Boron-nitrogen-containing organic compound, application thereof and organic electroluminescent device

Abstract

The invention relates to an organic compound, belongs to the technical field of organic light-emitting materials, and also relates to an application of the compound in an organic light-emitting device. The organic compound has a structure as shown in a formula (1), and can be used as a TADF material, a light-emitting layer object material or a dopant. The OLED device prepared from the compound provided by the invention has high luminous efficiency and longer service life. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a boron-nitrogen-containing organic compound, belonging to the technical field of organic luminescent materials. The present invention also relates to the application of the compound in an organic electroluminescent device and the organic electroluminescent device. Background Art

[0002] OLED (Organic Light-Emitting Diode) refers to an organic semiconductor composed of an extremely thin coating of organic material and a glass substrate that emits light when an electric current passes through it. As a next-generation display technology, OLED offers superior display performance compared to LCD, boasting advantages such as self-luminescence, excellent display quality, low power consumption, high flexibility, and ultra-thinness. It is widely used in the screens of smartphones, automotive electronics, smart wearable devices, VR equipment, and other products.

[0003] OLEDs are primarily made of three types of luminescent materials: blue, red, and green. These materials collectively determine the self-luminous performance and lifespan of OLEDs. While blue luminescent materials can emit brighter light, they have lower luminous efficiency and a shorter lifespan than red and green luminescent materials. Currently, red and green OLED phosphorescent materials are already in mass production for OLED screens. However, blue OLED phosphorescent materials have long suffered from limitations in color purity and lifespan, leading to the widespread use of blue fluorescent materials in commercial OLED products.

[0004] As OLED products gradually enter the market, demand for their performance is increasing. Recently, patent documents CN112645968A and CN112174992A reported a class of TADF (Thermally Activated Delayed Fluorescence) multi-resonance fluorescent compounds based on the BN resonance structure. These compounds also consist of a rigid polycyclic aromatic skeleton composed of B, N, and benzene rings. Nitrogen atoms have an opposite resonance effect to that of boron atoms, and the opposite resonance effect is enhanced at the para position. Therefore, this effect can significantly separate the HOMO and LUMO orbitals, resulting in certain TADF properties. Although this series of materials has broad application prospects, they suffer from significant intramolecular rotation, resulting in energy loss due to vibrational and rotational energy levels, resulting in low external quantum efficiency. Even when dimethylfluorene structures are used to suppress intramolecular rotational energy levels, as reported in some of the compounds described in the patents, the imbalanced charge transfer leads to poor device lifetimes. This type of organic electroluminescent material still has a lot of room for improvement in terms of luminescence performance, and the industry urgently needs to develop new blue light emitting material systems to meet commercial needs.

[0005] Therefore, existing organic electroluminescent materials still have significant room for improvement in their luminescent properties, and the industry urgently needs to develop new luminescent material systems to meet commercialization needs. Through careful consideration and continuous experimentation, the researchers of the present invention have discovered an ingenious molecular design, which is described in detail below. Surprisingly, the compounds disclosed in this invention are highly suitable for use in OLEDs and improve device lifespan. Summary of the Invention

[0006] In response to the shortcomings of the prior art, the present invention provides an organic compound, its application, and an organic electroluminescent device. The compound of the present invention can be used as a TADF material, a guest material (dye), or a dopant in the light-emitting layer. OLED devices prepared using the compound of the present invention exhibit high luminous efficiency and extended device life.

[0007] In a first aspect, the present invention provides an organic compound having a structure shown in formula (1):

[0008]

[0009] In formula (1),

[0010] Rings A, B, C, E, and F are each independently selected from a C6-C60 aromatic ring and a C3-C60 heteroaromatic ring;

[0011] R 7 In the ortho position of the N-substituted ring E, R 8 In the ortho position of the N-substituted ring F, R 7 and R 8 are independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 7 and R 8 At least one of the following is selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group;

[0012] R A 、R B 、R C 、R E 、R F represents single substitution to maximum substitution, R A 、R B 、R C 、R E 、R FEach is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R A 、R B 、R C 、R E 、R F are independently connected to each other by chemical bonds to form a ring or are not connected; wherein R A 、R B 、R C 、R E 、R F At least one of them is a structure of formula (a) or formula (b),

[0013]

[0014] In formula (a) or formula (b), R 1 、R 2 、R 3 、R 4 、R 5 、R 6 are independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, R 1 、R 2 Connect or not connect; R 3 、R 4 Connect or not connect, R 5 、R 6 Connect or not connect; the condition is, R 1 and R 2 At least one of them is not hydrogen; Ra and Rb are independently selected from substituted or unsubstituted C1-C20 chain alkyl groups; Y 1 and Y 2 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0015] The above-mentioned substituents are each independently selected from any one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, cyano, nitro, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. The expression of the ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond, and the * indicates the connection site.

[0016] The polycyclic aromatic compound provided by the present invention has a specific molecular structure shown in formula (1), has good stability and spatial configuration, can utilize triplet excitons to achieve higher luminous efficiency, has excellent carrier transport characteristics, and effectively avoids molecular aggregation, which has an improvement effect on the stability and efficiency of the device. Other more polycyclic mother core structures are not as long as the device life caused by the specific mother core structure in the present invention. In addition, the present invention also introduces the structure of formula (a) or formula (b) into the periphery of the mother core, so that the polycyclic aromatic compound has excellent photoelectric properties. The reason may be that the steric hindrance of Ra and Rb in the structure of formula (a) or formula (b) makes the aliphatic ring structure of the structure of formula (a) or formula (b) in a moderate conformation, resulting in good film forming properties, which is beneficial to improving the efficiency and life of the device. In formula (a), R 1 With R 2 When not being hydrogen at the same time, it helps the structure maintain a dominant conformation (chair conformation). It is speculated that when in this conformation, the molecular arrangement is conducive to forming a more efficient film and can enable devices of the corresponding materials to obtain higher external quantum efficiency.

[0017] It should be noted that, unless otherwise defined below, all technical and scientific terms used herein are intended to have the same meaning as those commonly understood by those skilled in the art. References to technology used herein are intended to refer to technology commonly understood in the art, including variations of technology or substitutions of equivalent technologies that would be apparent to those skilled in the art. While it is believed that the following terms are well understood by those skilled in the art, the following definitions are set forth to better explain the present invention.

[0018] In this specification, the expression of Ca to Cb indicates 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 C30, 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. Other numerical ranges are not repeated here.

[0019] 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.

[0020] In the present invention, unless otherwise specified, the expression of chemical elements generally includes the concept of isotopes with the same chemical properties. For example, the expression of "hydrogen" also includes the concept of "deuterium (D)" and "tritium (T)" with the same chemical properties, and the expression of carbon (C) includes 12 C. 13 C, etc., no further details.

[0021] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, and is preferably selected from N, O and S.

[0022] 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.

[0023] 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 group substituted with an aryl or heteroaryl group, wherein the aryl, heteroaryl, and alkyl groups are as defined herein.

[0024] As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

[0025] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogen atoms on the designated atom are replaced with a group selected from the indicated group, provided that the designated atom's normal valence is not exceeded in the current context and that the substitution results in a stable compound. Combinations of substituents and / or variables are permissible only if such combinations result in stable compounds.

[0026] 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.

[0027] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0028] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0029] 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.

[0030] The term "about" means within ±10%, preferably within ±5%, and more preferably within ±2% of the stated numerical value.

[0031] 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.

[0032] The aforementioned C6-C60 aromatic rings and C3-C60 heteroaromatic rings in the present invention, unless otherwise specified, are aromatic groups that satisfy a 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 fused 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, phenanthrenyl, 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 other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a fused 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.

[0033] In the present specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, more preferably an aromatic ring selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrene, chrysene, peryl, fluoranthenyl, naphthyl, pentacene, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, 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, perylenyl, 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-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 naphthacene group is selected from the group consisting of 1-naphthacene, 2-naphthacene and 9-naphthacene.

[0034] In the present specification, the substituted or unsubstituted C6-C60 aryl group is preferably a C6-C30 aryl group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrene, chrysene, peryl, fluoranthenyl, naphthyl, pentacene, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, 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. wherein 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; and the naphthacene group is selected from the group consisting of 1-naphthacene, 2-naphthacene, and 9-naphthacene. The C6-C60 aryl group of the present invention may also be a combination of the above groups connected by single bonds or / and fused.

[0035] In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, which can 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, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1, 1,2,3,4-tetrazolyl, 1,2,3,5-tetrazolyl, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 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 the heteroaromatic ring in the present invention include furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole or indolocarbazole.

[0036] 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 its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridine yl, 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, pyrimidazinyl, pyridinyl, 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-oxadiazole, oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 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 furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole. The C3-C60 heteroaryl group of the present invention may also be a combination of the above groups linked by single bonds or / and fused.

[0037] In the present invention, examples of aryloxy and heteroaryloxy groups include groups formed by the aforementioned aryl and heteroaryl groups and oxygen. In the present invention, examples of arylamino and heteroarylamino groups include groups formed by the aforementioned aryl and heteroaryl groups replacing one or two H groups in the -NH2 group.

[0038] In this specification, the term "chain alkyl" encompasses both straight-chain and branched alkyl groups. Examples of C1-C20 chain alkyl groups 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, and 2-ethylhexyl. Examples of C1-C20 chain haloalkyl groups include trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl.

[0039] In the present specification, the C3-C20 cycloalkyl group includes monocyclic alkyl groups and polycyclic alkyl groups, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups.

[0040] The C2 to C20 alkenyl group includes both straight-chain and branched alkenyl groups, and also includes cycloalkenyl groups. The number of carbon atoms in the alkenyl group is preferably 2 to 10. Specific examples include ethenyl, 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 groups and alkoxy groups.

[0041] 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.

[0042] 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, and dodecyloxy groups. Preferred groups include methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, and isopentyloxy groups, and more preferred groups include methoxy.

[0043] In a preferred embodiment of the present invention, ring A and ring B have a structure as shown in formula (d) or formula (e):

[0044]

[0045] Among them, the dotted line represents the fused bond of the group;

[0046] In formula (e), X represents O, S, NR 0 、C(R 0 )2;

[0047] In formula (d) and formula (e), Z 12 ~Z 15 、X 1 ~X 4 are independently selected from CR or N,

[0048] Among them, each R 0 , R are independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, halogen, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, R 0 They are connected to each other by chemical bonds to form a ring or not, and R are connected to each other by chemical bonds to form a ring or not;

[0049] The ring C has a structure as shown in formula (f):

[0050]

[0051] Wherein, the dotted line represents the fused bond of the group; Z 5 ~Z 7 Each independently is CR or N;

[0052] R is independently selected from any one of hydrogen, halogen, cyano, nitro, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; R is not connected to adjacent ring structures or is connected to form a ring through chemical bonds;

[0053] The above-mentioned substituted substituents are each independently selected from any one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, cyano, nitro, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. In a preferred embodiment of the present invention, the compound of the present invention has a structure shown in the following formula (1-1) or formula (1-2):

[0054]

[0055] In formula (1-1) and formula (1-2), R 7 and R 8 The meaning of expression is the same as in formula (1);

[0056] Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 are independently selected from CR or N, R is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, halogen, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 There is at least one connecting structure (a) or (b); Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 Any two adjacent R's in are connected to form a ring or not;

[0057] X represents O or S;

[0058] Preferably, in formula (1-1), Z 2 、Z 3 、Z 6 、Z 9 、Z 10 、Z 13 、Z 14 、Z 13’ 、Z 14’ At least one of them is connected to formula (a) or formula (b);

[0059] Preferably, in formula (1-2), Z 2 、Z 3 、Z 6 、Z 9 、Z 10 、Z 13 、Z 14 、X 2 、X 3 At least one of them is connected to formula (a) or formula (b),

[0060] Preferably, Z 1 ~Z 15 、Z 12’~Z 15’ 、X 1 ~X 4 Any two adjacent R in are connected to form the following structure:

[0061] * indicates the connection site;

[0062] The above-mentioned substituents are each independently selected from any one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, cyano, nitro, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof.

[0063] In a preferred embodiment of the present invention, in formula (a) and formula (b), Ra and Rb are each independently selected from a C1-C20 chain alkyl group. More preferably, Ra and Rb are each independently selected from a C1-C6 chain alkyl group. For example, Ra and Rb are each independently selected from a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

[0064] In a preferred embodiment of the present invention, in formula (a) and formula (b), Y 1 and Y 2 are independently selected from a single bond, a C6-C30 arylene group, and a C3-C30 heteroarylene group. More preferably, Y 1 and Y 2 are independently selected from a single bond, a C6-C20 arylene group. 1 and Y 2 Each is independently selected from a single bond, a phenyl group, and a naphthyl group.

[0065] In a preferred embodiment of the present invention, the compound of the present invention has any one of the structures shown in the following formulas (2-1) to (2-16):

[0066]

[0067]

[0068] X represents O or S, preferably S;

[0069] Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 The meaning of expression is the same as in formula (1-1) and formula (1-2);

[0070] R 1、R 2 、R 3 、R 4 、R 5 、R 6 The meanings of expressions are the same as those in formula (a) and formula (b).

[0071] In a preferred embodiment of the present invention, Z in the above structural formula 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 are independently selected from CR, R are independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and the above substituents are independently selected from any one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl. More preferably, Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 Each of the above substituents is independently selected from CR, each of R is independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl, and each of the above substituents is independently selected from any one of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, or C3-C30 heteroaryl, or a combination of at least two thereof. Most preferably, Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 Each of the above substituents is independently selected from C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C20 aryl, or C3-C20 heteroaryl, and each of the above substituents is independently selected from any one or a combination of at least two of the following: C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C20 aryl, or C3-C20 heteroaryl. For example, Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X4 Each of the above substituents is independently selected from CR, and each of R is independently selected from one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, 2,2,5,5-tetramethylhexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridine, and substituted or unsubstituted pyrimidine. The above substituents are each independently selected from any one of methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, 2,2,5,5-tetramethylhexyl, phenyl, biphenyl, and naphthyl, or a combination of at least two thereof.

[0072] In a preferred embodiment of the present invention, Z in the above structural formula 1 、Z 2 、Z 4 、Z 5 、Z 7 、Z 8 、Z 10 ~Z 12 、Z 12’ 、Z 15 、Z 15’ CH, Z 3 、Z 6 、Z 9 、Z 13 、Z 14 、Z 13’ 、Z 14’ is CR, and R is each independently selected from H, fluorine, chlorine, nitro, cyano, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, 2,2,5,5-tetramethylhexyl, phenyl, naphthyl, tert-butylphenyl, pyridine, pyrimidine, or one of the following groups:

[0073]

[0074] In a preferred embodiment of the present invention, in formulas (2-1) to (2-12), X 1 、X 4 CH, X 2 、X 3 CR, R are each independently selected from one of H, methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, 2,2,5,5-tetramethylhexyl, phenyl, naphthyl, tert-butylphenyl, pyridine and pyrimidine.

[0075] In a preferred embodiment of the present invention, in formula (a) and formula (b), R 1 ~R 6 are independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, R1 and R 2 At least one of them is not hydrogen, and the above-mentioned substituents are independently selected from any one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl. More preferably, R 1 ~R 6 are independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, R 1 and R 2 At least one of them is not hydrogen, and the above-mentioned substituents are independently selected from any one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl. Most preferably, R 1 ~R 6 are independently selected from hydrogen, substituted or unsubstituted C1-C6 chain alkyl, substituted or unsubstituted C3-C8 cycloalkyl, R 1 and R 2 At least one of them is not hydrogen, and the above-mentioned substituents are independently selected from any one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl.

[0076] In a preferred embodiment of the present invention, R 1 ~R 6 Each is independently H, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, cyclopentyl, cyclohexyl and any one of the following groups:

[0077]

[0078] where R 1 and R 2 At least one of them is not hydrogen,

[0079] * indicates the connection site, and the structure with two * indicates R 1 ~R 6 The two connections in form this structure.

[0080] In a preferred embodiment of the present invention, R 7 and R 8 are independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, wherein R 7 and R 8At least one of the substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups is selected from one of the following groups: halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl groups, C3-C30 heteroaryl groups, or a combination of at least two of them. More preferably, R 7 and R 8 are independently selected from hydrogen, substituted or unsubstituted C1-C6 chain alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, wherein R 7 and R 8 At least one of the substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups is selected from one of the following groups: halogen, C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C20 aryl groups, C3-C20 heteroaryl groups, or a combination of at least two of them. Most preferably, R 7 and R 8 are independently selected from hydrogen, substituted or unsubstituted C1-C6 chain alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, wherein R 7 and R 8 At least one of the substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups are selected, and the above-mentioned substituents are each independently selected from any one of C1-C6 chain alkyl groups, C3-C6 cycloalkyl groups, and C6-C20 aryl groups, or a combination of at least two of them. For example, R 7 and R 8 are independently selected from one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, and R 7 and R 8 At least one is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridine, and substituted or unsubstituted pyrimidine, and the above substituents are each independently selected from any one or a combination of at least two of methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, 2,2,5,5-tetramethylhexyl, phenyl, biphenyl, and naphthyl.

[0081] In a more preferred embodiment of the present invention, R 7 and R 8 Any one of H and the following groups (i.e. R 7 and R 8 At least one of them is not H),

[0082]

[0083] * indicates the connection site.

[0084] Furthermore, the organic compounds of the present invention may preferably include the specific structural compounds shown below, which are only representative and do not limit the scope of the present invention:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] The organic compound of the present invention has a simple and easy preparation process, readily available raw materials, and is suitable for mass production and expansion. It is used as a material for the light-emitting layer in an organic electroluminescent device, enabling the device to achieve high-quality blue light emitting effects, effectively extending the life of the device and improving the luminous efficiency.

[0093] In a second aspect, the present invention provides a use of the organic compound according to the first aspect, wherein the organic compound is used in an organic electronic device.

[0094] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper, and an organic electroluminescent device is further preferred.

[0095] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0096] Preferably, the organic compound is used as a luminescent dye of a light-emitting layer in an organic electroluminescent device.

[0097] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound as described in the first aspect, preferably comprising at least one organic compound having the structure shown in the above-mentioned present invention.

[0098] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one organic compound as described in the first aspect, preferably includes at least one organic compound having the structure shown in the above-mentioned present invention.

[0099] Preferably, the light-emitting layer includes a host material and a dye, and the dye includes at least one organic compound as described in the first aspect, and further preferably includes at least one organic compound having the structure shown in the present invention.

[0100] As a preferred technical solution of the present invention, the organic compound, when used as a dye for the light-emitting layer, especially as a luminescent dye, has good luminescence properties, can improve the lifespan and external quantum efficiency of the device, and enable the device to have high luminescence efficiency and better color purity, which can meet the current requirements of panel and display manufacturers for high-performance materials.

[0101] The organic compound provided by the present invention can be used as a TADF material, as a dye (guest material) of the light-emitting layer, and is suitable for organic electroluminescent devices with a TADF mechanism or an organic electroluminescent device with a TASF (thermally activated sensitized fluorescence) mechanism, and can effectively improve the performance of the device. Its good carrier transport performance and high luminous efficiency have potential applications in solving the efficiency roll-off of OLED devices at high current density and extending the device life.

[0102] Preferably, the organic layer further comprises any one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, or a combination of at least two thereof.

[0103] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device according to the third aspect.

[0104] The OLED device prepared using the compound of the present invention has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturers for high-performance materials. DETAILED DESCRIPTION

[0105] The technical solution of the present invention is further described in more detail below.

[0106] Synthesis methods of compounds

[0107] In one embodiment, 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, but those skilled in the art can also obtain the compounds by other methods known to them. The synthesis route of the compounds represented by the general formula of the present invention can be, for example:

[0108]

[0109] where Y 1 To Y 4 Each independently represents a substituted or unsubstituted Z 1 to Z 15 、Z 12 ~Z 15 、X 1 ~X 4 Any of;

[0110]

[0111] or,

[0112]

[0113] Use the same synthesis method to synthesize material structures:

[0114] Use the same synthesis method to synthesize material structures:

[0115]

[0116]

[0117] or,

[0118]

[0119] Use the same synthesis method to synthesize material structures:

[0120] or

[0121]

[0122] Use the same method to synthesize the material structure:

[0123] Similarly, other material structures can be synthesized using roughly the same synthesis method, which will not be described in detail here. Alternatively, those skilled in the art can also prepare them using other methods known in the art. Compounds not mentioned in the present invention are all raw materials obtained from commercial sources, or are prepared in-house using these raw materials according to known methods.

[0124] The following synthesis examples of the present invention illustratively provide specific synthesis methods for representative compounds. The solvents, reagents, intermediates, and chemical reagents such as ethyl acetate, methanol, and ethanol used in the following synthesis examples can all be purchased or customized from the domestic chemical product market.

[0125] The present invention will describe in detail the specific preparation methods of the organic compounds described herein using a number of preparation examples and synthesis examples. However, the preparation methods of the present invention are not limited to these synthesis examples. It should be noted that obtaining the organic compounds described herein is not limited to the synthesis methods and starting materials used in the present invention. Those skilled in the art may also use other methods or routes to obtain the organic compounds described herein.

[0126] In addition, although representative exemplary synthetic routes of the compounds of the present invention are described in the Examples, those skilled in the art can also obtain the compounds by other methods known in the art.

[0127] Organic EL devices

[0128] The OLED structure of the present invention can refer to known technologies. For example, an organic electroluminescent device (OLED) includes a first electrode, a second electrode, and an organic material layer located between the electrodes. The organic material layer 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.

[0129] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate used for the display can also be provided with thin film transistors (TFTs).

[0130] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves 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 serves 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), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0131] 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.

[0132] 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 single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of the following: 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.

[0133] 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 ethylene, 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 the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0134]

[0135]

[0136]

[0137] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound or a combination of multiple compounds. For example, the hole injection layer can use one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below. Alternatively, one or more of the compounds HT-1 to HT-51 can be doped with one or more of the compounds HI-1 to HI-3 described below.

[0138]

[0139] The light-emitting layer includes a luminescent dye (i.e., a dopant) that can emit light at different wavelengths, and may also include a host material. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or red. Multiple monochromatic light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and red.

[0140] Depending on the technology, the light-emitting layer material can be made of fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, and other materials. An OLED device can use a single light-emitting technology or a combination of multiple technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0141] 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.

[0142]

[0143] In one aspect of the present invention, the barrier layer surrounding the light-emitting layer can be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0144]

[0145]

[0146]

[0147]

[0148] In one aspect of the present invention, an electron blocking layer (EBL) is positioned between the hole transport layer and the light emitting layer. The EBL can be composed of, but is 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.

[0149] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. This region may be a single-layer electron transport layer (ETL), including those containing only one compound and those containing multiple compounds. The region may also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0150] 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.

[0151]

[0152]

[0153]

[0154]

[0155] In one aspect of the present invention, a hole-blocking layer (HBL) is positioned between the electron-transporting layer and the light-emitting layer. The hole-blocking layer may be composed of, 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, or a mixture of, but not limited to, one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46.

[0156] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0157] Specific examples are described below. Those skilled in the art should understand that the examples are only provided to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0158] Example

[0159] Synthesis of compounds

[0160] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using multiple synthesis examples as examples, but the preparation methods of the present invention are not limited to these synthesis examples. It should be noted that obtaining the compounds is not limited to the synthesis methods and raw materials used in the present invention, and those skilled in the art can also choose other methods or routes to obtain the compounds proposed by the present invention. The compounds of the synthesis methods not mentioned in the present invention are all raw materials obtained through commercial channels, or are made by self-production according to known methods using 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 Sinopharm 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). The structural analysis and detection of the intermediates and compounds in the present invention uses a gas chromatography-mass spectrometer (GC-MS, Shimadzu QP2010 SE).

[0161] The following examples describe methods for synthetically preparing specific compounds of the present invention.

[0162] Synthesis Example (1): Synthesis of Intermediate A1

[0163]

[0164] Experimental Procedure: Add 100 g of spiro[5.5]undecan-3-one to a 3 L single-necked flask, followed by 1 L of THF. Slowly add 360 mL of a 2.5 M THF solution of methylmagnesium bromide at -10°C under nitrogen. Return the mixture to room temperature and stir for 2 hours. Add 1 L of saturated brine, separate the liquids, dry them, concentrate them, and purify them by vacuum distillation to obtain the target intermediate A1 (97.55 g). MS: 182.17 / 182.83 (calcd / measured).

[0165] Synthesis Example (2): Synthesis of Intermediate A2

[0166]

[0167] Experimental procedure: Intermediate A2 (100.63 g) was synthesized by referring to the method for synthesizing intermediate A1. MS: 142.14 / 142.53 (calculated / found).

[0168] Synthesis Example (3): Synthesis of Intermediate B1

[0169]

[0170] Experimental Procedure: Intermediate A2 (100 g) and phenol (66.16 g) were placed in a 3-L single-necked flask. 1 L of toluene was then added, followed by the slow addition of boron trifluoride etherate (149.67 g) at 0°C. The reaction was allowed to react overnight at room temperature. The next day, the mixture was washed with 1 L of saturated brine, concentrated, and purified by vacuum distillation to yield the target intermediate B1 (102.86 g). MS: 218.17 / 218.85 (calcd / measured).

[0171] Synthesis Example (4): Synthesis of Intermediate B2

[0172]

[0173] Experimental procedure: Intermediate B2 (113.34 g) was synthesized by referring to the method for synthesizing intermediate B1. MS: 176.12 / 176.25 (calculated value / found value).

[0174] Synthesis Example (5): Synthesis of Intermediate B3

[0175]

[0176] Experimental procedure: Intermediate B3 (96.33 g) was synthesized by referring to the method for synthesizing intermediate B1. MS: 258.20 / 258.81 (calculated value / found value).

[0177] Synthesis Example (6): Synthesis of Intermediate B4

[0178]

[0179] Experimental Procedure: Intermediate B1 (100 g) and triethylamine (69.52 g) were placed in a 1 L single-necked flask and dissolved in 500 mL of dichloromethane. Trifluoromethanesulfonic anhydride (155.06 g) was then slowly added at 0°C. After the addition was complete, the mixture was returned to room temperature and allowed to react for 3 hours. Then, 300 mL of saturated brine was added, the mixture was separated, dried, concentrated, and purified by column chromatography to obtain the target intermediate B4 (114.3 g). MS: 350.12 / 350.54 (calcd / measured).

[0180] Synthesis Example (7): Synthesis of Intermediate B5

[0181]

[0182] Experimental procedure: Intermediate B5 (128.61 g) was synthesized by referring to the method for synthesizing intermediate B4. MS: 308.07 / 308.56 (calculated value / found value).

[0183] Synthesis Example (8): Synthesis of Intermediate B6

[0184]

[0185] Experimental procedure: Intermediate B6 (103.69 g) was synthesized by referring to the method for synthesizing intermediate B4. MS: 390.15 / 390.67 (calculated value / found value).

[0186] Synthesis Example (9): Synthesis of Intermediate B7

[0187]

[0188] Experimental procedures: Intermediate B4 (100 g), benzophenone imine (77.59 g), Pd2(dba)3 (13 g), S-Phos (17.57 g), and cesium carbonate (185.97 g) were placed in a 2-L three-necked flask. 1 L of 1,4-dioxane was added and the mixture was heated at 100°C under nitrogen for 10 hours. Heating was stopped, the mixture was filtered, and the filtrate was added with 200 mL of concentrated hydrochloric acid and reacted at 70°C for 3 hours. The mixture was then evaporated to dryness under reduced pressure, washed with 200 mL of petroleum ether and then 200 mL of toluene, filtered, and dried to obtain the target product (hydrochloride salt). The target product was dissolved in 300 mL of dichloromethane, washed with 200 mL of saturated sodium carbonate solution, separated, concentrated, and purified by distillation under reduced pressure to obtain the target intermediate B7 (48.56 g, 78.28%). MS: 217.18 / 217.84 (calcd / measured).

[0189] Synthesis Example (10): Synthesis of Intermediate B8

[0190]

[0191] Experimental procedure: Intermediate B8 (45.62 g, 80.24%) was synthesized by referring to the method for synthesizing intermediate B7. MS: 175.14 / 175.63 (calculated value / found value).

[0192] Synthesis Example (11): Synthesis of Intermediate B9

[0193]

[0194] Experimental procedure: Intermediate B9 (44.38 g, 67.31%) was synthesized by referring to the method for synthesizing intermediate B7. MS: 257.21 / 257.74 (calculated value / found value).

[0195] Synthesis Example (12): Synthesis of Intermediate B10

[0196]

[0197] Experimental Procedure: 2-bromo-4-tert-butylaniline (50 g), 4-tert-butylphenylboronic acid (46.82 g), tetrakistriphenylphosphine palladium (5.07 g), and potassium carbonate (45.44 g) were added to a 1-L three-necked flask. A 5:1 mixture of 1,4-dioxane and water (300 mL) was added. The mixture was reacted at 100°C under nitrogen for 10 hours. The mixture was then cooled to room temperature, the organic phase was concentrated, and purified by column chromatography to yield the target intermediate B10 (46.82 g). MS: 281.21 / 281.54 (calcd / measured).

[0198] Synthesis Example (13): Synthesis of Intermediate B11

[0199]

[0200] Experimental procedure: Intermediate B11 (47.26 g) was synthesized by referring to the method for synthesizing intermediate B10. MS: 335.26 / 335.75 (calculated value / found value).

[0201] Synthesis Example (14): Synthesis of Intermediate B12

[0202]

[0203] Experimental procedure: Intermediate B12 (50.84 g) was synthesized by referring to the method for synthesizing intermediate B10. MS: 337.28 / 337.55 (calculated value / found value).

[0204] Synthesis Example (15): Synthesis of Intermediate B13

[0205]

[0206] Experimental procedure: Intermediate B13 (48.66 g) was synthesized by referring to the method for synthesizing intermediate B10. MS: 225.15 / 225.34 (calculated value / found value).

[0207] Synthesis Example (16): Synthesis of Intermediate C1

[0208]

[0209] Experimental procedures: Intermediate B7 (50 g) was placed in a 2 L single-necked flask, followed by 500 mL of THF. NBS (102.36 g) was then slowly added at 0°C. After complete addition, the mixture was returned to room temperature. After 2 hours of reaction at room temperature, 200 mL of saturated brine was added. The washed fractions were concentrated and purified by column chromatography to obtain the target intermediate C1 (69.34 g). MS: 373.00 / 373.15 (calculated / measured).

[0210] Synthesis Example (17): Synthesis of Intermediate C2

[0211]

[0212] Experimental procedure: Intermediate C2 (61.23 g) was synthesized by referring to the method for synthesizing intermediate C1. MS: 331.00 / 331.21 (calculated value / found value).

[0213] Synthesis Example (18): Synthesis of Intermediate C3

[0214]

[0215] Experimental Procedure: Intermediate C1 (50 g) was added to a 1 L three-necked flask, along with CuCl2 (35.84 g) and 300 mL of acetonitrile. The mixture was heated at 60°C for 1 hour, then returned to room temperature. Tert-butyl nitrite (20.62 g) was slowly added dropwise to the reaction system. After the addition was complete, the mixture was heated at 60°C for 3 hours. Heating was then stopped and the reaction system was added to 1 L of water. A large amount of solid precipitated, which was filtered and recrystallized once from dichloromethane + methanol to yield the target intermediate C3 (38.36 g). MS: 392.02 / 392.67 (calcd / measured).

[0216] Synthesis Example (19): Synthesis of Intermediate C4

[0217]

[0218] Experimental procedure: Intermediate C4 (37.43 g) was synthesized by referring to the synthesis procedure of intermediate C3. MS: 350.04 / 350.39 (calculated value / found value).

[0219] Synthesis Example (20): Synthesis of Material C5

[0220]

[0221] Experimental procedures: Intermediate B7 (30 g), 3-bromo-5-(tert-butyl)benzo[B]thiophene (37.16 g), Pd(dppf)Cl2 (2.02 g), and sodium tert-butoxide (19.90 g) were placed in a 1 L single-necked flask. 200 mL of toluene was added and the mixture was reacted at 100°C under nitrogen for 15 hours. Heating was then stopped and the reaction system was diluted with 200 mL of dichloromethane and washed with 300 mL of water. The mixture was separated, dried, concentrated, and purified by column chromatography to obtain the target intermediate C5 (40.23 g). MS: 405.25 / 405.77 (calcd / measured).

[0222] Synthesis Example (21): Synthesis of Material C6

[0223]

[0224] Experimental procedure: Intermediate C6 (39.27 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 363.20 / 363.56 (calculated value / found value).

[0225] Synthesis Example (22): Synthesis of Material C7

[0226]

[0227] Experimental procedure: Intermediate C7 (41.59 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 337.19 / 337.53 (calculated value / found value).

[0228] Synthesis Example (23): Synthesis of Intermediate C8

[0229]

[0230] Experimental procedure: Intermediate C8 (40.22 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 391.23 / 391.62 (calculated value / found value).

[0231] Synthesis Example (24): Synthesis of Intermediate C9

[0232]

[0233] Experimental procedure: Intermediate C9 (38.26 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 469.28 / 469.54 (calculated value / found value).

[0234] Synthesis Example (25): Synthesis of Intermediate C10

[0235]

[0236] Experimental procedure: Intermediate C10 (40.84 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 523.33 / 523.82 (calculated value / found value).

[0237] Synthesis Example (26): Synthesis of Intermediate C11

[0238]

[0239] Experimental procedure: Intermediate C11 (33.45 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 469.37 / 469.76 (calculated value / found value).

[0240] Synthesis Example (27): Synthesis of Intermediate C12

[0241]

[0242] Experimental procedure: Intermediate C12 (35.16 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 413.31 / 413.68 (calculated value / found value).

[0243] Synthesis Example (28): Synthesis of Intermediate C13

[0244]

[0245] Experimental procedure: Intermediate C13 (33.94 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 467.36 / 467.74 (calculated value / found value).

[0246] Synthesis Example (29): Synthesis of Intermediate C14

[0247]

[0248] Experimental procedure: Intermediate C14 (34.21 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 403.23 / 403.65 (calculated value / found value).

[0249] Synthesis Example (30): Synthesis of Intermediate C15

[0250]

[0251] Experimental procedure: Intermediate C15 (32.37 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 389.31 / 389.63 (calculated value / found value).

[0252] Synthesis Example (31): Synthesis of Intermediate C16

[0253]

[0254] Experimental procedure: Intermediate C16 (37.85 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 445.28 / 445.71 (calculated value / found value).

[0255] Synthesis Example (32): Synthesis of Intermediate C17

[0256]

[0257] Experimental procedure: Intermediate C17 (35.73 g) was synthesized by referring to the synthesis procedure of intermediate C5. MS: 383.26 / 383.58 (calculated value / found value).

[0258] Synthesis Example (33): Synthesis of Intermediate D1

[0259]

[0260] Experimental procedures: Intermediate C3 (25 g), intermediate C11 (30 g), Pd2(dba)3 (1.16 g), S-Phos (1.30 g), and sodium tert-butoxide (9.13 g) were placed in a 1 L single-necked flask. 200 mL of toluene was added and the mixture was reacted at 100°C under nitrogen for 3 hours. Heating was then stopped and the mixture was diluted with 200 mL of dichloromethane. The fraction was washed with water, dried, concentrated, and purified by column chromatography to obtain the target intermediate D1 (36.64 g). MS: 781.40 / 781.62 (calcd / measured).

[0261] Synthesis Example (34): Synthesis of Intermediate D2

[0262]

[0263] Experimental procedure: Intermediate D2 (35.69 g) was synthesized by referring to the synthesis procedure of intermediate D1. MS: 683.29 / 683.54 (calculated value / found value).

[0264] Synthesis Example (35): Synthesis of Intermediate D3

[0265]

[0266] Experimental procedure: Intermediate D3 (38.11 g) was synthesized by referring to the synthesis procedure of intermediate D1. MS: 657.27 / 657.53 (calculated value / found value).

[0267] Synthesis Example (36): Synthesis of Intermediate D4

[0268]

[0269] Experimental procedure: Intermediate D4 (34.98 g) was synthesized by referring to the synthesis procedure of intermediate D1. MS: 627.23 / 627.44 (calculated value / found value).

[0270] Synthesis Example (37): Synthesis of Intermediate D5

[0271]

[0272] Experimental procedure: Intermediate D5 (38.07 g) was synthesized by referring to the synthesis procedure of intermediate D1. MS: 647.29 / 647.80 (calculated value / found value).

[0273] Synthesis Example (38): Synthesis of Intermediate D6

[0274]

[0275] Experimental procedure: Intermediate D6 (37.21 g) was synthesized by referring to the synthesis procedure of intermediate D1. MS: 633.27 / 633.16 (calculated value / found value).

[0276] Synthesis Example (39): Synthesis of Intermediate D7

[0277]

[0278] Experimental procedure: Intermediate D7 (36.02 g) was synthesized by referring to the synthesis procedure of intermediate D1. MS: 711.32 / 711.53 (calculated value / found value).

[0279] Synthesis Example (40): Synthesis of Intermediate E1

[0280]

[0281] Experimental procedures: Intermediate D1 (20 g), intermediate C8 (10 g), catalyst Pd2(dba)3 (1.05 g), sodium tert-butoxide (3.68 g), and S-Phos (2.09 g) were placed in a 500 mL single-necked flask. 200 mL of toluene was added and the mixture was reacted at 100°C under nitrogen for 3 hours. Heating was then stopped, the separated liquid was washed with water, dried, concentrated, and purified by column chromatography to obtain the target intermediate E1 (18.87 g). MS: 1092.71 / 1092.85 (calculated / measured).

[0282] Synthesis Example (41): Synthesis of Intermediate E2

[0283]

[0284] Experimental procedure: Intermediate E2 (19.04 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 1072.64 / 1072.05 (calculated value / found value).

[0285] Synthesis Example (42): Synthesis of Intermediate E3

[0286]

[0287] Experimental procedure: Intermediate E3 (17.82 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 940.55 / 940.84 (calculated value / found value).

[0288] Synthesis Example (43): Synthesis of Intermediate E4

[0289]

[0290] Experimental procedure: Intermediate E4 (18.16 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 884.49 / 884.82 (calculated value / found value).

[0291] Synthesis Example (44): Synthesis of Intermediate E5

[0292]

[0293] Experimental procedure: Intermediate E5 (19.08 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 1090.69 / 1090.78 (calculated value / found value).

[0294] Synthesis Example (45): Synthesis of Intermediate E6

[0295]

[0296] Experimental procedure: Intermediate E6 (18.92 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 1022.63 / 1022.95 (calculated value / found value).

[0297] Synthesis Example (46): Synthesis of Intermediate E7

[0298]

[0299] Experimental procedure: Intermediate E7 (18.57 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 1076.67 / 1076.89 (calculated value / found value).

[0300] Synthesis Example (47): Synthesis of Intermediate E8

[0301]

[0302] Experimental procedure: Intermediate E8 (17.96 g) was synthesized by referring to the synthesis procedure of intermediate E1. MS: 1036.64 / 1036.75 (calculated value / found value).

[0303] Synthesis Example (48): Synthesis of Final Product M-6

[0304]

[0305] Experimental procedures: Intermediate E1 (15 g) was added to a 500 mL three-necked flask, followed by 200 mL of ultra-dry xylene. Tert-butyl lithium (22 mL) was slowly added at -60°C under nitrogen protection. The mixture was then returned to room temperature and heated to 60°C for activation for 2 hours. The temperature was then lowered to -60°C, followed by the addition of boron tribromide (10.30 g) and DIEA (7.09 g). The mixture was then returned to room temperature and heated to 100°C for 10 hours. The reaction mixture was then returned to room temperature. 100 mL of dichloromethane and 100 mL of water were added to the reaction system. The separated liquid was washed with water, dried, concentrated, and purified by column chromatography to obtain the target final product M-6 (3.32 g). MS: 1066.47 / 1066.73 (calcd / measured).

[0306] Synthesis Example (49): Synthesis of Final Product M-17

[0307]

[0308] Experimental procedure: Referring to the synthesis procedure of the final product M-6, the final product M-17 (2.95 g) was synthesized. MS: 1046.67 / 1046.82 (calculated value / found value).

[0309] Synthesis Example (50): Synthesis of Final Product M-38

[0310]

[0311] Experimental procedure: Referring to the synthesis procedure of the final product M-6, the final product M-38 (3.12 g) was synthesized. MS: 914.57 / 914.83 (calculated value / found value).

[0312] Synthesis Example (51): Synthesis of Final Product M-56

[0313]

[0314] Experimental procedure: Referring to the synthesis procedure of the final product M-6, the final product M-56 (3.53 g) was synthesized. MS: 858.51 / 858.76 (calculated value / found value).

[0315] Synthesis Example (52): Synthesis of Final Product M-95

[0316]

[0317] Experimental procedure: The final product M-95 (2.94 g) was synthesized by referring to the synthesis procedure of the final product M-6. MS: 1064.72 / 1064.93 (calculated value / found value).

[0318] Synthesis Example (53): Synthesis of Final Product M-102

[0319]

[0320] Experimental procedure: The final product M-102 (3.17 g) was synthesized by referring to the synthesis procedure of the final product M-6. MS: 996.65 / 996.86 (calculated value / found value).

[0321] Synthesis Example (54): Synthesis of Final Product M-112

[0322]

[0323] Experimental procedure: The final product M-112 (2.94 g) was synthesized by referring to the synthesis procedure of the final product M-6. MS: 1050.70 / 1050.83 (calculated value / found value).

[0324] Synthesis Example (55): Synthesis of Final Product M-119

[0325]

[0326] Experimental procedure: The final product M-119 (3.02 g) was synthesized by referring to the synthesis procedure of the final product M-6. MS: 1010.67 / 1010.91 (calculated value / found value).

[0327] Device Examples

[0328] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0329] Glass plates coated with an ITO transparent conductive layer were ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0330] Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a pressure less than 1*10 -5 Pa, a mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above-mentioned anode layer as a hole injection layer at a deposition rate of 0.1 nm / s and a film thickness of 10 nm;

[0331] HT-4 was vacuum evaporated on the hole injection layer as the hole transport layer of the device at a deposition rate of 0.1 nm / s and a total film thickness of 60 nm.

[0332] HT-14 was vacuum-deposited on the hole transport layer as the electron blocking layer of the device at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0333] The light-emitting layer of the device is vacuum-deposited on the electron blocking layer. The light-emitting layer includes a host material and a dye material. A 20 nm thick binary mixture of compound BFH-4 and fluorescent dye (100:3, w / w) is deposited as the light-emitting layer by a multi-source co-evaporation method. The fluorescent dye is compound M-6 of the present invention.

[0334] 5 nm of ET-23 was vacuum-deposited on the light-emitting layer as a hole-blocking layer, and 25 nm of a mixture of compounds ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited as an electron-transporting layer at a rate of 0.1 nm / s.

[0335] LiF with a thickness of 1 nm was vacuum evaporated on the electron transport layer as the electron injection layer, and 150 nm of metal aluminum was used as the cathode. The total evaporation rate of LiF was controlled at 0.1 nm / s, and the evaporation rate of the metal electrode was controlled at 1 nm / s.

[0336] Device Examples 2 to 16 and Device Comparative Examples 1 to 9:

[0337] Device Examples 2 to 16 were prepared in the same manner as in Device Example 1, except that the luminescent dye in the luminescent layer was replaced by the compounds of the present invention listed in Table 1 instead of the compound M-6 of the present invention.

[0338] Device Comparative Examples 1 to 9 were prepared using the same method as that of Device Example 1, except that the luminescent dye in the luminescent layer was replaced by the compound M-6 of the present invention with the following compounds N1 to N9 obtained using prior art or according to a similar preparation process to the synthesis examples of the present invention. The specific structures are shown below:

[0339]

[0340] In the comparative compounds, the N1 substituent contains benzyl hydrogen, which is unstable when the device is in working condition and affects the device life; N2 does not have a benzothiophene structure, and the triplet energy level is relatively high, which easily causes triplet exciton quenching, affecting efficiency and life. At the same time, the stability of 1-methylcyclohexyl is not as good as 1,4,4-trimethylcyclohexyl, resulting in a relatively low life; N3 also has the problem of low stability of 1-methylcyclohexyl, and at the same time, there is no alkyl protection at the 3-position of benzothiophene, which also leads to a low life of the material. In the comparative example, N4, N6, and N7 all have benzyl hydrogen in their structures, which will undergo degradation reactions with holes in the device; although N9 has been deuterated, degradation reactions will still occur; the dominant conformation of the 1-methylcyclohexyl in N5 does not have the effect of improving the external quantum efficiency of the material, so the device efficiency is low; the para-fused benzene ring structure of the B atom in N8 is unstable, resulting in a low device life.

[0341] Device test method (including equipment and test conditions):

[0342] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0343] The external quantum efficiency (EQE%) of the organic electroluminescent device was measured using an integrating sphere; the external quantum efficiency of the device in comparative example 1 was set to 1.0, and the external quantum efficiencies of the other materials were all ratios thereof;

[0344] The life test of LT97 is as follows: Use a luminance meter at 40mA / cm 2 Initial brightness of the device at a given current density. Maintaining a constant current, measure the time (in hours) for the device brightness to drop to 97% of its initial brightness. Taking the LT97 lifetime test value of Comparative Example 1 as 1.0, calculate the ratio of the LT97 lifetime test values ​​of the other devices to that of Comparative Example 1.

[0345] The performance of the organic electroluminescent devices prepared in the above device embodiments and comparative examples is shown in Table 1 below.

[0346] Table 1:

[0347]

[0348]

[0349] As shown in Table 1, when the material schemes and preparation processes of the other functional layers in the organic electroluminescent device structure are identical, the organic electroluminescent devices prepared in Examples 1-16 of the present invention effectively maintain substantially the same operating voltage compared to the organic electroluminescent devices prepared in Comparative Examples 1-9. External quantum efficiencies generally increase, with the highest increase reaching approximately 15%. This is presumably due to improved molecular-level dipole orientation, which increases the device's light extraction rate and, therefore, efficiency. Furthermore, 1-methylspiro[5.5]undecyl and 1,4,4-trimethylcyclohexyl are more stable than cyclohexyl, 1-methylcyclohexyl, and 1-methylcyclopentyl groups, resulting in significantly extended device lifetimes in Examples 8, 9, 10, and 11.

[0350] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above are only specific embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

[0351] 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 ingredients, the selection of specific methods, etc., all fall within the scope of protection and disclosure of the present invention.

Claims

1. A boron-nitrogen-containing organic compound having a structure shown in formula (1): In formula (1), Rings A, B, C, E, and F are each independently selected from a C6-C60 aromatic ring and a C3-C60 heteroaromatic ring; R 7 In the ortho position of the N-substituted ring E, R 8 In the ortho position of the N-substituted ring F, R 7 and R 8 are independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 7 and R 8 At least one of the following is selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; R A 、R B 、R C 、R E 、R F represents single substitution to maximum substitution, R A 、R B 、R C 、R E 、R F Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R A 、R B 、R C 、R E 、R F are independently connected to each other by chemical bonds to form a ring or are not connected; wherein R A 、R B 、R C 、R E 、R F At least one of them is a structure of formula (a) or formula (b), In formula (a) or formula (b), R 1 、R 2 、R 3 、R 4 、R 5 、R 6 are independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, R 1 、R 2 Connect or not connect; R 3 、R 4 Connect or not connect, R 5 、R 6 Connect or not connect; the condition is, R 1 and R 2 Among them, at least one is not hydrogen; Ra and Rb are independently selected from substituted or unsubstituted C1-C20 chain alkyl groups; Y 1 and Y 2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; The above-mentioned substituents are each independently selected from any one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, cyano, nitro, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. 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, and the * indicates the connection site.

2. The boron-nitrogen-containing organic compound according to claim 1, characterized in that Ring A and Ring B have the structure shown in Formula (d) or Formula (e): Among them, the dotted line represents the fused bond of the group; In formula (e), X represents O, S, NR 0 、C(R 0 )2; In formula (d) and formula (e), Z 12 ~Z 15 、X 1 ~X 4 are independently selected from CR or N, Among them, each R 0 , R are independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, halogen, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, R 0 They are connected to each other by chemical bonds to form a ring or not, and R are connected to each other by chemical bonds to form a ring or not; The ring C has a structure as shown in formula (f): Wherein, the dotted line represents the fused bond of the group; Z 5 ~Z 7 Each independently is CR or N; R is independently selected from any one of hydrogen, halogen, cyano, nitro, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; R is not connected to adjacent ring structures or is connected to form a ring through chemical bonds; The above-mentioned substituents are each independently selected from any one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, cyano, nitro, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof.

3. The organic compound according to claim 1, characterized in that It has a structure as shown in the following formula (1-1) or formula (1-2): In formula (1-1) and formula (1-2), R 7 and R 8 The meaning of expression is the same as in formula (1); Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 are independently selected from CR or N, R is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 heterocycloalkyl, halogen, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 Any two adjacent R in are connected to form a ring or not; and Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 There is at least one connection structure (a) or (b); X represents O or S; Preferably, in formula (1-1), Z 2 、Z 3 、Z 6 、Z 9 、Z 10 、Z 13 、Z 14 、Z 13’ 、Z 14’ At least one of them is connected to formula (a) or formula (b); Preferably, in formula (1-2), Z 2 、Z 3 、Z 6 、Z 9 、Z 10 、Z 13 、Z 14 、X 2 、X 3 At least one of them is connected to formula (a) or formula (b), Preferably, Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 Any two adjacent R in are connected to form the following structure: * indicates the connection site; The above-mentioned substituents are each independently selected from any one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, cyano, nitro, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof.

4. The organic compound according to claim 3, characterized in that Having any of the structures shown in the following formulas (2-1) to (2-16): X represents O or S, preferably S; Z 1 ~Z 15 、Z 12’ ~Z 15’ 、X 1 ~X 4 The meaning of expression is the same as in formula (1-1) and formula (1-2); R 1 、R 2 、R 3 、R 4 、R 5 、R 6 The meanings of expressions are the same as those in formula (a) and formula (b).

5. The boron-nitrogen-containing organic compound according to any one of claims 1 to 4, characterized in that R 1 ~R 6 Each is independently H, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, cyclopentyl, cyclohexyl, and any one of the following groups: where R 1 and R 2 At least one of them is not hydrogen, * indicates the connection site, and the structure with two * indicates R 1 ~R 6 The two connections in form this structure.

6. The boron-nitrogen-containing organic compound according to any one of claims 1 to 5, characterized in that R 7 and R 8 Any one selected from H and the following groups, * indicates the connection site.

7. The boron-nitrogen-containing organic compound according to claim 4, characterized in that In formulas (2-1) to (2-16), Z 1 、Z 2 、Z 4 、Z 5 、Z 7 、Z 8 、Z 10 ~Z 12 、Z 12’ 、Z 15 、Z 15’ CH, Z 3 、Z 6 、Z 9 、Z 13 、Z 14 、Z 13’ 、Z 14’ is CR, and R is each independently selected from H, fluorine, chlorine, nitro, cyano, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, 2,2,5,5-tetramethylhexyl, phenyl, naphthyl, tert-butylphenyl, pyridine, pyrimidine, or one of the following groups: and / or In formulas (2-1) to (2-12), X 1 、X 4 CH, X 2 、X 3 CR, R are each independently selected from one of H, methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, 2,2,5,5-tetramethylhexyl, phenyl, naphthyl, tert-butylphenyl, pyridine and pyrimidine.

8. The boron-nitrogen-containing organic compound according to claim 1, comprising the following specific compounds:

9. Use of the organic compound according to any one of claims 1 to 8 in an organic electronic device; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the application is application as a light-emitting layer material in an organic electroluminescent device.

10. 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 organic layer contains the organic compound according to any one of claims 1 to 8; Preferably, at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 8. Preferably, the light-emitting layer comprises a host material and a dye, and the dye comprises at least one organic compound according to any one of claims 1 to 8.

11. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 10.

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