Boron-containing organic compound and application thereof

Abstract

The invention provides a boron-containing organic compound and application thereof. The boron-containing organic compound has a structure as shown in a formula 1, and as an organic electroluminescent blue light-emitting material, the boron-containing organic compound has lower driving voltage and higher current efficiency and service life at the same time. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a boron-containing organic compound and application thereof. Background Art

[0002] Organic electroluminescent display is known as the "third display technology revolution" because of its advantages such as self-luminescence, wide viewing angle, high contrast, fast response, low power consumption, lighter and thinner, power-saving, and flexible display. It is widely used in display and lighting fields such as mobile phones, televisions, computers, and cars.

[0003] With the development of organic electroluminescent materials, red and green light materials have basically met the needs of display. However, blue light materials are lagging behind red and green light in terms of efficiency and life due to their wide bandgap characteristics and difficulty in charge injection. However, the performance of blue light, especially deep blue light, has an important impact on improving display quality and reducing power consumption.

[0004] Blue luminescent materials with commercial prospects require high efficiency and long life. In 2016, Hatakeyama et al. designed a breakthrough TADF molecular design strategy based on the multiple resonance effect. Using triphenylborane as the skeleton, two nitrogen atoms were introduced at its para position to form a rigid framework compound MR-TADF material. This material exhibits a small ΔEST, high PLQY, a very small FWHM and extremely high color purity, and the device performance is greatly improved. However, the anti-intersystem crossing rate of the MR-TADF molecule itself is low, resulting in a serious efficiency roll-off of the device at actual brightness. The problems of fluorescence quenching, exciton annihilation and emission spectrum broadening caused by the aggregation effect limit the optimization and improvement of device performance. The research on MR-TADF materials based on boron nitrogen polycyclic aromatics faces great challenges. Therefore, the existing MR-TADF materials need to be further improved and developed. Summary of the invention

[0005] In view of the various defects and shortcomings in the prior art, the object of the present invention is to provide a boron-containing organic compound as an organic electroluminescent blue light-emitting material to improve the performance of organic electroluminescent devices.

[0006] In a first aspect of the present invention, there is provided a boron-containing organic compound having a structure shown in Formula 1 below:

[0007]

[0008] In Formula 1, the Q1 ring and the Q2 ring are independently an aryl ring or a heteroaryl ring, and at least one hydrogen in the Q1 ring and the Q2 ring may be substituted by deuterium, halogen, an alkyl group with or without a substituent R', a cycloalkyl group with or without a substituent R', a heteroalkyl group with or without a substituent R', a heterocycloalkyl group with or without a substituent R', an alkoxy group with or without a substituent R', an aryloxy group with or without a substituent R', an alkenyl group with or without a substituent R', an alkynyl group with or without a substituent R', an aryl group with or without a substituent R', a heteroaryl group with or without a substituent R', an alkylsilyl group with or without a substituent R', an amino group with 0 to 30 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, or a boron group with or without a substituent R';

[0009] A1, A2, A3, A4 each independently represent CR, N;

[0010] X is selected from O, S, Se, NR N , CRaRb or SiRaRb;

[0011] X1 and X2 are the same or different and are independently selected from O, S, Se, NR N , CRaRb or SiRaRb;

[0012] R, R N , Ra and Rb are the same or different at each occurrence, R, R N , Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms which may or may not contain a substituent R', an aryl group having 6 to 30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3 to 30 carbon atoms which may or may not contain a substituent R', a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0013] The Q1 ring, Q2 ring, R, R N, Ra and Rb are substituted with one or more substituents;

[0014] The Q1 ring, Q2 ring, R, R N , Ra and Rb are substituted with a substituent selected from deuterium, halogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms;

[0015] R, R N Any two adjacent groups in Ra and Rb may be connected to form a ring or not;

[0016] Q1 ring, Q2 ring, R, R N In , Ra, Rb, and R', at least one heteroatom of the heteroaryl ring, heteroalkyl, heteroaryl, and heterocycloalkyl is independently selected from N, O, S, Si, Se, P, B, and Ge.

[0017] According to some embodiments of the present invention, at least one hydrogen in the Q1 ring and the Q2 ring may be replaced by deuterium, halogen, an alkyl group having 1 to 30 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', a heteroalkyl group having 1 to 30 carbon atoms with or without a substituent R', a heterocycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', an alkoxy group having 1 to 30 carbon atoms with or without a substituent R', an aryloxy group having 6 to 30 carbon atoms with or without a substituent R', a 2-20 The invention can be substituted with an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms which may or may not contain a substituent R', an aryl group having 6 to 30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an alkylsilyl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an arylsilyl group having 6 to 30 carbon atoms which may or may not contain a substituent R', an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, or a boron group which may or may not contain a substituent R'.

[0018] According to some embodiments of the present invention, the Q1 ring and the Q2 ring are each independently an aryl ring having 6 to 12 carbon atoms or a heteroaryl ring having 2 to 6 carbon atoms.

[0019] According to some embodiments of the present invention, the Q1 ring and the Q2 ring are each independently a benzene ring.

[0020] According to some embodiments of the present invention, at least one hydrogen in the Q1 ring and the Q2 ring may be replaced by deuterium, halogen, an alkyl group having 1 to 30 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', a heteroalkyl group having 1 to 30 carbon atoms with or without a substituent R', a heterocycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', an alkoxy group having 1 to 30 carbon atoms with or without a substituent R', an aryloxy group having 6 to 30 carbon atoms with or without a substituent R', a 2-20 an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms which may or may not contain a substituent R', an aryl group having 6 to 30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an alkylsilyl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an arylsilyl group having 6 to 30 carbon atoms which may or may not contain a substituent R', an amino group having 0 to 30 carbon atoms which may or may not contain a substituent R', an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, a boronyl group;

[0021] The substituent R' substituted in the Q1 ring and the Q2 ring is one or more;

[0022] The substituent R' substituted in the Q1 ring and Q2 ring is selected from deuterium, halogen, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms.

[0023] According to some embodiments of the present invention, the compound has a structure represented by any one of the following formulae 1-1 to 1-16:

[0024]

[0025] In formulas 1-1 to 1-16, A1, A2, A3, A4, X, R, R N , Ra and Rb are defined in the same way as in Formula 1. A5, A6, A7, A8, A9, A 10 , A 11 Definitions are the same as A1, A2, A3, A4 in Formula 1;

[0026] X is selected from O, S, NR N or CRaRb;

[0027] In the compound, R, R N, Ra and Rb are the same or different and are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms which may or may not contain a substituent R', an aryl group having 6 to 30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an alkylsilyl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an arylsilyl group having 6 to 30 carbon atoms which may or may not contain a substituent R', an amino group having 0 to 30 carbon atoms which may or may not contain a substituent R', an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0028] R, R N , Ra and Rb are substituted with one or more substituents;

[0029] R, R N , Ra and Rb are substituted with a substituent selected from deuterium, halogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms;

[0030] R, R N Any two adjacent groups in Ra and Rb may be connected to form a ring or not;

[0031] R, R N In the heteroaryl ring, heteroalkyl, heteroaryl and heterocycloalkyl groups, at least one heteroatom is independently selected from N, O,

[0032] S, Si, Se, P, B, Ge.

[0033] According to some embodiments of the present invention, A1, A2, A3, A4, A5, A6, A7, A8, A9, A 10 , A 11Each independently represents CR; R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', 2- an alkenyl group having 20 carbon atoms, an alkynyl group having 2-20 carbon atoms which may or may not contain a substituent R', an aryl group having 6-30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3-30 carbon atoms which may or may not contain a substituent R', a substituted or unsubstituted alkylsilyl group having 3-30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-30 carbon atoms, a substituted or unsubstituted amino group having 0-30 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0034] According to some embodiments of the invention, R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1-30 carbon atoms with or without substituent R', cycloalkyl having 3-30 carbon atoms with or without substituent R', aryl having 6-30 carbon atoms with or without substituent R', heteroaryl having 3-30 carbon atoms with or without substituent R', amino having 0-30 carbon atoms with or without substituent R', and combinations thereof;

[0035] According to some embodiments of the invention, R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1-10 carbon atoms with or without substituent R', cycloalkyl having 3-12 carbon atoms with or without substituent R', aryl having 6-20 carbon atoms with or without substituent R', heteroaryl having 3-20 carbon atoms with or without substituent R', amino having 0-20 carbon atoms with or without substituent R', and combinations thereof;

[0036] According to some embodiments of the present invention, R is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, pentyl, phenyl with or without substituent R', carbazolyl with or without substituent R', diphenylamino with or without substituent R', cyclohexyl; the substituent R' is selected from deuterium, halogen, methyl, ethyl, propyl, isopropyl, phenyl.

[0037] According to some embodiments of the present invention, A1, A2, A3, A4, A5, A6, A7, A8, A9, A 10 , A 11Each independently represents CR; A1, A4, A5, A7, A8, A 11 Where R is hydrogen; A3, A6, A9, A 10 wherein R is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', The invention also includes an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms with or without substituent R', an aryl group having 6 to 30 carbon atoms with or without substituent R', a heteroaryl group having 3 to 30 carbon atoms with or without substituent R', a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0038] According to some embodiments of the present invention, R in A2, A3, A6, and A9 is independently selected from an alkyl group having 1 to 5 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 8 carbon atoms with or without a substituent R', an aryl group having 6 to 12 carbon atoms with or without a substituent R', a heteroaryl group having 6 to 15 carbon atoms with or without a substituent R', and an amino group having 10 to 20 carbon atoms with or without a substituent R'; the substituent R' is selected from deuterium, halogen, and an alkyl group having 1 to 5 carbon atoms; any two adjacent groups in the substituent R' may or may not be connected to form a ring;

[0039] According to some embodiments of the present invention, R in A2, A3, A6, and A9 is each independently selected from methyl, ethyl, propyl, isopropyl, butyl, pentyl, phenyl with or without substituent R', carbazolyl with or without substituent R', diphenylamino with or without substituent R', and cyclohexyl; and the substituent R' is selected from deuterium, halogen, methyl, ethyl, propyl, isopropyl, and phenyl.

[0040] According to some embodiments of the present invention, A 10 R is selected from diphenylamino with or without substituent R', methyl, ethyl, propyl, isopropyl, butyl, pentyl, phenyl with or without substituent R'; substituent R' is selected from deuterium, halogen, methyl, ethyl, propyl, isopropyl, phenyl.

[0041] According to some embodiments of the present invention, in the compound, R, R N , Ra and Rb are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 20 carbon atoms with or without substituent R', cycloalkyl with 3 to 20 carbon atoms with or without substituent R', heteroalkyl with 1 to 20 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 20 carbon atoms with or without substituent R', alkoxy with 1 to 20 carbon atoms with or without substituent R', aryloxy with 6 to 20 carbon atoms with or without substituent R', alkenyl with 2 to 10 carbon atoms with or without substituent R' , an alkynyl group having 2 to 10 carbon atoms which may be included in the substituent R', an aryl group having 6 to 30 carbon atoms which may be included in the substituent R', a heteroaryl group having 3 to 30 carbon atoms which may be included in the substituent R', an alkylsilyl group having 3 to 20 carbon atoms which may be included in the substituent R', an arylsilyl group having 6 to 20 carbon atoms which may be included in the substituent R', an amino group having 0 to 20 carbon atoms which may be included in the substituent R', an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, a diarylboryl group which may be included in the substituent R', and combinations thereof;

[0042] The R, R N , Ra and Rb are substituted with one or more substituents R';

[0043] The substituent R' is selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0044] R, R N Any two adjacent groups in Ra and Rb may be connected to form a ring or not.

[0045] According to some embodiments of the present invention, R, R N , Ra and Rb are the same or different, R, R N , Ra and Rb are each independently selected from the group consisting of: hydrogen, deuterium, halogen, alkyl with 1-10 carbon atoms with or without substituent R', cycloalkyl with 3-10 carbon atoms with or without substituent R', heteroalkyl with 1-10 carbon atoms with or without substituent R', heterocycloalkyl with 3-10 carbon atoms with or without substituent R', aryl with 6-30 carbon atoms with or without substituent R', alkylsilyl with 3-10 carbon atoms with or without substituent R', amino with 0-20 carbon atoms with or without substituent R';

[0046] The substituent R' is selected from deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0047] According to some embodiments of the present invention, R, R N , Ra and Rb are the same or different, R, R N , Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1-10 carbon atoms with or without substituent R', cycloalkyl with 3-10 carbon atoms with or without substituent R', heteroalkyl with 1-10 carbon atoms with or without substituent R', heterocycloalkyl with 3-10 carbon atoms with or without substituent R', aryl with 6-30 carbon atoms with or without substituent R', alkylsilyl with 3-10 carbon atoms with or without substituent R', diarylamino with or without substituent R', diheteroarylamino with or without substituent R', arylheteroarylamino with or without substituent R';

[0048] The substituent R' is selected from deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0049] According to some embodiments of the present invention, R, R N , Ra and Rb are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 10 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 10 carbon atoms with or without a substituent R', a heteroalkyl group having 1 to 10 carbon atoms with or without a substituent R', a heterocycloalkyl group having 3 to 10 carbon atoms with or without a substituent R', and the following structures:

[0050]

[0051]

[0052] In some preferred embodiments, the compound is selected from the compounds corresponding to numbers C1 to C136:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] In a second aspect, the present invention provides use of the above-mentioned boron-containing organic compound in the preparation of an organic electroluminescent device.

[0061] Preferably, the boron-containing organic compound is used as a blue light doping material of a light-emitting layer in an organic electroluminescent device.

[0062] In some embodiments, the doping concentration (mass percentage) of the doping material is 1wt% to 20wt% relative to the main material in the light-emitting layer, for example, 1wt%, 3wt%, 6wt%, 9wt%, 12wt%, 15wt%, 18wt%, 20wt% or any value therebetween.

[0063] According to some embodiments of the present invention, the doping concentration (mass percentage) of the doping material is 1 wt% to 10 wt%, more preferably 2 wt% to 8 wt% relative to the host material in the light-emitting layer.

[0064] In a third aspect, the present invention provides an organic electroluminescent device, comprising a light-emitting layer, wherein the doping material of the light-emitting layer contains the boron-containing organic compound of the present invention.

[0065] Preferably, the organic electroluminescent device comprises: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. In some embodiments, the light-emitting layer further comprises a doping material.

[0066] Preferably, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0067] In a fourth aspect, the present invention provides a display component / device, which comprises the boron-containing organic compound described in the first aspect of the present invention or the organic electroluminescent device described in the third aspect of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0068] Figure 1 FIG. 4 is a schematic diagram of an organic light-emitting device in a specific embodiment of the present invention.

[0069] Figure 2 FIG. 4 is a schematic diagram of an organic light-emitting device in another specific embodiment of the present invention.

[0070] The reference numerals are as follows:

[0071] 100. First organic light-emitting device, 101. Substrate, 110. Anode, 120. Hole injection layer, 130. Hole transport layer, 140. Electron blocking layer, 150. Light-emitting layer, 160. Hole blocking layer, 170. Electron transport layer, 180. Electron injection layer, 190. Cathode, 102. Encapsulation layer, 200. Second organic light-emitting device. DETAILED DESCRIPTION

[0072] The technical scheme of the present invention is described in detail below through specific examples. The following examples are used to illustrate the present invention, but are not used to limit the scope of the present invention. Any other equivalent changes or modifications completed without departing from the spirit disclosed by the present invention should be included in the scope of the claims.

[0073] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 The first organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure can be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent US7,279,704B2, the entire contents of which are incorporated herein by reference.

[0074] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated by reference in its entirety.

[0075] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0076] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0077] OLED also requires encapsulation layers, such as Figure 2 The second organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0078] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0079] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0080] Definition of Substituent Terms

[0081] As used herein, the term "halogen or halide" includes fluorine, chlorine, bromine and iodine.

[0082] The term "alkyl" as used herein includes straight and branched alkyl groups. The alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group can be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group can be optionally substituted.

[0083] As used herein, the term "alkenyl" is a straight chain, branched or cyclic non-aromatic hydrocarbon group containing one or more carbon-carbon double bonds. Alkenyl can be a straight chain, branched or cyclic non-aromatic hydrocarbon group having 2-20 carbon atoms and one or more carbon-carbon double bonds, preferably an alkenyl group having 2-12 carbon atoms, including but not limited to vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, isobutenyl, butadienyl, 1-pentenyl, 2-pentenyl, isopentenyl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1,3-hexadienyl, 1,4-hexadienyl, 1,5-hexadienyl, 2,4-hexadienyl or 1,3,5-hexatrienyl, etc. In addition, alkenyl can be optionally substituted.

[0084] The term "cycloalkyl" as used herein includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.

[0085] As used herein, term " heteroalkyl " comprises that one or more carbon atoms in alkyl chain are selected from the heteroatom replacement of the group consisting of nitrogen-atom, oxygen-atom, sulphur-atom, selenium-atom, phosphorus-atom, silicon-atom, germanium-atom and boron-atom. Heteroalkyl can be heteroalkyl with 1 to 20 carbon atoms, preferably heteroalkyl with 1 to 10 carbon atoms, more preferably heteroalkyl with 1 to 6 carbon atoms. The example of heteroalkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminoinyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.

[0086] The term "carbocyclyl" as used herein can be used interchangeably with "carbocycle" to refer to a non-aromatic saturated or partially unsaturated monocyclic or polycyclic ring system consisting of carbon atoms as ring atoms, and also includes an aromatic ring consisting of carbon atoms as ring atoms. In addition, the carbocyclyl can be optionally substituted.

[0087] The term "heterocyclic group" as used herein is used interchangeably with "heterocycle", "carboheterocyclic ring", and "carboheterocyclic group", and includes aromatic cyclic groups and non-aromatic cyclic groups. Aromatic cyclic groups include heteroaromatic cyclic groups having 3-18 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-30 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-30 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolane, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepineyl, azepineyl and tetrahydrothiazolyl. In addition, the heterocyclic group may be optionally substituted.

[0088] The term "aryl or aromatic group" as used herein includes both non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, biphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.

[0089] The term "heteroaryl" as used herein includes non-fused and fused heteroaromatic groups of 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoxazole, benzothiazole, quinoline, isoxazole, benzofuran, benzothi ...furan, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran Quinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and aza analogs thereof. In addition, the heteroaryl group may be optionally substituted.

[0090] As used herein, the term "alkoxy" is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy may be optionally substituted.

[0091] The term "aryloxy" as used herein is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy may be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, the aryloxy may be optionally substituted.

[0092] The term "aralkyl" as used herein encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl ... substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0093] The term "alkylsilyl or silyl" as used herein encompasses silyl groups substituted by the groups listed above for the alkyl group, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0094] The term "arylsilyl group" used herein is meant to encompass a group consisting of any of the aforementioned aryl groups and silyl groups.

[0095] The term "aza" in the terms "azadibenzofuran, azadibenzothiophene" and the like as used herein refers to one or more CH groups in the corresponding aromatic fragment being replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by one of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0096] The term "diarylboryl" as used herein means that two aryl groups may be bonded via a single bond or a linking group.

[0097] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of the following is used, for example, substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted The invention also includes but is not limited to substituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0098] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0099] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0100] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0101] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0102] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122M, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0103] The materials described herein as being useful in a specific layer in an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example,

[0104] The compounds disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273M, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0105] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Agilent's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to the evaporation machine produced by Nanjing Institute of Micro-Science, the optical test system and life test system produced by Suzhou Fushida, the ellipsometer produced by Wuhan Yiguang Technology, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents will not be elaborated in this patent.

[0106] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0107] Synthesis Example 1: Synthesis of Compound C2

[0108]

[0109] The synthetic route is as follows:

[0110]

[0111] Specific synthesis steps:

[0112] (1) In a 500 mL three-necked flask equipped with a magnetic stirrer, 23.3 g (0.1 mol) of the compound 2-bromo-3-methoxy-5-methylthiophenol, 20.8 g (0.1 mol) of 7-tert-butyl-4-fluorobenzo[b]thiophene and 65.3 g (0.2 mol) of cesium carbonate were dissolved in 200 mL of N,N-dimethylacetamide under nitrogen and stirred at 140-150° C. for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, the reaction mixture was diluted with toluene and poured into water. The organic phase was separated, the aqueous phase was extracted twice with toluene, and the organic phases were combined. The organic phase was washed with water twice, dried over anhydrous magnesium sulfate, column chromatography, the solvent was spin-dried, slurried with ethanol and heptane, filtered, and dried to obtain 35.8 g of yellow solid compound C2-1 with a yield of 85%.

[0113] (2) A 1000 mL three-necked flask was equipped with a magnetic stirrer. After nitrogen replacement, 42.1 g (0.1 mol) of compound C2-1 and 400 mL of dichloromethane were added in sequence. Stirring was started, the temperature was lowered to 0°C, and 75.2 g (0.3 mol) of boron tribromide was added dropwise. The mixture was warmed to room temperature and reacted for 12 hours. 200 mL of water was added, the liquid was extracted and separated, the organic phase was collected, dried, filtered, and chromatographed on a n-heptane:ethyl acetate (4:1) column. The solvent was spin-dried, the heptane was slurried, and dried to obtain 36.6 g of light yellow solid C2-2, with a yield of 90%.

[0114] (3) Under nitrogen protection, 200 mL of toluene, 14.9 g (0.1 mol) of p-tert-butylaniline, 21.3 g (0.1 mol) of p-tert-butylbromobenzene, 14.4 g (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium, and 0.3 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask, and the temperature was slowly raised to 95-100° C. under stirring, and the reaction was carried out for 2 hours. After the reaction solution was cooled, 8 mL of hydrochloric acid and 100 mL of water were added to acidify it, and the liquid was separated. The organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 24.7 g of C2-3 product with a yield of 88%.

[0115] (4) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, then add 16.5 g (0.1 mol) of m-fluorobromobenzene, 28.2 g (0.1 mol) of intermediate C2-3, 0.18 g of tri(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 4 hours. Cool the reaction solution by 50°C, add 80 mL of water, wash with water, column chromatography, recrystallize, and dry to obtain 31.8 g of C2-4 product with a yield of 85%.

[0116] (5) In a 1000 mL three-necked flask equipped with a magnetic stirrer, 40.7 g (0.1 mol) of compound C2-2, 37.5 g (0.1 mol) of C2-4 and 65.3 g (0.2 mol) of cesium carbonate were dissolved in 400 mL of N,N-dimethylacetamide under nitrogen and stirred at 140-150°C for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, the reaction mixture was diluted with toluene and poured into water. The organic phase was separated, the aqueous phase was extracted twice with toluene, and the organic phases were combined. The organic phase was washed with water twice, dried over anhydrous magnesium sulfate, column chromatography, the solvent was spin-dried, slurried with ethyl acetate and heptane, filtered, and dried to obtain 67.9 g of yellow solid compound C2-5 with a yield of 89%.

[0117] (6) Under nitrogen protection, add 160 mL of analytical pure xylene to a 250 mL reaction bottle, stir and add 7.6 g (0.01 mol) of intermediate C2-5, heat to about 55 ° C, cool to -30 ° C after dissolution, replace with nitrogen three times, and drop 6 mL of 2 mol / L n-butyl lithium. Slowly heat to 75 ° C and react for 2 hours. Cool to -25 ° C, add 3.0 g (0.012 mol) of boron tribromide, slowly heat to 60 ° C and keep warm for 3 hours. Cool to -20 ° C, drop 2.3 g of N, N-diisopropylethylamine. Slowly heat to 80 ° C and keep warm for 1 hour, then heat to 130 ° C and react for 12 hours. The reaction solution is cooled to 50 ° C, column chromatography, recrystallization, and drying to obtain 2.1 g of the product with a yield of 30%.

[0118] Product MS (m / e): 691; 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,4H), 6.0-7.0(m,12H), 2.0-2.5(m,3H), 1.0-2.0(m,27H).

[0119] Synthesis Example 2: Synthesis of Compound C7

[0120]

[0121] The synthetic route is as follows:

[0122]

[0123] Specific synthesis steps:

[0124] (1) In a 500 mL three-necked flask equipped with a magnetic stirrer, 35.7 g (0.1 mol) of the compound 2-bromo-5-tert-butyl-1-fluoro-3-iodobenzene, 15 g (0.1 mol) of benzo[b]thiophene-4-ol and 65.3 g (0.2 mol) of cesium carbonate were dissolved in 200 mL of N,N-dimethylacetamide under nitrogen and stirred at 140-150° C. for 10 hours. After the reaction was completed, the temperature was cooled to room temperature, the reaction mixture was diluted with toluene and poured into water. The organic phase was separated, the aqueous phase was extracted twice with toluene, and the organic phases were combined. The organic phase was washed with water twice, dried over anhydrous magnesium sulfate, column chromatography, the solvent was spin-dried, slurried with ethanol and heptane, filtered, and dried to obtain 41.9 g of yellow solid compound C7-1 with a yield of 86%.

[0125] (2) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 19.1 g (0.1 mol) of m-chlorobromobenzene, 28.2 g (0.1 mol) of intermediate C2-3, 0.18 g of tri(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 4 hours. The reaction solution is cooled by 50°C, 80 mL of water is added, washed with water, column chromatography, recrystallized, and dried to obtain 40 g of C7-2 product with a yield of 84%.

[0126] (3) Under nitrogen protection, 200 mL of toluene, 14.9 g (0.1 mol) of p-tert-butylaniline, 47.6 g (0.1 mol) of C7-2, 14.4 g (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium, and 0.3 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask, and the temperature was slowly raised to 95-100° C. under stirring, and the reaction was carried out for 4 hours. After the reaction solution was cooled, 8 mL of hydrochloric acid and 100 mL of water were added to make it acidic, and the liquid was separated. The organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 44.9 g of C7-3 product with a yield of 89%.

[0127] (4) Under nitrogen protection, add 400 mL of xylene to a 1000 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 48.7 g (0.1 mol) of C7-1, 50.5 g (0.1 mol) of intermediate C7-3, 0.18 g of tri(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C for 3 hours. The reaction solution is cooled by 50°C, 80 mL of water is added, washed with water, column chromatography, recrystallized, and dried to obtain 70.8 g of C7-4 product with a yield of 82%.

[0128] (5) Under nitrogen protection, add 160 mL of analytical pure xylene to a 250 mL reaction bottle, stir and add 8.6 g (0.01 mol) of intermediate C7-4, heat to about 55 ° C, cool to -30 ° C after dissolution, replace with nitrogen three times, and drop 6 mL of 2 mol / L n-butyl lithium. Slowly heat to 75 ° C and react for 2 hours. Cool to -25 ° C and add 3.0 g (0.012 mol) of boron tribromide, slowly heat to 60 ° C and keep warm for 3 hours. Cool to -20 ° C and drop 2.3 g of N, N-diisopropylethylamine. Slowly heat to 80 ° C and keep warm for 1 hour, then heat to 130 ° C and react for 12 hours. The reaction solution is cooled to 50 ° C, column chromatography, recrystallization, and drying to obtain 2.5 g of the product with a yield of 32%.

[0129] Product MS (m / e): 792, 1H NMR (400MHz, CDCl3): δ7.0-8.0(m,4H), 6.0-7.0(m,17H), 0.5-1.0(m,36H).

[0130] Synthesis Example 3: Synthesis of Compound C57

[0131]

[0132] Specific synthesis steps:

[0133] Use compound replace Use compound replace Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as those in Synthesis Example 2 to obtain compound C57; product MS (m / e): 826, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,9H), 6.0-7.0(m,16H), 2.0-2.5(m,3H), 1.0-2.0(m,27H).

[0134] Synthesis Example 4: Synthesis of Compound C37

[0135]

[0136] The synthetic route is as follows:

[0137]

[0138] Specific synthesis steps:

[0139] (1) Under nitrogen protection, 200 mL of toluene, 20.3 g (0.1 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine, 25.3 g (0.1 mol) of 4-bromo-7-tert-butylbenzofuran, 14.4 (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium, and 0.3 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask, and the temperature was slowly raised to 95-100° C. under stirring, and the reaction was carried out for 2 hours. After the reaction solution was cooled, 8 mL of hydrochloric acid and 100 mL of water were added to acidify it, and the liquid was separated. The organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 31.5 g of C37-1 product with a yield of 84%.

[0140] (2) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 37.5 g (0.1 mol) of C37-1, 37.6 g (0.1 mol) of 3,4-dibromo-5-iodotoluene, 0.18 g of tri(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C for reaction for 3 hours. Cool the reaction solution by 50°C, add 80 mL of water, wash with water, column chromatography, recrystallize, and dry to obtain 52.9 g of C37-2 product with a yield of 85%.

[0141] (3) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 19.1 g (0.1 mol) of m-chlorobromobenzene, 19.7 g (0.1 mol) of N-(2-methylphenyl)-2-methylaniline, 0.18 g of tris(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 4 hours. Cool the reaction solution by 50°C, add 80 mL of water, wash with water, column chromatography, recrystallize, and dry to obtain 25.6 g of C37-3 product with a yield of 86%.

[0142] (4) Under nitrogen protection, 200 mL of toluene, 14.9 g (0.1 mol) of p-tert-butylaniline, 30.8 g (0.1 mol) of C37-3, 14.4 g (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium, and 0.3 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask, and the temperature was slowly raised to 95-100° C. under stirring, and the reaction was carried out for 4 hours. After the reaction solution was cooled, 8 mL of hydrochloric acid and 100 mL of water were added to make it acidic, and the liquid was separated. The organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 36.1 g of C37-4 product with a yield of 86%.

[0143] (5) Under nitrogen protection, add 400 mL of xylene to a 1000 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 62.3 g (0.1 mol) of C37-2, 42.0 g (0.1 mol) of intermediate C37-4, 0.18 g of tris(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C for reaction for 3 hours. Cool the reaction solution by 50°C, add 80 mL of water, wash with water, column chromatography, recrystallize, and dry to obtain 78 g of C37-5 product with a yield of 81%.

[0144] (6) Under nitrogen protection, add 160 mL of analytical pure xylene to a 250 mL reaction bottle, stir and add 9.6 g (0.01 mol) of intermediate C37-5, heat to about 55 ° C, cool to -30 ° C after dissolution, replace with nitrogen three times, and drop 6 mL of 2 mol / L n-butyl lithium. Slowly heat to 75 ° C and react for 2 hours. Cool to -25 ° C, add 3.0 g (0.012 mol) of boron tribromide, slowly heat to 60 ° C and keep warm for 3 hours. Cool to -20 ° C, drop 2.3 g of N, N-diisopropylethylamine. Slowly heat to 80 ° C and keep warm for 1 hour, then heat to 130 ° C and react for 12 hours. The reaction solution is cooled to 50 ° C, column chromatography, recrystallization, and drying to obtain 2.75 g of the product with a yield of 31%.

[0145] Product MS (m / e): 891, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,3H), 6.0-7.0(m,20H), 2.0-2.5(m,9H), 1.0-2.0(m,22H), 0.5-1.0(m,12H).

[0146] Synthesis Example 5: Synthesis of Compound C65

[0147]

[0148] The synthetic route is as follows:

[0149]

[0150] Specific synthesis steps:

[0151] (1) Under nitrogen protection, 200 mL of toluene, 14.9 g (0.1 mol) of p-tert-butylaniline, 27.0 g (0.1 mol) of 4-bromo-7-tert-butylbenzo[b]thiophene, 14.4 g (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium, and 0.3 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask, and the temperature was slowly raised to 95-100° C. under stirring, and the reaction was carried out for 2 hours. After the reaction solution was cooled, 8 mL of hydrochloric acid and 100 mL of water were added to make it acidic, and the liquid was separated. The organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 28.6 g of C65-1 product with a yield of 85%.

[0152] (2) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 33.7 g (0.1 mol) of C65-1, 43.6 g (0.1 mol) of 3,4-dibromo-5-iodo-1,1'-biphenyl, 0.18 g of tri(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C for 3 hours. The reaction solution is cooled by 50°C, 80 mL of water is added, washed with water, column chromatographed, recrystallized, and dried to obtain 55.5 g of C65-2 product with a yield of 86%.

[0153] (3) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 19.1 g (0.1 mol) of m-chlorobromobenzene, 30.1 g (0.1 mol) of N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine, 0.18 g of tri(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 4 hours. The reaction solution is cooled by 50°C, 80 mL of water is added, washed with water, column chromatographed, recrystallized, and dried to obtain 34.2 g of C65-3 product with a yield of 83%.

[0154] (4) Under nitrogen protection, 200 mL of toluene, 14.9 g (0.1 mol) of p-tert-butylaniline, 41.2 g (0.1 mol) of C65-3, 14.4 g (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium, and 0.3 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask, and the temperature was slowly raised to 95-100° C. under stirring, and the reaction was carried out for 4 hours. After the reaction solution was cooled, 8 mL of hydrochloric acid and 100 mL of water were added to make it acidic, and the liquid was separated. The organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 44.1 g of C65-4 product with a yield of 84%.

[0155] (5) Under nitrogen protection, add 400 mL of xylene to a 1000 mL three-necked flask, stir and add 14.2 g (0.15 mol) of sodium tert-butoxide, 64.5 (0.1 mol) of C65-2, 52.4 g (0.1 mol) of intermediate C65-4, 0.18 g of tris(dibenzylideneacetone)dipalladium, and 0.22 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C for 3 hours. Cool the reaction solution by 50°C, add 80 mL of water, wash with water, column chromatography, recrystallize, and dry to obtain 87.3 g of C65-5 product with a yield of 80%.

[0156] (6) Under nitrogen protection, add 160 mL of analytical pure xylene to a 250 mL reaction bottle, stir and add 10.9 g (0.01 mol) of intermediate C65-5, heat to about 55 ° C, cool to -30 ° C after dissolution, replace with nitrogen three times, and drop 6 mL of 2 mol / L n-butyl lithium. Slowly heat to 75 ° C and react for 2 hours. Cool to -25 ° C and add 3.0 g (0.012 mol) of boron tribromide, slowly heat to 60 ° C and keep warm for 3 hours. Cool to -20 ° C and drop 2.3 g of N, N-diisopropylethylamine. Slowly heat to 80 ° C and keep warm for 1 hour, then heat to 130 ° C and react for 12 hours. The reaction solution is cooled to 50 ° C, column chromatography, recrystallization, and drying to obtain 3.38 g of product with a yield of 31%.

[0157] Product MS (m / e): 1019, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,15H), 6.0-7.0(m,19H), 1.0-2.0(m,36H).

[0158] Synthesis Example 6: Synthesis of Compound C70

[0159]

[0160] Specific synthesis steps:

[0161] Use compound replace Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as those in Synthesis Example 5 to obtain compound C70; product MS (m / e): 999, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,9H), 6.0-7.0(m,20H), 1.0-2.0(m,45H).

[0162] Synthesis Example 7: Synthesis of Compound C90

[0163]

[0164] Specific synthesis steps:

[0165] Use compound replace Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as those in Synthesis Example 5 to obtain compound C90; product MS (m / e): 1151, 1H NMR (400MHz, CDCl3): δ7.0-8.0(m,22H), 6.0-7.0(m,15H), 1.0-2.0(m,45H).

[0166] Synthesis Example 8: Synthesis of Compound C97

[0167]

[0168] Specific synthesis steps:

[0169] Use compound replace Use compound replace Select appropriate material ratio, other raw materials and steps are the same as Example 5, to obtain compound C97; product MS (m / e): 1075, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,13H), 6.0-7.0(m,18H), 1.0-2.0(m,31H), 0.5-1.0(m,12H).

[0170] Synthesis Example 9: Synthesis of Compound C98

[0171]

[0172] Specific synthesis steps:

[0173] Use compound replace Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as those in Synthesis Example 6 to obtain compound C98; product MS (m / e): 1000, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,11H), 6.0-7.0(m,15H), 1.0-2.0(m,31H), 0.5-1.0(m,12H).

[0174] Synthesis Example 10: Synthesis of Compound C106

[0175]

[0176] The synthetic route is as follows:

[0177]

[0178] Specific synthesis steps:

[0179] (1) Using compound replace Use compound replace Use compound replace An appropriate material ratio was selected, and other raw materials and steps were the same as those in Synthesis Example 7 to obtain intermediate C106-1.

[0180] (2) In a 500 mL three-necked flask equipped with a magnetic stirrer, 1.67 g (0.01 mol) of carbazole, 18.57 g (0.01 mol) of intermediate C106- and 6.53 g (0.02 mol) of cesium carbonate were dissolved in 100 mL of N,N-dimethylacetamide under nitrogen and stirred at 150-160°C for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, the reaction mixture was diluted with toluene and poured into water. The organic phase was separated, the aqueous phase was extracted twice with toluene, the organic phases were combined, dried over anhydrous magnesium sulfate, column chromatography, the solvent was spin-dried, slurried with ethyl acetate and heptane, filtered, and dried to obtain 7.3 g of compound C106 with a yield of 73%.

[0181] Product MS (m / e): 1003, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,13H), 6.0-7.0(m,8H), 1.0-2.0(m,45H).

[0182] Synthesis Example 11: Synthesis of Compound C111

[0183]

[0184] The synthetic route is as follows:

[0185]

[0186] Specific synthesis steps:

[0187] (1) Using compound replace Use compound replace An appropriate material ratio was selected, and other raw materials and steps were the same as those for the intermediate C106-1 in Synthesis Example 10 to obtain the intermediate C111-1.

[0188] (2) Under nitrogen protection, add 200 mL of xylene to a 500 mL three-necked flask, and stir to add 1.89 g (0.02 mol) of sodium tert-butoxide, 9.26 g (0.01 mol) of C111-1, 2.82 g (0.01 mol) of intermediate C2-3, 0.27 g of tri(dibenzylideneacetone)dipalladium, and 0.33 g of tri-tert-butylphosphine. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C for 4 hours. The reaction solution is cooled by 50°C, 80 mL of water is added, washed with water, column chromatography, recrystallized, and dried to obtain 8.2 g of C111 product with a yield of 70%.

[0189] Product MS (m / e): 1071, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,9H), 6.0-7.0(m,14H), 1.0-2.0(m,72H).

[0190] Synthesis Example 12: Synthesis of Compound C135

[0191]

[0192] Specific synthesis steps:

[0193] Use compound replace Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as those in Synthesis Example 7 to obtain compound C135; product MS (m / e): 1183, 1 H NMR (400MHz, CDCl3): δ7.0-8.0(m,24H), 6.0-7.0(m,5H), 1.0-2.0(m,49H), 0.5-1.0(m,12H).

[0194] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0195] Device Example 1

[0196] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 Torr's case The ITO anode was deposited sequentially by thermal vacuum deposition at a rate of 1.5 %. At the same time, the deposited compounds HT and NDP-9 (weight ratio 97:3) were used as the hole injection layer (HIL) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then, BH as a blue light host and the compound C2 of the present invention as a dopant (weight ratio 98:2) were co-evaporated to form an emitting layer (EML) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated (weight ratio 50:50) as an electron transport layer (ETL) with a thickness of Finally, evaporation 8-Hydroxyquinoline-lithium (Liq) with a thickness of 1000 nm was used as an electron injection layer (EIL), and a vapor deposition The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.

[0197] Device Example 2 to Device Example 12

[0198] The method is the same as that of device embodiment 1, except that the compounds C7, C57, C37, C65, C70, C90, C97, C98, C106, C111 and C135 of the present invention in synthesis examples 2-12 are used as doping materials instead of compound C2 of the present invention in the light-emitting layer (EML).

[0199] Device Comparison Example 1

[0200] The method is the same as that of device example 1, except that compound A is used as the doping material in the light emitting layer (EML) instead of compound C2 of the present invention.

[0201] The material structure used in the device is shown below:

[0202]

[0203] Table 1 lists the 2 Under the conditions, the current efficiency (CE) and life (T) were measured. In order to better show the data comparison, the CE and T data of Comparative Example 1 were set to 100%, and the CE and T data of Device Example 1 to Device Example 12 were converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0204] Table 1

[0205] Device ID Doping materials Voltage (V) CE(%) Lifespan (h) Example 1 C2 95％ 113％ 109％ Example 2 C7 97％ 117％ 104％ Example 3 C57 88％ 133％ 108％ Example 4 C37 89％ 112％ 115％ Example 5 C65 90％ 138％ 114％ Example 6 C70 96％ 131％ 115％ Example 7 C90 95％ 126％ 118％ Example 8 C97 94％ 135％ 128％ Example 9 C98 92％ 126％ 131％ Example 10 C106 90％ 130％ 143％ Embodiment 11 C111 91％ 131％ 123％ Example 12 C135 96％ 128％ 116％ Comparative Example 1 Compound A 100％ 100％ 100％

[0206] As shown in Table 1, at 10 mA / cm 2 Under current density, the voltage of device examples 1 to 12 can be reduced by 4 to 12%, the current efficiency is improved by 12% to 38%, and the device life is extended by 4% to 43% relative to device comparative example 1. The above data show that the seven-membered ring structure compound formed by a specific connection between a benzo pentacyclic ring and a boron-containing heteroaromatic ring structure has a lower driving voltage and higher current efficiency and life compared with the comparative example compound A due to the introduction of a seven-membered ring structure in the structure. This structural change brings about excellent device effects and unexpectedly proves the unique advantages of the compounds of the present invention.

[0207] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A boron-containing organic compound having a structure shown in Formula I: The Q1 ring and the Q2 ring are independently an aryl ring or a heteroaryl ring, and at least one hydrogen in the Q1 ring and the Q2 ring may be substituted by deuterium, halogen, an alkyl group with or without a substituent R', a cycloalkyl group with or without a substituent R', a heteroalkyl group with or without a substituent R', a heterocycloalkyl group with or without a substituent R', an alkoxy group with or without a substituent R', an aryloxy group with or without a substituent R', an alkenyl group with or without a substituent R', an alkynyl group with or without a substituent R', an aryl group with or without a substituent R', a heteroaryl group with or without a substituent R', an alkylsilyl group with or without a substituent R', an amino group with 0-30 carbon atoms with or without a substituent R', an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, or a boron group; A1, A2, A3, A4 each independently represent CR, N; X is selected from O, S, Se, NR N , CRaRb or SiRaRb; X1 and X2 are the same or different and are independently selected from O, S, Se, NR N , CRaRb or SiRaRb; R, R N , Ra and Rb are the same or different at each occurrence, R, R N , Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', aryloxy with 2 to 20 carbon atoms with or without substituent R' an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms which may or may not contain a substituent R', an aryl group having 6 to 30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an alkylsilyl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an arylsilyl group having 6 to 30 carbon atoms which may or may not contain a substituent R', an amino group having 0 to 30 carbon atoms which may or may not contain a substituent R', an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Q1 ring, Q2 ring, R, R N , Ra and Rb are substituted with one or more substituents R'; The Q1 ring, Q2 ring, R, R N , Ra and Rb, the substituent R' is selected from deuterium, halogen, alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 carbon atoms, aryl having 6-30 carbon atoms or heteroaryl having 3-30 carbon atoms; R, R N Any two adjacent groups in Ra and Rb may be connected to form a ring or not; Q1 ring, Q2 ring, R, R N In , Ra, Rb, and R', at least one heteroatom of the heteroaryl ring, heteroalkyl, heteroaryl, and heterocycloalkyl is independently selected from N, O, S, Si, Se, P, B, and Ge.

2. The boron-containing organic compound according to claim 1, characterized in that At least one hydrogen in the Q1 ring and the Q2 ring may be replaced by deuterium, halogen, an alkyl group having 1 to 30 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', a heteroalkyl group having 1 to 30 carbon atoms with or without a substituent R', a heterocycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', an alkoxy group having 1 to 30 carbon atoms with or without a substituent R', an aryloxy group having 6 to 30 carbon atoms with or without a substituent R', an alkene group having 2 to 20 carbon atoms with or without a substituent R'. substituted with an alkyl group, an alkynyl group having 2 to 20 carbon atoms which may be substituted with R', an aryl group having 6 to 30 carbon atoms which may be substituted with R', a heteroaryl group having 3 to 30 carbon atoms which may be substituted with R', an alkylsilyl group having 3 to 30 carbon atoms which may be substituted with R', an arylsilyl group having 6 to 30 carbon atoms which may be substituted with R', an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, or a boronyl group which may be substituted with R'; Preferably, the Q1 ring and the Q2 ring are each independently an aryl ring having 6 to 12 carbon atoms or a heteroaryl ring having 2 to 6 carbon atoms; Preferably, the Q1 ring and the Q2 ring are each independently a benzene ring; Preferably, at least one hydrogen in the Q1 ring and the Q2 ring may be replaced by deuterium, halogen, an alkyl group having 1 to 30 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', a heteroalkyl group having 1 to 30 carbon atoms with or without a substituent R', a heterocycloalkyl group having 3 to 30 carbon atoms with or without a substituent R', an alkoxy group having 1 to 30 carbon atoms with or without a substituent R', an aryloxy group having 6 to 30 carbon atoms with or without a substituent R', a cycloalkyl group having 2 to 20 carbon atoms with or without a substituent R' substituted with an alkenyl group, an alkynyl group having 2 to 20 carbon atoms which may or may not contain a substituent R', an aryl group having 6 to 30 carbon atoms which may or may not contain a substituent R', a heteroaryl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an alkylsilyl group having 3 to 30 carbon atoms which may or may not contain a substituent R', an arylsilyl group having 6 to 30 carbon atoms which may or may not contain a substituent R', an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, or a boron group which may or may not contain a substituent R'; The substituent R' substituted in the Q1 ring and the Q2 ring is one or more; The substituent R' substituted in the Q1 ring and Q2 ring is selected from deuterium, halogen, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms.

3. The boron-containing organic compound according to claim 1 or 2, characterized in that The compound has a structure represented by any one of the following formulae 1-1 to 1-16: In formulas 1-1 to 1-16, A1, A2, A3, A4, X, R, R N , Ra and Rb are defined in the same way as in Formula 1. A5, A6, A7, A8, A9, A 10 , A 11 Definitions are the same as A1, A2, A3, A4 in Formula 1; X is selected from O, S, NR N or CRaRb; In the compound, R and R N , Ra and Rb are the same or different and are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms with or without a substituent R', an aryl group having 6 to 30 carbon atoms with or without a substituent R', a heteroaryl group having 3 to 30 carbon atoms with or without a substituent R', an alkylsilyl group having 3 to 30 carbon atoms with or without a substituent R', an arylsilyl group having 6 to 30 carbon atoms with or without a substituent R', an amino group having 0 to 30 carbon atoms with or without a substituent R', an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R, R N , Ra and Rb are substituted with one or more substituents; R, R N , the substituent R' in Ra and Rb is selected from deuterium, halogen, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms or heteroaryl having 3 to 30 carbon atoms; R, R N Any two adjacent groups in Ra and Rb may be connected to form a ring or not; R, R N In , Ra, Rb, and R', at least one heteroatom of the heteroaryl ring, heteroalkyl, heteroaryl, and heterocycloalkyl is independently selected from N, O, S, Si, Se, P, B, and Ge; Preferably, A1, A2, A3, A4, A5, A6, A7, A8, A9, A 10 , A 11 Each independently represents CR; R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 30 carbon atoms with or without substituent R', cycloalkyl with 3 to 30 carbon atoms with or without substituent R', heteroalkyl with 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 30 carbon atoms with or without substituent R', alkoxy with 1 to 30 carbon atoms with or without substituent R', aryloxy with 6 to 30 carbon atoms with or without substituent R', atom, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms which may be included in the substituent R', an aryl group having 6 to 30 carbon atoms which may be included in the substituent R', a heteroaryl group having 3 to 30 carbon atoms which may be included in the substituent R', an alkylsilyl group having 3 to 30 carbon atoms which may be included in the substituent R', an arylsilyl group having 6 to 30 carbon atoms which may be included in the substituent R', an amino group having 0 to 30 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, a boronyl group and combinations thereof which may be included in the substituent R'; Preferably, R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1 to 30 carbon atoms with or without substituent R', cycloalkyl having 3 to 30 carbon atoms with or without substituent R', aryl having 6 to 30 carbon atoms with or without substituent R', heteroaryl having 3 to 30 carbon atoms with or without substituent R', amino having 0 to 30 carbon atoms with or without substituent R', and combinations thereof; Preferably, R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1 to 10 carbon atoms with or without substituent R', cycloalkyl having 3 to 12 carbon atoms with or without substituent R', aryl having 6 to 20 carbon atoms with or without substituent R', heteroaryl having 3 to 20 carbon atoms with or without substituent R', amino having 0 to 20 carbon atoms with or without substituent R', and combinations thereof; Preferably, R is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, pentyl, phenyl with or without substituent R', carbazolyl with or without substituent R', diphenylamino with or without substituent R', cyclohexyl; substituent R' is selected from deuterium, halogen, methyl, ethyl, propyl, isopropyl, phenyl; Preferably, A1, A2, A3, A4, A5, A6, A7, A8, A9, A 10 , A 11 Each independently represents CR; A1, A4, A5, A7, A8, A 11 Where R is hydrogen; A3, A6, A9, A 10 wherein R is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1 to 30 carbon atoms with or without substituent R', cycloalkyl having 3 to 30 carbon atoms with or without substituent R', heteroalkyl having 1 to 30 carbon atoms with or without substituent R', heterocycloalkyl having 3 to 30 carbon atoms with or without substituent R', alkoxy having 1 to 30 carbon atoms with or without substituent R', aryloxy having 6 to 30 carbon atoms with or without substituent R', alkenyl, alkynyl with 2-20 carbon atoms which may contain R' as a substituent, aryl with 6-30 carbon atoms which may contain R' as a substituent, heteroaryl with 3-30 carbon atoms which may contain R' as a substituent, alkylsilyl with 3-30 carbon atoms which may contain R' as a substituent, arylsilyl with 6-30 carbon atoms which may contain R' as a substituent, amino with 0-30 carbon atoms which may contain R' as a substituent, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, boronyl, and combinations thereof; Preferably, R in A2, A3, A6, A9 is independently selected from an alkyl group having 1-5 carbon atoms with or without a substituent R', a cycloalkyl group having 3-8 carbon atoms with or without a substituent R', an aryl group having 6-12 carbon atoms with or without a substituent R', a heteroaryl group having 6-15 carbon atoms with or without a substituent R', and an amino group having 10-20 carbon atoms with or without a substituent R'; the substituent R' is selected from deuterium, halogen, and an alkyl group having 1-5 carbon atoms; any two adjacent groups in the substituent R' may or may not be connected to form a ring; Preferably, R in A2, A3, A6, and A9 is independently selected from methyl, ethyl, propyl, isopropyl, butyl, pentyl, phenyl with or without substituent R', carbazolyl with or without substituent R', diphenylamino with or without substituent R', and cyclohexyl; and substituent R' is selected from deuterium, halogen, methyl, ethyl, propyl, isopropyl, and phenyl; Preferably, A 10 R is selected from diphenylamino with or without substituent R', methyl, ethyl, propyl, isopropyl, butyl, pentyl, phenyl with or without substituent R'; substituent R' is selected from deuterium, halogen, methyl, ethyl, propyl, isopropyl, phenyl.

4. The boron-containing organic compound according to any one of claims 1 to 3, characterized in that In the compound, R and R N , Ra and Rb are the same or different, R, R N , Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1 to 20 carbon atoms with or without substituent R', cycloalkyl with 3 to 20 carbon atoms with or without substituent R', heteroalkyl with 1 to 20 carbon atoms with or without substituent R', heterocycloalkyl with 3 to 20 carbon atoms with or without substituent R', alkoxy with 1 to 20 carbon atoms with or without substituent R', aryloxy with 6 to 20 carbon atoms with or without substituent R', alkenyl with 2 to 10 carbon atoms with or without substituent R', an alkynyl group having 2 to 10 carbon atoms without R' as a substituent, an aryl group having 6 to 30 carbon atoms with or without R' as a substituent, a heteroaryl group having 3 to 30 carbon atoms with or without R' as a substituent, an alkylsilyl group having 3 to 20 carbon atoms with or without R' as a substituent, an arylsilyl group having 6 to 20 carbon atoms with or without R' as a substituent, an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, a diarylboryl group with or without R' as a substituent, and combinations thereof; The R, R N , Ra and Rb are substituted with one or more substituents R'; The substituent R' is selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; R, R N Any two adjacent groups in Ra and Rb may be connected to form a ring or not; Preferably, R, R N , Ra and Rb are the same or different, R, R N , Ra and Rb are each independently selected from the group consisting of: hydrogen, deuterium, halogen, alkyl with 1-10 carbon atoms with or without substituent R', cycloalkyl with 3-10 carbon atoms with or without substituent R', heteroalkyl with 1-10 carbon atoms with or without substituent R', heterocycloalkyl with 3-10 carbon atoms with or without substituent R', aryl with 6-30 carbon atoms with or without substituent R', alkylsilyl with 3-10 carbon atoms with or without substituent R', amino with 0-20 carbon atoms with or without substituent R'; The substituent R' is selected from deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; Preferably, R, R N , Ra and Rb are the same or different, R, R N , Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl with 1-10 carbon atoms with or without substituent R', cycloalkyl with 3-10 carbon atoms with or without substituent R', heteroalkyl with 1-10 carbon atoms with or without substituent R', heterocycloalkyl with 3-10 carbon atoms with or without substituent R', aryl with 6-30 carbon atoms with or without substituent R', alkylsilyl with 3-10 carbon atoms with or without substituent R', diarylamino with or without substituent R', diheteroarylamino with or without substituent R', arylheteroarylamino with or without substituent R'; The substituent R' is selected from deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

5. The boron-containing organic compound according to any one of claims 1 to 4, characterized in that In the compound, R and R N , Ra and Rb are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 10 carbon atoms with or without a substituent R', a cycloalkyl group having 3 to 10 carbon atoms with or without a substituent R', a heteroalkyl group having 1 to 10 carbon atoms with or without a substituent R', a heterocycloalkyl group having 3 to 10 carbon atoms with or without a substituent R', and the following structures:

6. The boron-containing organic compound according to any one of claims 1 to 5, characterized in that The compound is selected from the compounds corresponding to numbers C1 to C136:

7. Use of the boron-containing organic compound according to any one of claims 1 to 6 in preparing an organic electroluminescent device; Preferably, the boron-containing organic compound is used as a blue light doping material of a light-emitting layer in an organic electroluminescent device.

8. The use according to claim 7, characterized in that: The doping concentration of the doping material is 1 wt% to 20 wt%, preferably 1 wt% to 10 wt%, and more preferably 2 wt% to 8 wt%, relative to the host material in the light-emitting layer.

9. An organic electroluminescent device, comprising a light-emitting layer, wherein the doping material of the light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 6; Preferably, the organic electroluminescent device comprises: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode; Preferably, the light-emitting layer further includes a doping material; Preferably, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

10. A display component and / or device comprising the boron-containing organic compound according to any one of claims 1 to 6 or the organic electroluminescent device according to claim 9.

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