CN117466920A

CN117466920A - Organic compound for light-emitting device, application of organic compound and organic electroluminescent device

Info

Publication number: CN117466920A
Application number: CN202210844232.XA
Authority: CN
Inventors: 孙磊; 李熠烺; 李国孟; 曾礼昌
Original assignee: Hefei Dingcai Technology Co ltd
Current assignee: Hefei Dingcai Technology Co ltd
Priority date: 2022-07-18
Filing date: 2022-07-18
Publication date: 2024-01-30

Abstract

The invention provides a boron-containing organic compound, which is characterized by having a structure shown in a formula (1):

Description

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

Technical Field

The invention relates to a compound for an organic electronic device, in particular to a luminescent material for an organic electronic device, which is suitable for being used as a luminescent material of a heat-activated delayed fluorescence type green light luminescent device. The invention also relates to application of the material in an organic electroluminescent device.

Background

Optoelectronic devices based on organic materials have become increasingly popular in recent years. The inherent flexibility of organic materials makes them very suitable for fabrication on flexible substrates, which can be designed to produce aesthetically pleasing and cool optoelectronic products, as desired, with no comparable 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, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like.

The OLED device core is a thin film structure containing a plurality of organic functional materials. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.

Various organic materials have been developed, and various peculiar device structures are combined, so that carrier mobility can be improved, carrier balance can be regulated, electroluminescent efficiency can be broken through, and device attenuation can be delayed. For quantum mechanical reasons, common fluorescent emitters emit light mainly by singlet excitons generated when electrons and air are combined, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property to sensitize the luminophor by means of energy transfer, and can also realize higher luminous efficiency. Especially in the blue light-emitting field which is difficult to effectively improve the light-emitting efficiency, the fluorescent lamp has very wide application prospect.

Under the condition of electro-excitation, the organic electroluminescent device can generate 25% of singlet state and 75% of triplet state excitons. The conventional fluorescent material can only utilize 25 singlet excitons due to spin inhibition, so that the external quantum efficiency is limited to within 5%. Almost all triplet excitons can only be lost by thermal means. In order to improve the efficiency of the organic electroluminescent device, triplet excitons must be fully utilized.

For this reason, researchers have proposed many methods, most notably using phosphorescent materials. The phosphorescent material introduces heavy atoms, has spin-orbit coupling effect, and can fully utilize 75% of triplet excitons to realize 100% of internal quantum efficiency. However, phosphorescent materials are expensive due to the use of rare heavy metals, which is disadvantageous in cost control. This problem can be well solved if the fluorescent device can well utilize triplet excitons. Researchers have proposed methods for increasing the efficiency of fluorescent devices by quenching triplet excitons to generate singlet excitons in fluorescent devices, but the maximum external quantum efficiency theoretically achievable by this method is only 62.5%, far below that of phosphorescent materials. It is therefore necessary to find new technologies to fully exploit the triplet energy level of fluorescent materials to increase the luminous efficiency.

Disclosure of Invention

In order to solve the above technical problems, the present invention provides a boron-containing organic compound, which is characterized in that it has a structure represented by formula (1):

the dotted line "-" in formula (1) represents that the chemical bond may be a single bond or a double bond,

X ¹ 、X ⁴ each independently is CR ² N or not, X ² 、X ³ Each independently is C or N, X ² And X ³ Not simultaneously C, X ⁵ And X ⁶ C is represented by X ¹ ～X ⁶ The ring is aromatic, provided that: when X is ¹ When N is N, X ² Is C, X ³ Is N, X ⁴ Is absent and X ³ And X ⁵ Is connected with each other by a single bond, X ¹ And X ² Is connected by double bond, X ¹ And X ⁶ The two are connected by a single bond; when X is ⁴ When N is N, X ³ Is C, X ² Is N, X ¹ Is absent and X ² And X ⁶ Is connected with each other by a single bond, X ³ And X ⁴ Is connected by double bond, X ⁴ And X ⁵ Is connected with each other by a single bond,

z, W are each independently selected from CR ³ R ⁴ 、NR ⁵ At least one of O or S;

R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ each independently represents any one selected from hydrogen, halogen, cyano, nitro, hydroxy, 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 is ¹ 、R ² 、R ³ 、 R ⁴ 、R ⁵ Optionally with or without an adjacent group;

the rings A1, A2 represent C6-C60 aromatic rings or C3-C60 heteroaromatic rings fused to the parent nucleus,

the above-mentioned substituted or unsubstituted each group means that each group is independently substituted with one or more groups selected from halogen, cyano, nitro, hydroxy, 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 "ring structure" indicates that the linking site is located at any position on the ring structure that is capable of bonding.

The compound of the invention has a conjugated structure parent nucleus containing B shown in the following formula, is a conjugated parent nucleus containing boron atom multiple resonance structure,

when X is ¹ ～X ⁴ The HOMO level of the entire compound is suitable for green emission by the device when two of (a) are N atoms. The rigidity structure of the whole molecule is increased, the horizontal dipole moment is increased, and the light extraction efficiency is improved, so that the device efficiency is increased. Meanwhile, the addition of two N atoms is beneficial to increasing carrier transmission, promoting carrier balance, increasing device efficiency and prolonging service life. The inventors also tried replacement, X in the parent core ¹ ～X ⁴ When both are C, the stability of the whole compound molecule is reduced, the service life of the device is not prolonged, and in addition, a narrow-spectrum green light fluorescent compound cannot be provided, namely, a B-N-N heteroatom combination mode in the parent nucleus is a key for solving the technical problem of the invention.

In addition, the inventors found that the introduction of a five-membered heteroaromatic ring (containing an aromatic ring of Y in the formula) into the boron-nitrogen multiple resonance structure is also very important, and that it is possible to impart the compound with conjugated molecular properties, reduce triplet energy, and increase the energy level difference (. DELTA.E) between the singlet state (S1) and the triplet state (T1) _ST ) The specific reason for reducing the long lifetime triplet excitons in devices is not clear, and it is speculated that the HOMO level of the parent nucleus structure is suitable for emitting narrow-spectrum red light with high efficiency, so that the color emission is not ideal. In summary, the introduction of five-membered heteroaromatic rings on only one side of the boron-nitrogen multiple resonance structure on the compound parent nucleus of the invention is advantageous in providing one kind.

The compound can realize better luminous efficiency based on the mother nucleus of the five-ring fused system, and can effectively adjust and improve light color, improve luminous efficiency and prolong service life of the device when being applied to an organic electroluminescent device based on the technical characteristics.

It should be noted that unless otherwise defined below, all technical and scientific terms used herein are intended to have the same meaning as commonly understood by one of ordinary skill in the art. References to techniques used herein are intended to refer to techniques commonly understood in the art, including variations of those that are obvious to those skilled in the art or alternatives to equivalent techniques. While the following terms are believed to be well understood by those skilled in the art, the following definitions are set forth to better explain the present invention.

In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent. When C1-30 is described, 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 "comprising," "including," "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, unless otherwise specified, the expression of chemical elements generally includes the concept of isotopes having the same chemical properties, for example, the expression of "hydrogen" includes the concept of "deuterium", "tritium" having the same chemical properties, and carbon (C) includes ¹² C、 ¹³ C, etc., and are not described in detail.

Heteroatoms in the present invention are generally selected from N, O, S, P, si and Se, preferably from N, O, 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 that are C.

As used herein, the terms "(arylene) and" aromatic ring "refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated pi-electron system. As used herein, the terms "(arylene) heteroaryl" and "heteroaryl ring" refer to a monocyclic, bicyclic, or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably denotes aryl or heteroaryl substituted alkyl, 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 "substitution" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution forms a stable compound. Combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.

If substituents are described as "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.

The term "one or more" as used herein means 1 or more than 1, such as 2, 3, 4, 5 or 10, under reasonable conditions.

As used herein, unless indicated, the point of attachment of a substituent may be from any suitable position of the substituent.

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

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

In the formulae disclosed in the present specification, the expression of the ring structure "to which" - "is drawn indicates that the linking site is located at any position on the ring structure that is capable of bonding.

The above-mentioned C6 to C60 aromatic ring and C3 to C60 heteroaromatic ring in the present invention are aromatic groups satisfying pi conjugated system, and include both cases of monocyclic residues and condensed ring residues unless otherwise specified. By monocyclic residue is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenyl, terphenyl, and the like; condensed ring residues refer to molecules containing at least two benzene rings, but the benzene rings are not independent of each other, but share the ring edges to be condensed with each other, such as naphthyl, anthryl, phenanthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and 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 are connected by a single bond, such as pyridine, furan, thiophene, etc.; fused ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl rings, such as, illustratively, quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.

In the present specification, the substituted or unsubstituted C6 to C60 aromatic ring is preferably a C6 to C30 aromatic ring, more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthryl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl 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 comprises 1-naphthyl or 2-naphthyl; the anthracenyl 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 pyrenyl group is selected from 1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl groupA base; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. Preferred examples of the aromatic ring in the present invention include a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises 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 comprises 1-naphthyl or 2-naphthyl; the anthracenyl 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-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl.

In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, more preferably a group selected from the group consisting of phenyl, naphthyl, anthryl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylenyl, fluoranthenyl, naphthacene, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimeriindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl 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 comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the said Fluorenyl is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. Preferred examples of the aryl group in the present invention include a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises 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 comprises 1-naphthyl or 2-naphthyl; the anthracenyl 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-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The C6-C60 aryl group of the present invention may be a group in which the above groups are bonded by single bonds or/and condensed.

In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl ring is preferably a C3 to C30 heteroaryl ring, and may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: from furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthazolyl, anthracenooxazolyl, phenanthroazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 7, 3, 4-dipyrene, 4, 5-dipyrene, 1, 5-diazapyrenyl, 4-dipyrene, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 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, heteroaromatic rings formed by 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. As preferable examples of the heteroaromatic ring in the present invention, for example, a heteroaromatic ring of furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole.

In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a C3 to C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl, derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthyridinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenooxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2,7, 2,3, 6, 4-dipyrene, 1, 4-dipyrene, 4, 5-dipyrene, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 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. As preferable examples of the heteroaryl group in the present invention, for example, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof are mentioned, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole. The C3-C60 heteroaryl groups of the present invention may also be those wherein the above groups are joined singly or in combination by fusion.

As the aryl ether group and heteroaryl ether group in the present invention, the above-mentioned aryl group, heteroaryl group and oxygen group can be mentioned. In the present invention, examples of the arylamino group and the heteroarylamino group include the above-mentioned aryl-and heteroaryl-substituted-NH groups ₂ One or two H in the group.

In the present specification, a chain alkyl group also includes a concept of a straight chain as well as a branched alkyl group. 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-hexylneohexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl and the like.

In the present specification, the C3-C20 cycloalkyl group includes a monocycloalkyl group and a polycycloalkyl group, and as specific examples, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like can be exemplified.

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

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

In the present specification, the term "alkoxy" refers to a group composed of the aforementioned chain alkyl group and oxygen, or a group composed of the aforementioned cycloalkyl group and oxygen.

Examples of the C1-C20 alkoxy group 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 are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.

In the present specification, examples of the C1-C20 silyl group include silyl groups substituted with the groups exemplified in the above-mentioned C1-C20 alkyl groups, that is, groups formed by substituting one, two or three hydrogens on the silyl groups with the above-mentioned chain alkyl groups or cycloalkyl groups. Specific examples include: and methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-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; ring A1, ring A2, W, Y, R ¹ 、R ² The meaning of the expression is the same as in formula (1).

Based on the above formulae (1-1) and (1-2), the present invention can provide an organic light-emitting material, particularly a compound for a green fluorescent light-emitting device, having more balanced light-emitting efficiency and lifetime characteristics based on a conjugated parent nucleus containing an X-N-B-Y-W multiple resonance structure centered on a boron atom. In addition, in the parent nucleus structures of the formulas (1-1) and (1-2), three five-membered rings in the condensed structures can provide better luminous efficiency, and in the comparative test of the embodiment, if the peripheral condensed five-membered rings are replaced by six-membered rings, the luminous efficiency is reduced, and the reason may be that the rigidity of the molecular structure is enhanced, the light extraction efficiency is improved, and the carrier transmission of the molecules is more balanced, so that the service life is prolonged.

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

wherein X, Y, W, ring A1, ring A2, R ¹ The meaning is the same as that of the above expression.

In a preferred embodiment of the present method, X is N in the above formula from the viewpoint of better luminous efficiency; y is O or S, preferably S; w is preferably NR ⁵ O or S, more preferably NR ⁵ The method comprises the steps of carrying out a first treatment on the surface of the S sourceThe addition of the sub-elements can separate the surrounding HOMO and LUMO energy levels by resonance, which is advantageous for improving the luminous efficiency.

R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ Each independently represents at least one member selected from the group consisting 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; further preferred are hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;

the ring A1 and the ring A2 are C6-C30 aromatic rings or C3-C30 heteroaromatic rings condensed with the mother nucleus, the most preferable aromatic ring is benzene ring, pyridine ring or naphthalene ring,

the above-mentioned substituted or unsubstituted each group is independently substituted with one or more groups selected from halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl, or a combination of at least two thereof.

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

wherein Z is ¹ -Z ⁸ Each independently selected from CR ⁶ Or N; r is R ⁶ Is hydrogen, halogen, cyano, nitro, hydroxy, 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 unsubstitutedAt least one of substituted C6-C60 arylamino groups and substituted or unsubstituted C3-C60 heteroarylamino groups; r is R ⁶ Optionally with or without an adjacent group;

X、Y、W、R ¹ as in the case of the above-described case,

In a preferred embodiment of the invention, R ⁶ 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; further preferred are hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; further preferred are hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; more preferably, Z ¹ -Z ⁸ At least one of them is CR ⁶ And R is ⁶ Is not hydrogen; even more preferably R ⁶ The substituted or unsubstituted C1-C10 chain alkyl group or substituted or unsubstituted C6-C30 aryl group means that each of the above substituted or unsubstituted groups is independently substituted with one or more groups selected from halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl, or a combination of at least two of them.

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):

therein, X, Y, R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ The meaning of the expression is the same as described above; z is Z ⁹ -Z ¹³ Each independently selected from CR ⁶ Or N, R ⁶ Is defined as follows; r is R ⁶ Optionally with or without an adjacent group; preferably Z ⁹ -Z ¹³ At least one R of ⁶ Is other than hydrogen, more preferably R ⁶ 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 above-mentioned substituted or unsubstituted each group is independently substituted with one or more groups selected from halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl, or a combination of at least two thereof.

Further preferred is R in the present invention ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ 、R ⁶ Each independently selected from hydrogen, C1-C6 chain alkyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, furyl, thienyl, diphenylamino, cumyl.

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

the compound of the invention has high fluorescence quantum efficiency, and can obviously improve the luminous efficiency and prolong the service life of the device when being used as an OLED luminous layer material.

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

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 invention, the compounds according to the invention are used as doping materials for doping into the host material in a mass concentration of 0.1 to 10 wt.%.

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

In this case, it is preferable that the maximum emission wavelength of the sensitizer material is smaller than that of the compound of the present invention as a doping material, and it is possible to obtain better performance for a light emitting device.

The compound of the present invention has excellent light emitting performance, can give triplet excitons to realize high light emitting efficiency, and is suitable for use as a light emitting dye, especially as a green light emitting dye, based on its excellent carrier transport efficiency. Of course, since the compound of the present invention can also be used as a sensitizer to realize a good light-emitting layer together with a host material and a dye. Devices for which applications 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 labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.

The invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and at least one or more luminescent functional layers interposed between the first electrode and the second electrode, wherein the luminescent functional layers contain at least one compound according to the invention.

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

The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or display panel is an OLED display.

The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.

The OLED device prepared by the compound has high luminous efficiency and better service life, particularly can adjust the light color of the green dye to achieve the light color required by mass production, and can meet the requirements of current panels and display manufacturing enterprises on high-performance materials.

In addition, the inventors tried the following compounds D-1 different from the parent nucleus of the compound of the present invention:

for D-1, the calculation is performed by a density functional method using Gaussian program software Gaussian, wherein the density functional theory is a method for researching the electronic structure of the multi-electronic system and is well known to those skilled in the art, and is not repeated herein. The calculation result shows that the D-1 light color is blue light. It is presumed that the single heteroatom N, S has a higher electron energy level than the binodal atom due to the reduced electronegativity compared to the binodal atom, resulting in a very large blue shift of luminescence than the binodal atom, resulting in failure to achieve green luminescence. From this aspect, the parent core structure of the present invention is critical to solve the technical problem to be solved by the present invention.

Detailed Description

The technical scheme of the invention is further more specifically described below. It should be apparent to those skilled in the art that the detailed description, as well as the examples, are merely intended to facilitate an understanding of the invention and are not intended to limit the invention to the particular forms disclosed.

The compound of the invention is obtained by the following steps:

the compounds of the present invention may be obtained by known methods, for example, synthesized by known organic synthesis methods. An exemplary synthetic route for the compound of formula (1-1) or (1-2) is given below, and the method may be extended to a synthetic method for the compound of formula (1), but may be obtained by other methods known to those skilled in the art. The representative synthetic route for the compounds of the general formula of the present invention is as follows:

under the general route, the compound of the invention can be synthesized by replacing different raw materials. However, the compound of the present invention is not limited to the above synthesis method, and one skilled in the art may select other synthesis methods as needed based on the known art.

Device implementation method

The Organic Light Emitting Device (OLED) of the present invention may employ various elements in the prior art except that the light emitting layer portion includes the above-described compound of the present invention. Specifically, the OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.

In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.

The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the 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 combinations thereof may be used.

The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.

The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one 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 may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate)

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

The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-51 may also be used to dope one or more of HI-1-HI-3 described below.

The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.

According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.

In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

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

In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described above; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, but are not limited thereto.

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 an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).

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

In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.

An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.

LiQ、LiF、NaCl、CsF、Li ₂ O、Cs ₂ CO ₃ 、BaO、Na、Li、Ca、Yb、Mg。

Examples

The organic compound of the invention is representatively synthesized, and is applied to an organic electroluminescent device together with a corresponding comparative compound to test the device performance under the same conditions.

Synthetic examples

Specific methods for preparing the above novel compounds of the present invention will be described below by way of example with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples. It should be noted that, the method for obtaining the compound is not limited to the synthetic method and raw materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the compound proposed in the present invention. All compounds of the synthesis process not mentioned in the present invention are commercially available starting products or are prepared by these starting products according to known methods. The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, t-butylbenzene, boron tribromide, carbazole, diphenylamine, etc., may be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai pichia pharmaceutical company, carboline reagent company, etc. Analytical detection of intermediates and compounds in the present invention uses an absiex mass spectrometer (4000 QTRAP).

Synthesis example 1: s1 synthesis:

synthesis of intermediate M1-1:

to a 2L single flask was added raw material A (150 g), raw material B (54.49 g), pd (dppf) 2Cl2 (7.72 g), sodium t-butoxide (76.68 g), toluene (500 ml) as a solvent at room temperature, nitrogen was replaced three times, and the reaction was carried out at 80℃overnight. After the reaction solution was cooled, it was subjected to flash column chromatography on a silica gel column containing silica gel, with methylene chloride as an eluent, and concentrated, and then boiled and washed with ethanol to obtain 130g of a white solid M1-1 in a yield of 86.3%. Mass spectrometry determines molecular ion mass: 293.12 (theory: 293.07).

Synthesis of intermediate M1-2

To a 1000ml single flask at room temperature was added M1-1 (130 g), boc2O (115.72 g), 4-dimethylaminopyridine (26.99 g), 1, 4-dioxane (300 ml) as a solvent, and the mixture was refluxed for 3 hours. Concentrated, dichloromethane (300 ml) was dissolved, and washed three times with an anhydrous sodium carbonate aqueous solution (30 ml). The mixture was separated, dried over anhydrous sodium sulfate and concentrated to give 165.52g of a white solid M1-2 in a yield of 95%. Mass spectrometry determines molecular ion mass: 393.18 (theory: 393.13).

Synthesis of intermediate M1-3

To a 1000ml single flask at room temperature was added M1-2 (165.00 g), benzimidazole (54.38 g), pd2dba3 (7.66 gl), tri-tert-butylphosphine tetrafluoroborate (4.86 g), sodium tert-butoxide (60.32 g), toluene (300 ml) as a solvent, and nitrogen was replaced three times, and the reaction was carried out at 100℃overnight. Standing at room temperature, pouring the reaction solution into a silica gel column filled with silica gel, performing flash column chromatography by using methylene dichloride as an eluent, concentrating, and boiling and washing with ethanol to obtain 159.34g of white solid M1-3, wherein the yield is 80%. Mass spectrometry determines molecular ion mass: 475.31 (theory: 475.20).

Synthesis of intermediate M1-4

M1-3 (159 g) was added to a 1000ml single-necked flask at room temperature, 1, 4-dioxane (300 ml) was used as a solvent, concentrated hydrochloric acid (50 ml) was added thereto, and the mixture was heated to 100℃and refluxed overnight. Cooling to room temperature, concentrating, adding dichloromethane for dissolving, washing with water for three times, washing with sodium carbonate aqueous solution once, drying the organic phase with anhydrous sodium sulfate, and spin-drying the solvent to obtain 125.56g of white solid M1-4, wherein the yield is 100%. Mass spectrometry determines molecular ion mass: 375.22 (theory: 375.15).

Synthesis of intermediate M1-5

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 a solvent were reacted overnight at 100℃with three nitrogen substitutions. Standing at room temperature, filtering, concentrating the filtrate by stirring with silica gel, and performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 19.51g of white solid with a yield of 65%. Mass spectrometry determines molecular ion mass: 563.31 (theory: 563.22).

Synthesis of end product S1

M1-5 (19 g), xylene (100 ml) and nitrogen were replaced 3 times at room temperature in a 500ml three-necked flask, an n-hexane solution of t-butyllithium (31.57 ml, 1.6M) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (4.7 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (11.76 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 5.43g of the pre-sublimation sample in 30% yield. Mass spectrometry determines molecular ion mass: 537.32 (theory: 537.24).

Synthesis example 2: s2 synthesis:

synthesis of intermediate M2-1

M1-4 (20 g), raw material E (15.76 g), pd2dba3 (0.97 g), tri-tert-butylphosphine tetrafluoroborate (0.62 gl), sodium tert-butoxide (7.67 g), toluene (100 ml) as a solvent were reacted at room temperature over night with nitrogen replaced three times at 100 ℃. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 21.01g of white solid M2-1 with a yield of 70%. Mass spectrometry determines molecular ion mass: 563.34 (theory: 563.22).

Synthesis of end product S2

M2-1 (20 g), xylene (100 ml) and nitrogen were replaced 3 times at room temperature in a 500ml three-necked flask, an n-hexane solution of t-butyllithium (33.23 ml, 1.6M) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (4.95 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (12.38 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 6.1g of the sample before sublimation in 32% yield. Mass spectrometry determines molecular ion mass: 537.27 (theory: 537.24).

Synthesis example 3: s3, synthesis:

synthesis of intermediate M3-1

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 a solvent were reacted at room temperature over night with nitrogen replaced three times at 100 ℃. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 18.61g of white solid M3-1 with a yield of 62%. Mass spectrometry determines molecular ion mass: 563.27 (theory: 563.22).

Synthesis of end product S3

M3-1 (18.6 g), xylene (100 ml) and nitrogen were added to a 500ml three-necked flask at room temperature, and a n-hexane solution of t-butyllithium (30.91 ml, 1.6M) was added to the system at-70℃for 3 times, followed by stirring at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (4.61 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (11.52 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 4.96g of the pre-sublimation sample in 28% yield. Mass spectrometry determines molecular ion mass: 537.33 (theory: 537.24).

Synthesis example 4: s4, synthesis:

synthesis of intermediate M4-1

M1-4 (20G), raw material G (15.76G), pd2dba3 (0.97G), tri-tert-butylphosphine tetrafluoroborate (0.62G, 2.13 mmol), sodium tert-butoxide (7.67G), toluene (100 ml) as a solvent were reacted overnight at 100℃with nitrogen replaced three times. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 19.51g of white solid M4-1 with a yield of 65%. Mass spectrometry determines molecular ion mass: 563.34 (theory: 563.22).

Synthesis of end product S4

M4-1 (19.5 g), xylene (100 ml) and nitrogen were added to a 500ml three-necked flask at room temperature, the nitrogen was replaced 3 times, a n-hexane solution of t-butyllithium (32.4 ml of 1.6M) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (4.83 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (12.07 ml) was then added at-40℃and the temperature was raised to 120℃to react overnight. The system was cooled to room temperature, concentrated by adding dichloromethane (100 ml) with silica gel, column chromatographed (PE: dcm=20:1), and recrystallized twice from crude toluene/ethanol to give 5.61g of pre-sublimation sample with a yield of 30.2%. Mass spectrometry determines molecular ion mass: 537.26 (theory: 537.24).

Synthesis example 5: synthesis of S12

Synthesis of intermediate M4-1

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 a solvent, was reacted at 100℃overnight with nitrogen replaced three times. Standing at room temperature, filtering, concentrating the filtrate by stirring with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 14.69g of white solid M12-1 with a yield of 63%. Mass spectrometry determines molecular ion mass: 583.21 (theory: 583.18).

Synthesis of end product S12

To a 500ml three-necked flask at room temperature, M12-1 (14.69 g), xylene (100 ml) were added, nitrogen was replaced 3 times, a n-hexane solution of t-butyllithium (23.57 ml) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red from anhydrous clarification. Boron tribromide (3.51 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (8.78 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 4.91g of the pre-sublimation sample in 35% yield. Mass spectrometry determines molecular ion mass: 557.34 (theory: 557.21).

Synthesis example 6: synthesis of S13

Synthesis of intermediate M12-1

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 a solvent, was reacted at 100℃overnight with three substitutions of nitrogen. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 15.85g of white solid M13-1 with a yield of 68%. Mass spectrometry determines molecular ion mass: 583.23 (theory: 583.18).

Synthesis of end product S13

M13-1 (15.85 g), xylene (100 ml) and nitrogen were added to a 500ml three-necked flask at room temperature, the nitrogen was replaced 3 times, an n-hexane solution of t-butyllithium (25.44 ml 1.6M) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (3.79 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (9.48 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 4.69g of the pre-sublimation sample in 31% yield. Mass spectrometry determines molecular ion mass: 557.31 (theory: 557.21).

Synthesis example 7: s6, synthesis:

synthesis of intermediate M6-1

To a 1000ml single-necked flask, 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 t-butoxide (54.84 g), toluene (300 ml) as a solvent were charged, and the nitrogen was replaced three times, and reacted overnight at 100 ℃. Standing at room temperature, pouring the reaction solution into a silica gel column filled with silica gel, performing flash column chromatography by using methylene dichloride as an eluent, concentrating, and boiling and washing with ethanol to obtain 157.51g of white solid M6-1, wherein the yield is 75%. Mass spectrometry determines molecular ion mass: 551.35 (theory: 551.23).

Synthesis of intermediate M6-2

M6-1 (157.51 g) was added to a 1000ml single-necked flask at room temperature, 1, 4-dioxane (300 ml) was used as a solvent, concentrated hydrochloric acid (50 ml) was added thereto, and the mixture was heated to 100℃to reflux overnight. Cooling to room temperature, concentrating, adding dichloromethane for dissolving, washing with water for three times, washing with sodium carbonate aqueous solution once, drying the organic phase with anhydrous sodium sulfate, and spin-drying the solvent to obtain 122.5g of white solid M6-2, wherein the yield is 95%. Mass spectrometry determines molecular ion mass: 451.23 (theory: 451.18).

Synthesis of intermediate M6-3

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 a solvent, was reacted at 100℃overnight with nitrogen replaced three times. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 13.81g of white solid M6-3 with a yield of 65%. Mass spectrometry determines molecular ion mass: 639.32 (theory: 639.25).

Synthesis of end product S6

M6-3 (13.81 g), xylene (100 ml) and nitrogen were added to a 500ml three-necked flask at room temperature, the nitrogen was replaced 3 times, a n-hexane solution of t-butyllithium (20.22 ml) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red from anhydrous clarification. Boron tribromide (3.01 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system turned from white turbidity to a red solution. N, N-diisopropylethylamine (7.53 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, concentrated by adding dichloromethane (100 ml) with silica gel, and subjected to column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 3.9g of a sample before sublimation, with a yield of 29.5%. Mass spectrometry determines molecular ion mass: 613.33 (theory: 613.27).

Synthesis example 8: s7, synthesis:

synthesis of intermediate M7-1

M6-2 (15 g), starting 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 a solvent, was reacted at 100℃overnight with nitrogen replaced three times. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 13.28g of white solid M7-1 with a yield of 62.5%. Mass spectrometry determines molecular ion mass: 639.28 (theory: 639.25).

Synthesis of end product S7

To a 500ml three-necked flask at room temperature, M7-1 (13.28 g), xylene (100 ml) were added, nitrogen was replaced 3 times, an n-hexane solution of t-butyllithium (19.44 ml, 1.6M) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (2.9 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (7.25 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 4.07g of the pre-sublimation sample in 32% yield. Mass spectrometry determines molecular ion mass: 613.35 (theory: 613.27).

Synthesis example 9: s10, synthesis:

synthesis of intermediate M10-1

M6-2 (15 g), starting 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 a solvent, was reacted at 100℃overnight with nitrogen replaced three times. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 14.9g of white solid M10-1 with a yield of 68%. Mass spectrometry determines molecular ion mass: 659.33 (theory: 659.22).

Synthesis of end product S10

M10-1 (14.9 g), xylene (100 ml) and a nitrogen gas were added to a 500ml three-necked flask at room temperature, and a n-hexane solution of t-butyllithium (21.16 ml, 1.6M) was added to the system at-70℃for 3 times, followed by stirring at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (3.15 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (7.88 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, concentrated by adding dichloromethane (100 ml) with silica gel, column chromatographed (PE: dcm=20:1), and recrystallized twice from crude toluene/ethanol to give 4.15g of the pre-sublimation sample in 29% yield. Mass spectrometry determines molecular ion mass: 633.27 (theory: 633.24).

Synthesis example 10: s11 synthesis:

synthesis of intermediate M11-1

M6-2 (15 g), raw 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 a solvent, were reacted overnight at 100℃with three substitutions of nitrogen. Standing at room temperature, filtering, concentrating the filtrate with silica gel, performing column chromatography (PE: DCM=30:1), and recrystallizing with toluene/ethanol to obtain 13.15g of white solid M11-1 with a yield of 60%. Mass spectrometry determines molecular ion mass: 659.29 (theory: 659.22).

Synthesis of end product S11

To a 500ml three-necked flask at room temperature, M11-1 (13.15 g), xylene (100 ml) were added, nitrogen was replaced 3 times, an n-hexane solution of t-butyllithium (18.67 ml, 1.6M) was added to the system at-70℃and stirred at room temperature for 5 minutes, and the temperature was raised to 60℃to react for 2 hours, whereby the system became dark red by clarification without water. Boron tribromide (2.78 ml) was added to the system at-40℃and stirred at room temperature for 1h, the system changing from white turbidity to a red solution. N, N-diisopropylethylamine (6.96 ml) was then added at-40℃and the temperature was raised to 120℃for reaction overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and concentrated on silica gel, column chromatography (PE: dcm=20:1), and the crude toluene/ethanol was recrystallized twice to give 3.91g of the sample before sublimation in 31% yield. Mass spectrometry determines molecular ion mass: 633.30 (theory: 633.24).

Device embodiment

The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;

placing the glass substrate with the anode in a vacuum cavity, vacuumizing to < 1X 10-5Pa, and sequentially performing vacuum thermal evaporation on the anode layer film to obtain a 10nm HT-4/HI-3 (97/3,w/w) mixture as a hole injection layer, a 60nm compound HT-4 as a hole transport layer and a 5nm compound HT-14 as an electron blocking layer; a binary mixture of 20nm compound BFH-4:S1 (100:3, w/w) as a light-emitting layer; 5nm ET-23 as hole blocking layer, 25nm compound ET-69:ET-57 (50/50, w/w) mixture as electron transport layer, 1nm LiF as electron injection layer, 150nm metallic aluminum as cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.

Device examples 2-10 and comparative examples 1-3 were fabricated as in device example 1, except that dye S1 was replaced with the compounds listed in Table 1 and R-1 to R-3, respectively.

Wherein, ref-1 and Ref-2 refer to the synthetic methods in CN 114144420A; ref-3 refers to the synthetic method in CN 111253421A; the above synthesis method is not described here in detail.

The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:

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 lifetime of the devices were measured using a digital source table and PR650 at the same brightness. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second ² The voltage at the time is the driving voltage under the corresponding brightness, and meanwhile, the external quantum efficiency (EQE%) of the device can be obtained through direct test on PR 650;

the properties of the organic electroluminescent devices prepared in the device examples 1 to 10 and the device comparative examples 1 to 3 are shown in Table 1 below.

TABLE 1

The devices of the examples were all high-efficiency green fluorescence light emitting elements, and comparative example 3 failed to achieve acceptable green luminescence and emitted blue light, so the data in the above table was "-".

The results show that the novel compounds of the invention have better performance in organic electroluminescent devices. In the compounds of examples 1 to 10, the boron atom is bonded to the mother nucleus, and the thiophene ring has resonance effect and can balance carrier transmission, so that the device of the examples can realize lower working voltage and higher external quantum efficiency.

The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. While the invention has been described in connection with the embodiments, it is to be understood that the invention is not limited to the above embodiments, but is capable of numerous modifications and improvements by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims, and equivalent substitutions for various raw materials of the inventive product, addition of auxiliary components, selection of specific modes, etc., are all within the scope of the invention and the scope of the disclosure.

Claims

1. A boron-containing organic compound characterized by having a structure represented by formula (1):

y, W are each independently selected from CR ³ R ⁴ 、NR ⁵ At least one of O or S;

R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ each independently represents any one selected from hydrogen, halogen, cyano, nitro, hydroxy, 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 is ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ Optionally with or without an adjacent group;

2. The boron-containing organic compound according to claim 1, wherein the compound has a structure represented by the formula (1-1) or the formula (1-2),

in the formula (1-1) or (1-2), X is CR ² Or N;

ring A1, ring A2, W, Y, R ¹ 、R ² The meaning of expression is the same as in claim 1.

3. The boron-containing organic compound according to claim 2, wherein the compound has a structure represented by the formula (1-a), (1-b), (1-c) or (1-d),

wherein X, Y, W, ring A1, ring A2, R ¹ The same meaning as expressed in claim 2.

4. The boron-containing organic compound according to claim 2, wherein,

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 、R ⁵ Each independently represents at least one member selected from the group consisting 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 heteroarylSeed; further preferred are hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;

the rings A1, A2 are C6-C30 aromatic rings or C3-C30 heteroaromatic rings fused to the parent nucleus, preferably benzene, pyridine or naphthalene rings,

the above-mentioned substituted or unsubstituted each group means that each group is independently substituted with one or more groups selected from halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 aryloxy, and C3-C30 heteroaryl, or a combination of at least two of them,

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 is ¹ -Z ⁸ 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, and substituted or unsubstituted C3-C60 heteroarylamino; r is R ⁶ Optionally with or without an adjacent group;

X、Y、W、R ¹ as expressed in claim 2,

6. The boron-containing organic compound according to claim 5, wherein,

R ⁶ 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; further preferred are hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; further preferred are hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;

more preferably, Z ¹ -Z ⁸ At least one of them is CR ⁶ And R is ⁶ Is not hydrogen; even more preferably R ⁶ Is a substituted or unsubstituted C1-C10 chain alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

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):

Therein, X, Y, R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ The meaning of the expression is the same as in claim 2;

Z ⁹ -Z ¹³ each independently selected from CR ⁶ Or N, R ⁶ As defined in formula (1-a-1); r is R ⁶ Optionally with or without an adjacent group;

preferably Z ⁹ -Z ¹³ At least one R of ⁶ Is other than hydrogen, more preferably R ⁶ 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;

8. The boron-containing organic compound according to any one of claim 5 to 7,

R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ 、R ⁶ each independently selected from hydrogen, C1-C6 chain alkyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, furyl, thienyl, diphenylamino, cumyl.

9. The boron-containing organic compound according to claim 1, wherein the structure represented by formula (1) is a compound structure represented by:

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 luminescent material; preferably, the luminescent material is applied in 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 a compound according to any one of claims 1 to 9 as a functional material in an organic electronic device comprising: organic electroluminescent devices, optical sensors, solar cells, lighting elements, information labels, electronic artificial skin sheets, sheet scanners, or electronic papers.

12. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 9.

13. The organic electroluminescent device according to claim 12, wherein the light-emitting layer comprises a host material and a sensitizer material in addition to the compound according to any one of claims 1 to 9 as a doping material;

the host material is a single P-type host material, an N-type host material, a single molecule excimer host material or a mixture of the two host materials,

The sensitizer material is a thermally activated delayed fluorescence material, or a phosphorescent light-emitting material, or a mixture of a thermally activated delayed fluorescence material and a phosphorescent light-emitting material.

14. The organic electroluminescent device according to claim 12, wherein the sensitizer material has a maximum emission wavelength smaller than that of the compound according to any one of claims 1 to 9 as a doping material.