An anthracene ketone compound, a preparation method and application thereof, and an organic electroluminescent device

Abstract

The application provides an anthracene ketone compound and a preparation method and application thereof, and an organic electroluminescent device, and belongs to the technical field of semiconductors. When the anthracene ketone compound provided by the application is used as one of double hosts of a light-emitting layer, the balance of holes and electrons is good, the voltage of the device can be effectively reduced, the current efficiency of the device is improved, and the service life of the device is prolonged. The results of examples show that when the anthracene ketone compound provided by the application is used as a light-emitting layer material, the current efficiency of the obtained organic electroluminescent device is 144.7-158.1, and the service life is 351.6-373.9 h.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of semiconductor, in particular to an anthracene ketone compound, a preparation method and application thereof, and an organic electroluminescent device. BACKGROUND

[0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and new lighting products, and is expected to replace existing liquid crystal display and fluorescent lamp lighting, and has a very wide application prospect.

[0003] The OLED light-emitting device has a sandwich structure, including electrode material film layers and organic light-emitting functional layers sandwiched between different electrode film layers, various materials with different functions are stacked together according to the purpose to jointly constitute the OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, positive and negative charges in the organic light-emitting functional layer will be further recombined in the light-emitting layer, that is, OLED electroluminescence will be generated.

[0004] Although OLED display technology has been widely used in smart phones, tablet computers and other fields, and will further expand to large-size applications such as televisions, the performance of OLED devices such as luminous efficiency and service life still needs to be further improved compared with the actual product application requirements.

[0005] At present, the researches on improving the performance of OLED light-emitting devices mainly include: reducing the driving voltage of the device, improving the current efficiency of the device, prolonging the service life of the device, etc. In order to continuously improve the performance of OLED devices, not only the OLED device structure and manufacturing process need to be improved, but also new OLED functional materials with higher performance need to be developed. SUMMARY

[0006] Therefore, the present application aims to provide an anthracene ketone compound, a preparation method and application thereof, and an organic electroluminescent device. The anthracene ketone compound provided by the present application can effectively improve the current efficiency and service life of the OLED device.

[0007] In order to achieve the above-mentioned application purposes, the present application provides the following technical solutions:

[0008] The present application provides an anthracene ketone compound having the structure shown in formula (1):

[0009]

[0010] In formula (1), X is O or S;

[0011] Ar1, Ar2are each independently a single bond, a substituted or unsubstituted C6-C 30 arylene, a substituted or unsubstituted C2-C 30 heteroarylene;

[0012] B is a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C

[0013] C has a structure represented by formula (2);

[0014]

[0015] In formula (2), D has a structure represented by formula (3):

[0016]

[0017] In formula (3), X2is -O-, -S- or -N(R)-;

[0018] R in said -N(R)- is one or more of a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl;

[0019] In the above substituted groups, the substituents are each independently one or more of halogen, cyano, C1-C 10 alkyl, C6-C 30 aryl, C2-C 30 heteroaryl;

[0020] The heteroatoms in said heteroaryl and heteroarylene are selected from one or more of an oxygen atom, a sulfur atom or a nitrogen atom.

[0021] Preferably, has a structure represented by any one of formula (1-1) to formula (1-2):

[0022]

[0023]

[0024] Preferably, has a structure represented by any one of formula (1-3) to formula (1-4):

[0025]

[0026] Preferably, has a structure represented by any one of formula (1-5) to formula (1-10):

[0027]

[0028]

[0029] Preferably, Ar1, Ar2 are each independently one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted carbazolyiene, substituted or unsubstituted furanylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted N-phenylcarbazolyiene, substituted or unsubstituted quinolyiene, substituted or unsubstituted isoquinolyiene, substituted or unsubstituted naphtholyiene.

[0030] B is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted N-phenylcarbazolyl, or a structure represented by formula (2);

[0031] R is one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furanyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphtholyene, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazolyl;

[0032] In the above substituted groups, the substituents are each independently one or more of fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group, benzofuranyl group, carbazolyl group, diphenylamine group, benzothienyl group, or furanyl group.

[0033] The present application provides a preparation method of the above anthracene ketone compound, comprising the following steps:

[0034] The compound having the structure represented by formula a is subjected to a first substitution reaction with the compound having the structure represented by formula b to obtain an intermediate having the structure represented by formula c;

[0035]

[0036] The intermediate with the structure shown in formula c is subjected to a second substitution reaction with a compound with the structure shown in formula d to obtain an anthracene ketone compound with the structure shown in formula 1.

[0037]

[0038] The anthracene ketone compound is used for preparing an organic electroluminescent device.

[0039] The anthracene ketone compound is used for preparing an organic electroluminescent device.

[0040] Preferably, the organic functional layer comprises a light-emitting layer, and the anthracene ketone compound is used in the light-emitting layer.

[0041] Preferably, the light-emitting layer comprises a host material and a dopant material, and the host material comprises the anthracene ketone compound.

[0042] The anthracene ketone compound has the structure shown in formula (1).

[0043] The anthracene ketone compound has the structure shown in formula (1).

[0044] The anthracene ketone compound has the structure shown in formula (1). BRIEF DESCRIPTION OF DRAWINGS

[0045] Figure 1 FIG. 1 is a schematic diagram of a cross-sectional structure of an organic electroluminescent device according to the present application. DETAILED DESCRIPTION

[0046] The anthracene ketone compound has the structure shown in formula (1).

[0047]

[0048] In formula (1), X is O or S.

[0049] Ar1 and Ar2 are each independently single-bonded, substituted, or unsubstituted C6-C bonds. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0050] B represents substituted or unsubstituted C6-C. 30 Aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted N-phenylcarbazoyl or one of the structures shown in formula (2);

[0051] C has the structure shown in equation (2);

[0052]

[0053] In equation (2), D has the structure shown in equation (3):

[0054]

[0055] In equation (3), X2 is -O-, -S-, or -N(R)-;

[0056] In the -N(R)-, R represents substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl groups;

[0057] Among the substituted groups mentioned above, each substituent is independently a halogen, cyano, or C1-C group. 10 Alkyl, C6-C 30 Aryl, C2-C 30 One or more of the heteroaryl groups;

[0058] The heteroatoms in the heteroaryl and heteroaryl groups are selected from one or more of oxygen, sulfur, or nitrogen atoms.

[0059] In this invention, Ar1 and Ar2 are each preferably, independently, one of the following: substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted diphenylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted furanylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted N-phenylcarbazolylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinylene, and substituted or unsubstituted naphthidylene.

[0060] In the present application, B is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted N-phenylcarbazolyl group, or a structure represented by formula (2).

[0061] In the present application, R is preferably one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted naphthrydinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted benzimidazolyl group.

[0062] In the present application, in the above substituted groups, the substituents are each independently one or more of a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, a benzofuranyl group, a carbazolyl group, a diphenylamino group, a benzothienyl group, or a furanyl group.

[0063] In the present application, the anthracene ketone compound preferably has a structure represented by any one of formulae (1-1) to (1-2):

[0064]

[0065] In the present application, the anthracene ketone compound preferably has a structure represented by any one of formulae (1-3) to (1-4):

[0066]

[0067] In the present application, the anthracene ketone compound preferably has a structure represented by any one of formulae (1-5) to (1-10):

[0068]

[0069]

[0070] In the present application, the anthracene ketone compound preferably has a structure represented by any one of formulae 1 to 117:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] The present application provides a preparation method of the anthracene ketone compound, comprising the following steps:

[0077] The compound with the structure shown in formula a is subjected to a first substitution reaction with the compound with the structure shown in formula b to obtain an intermediate with the structure shown in formula c.

[0078]

[0079] The intermediate with the structure shown in formula c is subjected to a second substitution reaction with the compound with the structure shown in formula d to obtain the anthracene ketone compound with the structure shown in formula 1.

[0080]

[0081] In the present application, the compound with the structure shown in formula a is subjected to a first substitution reaction with the compound with the structure shown in formula b to obtain an intermediate with the structure shown in formula c. In the present application, the molar ratio of the compound with the structure shown in formula a to the compound with the structure shown in formula b is preferably 1-1.2:1.

[0082] In the present application, the first substitution reaction is preferably carried out in the presence of a catalyst, and the catalyst is preferably Pd2(dba)3 and P(t-Bu)3, and the molar ratio of Pd2(dba)3 to P(t-Bu)3 is preferably 1:1.

[0083] In the present application, the first substitution reaction is preferably carried out in the presence of sodium tert-butoxide, and the molar ratio of the compound with the structure shown in formula b to sodium tert-butoxide is preferably 1:3.

[0084] In the present application, the solvent used in the first substitution reaction is preferably toluene. In the present application, the temperature of the first substitution reaction is preferably refluxing temperature, and the time is preferably 24h.

[0085] After the first substitution reaction, the present application preferably carries out post-treatment on the obtained first substitution reaction product, and the post-treatment preferably comprises the following steps:

[0086] The first substitution reaction solution is filtered, the filtrate is rotary evaporated to remove the solvent, and the crude product is passed through a silica gel column to obtain the intermediate product with the structure shown in formula c.

[0087] In the present application, the intermediate product with the structure shown in formula c is subjected to a second substitution reaction with a compound with the structure shown in formula d to obtain an anthracene ketone compound with the structure shown in formula 1. In the present application, the molar ratio of the intermediate product with the structure shown in formula c to the compound with the structure shown in formula d is preferably 1:1.

[0088] In the present application, the second substitution reaction is preferably carried out in the presence of a catalyst, and the catalyst is preferably Pd(PPh3)4.

[0089] In the present application, the second substitution reaction is preferably carried out in the presence of potassium carbonate.

[0090] In the present application, the solvent used in the second substitution reaction is preferably toluene and ethanol, and the volume ratio of toluene to ethanol is preferably 3:1.

[0091] In the present application, the temperature of the second substitution reaction is preferably 100°C, and the time is preferably 18h.

[0092] After the second substitution reaction, the present application preferably performs post-treatment on the obtained second reaction product, and the post-treatment preferably includes the following steps:

[0093] The second substitution reaction solution is filtered, the filtrate is rotary evaporated to remove the solvent, and the crude product is passed through a silica gel column to obtain the intermediate product with the structure shown in formula c.

[0094] The present application provides the use of the above-mentioned anthracene ketone compound in the preparation of an organic electroluminescent device. In the present application, the use is preferably as a light-emitting layer.

[0095] The present application provides an organic electroluminescent device, comprising a cathode, an anode, and an organic functional layer, the organic functional layer being located between the anode and the cathode, and the organic functional layer comprising the above-mentioned anthracene ketone compound.

[0096] In the present application, the organic functional layer preferably comprises a light-emitting layer, and the light-emitting layer comprises the above-mentioned anthracene ketone compound. In the present application, the organic functional layer preferably comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and an electron injection layer, which are sequentially stacked, and the hole injection layer is in contact with the anode, and the electron injection layer is in contact with the cathode.

[0097] In the present application, the surface of the cathode layer is preferably provided with a light extraction layer.

[0098] The material of the anode, the hole injection layer, the hole transport layer, the electron blocking layer, the electron transport layer, the electron injection layer and the cathode is not specially required in the present application, and the material well known in the art can be used.

[0099] In the present application, the light-emitting layer preferably comprises a host material and a dopant material, and the host material comprises the anthrone compound as described above.

[0100] In the present application, the mass percentage of the host material in the light-emitting layer is preferably 80-95%, more preferably 85-90%, and the mass percentage of the dopant material in the light-emitting layer is preferably 5-20%, preferably 10-15%. The present application does not have special requirements for the specific type of the dopant material, and the conventional guest light-emitting material in the art can be used.

[0101] As a specific embodiment of the present application, the cross-sectional structure of the organic electroluminescent device is shown in Figure 1 . Figure 1 In the present application, 1-Substrate layer, 2-Anode layer, 3-Hole injection layer, 4-Hole transport layer, 5-Electron blocking layer, 6-Light-emitting layer, 7-Electron transport layer, 8-Electron injection layer, 9-Cathode layer, 10-Light extraction layer.

[0102] Each layer of the organic layer in the organic electroluminescent device provided by the present application is preferably prepared by vacuum evaporation method, molecular beam evaporation method, solvent-dissolved dip coating method, spin coating method, rod coating method or inkjet printing method. The metal electrode is preferably prepared by evaporation method or sputtering method.

[0103] The anthrone compound, the preparation method and application thereof and the organic electroluminescent device provided by the present application will be described in detail in combination with the embodiments below, but they should not be understood as limiting the protection scope of the present application.

[0104] All the reactants in the following embodiments are purchased from Yantai Wannun Fine Chemical Co., Ltd.

[0105] Synthesis of compound 1 in Example 1

[0106] Synthesis of intermediate A-1

[0107]

[0108] In a 250ml three-necked flask, 0.01mol of raw material B-1, 0.012mol of raw material D-1 and 150ml of toluene were stirred and mixed under nitrogen protection, and then 5×10 -5 mol of Pd2(dba)3, 5×10 -5mol P(t-Bu)3, 0.03 mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampled point board, the reaction was complete; natural cooling to room temperature, filtration, the filtrate was evaporated to no fraction, over neutral silica gel column, to obtain the target product intermediate A-1.

[0109] Elemental analysis structure (molecular formula C 34 H 22 ClNO2S): Theoretical value C, 75.06; H, 4.08; Cl, 6.52; N, 2.57; S, 5.89; Test value: C, 75.13; H, 4.06; Br, 6.62; N, 2.48; S, 5.83. LC-MS (m / z) (M + ): Theoretical value is 543.11, the measured value is 543.09.

[0110] The synthesis of intermediate A required in the following examples is referred to the synthesis of intermediate A-1, and the synthesis raw materials are shown in Table 1:

[0111] Table 1 structure of intermediate A

[0112]

[0113]

[0114] Synthesis of compound 1

[0115]

[0116] Dissolve 20 mmol of intermediate A-1 and 20 mmol of raw material C-1 in a mixture of 30 mL of toluene and 10 mL of ethanol, after oxygen removal, add 0.1 mmol of Pd (PPh3) 4 and 3 mol / L of K2CO3 aqueous solution 15 mL, react at 100°C under inert atmosphere for 18 hours; after the raw material is completely reacted, cool, filter, evaporate the solvent from the filtrate, and pass the crude product through a silica gel column to obtain the target product compound 1.

[0117] Elemental analysis structure (molecular formula C 52 H 33 NO3S): Theoretical value: C, 83.07; H, 4.42; N, 1.86; S, 4.26; Test value C, 83.05; H, 4.47; N, 1.84; S, 4.25. LC-MS: The material molecular weight is 751.22, and the measured molecular weight is 751.25.

[0118] 1H NMR (400 MHz, Chloroform-d) δ 8.01 (m, 2H), 7.98 (d, 1H), 7.88 (d, 1H), 7.88-7.84 (m, 1H), 7.75 (d, 1H), 7.61 (s, 5H), 7.59-7.43 (m, 8H), 7.38 (m, 2H), 7.25-7.12 (m, 3H), 7.11-6.97 (m, 3H), 1.56 (s, 6H).

[0119] Synthesis of compound 2 of example 2

[0120]

[0121] Prepared according to the procedure for the synthesis of compound 1 of example 1, except that starting material C-2 was used in place of starting material C-1; elemental analysis structure (molecular formula C 52 H 33 NO3S): theory: C, 83.07; H, 4.42; N, 1.86; S, 4.26; found C, 83.05; H, 4.46; N, 1.85; S, 4.31. LC-MS: material molecular weight 751.22, found molecular weight 751.26.

[0122] 1 H NMR (400 MHz, Chloroform-d) δ 8.01 (m, 2H), 7.98 (d, 1H), 7.88 (d, 1H), 7.88-7.84 (m, 1H), 7.75 (d, 1H), 7.61 (s, 5H), 7.59-7.43 (m, 8H), 7.38 (m, 2H), 7.25-7.12 (m, 3H), 7.11-6.97 (m, 3H), 1.56 (s, 6H).

[0123] Synthesis of compound 29 of example 3

[0124]

[0125] Prepared according to the procedure for the synthesis of compound 1 of example 1, except that intermediate A-2 was used in place of intermediate A-1; starting material C-2 was used in place of starting material C-1; elemental analysis structure (molecular formula C48H31NO3): theory: C, 86.08; H, 4.67; N, 2.09; found C, 86.02; H, 4.66; N, 2.05. LC-MS: material molecular weight 669.23, found molecular weight 669.27.

[0126] 1H NMR (400 MHz, Chloroform-d) δ 9.22-9.03 (m, 1H), 8.39 (p, 1H), 8.03 (ddt, 3H), 7.99-7.84 (m, 2H), 7.84-7.71 (m, 2H), 7.66 (dd, 1H), 7.61-

[0127] 7.43 (m, 6H), 7.41-7.30 (m, 2H), 7.28-7.12 (m, 4H), 7.10-6.96 (m, 3H), 1.56 (s, 6H).

[0128] Synthesis of compound 30 of Example 4

[0129]

[0130] Prepared according to the procedure for the synthesis of compound 1 of Example 1 with the exception that intermediate A-2 was used in place of intermediate A-1 ; starting material C-3 was used in place of starting material C-1 ; elemental analysis structure (molecular formula C 48 H 31 NO3): Theory: C, 86.08; H, 4.67; N, 2.09; Found C, 86.06; H, 4.71; N, 2.05. LC-MS: Material molecular weight 669.23, found molecular weight 669.24.

[0131] 1 H NMR (400 MHz, Chloroform-d) δ 9.22-9.03 (m, 1H), 8.39 (p, 1H), 8.03 (ddt, 3H), 7.99-7.84 (m, 2H), 7.84-7.71 (m, 2H), 7.66 (dd, 1H), 7.61-

[0132] Synthesis of compound 116 of Example 5

[0133]

[0134] Prepared according to the procedure for the synthesis of compound 1 of Example 1 with the exception that intermediate A-3 was used in place of intermediate A-1 ; starting material C-4 was used in place of starting material C-1 ; elemental analysis structure (molecular formula C 46 H 31NO2S): Calc. C, 83.85; H, 5.03; N, 2.00; S, 4.57; Found C, 83.88; H, 5.02; N, 2.04; S, 4.53. LC-MS: Material mass 701.24, found mass 701.27.

[0135] 1 H NMR (400 MHz, Chloroform-d) δ 8.11 (dd, 1H), 7.95 (d, 1H), 7.83-

[0136] 7.64 (m, 4H), 7.59-7.49 (m, 2H), 7.46-7.27 (m, 10H), 7.25-7.09 (m, 4H), 7.03 (m, 1H), 1.56 (d, 12H).

[0137] Synthesis of compound 117 of example 6

[0138]

[0139] Prepared according to the procedure for the synthesis of compound 1 of example 1, except that intermediate A-4 was used in place of intermediate A-1; starting material C-6 was used in place of starting material C-1; elemental analysis structure (molecular formula C 49 H 35 NO2S): Calc. C, 83.85; H, 5.03; N, 2.00; S, 4.57; Found C, 83.88; H, 5.02; N, 2.04; S, 4.53. LC-MS: Material mass 701.24, found mass 701.27.

[0140] 1 H NMR (400 MHz, Chloroform-d) δ 8.11 (dd, 1H), 7.95 (d, 1H), 7.83-

[0141] 7.64 (m, 4H), 7.59-7.49 (m, 2H), 7.46-7.27 (m, 10H), 7.25-7.09 (m, 4H), 7.03 (m, 1H), 1.56 (d, 12H).

[0142] Synthesis of compound 79 of example 7

[0143]

[0144] Prepared according to the procedure for the synthesis of compound 1 of example 1, except that intermediate A-4 was used in place of intermediate A-1; starting material C-6 was used in place of starting material C-1; elemental analysis structure (molecular formula C49 H 35 NO2S) : Theoretical: C, 83.85; H, 5.03; N, 2.00; S, 4.57; Found: C, 83.82; H, 5.02; N, 2.03; S, 4.56. LC-MS: Material molecular weight 701.24, found 701.23.

[0145] 1 H NMR (400 MHz, Chloroform-d) δ 8.34 (dd, 1H), 8.06 (d, 1H), 7.87 (d, 1H), 7.83-7.75 (m, 2H), 7.72 (d, 1H), 7.64 (dd, 1H), 7.61-7.52 (m, 2H), 7.50-7.37 (m, 5H), 7.34 (m, 2H), 7.27-7.13 (m, 4H), 7.10 (dd, 1H), 7.07-6.98 (m, 2H), 1.56 (d, 12H).

[0146] Synthesis of compound 80 of example 8

[0147]

[0148] Prepared according to the procedure for the synthesis of compound 1 of example 1, except that intermediate A-4 was used instead of intermediate A-1; starting material C-7 was used instead of starting material C-1; elemental analysis structure (molecular formula C 40 H 27 NO2S) : Theoretical: C, 82.03; H, 4.65; N, 2.39; S, 5.47; Found: C, 82.01; H, 4.62; N, 2.37; S, 5.46. LC-MS: Material molecular weight 585.18, found 585.13.

[0149] 1 H NMR (400 MHz, Chloroform-d) δ 8.34 (dd, 1H), 8.06 (d, 1H), 7.87 (d, 1H), 7.83-7.75 (m, 2H), 7.72 (d, 1H), 7.64 (dd, 1H), 7.61-7.52 (m, 2H), 7.50-7.37 (m, 5H), 7.34 (m, 2H), 7.27-7.13 (m, 4H), 7.10 (dd, 1H), 7.07-6.98 (m, 2H), 1.56 (d, 12H).

[0150] 7.73 (m, 2H), 7.70 (d, 1H), 7.64 (dd, 1H), 7.61-7.55 (m, 2H), 7.51-7.30 (m, 6H), 7.29-6.99 (m, 7H), 1.55 (s, 6H).

[0151] Synthesis of compound 91 of example 9

[0152]

[0153] Prepared according to the procedure for the synthesis of compound 1 in example 1, except that intermediate A-5 was used instead of intermediate A-1; and starting material C-8 was used instead of starting material C-1; elemental analysis structure (molecular formula C 51 H 33 N3O3) : Theoretical value: C, 83.25; H, 4.52; N, 5.71; Test value C, 83.27; H, 4.53; N, 5.69. LC-MS: Material molecular weight is 735.25, the measured molecular weight 735.28.

[0154] 1 H NMR (400 MHz, Chloroform-d) δ 8.56 (d, 1H), 8.32 (d, 1H), 8.00 (dd, 1H), 7.92-7.84 (m, 2H), 7.82 (d, 1H), 7.65-7.43 (m, 9H), 7.43-7.25 (m, 7H), 7.25-7.17 (m, 2H), 7.13 (d, 1H), 7.05 (m, 2H), 1.61 (s, 6H).

[0155] Synthesis of compound 104 of example 10

[0156]

[0157] In a 250 ml three-necked flask, under nitrogen protection, 0.01 mol of starting material B-4, 0.024 mol of starting material D-1, 250 ml of toluene were stirred and mixed, then 8 x 10 -5 mol of Pd2(dba)3, 8 x 10 -5 mol of P(t-Bu)3, 0.05 mol of sodium tert-butoxide were added, heated to 130°C, refluxed for 32 hours, sampled point board, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column to obtain the target product, elemental analysis structure (molecular formula C 55 H 38 N2O4): Theoretical value: C, 83.52; H, 4.84; N, 3.54; Test value C, 83.54; H, 4.81; N, 3.52. LC-MS: Material molecular weight is 790.28, the measured molecular weight 790.24.

[0158] 1 H NMR (400 MHz, Chloroform-d) δ 8.56 (d, 1H), 8.32 (d, 1H), 8.00 (dd, 1H), 7.92-7.84 (m, 2H), 7.82 (d, 1H), 7.65-7.43 (m, 9H), 7.43-7.25 (m, 7H), 7.25-7.17 (m, 2H), 7.13 (d, 1H), 7.05 (m, 2H), 1.61 (s, 6H).

[0159] The application effects of the OLED materials synthesized in the application in devices are described in detail by applying examples 1-10 and application comparative examples 1-4. The manufacturing processes of the devices described in application examples 1-10, application comparative examples 2-4 and application comparative example 1 are completely the same, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent, the difference is that the main body material of the light-emitting layer is replaced, the device structure obtained in each application example is shown in Table 2, and the performance test results of the device are shown in Table 3.

[0160] Application Comparative Example 1

[0161] a) The substrate layer 1 is transparent glass, and the anode layer 2 (Ag, thickness of 100 nm) is evaporated on the surface of the substrate layer 1 by vacuum evaporation;

[0162] b) HAT-CN is evaporated on the anode layer 2 as a hole injection layer 3 by vacuum evaporation, with a thickness of 10 nm;

[0163] c) HT-1 is evaporated on the hole injection layer 3 as a hole transport layer 4 by vacuum evaporation, with a thickness of 140 nm;

[0164] d) EB-1 is evaporated on the hole transport layer 4 as an electron blocking layer 5 by vacuum evaporation, with a thickness of 30 nm,

[0165] e) The light-emitting layer 6 is evaporated on the electron blocking layer 5, with Ref-1 and GH-2 as the main body material and GD-1 as the doping material, the mass ratio of Ref-1, GH-1 and GD-1 is 45:45:10, and the thickness is 40 nm;

[0166] f) ET-1 and Liq with a mass ratio of 1:1 are evaporated on the light-emitting layer 6 as an electron transport layer 7 by vacuum evaporation, with a thickness of 40 nm;

[0167] g) LiF is vacuum evaporated on the electron transport layer 7 as an electron injection layer 8, with a thickness of 1 nm;

[0168] h) A layer of Mg:Ag with a mass ratio of 1:9 is vacuum evaporated on the electron injection layer 8 as a cathode layer 9, with a thickness of 15 nm;

[0169] i) CP-1 is evaporated on the cathode layer 9 as a light extraction layer 10 by vacuum evaporation, with a thickness of 70 nm.

[0170] After the electroluminescent device is completed according to the above steps, the current efficiency of the device is measured, and the results are shown in Table 4. The molecular structure formula of the related material is as follows:

[0171]

[0172]

[0173] Table 2: Device structures of each application example

[0174]

[0175]

[0176]

[0177] The test data of the obtained electroluminescent devices are shown in Table 3.

[0178] Table 3: Test data of the obtained electroluminescent devices

[0179]

[0180]

[0181] Note: Current efficiency and lifetime were tested using IVL (current-voltage-luminance) test system, the current density during testing was 10 mA / cm 2 .

[0182] As can be seen from the results in Table 3, the organic compound of the present application as one of the dual hosts of the light-emitting layer has significantly improved device efficiency and device lifetime compared with Comparative Examples 1-4.

[0183] The above only describes the preferred embodiments of the present application, and it should be noted that for those skilled in the art, several improvements and refinements can be made without departing from the principles of the present application, and these improvements and refinements should also be considered within the protection scope of the present application.

Claims

1. An anthrone compound having the structure shown in Formula 30, Formula 91, Formula 104 or Formula 116: Formula 30; Equation 91; Equation 104; Equation 116.

2. A method for preparing the anthrone compound according to claim 1, comprising the following steps: Raw material D-2 undergoes a substitution reaction with raw material B-2 to obtain intermediate A-2; Raw material D-2; Raw material B-2; Intermediate A-2; Raw material D-3 undergoes a substitution reaction with raw material B-2 to obtain intermediate A-3; Raw material D-3; Raw material B-2; Intermediate A-3; Raw material D-5 undergoes a substitution reaction with raw material B-3 to obtain intermediate A-5; Raw material D-5; Raw material B-3; Intermediate A-5; Intermediate A-2 undergoes a substitution reaction with starting material C-3 to yield anthrone compounds having the structure shown in Formula 30: ； Intermediate A-5 undergoes a substitution reaction with starting material C-8 to yield anthrone compounds having the structure shown in Formula 91: ； Feedstock B-4 undergoes a substitution reaction with feedstock D-1 to yield anthrone compounds having the structure shown in Formula 104: ； Intermediate A-3 undergoes a substitution reaction with starting material C-4 to yield anthrone compounds having the structure shown in Formula 116. 。 3. The application of the anthrone compound of claim 1 or the anthrone compound prepared by the preparation method of claim 2 in the preparation of organic electroluminescent devices.

4. An organic electroluminescent device, comprising a cathode, an anode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode, characterized in that, The organic functional layer comprises anthrone compounds as described in any one of claims 1 or anthrone compounds prepared by the preparation method described in claim 2.

5. The organic electroluminescent device according to claim 4, characterized in that, The organic functional layer includes a light-emitting layer, which comprises an anthrone compound as described in any one of claims 1 or an anthrone compound prepared by the preparation method described in claim 2.

6. The organic electroluminescent device according to claim 5, characterized in that, The light-emitting layer comprises a host material and a dopant material, wherein the host material comprises anthrone compound as described in any one of claims 1 or anthrone compound prepared by the preparation method described in claim 2.

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