Organic compound containing boron and nitrogen and application of organic compound in organic electronic device

Abstract

The invention provides an organic compound containing boron and nitrogen and application of the organic compound in an organic electronic device, the organic compound containing boron and nitrogen has a general formula represented by a combination of a structure (I-1) and a structure (I-2), and the organic compound containing boron and nitrogen is applied to the organic device. The device using the organic compound containing boron and nitrogen has high luminous efficiency, narrow luminescent spectrum FWHM, long service life and the like. # imgabs0 #

Description

A boron-nitrogen-containing organic compound and its application in organic electronic devices Technical Field

[0001] The present technology relates to the technical field of organic electronic materials and devices, and in particular to an organic compound containing boron and nitrogen, a polymer, a mixture, a composition thereof, and applications thereof in organic electronic devices, in particular in organic electroluminescent devices. Background Art

[0002] Since organic semiconductor materials are diverse in chemical synthesis, have relatively low manufacturing costs in large-scale production, and have excellent optical and electrical properties, their optoelectronic devices, especially organic light-emitting diodes (OLEDs), have great application potential in the display field.

[0003] In OLED displays, various colors are expressed by mixing the three primary colors of light, namely red, green, and blue. However, if the color purity of each of the three primary colors is low, it is not possible to reproduce many colors, resulting in a significant reduction in the image quality of the display. Therefore, in commercially available displays, the color purity is improved by removing unnecessary colors from the self-luminous spectrum using an optical filter. If the original spectrum width is wide, the removal ratio increases. Therefore, even when the luminous efficiency is high, the actual luminous efficiency is greatly reduced. For example, the width of the half maximum (FWHM) of the blue emission spectrum of commercially available smartphones is about 20 to 25 nm, but the FWHM value of a general fluorescent material is about 40 to 60 nm, the FWHM value of a phosphorescent material is about 60 to 90 nm, and if it is a TADF material, the FWHM value is about 70 to 100 nm. When a fluorescent material is used, since the FWHM width is relatively narrow, it is sufficient to remove only a portion of the unnecessary colors. However, when a phosphorescent material or a TADF material is used, more than half of the colors need to be removed, and the actual luminous efficiency is greatly reduced.

[0004] Since Hatakeyama et al. first reported narrow-spectrum blue-emitting BN compounds in 2016 (DOI: 10.1002 / adma.201505491), these compounds have garnered widespread attention. Boron-nitrogen compounds exhibit a multiresonance effect, which maintains their molecular structure within a unique planar, rigidly conjugated structure. The different electronegativity of the boron atom's uniquely conjugated electron orbitals and the nitrogen atom's lone pairs enhance each other through the conjugation effect, forming short-range charge transfer states within the molecule. This enables efficient luminescence with thermally activated delayed fluorescence (TADF) properties. Furthermore, compared to other luminescent materials (such as traditional fluorescent materials), the planar structure of boron-nitrogen compounds is characterized by a high degree of convergence of the energy levels of their molecular vibrational modes, resulting in a significantly narrower full width at half maximum (FWHM) of their luminescence spectrum, thus contributing to high color purity. Because boron nitride compounds have high device efficiency, high color purity and potentially high device stability, this type of material has received high attention from academia and industry and is one of the hottest topics in the field of OLED luminescent materials.

[0005] However, for boron-nitrogen compounds, the width of their luminescence spectrum (FWHM) and the level of luminescence efficiency often depend on whether the vibrational and rotational degrees of freedom of the molecular groups can be effectively suppressed. For example, for currently developed boron-nitrogen compounds (structures shown in formulas a to e below), due to the large torsion angle between the phenyl group attached to the nitrogen atom and the rigid conjugated plane of boron and nitrogen, the phenyl group does not directly participate in the superresonance effect of the rigid conjugated plane of boron and nitrogen and cannot directly participate in the luminescence process of the boron-nitrogen ring compound. Moreover, such phenyl groups often have large vibrational and rotational degrees of freedom, which has an adverse effect on narrowing the FWHM of the boron-nitrogen compound. There is still room for improvement in boron-nitrogen compounds to achieve higher luminescence efficiency, narrower FWHM, and longer device operating life.

[0006] Summary of the Invention

[0007] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide an organic compound containing boron and nitrogen, or a polymer, mixture, composition, organic electronic device and application thereof, aiming to solve the problems of efficiency and life span of existing OLEDs.

[0008] The technical solutions of the present invention are as follows:

[0009] A boron-nitrogen-containing organic compound, wherein the structure of the boron-nitrogen-containing organic compound is represented by a combination of chemical formula (I-1) and chemical formula (I-2):

[0010] Wherein: * represents the connection point of the fusion of chemical formula (I-1) and chemical formula (I-2); Q1 ring, Q2 ring, Q3 ring are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or substituted or unsubstituted fused ring structure; X1, X2 are independently selected from B, N, P, P=O or Al; Y1, Y2 are independently selected from C=O, N-R1, O, S, Se, P, P=O or P=S; Y3 is selected from C=O, N-R1, O, Se, P, P=O or P=S; V0, when it appears, is independently selected from C-R2 or N-R3;

[0011] R1-R3, at each occurrence, may be selected, identically or differently, from H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0012] The present invention also relates to a polymer comprising at least one first repeating unit, wherein the first repeating unit comprises at least one structure corresponding to the boron-nitrogen-containing organic compound as described above.

[0013] The present invention also relates to a composition comprising an organic solvent, and at least one boron-nitrogen-containing organic compound as described above or at least one polymer as described above.

[0014] The present invention further relates to a mixture comprising an organic compound containing boron and nitrogen as described above or a polymer as described above, and at least one organic functional material, wherein the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminophore and a host material.

[0015] The present invention further relates to an organic electronic device comprising at least one boron-nitrogen-containing organic compound as described above, or a polymer as described above, or a mixture as described above.

[0016] Beneficial Effects: By incorporating the boron-nitrogen-containing organic compound into an organic light-emitting device (OLED), the present invention enables the OLED to achieve high luminous efficiency, high color purity, high device stability, and a long device lifespan. The BON-containing organic compound according to the present invention primarily utilizes a large conjugated group as a modifying group to improve the optical properties of the BN backbone. By introducing a large conjugated group, i.e., the Q3 ring is fused to the BN core structure via a pentacyclic ring, the conjugation length of the BN molecule is extended, thereby improving molecular stability. Furthermore, by introducing different conjugated groups, the electron cloud density around adjacent B atoms can be adjusted, facilitating the adjustment of the molecule's luminescence spectrum. Furthermore, the large conjugated group improves the planar stacking effect of the molecule to a certain extent, reducing exciton annihilation in the device, thereby achieving the effect of adjusting the luminescent color of the organic compound and improving the efficiency and lifespan of the luminescent device. The inventors surprisingly discovered that, in certain cases, even with an increased conjugated structure, blue light emission can be maintained, resulting in an OLED with high luminous efficiency, high color purity, and a long device lifespan. DETAILED DESCRIPTION

[0017] The present invention provides an organic compound containing boron and nitrogen, which can be used as an organic light-emitting material in an organic light-emitting device, but is not limited thereto. The organic compound containing boron and nitrogen is optimized and selected to have at least high luminous efficiency, narrow luminous spectrum FWHM and long luminous lifetime.

[0018] In order to make the purpose, technical solutions and effects of the present invention clearer and more specific, the present invention will be further described in detail below in conjunction with specific embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention. The data ranges involved in the present invention should include end values ​​unless otherwise specified.

[0019] In the present invention, main body material, matrix material, host material and matrix material have the same meaning and can be interchanged.

[0020] In the present invention, guest material, luminescent material and emitter material have the same meaning and can be interchanged.

[0021] In the present invention, color converter, color conversion layer and CCL have the same meaning and can be interchanged.

[0022] In the present invention, composition, printing ink, ink and ink have the same meaning and can be interchanged.

[0023] In the present invention, "|substituted" means that a hydrogen atom in a compound is substituted by a substituent.

[0024] In the present invention, when the same substituent appears multiple times, each substituent may be independently selected from different groups.

[0025] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted with a substituent, it is understood that it is optionally substituted with a substituent acceptable in the art, and the substituent may be further substituted with a substituent acceptable in the art.

[0026] In the present invention, the "number of ring atoms" refers to the number of atoms that constitute the ring itself in a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0027] An aromatic group refers to a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group refers to an aromatic hydrocarbon group containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and particularly preferably selected from Si, N, P, O and / or S. A fused ring aromatic group refers to an aromatic group having two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., a fused ring. A fused heterocyclic aromatic group refers to a fused heterocyclic aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present invention, aromatic or heteroaromatic groups include not only aromatic ring systems, but also non-aromatic ring systems. Thus, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, and carbene are also considered aromatic or heterocyclic aromatic groups for the purposes of this invention. For the purposes of the present invention, fused aromatic or fused heteroaromatic ring systems include not only systems containing aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered aromatic ring systems for the purposes of this invention.

[0028] In the embodiments of the present invention, the energy level structure of the organic material, the singlet energy level S1, the resonance factor f1, the triplet energy level T1, the HOMO, and the LUMO play a key role. The determination of these energy levels is described below.

[0029] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0030] The singlet energy level S1 of an organic material can be determined by luminescence spectroscopy, and the triplet energy level T1 can be measured by low-temperature time-resolved luminescence spectroscopy. S1 and T1 can also be obtained by quantum simulation calculations (e.g., by time-dependent DFT), such as using the commercial software Gaussian 09W (Gaussian Inc.). Specific simulation methods can be found in WO2011141110 or described below in the Examples. ΔE ST Defined as (S1-T1).

[0031] It should be noted that the absolute values ​​of HOMO, LUMO, S1, and T1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. In the description of the embodiments of the present invention, the values ​​of HOMO, LUMO, S1, f1, and T1 are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0032] In the present invention, (HOMO-1) is defined as the second-highest occupied molecular orbital energy level, (HOMO-2) is the third-highest occupied molecular orbital energy level, and so on. (LUMO+1) is defined as the second-lowest unoccupied molecular orbital energy level, (LUMO+2) is the third-lowest occupied molecular orbital energy level, and so on.

[0033] The present invention relates to an organic compound containing boron and nitrogen. The structure of the organic compound containing boron and nitrogen is represented by a combination of chemical formula (I-1) and chemical formula (I-2):

[0034] Wherein: * represents the connection point of the fusion of chemical formula (I-1) and chemical formula (I-2); Q1 ring, Q2 ring, Q3 ring are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or substituted or unsubstituted fused ring structure; X1, X2 are independently selected from B, N, P, P = O or Al; Y1, Y2 are independently selected from C = O, N-R1, O, S, Se, P, P = O or P = S; Y3 is selected from C = O, N-R1, O, Se, P, P = O or P = S; V0 is independently selected from C-R2 or N-R3 at each occurrence; R1-R3, at each occurrence, may be the same or different and selected from H, D, or have 1 to 20 C atoms. a straight-chain alkyl, alkoxy or thioalkoxy group, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0035] In some embodiments, the Q1 ring, Q2 ring, and Q3 ring of the boron-nitrogen-containing organic compound are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.

[0036] In some embodiments, each occurrence of Q1 ring, Q2 ring, and Q3 ring may be selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 50 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 50 ring atoms, or a combination of these groups. In some embodiments, each occurrence of Q1 ring, Q2 ring, and Q3 ring may be selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 30 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 30 ring atoms, or a combination of these groups. In some preferred embodiments, each occurrence of Q1 ring, Q2 ring, and Q3 ring may be selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 20 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 20 ring atoms, or a combination of these groups. In some preferred embodiments, the Q1 ring, Q2 ring, and Q3 ring, when they appear each time, can be selected identically or differently from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 15 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 15 ring atoms, or a combination of these groups.

[0037] In some embodiments, X1 and X2 are selected from B or N.

[0038] In some preferred embodiments, the structure of the boron-nitrogen-containing organic compound is represented by a combination of Chemical Formula (I-1a) and Chemical Formula (I-2a):

[0039] Wherein, V0, Y1, Y2, Y3, Q1 ring, Q2 ring, Q3 ring, and * are defined as above.

[0040] In some preferred embodiments, the boron-nitrogen-containing organic compound has a structure as shown in one of the general formulas (II-1) to (II-10):

[0041] Wherein, the definitions of V0, Y1, Y2, Y3, Q1 ring and Q3 ring are the same as those described above, and the definition of V1 is the same as that of V0.

[0042] In some preferred embodiments, the boron-nitrogen-containing organic compound is selected from the general formula (II-1) to (II-6):

[0043] Wherein, the definitions of V0, Y1, Y2, Y3, Q1 ring, and Q3 ring are the same as above, and the definition of V1 is the same as that of V0

[0044] In other preferred embodiments, the boron-nitrogen-containing organic compound is selected from the general formula (II-7), (II-8) and (II-10):

[0045] For the purpose of the present invention, the present invention preferably relates to compounds that emit blue light. Therefore, compounds with a smaller effective conjugation length are preferred, such as compounds with the structures of general formula (II-1) to (II-6), (II-7), (II-8) and (II-10).

[0046] Compounds having the general formula (II-9) tend to emit green or blue-green light and are therefore not preferred structures in certain embodiments.

[0047] In some preferred embodiments, the boron-nitrogen-containing organic compound, the Q1 ring, the Q2 ring, and the Q3 ring, when each appears, are independently selected from one or more combinations of the following structures:

[0048] wherein V is independently selected from C-R4 or N-R5 at each occurrence; W is independently selected from B-R6, C(=O), N-R7, O, S, P, P=O or P=S at each occurrence; R4-R7 are the same or different when they occur and are selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 carbon atoms, or a substituted keto group having 1 to 20 carbon atoms, or a 2 to 2 carbon atoms; 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; wherein one or more of the groups can form a ring system with each other and / or the groups to which they are bonded.

[0049] In certain embodiments, the Q1 ring, the Q2 ring, and the Q3 ring are each independently selected from an aromatic ring system, a heteroaromatic ring system, or a fused-ring aromatic group.

[0050] In a preferred embodiment, the aromatic or heteroaromatic ring system is selected from the following groups:

[0051] Wherein: V and W are defined as above.

[0052] More preferably, the aromatic or heteroaromatic ring system is selected from:

[0053] Wherein: V and W are defined as above.

[0054] In a preferred embodiment, the condensed-ring aromatic group is selected from the group consisting of benzene, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; the condensed-ring heteroaromatic group is selected from the group consisting of benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

[0055] In certain embodiments, R1-R3, at each occurrence, may be independently selected from the following groups:

[0056] Wherein: V and W are defined as above; n2, n3, n4, and n5 are all integers greater than or equal to 1.

[0057] Furthermore, R1-R3, when each occurs, are independently selected from the following groups:

[0058] Among them: The H atoms on the ring can be further substituted.

[0059] In certain preferred embodiments, in the above-mentioned boron-nitrogen-containing organic compound, R1-R3 may be further selected from the following structural units or combinations thereof:

[0060] Where n1 is 1 or 2 or 3 or 4.

[0061] In a more preferred embodiment, the boron-nitrogen-containing organic compound is at least partially deuterated, preferably 10% of the H is deuterated, more preferably 20% of the H is deuterated, most preferably 30% of the H is deuterated, and most preferably 40% of the H is deuterated.

[0062] Specific examples of the boron-nitrogen-containing organic compounds according to the present invention are listed below, but are not limited thereto:

[0063] In certain preferred embodiments, the boron-nitrogen-containing organic compounds of the present invention are mainly divided into two categories. One category of compounds uses indolecarbazoles as modifying groups to modify the boron-nitrogen ring structure to adjust the optical properties of the existing boron-nitrogen skeleton; at the same time, it can effectively adjust the frontier orbital energy level of the organic compound and enhance the multiple resonance effect of the rigid conjugated plane of the boron-nitrogen ring structure, thereby achieving the effect of adjusting the luminescent color of the organic compound and narrowing the FHWM of the luminescence spectrum; in addition, compared with the traditional aromatic amine-type skeleton, the carbazole-type skeleton has stronger rigidity, which can effectively enhance the oscillator strength of the compound, and N and B are located in the para position of the conjugated six-membered ring and will not rotate freely, thereby improving the planarity of the boron-nitrogen-containing organic compound molecule, which is conducive to further narrowing the FWHM of the luminescence spectrum of the new organic compound.

[0064] Another type of compound is a boron-nitrogen ring structure modified by introducing carbazole and furan as modifying groups in the boron-nitrogen ring skeleton. Since furan has a poorer electron-donating ability than carbazole, it can reduce the electron cloud density around the B atom and improve the luminescence efficiency of the boron-nitrogen organic compound; it can also extend the conjugation length of the entire molecule and improve the stability of the compound.

[0065] The boron-nitrogen-containing organic compounds of the present invention can be used as functional materials in electronic devices, particularly light-emitting devices. These light-emitting devices can be selected from color converters, OLEDs, OLEECs, and organic light-emitting field-effect transistors; OLED devices are particularly preferred. Organic functional materials can be categorized as color conversion materials (CCMs), hole injection materials (HIMs), hole transport materials (HTMs), electron transport materials (ETMs), electron injection materials (EIMs), electron blocking materials (EBMs), hole blocking materials (HBMs), luminescent materials (Emitters), host materials (Hosts), and organic dyes. In a preferred embodiment, the boron-nitrogen-containing organic compounds of the present invention can be used as luminescent materials.

[0066] In a preferred embodiment, the light emitting device has a light emission wavelength of 300 nm-1500 nm, preferably 400 nm-1000 nm, and more preferably 400 nm-800 nm.

[0067] In a preferred embodiment, the boron and nitrogen-containing organic compound according to the present invention can be used as a fluorescent guest material (ie, a fluorescent light-emitting material).

[0068] As a fluorescent guest material, it must have an appropriate singlet energy level, i.e., S1. In certain embodiments, the boron-nitrogen-containing organic compound according to the present invention has S1 ≥ 2.1 eV, preferably ≥ 2.3 eV, more preferably ≥ 2.5 eV, even more preferably ≥ 2.7 eV, and most preferably ≥ 2.8 eV.

[0069] As a fluorescent guest material, it must have a high photoluminescence quantum efficiency (PLQY). In certain embodiments, the boron-nitrogen-containing organic compound according to the present invention has a PLQY of ≥40%, preferably ≥50%, more preferably ≥60%, and most preferably ≥70%.

[0070] In certain embodiments, the boron-nitrogen-containing organic compound according to the present invention has a resonance factor f1 ≥ 0.2, preferably ≥ 0.3, more preferably ≥ 0.4, and most preferably ≥ 0.5.

[0071] As an organic functional material, it is desirable to have good thermal stability. Generally, the boron-nitrogen-containing organic compound according to the present invention has a glass transition temperature (Tg) ≥ 100°C, preferably Tg ≥ 140°C, and more preferably Tg ≥ 180°C.

[0072] In certain preferred embodiments, the boron-nitrogen-containing organic compound according to the present invention has (HOMO-(HOMO-1)) ≥ 0.2 eV, preferably ≥ 0.3 eV, more preferably ≥ 0.4 eV, and most preferably ≥ 0.45 eV.

[0073] In other preferred embodiments, the boron-nitrogen-containing organic compound according to the present invention has ((LUMO+1)-LUMO) ≥ 0.15 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.30 eV, and most preferably ≥ 0.35 eV.

[0074] The present invention also provides a polymer, which comprises at least one first repeating unit, wherein the first repeating unit comprises at least one structure corresponding to the boron-nitrogen-containing organic compound described in the present invention.

[0075] In some embodiments, the polymer further comprises at least one second repeating unit that is different from the first repeating unit.

[0076] In certain embodiments, the polymer is a conjugated polymer; in some preferred embodiments, the conjugated polymer comprises a second repeating unit selected from one of the following repeating units:

[0077] wherein R' is independently selected from H, D, C1-C20 straight-chain alkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C3-C20 branched-chain alkyl, C3-C20 cyclic alkyl, C3-C20 branched-chain alkoxy, C3-C20 cyclic alkoxy, C3-C20 branched-chain thioalkoxy, C3-C20 cyclic thioalkoxy, silyl, C1-C20 keto, C2-C20 alkoxycarbonyl, C7-C20 aryloxy The present invention also includes a combination of one or more of a 1,2-dimethylamino group, ...

[0078] In other preferred embodiments, the polymer comprises a polymer backbone and side chains connected to the polymer backbone, wherein the side chains are derived from the boron-nitrogen-containing organic compound of the present invention. More preferably, the polymer is a non-conjugated polymer comprising a second repeating unit selected from one of the following repeating units:

[0079] wherein R″ is independently selected from H, D, C1-C20 straight-chain alkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C3-C20 branched-chain alkyl, C3-C20 cyclic alkyl, C3-C20 branched-chain alkoxy, C3-C20 cyclic alkoxy, C3-C20 branched-chain thioalkoxy, C3-C20 cyclic thioalkoxy, silyl, C1-C20 keto, C2-C20 alkoxycarbonyl, C7-C20 aryloxy a carbonyl group, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, I, a crosslinkable group, a substituted aryl group or an unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms;

[0080] In a preferred embodiment, the polymer is synthesized by a method selected from the group consisting of SUZUKI-, YAMAMOTO-, STILLE-, NIGESHI-, KUMADA-, HECK-, SONOGASHIRA-, HIYAMA-, FUKUYAMA-, HARTWIG-BUCHWALD- and ULLMAN.

[0081] In a preferred embodiment, the polymer according to the present invention has a glass transition temperature (Tg) ≥ 100°C, preferably ≥ 120°C, more preferably ≥ 140°C, even more preferably ≥ 160°C, and most preferably ≥ 180°C.

[0082] In a preferred embodiment, the molecular weight distribution (PDI) of the polymer according to the present invention is preferably in the range of 1 to 5, more preferably 1 to 4, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1 to 1.5.

[0083] In a preferred embodiment, the weight average molecular weight (Mw) of the polymer according to the present invention is preferably in the range of 10,000 to 1,000,000, more preferably 50,000 to 500,000, more preferably 100,000 to 400,000, even more preferably 150,000 to 300,000, and most preferably 200,000 to 250,000.

[0084] In certain embodiments, the boron-nitrogen-containing organic compound or polymer according to the present invention has a luminescent function, and the luminescent wavelength is between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm. The luminescence referred to herein refers to photoluminescence or electroluminescence.

[0085] The present invention also relates to a mixture comprising an organic compound or polymer containing boron and nitrogen as described above, and at least one organic functional material. The at least one organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminophore, and a host material. The luminophore is selected from a singlet luminophore (fluorescent luminophore), a triplet luminophore (phosphorescent luminophore), and an organic thermally excited delayed fluorescence material (TADF material). For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0086] In some preferred embodiments, the mixture comprises at least one boron-nitrogen-containing organic compound or polymer according to the present invention and a fluorescent host material. The boron-nitrogen-containing organic compound according to the present invention can serve as a fluorescent guest material, wherein the weight percentage of the fluorescent guest is ≤ 10 wt %, preferably ≤ 9 wt %, more preferably ≤ 8 wt %, particularly preferably ≤ 7 wt %, and most preferably ≤ 5 wt %.

[0087] Detailed descriptions of the host material, fluorescent light-emitting material, TADF material and other organic functional materials are given in WO2018095395. The entire contents of this patent document are hereby incorporated herein by reference.

[0088] One object of the present invention is to provide a material solution for vapor deposition type OLEDs.

[0089] In certain embodiments, the boron-nitrogen-containing organic compound according to the present invention has a molecular weight of ≤1200 g / mol, preferably ≤1100 g / mol, very preferably ≤1000 g / mol, more preferably ≤950 g / mol, and most preferably ≤900 g / mol.

[0090] Another object of the present invention is to provide a material solution for printed OLEDs.

[0091] In certain embodiments, the boron-nitrogen-containing organic compound according to the present invention has a molecular weight of ≥800 g / mol, preferably ≥1000 g / mol, preferably ≥1100 g / mol, and most preferably ≥1200 g / mol.

[0092] In other embodiments, the boron-nitrogen-containing organic compound according to the present invention has a solubility in toluene of ≥10 mg / mL at 25° C., preferably ≥15 mg / mL, and most preferably ≥20 mg / mL.

[0093] The present invention further relates to a composition or ink comprising at least one boron-nitrogen-containing organic compound or polymer according to the present invention and an organic solvent.

[0094] When used in printing processes, ink viscosity and surface tension are important parameters. The appropriate surface tension parameters of the ink are suitable for a specific substrate and a specific printing method.

[0095] In a preferred embodiment, the surface tension of the ink according to the present invention at operating temperature or at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; and most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0096] In another preferred embodiment, the viscosity of the ink according to the present invention at operating temperature or 25° C. is in the range of about 1 cps to 100 cps; more preferably, in the range of 1 cps to 50 cps; more preferably, in the range of 1.5 cps to 20 cps; and most preferably, in the range of 4.0 cps to 20 cps. Such a formulated composition will facilitate inkjet printing.

[0097] Viscosity can be adjusted by various methods, such as by selecting the appropriate solvent and adjusting the concentration of the functional material in the ink. The ink containing the metal organic complex or polymer according to the present invention facilitates adjustment of the printing ink within an appropriate range according to the printing method used. Generally, the weight ratio of the functional material contained in the composition according to the present invention is in the range of 0.3 wt% to 30 wt%, preferably in the range of 0.5 wt% to 20 wt%, more preferably in the range of 0.5 wt% to 15 wt%, even more preferably in the range of 0.5 wt% to 10 wt%, and most preferably in the range of 1 wt% to 5 wt%.

[0098] In some embodiments, according to the ink of the present invention, the organic solvent is selected from aromatic or heteroaromatic based solvents, in particular aliphatic chain / ring substituted aromatic solvents, or aromatic ketone solvents, or aromatic ether solvents.

[0099] Examples of solvents suitable for the present invention include, but are not limited to, aromatic or heteroaromatic based solvents: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, 1-methoxynaphthalene, cyclohexylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4 -(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.; ketone-based solvents: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, Ketones: isophorone, 2,6,8-trimethyl-4-nonanone, fenchone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, phorone, di-n-amyl ketone; aromatic ether solvents: 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylbenzene alkyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether; ester solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc.

[0100] Further, according to the ink of the present invention, the organic solvent can be selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0101] In some other embodiments, the printing ink further comprises another organic solvent. Examples of the other organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and / or mixtures thereof.

[0102] In a preferred embodiment, the composition according to the present invention is a solution.

[0103] In another preferred embodiment, the composition according to the present invention is a suspension.

[0104] The composition in the embodiment of the present invention may include 0.01wt% to 20wt% of the boron-nitrogen-containing organic compound or its mixture according to the present invention, preferably 0.1wt% to 15wt%, more preferably 0.2wt% to 10wt%, and most preferably 0.25wt% to 5wt% of the organic compound or its mixture.

[0105] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably a preparation method by printing or coating.

[0106] Suitable printing or coating techniques include, but are not limited to, inkjet printing, gravure printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roll printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush or pad printing, and slot die coating. Inkjet printing, nozzle printing, and gravure printing are preferred. The solution or suspension may further include one or more components, such as a surfactant, lubricant, wetting agent, dispersant, hydrophobic agent, adhesive, etc., to adjust viscosity, film-forming properties, and improve adhesion. For more information on printing techniques and their requirements for related solutions, such as solvent, concentration, and viscosity, please refer to "Handbook of Print Media: Technologies and Production Methods," edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0107] The present invention also provides an application of the boron-nitrogen-containing organic compound or polymer described above, i.e., applying the boron-nitrogen-containing organic compound or polymer to an organic electronic device. The organic electronic device may be selected from, but not limited to, color converters, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEDs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPEDs). Organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors (OLEDs), are particularly preferred. In embodiments of the present invention, the organic compound is preferably used in the light-emitting layer of an electroluminescent device.

[0108] The present invention further relates to an organic electronic device comprising at least one boron-nitrogen-containing organic compound, polymer, or mixture as described above. Generally, such an organic electronic device comprises at least a cathode, an anode, and a functional layer located between the cathode and the anode, wherein the functional layer comprises at least one boron-nitrogen-containing organic compound, polymer, or mixture as described above. The organic electronic device may be selected from, but is not limited to, color converters, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEDs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Particularly preferred are organic electroluminescent devices, such as OLEDs, OLEECs, and OLEDs.

[0109] In some particularly preferred embodiments, the organic electronic device comprises a light-emitting layer, which comprises an organic compound containing boron and nitrogen, or an organic compound containing boron and nitrogen and a host material, or an organic compound containing boron and nitrogen, a phosphorescent light-emitting body and a host material.

[0110] In some particularly preferred embodiments, the organic electronic device is an organic light-emitting device, which comprises a light-emitting layer, wherein the guest material of the light-emitting layer comprises at least one boron-nitrogen-containing organic compound, polymer or mixture as described above.

[0111] The electroluminescent device described above, in particular the OLED, comprises a substrate, an anode, at least one light-emitting layer, and a cathode.

[0112] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best if the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from a polymer film or plastic with a glass transition temperature (Tg) of above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates are polyethylene terephthalate (PET) and polyethylene (2,6-naphthalene) (PEN).

[0113] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0114] The cathode can comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In a preferred embodiment, the absolute difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes in OLEDs are possible cathode materials for the devices of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0115] OLEDs may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Suitable materials for these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated by reference.

[0116] In a preferred embodiment, in the light-emitting device according to the present invention, the light-emitting layer thereof is prepared by the composition according to the present invention.

[0117] The light emitting device according to the present invention, in particular the OLED, has a light emission wavelength between 300 nm and 1500 nm, preferably between 350 nm and 1200 nm, and more preferably between 400 nm and 800 nm.

[0118] The present invention also relates to applications of the organic electronic device according to the present invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0119] The present invention also relates to electronic devices incorporating organic electronic devices according to the present invention, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like. In certain embodiments, the electronic device comprises a housing and the aforementioned device disposed on the housing. The electronic device can be any terminal device equipped with an OLED display screen, including, but not limited to, smartphones, tablet computers, personal laptop computers, smart televisions, in-car displays, smart watches, and the like. In some embodiments, the electronic device is a smartphone.

[0120] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0121] Specific embodiments

[0122] 1. Synthesis of compounds

[0123] Synthesis of intermediate 1b:

[0124] 1a (100 g), 4-tert-butylaniline (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 126 g of intermediate 1b in a 77% yield. Product characterization: MS (ASAP) = 337.5.

[0125] Synthesis of intermediate 1h:

[0126] Intermediate 1b (100 g), m-fluorobromobenzene (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 167 g of intermediate 1h in a 91% yield. Product characterization: MS (ASAP) = 431.6.

[0127] Synthesis of intermediate 1f:

[0128] Under nitrogen, a three-necked flask was charged with 1c (100g), 1d (100g), potassium carbonate (25g), 3g of tetrakistriphenylphosphine palladium, and 1000mL of toluene / 50mL of ethanol / 50mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 hours. The temperature was then lowered. The reaction was extracted with ethyl acetate and deionized water, and the organic phase was washed twice with water, dried, filtered, and the filtrate was evaporated to dryness to obtain 124g of crude intermediate 1e. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 123.2g of intermediate 1e, with a yield of 81%.

[0129] Under nitrogen, a three-necked flask was charged with intermediate 1e (100 g), triethyl phosphite (50 g), and DMF (1000 mL). The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 hours. The reaction was then cooled. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 80 g of crude intermediate 1f. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 75 g of intermediate 1f. Product characterization: MS (ASAP) = 335.2.

[0130] Synthesis of intermediate 2c:

[0131] Under nitrogen, a three-necked flask was charged with 2a (100 g), 1d (100 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (3 g), and 1000 mL of toluene / 50 mL of ethanol / 50 mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was stopped by heating under reflux for 12 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice with water, dried, filtered, and the filtrate was evaporated to dryness to obtain 124 g of crude intermediate 2b. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 114.2 g of intermediate 2b, with a yield of 75%.

[0132] Under nitrogen, intermediate 2b (100 g), triethyl phosphite (50 g), and DMF (1000 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 75 g of crude intermediate 2c. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 72 g of intermediate 2c. Product characterization: MS (ASAP) = 410.3.

[0133] Synthesis of intermediate 3c:

[0134] Under nitrogen, a three-necked flask was charged with 3a (100 g), deuterated phenylboronic acid (100 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (3 g), and 1000 mL of toluene / 50 mL of ethanol / 50 mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 hours. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 180 g of crude intermediate 3b. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 175 g of intermediate 3b. The yield was 95%.

[0135] Intermediate 3b (100 g), intermediate 1b (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 105 g of intermediate 3c in a 78% yield. Product characterization: MS (ASAP) = 573.6.

[0136] Synthesis of intermediate 4c:

[0137] 1a (100 g), intermediate 4b (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 167 g of intermediate 4c in a 91% yield. Product characterization: MS (ASAP) = 391.6.

[0138] Synthesis of intermediate 4d:

[0139] Under nitrogen, a three-necked flask was charged with 4a (100 g), carbazole (100 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (3 g), and 1000 mL of toluene / 50 mL of ethanol / 50 mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 hours. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 150 g of crude intermediate 4b. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 142 g of intermediate 4b, with a yield of 71%.

[0140] Intermediate 4b (100 g), intermediate 4c (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 152 g of intermediate 4d in an 85% yield. Product characterization: MS (ASAP) = 650.9.

[0141] Synthesis of intermediate 5b:

[0142] 1a (100 g), 5a (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 131 g of intermediate 5b in a 78% yield. Product characterization: MS (ASAP) = 371.5.

[0143] Synthesis of intermediate 5c:

[0144] Intermediate 5b (100 g), m-fluorobromobenzene (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 82 g of intermediate 5c in a 70% yield. Product characterization: MS (ASAP) = 465.6.

[0145] Synthesis of intermediate 9d:

[0146] 9a (2-aminodibenzofuran) (100 g), 9b (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. The reaction solution was cooled to room temperature, extracted with a large amount of deionized water and dichloromethane, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 82 g of intermediate 9c in a 71% yield. Product characterization: MS (ASAP) = 417.

[0147] Intermediate 9c (7.5 g, 20 mmol), sodium tert-butoxide (17.68 g, 184 mmol), palladium acetate (0.2 g, 1.0 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.53 g, 1.8 mmol) were dissolved in dioxane (200 mL), heated to 110°C under nitrogen, and stirred for 18 hours. The reaction solution was cooled to room temperature, quenched with hydrochloric acid (2 M, 20 mL), and then extracted with dichloromethane, retaining the organic phase. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 1.4 g of intermediate 9d in a 20% yield. Product characterization: MS (ASAP) = 335.2.

[0148] Synthesis of intermediate 10d:

[0149] The synthesis of intermediate 10d was similar to that of intermediate 9d. 10a (100 g), 10b (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 85 g of intermediate 10c in 80% yield. Product characterization: MS (ASAP) = 417.

[0150] Intermediate 10c (7.5 g, 20 mmol), sodium tert-butoxide (17.68 g, 184 mmol), palladium acetate (0.2 g, 1.0 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.53 g, 1.8 mmol) were dissolved in dioxane (200 mL), heated to 110°C under nitrogen, and stirred for 18 hours. The reaction solution was cooled to room temperature and quenched with hydrochloric acid (2 M, 20 mL). The mixture was then extracted with dichloromethane, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 1.6 g of intermediate 10d in a 20% yield. Product characterization: MS (ASAP) = 335.2.

[0151] Synthesis of intermediate 11d:

[0152] Under nitrogen, a three-necked flask was charged with 11a (100g), 11b (100g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (3g), and 1000mL of toluene / 50mL of ethanol / 50mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 hours. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice with water, dried, filtered, and the filtrate was evaporated to dryness to obtain 100g of crude intermediate 11c. The product was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to obtain 94.2g of intermediate 11c, with a yield of 70%.

[0153] Under nitrogen, intermediate 11c (100 g), triethyl phosphite (50 g), and DMF (1000 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 hours. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 75 g of crude intermediate 11d. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 70 g of intermediate 11d in a 65% yield. Product characterization: MS (ASAP) = 335.2.

[0154] Synthesis of intermediate 12d:

[0155] Under nitrogen, a three-necked flask was charged with 12a (100 g), 12b (100 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (3 g), and 1000 mL of toluene / 50 mL of ethanol / 50 mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 105 g of crude intermediate 12c. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 95.2 g of intermediate 12c, with a yield of 71%.

[0156] Under nitrogen, intermediate 12c (100 g), triethyl phosphite (50 g), and DMF (1000 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 75 g of crude intermediate 12d. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 78 g of intermediate 12d in a 67% yield. Product characterization: MS (ASAP) = 255.

[0157] Synthesis of intermediate 13b:

[0158] Under nitrogen, 13a (100 g) and dichloromethane (100 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and 1 eq of NBS was slowly added. After reacting for 2 hours, the mixture was extracted with water. The organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 15 g of crude intermediate 13b. Column chromatography (petroleum ether / ethyl acetate 15:1) afforded 10 g of intermediate 13b in a 10% yield. Product characterization: MS (ASAP) = 335.2.

[0159] Synthesis of intermediate 14c:

[0160] Under nitrogen, a three-necked flask was charged with 14a (100g), 11b (100g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (3g), and 1000mL of toluene / 50mL of ethanol / 50mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 hours. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice with water, dried, filtered, and the filtrate was evaporated to dryness to obtain 115g of crude product 14b. The product was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to yield 99.5g, an 80% yield.

[0161] Under nitrogen, 14b (100 g), triethyl phosphite (50 g), and DMF (1000 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 73 g of crude intermediate 14c. Column chromatography (petroleum ether / ethyl acetate 15:1) afforded 69 g of intermediate 14c in a 66% yield. Product characterization: MS (ASAP) = 335.2.

[0162] Synthesis of intermediate 15c:

[0163] The synthesis of intermediate 15c was similar to that of intermediate 9d. 15a (100 g), 10b (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 83 g of intermediate 15b in 80% yield. Product characterization: MS (ASAP) = 416.09.

[0164] Intermediate 15b (7.5 g, 20 mmol), sodium tert-butoxide (17.68 g, 184 mmol), palladium acetate (0.2 g, 1.0 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.53 g, 1.8 mmol) were dissolved in dioxane (200 mL), heated to 110°C under nitrogen, and stirred for 18 hours. The reaction solution was cooled to room temperature and quenched with hydrochloric acid (2 M, 20 mL). The mixture was then extracted with dichloromethane, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 1.3 g of intermediate 15c in an 18% yield. Product characterization: MS (ASAP) = 335.2.

[0165] Synthesis of intermediate 16d:

[0166] Under nitrogen, a three-necked flask was charged with 16a (synthesis method reference: CN107922837A) (100g), 16b (100g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (3g), and 1000mL toluene / 50mL ethanol / 50mL water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, the reaction was stopped by heating under reflux for 12 hours, and the temperature was cooled. The organic phase was extracted with ethyl acetate and deionized water, washed twice, dried, filtered, and the filtrate was spin-dried to obtain 106g of crude product 16c. The product was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to obtain 93.5g of the product, with a yield of 70%.

[0167] Under nitrogen, a three-necked flask was charged with 16c (100 g), triethyl phosphite (50 g), and DMF (1000 mL). The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, the reaction was stopped by heating under reflux for 24 h, and the temperature was cooled. The organic phase was extracted with ethyl acetate and deionized water, washed twice, dried, filtered, and the filtrate was spin-dried to obtain 72 g of crude intermediate 16d. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 64 g of intermediate 16d in a 65% yield. Product characterization: MS (ASAP) = 335.2.

[0168] Synthesis of intermediate 17c:

[0169] Under nitrogen, a three-necked flask was charged with 17a (synthesis method reference: CN107922837A) (100g), 16b (100g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (3g), and 1000mL toluene / 50mL ethanol / 50mL water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, the reaction was stopped by heating under reflux for 12 hours, and the temperature was cooled. The organic phase was extracted with ethyl acetate and deionized water, washed twice, dried, filtered, and the filtrate was spin-dried to obtain 109g of crude product 17b. The product was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to obtain 94.5g of the product, with a yield of 70%.

[0170] Under nitrogen, 17b (100 g), triethyl phosphite (50 g), and DMF (1000 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was evaporated to dryness to obtain 74 g of crude intermediate 17c. Column chromatography (petroleum ether / ethyl acetate 15:1) afforded 66 g of intermediate 17c in a 65% yield. Product characterization: MS (ASAP) = 335.2.

[0171] Synthesis of intermediate 18c:

[0172] Under nitrogen, a three-necked flask was charged with 18a (100g), 11b (100g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (3g), and 1000mL of toluene / 50mL of ethanol / 50mL of water. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, and the reaction was terminated by heating under reflux for 12 hours. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice with water, dried, filtered, and the filtrate was evaporated to dryness to obtain 101g of crude product 18b. The product was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to yield 90.5g, a yield of 68%.

[0173] Under nitrogen, 18b (100 g), triethyl phosphite (50 g), and DMF (1000 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 150°C, and the reaction was terminated by heating under reflux for 24 h. The temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 70 g of crude intermediate 18c. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 67 g of intermediate 18c in a 65% yield. Product characterization: MS (ASAP) = 335.2.

[0174] Synthesis of compound 1:

[0175] Intermediate 1h (50 g), intermediate 1f (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 105 g of intermediate 1j in a 92% yield.

[0176] Intermediate 1j (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 3.3 g of compound 1 in a 34% yield. Product characterization: MS (ASAP) = 676.7.

[0177] Synthesis of compound 2:

[0178] Intermediate 1h (50 g), intermediate 2c (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 112 g of intermediate 2d in a 95% yield.

[0179] Intermediate 2d (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 3.9 g of compound 2 in a 41% yield. Product characterization: MS (ASAP) = 751.8.

[0180] Synthesis of compound 3:

[0181] Intermediate 1f (50 g), intermediate 3c (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 101 g of intermediate 3d in a 95% yield.

[0182] Intermediate 3d (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.1 g of compound 3 in a 24% yield. Product characterization: MS (ASAP) = 757.81.

[0183] Synthesis of compound 4:

[0184] Intermediate 4d (50 g), intermediate 1f (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 43 g of intermediate 4e in a 53% yield.

[0185] Intermediate 4e (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.6 g of compound 4 in a 30% yield. Product characterization: MS (ASAP) = 895.9.

[0186] Synthesis of compound 5:

[0187] Intermediate 5c (50 g), intermediate 2c (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 52 g of intermediate 5d in a 64% yield.

[0188] Intermediate 5d (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.5 g of compound 5 in a 30% yield. Product characterization: MS (ASAP) = 785.7.

[0189] Synthesis of compound 6:

[0190] Intermediate 5c (50 g), intermediate 1f (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 54 g of intermediate 6a in a 65% yield.

[0191] Intermediate 6a (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.4 g of compound 6 in a 30% yield. Product characterization: MS (ASAP) = 710.6.

[0192] Synthesis of compound 7:

[0193] Intermediate 3c (50 g), intermediate 2c (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 59 g of intermediate 7a in a 67% yield.

[0194] Intermediate 7a (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.5 g of compound 7 in a 30% yield. Product characterization: MS (ASAP) = 832.9.

[0195] Synthesis of compound 8:

[0196] Intermediate 1h (50 g), 8a (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 54 g of intermediate 8b in a 65% yield.

[0197] Intermediate 8b (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.4 g of compound 8 in a 30% yield. Product characterization: MS (ASAP) = 676.7.

[0198] Synthesis of compound 9:

[0199] The synthesis process is similar to that of compound 1 (9d replaces 1f, 9-1 replaces 1j, i.e., the intermediate 9-1 is first formed under the action of a base), then under the action of n-butyllithium, the Li salt is formed, and then under the action of BBr3, the final product compound 9 is formed with a yield of 8% and MS (ASAP) = 676.7.

[0200] Synthesis of compound 10:

[0201] The synthesis process is similar to that of compound 1 (10d replaces 1f, 10-1 replaces 1j, i.e., the intermediate 10-1 is first formed under the action of a base, then under the action of n-butyllithium, a Li salt is formed, and then under the action of BBr3, the final product compound 10 is formed with a yield of 6% and MS (ASAP) = 676.7.

[0202] Synthesis of compound 11:

[0203] The synthesis process is similar to that of compound 1 (11d replaces 1f, 11-1 replaces 1j, i.e., the intermediate 11-1 is first formed under the action of a base, and then the Li salt is formed under the action of n-butyl lithium, and then the final product compound 11 is formed under the action of BBr3, with a yield of 10% and MS (ASAP) = 676.7.

[0204] Synthesis of compound 12:

[0205] The synthesis process is similar to that of compound 1 (12d replaces 1f, 12-1 replaces 1j, i.e., the intermediate 12-1 is first formed under the action of a base, then under the action of n-butyllithium, the Li salt is formed, and then under the action of BBr3, the final product compound 12 is formed with a yield of 20% and MS (ASAP) = 676.7.

[0206] Synthesis of compound 13:

[0207] The synthesis process is similar to that of compound 1 (13b replaces 1f, 13-1 replaces 1j, i.e., the intermediate 13-1 is first formed under the action of a base, then under the action of n-butyllithium, the Li salt is formed, and then under the action of BBr3, the final product compound 13 is formed with a yield of 8% and MS (ASAP) = 676.7.

[0208] Synthesis of compound 14:

[0209] The synthesis process was similar to that of compound 1 (14c replaced 1f, 14-1 replaced 1j, i.e., the intermediate 14-1 was first formed under the action of a base, then under the action of n-butyllithium to form a Li salt, and then under the action of BBr3 to form the final product compound 14, with a yield of 5% and MS (ASAP) = 676.7.

[0210] Synthesis of compound 15:

[0211] The synthesis process was similar to that of compound 5 (15c replaced 2c, 15-1 replaced 5d, i.e., the intermediate 15-1 was first formed under the action of a base, then under the action of n-butyllithium to form a Li salt, and then under the action of BBr3 to form the final product compound 15, with a yield of 7% and MS (ASAP) = 710.6.

[0212] Synthesis of compound 16:

[0213] 16e (100 g), m-fluoroiodobenzene (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 116 g of intermediate 16f in an 89% yield.

[0214] Intermediate 16f (100 g), 16h (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 98 g of intermediate 16i in an 85% yield.

[0215] Intermediate 16i (100 g), 1a (100 g), tris(dibenzylideneacetone)dipalladium (16 g), and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL), heated to 90°C, and stirred for 2 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 96 g of intermediate 16j in an 80% yield.

[0216] Intermediate 16j (50 g), 16d (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 55 g of intermediate 16k in a 67% yield.

[0217] Intermediate 16k (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 2.5 g of compound 16 in a 6% yield. Product characterization: MS (ASAP) = 865.

[0218] Synthesis of compound 17:

[0219] The synthesis process was similar to that of compound 1 (17c replaced 1f, 17-1 replaced 1j, i.e., the intermediate 17-1 was first formed under the action of a base, then under the action of n-butyllithium to form a Li salt, and then under the action of BBr3 to form the final product compound 17, with a yield of 4% and MS (ASAP) = 692.75.

[0220] Synthesis of compound 18:

[0221] The synthesis process was similar to that of compound 1 (18c replaced 1f, 18-1 replaced 1j, i.e., the intermediate 18-1 was first formed under the action of a base), then under the action of n-butyllithium, a Li salt was formed, and then under the action of BBr3, the final product compound 18 was formed with a yield of 8% and MS (ASAP) = 710.6.

[0222] Comparative compound 1 (DB1)

[0223] The existing boron-nitrogen material structure is as follows:

[0224] The specific synthesis method of the existing boron-nitrogen material can adopt the existing synthesis method, and the present invention will not go into details.

[0225] Comparative compound 2 (DB2)

[0226] The existing boron nitrogen structure is as follows:

[0227] Synthesis of comparative compound 2:

[0228] Under nitrogen, add d1 (100g), d2 (100g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (3g), and 1000mL toluene / 50mL ethanol / 50mL water to a three-necked flask. Replace the atmosphere with nitrogen three times, heat to 100°C, reflux for 12 hours to terminate the reaction, and cool. Extract with ethyl acetate and deionized water, wash the organic phase twice, dry, filter, and spin-dry the filtrate to obtain 80g of crude product d3. Separate by column chromatography (petroleum ether / ethyl acetate 15:1) to collect 75g of the product. Yield: 38%.

[0229] The synthesis reference of compound d4, “Synthesis of Dibenzofurans via Palladium-Catalyzed Phenol-Directed CH Activation / CO Cyclization”, is not described here in detail.

[0230] Under nitrogen, compound d4 (100 g) and dichloromethane (100 mL) were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and 1 eq of NBS was slowly added. After reacting for 2 hours, the mixture was extracted with water. The organic phase was washed twice with water, dried, filtered, and the filtrate was spin-dried to yield 80 g of crude product d5. Product d5 was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to yield 10 g. Yield: 10%. Product characterization: MS (ASAP) = 335.2.

[0231] Intermediate 1h (50 g), d5 (110 g), and anhydrous cesium carbonate (285 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL), heated to 100°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 51 g of intermediate d6 in a 63% yield.

[0232] Intermediate d6 (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyllithium (16 mL, 1.3 M solution in n-hexane) was added dropwise under an ice bath. After the addition was complete, the reaction solution was heated to 100°C and stirred for 2 hours. Subsequently, the reaction solution was cooled to an ice bath, and boron tribromide (5.2 mL) was added dropwise. After the addition was complete, the solution was heated to 180°C and stirred for 8 hours. Subsequently, N,N-diisopropylethylamine (24 mL) was added dropwise under an ice bath. After the addition was complete, the solution was heated to 180°C and stirred overnight. After the reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic solvent was removed by vacuum distillation, and the product was purified by silica gel column chromatography to obtain 1.2 g of compound DB2 in a 12% yield. Product characterization: MS (ASAP) = 676.7.

[0233] 2. Energy level structure of the compound

[0234] The energy levels of organic compounds can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian09W (Gaussian Inc.). For detailed simulation methods, see WO2011141110. The molecular geometry is first optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is then calculated using TD-DFT (time-dependent density functional theory) using the "TD-SCF / DFT / Default Spin / B3PW91" basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated using the following calibration formulas, with S1, T1, and the resonance factor f(S1) used directly. HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206 LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0235] The HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1:

[0236] Table 1

[0237] 3. Optical properties of compounds

[0238] The optical properties of compounds 1-18, DB1, and DB2 in the synthesis examples are shown in Table 2.

[0239] Table 2

[0240] Note: The wavelength range of 407nm to 505nm is the blue light region, and the wavelength range of 505nm to 525nm is the green light region.

[0241] As shown in Table 2, compounds 2, 5, and 7 synthesized in this invention employ an indolecarbazole group as a modifying group attached to the B atom, effectively suppressing the rotation and vibration of the internal free radicals, thereby narrowing the FHWM of the emission spectrum and improving quantum efficiency, achieving efficient, narrow FHMW blue light emission. Compound 7 employs a deuterated benzene ring as a modifying group to modify the benzene ring para to the B atom, enhancing the electron cloud density of the benzene ring para to the B atom, thereby modulating the light color.

[0242] Compounds 1, 3, 4, 6, 8-18 utilize a carbazole-furan group as a modifying group attached to the B atom within the boron-nitrogen ring structure. Due to the electron-withdrawing effect of the oxygen atom, this can reduce the electron cloud density of the benzene ring adjacent to the B atom, enhancing the superresonance effect of the overall compound. This effectively narrows the Full Width Half Mean (FWHM) of the luminescence spectrum of the novel organic compound and also slightly blue-shifts the emission of the novel BN organic compound. Compound 17 utilizes a carbazole-thiophene group as a modifying group attached to the B atom within the boron-nitrogen ring structure, achieving similar effects as the carbazole-furan group.

[0243] The luminescence spectrum of the comparative example compound 2 shows green light emission, which indicates that the position of the fused ring has a great influence on the maximum emission peak of the molecule.

[0244] 4. Preparation and Characterization of OLED Devices

[0245] Example 1 (Preparation of OLED Device 1)

[0246] Step S1: Use transparent glass as a substrate, clean the anode (ITO (15nm) / Ag (150nm) / ITO (15nm)) on it, and use stripping liquid, pure water, and isopropyl alcohol ultrasonic cleaning respectively, and then dry it and then treat it with Ar2 ozone.

[0247] Step S2: The cleaned substrate is moved into a vacuum vapor deposition device and placed in a high vacuum (1×10 -6 mbar), the ratio of PD to HT-1 was controlled to be 3:100, and a 10 nm hole injection layer (HIL) was formed.

[0248] Step S3: On the hole injection layer, 125 nm of hole transport layer material HT-1 is evaporated by vacuum evaporation.

[0249] Step S4: On the hole injection layer, 10 nm of electron blocking layer material HT-2 is deposited by vacuum evaporation.

[0250] Step S5: On the electron blocking layer, a light-emitting layer is deposited by vacuum evaporation, wherein the host material is BH and the guest material is the compound 1 of the present invention, with a mass ratio of 98:2 and a thickness of 25 nm.

[0251] Step S6: depositing 2 nm of hole blocking layer material ET-1 on the light-emitting layer by vacuum evaporation.

[0252] Step S7: On the hole blocking layer, ET-2 and Liq are vacuum evaporated as an electron transport layer with a mass ratio of 50:50 and a thickness of 35 nm.

[0253] Step S8: 1.5 nm of Yb is evaporated on the electron transport layer by vacuum evaporation as an electron injection layer.

[0254] Step S9: 17 nm of Mg:Ag (1:9) alloy was evaporated on the electron injection layer as a cathode.

[0255] Step S10: evaporating 55 nm of CPL material on the cathode layer.

[0256] The following are the structural formulas of the materials used in each functional layer:

[0257] Example 2 (Preparation of OLED Device 2)

[0258] Example 2 differs from Example 1 in that, in step S3, a 120 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and in step S5, the aforementioned compound 2 is used as the guest material. The remaining steps are identical to those in Example 1; please refer to Example 1 for details.

[0259] Example 3 (Preparation of OLED Device 3)

[0260] Example 3 differs from Example 1 in that, in step S3, a 122 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and the aforementioned compound 3 is used as the guest material in step S5. The remaining steps are the same as in Example 1. For details, please refer to Example 1.

[0261] Example 4 (Preparation of OLED Device 4)

[0262] Example 4 differs from Example 1 in that, in step S3, a 122 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and in step S5, the guest material is the aforementioned compound 8. The remaining steps are the same as in Example 1; please refer to Example 1 for details.

[0263] Example 5 (Preparation of OLED Device 5)

[0264] Example 5 differs from Example 1 in that, in step S3, a 122 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and the guest material in step S5 is compound 13. The remaining steps are the same as in Example 1; please refer to Example 1 for details.

[0265] Example 6 (Preparation of OLED Device 6)

[0266] Example 6 differs from Example 1 in that, in step S3, a 122 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and the aforementioned compound 14 is used as the guest material in step S5. The remaining steps are the same as in Example 1. For details, please refer to Example 1.

[0267] Example 7 (Preparation of OLED Device 7)

[0268] Example 7 differs from Example 1 in that, in step S3, a 122 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and the aforementioned compound 16 is used as the guest material in step S5. The remaining steps are the same as in Example 1. For details, please refer to Example 1.

[0269] Comparative Example 1 (Preparation of OLED Comparative Device 1)

[0270] Comparative Example 1 differs from Example 1 in that, in step S3, a 121 nm thick layer of hole transport layer material HT-1 is vacuum-deposited on the hole injection layer, and in step S5, the guest material is the existing boron-nitrogen material corresponding to Comparative Compound 1. The remaining steps are identical to those in Example 1; please refer to Example 1 for details.

[0271] The performance of the devices prepared in Examples 1 to 7 and Comparative Example 1 is shown in Table 3. The current efficiency and LT95 are based on Comparative Example 1.

[0272] Table 3

[0273] Note: LT95@1000nit: The working time when the device experiences 5% brightness loss at 1000 nits brightness.

[0274] From the current efficiency, luminescence spectrum FWHM and device operating life at 1000 brightness (operating time when 5% maximum brightness loss occurs) of the devices of Examples 1 to 7 and Comparative Example 1 in Table 3, it can be seen that compared with Comparative Example 1, the OLED devices of Examples 1 to 7 using the boron and nitrogen-containing organic compounds synthesized by the present invention exhibit higher luminescence efficiency, longer operating life and higher device stability.

[0275] It should be noted that the above are only specific embodiments of the present invention, but the scope of protection of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by a person skilled in the art within the technical scope disclosed in the present invention should be included in the scope of protection of the present invention. The embodiments of the present invention and the features within the embodiments can be combined with each other unless there is a conflict. Therefore, the scope of protection of the present invention shall be based on the scope of protection of the claims.

Claims

1. A boron-nitrogen-containing organic compound, characterized in that The structure of the boron-nitrogen-containing organic compound is represented by a combination of chemical formula (I-1) and chemical formula (I-2): in: * represents the connection point where chemical formula (I-1) and chemical formula (I-2) are fused; Q1 ring, Q2 ring, and Q3 ring are independently selected from substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, or substituted or unsubstituted fused ring structures; X1 and X2 are independently selected from B, N, P, P=O or Al; Y1 and Y2 are independently selected from C=O, N-R1, O, S, Se, P, P=O or P=S; Y3 is selected from C=O, N-R1, O, Se, P, P=O or P=S; Each occurrence of V0 is independently selected from C-R2 or N-R3; R1-R3 are, at each occurrence, identically or differently selected from H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

2. The boron-nitrogen-containing organic compound according to claim 1, characterized in that The structure of the boron-nitrogen-containing organic compound is represented by a combination of Chemical Formula (I-1a) and Chemical Formula (I-2a): Wherein, V0, Y1, Y2, Y3, Q1 ring, Q2 ring, Q3 ring, and * are defined the same as in claim 1.

3. The boron-nitrogen-containing organic compound according to claim 1 or 2, characterized in that The boron-nitrogen-containing organic compound has a structure as shown in one of formulas (II-1) to (II-10): Wherein, the definitions of V0, Y1, Y2, Y3, Q1 ring, and Q3 ring are the same as those in claim 1, and the definition of V1 is the same as that of V0.

4. The boron-nitrogen-containing organic compound according to any one of claims 1 to 3, characterized in that The Q1 ring, the Q2 ring, and the Q3 ring, when each ring appears, are independently selected from one or more combinations of the following structures: wherein each occurrence of V is independently selected from C-R4 or N-R5; Each occurrence of W is independently selected from B-R6, C(=O), N-R7, O, S, P, P=O or P=S; R4-R7, at each occurrence, are selected, identically or differently, from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, where one or more of the groups can form a ring system with each other and / or the group to which they are bound.

5. A polymer comprising at least one first repeating unit, characterized in that The first repeating unit comprises at least one structure corresponding to the boron-nitrogen-containing organic compound according to any one of claims 1 to 4.

6. A composition, characterized in that The method comprises an organic solvent, and at least one boron-nitrogen-containing organic compound according to any one of claims 1 to 4 or at least one polymer according to claim 5.

7. A mixture, characterized in that The method comprises a boron-nitrogen-containing organic compound as described in any one of claims 1 to 4 or a polymer as described in claim 5, and at least one organic functional material, wherein the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminophore and a host material.

8. An organic electronic device comprising a boron-nitrogen-containing organic compound according to any one of claims 1 to 4, a polymer according to claim 5, or a mixture according to claim 7.

9. The organic electronic device according to claim 8, characterized in that The organic electronic device is selected from color converters, organic light emitting diodes, organic photovoltaic cells, organic light emitting cells, organic field effect transistors, organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors or organic plasmon emission diodes.

10. The organic electronic device according to claim 8, characterized in that The organic electronic device is an organic light-emitting device, which comprises a light-emitting layer. The guest material of the light-emitting layer comprises at least one boron-nitrogen-containing organic compound according to any one of claims 1 to 4, or a polymer according to claim 5, or a mixture according to claim 7.

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