Organic compound and application thereof

Abstract

The invention relates to a boron-containing organic material, belongs to the technical field of organic luminescent materials, and also relates to an application of the compound in an organic electroluminescent device. The compound disclosed by the invention has a structure as shown in a formula (I). The compound disclosed by the invention has the characteristic of narrow spectrum emission, is beneficial to improving the luminous efficiency in a device, can effectively increase the recombination rate of excitons, and is beneficial to improving the efficiency and prolonging the service life of the device. # imgabs0 #

Description

Technical Field

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

[0002] The main way for people to obtain information is through vision, so display devices are crucial in the process of human interaction with information. Organic light-emitting diodes (OLEDs) have many advantages such as flexibility, self-luminescence, high contrast, large size, and low power consumption, and have become one of the mainstream display devices.

[0003] Among them, red and green dyes, as the three primary colors, generally contain heavy atoms such as Ir and Pt, which can theoretically achieve 100% internal quantum efficiency, high electroluminescence efficiency, and low power consumption, becoming the mainstream of current commercial display devices. However, the chromaticity and life of blue phosphorescent materials do not meet the current commercial display requirements. At present, blue light devices still use traditional fluorescent materials to achieve high color purity and long device life.

[0004] Recently, Japanese researchers such as Takuji Hatakeyama and Junji Kido reported a series of organic materials DABNA-1 (Adv. Mater. 2016, 28, 2777–2781 J. Mater. Chem. C, 2019, 7, 3082-3089) based on boron-containing resonance TADF (Thermally Activated Delayed Fluorescence). The boron atoms, nitrogen atoms and phenyl groups of this type of compound constitute a rigid polycyclic aromatic skeleton, thus having a higher fluorescence quantum yield. Compared with traditional blue fluorescent dyes, this type of compound has a narrower spectrum and high color purity. However, the rigid planar structure also leads to a large difference in energy levels between the singlet and triplet states, and the reverse intersystem crossing from the triplet state to the singlet state is slow. After the excitons recombine on the dye, they will cause severe efficiency roll-off and the device life is short. In addition, an overly planar rigid structure often leads to adverse effects such as spectral broadening and red shift due to excessive doping concentration.

[0005]

[0006] Existing organic electroluminescent materials still have a lot of room for improvement in terms of luminescence performance, and the industry urgently needs to develop new luminescent material systems to meet commercial needs. Boron-containing resonance-type materials have the advantages of high color purity and high luminescence efficiency, which has attracted widespread attention from the scientific research and industry. However, due to the relatively planar structural characteristics of resonance-type dyes, they are prone to molecular aggregation, which reduces color purity and leads to reduced device performance. Summary of the invention

[0007] To solve the above problems, the present invention provides an organic compound, specifically a condensed ring organic compound, having a structure as shown in formula (I):

[0008]

[0009] Wherein, ring A is a structure represented by formula (a); R 21 With R 22 Connected or not connected;

[0010] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 21 , R 22 Each is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C4-C30 alkylsilyl, substituted or unsubstituted C2-C30 alkylamino, substituted or unsubstituted C4-C30 cycloalkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aromatic boron, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0011] R1~R 13 , R 21 , R 22 Two adjacent ones are connected or not connected;

[0012] R1~R 13 wherein at least one of the compounds has a structure as described in formula (b);

[0013] In formula (a), the dotted line represents the position of the fused connection; M is selected from NR 18 , O, S or CR 19 R 20 ;

[0014] R 18 , R 19 , R 20 are each independently selected from one of a C1-C36 chain alkyl group, a C3-C36 cycloalkyl group, a C6-C30 arylamino group, a C6-C60 aryl group, a C6-C60 aryloxy group, and a C5-C60 heteroaryl group; and R 19 With R20 Connected or not connected;

[0015] R 14 , R 15 , R 16 , R 17 Each is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C4-C30 alkylsilyl, substituted or unsubstituted C2-C30 alkylamino, substituted or unsubstituted C4-C30 cycloalkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aromatic boron, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0016] In formula (b), *—represents the connection site; R 35 With R 36 No connection between them, or R 35 With R 36 Through single bond, O, S, CR 31 R 32 or SiR 33 R 34 connect;

[0017] R 31 , R 32 , R 33 , R 34 are each independently selected from one of a C1-C10 chain alkyl group, a C3-C10 cycloalkyl group, a C6-C30 arylamino group, a C6-C60 aryl group, a C6-C60 aryloxy group, and a C5-C60 heteroaryl group; and R 31 With R 32 Connect or not connect between them, and R 33 With R 34 Connected or not connected;

[0018] R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 35 , R 36Each is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C4-C30 alkylsilyl, substituted or unsubstituted C2-C30 alkylamino, substituted or unsubstituted C4-C30 cycloalkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aromatic boron, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0019] When the above R1-R 17 , R 21 -R 30 , R 35 , R 36 When substituents are independently present on the above, the substituents are independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C60 aromatic boron, and C3-C30 heteroaryl.

[0020] It should be noted that the meanings of all technical and scientific terms used herein are intended to be the same as those commonly understood by those skilled in the art, including those technical changes or replacements with equivalent technologies that are obvious to those skilled in the art.

[0021] In this specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent. When describing C1 to 30, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.

[0022] 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.

[0023] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes with the same chemical properties. For example, the expression "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes 12 C. 13 C, etc., no further details.

[0024] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably N, O and S.

[0025] As used herein, the terms "heterocyclyl", "heteroaryl" 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 which is a heteroatom selected from N, O and S and the remaining ring atoms being C.

[0026] As used herein, the terms "(ylidene)aryl" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "(ylidene)heteroaryl" and "heteroaromatic ring" refer to a monocyclic, bicyclic or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably refers to an alkyl substituted with an aryl or heteroaryl group, wherein the aryl, heteroaryl and alkyl groups are as defined herein.

[0027] As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

[0028] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced by a selection from the indicated group, provided that the normal valence of the designated atom in the present context is not exceeded and the substitution forms a stable compound. Combinations of substituents and / or variables are permitted only if such combinations form stable compounds.

[0029] 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.

[0030] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0031] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0032] 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.

[0033] The term "about" means within ±10% of the stated numerical value, preferably within ±5%, more preferably within ±2%.

[0034] In the structural formula disclosed in this specification, the expression of “—” crossing over a ring structure indicates that the connection site is at any position on the ring structure that can form a bond.

[0035] In the present specification, the substituted or unsubstituted C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl. The C6-C60 aryl group of the present invention can also be a group formed by combining the above groups by single bond connection or / and fusion.

[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-oxadiazolyl, 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-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole. The C3-C60 heteroaryl group of the present invention may also be a group formed by combining the above groups by single bond connection or / and fusion.

[0037] In this specification, the chain alkyl group includes both straight-chain and branched alkyl groups. Examples of the C1-C20 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl.

[0038] In the present specification, the C3-C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like.

[0039] The number of carbon atoms of the C2-C20 straight-chain or cyclic alkenyl group is preferably 2 to 10. Specific examples include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0040] The number of carbon atoms in the C2-C20 straight-chain or cyclic alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[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, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0043] In the present specification, examples of C1-C20 silyl groups include silyl groups substituted with the groups listed above for the C1-C20 alkyl groups, i.e., groups formed by replacing one, two or three hydrogen atoms on the silyl group with the above-mentioned chain alkyl or cycloalkyl groups. Specifically, groups include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0044] Furthermore, the compound of the present invention has a structure shown in the following formula (II-a) or (II-b):

[0045]

[0046] Where R1~R 17 , the range of M is the same as that in formula (Ⅰ);

[0047] R 21 With R22 The two devices are connected or not connected by a single key.

[0048] Furthermore, the compound of the present invention has a structure shown in the following formula (II-c) or (II-d):

[0049]

[0050] Where R1~R 17 The defined ranges of M are the same as those in formula (I).

[0051] Preferably, R1~R 17 , R 21 , R 22 Each is independently selected from one or a combination of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C4-C10 cycloalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl; more preferably, R1-R 17 , R 21 , R 22 Each is independently selected from one of hydrogen, deuterium, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl and imidazolyl.

[0052] More preferably, in the above formula (I), (II-a), (II-b), (II-c), (II-d), R1, R2, R5, R6, R 11 , R 12 , R 13 At least one of them has a structure as described in formula (b); More preferably, R1, R6, R 12 At least one of them has a structure as described in formula (b).

[0053] Preferably, formula (b) has a structure as described in formula (b-1);

[0054]

[0055] In formula (b-1), L represents a single bond, and p is 0 or 1; when p is 0, L does not exist;

[0056] Or L for O, S, CR 31 R 32 or SiR 33 R 34 , p is 1, the R 31 , R 32 , R 33 , R 34 Each is independently selected from one of a C1-C10 chain alkyl group, a C6-C60 aryl group, and a C5-C60 heteroaryl group.

[0057] More preferably, R in formula (b) 35 , R 36 Connect via a single button as follows:

[0058]

[0059] Preferably, in the above formula (I), (II-a), (II-b), (II-c), (II-d), R 12 It has the structure described in formula (b-1), and / or R6 has the structure described in formula (b-1).

[0060] Furthermore, in formula (b), R 23 -R 30 , R 35 , R 36 Each is independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C4-C10 cycloalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0061] Preferably, the R 23 -R 30 , R 35 , R 36Each is independently selected from one of hydrogen, deuterium, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl and imidazolyl.

[0062] The specific reason why the above-mentioned compound of the present invention has excellent performance as a luminescent dye in the luminescent layer of an organic electroluminescent device is not clear, but it is speculated that the following reasons may be the reason:

[0063] 1. The boron atom contained in the compound of the present invention has a resonance effect with the nitrogen atom in the same ring, and the strong central rigid structure is conducive to reducing the Stokes shift of the molecule, so that this series of materials has the characteristics of narrow spectrum emission, which is conducive to improving the luminous efficiency in the device;

[0064] 2. The present invention introduces a type of heterocyclic and indole substituents on one side of the boron-containing compound skeleton, which is beneficial to limit the molecular vibration and rotation, narrow the material emission spectrum, and at the same time can improve the molecular transmission capacity and enhance the carrier balance in the device;

[0065] 3. The present invention fuses a five-membered heterocyclic ring on one side of the B / N mother core and a six-membered ring on the other side, so that the material has a more suitable HOMO energy level, which can effectively increase the recombination rate of excitons and is beneficial to improving the efficiency and life of the device.

[0066] In addition, the preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, and it is suitable for mass production and expansion.

[0067] As preferred structures of the compounds of the present invention, the following specific compounds M1 to M276 can be cited, but are not limited to these compounds:

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] Another aspect of the present invention also provides an application of the compound as described above in an organic electroluminescent device. Specifically, it is preferably used as a light-emitting layer material in an organic electroluminescent device, and more preferably used as a material in the light-emitting layer in the organic electroluminescent device, and specifically can be used as a luminescent dye.

[0083] As another aspect of the present invention, an organic electroluminescent device is provided, comprising a first electrode, a second electrode and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer contains a compound of the general formula (I) as described above, or contains a compound having structures M1 to M276 as shown above.

[0084] Specifically, one embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and a first electrode, a plurality of light-emitting functional layers and a second electrode sequentially formed on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is provided between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains a compound of the general formula (I) as described above, or contains a compound of the structures M1 to M276 as shown above.

[0085] The present invention further discloses a display screen or a display panel, wherein the organic electroluminescent device as described above is adopted in the display screen or the display panel; preferably, the display screen or the display panel is an OLED display.

[0086] The present invention also discloses an electronic device, wherein the electronic device has a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device as described above.

[0087] The OLED device prepared by using the compound of the present invention has a low starting voltage and a better service life, and can meet the requirements of current panel manufacturing companies for high-performance materials. DETAILED DESCRIPTION

[0088] The specific preparation method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0089] It should be noted that obtaining the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the compound proposed in the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained through commercial channels, or are prepared by these raw materials according to known methods.

[0090] The solvents and reagents used in the present invention, such as dichloromethane, petroleum ether, ethanol, xylene, boron tribromide, carbazole, diphenylamine, and other chemical reagents, can be purchased from the domestic chemical product market, such as Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc.

[0091] The synthesis method of the compound of the present invention is briefly described below.

[0092] Synthesis Example

[0093] Synthesis route:

[0094]

[0095] The analysis and detection of the intermediates and compounds in the present invention were performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0096] Synthesis Example 1

[0097] Synthesis of compound M1:

[0098]

[0099] Synthesis of intermediate M1-1:

[0100] SM1 (15 g, 55.17 mmol), SM2 (9.23 g, 55.17 mmol), potassium carbonate (22.87 g, 165.51 mmol) and DMF (150 mL) were placed in a 500 mL three-necked flask, the atmosphere was replaced with nitrogen three times, and the temperature was raised to 70°C for reaction for 12 hours.

[0101] The reaction solution was poured into water for stirring and crystallization, filtered, and the solid was collected and dried. The intermediate M1-1 was purified by column chromatography to obtain 13.2 g of white solid.

[0102] Synthesis of intermediate M1-2:

[0103] M1-1 (13 g, 31.02 mmol), SM3 (8.76 g, 31.02 mmol), potassium carbonate (12.86 g, 93.06 mmol) and DMF (130 mL) were placed in a 500 mL three-necked flask, replaced with nitrogen three times, and heated to 100 °C for reaction for 12 hours.

[0104] The reaction solution was poured into water for stirring and crystallization, filtered, and the solid was collected and dried. The intermediate M1-2 was purified by column chromatography to obtain 19.8 g of white solid.

[0105] Synthesis of intermediate M1-3:

[0106] The intermediate M1-2 (19g, 27.88mmol) was added to a 500ml three-necked flask, and xylene (190mL) was added. The nitrogen was replaced 3 times, and the reaction system was cooled to -40°C. n-Butyl lithium (16.73mL, 41.82mmol) was added dropwise to the system, and then the temperature was raised to 50°C for reaction for 2.5 hours. The temperature of the reaction system was lowered to -40°C again, and boron tribromide (5.37mL, 55.77mmol) was added, and then the temperature was raised to 50°C for reaction for 1.5 hours. The temperature of the system was lowered to -40°C again, and diisopropylethylamine (13.86mL, 83.65mmol) was added. Finally, the reaction system was heated to 120°C for reaction for 12h.

[0107] After the reaction temperature was cooled to room temperature, xylene was removed under reduced pressure, and the remaining residue was purified by column chromatography to obtain a crude product which was recrystallized from dichloromethane / methanol to obtain 4.2 g of a yellow solid.

[0108] Synthesis of Product M1:

[0109] Intermediate M1-3 (4 g, 6.55 mmol), SM4 (1.66 g, 9.83 mmol), Pd2(dba)3 (60 mg, 0.06 mmol), S-phos (53.8 mg, 0.13 mmol), sodium tert-butoxide (944 mg, 9.83 mmol) and toluene (40 mL) were added to a 100 ml three-necked flask, replaced with nitrogen three times, and heated to reflux for reaction overnight.

[0110] After the reaction temperature was lowered to room temperature, the reaction solution was concentrated to dryness and column chromatography was performed to obtain 3.2 g of orange solid with a purity of 99.53%. The molecular ion mass determined by mass spectrometry was 698.37 (theoretical value: 698.26).

[0111] Synthesis Example 2

[0112] Synthesis of compound M10:

[0113]

[0114] Synthesis of intermediate M10-1:

[0115] The synthesis scheme was the same as that of M1-1, and 13.6 g of white solid M10-1 was obtained after column chromatography.

[0116] Synthesis of intermediate M10-2:

[0117] The synthesis scheme was the same as that of M1-2, and 20.3 g of white solid M10-2 was obtained after column chromatography.

[0118] Synthesis of intermediate M10-3:

[0119] The synthesis scheme was the same as that of M1-3, and 4.5 g of yellow solid M10-3 was obtained after column chromatography.

[0120] Synthesis of Product M10:

[0121] The synthesis scheme was the same as that of M1, and 3.5 g of orange solid was obtained by column chromatography with a purity of 99.68%. The molecular ion mass determined by mass spectrometry was 808.69 (theoretical value: 808.37).

[0122] Synthesis Example 3

[0123] Synthesis of compound M19:

[0124]

[0125] Synthesis of intermediate M19-1:

[0126] SM1 (16 g, 42.13 mmol), SM2 (16.25 g, 50.55 mmol), cuprous iodide (8.02 g, 42.13 mmol), 1,10-phenanthroline (15.18 g, 84.26 mmol), sodium tert-butoxide (12.15 g, 126.38 mmol) and toluene (160 mL) were placed in a 500 mL three-necked flask, replaced with nitrogen three times, and heated to reflux for reaction for 12 hours.

[0127] The reaction solution was cooled to room temperature, filtered through celite pad, and the filtrate was concentrated to dryness under reduced pressure. The intermediate M19-1 was purified by column chromatography to obtain 18.3 g of white solid.

[0128] Synthesis of intermediate M19-2:

[0129] The synthesis scheme was the same as that of M1-2, and 22.6 g of white solid M19-2 was obtained after column chromatography.

[0130] Synthesis of intermediate M19-3:

[0131] The synthesis scheme was the same as that of M1-3, and M19-35.6 g of yellow solid was obtained after column chromatography.

[0132] Synthesis of product M19:

[0133] The synthesis scheme was the same as that of M1, and 4.7 g of orange-yellow solid was obtained by column chromatography with a purity of 99.28%. The molecular ion mass determined by mass spectrometry was 852.48 (theoretical value: 852.34).

[0134] Synthesis Example 4

[0135] Synthesis of compound M28:

[0136]

[0137] Synthesis of intermediate M28-1:

[0138] The synthesis scheme was the same as that of M1-1, and 13.6 g of white solid M28-1 was obtained after column chromatography.

[0139] Synthesis of intermediate M28-2:

[0140] The synthesis scheme was the same as that of M1-2, and 20.3 g of white solid M28-2 was obtained after column chromatography.

[0141] Synthesis of intermediate M28-3:

[0142] The synthesis scheme was the same as that of M1-3, and 4.5 g of yellow solid M28-3 was obtained after column chromatography.

[0143] Synthesis of product M28:

[0144] The synthesis scheme was the same as that of M1, and 3.5 g of orange solid was obtained by column chromatography with a purity of 99.68%. The molecular ion mass determined by mass spectrometry was 847.59 (theoretical value: 847.47).

[0145] Synthesis Example 5

[0146] Synthesis of compound M51:

[0147]

[0148] Synthesis of intermediate M51-1:

[0149] The synthesis scheme was the same as that of M1-1, and 14.3 g of white solid M51-1 was obtained after column chromatography.

[0150] Synthesis of intermediate M51-2:

[0151] The synthesis scheme was the same as that of M1-2, and 21.3 g of white solid M51-2 was obtained after column chromatography.

[0152] Synthesis of intermediate M51-3:

[0153] The synthesis scheme was the same as that of M1-3, and 22.1 g of yellow solid M51-3 was obtained after column chromatography.

[0154] Synthesis of Product M51:

[0155] The synthesis scheme was the same as that of M1, and 3.5 g of orange solid was obtained by column chromatography with a purity of 99.36%. The molecular ion mass determined by mass spectrometry was 789.54 (theoretical value: 789.24).

[0156] Synthesis Example 6

[0157] Synthesis of compound M94:

[0158]

[0159] Synthesis of intermediate M94-1:

[0160] The synthesis scheme was the same as that of M1-1, and 15.2 g of white solid M94-1 was obtained after column chromatography.

[0161] Synthesis of intermediate M94-2:

[0162] The synthesis scheme was the same as that of M1-2, and 21.1 g of M94-2 was obtained as a white solid after column chromatography.

[0163] Synthesis of intermediate M94-3:

[0164] The synthesis scheme was the same as that of M1-3, and 4.3 g of yellow solid M94-3 was obtained after column chromatography.

[0165] Synthesis of product M94:

[0166] The synthesis scheme was the same as that of M1, and 3.4 g of orange solid was obtained by column chromatography with a purity of 99.68%. The molecular ion mass determined by mass spectrometry was 747.36 (theoretical value: 747.28).

[0167] Synthesis Example 7

[0168] Synthesis of compound M108:

[0169]

[0170] Synthesis of intermediate M108-1:

[0171] The synthesis scheme was the same as that of M1-1, and 15.5 g of white solid M108-1 was obtained after column chromatography.

[0172] Synthesis of intermediate M108-2:

[0173] The synthesis scheme was the same as that of M1-2, and 21.3 g of white solid M108-2 was obtained after column chromatography.

[0174] Synthesis of intermediate M108-3:

[0175] The synthesis scheme was the same as that of M1-3, and 4.8 g of yellow solid M108-3 was obtained after column chromatography.

[0176] Synthesis of product M108:

[0177] The synthesis scheme was the same as that of M1, and 3.6 g of orange solid was obtained by column chromatography with a purity of 99.55%. The molecular ion mass determined by mass spectrometry was 922.63 (theoretical value: 922.51).

[0178] Synthesis Example 8

[0179] Synthesis of compound M194:

[0180]

[0181] Synthesis of intermediate M194-1:

[0182] The synthesis scheme was the same as that of M1-1, and 16.2 g of white solid M194-1 was obtained after column chromatography.

[0183] Synthesis of intermediate M194-2:

[0184] The synthesis scheme was the same as that of M1-2, and 21.8 g of M194-2 was obtained as a white solid after column chromatography.

[0185] Synthesis of intermediate M194-3:

[0186] The synthesis scheme was the same as that of M1-3, and 5.1 g of yellow solid M194-3 was obtained after column chromatography.

[0187] Synthesis of product M194:

[0188] The synthesis scheme was the same as that of M1, and 4.1 g of orange solid was obtained by column chromatography with a purity of 99.26%. The molecular ion mass determined by mass spectrometry was 725.49 (theoretical value: 725.30).

[0189] Synthesis Example 9

[0190] Synthesis of compound M203:

[0191]

[0192] Synthesis of intermediate M203-1:

[0193] The synthesis scheme was the same as that of M1-1, and 16.2 g of white solid M203-1 was obtained after column chromatography.

[0194] Synthesis of intermediate M203-2:

[0195] The synthesis scheme was the same as that of M1-2, and 21.8 g of white solid M203-2 was obtained after column chromatography.

[0196] Synthesis of intermediate M203-3:

[0197] The synthesis scheme was the same as that of M1-3, and 5.1 g of yellow solid M203-3 was obtained after column chromatography.

[0198] Synthesis of product M203:

[0199] The intermediate M203-3 (5 g, 6.45 mmol), SM4 (1.66 g, 7.09 mmol), tetrakistriphenylphosphine palladium (74 mg, 0.064 mmol), potassium carbonate (1.34 g, 9.67 mmol), dioxane (50 mL), and water (10 mL) were added to a 250 ml single-necked bottle, replaced with nitrogen three times, and heated to reflux for 12 h.

[0200] The reaction solution was cooled to room temperature, concentrated under reduced pressure to remove the solvent, water was added, DCM was extracted, and the organic phase was concentrated to dryness and column chromatography was performed to obtain 4.1 g of orange-yellow solid with a purity of 99.37%. The molecular ion mass determined by mass spectrometry was 884.56 (theoretical value: 884.41).

[0201] Synthesis Example 10

[0202] Synthesis of compound M229:

[0203]

[0204] Synthesis of intermediate M229-1:

[0205] The synthesis scheme was the same as that of M1-1, and M229-1 was obtained as 16.8 g of white solid after column chromatography.

[0206] Synthesis of intermediate M229-2:

[0207] The synthesis scheme was the same as that of M1-2, and M229-220.9 g of white solid was obtained after column chromatography.

[0208] Synthesis of intermediate M229-3:

[0209] The synthesis scheme was the same as that of M1-3, and M229-34.9 g of yellow solid was obtained after column chromatography.

[0210] Synthesis of product M229:

[0211] The intermediate M229-3 (4.5 g, 5.79 mmol), cuprous cyanide (2.59 g, 28.94 mmol) and DMF (45 mL) were placed in a 100 mL single-necked bottle, replaced with nitrogen three times, and heated to 150° C. for reaction for 20 h.

[0212] The reaction solution was cooled to room temperature, poured into ammonia water for crystallization, filtered, and filtered through a filter cake column to obtain 3.5 g of an orange-yellow solid with a purity of 99.47%. The molecular ion mass determined by mass spectrometry was 723.38 (theoretical value: 723.26).

[0213] Device Embodiment

[0214] Implementation

[0215] OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0216] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0217] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0218] 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.

[0219] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0220] 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.

[0221]

[0222]

[0223]

[0224]

[0225] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0226]

[0227] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host) and a sensitizer material. The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0228] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0229] In one aspect of the present invention, the light-emitting layer host may be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0230]

[0231]

[0232]

[0233]

[0234] In one aspect of the present invention, the light-emitting layer sensitizer can be selected from TADF materials or phosphorescent materials, wherein the TADF material can be selected from, but not limited to, one or more combinations of TDE1-TDE37 listed below.

[0235]

[0236]

[0237]

[0238] In one aspect of the present invention, the sensitizer of the light-emitting layer can be selected from TADF materials and phosphorescent materials, wherein the phosphorescent material can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0239]

[0240]

[0241] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0242] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0243] 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.

[0244]

[0245]

[0246]

[0247]

[0248] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0249] The device may further include an electron injection layer located between the electron transport layer and the cathode. Materials for the electron injection layer include, but are not limited to, one or more combinations of the following.

[0250] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Yb, Mg.

[0251] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0252] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment to completely remove the water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0253] Place the glass substrate with the anode in a vacuum chamber and evacuate to 10 -5 Pa, on the above anode layer film, vacuum thermally evaporate 10 nm of HT-4:HI-3 (97 / 3, w / w) mixture as a hole injection layer, 60 nm of compound HT-4 as a hole transport layer, and 5 nm of compound HT-40 as an electron blocking layer in sequence;

[0254] The light-emitting layer includes a main body material, a sensitizer and a fluorescent dye. The doping ratio is adjusted by adjusting the evaporation rate of each material by using a multi-source co-evaporation method, and the total evaporation film thickness is 40nm; wherein, when the thermally activated sensitized luminescence technology is adopted, the doping ratio of the main body, the TADF sensitizer and the fluorescent dopant is 69:30:1 (w / w / w), the main body is selected as PH-62, the TADF sensitizer is selected as TDE13, and the fluorescent dopant is selected from the compound of the present invention;

[0255] 5nm of ET-23 is used as a hole blocking layer, 25nm of a mixture of compounds ET-69:ET-57 (50 / 50, w / w) is used as an electron transport layer, 1nm of LiF is used as an electron injection layer, and 150nm of metal aluminum is used as a cathode. The total evaporation rate of all organic layers and LiF is controlled at 0.1nm / sec, and the evaporation rate of the metal electrode is controlled at 1nm / sec.

[0256] Device Example 2 to Device Example 26 in Table 1 are manufactured using the same method as Device Example 1, except that the dyes in the light-emitting layers are replaced respectively.

[0257] Device Comparative Examples 1 to 4 were prepared in the same manner as in Device Example 1, except that M-1 in the light-emitting layer was replaced by compounds Ref-1 (CN112979687A), Ref-2 (CN116367574A) and Ref-3 (JP20232881A) in the prior art.

[0258]

[0259] Device testing method:

[0260] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0261] At the same brightness, the driving voltage of the organic electroluminescent devices prepared in the embodiment and the comparative example was measured using a digital source meter and PR650. Specifically, the voltage was increased at a rate of 0.1 V per second, and the driving voltage was measured when the brightness of the organic electroluminescent device reached 5000 cd / m 2 The voltage at the time is the driving voltage at the corresponding brightness. At the same time, the external quantum efficiency (EQE%) of the device can be directly tested on PR650.

[0262] The performance of organic electroluminescent devices is shown in the following table:

[0263]

[0264]

[0265] The above results show that the novel organic material of the present invention is used for organic electroluminescent devices. Compared with comparative example devices 1-3, embodiment devices 1-10 can effectively reduce the operating voltage and improve the external quantum efficiency, and are green light materials with good performance.

[0266] 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. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound having a structure as shown in formula (I): in, Ring A is a structure represented by formula (a); R 21 With R 22 Connected or not connected; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 21 , R 22 Each is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C4-C30 alkylsilyl, substituted or unsubstituted C2-C30 alkylamino, substituted or unsubstituted C4-C30 cycloalkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aromatic boron, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R1~R 13 , R 21 , R 22 Two adjacent ones are connected or not connected; R1~R 13 At least one of them has a structure as described in formula (b); In formula (a), the dotted line represents the position of the fused connection; M is selected from NR 18 , O, S or CR 19 R 20 ; R 18 , R 19 , R 20 Each is independently selected from one of C1-C36 linear alkyl, C3-C36 cycloalkyl, C2-C20 alkenyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl; and R 19 With R 20 Connected or not connected; R 14 , R 15 , R 16 , R 17 Each is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C4-C30 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C30 alkylamino, substituted or unsubstituted C4-C30 cycloalkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aromatic boron, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; In formula (b), *—represents the connection site; R 35 With R 36 No connection between them, or R 35 With R 36 Through single bond, O, S, CR 31 R 32 or SiR 33 R 34 connect; R 31 , R 32 , R 33 , R 34 Each is independently selected from one of C1-C10 linear alkyl, C3-C10 cycloalkyl, C2-C20 alkenyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl; and R 31 With R 32 Connect or not connect between them, and R 33 With R 34 Connected or not connected; R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 35 , R 36 Each is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C4-C30 alkylsilyl, substituted or unsubstituted C2-C30 alkylamino, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C4-C30 cycloalkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aromatic boron, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; When the above R1-R 17 , R 21 -R 30 , R 35 , R 36 When substituents are independently present on the above, the substituents are independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C60 aromatic boron, and C3-C30 heteroaryl.

2. The organic compound according to claim 1, characterized in that It has a structure shown in the following formula (II-a) or (II-b): Where R1~R 17 , the range of M is the same as that in formula (Ⅰ); R 21 With R 22 The two devices are connected or not connected by a single key.

3. The organic compound according to claim 2, characterized in that It has a structure shown in the following formula (II-c) or (II-d): Where R1~R 17 The defined ranges of M are the same as those in formula (I).

4. The organic compound according to claim 2, characterized in that in, R1~R 17 , R 21 , R 22 Each is independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C4-C10 cycloalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the R1 to R 17 , R 21 , R 22 Each is independently selected from one of hydrogen, deuterium, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl and imidazolyl.

5. The organic compound according to any one of claims 1 to 3, characterized in that in, R1, R2, R5, R6, R 11 , R 12 , R 13 At least one of them has a structure as described in formula (b); Preferably, R1, R6, R 12 At least one of the following is selected from the group consisting of the structures described in (b).

6. The organic compound according to any one of claims 1 to 3, characterized in that in, Formula (b) has a structure as shown in formula (b-1), wherein R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 The definition range is the same as that in formula (b): In formula (b-1), L represents a single bond, and p is 0 or 1; when p is 0, L does not exist; Or L for O, S, CR 31 R 32 or SiR 33 R 34 , p is 1, the R 31 , R 32 , R 33 , R 34 Each independently selected from one of a C1-C10 chain alkyl group, a C6-C60 aryl group, and a C5-C60 heteroaryl group; preferably, formula (b) has a structure as shown in formula (b-2), wherein R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 The definition range is the same as that in formula (b):

7. The organic compound according to claim 6, characterized in that in, R6 has a structure as described in formula (b-1); and / or, R 12 It has the structure described by formula (b-1).

8. The organic compound according to any one of claims 1 to 3, characterized in that In formula (b), R 23 -R 30 , R 35 , R 36 Each is independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C4-C10 cycloalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the R 23 -R 30 , R 35 , R 36 Each is independently selected from one of hydrogen, deuterium, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, and imidazolyl; More preferably, R 35 , R 36 All connected via a single button.

9. The organic compound according to claim 1, characterized in that It has the following structure:

10. Use of the organic compound according to any one of claims 1 to 9, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a light-emitting dye in the light-emitting layer.

11. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the organic compound according to any one of claims 1 to 9; Preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the organic compound described in any one of claims 1 to 9; More preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer includes a host material and a dye, and the dye includes at least one organic compound described in any one of claims 1 to 9.

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

Images