Boron-nitrogen-containing organic compound and use thereof in organic electronic device

Abstract

Provided in the present invention are a boron-nitrogen-containing organic compound and the use thereof in an organic electronic device. The boron-nitrogen-containing organic compound has a structure as represented by general formula (I) or general formula (II). The boron-nitrogen-containing organic compound is applied to an organic electronic device; and a device using the boron-nitrogen-containing organic compound has high luminous efficacy, a narrow FWHM as shown in its luminescence spectrum, a relatively long service life, etc.

Description

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

[0001] The present invention 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 containing the same, and applications thereof in organic electronic devices, in particular in organic electroluminescent devices. Background Art

[0002] Organic light-emitting diodes (OLEDs) have great application potential in the display field due to their excellent optoelectronic properties, such as fast response, high contrast, low production cost, and diversity in chemical synthesis.

[0003] Traditional OLED materials: The full width at half maximum (FWHM) of the emission spectrum of fluorescent materials is approximately 40nm to 60nm, the FWHM of phosphorescent materials is approximately 60nm to 90nm, and the FWHM of thermally activated delayed fluorescence (TADF) materials is approximately 70nm to 100nm. Therefore, traditional OLED materials have a large FWHM and exhibit low color purity, which does not meet the newly proposed BT.2020 standard. To improve color purity, it is necessary to use optical filters in the display to remove unwanted colors from the self-luminous spectrum, significantly reducing the luminous efficiency.

[0004] In 2016, boron-nitrogen TADF compounds (DOI: 10.1002 / adma.201505491) exhibiting the multiple resonance (MR) effect garnered widespread attention. These molecules not only efficiently emit light through reverse intersystem crossing (RISC) but also exhibit a narrow full width at half maximum (FWHM). They are currently one of the hottest topics in the field of OLED luminescent materials (ad refers to a common blue-emitting boron-nitrogen compound).

[0005] However, current blue-light-emitting boron-nitrogen materials still suffer from shortcomings such as poor lifetime, low efficiency, and insufficient stability. This present invention improves upon existing technologies by, on the one hand, introducing conjugated substituents outside the thiophene, furan, and fluorene rings to increase their stability, and, on the other hand, by introducing O and S heteroatoms into the indole fused ring to improve the PLQY of the boron-nitrogen materials. Experimental results demonstrate that this approach can enhance the overall device performance of boron-nitrogen blue-light-emitting materials. Summary of the Invention

[0006] 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, a polymer, a mixture, a composition, an organic electronic device and applications thereof, aiming to solve the problems of efficiency and life span of existing OLEDs.

[0007] The technical solutions of the present invention are as follows:

[0008] A boron-nitrogen-containing organic compound having a structure as shown in chemical formula (I) or chemical formula (II):

[0009] wherein: Ring A and Ring B are independently selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted fused ring structure; Y is independently selected from C-R1 or N, the same or different; V1 is independently selected from C-R2 or N, the same or different; Q and Z are selected from S, O or C-R3R4; R1-R4 are each independently selected from H or 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 a 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 or 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, and one or more of R1 to R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

[0010] 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.

[0011] The present invention also relates to a composition comprising at least one organic solvent and at least one boron-nitrogen-containing organic compound as described above or at least one polymer as described above.

[0012] 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 can be 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.

[0013] 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.

[0014] Beneficial Effects: The present invention, by applying the boron-nitrogen-containing organic compound to an organic light-emitting device, can enable the organic light-emitting device to have high luminous efficiency, high color purity, high device stability, and a long device operating life. According to the boron-nitrogen-containing organic compound of the present invention, on the one hand, the optical properties of the boron-nitrogen compound are improved by introducing the rigid structure of indolothiophene and indolofuran, and on the other hand, the optical properties of the boron-nitrogen skeleton are improved by introducing a conjugated group as a modifying group in the thiophene and furan structures adjacent to the boron atom. By introducing the conjugated group, i.e., the B ring, the conjugation length of the entire boron-nitrogen molecule can be extended, significantly improving the stability of the overall molecular structure and increasing the device life. In addition, by adjusting the introduced conjugated group and the A ring, the electron cloud density around the adjacent B atoms can be adjusted, facilitating the adjustment of the molecule's luminescence spectrum; at the same time, by adjusting the substituents on the A ring and the B ring, the planar stacking effect of the molecule can be improved to a certain extent, which can reduce the exciton annihilation phenomenon in the device, thereby achieving the effect of adjusting the luminescent color of the organic compound, improving the efficiency of the light-emitting device, and extending the life. The present inventors surprisingly discovered that, in some cases, by adjusting different substituents, the stability and service life of the device can be greatly improved. DETAILED DESCRIPTION

[0015] 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 to have high luminous efficiency, narrow luminous spectrum FWHM and long luminous lifetime.

[0016] 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.

[0017] In the description of the embodiments of the present invention, a substituent may be further substituted by a substituent, and "substituted group a" may refer to group a being substituted by a substituent, and the substituent may be substituted by at least one further substituent or may be unsubstituted.

[0018] In this disclosure, the term "and / or" describes the relationship between associated objects, indicating that three possible relationships exist. For example, "A and / or B" can represent: A exists alone, A and B exist simultaneously, and B exists alone. A and B can be singular or plural. The character " / " generally indicates that the associated objects are in an "or" relationship.

[0019] In the present invention, "at least one" means one or more, and "plurality" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c" or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can each be single or plural.

[0020] It should be understood that in various embodiments of the present invention, the size of the serial numbers of the above-mentioned processes does not mean the order of execution. Some or all of the steps can be executed in parallel or sequentially. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present invention.

[0021] The terms used in the embodiments of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The singular forms "a", "an", "the" and "the" used in the embodiments of the present invention and the appended claims are also intended to include plural forms unless the context clearly indicates otherwise.

[0022] The term "OLED" is an abbreviation for "Organic Light Emitting Diode," which stands for organic electroluminescent diode, also known as organic electric laser display or organic light-emitting semiconductor (Organic Electroluminescence Display, OLED). OLED is a current-type organic light-emitting device that emits light through the injection and recombination of carriers, and the luminous intensity is proportional to the injected current. Under the action of the electric field, the holes generated by the anode and the electrons generated by the cathode will move, and are injected into the hole transport layer and the electron transport layer respectively, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite the light-emitting molecules and ultimately produce visible light.

[0023] The term "TADF," short for "Thermally Activated Delayed Fluorescence," refers to thermally activated delayed fluorescence, which occurs when the triplet excited state and singlet excited state are close in energy, allowing the triplet excited state to transition to the singlet excited state through thermally activated reverse intersystem crossing (ISC). Conventional luminescence occurs as fluorescence and phosphorescence, respectively, where the exciton returns to the ground state via radiative emission from the singlet and triplet states. Furthermore, the energy difference between the lower singlet and triplet states is typically large, resulting in an inability to return the exciton to the singlet state once it reaches the triplet state through ISC.

[0024] In the present invention, main body material, matrix material, host material and matrix material have the same meaning and can be interchanged.

[0025] In the present invention, guest material, luminescent material and emitter material have the same meaning and can be interchanged.

[0026] In the present invention, color converter, color conversion layer and CCL have the same meaning and can be interchanged.

[0027] In the present invention, composition, printing ink, ink and ink have the same meaning and can be interchanged.

[0028] In the present invention, "substituted" means that a hydrogen atom in a compound is replaced by a substituent.

[0029] In the present invention, when the same substituent appears multiple times, each substituent may be independently selected from different groups.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] In the embodiments of the present invention, the energy level structure of the organic material, the singlet energy level S1, the triplet energy level T1, the HOMO, and the LUMO play a key role. The determination of these energy levels is described below.

[0034] 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.

[0035] 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).

[0036] 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 onset and peak points on a 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, and T1 are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0037] 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.

[0038] The present invention relates to an organic compound containing boron and nitrogen, having a structure as shown in chemical formula (I) or chemical formula (II):

[0039] wherein: Ring A and Ring B are independently selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted fused ring structure; Y is independently selected from C-R1 or N, the same or different; V1 is independently selected from C-R2 or N, the same or different; Q and Z are selected from S, O or C-R3R4; R1-R4 are each independently selected from H or 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 a 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 or 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, and one or more of R1 to R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

[0040] In some embodiments, in the boron-nitrogen-containing organic compound, ring A and ring B are independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.

[0041] In some embodiments, Ring A and Ring B, at each occurrence, may be selected from, the same or different, 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 preferred embodiments, Ring A and Ring B, at each occurrence, may be selected from, the same or different, a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 40 ring atoms, or a combination of these groups. In some more preferred embodiments, Ring A and Ring B, at each occurrence, may be selected from, the same or different, 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 more preferred embodiments, Ring A and Ring B, at each occurrence, may be the same or different 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 further more preferred embodiments, Ring A and Ring B, at each occurrence, may be the same or different selected 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.

[0042] In a preferred embodiment, Q is selected from O; in another preferred embodiment, Q is selected from S.

[0043] In a preferred embodiment, Z is selected from O; in another preferred embodiment, Z is selected from S. In certain embodiments, Z is selected from C-R3R4.

[0044] In some preferred embodiments, the boron-nitrogen-containing organic compound has a structure as shown in one of Chemical Formula (I-1) to Chemical Formula (I-3) or Chemical Formula (II-1) to Chemical Formula (II-3):

[0045] wherein V1 and Q are as defined above, and R5 is as defined above for R1.

[0046] In some preferred embodiments, the boron-nitrogen-containing organic compound has a structure as shown in one of Chemical Formula (I-1a) to Chemical Formula (I-3a) or Chemical Formula (II-1a) to Chemical Formula (II-3a):

[0047] Wherein V1, Q, R2, and R5 are as defined above.

[0048] In certain embodiments, R2 is independently selected at each occurrence from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a ... Hexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl One or more of oxazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy.

[0049] In certain embodiments, Ring A and Ring B are 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 each occurrence of V is independently selected from C-R6 or N-R7; each occurrence of W is independently selected from B-R8, C(=O), N-R9, O, S, P, P=O or P=S;

[0052] R6-R9, at each occurrence, are selected, identically or differently, from H or 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 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 or 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 may form a ring system with each other and / or the group to which they are bonded.

[0053] More preferably, the aromatic or heteroaromatic ring system is selected from the following groups:

[0054] Wherein, the definitions of W and V are the same as above.

[0055] 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.

[0056] In certain embodiments, R1-R4, at each occurrence, may be independently selected from the following groups:

[0057] Where: Each time X appears, it is independently selected from CR 10 or N; Z each time occurs, is independently selected from BR 11 、C(=O)、NR 12 , O, S, P, P=O or P=S; R 10 -R 12On each occurrence, it is selected, identically or differently, from H or 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 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 or 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 bonded; n1, n2, n3, n4 are all integers greater than or equal to 1.

[0058] Furthermore, R1-R4, when each occurs, are independently selected from the following groups:

[0059] Among them: The H atoms on the ring can be further substituted.

[0060] In some preferred embodiments, the boron-nitrogen-containing organic compound, the R is independently selected from hydrogen atom, deuterium atom, tritium atom, halogen atom, adamantyl, methyl, deuterated methyl, tritated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritated ethyl, isopropyl, deuterated isopropyl, tritated isopropyl, tert-butyl, deuterated tert-butyl, tritated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritated cyclopentyl phenyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbofuranyl, One or more of oxazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy.

[0061] In a more preferred embodiment, at least a portion of the H in the boron-nitrogen-containing organic compound is deuterated, preferably 10% or more of the H is deuterated, more preferably 20% or more of the H is deuterated, very preferably 30% or more of the H is deuterated, and most preferably 40% or more 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 is to modify the boron-nitrogen ring structure by using indolefurans as modifying groups to adjust the optical properties of the existing boron-nitrogen skeleton; at the same time, the frontier orbital energy level of the boron-nitrogen-containing organic compound can be effectively adjusted, and the multiple resonance effect of the rigid conjugated plane of the boron-nitrogen ring structure can be enhanced, thereby achieving the effect of adjusting the luminous color of the boron-nitrogen-containing organic compound and narrowing the FHWM of the luminescence spectrum; in addition, compared with the traditional aromatic amine-type skeleton, the indolefuran-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] The other type is to modify the boron-nitrogen ring structure by using indolothiophenes as modifying groups. Since the S in thiophene has a heavy atom effect, it is beneficial for boron-nitrogen compounds with TADF effect to improve the ability of intersystem crossing and improve the luminescence efficiency of the boron-nitrogen organic compounds; it can also improve the stability of the compounds.

[0065] The boron-nitrogen-containing organic compound according to the present invention can be used as an organic functional material in electronic devices, particularly light-emitting devices. The light-emitting device can be selected from color converters, OLEDs, OLEECs, and organic light-emitting field-effect transistors; OLEDs 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 compound according to the present invention can be used as a luminescent material.

[0066] In a preferred embodiment, the light emitting device has a light emission wavelength of 300 nm to 1500 nm, preferably 400 nm to 1000 nm, and more preferably 400 nm to 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 a preferred embodiment, the boron-nitrogen-containing organic compound according to the present invention has a narrow full width at half maximum (FWHM), generally ≤35 nm, preferably ≤32 nm, more preferably ≤30 nm, particularly preferably ≤28 nm, most preferably ≤26 nm.

[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 ≥ 0.5 eV.

[0073] In other preferred embodiments, the boron-nitrogen-containing organic compound according to the present invention has ((LUMO+1)-LUMO) ≥ 0.2 eV, preferably ≥ 0.3 eV, more preferably ≥ 0.4 eV, most preferably ≥ 0.5 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 aryloxycarbonyl, cyano, carbamoyl , haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a cross-linkable group, a substituted aryl group having 5 to 60 ring atoms, an unsubstituted aryl group having 5 to 60 ring atoms, a substituted heteroaryl group having 5 to 60 ring atoms, an 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.

[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 aryloxycarbonyl, cyano, carbamoyl , haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a cross-linkable group, a substituted aryl group having 5 to 60 ring atoms, an unsubstituted aryl group having 5 to 60 ring atoms, a substituted heteroaryl group having 5 to 60 ring atoms, an 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 one of the above-mentioned boron-nitrogen-containing organic compounds or polymers and at least one organic functional material. The organic functional material is selected from at least one of a color conversion material, 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, wherein the luminophore is selected from a singlet luminophore (fluorescent luminophore), a triplet luminophore (phosphorescent luminophore), or an organic thermally excited delayed fluorescence material (TADF material). For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymeric 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, more 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 ≥0.5 mg / mL at 25°C, preferably ≥1 mg / mL, more preferably ≥2 mg / mL, and most preferably ≥3 mg / mL.

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

[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 the concentration of the functional material in the ink. The ink containing the boron-nitrogen-containing organic compound 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 at least one 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, 1-methoxynaphthalene, cyclohexylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, 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, 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-ethylphenyl ether, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene , glycidyl phenyl 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 at least one 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 or polymer 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 boron-nitrogen-containing organic compound or its mixture or polymer.

[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, gravure printing, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slot extrusion coating, etc. 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., for adjusting viscosity, film-forming properties, and improving adhesion. For more information on printing techniques and their requirements for solutions, such as solvents, concentrations, and viscosities, please refer to "Handbook of Print Media: Technologies and Production Methods," edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0107] Based on the above-mentioned boron-nitrogen-containing organic compound or polymer, the present invention further provides an application of the above-mentioned boron-nitrogen-containing organic compound or polymer, 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, a color converter, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLED), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (OPED). Organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors (OLEDs), are particularly preferred. In an embodiment of the present invention, the boron-nitrogen-containing 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 an organic compound, polymer, or mixture containing boron and nitrogen 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 organic compound, polymer, or mixture containing boron and nitrogen 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). Organic electroluminescent devices, such as OLEDs, OLEECs, and OLEDs, are particularly preferred.

[0109] 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.

[0110] The organic electronic device described above, especially the OLED, includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0111] 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 glycol (2,6-naphthalene) (PEN).

[0112] The anode can include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or 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 or 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.

[0113] 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.

[0114] 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.

[0115] In a preferred embodiment, in the organic light-emitting device according to the present invention, the light-emitting layer thereof is prepared by the composition according to the present invention.

[0116] The organic 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.

[0117] 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.

[0118] 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.

[0119] Example

[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] 1. Synthesis of compounds

[0122] Synthesis of intermediate 1c:

[0123] 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.

[0124] 1-Bromo-2-chloro-3-fluorobenzene (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 89 g of intermediate 1c in an 89% yield. Product characterization: MS (ASAP) = 466.

[0125] Synthesis of intermediate 1d:

[0126] Benzofuran-2-boronic acid pinesyl ester (100 g), o-bromonitrobenzene (100 g), tetrakistriphenylphosphine palladium (16 g), and sodium carbonate (67 g) were dissolved in toluene (500 mL) and water (100 mL), heated to 100°C, and stirred for 24 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 1h in a 77% yield. Product characterization: MS (ASAP) = 239.

[0127] Intermediate 1h (50 g) and triphenylphosphine (30 g) were dissolved in o-dichlorobenzene, heated to 160°C, and stirred for 48 hours. The reaction solution was cooled to room temperature and extracted with a large amount of deionized water and 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 30 g of intermediate 1d in a 60% yield. Product characterization: MS (ASAP) = 206.

[0128] Synthesis of intermediate 2c:

[0129] Under nitrogen, a three-necked flask was charged with 2a (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 evaporated to dryness to obtain 180 g of crude product 2b. The product 2b was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to yield 95 g, a 95% yield.

[0130] 2b (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 78 g of intermediate 2c in a 78% yield. Product characterization: MS (ASAP) = 547.

[0131] Synthesis of intermediate 3c:

[0132] 1a (100 g), 3b (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 91 g of intermediate 3c in a 91% yield. Product characterization: MS (ASAP) = 391.6.

[0133] Synthesis of intermediate 4d:

[0134] 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 4b 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 product 4b. The product 4b was separated by column chromatography (petroleum ether / ethyl acetate 15:1) to yield 142 g, a yield of 71%.

[0135] 4b (100 g), intermediate 3c (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 4d in an 85% yield. Product characterization: MS (ASAP) = 685.

[0136] Synthesis of intermediate 5b:

[0137] 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 78 g of intermediate 5b in a 78% yield. Product characterization: MS (ASAP) = 371.5.

[0138] Synthesis of intermediate 5c:

[0139] Intermediate 5b (100 g), 1-bromo-2-chloro-3-fluorobenzene (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 an 82% yield. Product characterization: MS (ASAP) = 465.6.

[0140] Synthesis of intermediate 6a:

[0141] Benzofuran-2-boronic acid pinesyl ester (100 g), 1-bromo-4-tert-butyl-2-nitrobenzene (100 g), tetrakistriphenylphosphine palladium (16 g), and sodium carbonate (67 g) were dissolved in toluene (500 mL) and water (100 mL), heated to 100°C, and stirred for 24 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 96 g of intermediate 6p in a 96% yield. Product characterization: MS (ASAP) = 295.

[0142] Intermediate 6p (50 g) and triphenylphosphine (30 g) were dissolved in o-dichlorobenzene, heated to 160°C, and stirred for 48 hours. The reaction solution was cooled to room temperature and extracted with a large amount of deionized water and 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 40 g of intermediate 6a in an 80% yield. Product characterization: MS (ASAP) = 262.

[0143] Synthesis of intermediate 8a:

[0144] 8d (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 95 g of intermediate 8e in a 95% yield. Product characterization: MS (ASAP) = 337.5.

[0145] 2b (100 g), intermediate 8e (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 78 g of intermediate 8a in a 78% yield. Product characterization: MS (ASAP) = 547.

[0146] Synthesis of compound 1:

[0147] Intermediate 1c (100 g), intermediate 1d (100 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 90 g of intermediate 1e in an 85% yield.

[0148] Intermediate 1e (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) = 626.

[0149] Synthesis of compound 2:

[0150] Intermediate 1d (100 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 96 g of intermediate 2d in a 96% yield.

[0151] 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) = 707.

[0152] Synthesis of compound 3:

[0153] 1-Bromo-2-chloro-3-fluorobenzene (100 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.

[0154] Intermediate 1d (50 g), intermediate 3d (50 g), and anhydrous cesium carbonate (100 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 18 g of intermediate 3e in a 35% yield.

[0155] Intermediate 3e (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) = 680.

[0156] Synthesis of compound 4:

[0157] Intermediate 4d (100 g), intermediate 1d (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 53 g of intermediate 4e in a 53% yield.

[0158] 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) = 832.9.

[0159] Synthesis of compound 5:

[0160] Intermediate 5c (100 g), intermediate 1d (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 64 g of intermediate 5d in a 64% yield.

[0161] 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) = 647.6.

[0162] Synthesis of compound 6:

[0163] Intermediate 4d (100 g), intermediate 6a (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 6b with a yield of 43%.

[0164] Intermediate 6b (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 6 in a 30% yield. Product characterization: MS (ASAP) = 902.

[0165] Synthesis of compound 7:

[0166] Intermediate 2c (100 g), 7a (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 92 g of intermediate 7b with a yield of 92%.

[0167] Intermediate 7b (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 7 in a 34% yield. Product characterization: MS (ASAP) = 723.

[0168] Synthesis of compound 8:

[0169] 8a (100 g), intermediate 1d (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 92 g of intermediate 8b in a 92% yield.

[0170] 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 3.5 g of compound 8 in a 35% yield. Product characterization: MS (ASAP) = 691.

[0171] Synthesis of compound 9:

[0172] Intermediate 1c (100 g), intermediate 9a (100 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 91 g of intermediate 9b with a yield of 85%.

[0173] Intermediate 9b (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 3.2 g of compound 9 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0174] Synthesis of compound 10:

[0175] Intermediate 1c (100 g), intermediate 10a (100 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 92 g of intermediate 10b with a yield of 85%.

[0176] Intermediate 10b (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 3.4 g of compound 10 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0177] Synthesis of compound 11:

[0178] Intermediate 11a (100 g), intermediate 9a (100 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 93 g of intermediate 11b with a yield of 85%.

[0179] Intermediate 11b (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 3.2 g of compound 11 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0180] Synthesis of compound 12:

[0181] Intermediate 11a (100 g), intermediate 10a (100 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 94 g of intermediate 12a with a yield of 85%.

[0182] Intermediate 12a (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 3.4 g of compound 12 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0183] Synthesis of compound 13:

[0184] Intermediate 13a (100 g), intermediate 9a (100 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 89 g of intermediate 13b with a yield of 84%.

[0185] Intermediate 13b (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 3.2 g of compound 13 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0186] Synthesis of compound 14:

[0187] Intermediate 13a (100 g), intermediate 10a (100 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 91 g of intermediate 14a with a yield of 85%.

[0188] Intermediate 14a (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 3.1 g of compound 14 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0189] Synthesis of compound 16:

[0190] Intermediate 13a (100 g), intermediate 1d (100 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 93 g of intermediate 16a with a yield of 85%.

[0191] Intermediate 16a (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 3.5 g of compound 16 in a 34% yield. Product characterization: MS (ASAP) = 626.

[0192] Synthesis of compound 17:

[0193] Intermediate 17a was synthesized according to the synthetic method of reference: (DOI: 10.31635 / ccschem.021.202101033).

[0194] Intermediate 17a (10 g), intermediate 17b (12 g), potassium carbonate (2 g), and tetrakistriphenylphosphine palladium (0.5 g) were dissolved in a mixture of toluene, ethanol, and water (5:1:1), 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 15 g of intermediate 17c in an 85% yield.

[0195] Intermediate 17c (1 g), intermediate 17d (1.2 g), potassium carbonate (2 g), and tetrakistriphenylphosphine palladium (0.5 g) were dissolved in a mixture of toluene, ethanol, and water (5:1:1), heated to 100°C, and stirred for 8 hours. The reaction solution was cooled to room temperature and then poured into methanol (50 mL) and stirred. The precipitate was collected by filtration and washed with 2M HCl and MeOH. It was then extracted with chloroform and added to methanol again to precipitate compound 17.

[0196] Synthesis of compound 18:

[0197] Intermediate 18a (100 g) (synthesized with reference to Intermediate 1c), Intermediate 1d (100 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 45 g of Intermediate 18b in a 46% yield.

[0198] Intermediate 18b (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 18 in a 34% yield. Product characterization: MS (ASAP) = 722.

[0199] Synthesis of compound 19:

[0200] Intermediate 19a (100 g) (synthesized with reference to Intermediate 1c), Intermediate 1d (100 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 85 g of Intermediate 19b with an 80% yield.

[0201] Intermediate 19b (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 3.2 g of compound 19 in a 32% yield. Product characterization: MS (ASAP) = 702.

[0202] Synthesis of compound 20:

[0203] Intermediate 19a (100 g) (synthesized with reference to Intermediate 1c), Intermediate 20a (100 g) (synthesized with reference to Intermediate 1d), 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 75 g of Intermediate 20b with a yield of 71%.

[0204] Intermediate 20b (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 3.1 g of compound 20 in a 31% yield. Product characterization: MS (ASAP) = 868.

[0205] Synthesis of compound 21:

[0206] Intermediate 21a (100 g) (synthesized with reference to Intermediate 1c), Intermediate 1d (100 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 65 g of Intermediate 21b in a 60% yield.

[0207] Intermediate 21b (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 3.0 g of compound 21 in a 30% yield. Product characterization: MS (ASAP) = 651.

[0208] Synthesis of compound 22:

[0209] Intermediate 4d (100 g), intermediate 22a (100 g) (refer to the synthesis of intermediate 1d), 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 69 g of intermediate 22b in a 68% yield.

[0210] Intermediate 22b (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 2.8 g of compound 22 in a 28% yield. Product characterization: MS (ASAP) = 902.

[0211] Synthesis of compound 23:

[0212] Intermediate 13a (100 g) (synthesized with reference to Intermediate 1c), Intermediate 23a (100 g) (synthesized with reference to Intermediate 1d), 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 85 g of Intermediate 23b with a yield of 83%.

[0213] Intermediate 23b (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 1.1 g of compound 23 in an 11% yield. Product characterization: MS (ASAP) = 802.

[0214] Synthesis of compound 24:

[0215] Intermediate 24a (100 g) (synthesized with reference to Intermediate 1c), Intermediate 1d (100 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 85 g of Intermediate 24b in an 83% yield.

[0216] Intermediate 24b (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 0.9 g of compound 24 in a 9% yield. Product characterization: MS (ASAP) = 847.

[0217] Synthesis of compound 25:

[0218] Intermediate 5c (100 g), intermediate 25a (100 g) (refer to the synthesis of intermediate 1d), 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 65 g of intermediate 25b in a 65% yield.

[0219] Intermediate 25b (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 0.8 g of compound 25 in an 8% yield. Product characterization: MS (ASAP) = 661.

[0220] Comparative Compound 1

[0221] The existing boron-nitrogen material structure is as follows:

[0222] 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.

[0223] Comparative Compound 2-Comparative Compound 5

[0224] The structure of boron-nitrogen material is as follows:

[0225] The specific synthesis method of the boron-nitrogen material can be referred to patent WO2021107678, and the present invention will not go into details.

[0226] 2. Energy level structure of the compound

[0227] The energy levels of organic compounds can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian 09W (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, using S1 and T1 as is. HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206 LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0228] 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:

[0229] Table 1

[0230] 3. Preparation and Characterization of OLED Devices

[0231] Example 1 (Preparation of OLED Device 1)

[0232] 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 and then perform Ar2 ozone treatment.

[0233] 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.

[0234] Step S3: On the hole injection layer, 125 nm of hole transport layer material HT-1 is evaporated by vacuum evaporation.

[0235] Step S4: On the hole injection layer, 10 nm of electron blocking layer material HT-2 is deposited by vacuum evaporation.

[0236] Step S5: On the electron blocking layer, a light-emitting layer is deposited by vacuum evaporation. The host material is BH and the guest material is the compound 6 of the present invention. The mass ratio is 98:2 and the thickness is 25 nm.

[0237] Step S6: depositing 2 nm of hole blocking layer material ET-1 on the light-emitting layer by vacuum evaporation.

[0238] 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.

[0239] Step S8: 1.5 nm of Yb is evaporated on the electron transport layer by vacuum evaporation as an electron injection layer.

[0240] Step S9: 17 nm of Mg:Ag (1:9) alloy was evaporated on the electron injection layer as a cathode.

[0241] Step S10: evaporating 55 nm of CPL material on the cathode layer.

[0242] The following are the structural formulas of the materials used in each functional layer:

[0243] Example 2 (Preparation of OLED Device 2)

[0244] 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 guest material is compound 7. The remaining steps are the same as in Example 1; please refer to Example 1 for details.

[0245] Example 3 (Preparation of OLED Device 3)

[0246] 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 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.

[0247] Example 4 (Preparation of OLED Device 4)

[0248] 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 13 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.

[0249] Example 5 (Preparation of OLED Device 5)

[0250] 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 19 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.

[0251] Example 6 (Preparation of OLED Device 6)

[0252] 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 23 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.

[0253] Example 7 (Preparation of OLED Device 7)

[0254] 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 guest material in step S5 is compound 25. The remaining steps are the same as in Example 1. For details, please refer to Example 1.

[0255] Comparative Example 1 (Preparation of OLED Device 8)

[0256] 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-evaporated onto the hole injection layer, and in step S5, the guest material is the existing boron-nitrogen material of Comparative Compound 1. The remaining steps are identical to those of Example 1; please refer to Example 1 for details.

[0257] Comparative Example 2 (Preparation of OLED Device 9)

[0258] Comparative Example 2 differs from Example 1 in that, in step S3, a 121 nm thick layer of hole transport layer material HT-1 is vacuum-evaporated onto the hole injection layer, and in step S5, the guest material is the existing boron-nitrogen material of Comparative Compound 2. The remaining steps are identical to those of Example 1; please refer to Example 1 for details.

[0259] Comparative Example 3 (Preparation of OLED Device 10)

[0260] Comparative Example 3 differs from Example 1 in that, in step S3, a 121 nm thick layer of hole transport layer material HT-1 is vacuum-evaporated onto the hole injection layer, and in step S5, the guest material is the existing boron-nitrogen material of Comparative Compound 4. The remaining steps are identical to those of Example 1; please refer to Example 1 for details.

[0261] Comparative Example 4 (Preparation of OLED Device 11)

[0262] Comparative Example 4 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. In step S5, the guest material is the existing boron-nitrogen material of Comparative Compound 5. The remaining steps are identical to those of Example 1. Please refer to Example 1 for details.

[0263] The performance of the devices prepared in Examples 1 to 7 and Comparative Examples 1 to 4 are shown in Table 2. The current efficiency, EQE and LT95 are all based on the comparative examples.

[0264] Table 2

[0265] Note: EQE: External Quantum Efficiency; LT95@1000nit: The operating time when the device experiences 5% brightness loss at 1000 nits brightness.

[0266] From the external quantum efficiency (EQE), 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 Examples 1 to 4 in Table 2, it can be seen that compared with Comparative Examples 1 to 4, the OLED devices of Examples 1 to 7 using the boron-nitrogen-containing organic compounds synthesized by the present invention exhibit higher luminescence efficiency and narrower FWHM, as well as longer operating life and higher device stability. It can be seen that the introduction of conjugated groups as modifying groups in the thiophene and furan structures adjacent to the boron atom can greatly improve the optical properties of the boron-nitrogen skeleton. By introducing conjugated groups (i.e., ring B), the overall conjugation length of the boron-nitrogen molecule can be extended, significantly improving the stability of the overall molecular structure and increasing the device life. At the same time, the ring closure position of the thiophene and furan rings with the boron atom will greatly affect the luminescence peak position of the compound, causing the spectrum to red-shift and accompanied by spectrum broadening, which is unfavorable for the design of light-emitting devices, especially short-wavelength molecules. The spectrum of the comparative compound 3 with ring closure on the other side shows green light emission, so no further device comparison characterization was performed.

[0267] 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 having a structure as shown in Chemical Formula (I) or Chemical Formula (II): in: Ring A and Ring B are independently selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 6 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted fused ring structure; Y is the same or different and is independently selected from C-R1 or N; V1 is the same or different and is independently selected from C-R2 or N; Q, Z are selected from S, O or C-R3R4; R1-R4, at each occurrence, are selected, identically or differently, from H or 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 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, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F or 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, and one or more groups of R1 to R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which they are bonded.

2. The boron-nitrogen-containing organic compound according to claim 1, having a structure as shown in one of Chemical Formula (I-1) to Chemical Formula (I-3) or Chemical Formula (II-1) to Chemical Formula (II-3): V1, at each occurrence, is identically or differently selected from C-R2 or N; The definition of R5 is the same as that of R1 in claim 1.

3. The boron-nitrogen-containing organic compound according to claim 1 or 2, having a structure as shown in one of Chemical Formula (I-1a) to Chemical Formula (I-3a) or Chemical Formula (II-1a) to Chemical Formula (II-3a):

4. The boron-nitrogen-containing organic compound according to claim 3, characterized in that R2 is independently selected from hydrogen, deuterium, tritium, halogen, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, benzene, benzophenone ... phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, One or more of 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy.

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 comprising at least one 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 comprising an organic compound containing boron and nitrogen as claimed in any one of claims 1 to 4 or a polymer as claimed 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 a color converter, an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor or an organic plasmon emission diode.

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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