invention, and exemplary materials include: Alq3;

[0088] Furthermore, a hole blocking layer (HBL) can be added between the light-emitting layer and the electron transport layer, and phosphorescent dopants can be used together in the light-emitting layer to prevent triplet excitons from diffusing to the electron transport layer.

[0089] A hole blocking layer material (HBL) is vacuum thermally deposited or spin-coated on the surface of the light-emitting layer by a conventional method to form a hole blocking layer;

[0090] The present invention has no particular limitation on the hole blocking layer material, which exemplarily includes but is not limited to: Liq, 2-methyl-8-hydroxyquinoline p-hydroxybiphenyl aluminum, BCP, etc.;

[0091] (6) vacuum thermal deposition or spin coating of an electron injection layer material (EIL) on the surface of the electron transport layer by conventional methods to form an electron injection layer;

[0092] The electron injection layer material can be LiF, Liq, Li2O, BaO, NaCl or CsF, etc.

[0093] (7) vacuum thermal deposition or spin coating of cathode material on the electron injection layer by conventional methods to form a cathode;

[0094] The cathode material can be Li, Al, Al-Li or Ca, etc.

[0095] In addition, organic electroluminescent devices use indium tin oxide (ITO) or indium zinc oxide (IZO) to make a light-transmitting transparent cathode.

[0096] According to the above-mentioned method for manufacturing an organic electroluminescent device, it can be manufactured in the order of anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode. Similarly, it can also be manufactured in the order of cathode / electron injection layer / electron transport layer / light-emitting layer / hole transport layer / hole injection layer / anode.

[0097] Compared with the prior art, the present invention has the following beneficial effects:

[0098] In the present invention, by designing the structure of anthracene organic compounds, anthracene organic compounds that can be used as blue fluorescent electroluminescent materials are obtained. Using the anthracene organic compounds as the main material of the light-emitting layer, an organic electroluminescent device with lower driving voltage, higher luminous effect and longer service life is prepared. DETAILED DESCRIPTION

[0099] For the convenience of understanding the present invention, the present invention lists the following embodiments. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0100] Preparation Example 1

[0101] This preparation example provides an intermediate 1 and a synthesis method thereof, and the synthesis method is as follows:

[0102]

[0103] Under nitrogen protection, 2.52 g (10 mmol) of 1-chloropyrano[2,3,-B]benzofuran and 0.13 g (1 mmol) of aluminum chloride were dissolved in 8.40 g (100 mmol) of deuterated benzene and reacted at 25 °C for 6 h.

[0104] After the reaction was completed, 50 mL of 5% potassium carbonate solution was added to quench the reaction, and the reaction solution was extracted with 100 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether: dichloromethane = 10:1 (volume ratio) to obtain 2.27 g of intermediate 1 (yield: 88%).

[0105] The intermediate 1 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 1 was 261 (M+).

[0106] Preparation Example 2

[0107] This preparation example provides an intermediate 2 and a synthesis method thereof, and the synthesis method is as follows:

[0108]

[0109] Under nitrogen protection, 2.96 g (10 mmol) of 1-bromopyrano[2,3,-B]benzofuran, 1.66 g (10.2 mmol) of benzofuran-2-boric acid, 2.07 g (15 mmol) of potassium carbonate, and 0.14 g of tetrakistriphenylphosphine palladium were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water. The reaction system was heated to 85 °C and reacted for 6 h.

[0110] After the reaction, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 6:1 (volume ratio) to obtain 2.68 g of intermediate 2 (yield 81%).

[0111] The intermediate 2 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 2 was 334 (M+).

[0112] Preparation Example 3

[0113] This preparation example provides an intermediate 3 and a synthesis method thereof, and the synthesis method is as follows:

[0114]

[0115] Referring to the synthesis method of intermediate 2, the only difference is that 1-bromopyrano[2,3,-B]benzofuran is replaced by an equal amount of 1-bromodibenzofuran, and the other conditions are the same as those in Preparation Example 2.

[0116] The intermediate 3 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 3 was 284 (M+).

[0117] Preparation Example 4

[0118] This preparation example provides an intermediate 4 and a synthesis method thereof, and the synthesis method is as follows:

[0119]

[0120] Under nitrogen protection, 2.30 g (10 mmol) of 3-bromo-2-chlorobenzofuran, 2.65 g (10.1 mmol) of naphtho[2,3-B]benzofuran-1-boronic acid, 2.07 g (15 mmol) of potassium carbonate, and 0.14 g of tetrakistriphenylphosphine palladium were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water, and the reaction system was heated to 85 ° C and reacted for 6 hours;

[0121] After the reaction was completed, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 5:1 (volume ratio) to obtain 2.60 g of intermediate 4 (yield 71%).

[0122] The intermediate 4 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 4 was 368 (M+).

[0123] Preparation Example 5

[0124] This preparation example provides an intermediate 5 and a synthesis method thereof, and the synthesis method is as follows:

[0125]

[0126] Referring to the synthesis method of intermediate 4, the only difference is that naphtho[2,3-B]benzofuran-1-boric acid is replaced by an equal amount of dibenzofuran-2-boric acid, and the other conditions are the same as those in Preparation Example 4.

[0127] The intermediate 5 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 5 was 318 (M+).

[0128] Preparation Example 6

[0129] This preparation example provides an intermediate 6 and a synthesis method thereof, and the synthesis method is as follows:

[0130]

[0131] Under nitrogen protection, 3.34 g (10 mmol) of intermediate 2, 0.34 g of platinum carbon, and 16.5 g of deuterated water were placed in an autoclave, and the reaction system was heated to 185 °C and reacted for 12 h;

[0132] After the reaction, the temperature of the reaction system was lowered to 25°C, the solid was filtered out, dissolved in 50 mL of toluene, and the platinum carbon was filtered out. The liquid was concentrated and passed through a silica gel column, eluted with petroleum ether: ethyl acetate = 6:1 (volume ratio), and 3.14 g of intermediate 6 was obtained (yield was 90%).

[0133] The intermediate 6 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 6 was 348 (M+).

[0134] Preparation Example 7

[0135] This preparation example provides an intermediate 7 and a synthesis method thereof, and the synthesis method is as follows:

[0136]

[0137] Referring to the synthesis method of intermediate 6, the only difference is that intermediate 2 is replaced by intermediate 3 of the same amount, and the other conditions are the same as those of Preparation Example 6.

[0138] The intermediate 7 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 7 was 296 (M+).

[0139] Preparation Example 8

[0140] This preparation example provides an intermediate 8 and a synthesis method thereof, and the synthesis method is as follows:

[0141]

[0142] The synthetic method of intermediate 1 is referred to, the only difference is that 1-chloropyrano[2,3,-B]benzofuran is replaced by an equal amount of intermediate 4, and the other conditions are the same as those in Preparation Example 6.

[0143] The intermediate 8 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 8 was 381 (M+).

[0144] Preparation Example 9

[0145] This preparation example provides an intermediate 9 and a synthesis method thereof, and the synthesis method is as follows:

[0146]

[0147] The synthetic method of intermediate 1 is referred to, the only difference is that 1-chloropyrano[2,3,-B]benzofuran is replaced by an equal amount of intermediate 5, and the other conditions are the same as those in Preparation Example 6.

[0148] The intermediate 9 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the intermediate 9 was 329 (M+).

[0149] Example 1

[0150] This example provides compound 1 and a synthesis method thereof, and the synthesis method is as follows:

[0151]

[0152] (1) Synthesis of Compound 1-1

[0153] Under nitrogen protection, 1.80 g (10 mmol) of deuterated 2-naphthaleneboronic acid, 3.10 g (11 mmol) of m-bromoiodobenzene, 2.07 g (15 mmol) of potassium carbonate, and 0.14 g of tetrakistriphenylphosphine palladium were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water. The reaction system was heated to 85 ° C and reacted for 6 hours.

[0154] After the reaction was completed, the temperature of the reaction system was lowered to 25° C., 50 mL of water was added, the liquid was separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate=15:1 (volume ratio) to obtain 2.21 g of compound 1-1 (yield: 77%);

[0155] Compound 1-1 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 1-1 was 289 (M+).

[0156] (2) Synthesis of Compound 1-2

[0157] Under nitrogen protection, 2.90 g (10 mmol) of compound 1-1, 2.25 g (1.01 mmol) of 9-anthraceneboric acid, 2.07 g (15 mmol) of potassium carbonate, and 0.14 g of tetrakistriphenylphosphine palladium were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water, and the reaction system was heated to 85 ° C and reacted for 6 hours;

[0158] After the reaction was completed, the temperature of the reaction system was lowered to 25° C., 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate=11:1 (volume ratio) to obtain 2.66 g of compound 1-2 (yield: 69%);

[0159] Compound 1-2 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 1-2 was 387 (M+).

[0160] (3) Synthesis of Compound 1-3

[0161] 3.87 g (10 mmol) of compound 1-2 and 1.96 g (1.1 mmol) of NBS were dissolved in 38 mL of tetrahydrofuran, and the reaction system was heated to 55 °C and reacted for 2 h;

[0162] After the reaction was completed, the temperature of the reaction system was lowered to 25° C., 120 mL of water was added, and the mixture was filtered. The filter cake was eluted with petroleum ether:ethyl acetate=9:1 (volume ratio) to obtain 4.11 g of compound 1-3 (yield: 89%);

[0163] Compound 1-3 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 1-3 was 465 (M+).

[0164] (4) Synthesis of Compound 1-4

[0165] 4.65 g (10 mmol) of compound 1-3 was dissolved in 50 mL of tetrahydrofuran, cooled to -80°C with liquid nitrogen under nitrogen protection, 8.65 mL (13 mmol) of n-butyl lithium was added dropwise, and after the addition was completed, the temperature was kept at -80°C for 1.5 h. 6.02 g (15 mmol) of tributyl borate was added dropwise at -80°C, and after the addition was completed, the temperature was raised to -10°C and kept for 2.5 h, and the reaction was completed.

[0166] After the reaction, 3% by mass of dilute hydrochloric acid was added at -10°C to a pH of 4 in the reaction system, the temperature was raised to 25°C, the liquids were separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phase was washed 3 times with saturated brine until the aqueous phase was neutral (pH = 7), the organic phases were combined, concentrated until a large amount of solid precipitated, 400 mL of n-heptane was added, the temperature was raised to 60°C, and slurrying was performed for 1 h to obtain 2.52 g of compound 1-4 (yield was 59%).

[0167] Compounds 1-4 were characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 1-4 was 431 (M+).

[0168] (5) Synthesis of Compound 1

[0169] Under nitrogen protection, 4.31 g (10 mmol) of compound 1-4, 2.55 g (1.01 mmol) of 1-chloropyrano[2,3,-B]benzofuran, 2.07 g (30 mmol) of potassium phosphate, 0.09 g (0.1 mmol) of tris(dibenzylideneacetone)dipalladium, and 0.10 g (0.2 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were dissolved in 50 mL of toluene, and the reaction system was heated to 110°C and reacted for 16 h.

[0170] After the reaction, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 5:1 (volume ratio) to obtain 3.41 g of compound 1 (yield 57%).

[0171] Compound 1 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 1 was 603 (M+).

[0172] Example 2

[0173] This example provides compound 65 and its synthesis method, the synthesis method is as follows:

[0174]

[0175] Referring to the synthesis method of compound 1, the m-bromoiodobenzene in step (1) was replaced with an equal amount of p-bromoiodobenzene to finally prepare compound 65;

[0176] Compound 65 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 65 was 603 (M+).

[0177] Example 3

[0178] This example provides compound 81 and its synthesis method, the synthesis method is as follows:

[0179]

[0180] (1) Synthesis of Compound 81-1

[0181] Under nitrogen protection, 2.22 g (10 mmol) of 9-anthraceneboric acid, 2.55 g (1.01 mmol) of 1-chloropyrano[2,3,-B]benzofuran, 2.07 g (30 mmol) of potassium phosphate, 0.09 g (0.1 mmol) of tris(dibenzylideneacetone)dipalladium, and 0.10 g (0.2 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were dissolved in 50 mL of toluene, and the reaction system was heated to 115°C and reacted for 12 h.

[0182] After the reaction, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 10:1 (volume ratio) to obtain 3.27 g of compound 1 (yield: 83%).

[0183] Compound 1 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 81-1 was 394 (M+).

[0184] (2) Synthesis of Compound 81-2

[0185] 3.94 g (10 mmol) of compound 81-1 and 1.96 g (1.1 mmol) of NBS were dissolved in 40 mL of tetrahydrofuran, and the reaction system was heated to 55° C. and reacted for 2 h;

[0186] After the reaction was completed, the temperature of the reaction system was lowered to 25° C., 120 mL of water was added, and the mixture was filtered. The filter cake was eluted with petroleum ether:ethyl acetate=10:1 (volume ratio) to obtain 4.33 g of compound 1-3 (yield: 92%).

[0187] Compound 81-2 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 81-2 was 472 (M+).

[0188] (3) Synthesis of Compound 81-3

[0189] 4.72 g (10 mmol) of compound 81-2 was dissolved in 50 mL of tetrahydrofuran, and the temperature was lowered to -80°C with liquid nitrogen under nitrogen protection. 8.65 mL (13 mmol) of n-butyl lithium was added dropwise, and the temperature was kept at -80°C for 1.5 h after the addition was completed. 6.02 g (15 mmol) of tributyl borate was added dropwise at -80°C, and the temperature was raised to -10°C and the temperature was kept at -10°C for 2.5 h after the addition was completed. The reaction was completed.

[0190] After the reaction, 3% by mass of dilute hydrochloric acid was added at -10°C to pH = 4, the temperature was raised to 25°C, the liquids were separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phase was washed three times with saturated brine until the aqueous phase was neutral (pH = 7), the organic phases were combined, concentrated until a large amount of solid precipitated, 300 mL of n-heptane was added, the temperature was raised to 70°C, and slurrying was performed for 1 h to obtain 2.22 g of compound 81-3 (yield was 51%).

[0191] Compound 81-3 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 81-3 was 438 (M+).

[0192] (4) Synthesis of Compound 81-4

[0193] Under nitrogen protection, 4.38 g (10 mmol) of compound 81-3, 3.10 g (1.02 mmol) of o-bromoiodobenzene, 2.07 g (15 mmol) of potassium carbonate, and 0.14 g of tetrakistriphenylphosphine palladium were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water. The reaction system was heated to 85 °C and reacted for 8 h.

[0194] After the reaction was completed, the temperature of the reaction system was lowered to 25° C., 50 mL of water was added, and the organic layer was dried and concentrated over anhydrous magnesium sulfate, and eluted with petroleum ether:ethyl acetate=6:1 (volume ratio) to obtain 3.92 g of compound 81-4 (yield: 72%);

[0195] Compound 81-4 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 81-4 was 548 (M+).

[0196] (5) Synthesis of Compound 81

[0197] Under nitrogen protection, 5.48 g (10 mmol) of compound 81-4, 2.69 g (15 mmol) of deuterated 2-naphthaleneboronic acid, 4.14 g (30 mmol) of potassium carbonate, and 0.04 g (0.05 mmol) of dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water. The reaction system was heated to 85 ° C and reacted for 12 h.

[0198] After the reaction, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 5:1 (volume ratio) to obtain 2.90 g of compound 81 (yield 48%).

[0199] Compound 81 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 81 was 603 (M+).

[0200] Example 4

[0201] This example provides compound 13 and its synthesis method, the synthesis method is as follows:

[0202]

[0203] Referring to the synthesis method of compound 1, the deuterated 2-naphthaleneboronic acid in step (1) is replaced with an equal amount of 2-naphthaleneboronic acid, and the m-bromoiodobenzene is replaced with an equal amount of deuterated p-bromoiodobenzene to obtain compound 13-1;

[0204] The compound 1-1 in step (2) is replaced by an equal amount of the compound 13-1, and the 9-anthracene boronic acid is replaced by an equal amount of deuterated-9-anthracene boronic acid to obtain the compound 13-2;

[0205] Accordingly, the compound 1-2 in step (3) is replaced by an equal amount of compound 13-2 to obtain compound 13-3; the compound 1-3 in step (4) is replaced by an equal amount of compound 13-3 to obtain compound 13-4; the compound 1-4 in step (5) is replaced by an equal amount of compound 13-4 to finally prepare compound 13;

[0206] Compound 13 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the tested compound 13 was 617 (M+).

[0207] Example 5

[0208] This example provides compound 29 and its synthesis method, the synthesis method is as follows:

[0209]

[0210] Referring to the synthesis method of compound 65, the deuterated 2-naphthaleneboronic acid in step (1) is replaced with an equal amount of 2-naphthaleneboronic acid, and p-bromoiodobenzene is replaced with an equal amount of deuterated p-bromoiodobenzene to obtain compound 29-1; the compound 65-1 in step (2) is replaced with an equal amount of compound 29-1, and 9-anthraceneboronic acid is replaced with an equal amount of deuterated 9-anthraceneboronic acid to obtain compound 13-2;

[0211] Accordingly, the compound 65-2 in step (3) is replaced by an equal amount of compound 29-2 to obtain compound 29-3; the compound 65-3 in step (4) is replaced by an equal amount of compound 29-3 to obtain compound 29-4;

[0212] The compound 65-4 in step (5) is replaced with an equal amount of the compound 29-4, and the 1-chloropyrano[2,3,-B]benzofuran is replaced with an equal amount of deuterated 1-chloropyrano[2,3,-B]benzofuran to finally prepare the compound 29;

[0213] Compound 29 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the tested compound 29 was 617 (M+).

[0214] Example 6

[0215] This example provides compound 46 and its synthesis method, the synthesis method is as follows:

[0216]

[0217] Referring to the synthesis method of compound 81, the 1-chloropyrano[2,3,-B]benzofuran in step (1) was replaced with an equal amount of deuterated 1-chloropyrano[2,3,-B]benzofuran, and the 9-anthraceneboronic acid was replaced with an equal amount of deuterated-9-anthraceneboronic acid to obtain compound 46-1;

[0218] Accordingly, the compound 81-1 in step (2) is replaced by an equal amount of compound 46-1 to obtain compound 46-2; the compound 81-2 in step (3) is replaced by an equal amount of compound 46-2 to obtain compound 46-3;

[0219] The compound 81-3 in step (4) is replaced with an equal amount of compound 46-3, and the o-bromoiodobenzene is replaced with an equal amount of deuterated o-bromoiodobenzene to obtain compound 46-4; the compound 81-4 in step (5) is replaced with an equal amount of compound 46-4, and the deuterated 2-naphthaleneboric acid is replaced with an equal amount of 2-naphthaleneboric acid to finally prepare compound 46;

[0220] Compound 46 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of compound 46 was 617 (M+).

[0221] Example 7

[0222] This example provides compound 98 and its synthesis method, the synthesis method is as follows:

[0223]

[0224] (1) Synthesis of Compound 98-1

[0225] 3.34 g (10 mmol) of intermediate 2 was dissolved in 50 mL of tetrahydrofuran, and 2.14 g (12 mmol) of NBS was added after the mixture was dissolved. The reaction system was heated to 55 °C and reacted for 4 h.

[0226] After the reaction was completed, the temperature of the reaction system was lowered to 25° C., 200 mL of water was added, and the mixture was filtered. The filter cake was eluted with petroleum ether:ethyl acetate=5:1 (volume ratio) to obtain 3.73 g of compound 98-1 (yield: 92%).

[0227] Compound 98-1 was characterized using a fast atom bombardment mass spectrometer, and the MS (FAB) of the test compound 98-1 was 412 (M+).

[0228] (2) Synthesis of Compound 98

[0229] Under nitrogen protection, 4.12 g (10 mmol) of compound 98-1, 4.18 g (12 mmol) of 10-(2-naphthyl)anthracene-9-boric acid, 2.07 g (15 mmol) of potassium carbonate, and 0.14 g of tetrakistriphenylphosphine palladium were dissolved in 50 mL of toluene, 20 mL of ethanol, and 20 mL of water, and the reaction system was heated to 85 ° C and reacted for 8 hours;

[0230] After the reaction, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 3:1 (volume ratio) to obtain 3.85 g of compound 98 (yield: 61%).

[0231] Compound 98 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of compound 98 was 636 (M+).

[0232] Example 8

[0233] This example provides compound 99 and its synthesis method, the synthesis method is as follows:

[0234]

[0235] Under nitrogen protection, 3.68 g (10 mmol) of intermediate 4, 4.18 g (12 mmol) of 10-(2-naphthyl)anthracene-9-boric acid, 2.07 g (30 mmol) of potassium phosphate, 0.09 g (0.1 mmol) of tris(dibenzylideneacetone)dipalladium, and 0.10 g (0.2 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were dissolved in 50 mL of toluene, and the reaction system was heated to 110°C and reacted for 16 h.

[0236] After the reaction, the temperature of the reaction system was lowered to 25°C, 50 mL of water was added, the liquids were separated, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and eluted with petroleum ether:ethyl acetate = 3:1 (volume ratio) to obtain 3.41 g of compound 99 (yield 51%).

[0237] Compound 99 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 99 was 636 (M+).

[0238] Example 9

[0239] This example provides compound 106 and its synthesis method, which is as follows:

[0240]

[0241] Referring to the synthesis method of compound 98, intermediate 2 was replaced with an equal amount of intermediate 6 to finally prepare compound 106.

[0242] Compound 106 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 106 was 649 (M+).

[0243] Example 10

[0244] This example provides compound 118 and its synthesis method, which is as follows:

[0245]

[0246] Referring to the synthesis method of compound 98, compound 98-1 was replaced with an equal amount of compound 106-1 to finally prepare compound 106.

[0247] Compound 118 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 118 was 664 (M+).

[0248] Embodiment 11

[0249] This example provides compound 122 and its synthesis method, the synthesis method is as follows:

[0250]

[0251] Referring to the synthesis method of compound 98, intermediate 2 was replaced with an equal amount of intermediate 7, and 10-(2-naphthyl)anthracene-9-boric acid was replaced with an equal amount of deuterated 10-(2-naphthyl)anthracene-9-boric acid to finally prepare compound 122.

[0252] Compound 122 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of the test compound 122 was 612 (M+).

[0253] Example 12

[0254] This example provides compound 107 and its synthesis method, which is as follows:

[0255]

[0256] Referring to the synthesis method of compound 99, intermediate 4 was replaced with an equal amount of intermediate 8 to prepare compound 107.

[0257] Compound 107 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 107 was 649 (M+).

[0258] Embodiment 13

[0259] This example provides compound 119 and its synthesis method, which is as follows:

[0260]

[0261] Referring to the synthesis method of compound 99, intermediate 4 was replaced with an equal amount of intermediate 8, and 10-(2-naphthyl)anthracene-9-boric acid was replaced with an equal amount of deuterated 10-(2-naphthyl)anthracene-9-boric acid to prepare compound 119.

[0262] Compound 119 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 119 was 664 (M+).

[0263] Embodiment 14

[0264] This example provides compound 123 and its synthesis method, the synthesis method is as follows:

[0265]

[0266] Referring to the synthesis method of compound 99, intermediate 4 was replaced with an equal amount of intermediate 9, and 10-(2-naphthyl)anthracene-9-boric acid was replaced with an equal amount of deuterated 10-(2-naphthyl)anthracene-9-boric acid to prepare compound 123.

[0267] Compound 123 was characterized by fast atom bombardment mass spectrometry, and the MS (FAB) of test compound 123 was 612 (M+).

[0268] The following device examples and device comparative examples also use compounds with the following structures:

[0269]

[0270] Device Example 1

[0271] This device embodiment provides an organic electroluminescent device, using the compound 1 provided in Example 1 of the present invention as a main material of the light-emitting layer.

[0272] The structure of the organic electroluminescent device is: ITO / HT (40 nm) / luminescent layer main material: BD 3% (30 nm) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0273] The preparation method of the organic electroluminescent device is as follows:

[0274] (1) A transparent electrode indium tin oxide (ITO) film (15 Ω / sq) (Samsung Corning, South Korea) on a glass substrate for preparing an organic light emitting diode (OLED) device was ultrasonically cleaned with trichloroethylene, acetone, ethanol and distilled water in sequence, and then stored in isopropyl alcohol. Subsequently, the ITO substrate was mounted on a substrate fixture of a vacuum vapor deposition device;

[0275] (2) HT was introduced into the chamber of the vacuum vapor deposition apparatus, and the chamber pressure of the apparatus was then controlled to reach 10 -6 Support, deposit 40nm HT as a hole transport layer on the ITO substrate;

[0276] (3) transferring to another chamber, introducing the compound 1 provided by the present invention into one chamber of the vacuum vapor deposition equipment as a matrix material, and introducing the compound BD into another chamber as a dopant, evaporating the two materials at different rates, and depositing them at a doping amount of 3 wt % (based on the total weight of the matrix material and the dopant), thereby forming a light-emitting layer with a thickness of 30 nm on the hole transport layer;

[0277] (4) vacuum evaporating 30 nm of TPBI on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device;

[0278] (5) On the electron transport layer, 0.5 nm of LiF and 150 nm of Al were vacuum-deposited in sequence as an electron injection layer and a cathode, respectively, to obtain an organic electroluminescent device.

[0279] Device Examples 2-23

[0280] Device Examples 2-23 respectively provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer is different (see Table 1 for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0281] Device Comparison Example 1

[0282] The device comparative example 1 provides an organic electroluminescent device, which is different from the device example 1 only in that the main material of the light-emitting layer is different (see Table 1 for details), and the other preparation steps and conditions are the same as those of the device example 1.

[0283] Performance Testing

[0284] Test method: The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used to test the driving voltage, current efficiency and life LT90 of the OLED devices provided above; LT90 refers to the time required for the brightness to drop to 90% of the original brightness while maintaining the current density at the initial brightness of 1000nit. The test items include the brightness, driving voltage and current efficiency of the organic electroluminescent device. The driving voltage, current efficiency and LT90 data are all based on a brightness of 1000cd / m 2 The relative value of .

[0285] The performance test results are shown in Table 1 below:

[0286] Table 1

[0287] serial number Light-emitting layer host material <![CDATA[Required brightness (1000 cd / m 2 )]]> Driving voltage Current efficiency LT90 Device Example 1 Compound 1 1000 1.01 1.10 1.11 Device Example 2 Compound 4 1000 0.99 1.19 1.27 Device Example 3 Compound 5 1000 1.01 1.11 1.13 Device Example 4 Compound 10 1000 1.01 1.21 1.41 Device Example 5 Compound 13 1000 1.01 1.21 1.43 Device Example 6 Compound 20 1000 1.01 1.21 1.23 Device Example 7 Compound 21 1000 1.01 1.17 1.08 Device Example 8 Compound 26 1000 1.00 1.22 1.38 Device Example 9 Compound 29 1000 1.00 1.23 1.39 Device Example 10 Compound 36 1000 0.99 1.21 1.31 Device Example 11 Compound 37 1000 1.00 1.23 1.25 Device Example 12 Compound 42 1000 0.99 1.26 1.55 Device Example 13 Compound 46 1000 0.99 1.26 1.57 Device Example 14 Compound 65 1000 1.01 1.15 1.05 Device Example 15 Compound 81 1000 1.00 1.21 1.22 Device Example 16 Compound 98 1000 1.01 1.47 1.35 Device Example 17 Compound 99 1000 1.02 1.47 1.31 Device Example 18 Compound 106 1000 0.98 1.51 1.85 Device Example 19 Compound 107 1000 1.00 1.49 1.81 Device Example 20 Compound 118 1000 0.98 1.53 1.90 Device Example 21 Compound 119 1000 1.00 1.50 1.83 Device Example 22 Compound 122 1000 0.88 1.13 1.83 Device Example 23 Compound 123 1000 0.90 1.10 1.73 Device Comparison Example 1 BH-Ref 1000 1 1 1

[0288] From the above content, it can be seen that in the present invention, by designing the structure of anthracene organic compounds, anthracene organic compounds that can be used as the main material of the light-emitting layer are obtained. Using this anthracene organic compound as the main material of the light-emitting layer, an organic electroluminescent device with lower driving voltage, higher luminous effect and longer service life is prepared.

[0289] From the comparison of the relevant data of device embodiments 1-23 and device comparative example 1, it can be seen that in the present invention, by designing the structure of the anthracene organic compound and further by specially selecting the Ar1 group in the anthracene organic compound (compound of formula I), an anthracene organic compound suitable for use as the main material of the light-emitting layer of an organic electroluminescent device is obtained. Using this compound as the main material of the light-emitting layer further improves the current efficiency and service life of the organic electroluminescent device.

[0290] From the comparison of the relevant data of device examples 18-23 and device examples 1-17, it can be seen that the present invention further selects anthracene compounds in which all the hydrogen atoms on the Ar1 group in the compound of formula I are deuterated and all the hydrogen atoms on R2 are deuterated (i.e., meeting conditions (2) and conditions (3)) as the main material of the light-emitting layer, which can further improve the current efficiency and service life of the organic electroluminescent device, and due to the presence of deuterium atoms on specific groups, the energy level of the compound is reduced, thereby reducing the driving voltage of the organic electroluminescent device.

[0291] The applicant declares that the present invention illustrates the organic compounds and applications of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An anthracene organic compound, characterized in that: The anthracene organic compound has a structure shown in the following formula I: Wherein, Ar1 is selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene group, a benzofuranyl group or a benzothiophenyl group; Ar2 is selected from a single bond or a substituted or unsubstituted C6-C20 arylene group; R1-R4 are each independently selected from any one of a hydrogen atom, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C6-C30 heteroaryl group; The substituents in Ar1, Ar2, R1-R4 are each independently selected from any one of -F, -CN, a deuterium atom, a C1-C10 alkyl group or a C6-C20 aryl group.

2. The anthracene organic compound according to claim 1, characterized in that: The compound of formula I meets at least one of the following conditions: (1) The compound of formula I does not contain deuterium atoms; (2) In the compound of formula I, all hydrogen atoms on R1 and R2 are replaced by deuterium atoms; (3) In the compound of formula I, Ar1 is not a single bond, and all hydrogen atoms on Ar1 are replaced by deuterium atoms; (4) In the compound of formula I, all hydrogen atoms on the anthracene ring are replaced by deuterium atoms; (5) In the compound of formula I, Ar2 is not a single bond, and all hydrogen atoms on Ar2 are replaced by deuterium atoms; (6) In the compound of formula I, all hydrogen atoms on R3 and R3 are replaced by deuterium atoms; Preferably, the compound of formula I meets conditions (2) and (3).

3. The anthracene organic compound according to claim 1 or 2, characterized in that: The C6-C20 arylene group is selected from any one of phenylene, naphthylene, biphenylene or terphenylene; Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl or terphenyl; Preferably, the C6-C30 heteroaryl group is selected from any one of benzofuranyl, benzothiophenyl, naphthobenzofuranyl, dibenzofuranyl and dibenzothiophenyl; Preferably, the C1-C10 alkyl group is selected from any one of methyl, ethyl, propyl, butyl and cyclohexyl.

4. The anthracene organic compound according to any one of claims 1 to 3, characterized in that: Ar1 is selected from any one of a single bond, a phenylene group, a benzofuranyl group or a benzothiophenylene group; Preferably, said R1 is selected from a hydrogen atom; Preferably, R2 is selected from any one of naphthobenzofuranyl, benzofuranyl, dibenzofuranyl and dibenzothiophenyl; Preferably, Ar2 is selected from a single bond or a phenylene group; Preferably, said R3 is selected from a hydrogen atom; Preferably, said R2 is selected from naphthyl.

5. The anthracene organic compound according to any one of claims 1 to 4, characterized in that: The compounds of formula I include the following substituted or unsubstituted compounds: Wherein, X1-X7 are each independently selected from O or S; The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

6. The anthracene organic compound according to any one of claims 1 to 5, characterized in that: The compounds of formula I include the following substituted or unsubstituted compounds: Wherein, X1-X7 are each independently selected from O or S; The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

7. The anthracene organic compound according to any one of claims 1 to 6, characterized in that: The compound of formula I is selected from any one of compounds 1-178:

8. An intermediate, characterized in that The intermediates include the following substituted or unsubstituted compounds: Wherein, Y1, Y4, Y5, and Y6 each independently represent a halogen atom; Y2 and Y3 are each independently selected from any one of a hydrogen atom, a halogen atom, or -B(OH)2; The substitution means that the hydrogen atoms in the above compounds can each independently be replaced by a deuterium atom; The intermediate is used to prepare the anthracene organic compound according to any one of claims 1 to 7; Preferably, Y1, Y4, Y5 and Y6 each independently represent Br or I.

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode; The material of the organic thin film layer includes at least one anthracene organic compound as claimed in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic thin film layer comprises a light-emitting layer, and the light-emitting layer comprises at least one anthracene organic compound according to any one of claims 1 to 7; Preferably, the organic thin film layer further includes at least one of a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

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