CN117466920A - Organic compounds for light-emitting devices and their applications, organic electroluminescent devices - Google Patents

Abstract

The present invention provides a boron-containing organic compound, which is characterized in that it has a structure represented by formula (1): The present invention also provides organic light-emitting devices based on the above compounds.

Description

Organic compound for light-emitting device and application thereof, organic electroluminescent device

Technical Field

The present invention relates to a compound for organic electronic devices, and in particular provides a luminescent material for organic electronic devices, wherein the material is suitable as a luminescent material for a thermally activated delayed fluorescence type green light emitting device. The present invention also relates to the application of the material in an organic electroluminescent device.

Background Art

In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates. Beautiful and cool optoelectronic products can be designed and produced according to demand, gaining unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

The core of OLED devices is a thin film structure containing a variety of organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

People have developed a variety of organic materials, combined with various unique device structures, which can improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency, and delay device attenuation. For reasons of quantum mechanics, common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and voids combine to emit light, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously use triplet excitons and singlet excitons to emit light, and are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize luminescent bodies by energy transfer, which can also achieve higher luminescence efficiency. Especially in the field of blue luminescence, which has always been difficult to effectively improve luminescence efficiency, it has a very broad application prospect.

Under the condition of electrical excitation, organic electroluminescent devices will produce 25% singlet and 75% triplet excitons. Traditional fluorescent materials can only use 25% of singlet excitons due to spin prohibition, so the external quantum efficiency is limited to less than 5%. Almost all triplet excitons can only be lost in the form of heat. In order to improve the efficiency of organic electroluminescent devices, triplet excitons must be fully utilized.

To this end, researchers have proposed many methods, the most notable of which is the use of phosphorescent materials. Phosphorescent materials introduce heavy atoms and have a spin-orbit coupling effect, which can fully utilize 75% of triplet excitons and achieve 100% internal quantum efficiency. However, phosphorescent materials use rare heavy metals, which makes the materials expensive and not conducive to cost control. If fluorescent devices can make good use of triplet excitons, this problem can be solved well. Researchers have proposed a method to improve the efficiency of fluorescent devices by quenching triplet excitons to produce singlet excitons in fluorescent devices, but the maximum external quantum efficiency that this method can theoretically achieve is only 62.5%, which is much lower than that of phosphorescent materials. Therefore, it is very necessary to find new technologies to make full use of the triplet energy levels of fluorescent materials to improve luminescence efficiency.

Summary of the invention

In order to solve the above technical problems and provide an organic light-emitting material with more balanced luminous efficiency and life characteristics, especially a compound for a green fluorescent light-emitting device, the present invention provides a boron-containing organic compound, characterized in that it has a structure shown in formula (1):

The dotted line "--" in formula (1) represents that the chemical bond can be a single bond or a double bond.

^X1 and ^X4 are each independently ^CR2 , N or absent, ^X2 and ^X3 are each independently C or N, ^X2 and ^X3 are not C at the same time, ^X5 and ^X6 are C, and the ring formed by ^X1 to ^X6 is an aromatic ring, provided that: when ^X1 is N, ^X2 is C, ^X3 is N, ^X4 is absent, and ^X3 and ^X5 are connected by a single bond, ^X1 and ^X2 are connected by a double bond, and ^X1 and ^X6 are connected by a single bond; when ^X4 is N, ^X3 is C, ^X2 is N, ^X1 is absent, and ^X2 and ^X6 are connected by a single bond, ^X3 and ^X4 are connected by a double bond, and ^X4 and ^X5 are connected by a single bond,

Z and W are each independently selected from at least one of CR ³ R ⁴ , NR ⁵ , O or S;

R ¹ , R ² , R ³ , R ⁴ , and R ⁵ each independently represent any one selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino; wherein R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are optionally connected to adjacent groups or not;

Ring A1 and A2 represent a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring fused to the parent core,

The substitution in the above-mentioned substituted or unsubstituted groups refers to being substituted by a group independently selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C1-C30 alkylsilyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, C6-C30 arylamino or C3-C30 heteroarylamino.

The expression of a ring structure with a “—” through it indicates that the connection site is at any position on the ring structure that can form a bond.

The compound of the present invention has a conjugated structure mother nucleus containing B as shown in the following formula, which is a conjugated mother nucleus containing a boron atom multiple resonance structure.

When two of ^X1 to ^X4 are N atoms, the HOMO energy level of the entire compound is suitable for the device to emit green light. The rigid structure of the entire molecule is increased, the horizontal dipole moment is increased, the light extraction efficiency is improved, and thus the device efficiency is increased. At the same time, the addition of two N atoms is beneficial to increase carrier transport, promote carrier balance, increase device efficiency and increase life. The inventors also tried to replace ^X1 to ^X4 in the parent core with C, and found that the stability of the entire compound molecule was reduced, which was not conducive to extending the life of the device. In addition, a narrow-spectrum green fluorescent luminescent compound could not be provided, that is, the heteroatom combination of BNN in the parent core of the present invention is the key to solving the technical problem of the present invention.

In addition, the inventors found that it is also very important to introduce a five-membered heteroaromatic ring into the boron nitrogen multiple resonance structure (the aromatic ring containing Y in the general formula), which can make the compound have the properties of a conjugated molecule, reduce the triplet energy, increase the energy level difference (ΔE _ST ) between the singlet (S1) and the triplet (T1), and reduce the long-lived triplet exciton in the device. The specific reason is not clear. It is speculated that the HOMO energy level of the parent core structure is suitable for emitting narrow-spectrum red light with high efficiency, making the color unsatisfactory. In short, on the parent core of the compound of the present invention, introducing a five-membered heteroaromatic ring only on one side of the boron nitrogen multiple resonance structure is conducive to providing a.

Among them, based on the mother core of the above five-ring fused system, the present invention can achieve better luminous efficiency. Based on the above technical features, when the compound of the present invention is applied to an organic electroluminescent device, it can effectively adjust and improve the light color and improve the luminous efficiency and life of the device.

It should be noted that, unless otherwise defined below, the meanings of all technical terms and scientific terms used herein are intended to be the same as those generally understood by those skilled in the art. Reference to the technology used herein is intended to refer to the technology generally understood in the art, including those changes in technology or replacement of equivalent technology that are obvious to those skilled in the art. Although it is believed that the following terms are well understood by those skilled in the art, the following definitions are still set forth to better explain the present invention.

In this specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent. When describing C1 to 30, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.

The terms "comprises," "comprising," "having," "containing," or "involving" and other variations thereof herein are inclusive or open-ended and do not exclude additional unrecited elements or method steps.

In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes with the same chemical properties. For example, the expression "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes ¹² C, ¹³ C, etc., which will not be repeated.

The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

As used herein, the terms "heterocyclyl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and/or triple bonds within the ring) cyclic group having at least one ring atom that is a heteroatom selected from N, O and S and the remaining ring atoms being C.

As used herein, the terms "(ylidene)aryl" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "(ylidene)heteroaryl" and "heteroaromatic ring" refer to a monocyclic, bicyclic or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably refers to an alkyl substituted with an aryl or heteroaryl, wherein the aryl, heteroaryl and alkyl are as defined herein.

As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced by a selection from the indicated group, provided that the normal valence of the designated atom in the present context is not exceeded and the substitution forms a stable compound. Combinations of substituents and/or variables are permitted only if such combinations form stable compounds.

If substituents are described as being "independently selected" from a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another (other) substituent.

As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

When a bond to a substituent is shown to pass through a bond connecting two atoms in a ring, then such substituent may be bonded to any ring atom in the substitutable ring.

The term "about" means within ±10% of the stated numerical value, preferably within ±5%, more preferably within ±2%.

In the structural formula disclosed in this specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

The above-mentioned C6-C60 aromatic ring and C3-C60 heteroaromatic ring in the present invention, unless otherwise specified, are aromatic groups satisfying the π conjugated system, including both monocyclic residues and condensed ring residues. The so-called monocyclic residue refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; a condensed ring residue refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing the ring edge, such as naphthyl, anthracenyl, phenanthryl, etc.; a monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a condensed heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or composed of at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

In the present specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, and more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aromatic ring in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl.

In the present specification, the substituted or unsubstituted C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9- The fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl. The C6-C60 aryl group of the present invention can also be a group formed by combining the above groups by single bond connection or/and fusion.

In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, which may be a nitrogen-containing heteroaromatic group, an oxygen-containing heteroaromatic group, a sulfur-containing heteroaromatic group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, Quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2- thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, The heteroaromatic rings may be formed by 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole and the like. Preferred examples of heteroaromatic rings in the present invention include furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and their derivatives, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole.

In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, Quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2- thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole. The C3-C60 heteroaryl group of the present invention may also be a group formed by combining the above groups by single bond connection or/and fusion.

In the present invention, the aryl ether group and heteroaryl ether group include groups formed by the above-mentioned aryl group and heteroaryl group and oxygen. In the present invention, the arylamino group and heteroarylamino group include groups formed by replacing one or two H in the _-NH2 group with the above-mentioned aryl group and heteroaryl group.

In this specification, the chain alkyl group includes both straight-chain and branched alkyl groups. Examples of the C1-C20 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl.

In the present specification, the C3-C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like.

The number of carbon atoms in the C2-C20 straight-chain or cyclic alkenyl group is preferably 2 to 10. Specific examples include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

The number of carbon atoms in the C2-C20 straight-chain or cyclic alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

In the present specification, an alkoxy group refers to a group consisting of the above-mentioned chain alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

Examples of C1-C20 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

In the present specification, examples of C1-C20 silyl groups include silyl groups substituted with the groups listed above for the C1-C20 alkyl groups, i.e., groups formed by replacing one, two or three hydrogen atoms on the silyl group with the above-mentioned chain alkyl or cycloalkyl groups. Specifically, groups include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

As a preferred embodiment of the present invention, the compound of the present invention has a structure represented by formula (1-1) or formula (1-2),

In the formula (1-1) or (1-2), X is CR ² or N; and ring A1, ring A2, W, Y, R ¹ and R ² have the same meanings as in the formula (1).

Based on the above formula (1-1) and formula (1-2), based on the conjugated mother core with a boron atom as the center and containing a X-N-B-Y-W multiple resonance structure, the present invention can provide an organic light-emitting material with more balanced luminous efficiency and life characteristics, especially a compound for a green light fluorescent light-emitting device. It should also be noted that in the mother core structure of formulas (1-1) and (1-2), the three five-membered rings in the fused structure can provide better luminous efficiency. In the comparative test of the embodiment, if the peripheral fused five-membered ring is replaced with a six-membered ring, the luminous efficiency decreases. The reason may be that the rigidity of the molecular structure is enhanced, which is conducive to increasing the light extraction efficiency and the molecular carrier transport is more balanced, which is conducive to improving the life span.

It is further preferred that the compound of the present invention has a structure represented by formula (1-a), (1-b), (1-c) or (1-d),

Here, X, Y, W, ring A1, ring A2, and R ¹ have the same meanings as those expressed above.

In a preferred embodiment of the present method, from the viewpoint of better luminous efficiency, in the above formula, X is N; Y is O or S, preferably S; W is preferably NR ⁵ , O or S, more preferably NR ⁵ ; the addition of S atom can separate the surrounding HOMO and LUMO energy levels through resonance, which is beneficial to improving the luminous efficiency.

R ¹ , R ² , R ³ , R ⁴ , and R ⁵ each independently represent at least one selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; more preferably hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;

Ring A1 and Ring A2 are C6-C30 aromatic rings or C3-C30 heteroaromatic rings fused to the parent nucleus, and the most preferred aromatic rings are benzene rings, pyridine rings or naphthalene rings.

The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by groups independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl.

In a preferred embodiment, the compound of the present invention has a structure represented by formula (1-a-1), (1-b-1), (1-c-1) or (1-d-1):

wherein Z ¹ -Z ⁸ are each independently selected from CR ⁶ or N; R ⁶ is at least one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino; R ⁶ is optionally connected to an adjacent group or not;

X, Y, W, R ¹ , have the same meaning as above,

The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by groups independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl.

In a preferred embodiment of the present invention, ^R6 is at least one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; more preferably, it is hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; more preferably, it is hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; more preferably, at least one of ^Z1 - ^Z8 is ^CR6 and ^R6 is not hydrogen; more preferably, ^R6 is substituted or unsubstituted C1-C10 The chain alkyl group, or a substituted or unsubstituted C6-C30 aryl group, wherein the substitution in the above substituted or unsubstituted groups refers to substitution with a group independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl.

In a preferred embodiment of the present invention, the compound of the present invention has a structure represented by formula (1) or (1-1) by formula (1-a-2), (1-b-2), (1-c-2) or (1-d-2):

Wherein, X, Y, R ¹ , R ² , R ³ , R ⁴ , and R ⁵ have the same meanings as above; Z ⁹ -Z ¹³ are each independently selected from CR ⁶ or N, the definition of R ⁶ ; R ⁶ is optionally connected to an adjacent group or not; preferably, at least one R ⁶ in Z ⁹ -Z ¹³ is not hydrogen, and more preferably R ⁶ is substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by a group independently selected from halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, or a combination of at least two or more groups.

More preferably, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in the present invention are each independently selected from hydrogen, C1-C6 chain alkyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, furyl, thienyl, diphenylamino and cumyl.

Specific examples of the compounds of the present invention include the following compounds, but are not limited to these compounds:

The compound of the present invention also has high fluorescence quantum efficiency. When used as an OLED light-emitting layer material, the light-emitting efficiency and life of the device can be significantly improved.

In another aspect of the present invention, based on the above light-emitting materials, the present invention can provide an organic electroluminescent device, comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, characterized in that the organic layer contains the compound of the present invention.

In a preferred embodiment of the present invention, at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains the compound of the present invention.

In a preferred embodiment of the present invention, the compound of the present invention is used as a doping material doped into a host material, and the doping mass concentration is 0.1-10wt%.

In a preferred embodiment of the present invention, the light-emitting layer, in addition to containing the compound of the present invention as a doping material, also includes a host material and a sensitizer material, wherein the host material is a single P-type host material, an N-type host material, a single molecule excited complex host material, or a mixture of two host materials, and the sensitizer material is a thermally activated delayed fluorescence material, or a phosphorescent material, or a mixture of a thermally activated delayed fluorescence material and a phosphorescent material.

At this time, it is preferred that the maximum emission wavelength of the sensitizer material is smaller than the maximum emission wavelength of the compound of the present invention as a doping material, so that the light-emitting device can obtain better performance.

The above-mentioned compound of the present invention has excellent luminescent properties, can provide triplet excitons to achieve higher luminescent efficiency, and is suitable for use as a luminescent dye, especially as a green luminescent dye, based on its excellent carrier transfer efficiency. Of course, since the compound of the present invention can also be used as a sensitizer together with the host material and the dye to achieve a good luminescent layer. The devices used include but are not limited to organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.

The present invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains at least one compound described in the present invention.

The structure of the organic electroluminescent device of the present invention is consistent with that of existing devices, for example, it includes an anode layer, multiple light-emitting functional layers and a cathode layer; the multiple light-emitting functional layers at least include a light-emitting layer, wherein the light-emitting layer contains the above-mentioned organic compound of the present invention.

The present invention further discloses a display screen or a display panel, wherein the organic electroluminescent device as described above is adopted in the display screen or the display panel; preferably, the display screen or the display panel is an OLED display.

The present invention also discloses an electronic device, wherein the electronic device has a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device as described above.

The OLED device prepared by using the compound of the present invention has high luminous efficiency and better service life, especially can adjust the light color of green light dye to achieve the light color required for mass production, and can meet the requirements of current panel and display manufacturers for high-performance materials.

In addition, the inventors tried the following compound D-1 which is different from the parent core of the compound of the present invention:

For D-1, Gaussian program software Gaussian is used to calculate by density functional method, wherein density functional theory is a method for studying the electronic structure of multi-electron system, which is well known to those skilled in the art and will not be repeated here. The calculation results show that the light color of D-1 is blue light. It is speculated that it is due to the weakening of single heteroatom N and S compared with double N atoms, and the electronic energy level is higher than double N atoms, thereby causing the luminescence to be more blue-shifted than double N atoms, resulting in the inability to achieve green luminescence. From this aspect, the parent core structure of the present invention is crucial for solving the technical problems to be solved by the present invention.

DETAILED DESCRIPTION

The technical solution of the present invention is further described in more detail below. It should be understood by those skilled in the art that the specific implementation methods and examples are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

The process of obtaining the compound of the present invention is as follows:

The compounds of the present invention can be obtained by known methods, for example, by known organic synthesis methods. The following is an exemplary synthesis route of the compound represented by formula (1-1) or (1-2), which can be extended to the synthesis method of the compound represented by formula (1), but can also be obtained by other known methods by those skilled in the art. The representative synthesis route of the compound represented by the general formula of the present invention is as follows:

Under the above general route, the compounds of the present invention can be synthesized by replacing different raw materials. However, the compounds of the present invention are not limited to the above synthesis methods, and those skilled in the art can select other synthesis methods as needed based on existing known technologies.

Device Implementation Method

The organic light emitting device (OLED) of the present invention, except that the light emitting layer contains the above-mentioned compound of the present invention, other elements can be made by the existing technology. Specifically, the OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate)

(PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below; or any combination thereof.

The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent materials, etc. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

In one aspect of the present invention, the barrier layer surrounding the light-emitting layer may be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

The device may further include an electron injection layer located between the electron transport layer and the cathode. Materials for the electron injection layer include, but are not limited to, one or more combinations of the following.

LiQ, LiF, NaCl, CsF, Li ₂ O, Cs ₂ CO ₃ , BaO, Na, Li, Ca, Yb, Mg.

Example

The organic compounds of the present invention were synthesized representatively, and applied together with corresponding comparative compounds in organic electroluminescent devices to test the device performance under the same conditions.

Synthesis Example

The specific preparation method of the above-mentioned new compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples. It should be noted that obtaining the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the compound proposed by the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained from commercial channels, or are made by themselves according to known methods through these raw materials. The solvents and reagents used in the present invention, such as dichloromethane, petroleum ether, ethanol, tert-butylbenzene, boron tribromide, carbazole, diphenylamine, and other chemical reagents, can all be purchased from the domestic chemical product market, such as purchased from Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc. The analysis and detection of the intermediates and compounds in the present invention uses an ABSCIEX mass spectrometer (4000QTRAP).

Synthesis Example 1: Synthesis of S1:

Synthesis of intermediate M1-1:

At room temperature, raw material A (150 g), raw material B (54.49 g), Pd (dppf) 2 Cl 2 (7.72 g), sodium tert-butoxide (76.68 g), toluene (500 ml) as solvent were added to a 2L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 80°C overnight. After the reaction solution was cooled, it was subjected to rapid column chromatography in a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 130 g of white solid M1-1, with a yield of 86.3%. The molecular ion mass determined by mass spectrometry was 293.12 (theoretical value: 293.07).

Synthesis of intermediate M1-2

At room temperature, add M1-1 (130 g), Boc2O (115.72 g), 4-dimethylaminopyridine (26.99 g), 1,4-dioxane (300 ml) as solvent to a 1000 ml single-mouth bottle, and reflux for 3 h. Concentrate, dissolve in dichloromethane (300 ml), and wash three times with anhydrous sodium carbonate aqueous solution (30 ml). Separate, dry over anhydrous sodium sulfate, and concentrate to obtain 165.52 g of white solid M1-2, with a yield of 95%. The molecular ion mass determined by mass spectrometry is 393.18 (theoretical value: 393.13).

Synthesis of intermediate M1-3

At room temperature, M1-2 (165.00 g), benzimidazole (54.38 g), Pd2dba3 (7.66 g1), tri-tert-butylphosphine tetrafluoroborate (4.86 g), sodium tert-butoxide (60.32 g), toluene (300 ml) as solvent were added to a 1000 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. After standing at room temperature, the reaction solution was poured into a silica gel column filled with silica gel, dichloromethane was used as an eluent, and rapid column chromatography was performed, concentrated, and washed with ethanol to obtain 159.34 g of white solid M1-3, with a yield of 80%. The molecular ion mass determined by mass spectrometry was 475.31 (theoretical value: 475.20).

Synthesis of intermediate M1-4

At room temperature, M1-3 (159 g) was added to a 1000 ml single-mouth bottle, 1,4-dioxane (300 ml) was used as solvent, concentrated hydrochloric acid (50 ml) was added, and the mixture was heated to 100 ° C for reflux reaction overnight. The mixture was cooled to room temperature, concentrated, and dissolved in dichloromethane, washed three times with water, washed once with sodium carbonate aqueous solution, and the organic phase was dried over anhydrous sodium sulfate. The solvent was spin-dried to obtain 125.56 g of white solid M1-4, with a yield of 100%. The molecular ion mass determined by mass spectrometry was 375.22 (theoretical value: 375.15).

Synthesis of intermediate M1-5

At room temperature, M1-4 (20 g), raw material D (15.76 g), Pd2dba3 (0.97 g), tri-tert-butylphosphine tetrafluoroborate (0.62 g), sodium tert-butoxide (7.67 g), toluene (100 ml) as solvent, replace nitrogen three times, and react at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 19.51 g of white solid, yield 65%. Molecular ion mass determined by mass spectrometry: 563.31 (theoretical value: 563.22).

Synthesis of final product S1

At room temperature, add M1-5 (19g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (31.57ml, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (4.7ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (11.76ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), recrystallize the crude product from toluene/ethanol twice to obtain 5.43g of the sample before sublimation, with a yield of 30%. The molecular ion mass determined by mass spectrometry was: 537.32 (theoretical value: 537.24).

Synthesis Example 2: Synthesis of S2:

Synthesis of intermediate M2-1

At room temperature, M1-4 (20 g), raw material E (15.76 g), Pd2dba3 (0.97 g), tri-tert-butylphosphine tetrafluoroborate (0.62 g l), sodium tert-butoxide (7.67 g), toluene (100 ml) as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 21.01 g of white solid M2-1, yield 70%. The molecular ion mass determined by mass spectrometry is: 563.34 (theoretical value: 563.22).

Synthesis of final product S2

At room temperature, add M2-1 (20g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (33.23ml, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (4.95ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (12.38ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 6.1g of the sample before sublimation, with a yield of 32%. The molecular ion mass determined by mass spectrometry was: 537.27 (theoretical value: 537.24).

Synthesis Example 3: Synthesis of S3:

Synthesis of intermediate M3-1

At room temperature, M1-4 (20 g), raw material F (15.76 g), Pd2dba3 (0.97 g), tri-tert-butylphosphine tetrafluoroborate (0.62 g), sodium tert-butoxide (7.67 g), toluene (100 ml) as solvent, replace nitrogen three times, and react at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 18.61 g of white solid M3-1, yield 62%. Molecular ion mass determined by mass spectrometry: 563.27 (theoretical value: 563.22).

Synthesis of final product S3

At room temperature, add M3-1 (18.6g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (30.91ml, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (4.61ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (11.52ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 4.96g of the sample before sublimation, with a yield of 28%. The molecular ion mass determined by mass spectrometry was: 537.33 (theoretical value: 537.24).

Synthesis Example 4: Synthesis of S4:

Synthesis of intermediate M4-1

At room temperature, M1-4 (20 g), raw material G (15.76 g), Pd2dba3 (0.97 g), tri-tert-butylphosphine tetrafluoroborate (0.62 g, 2.13 mmol), sodium tert-butoxide (7.67 g), toluene (100 ml) as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 19.51 g of white solid M4-1, yield 65%. The molecular ion mass determined by mass spectrometry is: 563.34 (theoretical value: 563.22).

Synthesis of final product S4

At room temperature, add M4-1 (19.5g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (32.4ml1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (4.83ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (12.07ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 5.61g of the sample before sublimation, with a yield of 30.2%. The molecular ion mass determined by mass spectrometry was: 537.26 (theoretical value: 537.24).

Synthesis Example 5: Synthesis of S12

Synthesis of intermediate M4-1

At room temperature, M1-4 (15 g), raw material H (12.69 g), Pd2dba3 (0.73 g), tri-tert-butylphosphine tetrafluoroborate (0.46 g), sodium tert-butoxide (5.75 g), toluene (100 ml) as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. It was allowed to stand at room temperature, filtered, and the filtrate was mixed with silica gel for concentration, column chromatography (PE: DCM = 30: 1), and toluene/ethanol recrystallization to obtain 14.69 g of white solid M12-1, with a yield of 63%. The molecular ion mass determined by mass spectrometry analysis was 583.21 (theoretical value: 583.18).

Synthesis of final product S12

At room temperature, add M12-1 (14.69g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (23.57ml) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (3.51ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (8.78ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 4.91g of the sample before sublimation, with a yield of 35%. The molecular ion mass determined by mass spectrometry was: 557.34 (theoretical value: 557.21).

Synthesis Example 6: Synthesis of S13

Synthesis of intermediate M12-1

At room temperature, M1-4 (15 g), raw material I (12.69 g), Pd2dba3 (0.73 g), tri-tert-butylphosphine tetrafluoroborate (0.46 gl), sodium tert-butoxide (5.75 g), toluene (100 ml) as solvent, replace nitrogen three times, and react at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 15.85 g white solid M13-1, yield 68%. Molecular ion mass determined by mass spectrometry: 583.23 (theoretical value: 583.18).

Synthesis of final product S13

At room temperature, add M13-1 (15.85g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (25.44ml1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (3.79ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (9.48ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 4.69g of the sample before sublimation, with a yield of 31%. The molecular ion mass determined by mass spectrometry was: 557.31 (theoretical value: 557.21).

Synthesis Example 7: Synthesis of S6:

Synthesis of intermediate M6-1

At room temperature, M1-2 (150.00 g), 6-phenylbenzimidazole (81.27 g), Pd2dba3 (6.97 g, 7.61 mmol), tri-tert-butylphosphine tetrafluoroborate (4.41 g), sodium tert-butoxide (54.84 g), toluene (300 ml) as solvent were added to a 1000 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. After standing at room temperature, the reaction solution was poured into a silica gel column filled with silica gel, dichloromethane was used as an eluent, and rapid column chromatography was performed, concentrated, and washed with ethanol to obtain 157.51 g of white solid M6-1, with a yield of 75%. The molecular ion mass determined by mass spectrometry was: 551.35 (theoretical value: 551.23).

Synthesis of intermediate M6-2

At room temperature, M6-1 (157.51 g) was added to a 1000 ml single-mouth bottle, 1,4-dioxane (300 ml) was used as solvent, concentrated hydrochloric acid (50 ml) was added, and the mixture was heated to 100 °C for reflux reaction overnight. The mixture was cooled to room temperature, concentrated, and dissolved in dichloromethane, washed three times with water, washed once with sodium carbonate aqueous solution, the organic phase was dried over anhydrous sodium sulfate, and the solvent was dried to obtain 122.5 g of white solid M6-2, with a yield of 95%. The molecular ion mass determined by mass spectrometry was 451.23 (theoretical value: 451.18).

Synthesis of intermediate M6-3

At room temperature, M6-2 (15 g), raw material K (9.83 g), Pd2dba3 (0.61 g), tri-tert-butylphosphine tetrafluoroborate (0.39 g), sodium tert-butoxide (4.78 g), toluene (100 ml) as solvent, replace nitrogen three times, and react at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 13.81 g white solid M6-3, yield 65%. Molecular ion mass determined by mass spectrometry: 639.32 (theoretical value: 639.25).

Synthesis of final product S6

At room temperature, add M6-3 (13.81g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (20.22ml) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (3.01ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (7.53ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 3.9g of the sample before sublimation, with a yield of 29.5%. The molecular ion mass determined by mass spectrometry was: 613.33 (theoretical value: 613.27).

Synthesis Example 8: Synthesis of S7:

Synthesis of intermediate M7-1

At room temperature, M6-2 (15 g), raw material L (9.83 g), Pd2dba3 (0.61 g), tri-tert-butylphosphine tetrafluoroborate (0.39 g), sodium tert-butoxide (4.78 g), toluene (100 ml) as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. It was allowed to stand at room temperature, filtered, and the filtrate was mixed with silica gel for concentration, column chromatography (PE: DCM = 30: 1), and toluene/ethanol recrystallization was performed to obtain 13.28 g of white solid M7-1, with a yield of 62.5%. The molecular ion mass determined by mass spectrometry analysis was 639.28 (theoretical value: 639.25).

Synthesis of final product S7

At room temperature, add M7-1 (13.28g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (19.44ml, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.9ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (7.25ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 4.07g of the sample before sublimation, with a yield of 32%. The molecular ion mass determined by mass spectrometry was: 613.35 (theoretical value: 613.27).

Synthesis Example 9: Synthesis of S10:

Synthesis of intermediate M10-1

At room temperature, M6-2 (15 g), raw material M (10.56 g), Pd2dba3 (0.61 g), tri-tert-butylphosphine tetrafluoroborate (0.39 g), sodium tert-butoxide (4.78 g), toluene (100 ml) as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. It was allowed to stand at room temperature, filtered, and the filtrate was mixed with silica gel for concentration, column chromatography (PE: DCM = 30: 1), and toluene/ethanol recrystallization to obtain 14.9 g of white solid M10-1, with a yield of 68%. The molecular ion mass determined by mass spectrometry analysis was 659.33 (theoretical value: 659.22).

Synthesis of final product S10

At room temperature, add M10-1 (14.9 g) and xylene (100 ml) to a 500 ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (21.16 ml, 1.6 M) to the system at -70 ° C, stir at room temperature for 5 min, heat to 60 ° C and react for 2 h, the system changes from anhydrous clear to dark red. Add boron tribromide (3.15 ml) to the system at -40 ° C, stir at room temperature for 1 h, the system changes from white turbid to red solution. Then add N, N-diisopropylethylamine (7.88 ml) at -40 ° C, heat to 120 ° C and react overnight. The system is cooled to room temperature, dichloromethane (100 ml) is added and mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and the crude product is recrystallized twice from toluene/ethanol to obtain 4.15 g of the sample before sublimation, with a yield of 29%. The molecular ion mass determined by mass spectrometry was: 633.27 (theoretical value: 633.24).

Synthesis Example 10: Synthesis of S11:

Synthesis of intermediate M11-1

At room temperature, M6-2 (15 g), raw material N (10.56 g), Pd2dba3 (0.61 g), tri-tert-butylphosphine tetrafluoroborate (0.39 g, 1.33 mmol), sodium tert-butoxide (4.78 g), toluene (100 ml) as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. Stand at room temperature, filter, mix the filtrate with silica gel, concentrate, column chromatography (PE: DCM = 30: 1), toluene / ethanol recrystallization to obtain 13.15 g of white solid M11-1, yield 60%. The molecular ion mass determined by mass spectrometry is: 659.29 (theoretical value: 659.22).

Synthesis of final product S11

At room temperature, add M11-1 (13.15g) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (18.67ml, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.78ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (6.96ml) at -40℃, heat to 120℃ and react overnight. Cool the system to room temperature, add dichloromethane (100ml) and mix with silica gel to concentrate, column chromatography (PE:DCM=20:1), and recrystallize the crude product from toluene/ethanol twice to obtain 3.91g of the sample before sublimation, with a yield of 31%. The molecular ion mass determined by mass spectrometry was: 633.30 (theoretical value: 633.24).

Device Embodiment

The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

The glass substrate with the anode is placed in a vacuum chamber, and the vacuum is evacuated to <1×10-5Pa. On the anode layer, 10nm of HT-4:HI-3 (97/3, w/w) mixture is vacuum-evaporated in sequence as a hole injection layer, 60nm of compound HT-4 as a hole transport layer, 5nm of compound HT-14 as an electron blocking layer; 20nm of compound BFH-4:S1 (100:3, w/w) binary mixture as a light-emitting layer; 5nm of ET-23 as a hole blocking layer, 25nm of compound ET-69:ET-57 (50/50, w/w) mixture as an electron transport layer, 1nm of LiF as an electron injection layer, and 150nm of metal aluminum as a cathode. The total evaporation rate of all organic layers and LiF is controlled at 0.1nm/sec, and the evaporation rate of the metal electrode is controlled at 1nm/sec.

The manufacturing process of device examples 2-10 and comparative examples 1-3 is the same as that of device example 1, except that dye S1 is replaced by the compounds listed in Table 1 and R-1 to R-3, respectively.

Among them, Ref-1 and Ref-2 refer to the synthesis method in CN114144420A; Ref-3 refers to the synthesis method in CN111253421A; the above synthesis methods are not repeated here.

The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

At the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Examples 1 to 3 and the life of the devices were measured using a digital source meter and PR650. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage when the brightness of the organic electroluminescent device reached 1000 cd/m ² was measured as the driving voltage at the corresponding brightness. At the same time, the external quantum efficiency (EQE%) of the device can be directly measured on the PR650;

The performance of the organic electroluminescent devices prepared by the above device examples 1 to 10 and device comparative examples 1 to 3 is shown in Table 1 below.

Table 1

The devices in the embodiments are all high-efficiency green fluorescent light-emitting elements, while Comparative Example 3 cannot achieve qualified green light emission and emits blue light, so the data in the above table is "-".

The above results show that the novel compounds of the present invention have better performance in organic electroluminescent devices. Compared with R-1 and R-2, in the compounds of the present invention in Examples 1-10, the thiophene ring is connected to the boron atom on one side of the parent core, and the thiophene ring has a resonance effect and can make the carrier transmission more balanced. Therefore, the device in the example can achieve a lower operating voltage and a higher external quantum efficiency.

The present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above-mentioned embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements. The attached claims summarize the scope of the present invention. The equivalent replacement of the raw materials of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims (14)

1. A boron-containing organic compound, characterized in that it has a structure shown in formula (1): The dotted line "--" in formula (1) represents that the chemical bond can be a single bond or a double bond. ^X1 and ^X4 are each independently ^CR2 , N or absent, ^X2 and ^X3 are each independently C or N, ^X2 and ^X3 are not C at the same time, ^X5 and ^X6 are C, and the ring formed by ^X1 to ^X6 is an aromatic ring, provided that: when ^X1 is N, ^X2 is C, ^X3 is N, ^X4 is absent, and ^X3 and ^X5 are connected by a single bond, ^X1 and ^X2 are connected by a double bond, and ^X1 and ^X6 are connected by a single bond; when ^X4 is N, ^X3 is C, ^X2 is N, ^X1 is absent, and ^X2 and ^X6 are connected by a single bond, ^X3 and ^X4 are connected by a double bond, and ^X4 and ^X5 are connected by a single bond, Y and W are each independently selected from at least one of CR ³ R ⁴ , NR ⁵ , O or S; R ¹ , R ² , R ³ , R ⁴ , and R ⁵ each independently represent any one selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino; wherein R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are optionally connected to adjacent groups or not; Ring A1 and A2 represent a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring fused to the parent core, The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by a group independently selected from halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C1-C30 alkylsilyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, C6-C30 arylamino or C3-C30 heteroarylamino, or a combination of at least two or more groups. The expression of a ring structure with a “—” through it indicates that the connection site is at any position on the ring structure that can form a bond. 2. The boron-containing organic compound according to claim 1, characterized in that the compound has a structure shown in formula (1-1) or formula (1-2), In formula (1-1) or (1-2), X is CR ² or N; Ring A1, ring A2, W, Y, R ¹ and R ² have the same meanings as in claim 1. 3. The boron-containing organic compound according to claim 2, characterized in that the compound has a structure represented by formula (1-a), (1-b), (1-c) or (1-d), Here, X, Y, W, ring A1, ring A2, and R ¹ have the same meanings as those in claim 2. 4. The boron-containing organic compound according to claim 2, characterized in that X is N; Y is O or S, preferably S; W is NR ⁵ , O or S, preferably NR ⁵ ; R ¹ , R ² , R ³ , R ⁴ , and R ⁵ each independently represent at least one selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; more preferably, hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; Ring A1 and Ring A2 are C6-C30 aromatic rings or C3-C30 heteroaromatic rings fused to the parent nucleus, preferably benzene rings, pyridine rings or naphthalene rings, The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by a group independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl. The expression of a ring structure with a “—” through it indicates that the connection site is at any position on the ring structure that can form a bond. 5. The boron-containing organic compound according to claim 2, wherein the compound has a structure represented by formula (1-a-1), (1-b-1), (1-c-1) or (1-d-1): wherein Z ¹ -Z ⁸ are each independently selected from CR ⁶ or N; R ⁶ is at least one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino; R ⁶ is optionally connected to an adjacent group or not; X, Y, W, R ¹ have the same meanings as those in claim 2. The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by a group independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl. 6. The boron-containing organic compound according to claim 5, wherein ^R6 is at least one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; more preferably hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; more preferably hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; More preferably, at least one of Z ¹ -Z ⁸ is CR ⁶ and R ⁶ is not hydrogen; further more preferably, R ⁶ is a substituted or unsubstituted C1-C10 chain alkyl group, or a substituted or unsubstituted C6-C30 aryl group, The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by a group independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl. 7. The boron-containing organic compound according to claim 5, wherein the compound has a structure represented by formula (1) or (1-1) by formula (1-a-2), (1-b-2), (1-c-2) or (1-d-2): Wherein, X, Y, R ¹ , R ² , R ³ , R ⁴ , and R ⁵ have the same meanings as in claim 2; Z ⁹ -Z ¹³ are each independently selected from CR ⁶ or N, R ⁶ is as defined in formula (1-a-1); R ⁶ is optionally connected to an adjacent group or not; Preferably, at least one R ⁶ in Z ⁹ -Z ¹³ is not hydrogen, more preferably R ⁶ is a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group; The substitution in the above-mentioned substituted or unsubstituted groups refers to substitution by a group independently selected from one or a combination of at least two of halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl. 8. The boron-containing organic compound according to any one of claims 5 to 7, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently selected from hydrogen, C1-C6 chain alkyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, furyl, thienyl, diphenylamino and cumyl. 9. The boron-containing organic compound according to claim 1, characterized in that the structure represented by formula (1) is the compound structure shown below: 10. An organic electroluminescent material, which is the compound according to any one of claims 1 to 9; Preferably, the luminescent material is a green light luminescent material; preferably, the luminescent material is applied to a fluorescent organic light emitting device; further preferably, the organic light emitting device is a thermally activated delayed fluorescence light emitting device. 11. Use of the compound according to any one of claims 1 to 9 as a functional material in an organic electronic device, wherein the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper. 12. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1 to 9. 13. The organic electroluminescent device according to claim 12, characterized in that the light-emitting layer contains, in addition to the compound according to any one of claims 1 to 9 as a doping material, a host material and a sensitizer material; The host material is a single P-type host material, an N-type host material, a single molecule exciplex host material, or a mixture of two host materials. The sensitizer material is a thermally activated delayed fluorescent material, or a phosphorescent material, or a mixture of a thermally activated delayed fluorescent material and a phosphorescent material. 14 . The organic electroluminescent device according to claim 12 , wherein the maximum emission wavelength of the sensitizer material is smaller than the maximum emission wavelength of the compound according to any one of claims 1 to 9 as a doping material.