Boron-containing carbazole organic compounds, mixtures, compositions and organic electronic devices

Abstract

The present application discloses a boron-containing carbazole organic compound and a mixture, a composition and an organic electronic device comprising the boron-containing carbazole organic compound. The boron-containing carbazole organic compound has a structure as shown in the general formula (1): The boron-containing carbazole organic compound is used in an organic electronic device, in particular as a luminescent material in a light-emitting layer of an organic electronic device, to improve the efficiency and life of the organic electronic device.

Description

Technical Field

[0001] The present application relates to the technical field of luminescent materials, and in particular to a boron-containing carbazole organic compound, and a mixture, a composition, and an organic electronic device comprising the boron-containing carbazole organic compound. Background Art

[0002] Organic semiconductor materials offer diverse synthesis methods, relatively low manufacturing costs, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad potential for development in optoelectronic devices (such as flat-panel displays and lighting) due to their advantages, including wide viewing angles, fast response times, low operating voltages, and thin panels.

[0003] To improve the luminous efficiency of organic light-emitting diodes, various fluorescent and phosphorescent luminescent material systems have been developed. Among them, organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescence quantum efficiency is limited to 25% under electrical excitation. This is because the branching ratio between the singlet excited state and the triplet excited state of the exciton is 1:3. Organic light-emitting diodes using phosphorescent materials have achieved an internal electroluminescence quantum efficiency of almost 100%, but phosphorescent OLEDs also produce a roll-off effect, that is, the luminous efficiency decreases rapidly with the increase of current or brightness, which is particularly unfavorable for high-brightness applications.

[0004] To date, the traditional phosphorescent materials with practical application have been metal complexes containing iridium and platinum. However, these raw materials are rare and expensive, and the synthesis of metal complexes is complex, resulting in high costs. To overcome these issues, Adachi proposed the concept of reverse internal conversion, which uses organic compounds instead of metal complexes as the luminescent material to achieve high efficiencies comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as composite excited-state materials and thermally excited delayed fluorescence (TADF) materials.

[0005] Traditional organic compounds with TADF typically utilize electron-donating (Donor) and electron-withdrawing (Acceptor) groups linked together, resulting in a complete separation of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) electron cloud distributions, narrowing the difference (ΔEST) between the singlet (S1) and triplet (T1) states of the organic compound. Traditional blue-emitting TADF materials still lag behind phosphorescent materials in terms of both efficiency and lifetime. Summary of the Invention

[0006] In view of this, the present application provides a boron-containing carbazole organic compound as a new type of luminescent material, which is used in organic electronic devices to improve the problems of low luminous efficiency and short life of organic electronic devices.

[0007] The technical solution of this application is as follows:

[0008] A boron-containing carbazole organic compound having a structure as shown in general formula (1):

[0009]

[0010] in:

[0011] Ar1 is selected from formula (A-1) or (A-2):

[0012]

[0013] X and Y are independently selected from O, S, CR8R9 or NR 10 ;

[0014] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, a 2 to 20 C group C atoms, alkoxycarbonyl groups having 7 to 20 C atoms, aryloxycarbonyl groups having 7 to 20 C atoms, alkene groups having 1 to 20 C atoms, -CN, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations thereof;

[0015] m1 is selected from 1 or 2; m2 is selected from 1 or 2; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1 or 2; n3 is selected from 0, 1, 2 or 3; n4 is selected from 0, 1, 2 or 3; n5 is selected from 0, 1, 2 or 3; n6 is selected from 0, 1, 2, 4, 5 or 6; n7 is selected from 0, 1, 2, 3 or 4;

[0016] Two adjacent R1s may form a ring or not; two adjacent R2s may form a ring or not; two adjacent R3s may form a ring or not; two adjacent R5s may form a ring or not.

[0017] Correspondingly, the present application also provides a mixture comprising the above-mentioned boron-containing carbazole organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials or organic dyes.

[0018] Correspondingly, the present application also provides a composition comprising the above-mentioned boron-containing carbazole organic compound or the above-mentioned mixture, and at least one organic solvent.

[0019] Correspondingly, the present application also provides an organic electronic device, comprising at least one organic functional layer, wherein the organic functional layer comprises the above-mentioned boron-containing carbazole organic compound or the above-mentioned mixture, or the organic functional layer is prepared from the above-mentioned composition.

[0020] Compared with the prior art, the boron-containing carbazole organic compound of the present application has the following beneficial effects:

[0021] The boron-containing carbazole organic compound of the present invention introduces dibenzofuran, dibenzothiophene, carbazole, fluorene, benzopentacyclic ring, and / or naphthalene into the boron-nitrogen compound, enhancing the overall molecular conjugation and improving the device's luminous efficiency and lifespan. Furthermore, the introduction of tetralin and indane improves the overall molecular solubility and facilitates compound purification, thereby increasing the purity of the boron-containing carbazole organic compound and further extending the device's luminous efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0023] Figure 1 This is a schematic structural diagram of an organic electronic device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0024] The following, in conjunction with the accompanying drawings, provides a clear and complete description of the technical solutions in the embodiments of this application. It should be understood that the described embodiments are only some of the embodiments of this application, and not all of them. Based on the embodiments of this application, all other embodiments derived by those skilled in the art without inventive effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are intended only to illustrate and explain this application and are not intended to limit this application. In this application, unless otherwise indicated, directional terms such as "upper" and "lower" generally refer to the upper and lower parts of a device in actual use or operation, specifically the directions of the drawings in the accompanying drawings. Furthermore, in the description of this application, the term "including" means "including but not limited to," the term "plurality" means "two or more," and the term "and / or" includes any and all combinations of one or more of the associated listed items. The various embodiments of this application may be presented in the form of a range. It should be understood that describing in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of this application. Therefore, the range description should be considered to have specifically disclosed all possible subranges and individual numerical values ​​within the range. For example, description of a range from 1 to 6 should be considered to have specifically disclosed subranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as individual numbers within that range, such as 1, 2, 3, 4, 5, and 6. Furthermore, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the indicated range.

[0025] The terms "and / or", "or / and", and "and / or" used herein include any one of two or more related listed items, and also include any and all combinations of the related listed items, wherein the arbitrary and all combinations include any combination of two related listed items, any more related listed items, or all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or", "or / and", and "and / or", it should be understood that in this application, the technical solution undoubtedly includes technical solutions connected by "logical and" and also undoubtedly includes technical solutions connected by "logical or". For example, "A and / or B" includes three parallel solutions of A, B and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, the technical solution of all being connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, the combination of any two or any three of A, B, C, and D, and also includes the four-item combination of A, B, C, and D (that is, the technical solution of all being connected by "logical AND").

[0026] In this application, composition and printing ink, or ink have the same meaning and can be used interchangeably.

[0027] In this application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0028] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0029] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0030] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0031] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, , cyano, isocyano, nitro or halogen, alkyl groups containing 1 to 10 carbon atoms, heterocyclic groups containing 3 to 20 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, deuterium atoms, cyano, isocyano, nitro or halogen, alkyl groups containing 1 to 10 carbon atoms, heterocyclic groups containing 3 to 10 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms, silanyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art.

[0032] In this application, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, 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 is also the same 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.

[0033] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0034] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom on the basis of aryl is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidine 1-Hydroxy-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine,

[0035] In this application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl at each occurrence. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 1-Hexyl, 2 ...

[0036] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0037] As used herein, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amino groups include -NH2, -N(alkyl), -NH(alkyl), -N(cycloalkyl), -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0038] In this application, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, an amino group refers to -NH2, a formyl group refers to -C(=O)H, a haloformyl group refers to -C(=O)Z (wherein Z represents a halogen), a carbamoyl group refers to -C(=O)NH2, an isocyanate group refers to -NCO, and an isothiocyanate group refers to -NCS.

[0039] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", i.e., an alkyl group as defined above connected to another group via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to, methoxy (-O-CH or -OMe), ethoxy (-O-CHCH or -OEt), and tert-butoxy (-OC(CH) or -OtBu).

[0040] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0041] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as the linking site.

[0042] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0043] In this application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0044] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0045] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0046] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0047] In the present application, "two adjacent R1 or R3 or R5 form a ring with each other" means a ring system formed by two adjacent 1 or 3 or R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0048] In this application, the terms "combination thereof", "any combination thereof", "any combination thereof" and the like include all suitable combinations of any two or more of the listed items.

[0049] In the present application, “further”, “further”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be understood as limiting the scope of protection of the present invention.

[0050] In this application, the terms "optionally," "optional," and "optional" are optional and refer to either option being present or absent. If a technical solution contains multiple "options," each option is considered independent unless otherwise specified and there are no conflicts or constraints.

[0051] In this application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0052] In the embodiments of the present application, the energy level structure of organic materials, triplet energy levels ET, HOMO, and LUMO play a key role. The following is an introduction to these energy levels:

[0053] 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.

[0054] The triplet energy level ET1 of the organic material can be measured by low-temperature time-resolved luminescence spectroscopy, or obtained by quantum simulation calculation (such as by Time-dependent DFT), such as by the commercial software Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110 or described in the following examples.

[0055] It should be noted that the absolute values ​​of HOMO, LUMO, and ET1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. The values ​​of HOMO, LUMO, and ET1 described in the embodiments of the present invention are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0056] In this application, (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.

[0057] The technical solution of this application is as follows:

[0058] A boron-containing carbazole organic compound having a structure as shown in general formula (1):

[0059]

[0060] in:

[0061] Ar1 is selected from formula (A-1) or (A-2):

[0062]

[0063] X and Y are independently selected from O, S, CR8R9 or NR 10 ;

[0064] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each occurrence is independently selected from: -H, -D (deuterium), a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, a 2 to 2 an alkoxycarbonyl group having 0 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, -CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;

[0065] m1 is selected from 1 or 2; m2 is selected from 1 or 2; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1 or 2; n3 is selected from 0, 1, 2 or 3; n4 is selected from 0, 1, 2 or 3; n5 is selected from 0, 1, 2 or 3; n6 is selected from 0, 1, 2, 4, 5 or 6; n7 is selected from 0, 1, 2, 3 or 4;

[0066] Two adjacent R1s may form a ring or not; two adjacent R2s may form a ring or not; two adjacent R3s may form a ring or not; two adjacent R5s may form a ring or not.

[0067] In some embodiments, the structure of the boron-containing carbazole organic compound is selected from the structure shown in formula (2-1) or (2-2):

[0068]

[0069] In some embodiments, the structure of the boron-containing carbazole organic compound is selected from any one of the structures shown in formulas (3-1) to (3-6):

[0070]

[0071] In one embodiment, Ar1 is selected from any one of the structures shown in formula (B-1) to (B-5):

[0072]

[0073] Where: * indicates the fusion site.

[0074] In some embodiments, each occurrence of R6 and R7 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, or a combination of these groups; further, each occurrence of R6 and R7 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 5 C atoms, or a combination of these groups.

[0075] In some embodiments, each occurrence of R1 is independently selected from: -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or a combination thereof. Furthermore, each occurrence of R1 is independently selected from: -H, -D, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 5 carbon atoms, or a combination thereof.

[0076] In one embodiment, two adjacent R1 groups do not form a ring with each other.

[0077] In other embodiments, two adjacent R1s form a ring with each other. Further, two adjacent R1s form a ring with each other to form a 6-membered aromatic ring or aliphatic ring. Further, two adjacent R1s form a ring with each other to form Wherein, * indicates the attachment site.

[0078] In some embodiments, each occurrence of R2 is independently selected from: -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or a combination thereof. Furthermore, each occurrence of R2 is independently selected from: -H, -D, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 5 carbon atoms, or a combination thereof.

[0079] In one embodiment, two adjacent R2 groups do not form a ring with each other.

[0080] In other embodiments, two adjacent R2s are mutually cyclic. Further, two adjacent R2s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring. Further, two adjacent R2s are mutually cyclic to form Wherein, * indicates the attachment site.

[0081] In some embodiments, each occurrence of R3 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or a combination thereof. Furthermore, each occurrence of R3 is independently selected from -H, -D, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 5 carbon atoms, or a combination thereof.

[0082] In one embodiment, two adjacent R3 groups do not form a ring with each other.

[0083] In other embodiments, two adjacent R3s are cyclic with each other. Further, two adjacent R3s are cyclic with each other to form a 6-membered aromatic ring or aliphatic ring. Further, Selected from Wherein, * indicates the attachment site.

[0084] In some embodiments, each occurrence of R4 is independently selected from: -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or a combination thereof. Further, each occurrence of R4 is independently selected from: -H, -D, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 5 carbon atoms, or a combination thereof.

[0085] In some embodiments, each occurrence of R5 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or a combination thereof. Furthermore, each occurrence of R5 is independently selected from -H, -D, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 5 carbon atoms, or a combination thereof.

[0086] In one embodiment, two adjacent R5 groups do not form a ring with each other.

[0087] In other embodiments, two adjacent R5s form a ring with each other. Further, two adjacent R5s form a ring with each other to form a 6-membered aromatic ring or aliphatic ring. Further, Selected from Wherein, * indicates the attachment site.

[0088] In one embodiment, R8, R9, R 10 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms, or a combination of these groups; further, R8, R9, R 10 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 6 C atoms, a branched-chain alkyl group having 3 to 6 C atoms, or a cyclic alkyl group having 3 to 6 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0089] In one embodiment, X is selected from O, S, N—CH 3 , N—Ph, or C(CH 3 ) 2 .

[0090] In one embodiment, Y is selected from O, S, N-CH3, N-Ph or C(CH3)2.

[0091] In some embodiments, the structure of the boron-containing carbazole organic compound is selected from any one of the following structures:

[0092]

[0093]

[0094] As an example, in some embodiments, the boron-containing carbazole organic compound of the present application can be selected from but not limited to any one of the following structures:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] It is understood that the H in the structural formula of the above-mentioned boron-containing carbazole organic compound can be further substituted.

[0102] In some embodiments, the boron-containing carbazole organic compounds of the present application can be used as organic functional materials in the functional layers of organic electronic devices, particularly in the functional layers of OLED devices. The organic functional materials can be, but are not limited to, 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 guest materials (Emitters), luminescent host materials (HostEmitters), and organic dyes.

[0103] In some embodiments, the boron-containing carbazole organic compound of the present application is used in a light-emitting layer. In at least one embodiment, the boron-containing carbazole organic compound of the present application is used in a light-emitting layer as a guest material.

[0104] In some embodiments, the boron-containing carbazole organic compound of the present application is used as a blue light emitting material in a light emitting layer.

[0105] The present application further relates to a mixture comprising at least one boron-containing carbazole organic compound as described above and at least one other organic functional material. The other organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes. The luminophore is selected from singlet luminophores (fluorescent luminophores), triplet luminophores (phosphorescent luminophores), and organic thermally excited delayed fluorescence materials (TADF materials). Detailed descriptions of various organic functional materials are provided in WO2010135519A1, US20090134784A1, and WO 2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0106] In one embodiment, the another organic functional material is selected from a light-emitting host material; further, the another organic functional material is selected from a blue-light host material; further, the blue-light host material is selected from anthracene organic compounds.

[0107] The present application also relates to a composition comprising at least one boron-containing carbazole organic compound or mixture as described above, and at least one organic solvent.

[0108] It will be appreciated that the composition may also be referred to as ink.

[0109] When used in printing processes, the viscosity and surface tension of the ink are important parameters. The appropriate surface tension parameters of the ink are suitable for the specific substrate and the specific printing method. In some embodiments, the surface tension of the ink according to the present application at operating temperature or 25°C ranges from 19 dyne / cm to 50 dyne / cm; more preferably, from 22 dyne / cm to 35 dyne / cm; and most preferably, from 25 dyne / cm to 33 dyne / cm. In some embodiments, the viscosity of the ink according to the present application at operating temperature or 25°C ranges from 1 cps to 100 cps; more preferably, from 1 cps to 50 cps; more preferably, from 1.5 cps to 20 cps; and most preferably, from 4.0 cps to 20 cps. Inks formulated in this manner are advantageous for inkjet printing.

[0110] It is understood that the viscosity of the ink can be adjusted by various methods, such as by selecting an appropriate solvent and the concentration of the functional material in the ink. The ink containing the boron-containing carbazole organic compound according to the present application can facilitate people to adjust the printing ink within an appropriate range according to the printing method used.

[0111] Generally, the weight ratio of the boron-containing carbazole organic compound or mixture described in the present application in the combination ranges from 0.3 to 30 wt %, preferably from 0.5 to 20 wt %, more preferably from 0.5 to 15 wt %, even more preferably from 0.5 to 10 wt %, and most preferably from 1 to 5 wt %.

[0112] The organic solvent is selected from at least one of aromatic or heteroaromatic solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0113] In at least one embodiment, in the composition, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0114] The aromatic or heteroaromatic based solvent may be selected from, but not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropyl At least one of biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 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, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0115] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Particularly preferred is at least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0116] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. For example, the derivative may be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0117] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,3-dipropoxybenzene, 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, and ethyl-2-naphthyl ether.

[0118] The aliphatic ketone-based solvent can be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or an aliphatic ether, for example, at least one of 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, and tetraethylene glycol dimethyl ether.

[0119] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0120] In some embodiments, the composition of the present application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0121] The other organic solvent can be selected from, but not limited to, at least one of 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 (DMSO), tetralin, decalin and indene.

[0122] In some embodiments, the organic solvent suitable for the present application is a solvent having a Hansen solubility parameter within the following range:

[0123] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0124] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0125] δh (hydrogen bond force) is in the range of 0.9 to 14.2 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2.

[0126] In some embodiments, the boiling point of the organic solvent used in the compositions of the present application should be considered when selecting the solvent. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging in inkjet printheads.

[0127] It will be appreciated that the organic solvent may be evaporated from the solvent system to form a thin film comprising the organic compound.

[0128] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of a surfactant, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and an adhesive.

[0129] The present application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating method. The printing or coating method can be, but is not limited to, inkjet printing, gravure printing, spray 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, pad printing, slot extrusion coating, etc. Gravure printing, spray printing, and inkjet printing are preferred.

[0130] The present application also relates to the use of the boron-containing carbazole organic compound, mixture or composition described above in organic electronic devices. The specific scheme is as follows:

[0131] An organic electronic device includes at least one organic functional layer, wherein the organic functional layer comprises at least one boron-containing carbazole organic compound or mixture as described above, or the organic functional layer is prepared from the above composition.

[0132] Furthermore, the organic electronic device comprises a cathode, an anode and at least one organic functional layer, wherein the organic functional layer comprises at least one boron-containing carbazole organic compound or mixture as described above, or the organic functional layer is prepared from the above composition.

[0133] The organic functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer (HBL). In at least one embodiment, the organic functional layer is an emitting layer.

[0134] The organic electronic device may be, but is not limited to, 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). Particularly preferred are organic electroluminescent devices such as OLEDs and OLED field-effect transistors. OLEDs are further particularly preferred. In at least one embodiment, the boron-containing carbazole organic compound of the present application is used in the light-emitting layer of an OLED device.

[0135] In one embodiment, the organic electronic device includes a substrate and, sequentially stacked on the substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode. The light-emitting layer comprises at least one boron-containing carbazole organic compound or mixture as described above, or the light-emitting layer is prepared from the composition as described above. It is understood that the structure of the organic electronic device is not limited to this.

[0136] The substrate may be transparent or opaque. The substrate may be rigid or elastic. The substrate may be plastic, metal, semiconductor wafer or glass. The substrate preferably has a smooth surface, and substrates without surface defects are particularly ideal. In one embodiment, the substrate is flexible, and its material may be selected from but not limited to polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0137] The anode is a hole-injecting electrode, and the anode can easily inject holes into the hole injection layer, the hole transport layer, or the light-emitting layer. The anode may comprise a conductive metal, a conductive metal oxide, or a conductive polymer. In one 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 body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected and used 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. The cathode is an electrode that injects electrons, and the cathode can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer. The cathode may comprise a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or the electron transport layer (ETL) or the 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 for organic electronic devices may be used as cathode materials for the devices according to the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may 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.

[0138] The hole injection layer is a layer for promoting the injection of holes from the anode into the light-emitting layer, and the hole injection material is a material that can skillfully receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0139] The hole transport layer can be used to smoothly transport holes. The hole transport material known in the art for the hole transport layer is suitably a material with high hole mobility, which can receive holes transmitted from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, organic materials based on carbazole, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0140] The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a spiroindoloacridine-based compound or a material known in the art may be used.

[0141] The light-emitting layer can emit red, green, or blue light and can be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region. It is preferably a material with good quantum efficiency for fluorescence or phosphorescence.

[0142] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives or heterocyclic compounds. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but examples thereof are not limited thereto.

[0143] The electron transport layer can be used to smoothly transport electrons. The electron transport material is preferably a material with high electron mobility that can skillfully receive electrons injected from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof may include, but are not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0144] The electron injection layer can be used to smoothly inject electrons. The electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film forming ability. Specific examples include, but are not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0145] It is understood that the organic electronic device may further include a hole blocking layer located between the light-emitting layer and the electron transport layer. The hole blocking layer is a layer that blocks holes from reaching the negative electrode and can generally be formed under the same conditions as those for the hole injection layer. Specific examples include, but are not limited to, diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0146] The light emitting wavelength of the organic electronic device is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0147] In one embodiment, the organic electronic device described in the present application is a solution-type organic electronic device, and one or more functional layers thereof are prepared by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0148] The present invention also relates to applications of the organic electronic device according to the present invention in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0149] The present application also relates to electronic devices comprising the organic electronic device, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0150] The present application will be described in detail below through specific examples. The following examples are only some examples of the present application and are not limitations of the present application. Specific embodiments

[0152] Example 1

[0153] The synthetic route of the boron-containing carbazole organic compound 1 of this embodiment is as follows:

[0154]

[0155] Synthesis of intermediate 1-3:

[0156] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 1-3 with a molar weight of 7.21 mmol, a yield of 72.1%, and MS (ASAP) = 313.5.

[0157] Synthesis of intermediate 1-5:

[0158] Intermediate 1-3 (10 mmol), compound 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was purified by column chromatography to obtain intermediate 1-5 with a molar weight of 6.33 mmol, a yield of 63.3%, and MS (ASAP) = 457.3.

[0159] Synthesis of intermediate 1-7:

[0160] Compound 1-6 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 1-7 with a molar weight of 8.27 mmol and a yield of 82.7%. MS (ASAP) = 273.4.

[0161] Synthesis of intermediate 1-8:

[0162] Intermediate 1-7 (10 mmol), intermediate 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water. The organic phase was purified by column chromatography to obtain intermediate 1-8 with a molar weight of 6.35 mmol and a yield of 63.5%. MS (ASAP) = 694.5.

[0163] Synthesis of boron-containing carbazole organic compound 1: A 250ml three-necked flask was charged with 10mmol of intermediate 1-8 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi (tert-butyl lithium) in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C, and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 1, with a yield of 53.2% and MS (ASAP) = 668.7.

[0164] Example 2

[0165] The synthetic route of the boron-containing carbazole organic compound 2 of this embodiment is as follows:

[0166]

[0167] Synthesis of intermediate 2-2:

[0168] Compound 1-1 (10 mmol), compound 2-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 2-2 with a molar weight of 7.85 mmol and a yield of 78.5%. MS (ASAP) = 299.4.

[0169] Synthesis of intermediate 2-3:

[0170] Intermediate 2-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 2-3 with a molar weight of 5.96 mmol, a yield of 59.6%, and MS (ASAP) = 443.6.

[0171] Synthesis of intermediate 2-4:

[0172] Compound 1-6 (20 mmol), compound 2-1 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 2-4 with a molar weight of 8.17 mmol, a yield of 81.7%, and MS (ASAP) = 259.4.

[0173] Synthesis of intermediate 2-5:

[0174] Intermediate 2-4 (20 mmol), intermediate 2-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 2-5 with a molar weight of 6.24 mmol and a yield of 62.4%. MS (ASAP) = 666.4.

[0175] Synthesis of boron-containing carbazole organic compound 2: A 250ml three-necked flask was charged with 10mmol of intermediate 2-5 and 100ml of dry tert-butylbenzene. Under a nitrogen atmosphere, the mixture was cooled to -30°C and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 2, with a yield of 63.8% and MS (ASAP) = 640.7.

[0176] Example 3

[0177] The synthetic route of the boron-containing carbazole organic compound 3 of this embodiment is as follows:

[0178]

[0179] Synthesis of intermediate 3-2:

[0180] Compound 3-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 3-2 with a molar weight of 7.11 mmol and a yield of 71.1%. MS (ASAP) = 329.4.

[0181] Synthesis of intermediate 3-3:

[0182] Intermediate 3-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 3-3 with a molar weight of 6.87 mmol, a yield of 68.7%, and MS (ASAP) = 473.5.

[0183] Synthesis of intermediate 3-5:

[0184] Compound 3-4 (20 mmol), compound 1-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 3-5 with a molar weight of 6.11 mmol, a yield of 61.1%, and MS (ASAP) = 279.6.

[0185] Synthesis of intermediate 3-6:

[0186] Intermediate 3-5 (20 mmol), intermediate 3-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 3-6 with a molar weight of 7.25 mmol and a yield of 72.5%. MS (ASAP) = 716.4.

[0187] Synthesis of boron-containing carbazole organic compound 3: A 250ml three-necked flask was charged with 10mmol of intermediate 3-6 and 100ml of dry tert-butylbenzene. Under a nitrogen atmosphere, the mixture was cooled to -30°C and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 3, with a yield of 61.5% and MS (ASAP) = 690.5.

[0188] Example 4

[0189] The synthetic route of the boron-containing carbazole organic compound 4 of this embodiment is as follows:

[0190]

[0191] Synthesis of intermediate 4-2:

[0192] Compound 4-1 (10 mmol), compound 2-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 4-2 with a molar weight of 6.59 mmol, a yield of 65.9%, and MS (ASAP) = 315.7.

[0193] Synthesis of intermediate 4-3:

[0194] Intermediate 4-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 4-3 with a molar weight of 5.17 mmol and a yield of 51.7%. MS (ASAP) = 459.3.

[0195] Synthesis of intermediate 4-5:

[0196] Compound 4-4 (20 mmol), compound 2-1 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 4-5 with a molar weight of 6.71 mmol, a yield of 67.1%, and MS (ASAP) = 262.4.

[0197] Synthesis of intermediate 4-6:

[0198] Intermediate 4-5 (20 mmol), intermediate 4-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 4-6 with a molar weight of 7.12 mmol, a yield of 71.2%, and MS (ASAP) = 685.7.

[0199] Synthesis of boron-containing carbazole organic compound 4: A 250ml three-necked flask was charged with 10mmol of intermediate 4-6 and 100ml of dry tert-butylbenzene. Under a nitrogen atmosphere, the mixture was cooled to -30°C and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, boron-containing carbazole organic compound 4, with a yield of 62.5% and MS (ASAP) = 659.5.

[0200] Example 5

[0201] The synthesis route of the boron-containing carbazole organic compound 5 of this embodiment is as follows:

[0202]

[0203]

[0204] Synthesis of intermediate 5-2:

[0205] Compound 3-1 (10 mmol), compound 5-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 5-2 with a molar weight of 6.59 mmol, a yield of 65.9%, and MS (ASAP) = 315.7.

[0206] Synthesis of intermediate 5-3:

[0207] Intermediate 5-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 5-3 with a molar weight of 5.17 mmol and a yield of 51.7%. MS (ASAP) = 459.3.

[0208] Synthesis of intermediate 5-4:

[0209] Compound 5-1 (20 mmol), compound 4-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 5-4 with a molar weight of 6.29 mmol, a yield of 62.9%, and MS (ASAP) = 262.7.

[0210] Synthesis of intermediate 5-5:

[0211] Intermediate 5-4 (20 mmol), intermediate 5-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 5-5 with a molar weight of 7.09 mmol and a yield of 70.9%. MS (ASAP) = 685.4.

[0212] Synthesis of boron-containing carbazole organic compound 5: A 250ml three-necked flask was charged with 10mmol of intermediate 5-5 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 5, with a yield of 62.5% and MS (ASAP) = 659.7.

[0213] Example 6

[0214] The synthesis route of the boron-containing carbazole organic compound 6 of this embodiment is as follows:

[0215]

[0216] Synthesis of intermediate 6-3:

[0217] Compound 6-1 (10 mmol), compound 6-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 6-3 with a molar weight of 7.49 mmol, a yield of 74.9%, and MS (ASAP) = 340.5.

[0218] Synthesis of intermediate 6-4:

[0219] Intermediate 6-3 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 6-4 with a molar weight of 8.25 mmol and a yield of 82.5%. MS (ASAP) = 484.6.

[0220] Synthesis of intermediate 6-6:

[0221] Compound 6-5 (10 mmol), compound 6-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 6-6 with a molar weight of 5.69 mmol, a yield of 56.9%, and MS (ASAP) = 277.3.

[0222] Synthesis of intermediate 6-7:

[0223] Intermediate 6-6 (10 mmol), intermediate 6-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 6-7 with a molar weight of 4.89 mmol and a yield of 48.9%. MS (ASAP) = 725.4.

[0224] Synthesis of boron-containing carbazole organic compound 6: A 250ml three-necked flask was charged with 10mmol of intermediate 6-7 and 100ml of dry tert-butylbenzene. Under a nitrogen atmosphere, the mixture was cooled to -30°C and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, boron-containing carbazole organic compound 6, with a yield of 55.3% and MS (ASAP) = 699.6.

[0225] Example 7

[0226] The synthetic route of the boron-containing carbazole organic compound 7 of this embodiment is as follows:

[0227]

[0228] Synthesis of intermediate 7-3:

[0229] Compound 7-1 (10 mmol), compound 7-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 7-3 with a molar weight of 6.34 mmol and a yield of 63.4%. MS (ASAP) = 388.4.

[0230] Synthesis of intermediate 7-4:

[0231] Intermediate 7-3 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water. The organic phase was purified by column chromatography to obtain intermediate 7-4 with a molar weight of 8.33 mmol and a yield of 83.3%. MS (ASAP) = 532.3.

[0232] Synthesis of intermediate 7-6:

[0233] Compound 7-5 (10 mmol), compound 7-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 7-6 with a molar weight of 8.08 mmol, a yield of 80.8%, and MS (ASAP) = 279.4.

[0234] Synthesis of intermediate 7-7:

[0235] Intermediate 7-6 (10 mmol), intermediate 7-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 7-7 with a molar weight of 5.28 mmol and a yield of 52.8%. MS (ASAP) = 775.4.

[0236] Synthesis of boron-containing carbazole organic compound 7: A 250ml three-necked flask was charged with 10mmol of intermediate 7-7 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, boron-containing carbazole organic compound 7, with a yield of 35.9% and MS (ASAP) = 749.6.

[0237] Example 8

[0238] The synthesis route of the boron-containing carbazole organic compound 8 of this embodiment is as follows:

[0239]

[0240] Synthesis of intermediate 8-2:

[0241] Compound 8-1 (10 mmol), compound 7-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 8-2 with a molar weight of 7.55 mmol and a yield of 75.5%. MS (ASAP) = 399.4.

[0242] Synthesis of intermediate 8-3:

[0243] Intermediate 8-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 8-3 with a molar weight of 8.33 mmol and a yield of 83.3%. MS (ASAP) = 587.3.

[0244] Synthesis of intermediate 8-5:

[0245] Compound 8-4 (10 mmol), compound 7-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 8-5 with a molar weight of 6.57 mmol, a yield of 65.7%, and MS (ASAP) = 279.4.

[0246] Synthesis of intermediate 8-6:

[0247] Intermediate 8-5 (10 mmol), intermediate 8-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 8-6 with a molar weight of 6.01 mmol and a yield of 60.1%. MS (ASAP) = 786.5.

[0248] Synthesis of boron-containing carbazole organic compound 8: A 250 ml three-necked flask was charged with 10 mmol of intermediate 8-6 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21 mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed under reduced pressure. The reaction solution was cooled again to -30°C, and 21 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, boron-containing carbazole organic compound 8, with a yield of 66.2% and MS (ASAP) = 760.7.

[0249] Example 9

[0250] The synthesis route of the boron-containing carbazole organic compound 9 of this embodiment is as follows:

[0251]

[0252] Synthesis of intermediate 9-3:

[0253] Compound 9-1 (10 mmol), compound 9-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 9-3 with a molar weight of 7.22 mmol, a yield of 72.2%, and MS (ASAP) = 381.4.

[0254] Synthesis of intermediate 9-5:

[0255] Intermediate 9-3 (10 mmol), compound 9-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 9-5 with a molar weight of 8.29 mmol and a yield of 82.9%. MS (ASAP) = 539.4.

[0256] Synthesis of intermediate 9-7:

[0257] Compound 9-6 (10 mmol), compound 9-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 9-7 with a molar weight of 6.67 mmol, a yield of 66.7%, and MS (ASAP) = 380.6.

[0258] Synthesis of intermediate 9-8:

[0259] Intermediate 9-7 (10 mmol), intermediate 9-5 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 9-8 with a molar weight of 7.35 mmol and a yield of 73.5%. MS (ASAP) = 883.7.

[0260] Synthesis of boron-containing carbazole organic compound 9: A 250 ml three-necked flask was charged with 10 mmol of intermediate 9-8 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21 mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, boron-containing carbazole organic compound 9, with a yield of 56.8% and MS (ASAP) = 857.2.

[0261] Example 10

[0262] The synthesis route of the boron-containing carbazole organic compound 10 of this embodiment is as follows:

[0263]

[0264] Synthesis of intermediate 10-3:

[0265] Compound 10-1 (10 mmol), compound 10-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 10-3 with a molar weight of 7.05 mmol and a yield of 70.5%. MS (ASAP) = 363.6.

[0266] Synthesis of intermediate 10-4:

[0267] Intermediate 10-3 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 10-4 with a molar weight of 5.86 mmol and a yield of 58.6%. MS (ASAP) = 507.3.

[0268] Synthesis of intermediate 10-6:

[0269] Compound 10-5 (10 mmol), compound 10-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 10-6 with a molar weight of 5.11 mmol, a yield of 51.1%, and MS (ASAP) = 339.4.

[0270] Synthesis of intermediate 10-7:

[0271] Intermediate 10-6 (10 mmol), intermediate 10-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 10-7 with a molar weight of 6.38 mmol, a yield of 63.8%, and MS (ASAP) = 810.5.

[0272] Synthesis of boron-containing carbazole organic compound 10: A 250ml three-necked flask was charged with 10mmol of intermediate 10-7 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 10, with a yield of 24.9% and MS (ASAP) = 784.5.

[0273] Example 11

[0274] The synthesis route of the boron-containing carbazole organic compound 11 of this embodiment is as follows:

[0275]

[0276] Synthesis of intermediate 11-2:

[0277] Compound 11-1 (10 mmol), compound 5-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 11-2 with a molar weight of 7.26 mmol, a yield of 72.6%, and MS (ASAP) = 365.3.

[0278] Synthesis of intermediate 11-3:

[0279] Intermediate 11-2 (10 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 11-3 with a molar weight of 5.29 mmol, a yield of 52.9%, and MS (ASAP) = 509.3.

[0280] Synthesis of intermediate 11-5:

[0281] Compound 11-4 (10 mmol), compound 5-1 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 11-5 with a molar weight of 6.08 mmol, a yield of 60.8%, and MS (ASAP) = 262.3.

[0282] Synthesis of intermediate 11-6:

[0283] Intermediate 11-5 (10 mmol), intermediate 11-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 11-6 with a molar weight of 4.33 mmol, a yield of 43.3%, and MS (ASAP) = 735.5.

[0284] Synthesis of boron-containing carbazole organic compound 11: A 250ml three-necked flask was charged with 10mmol of intermediate 11-6 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then removed under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 11, with a yield of 72.6% and MS (ASAP) = 709.4.

[0285] Example 12

[0286] The synthesis route of the boron-containing carbazole organic compound 12 of this embodiment is as follows:

[0287]

[0288] Synthesis of intermediate 12-2:

[0289] Compound 12-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 12-2 with a molar weight of 7.07 mmol and a yield of 70.7%. MS (ASAP) = 389.4.

[0290] Synthesis of intermediate 12-3:

[0291] Intermediate 12-2 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 12-3 with a molar weight of 6.81 mmol and a yield of 68.1%. MS (ASAP) = 533.4.

[0292] Synthesis of intermediate 12-4:

[0293] Intermediate 12-3 (10 mmol), intermediate 1-7 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 12-4 with a molar weight of 6.38 mmol, a yield of 63.8%, and MS (ASAP) = 770.5.

[0294] Synthesis of boron-containing carbazole organic compound 12: A 250ml three-necked flask was charged with 10mmol of intermediate 12-4 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 12, with a yield of 50.9% and MS (ASAP) = 744.6.

[0295] Example 13

[0296] The synthesis route of the boron-containing carbazole organic compound 13 of this embodiment is as follows:

[0297]

[0298] Synthesis of intermediate 13-2:

[0299] Compound 13-1 (10 mmol), compound 7-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 13-2 with a molar weight of 6.59 mmol and a yield of 65.9%. MS (ASAP) = 383.4.

[0300] Synthesis of intermediate 13-4:

[0301] Intermediate 13-2 (10 mmol), compound 13-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain Intermediate 13-4 with a molar weight of 7.27 mmol and a yield of 72.7%. MS (ASAP) = 583.5.

[0302] Synthesis of intermediate 13-6:

[0303] Compound 13-5 (10 mmol), compound 7-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 13-6 with a molar weight of 5.25 mmol and a yield of 52.5%. MS (ASAP) = 273.4.

[0304] Synthesis of intermediate 13-7:

[0305] Intermediate 13-6 (10 mmol), intermediate 13-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water. The organic phase was purified by column chromatography to obtain intermediate 13-7 with a molar weight of 4.21 mmol and a yield of 42.1%. MS (ASAP) = 820.5.

[0306] Synthesis of boron-containing carbazole organic compound 13: A 250ml three-necked flask was charged with 10mmol of intermediate 13-7 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 13, with a yield of 67.8% and MS (ASAP) = 794.6.

[0307] Example 14

[0308] The synthesis route of the boron-containing carbazole organic compound 14 of this embodiment is as follows:

[0309]

[0310] Synthesis of intermediate 14-2:

[0311] Compound 14-1 (10 mmol), compound 7-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 14-2 with a molar weight of 7.33 mmol and a yield of 73.3%. MS (ASAP) = 383.6.

[0312] Synthesis of intermediate 14-4:

[0313] Intermediate 14-2 (10 mmol), compound 14-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain Intermediate 14-4 with a molar weight of 6.47 mmol, a yield of 64.7%, and MS (ASAP) = 597.5.

[0314] Synthesis of intermediate 14-5:

[0315] Intermediate 14-4 (10 mmol), intermediate 13-6 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water. The organic phase was purified by column chromatography to obtain intermediate 14-5 with a molar weight of 5.22 mmol and a yield of 52.2%. MS (ASAP) = 834.6.

[0316] Synthesis of boron-containing carbazole organic compound 14: A 250ml three-necked flask was charged with 10mmol of intermediate 14-5 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 14, with a yield of 70.6% and MS (ASAP) = 808.7.

[0317] Example 15

[0318] The synthesis route of the boron-containing carbazole organic compound 15 of this embodiment is as follows:

[0319]

[0320] Synthesis of intermediate 15-3:

[0321] Compound 15-1 (10 mmol), compound 15-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 15-3 with a molar weight of 5.46 mmol, a yield of 54.6%, and MS (ASAP) = 397.7.

[0322] Synthesis of intermediate 15-4:

[0323] Intermediate 15-3 (10 mmol), compound 14-3 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 15-4 with a molar weight of 7.18 mmol, a yield of 71.8%, and MS (ASAP) = 611.4.

[0324] Synthesis of intermediate 15-5:

[0325] Compound 13-5 (10 mmol), compound 15-2 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water, and the organic phase was purified by column chromatography to obtain intermediate 15-5 with a molar weight of 5.47 mmol and a yield of 54.7%. MS (ASAP) = 287.3.

[0326] Synthesis of intermediate 15-6:

[0327] Intermediate 15-5 (10 mmol), intermediate 15-4 (10 mmol), Pd-132 (0.1 mmol), S-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted and washed with water. The organic phase was purified by column chromatography to obtain intermediate 15-6 with a molar weight of 3.59 mmol and a yield of 35.9%. MS (ASAP) = 862.6.

[0328] Synthesis of boron-containing carbazole organic compound 15: A 250ml three-necked flask was charged with 10mmol of intermediate 15-6 and 100ml of dry tert-butylbenzene. The mixture was cooled to -30°C under a nitrogen atmosphere, and 21mmol of t-BuLi in n-hexane was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled again to -30°C, and 21mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. The temperature was then raised to 120°C and stirred for 3 hours. The reaction solution was then cooled to room temperature. Aqueous sodium carbonate and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain the crude product, which was then purified on a flash silica gel column to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, namely, the boron-containing carbazole organic compound 15, with a yield of 43.2% and MS (ASAP) = 836.7.

[0329] Comparative Example 1

[0330] The organic compound of this comparative example is comparative compound 1, and the chemical structural formula of comparative compound 1 is shown below.

[0331] Comparative Example 2

[0332] The organic compound of this comparative example is comparative compound 2, and the chemical structural formula of comparative compound 1 is shown below.

[0333]

[0334] The energy levels HOMO, LUMO, T1, and S1 of the boron-containing carbazole organic compounds of Examples 1-15 and the comparative compounds of the comparative examples were obtained by quantum calculation. Specifically, TD-DFT (time-dependent density functional theory) was used with Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110. The molecular geometry was first optimized using the semi-empirical method "GroundState / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). The energy structure of the organic molecule was then calculated using the TD-DFT (time-dependent density functional theory) method using the "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels were calculated according to the following calibration formula, and S1 and T1 were used directly.

[0335] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0336] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385;

[0337] Among them, HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1.

[0338] Table 1:

[0339]

[0340]

[0341] As can be seen from Table 1, the T1 energy level and S1 energy level of the boron-containing carbazole organic compounds 1-15 of Examples 1-15 are significantly higher than that of the comparative compound 1 of the comparative example, which can make the blue light of the boron-containing carbazole organic compounds 1-15 more inclined to deep blue.

[0342] Preparation of OLED devices

[0343] In the blue OLED device of this embodiment, ITO is used as the anode, PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) is used as a hole injection layer material, PVK (Sigma Aldrich, average Mn 25,000-50,000) is used as a hole transport material, BH is used as a host material of the light-emitting material, the boron-containing carbazole organic compounds of Examples 1-15 and the comparative compounds 1 and 2 in the comparative examples are used as guest materials of the light-emitting material, ET and Liq (lithium 8-hydroxyquinoline) are used as electron transport materials, and Al is used as a cathode. The device structure is ITO / PEDOT / PVK / BH:boron-containing carbazole organic compound or comparative compound / ET:Liq / Al.

[0344] The schematic diagram of OLED device is as follows Figure 1 As shown, 10 is a substrate, 20 is an anode, 30 is a hole injection layer, 40 is a hole transport layer, 50 is a light-emitting layer, 60 is an electron transport layer, and 70 is a cathode.

[0345] The chemical structural formulas of BH, ET and Liq are as follows:

[0346]

[0347] The above-mentioned BH, ET, Liq and comparative compound 1 are all commercially available, or their synthesis methods are all prior art.

[0348] The following describes in detail the preparation process of an OLED device using the above materials through specific examples.

[0349] Device Example 1

[0350] The method for preparing an OLED device in this embodiment includes the following steps:

[0351] a. Cleaning of ITO (Indium Tin Oxide) anode layer: Use chloroform, acetone and / or isopropyl alcohol to clean the ITO conductive glass, and then perform UV ozone treatment;

[0352] b. Forming a hole injection layer: Spin-coating the hole injection layer material PEDOT (polyethylene dioxythiophene, Clevios TM AI4083) and treated on a hot plate at 180°C for 10 minutes. The thickness of the hole injection layer was 40 nm.

[0353] c. Forming a hole transport layer: A 5 mg / ml toluene solution of PVK (Sigma Aldrich, average Mn 25,000-50,000) was spin-coated on the hole injection layer and then heated on a hot plate at 180°C for 60 minutes. The thickness of the hole transport layer was 20 nm.

[0354] d. Forming a light-emitting layer: In a nitrogen glove box, spin-coat a light-emitting layer material on the hole transport layer, and then treat on a hot plate at 140° C. for 10 minutes. The host material of the light-emitting layer material is BH, the guest material is the boron-containing carbazole organic compound 1 of Example 1 of the present application, the solvent is methyl benzoate solution, the mass ratio of the host material to the guest material is 95:5, the concentration of the light-emitting layer material is 15 mg / ml, and the thickness of the light-emitting layer is 40 nm.

[0355] e. Forming the electron transport layer: In a vacuum chamber, above the light-emitting layer, ET and Liq are placed in different evaporation units and heated in a high vacuum (1×10 -6 mbar) to co-deposit ET and Liq at a weight ratio of 50:50 to form an electron transport layer with a thickness of 20 nm;

[0356] f. Forming a cathode layer: depositing Al on the electron transport layer to obtain an Al cathode with a thickness of 100 nm;

[0357] g. Packaging: The device was encapsulated with UV-curable resin in a nitrogen glove box.

[0358] Device Examples 2-15

[0359] The device is basically the same as that in device embodiment 1, except that the guest materials of the light-emitting layers of device embodiments 2-15 are selected from the boron-containing carbazole organic compounds of embodiments 2-15, respectively.

[0360] Device Comparison Example 1-2

[0361] The device is basically the same as the device embodiment 1, except that the guest materials of the light-emitting layers of the device comparative examples 1-2 are the comparative compounds 1-2 of the comparative examples, respectively.

[0362] Performance testing and results

[0363] The current-voltage (JV) characteristics of device examples 1-15 and device comparative examples 1-2 were tested using a characterization device, and important parameters such as CIE color coordinates (x, y), voltage @ 1 knits [V], luminous efficiency CE, and lifespan LT90 @ 1000 nits were recorded. The luminous efficiency is the current density of 10 mA / cm 2 The LT90@1000nits lifespan is the time it takes for the device's brightness to drop from an initial brightness of 1000nits to 90% of its initial brightness under constant current. See Table 2 below for test results.

[0364] Table 2:

[0365]

[0366] From Table 2 we can see that:

[0367] Compared with the blue OLED devices of Comparative Examples 1-2, the color coordinates of the blue OLED devices of Examples 1-15 are better.

[0368] Compared to the OLED devices of Comparative Examples 1-2, which had luminous efficiencies of less than 3.5 cd / A and lifetimes of less than 93 hours, the blue OLED devices of Examples 1-15 all had luminous efficiencies ranging from 5.5 to 6.3 cd / A and lifetimes ranging from 139 to 167 hours. This indicates that the blue OLED devices of Examples 1-15 exhibit superior luminous efficiency and lifetime compared to the blue OLED devices of Comparative Examples 1-2.

[0369] Compared with the blue light devices prepared using the comparative compound 1-2 of comparative example 1-2 as the guest material in the light-emitting layer, the lifespan of the blue light devices prepared using the boron-containing carbazole organic compounds 1-15 of examples 1-15 as the guest material in the light-emitting layer is generally improved by 49-106%.

[0370] Furthermore, the blue light-emitting devices fabricated using the boron-containing carbazole organic compounds 1, 2, 12, 13, 14, and 15 as guest materials in the light-emitting layer all exhibited luminous efficiencies ranging from 6.0 to 6.4 cd / A and lifetimes of approximately 160 hours. This is because, compared to the other examples, the introduction of a naphthalene molecule into the boron nitrogen compound enhances the overall molecular conjugation, improving the device's luminous efficiency and lifetime. Furthermore, compared to Comparative Examples 1 and 2, the introduction of tetralin and indane enhances the overall molecular solubility and facilitates compound purification, thereby increasing the purity of the boron-containing carbazole organic compound and, consequently, improving the efficiency and lifetime of the fabricated device.

[0371] The boron-containing carbazole organic compound of the present invention introduces dibenzofuran, dibenzothiophene, carbazole, fluorene, benzopentacyclic ring, and / or naphthalene into the boron-nitrogen compound, enhancing the overall molecular conjugation and improving the device's luminous efficiency and lifespan. Furthermore, the introduction of tetralin and indane improves the overall molecular solubility and facilitates compound purification, thereby increasing the purity of the boron-containing carbazole organic compound and further extending the device's luminous efficiency and lifespan.

[0372] The boron-containing carbazole organic compounds, mixtures, compositions and organic electronic devices provided in the embodiments of the present application are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method and core ideas of the present application. At the same time, for those skilled in the art, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the contents of this specification should not be understood as limiting the present application.

Claims

1. A boron-containing carbazole organic compound, characterized in that: The structure of the boron-containing carbazole organic compound is selected from any one of the following structures: ； in: X and Y are independently selected from O, S, CR8R9 or NR 10 ; R1, R2, R3, R4, R5 each occurrence, are independently selected from: -H, -D, linear alkyl having 1 to 4 C atoms, branched alkyl having 3 to 5 C atoms or phenyl; Each occurrence of R6 and R7 is independently selected from: -H, -D; R8, R9, R 10 Each occurrence is independently selected from: -H, -D, straight-chain alkyl having 1 to 6 C atoms, branched-chain alkyl having 3 to 6 C atoms, or phenyl; n1 is selected from 0 or 1; n2 is selected from 0 or 1; n3 is selected from 0 or 1; n4 is selected from 0 or 1; n5 is selected from 0 or 1; n6 is selected from 0 or 1; n7 is selected from 0 or 1.

2. The boron-containing carbazole organic compound according to claim 1, wherein The boron-containing carbazole organic compound is selected from the following structures: 。 3. A mixture, characterized in that: The mixture comprises the boron-containing carbazole organic compound according to any one of claims 1-2 and at least one organic functional material, wherein the organic functional material is selected from 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 luminescent guest material, a luminescent host material or an organic dye.

4. A composition, characterized in that: The composition comprises the boron-containing carbazole organic compound according to any one of claims 1 to 2 or the mixture according to claim 3, and at least one organic solvent.

5. An organic electronic device comprising at least one organic functional layer, characterized in that: The organic functional layer comprises the boron-containing carbazole organic compound according to any one of claims 1 to 2, or the mixture according to claim 3, or the organic functional layer is prepared from the composition according to claim 4.

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