Organic compound, electronic component and electronic device containing the same

Abstract

The present application relates to an organic compound and an electronic component and an electronic device containing the organic compound. The structural formula of the organic compound of the present application is shown in Formula 1. The organic compound is applied to an organic electroluminescent device to significantly improve the performance of the device.

Description

Technical Field

[0001] The present application belongs to the technical field of organic materials, and in particular, relates to an organic compound and an electronic component and an electronic device containing the organic compound. Background Art

[0002] Organic electroluminescent device technology is regarded as the next generation of display and lighting technology due to its advantages of active light emission, high luminous efficiency, low power consumption, light weight, thinness, fast response speed, and wide viewing angle. Organic electroluminescent devices are composed of substrates, anodes, hole injection layers, hole transport layers and electron blocking layers, organic light-emitting layers, electron transport layers and hole blocking layers, electron injection layers, and cathodes. For the combination of OLED devices with different structures, the optoelectronic functional materials used have strong selectivity, and the performance of the same material in devices with different structures may also be completely different.

[0003] In order to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously research and innovate OLED optoelectronic functional materials to create functional materials for higher performance OLEDs. Usually, the hole transport layer (HTL) is the thickest in OLED devices, so the performance of the hole transport material used plays a vital role in the performance of the device. At present, most commonly used HTL materials contain carbazole or fluorene compounds. Since these materials are mostly regular planar molecules, their devices generally have low voltage, but there is still room for improvement in efficiency and life. In addition, the P-type in the luminescent layer materials of commonly used green light devices is mostly bicarbazole compounds. Since most of them do not contain alkyl substituents, they will lead to poor molecular film-forming properties and high glass transition. Therefore, compared with the actual product application requirements, the luminous efficiency, service life and other performance of OLED devices need to be further improved. Summary of the invention

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound and an electronic component and an electronic device containing the organic compound, wherein the organic compound can improve the performance of the electronic component and the electronic device.

[0005] The first aspect of the present application provides an organic compound having a structure as shown in Formula 1:

[0006]

[0007] Wherein, m is 1 or 2;

[0008] R a and R b are the same or different and are each independently selected from methyl or hydrogen;

[0009] X is selected from O, S, N (Rc ) or C(R d R e );

[0010] R c , R d , R e are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms;

[0011] M is selected from one of Formula I, Formula II, and Formula III:

[0012]

[0013] in, Represents a chemical bond;

[0014] Ring A, Ring B, Ring C and Ring D are the same or different, and are each independently selected from a benzene ring or a condensed aromatic ring having 10 to 14 ring carbon atoms;

[0015] Rr is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0016] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0017] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 R i Indicates that n 1 、n 2 、n 3 、n 4 、n 5 、n 6 and n 7 n i Indicates that n i Represents R i The number of, i is a variable, representing 1, 2, 3, 4, 5, 6 and 7. When i is 1, 3, n iSelected from 0, 1, 2, 3; when i is 2, n i is selected from 0, 1, 2, 3, 4; when i is 4, 5, 7, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; when i is 6, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7; and when n i When it is greater than 1, any two R i Same or different;

[0018] Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0019] L, L 1 , L 2 , L 3 , L 4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0020] Rr, L, L 1 , L 2 , L 3 , L 4 ,Ar 1 and Ar 2 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0021] Optionally, Ar 1 Any two adjacent substituents in form a saturated or unsaturated 3-15 membered ring;

[0022] Optionally, Ar 2 Any two adjacent substituents in the group form a saturated or unsaturated 3-15 membered ring.

[0023] A second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0024] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect.

[0025] The organic compound of the present application is a tetramethyltetralin (or tetramethylindan) as a substituent, and is connected to an aza-anthracene group, which can effectively increase the stability of the structure, so that the compound has a larger rigid structure, which is beneficial to improve the glass transition temperature and thermal stability of the material, and is beneficial to the film formation of the product, and prolongs the service life of the material. The compound of the present application is connected to tetramethyltetralin on the aza-anthracene group, and is connected to a triarylamine or carbazole group at the same time, which not only makes the product have a larger steric effect, but also can adjust the angle and conjugation degree between each branch chain, so that the HOMO value of the compound can be more matched with the adjacent film layer, thereby reducing the driving voltage, improving the electron density of the conjugated system of the entire compound, and is beneficial to improving the carrier conduction efficiency of the organic electroluminescent device, so that the efficiency and life of the organic electroluminescent device can be effectively improved.

[0026] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0028] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to one embodiment of the present application.

[0029] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0030] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0031] Figure 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0032] Reference numerals

[0033] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device DETAILED DESCRIPTION

[0034] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0035] In a first aspect, the present application provides an organic compound having a structure as shown in Formula 1:

[0036]

[0037] Wherein, m is 1 or 2;

[0038] R a and R b are the same or different and are each independently selected from methyl or hydrogen;

[0039] X is selected from O, S, N (R c ) or C(R d R e );

[0040] R c , R d , R e are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms;

[0041] M is selected from one of Formula I, Formula II, and Formula III:

[0042]

[0043] in, Represents a chemical bond;

[0044] Ring A, Ring B, Ring C and Ring D are the same or different, and are each independently selected from a benzene ring or a condensed aromatic ring having 10 to 14 ring carbon atoms;

[0045] Rr is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0046] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0047] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 R i Indicates that n 1 、n 2 、n 3 、n 4 、n 5 、n 6 and n 7 n i Indicates that n i Represents R i The number of, i is a variable, representing 1, 2, 3, 4, 5, 6 and 7. When i is 1, 3, n i Selected from 0, 1, 2, 3; when i is 2, n i is selected from 0, 1, 2, 3, 4; when i is 4, 5, 7, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; when i is 6, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7; and when n i When it is greater than 1, any two R i Same or different;

[0048] Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0049] L, L 1 , L 2 , L 3 , L 4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0050] Rr, L, L 1 , L 2 , L 3 , L 4 ,Ar 1 and Ar 2The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0051] Optionally, Ar 1 Any two adjacent substituents in form a saturated or unsaturated 3-15 membered ring;

[0052] Optionally, Ar 2 Any two adjacent substituents in the group form a saturated or unsaturated 3-15 membered ring.

[0053] Optionally, in Formula 1, Selected from the group consisting of:

[0054]

[0055] In the present application, the terms "optionally" and "optionally" mean that the event or environment described later may but need not occur, and the description includes scenarios where the event occurs or does not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents can form a ring but do not have to form a ring, including: scenarios where two adjacent substituents form a ring and scenarios where two adjacent substituents do not form a ring. For another example, "optionally, Ar 2 Any two adjacent substituents in the form a saturated or unsaturated 3-15 membered ring" refers to Ar 2 Any two adjacent substituents in the group may be linked to form a 3- to 15-membered ring, or Ar 2 Any two adjacent substituents in the group may also exist independently.

[0056] "Any two adjacent" may include two substituents on the same atom, or one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are connected; when there is one substituent on each of two adjacent atoms, the two substituents may be fused into a ring.

[0057] In the present application, the fluorenyl group may be substituted by 1 or 2 or more substituents. In the case where the fluorenyl group is substituted, it may be: etc., but not limited thereto.

[0058] In this application, the descriptions "each... is independently" and "... are independently" and "... are independently selected from" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, " Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0059] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, etc.

[0060] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0061] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Among them, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0062] In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, halogenated alkyl groups, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.

[0063] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. Among them, thienyl, furanyl, phenanthroline, etc. are heteroaryl groups of single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of polycyclic system type connected by carbon-carbon bond conjugation. In this application, the heteroaryl group involved refers to a divalent group formed by further losing a hydrogen atom of the heteroaryl group.

[0064] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0065] In this application, Rr, L, L 1 , L 2 , L 3 , L 4 ,Ar 1 and Ar 2The number of carbon atoms of the aryl group of the substituent can be 6 to 20, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, and phenanthrenyl.

[0066] In this application, Rr, L, L 1 , L 2 , L 3 , L 4 ,Ar 1 and Ar 2 The number of carbon atoms of the heteroaryl group of the substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the heteroaryl group as a substituent include, but are not limited to, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0067] In this application, the non-localized connecting bond refers to the single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.

[0068] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0069] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0070] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0071] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0072] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentane and cyclohexane.

[0073] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that penetrate the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

[0074]

[0075] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0076]

[0077] In some embodiments of the present application, the organic compound is selected from the compound shown in Formula 1-1:

[0078]

[0079] In some embodiments of the present application, the organic compound is selected from the compounds shown in Formula 1-2 and Formula 1-3:

[0080]

[0081] In some embodiments of the present application, ring A, ring B, ring C and ring D are the same or different, and are independently selected from a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring. Optionally, ring A, ring B, ring C and ring D are all benzene rings; or ring A is a naphthalene ring, and ring B, ring C and ring D are all benzene rings; or ring A and ring C are all naphthalene rings, and ring B and ring D are all benzene rings.

[0082] In some embodiments of the present application, Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms. 1 and Ar 2 The same or different, each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0083] Optionally, Ar 1 and Ar 2The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms;

[0084] Optionally, Ar 1 Any two adjacent substituents in form a saturated or unsaturated 5-13 membered ring;

[0085] Optionally, Ar 2 Any two adjacent substituents in the group form a saturated or unsaturated 5- to 13-membered ring.

[0086] In other embodiments of the present application, Ar 1 and Ar 2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.

[0087] Optionally, Ar 1 and Ar 2 The substituents in are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl;

[0088] Optionally, Ar 1 Any two adjacent substituents in the form a fluorene ring

[0089] Optionally, Ar 2 Any two adjacent substituents in the form a fluorene ring

[0090] Further optionally, when Ar 1 and Ar 2 When at least one of the organic compounds is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, the molecular spatial configuration of the organic compound of the present application is more stereoscopic, thereby increasing T 1 level, effectively blocking the diffusion of excitons, increasing the molecular rigidity and thermal stability as a whole, and significantly improving the service life of the device when used as a hole transport layer in an organic electroluminescent device.

[0091] Optionally, Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:

[0092]

[0093] Wherein, the substituted group W has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0094] Optionally, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

[0095]

[0096] Further optionally, Ar 1 and Ar 2 Each is independently selected from the following groups:

[0097]

[0098] In some embodiments of the present application, L 1 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms. 1 A single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11 or 12 carbon atoms.

[0099] Optionally, L 1 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0100] In some other embodiments of the present application, L 1 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

[0101] Optionally, L 1 The substituents in are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl or phenyl.

[0102] Optionally, L 1 Selected from the group consisting of a single bond or the following groups:

[0103]

[0104] Further optionally, L 1 Selected from the group consisting of a single bond or the following groups:

[0105]

[0106] In some embodiments of the present application, L, L 2 , L 3and L 4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms. 2 , L 3 and L 4 the same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11 or 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.

[0107] Optionally, L, L 2 , L 3 and L 4 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0108] In some other embodiments of the present application, L, L 2 , L 3 and L 4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group.

[0109] Optionally, L, L 2 , L 3 and L 4 The substituents in are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0110] Further optionally, L, L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted dibenzofuranylene group.

[0111] Further optionally, L 3 and L 4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group.

[0112] Preferably, L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group.

[0113] Preferably, L 2is selected from a single bond or phenylene.

[0114] In some embodiments of the present application, L, L 2 , L 3 and L 4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted group Q; wherein the unsubstituted group Q is selected from the group consisting of the following groups:

[0115]

[0116] The substituted group Q has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0117] Optionally, L, L 2 , L 3 and L 4 The same or different, and each independently selected from the group consisting of a single bond or the following groups:

[0118]

[0119]

[0120] Further optionally, L, L 2 , L 3 and L 4 Each is independently selected from the group consisting of a single bond or the following groups:

[0121]

[0122] In some embodiments of the present application, The same or different, and each independently selected from the group consisting of the following groups:

[0123]

[0124] Optionally, The same or different, and each independently selected from the group consisting of the following groups:

[0125]

[0126]

[0127] In some embodiments of the present application, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R7 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0128] In some embodiments of the present application, n 1 、n 2 、n 3 、n 4 、n 5 、n 6 and n 7 are the same or different and are independently selected from 0 or 1.

[0129] In some embodiments of the present application, Rr is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms. For example, Rr is selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0130] Optionally, the substituents in Rr are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0131] In other embodiments of the present application, Rr is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0132] Optionally, the substituents in Rr are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0133] Optionally, Rr is selected from a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the following groups:

[0134]

[0135] Wherein, the substituted group V has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0136] Optionally, Rr is selected from the group consisting of:

[0137]

[0138] Further optionally, Rr is selected from the group consisting of:

[0139]

[0140] In some embodiments of the present application, Selected from the group consisting of:

[0141]

[0142] In some embodiments of the present application, Selected from the group consisting of:

[0143]

[0144] In a specific embodiment of the present application, R c is phenyl, R d and R e All are methyl. Optionally, the organic compound is selected from the following compounds:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] In a second aspect, the present application provides an electronic component, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0156] Optionally, the functional layer includes a hole transport layer, and the hole transport layer includes the organic compound described in the present application.

[0157] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound described in the present application.

[0158] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0159] Further optionally, the electronic element is an organic electroluminescent device, the hole transport layer includes a first hole transport layer and a second hole transport layer (electron blocking layer), the first hole transport layer is closer to the anode than the second hole transport layer, and the first hole transport layer contains the organic compound.

[0160] In some embodiments, the electronic component is an organic electroluminescent device. Figure 1 As shown, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340 and a cathode 200 which are sequentially stacked.

[0161] In a specific embodiment, the organic electroluminescent device is a blue organic electroluminescent device.

[0162] In a specific embodiment, the organic electroluminescent device is a green organic electroluminescent device.

[0163] In a specific embodiment, the organic electroluminescent device is a red organic electroluminescent device.

[0164] Optionally, the anode 100 includes the following anode materials, which are optionally materials with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0165] Optionally, the first hole transport layer 321 includes one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and those skilled in the art can select them according to the prior art.

[0166] For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0167]

[0168]

[0169]

[0170] In one specific embodiment, the first hole transport layer 321 is an organic compound of the present application. In another specific embodiment, the first hole transport layer 321 is compound HT-01.

[0171] In one embodiment, the second hole transport layer 322 (electron blocking layer) is TCTA (HT-16). In another embodiment, the second hole transport layer 322 is compound HT-02. In yet another embodiment, the second hole transport layer 322 is compound HT-03.

[0172] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a main material and a doping material. Optionally, the organic light-emitting layer 330 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.

[0173] The main material of the organic light-emitting layer 330 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special restrictions thereon. The main material may be a single main material or a mixed main material.

[0174] In some embodiments of the present application, the main material of the organic light-emitting layer 330 is BH-01. In other embodiments of the present application, the main material of the organic light-emitting layer 330 is the organic compound of the present application.

[0175] The doping material of the organic light emitting layer 330 can be selected with reference to the prior art, for example, it can be selected from iridium (III) organic metal complex, platinum (II) organic metal complex, ruthenium (II) complex, etc. Specific examples of the doped material include, but are not limited to,

[0176]

[0177]

[0178] In some embodiments of the present application, the doping material of the organic light-emitting layer 330 is BD-1. In other embodiments of the present application, the doping material of the organic light-emitting layer 330 is Ir(ppy). 3In some other embodiments of the present application, the doping material of the organic light emitting layer 330 is Ir(Mphq) 3 .

[0179] Optionally, the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport material may generally include a metal complex or / and a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from, for example, LiQ, Alq 3 , Bepq 2 etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc., and specific examples include but are not limited to ET-1, Bphen, NBphen, DBimiBphen, BimiBphen and other 1,10-phenanthroline compounds, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below. In some embodiments of the present application, the electron transport layer 340 is composed of TPBi (ET-16) and LiQ.

[0180]

[0181] In the present application, cathode 200 may include cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.

[0182] Alternatively, if Figure 1 As shown, a hole injection layer 310 may be provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular restrictions on this. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0183]

[0184] In a specific embodiment of the present application, the hole injection layer 310 is HAT-CN.

[0185] Alternatively, if Figure 1As shown, an electron injection layer 350 is also provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In a specific embodiment of the present application, the electron injection layer 350 includes Yb.

[0186] According to other embodiments, the electronic component is a photoelectric conversion device. Figure 3 As shown, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.

[0187] According to a specific implementation mode, Figure 3 As shown, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200 which are stacked in sequence.

[0188] Optionally, the photoelectric conversion device is a solar cell, especially an organic thin film solar cell. In some embodiments of the present application, the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer and a cathode stacked in sequence, wherein the hole transport layer 320 comprises the organic compound of the present application.

[0189] A third aspect of the present application provides an electronic device, comprising the electronic component provided by the second aspect of the present application.

[0190] According to some embodiments, Figure 2 As shown, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0191] According to other embodiments, Figure 4 As shown, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera or other types of electronic devices.

[0192] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0193] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0194] Synthesis example

[0195] 1. Synthesis of IMA-1-1

[0196]

[0197] Under nitrogen protection, sub 1 (64 g, 239.53 mmol), N-fluorobisbenzenesulfonamide (151.07 g, 479.06 mmol), acetonitrile (512 mL), 2-chloro-1,10-phenanthroline (2.06 g, 9.58 mmol) and tetrakis(acetonitrile)tetrafluoroborate palladium (II) (2.13 g, 4.79 mmol) were added to a three-necked flask, and the temperature was raised to 50°C, and the reaction was stirred for 24 hours to terminate the reaction. When the reaction liquid reached room temperature, it was washed with water and extracted with dichloroethane. After the organic phase was collected, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography (eluted with petroleum ether) to obtain solid IM A-1-1 (30.81 g, yield 45.10%).

[0198] 2. Synthesis of IMA-2-1

[0199]

[0200] Under nitrogen protection, sub 1 (39.64 g, 148.35 mmol), TBAB (239.1 g, 741.75 mmol), NaN 3 (12.54 g, 192.86 mmol), dichloroethane (400 mL), stirred at room temperature for 24 h, then added 2,3-dichloro-5,6-dicyanobenzoquinone (50.51 g, 222.53 mmol), heated to reflux and stirred for 0.5 h before the reaction was terminated. The reaction solution was cooled to room temperature, washed with water, extracted with dichloroethane, the organic phase was collected and the solvent was removed under reduced pressure, and the crude product was recrystallized and purified using ethyl acetate and n-heptane to obtain solid IM A-2-1 (30.87 g, yield 71.21%).

[0201] 3. Synthesis of IMA-3-1

[0202]

[0203] Under nitrogen protection, sub 2 (57.77 g, 169.80 mmol), phenylboric acid (20.70 g, 169.80 mmol), TBAB (1.09 g, 3.4 mmol), potassium carbonate (35.15 g, 254.7 mmol), tetrakis(triphenylphosphine)palladium (1.96 g, 1.70 mmol), THF (465 mL) and water (116 mL) were added to a three-necked flask, and the mixture was stirred and heated to reflux. The reaction was terminated after 24 hours of reaction. The organic layer was washed with water until neutral, and extracted with DCM. After the organic phase was collected, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography (eluted with petroleum ether) and washed with ethanol to obtain IM A-3-1 (31 g, yield 53.18%).

[0204] 4. Synthesis of IMA-4-1

[0205]

[0206] Under nitrogen protection, sub 1 (30.30 g, 113.38 mmol), p-chlorophenylboronic acid (21.28 g, 136.06 mmol), TBAB (0.73 g, 2.27 mmol), potassium carbonate (23.47 g, 170.07 mmol), tetrakis(triphenylphosphine)palladium (1.31 g, 1.13 mmol), THF (183 mL) and water (61 mL) were added to a three-necked flask, stirred and heated to reflux, and the reaction was terminated after 20 hours of reaction. The organic layer was washed with water 3 times and extracted with dichloromethane. The organic phase was collected and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (eluted with n-heptane) and washed with ethanol to obtain IM A-4-1 (23.0 g, yield 67.88%).

[0207] IMA-4-X shown in Table 1 was synthesized by referring to the method of IMA-4-1, except that IMA-1 was used instead of sub 1, and raw material 1 was used instead of p-chlorophenylboronic acid, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0208] Table 1

[0209]

[0210] 5. Synthesis of intermediate IM A-5-1:

[0211]

[0212] Under nitrogen protection, 3-bromo-10H-phenoxazine (22.61 g, 86.25 mmol), sub 1 (23.51 g, 87.98 mmol) and toluene (185 mL) were added to a three-necked flask, and the mixture was stirred and heated to reflux. Then tri(dibenzylideneacetone)dipalladium (0.79 g, 0.8625 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.82 g, 1.725 mmol) and sodium tert-butoxide (17.85 g, 129.38 mmol) were added, and the mixture was stirred and heated to 110°C for 2 h. Then it was cooled to room temperature, the reaction solution was washed with water until neutral, the organic phase was collected, anhydrous magnesium sulfate was added to the organic phase for drying, and the filtrate was concentrated after filtration; the obtained crude product was purified by silica gel column chromatography, and then the crude product was recrystallized and purified using a dichloromethane / n-heptane system to obtain IM A-5-1 (26.46 g, yield 67.12%).

[0213] The intermediate IM A-5-X shown in Table 2 was synthesized by referring to the method of intermediate IM A-5-1, except that raw material 2 was used instead of 3-bromo-10H-phenoxazine, and raw material 3 was used instead of sub 1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0214] Table 2

[0215]

[0216]

[0217]

[0218] 6. Synthesis of IMA-5-15

[0219]

[0220] Under nitrogen protection, IM A-5-13 (29.79 g, 66.58 mmol), bromobenzene (10.66 g, 67.91 mmol), and toluene (74 mL) were added to a three-necked flask, and the mixture was stirred and heated to reflux. Then, tri(dibenzylideneacetone)dipalladium (0.26 g, 0.2842 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.27 g, 0.5684 mmol) and sodium tert-butoxide (4.10 g, 42.63 mmol) were added, and the mixture was stirred and heated to 110°C for 2 hours. The mixture was then cooled to room temperature, the reaction solution was washed with water, dried with magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent. The crude product was purified by silica gel column chromatography, and then the crude product was recrystallized and purified using a dichloromethane / n-heptane system to obtain IM A-5-15 (24.87 g, yield 71.35%).

[0221] 7. Synthesis of IMA-6-1:

[0222]

[0223] Nitrogen (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 min, and IM A-5-1 (25.85 g, 57.65 mmol), biboric acid pinacol ester (21.96 g, 86.48 mmol), potassium acetate (8.49 g, 86.48 mmol), x-Phos (0.55 g, 1.15 mmol), tris (dibenzylideneacetone) palladium (0.53 g, 0.58 mmol) and dioxane (207 mL) were added in sequence, and the mixture was heated to reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature. The reaction solution was extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, the filtrate was concentrated after filtration, and the crude product was recrystallized and purified using a dichloroethane / n-heptane system to obtain IM A-6-1 (20.53 g, yield 71.88%).

[0224] IMA-6-X shown in Table 3 was synthesized by referring to the method of IMA-6-1, except that IMA-5-X was used instead of IMA-5-1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0225] Table 3

[0226]

[0227]

[0228]

[0229] 8. Synthesis of IMA-7-1

[0230]

[0231] Under nitrogen protection, add IM A-6-1 (17.9 g, 36.13 mmol), m-chlorobromobenzene (5.32 g, 27.79 mmol), toluene (108 mL), ethanol (36 mL), water (18 mL) and potassium carbonate (5.75 g, 41.69 mmol) to the reaction bottle; start stirring, heat to 50°C to 60°C, quickly add tetrakis(triphenylphosphine)palladium (0.32 g, 0.2779 mmol) and tetrabutylammonium bromide (TBAB) (0.18 g, 0.5558 mmol), then continue to heat to 70°C to 75°C, reflux for 20 hours. After the reaction is complete, cool to room temperature, extract with dichloromethane, wash the organic phase with water until neutral, dry, filter and concentrate. Recrystallize with dichloromethane / petroleum ether to obtain solid IM A-7-1 (8.51 g, yield 63.79%).

[0232] The intermediate IMA-7-X shown in Table 4 was synthesized by referring to the method of IMA-7-1, except that IMA-6-X was used instead of IMA-6-1, and raw material 4 was used instead of m-chlorobromobenzene, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 4.

[0233] Table 4

[0234]

[0235]

[0236] 9. Synthesis of Compound 16

[0237]

[0238] Under nitrogen protection, IM A-5-1 (7.54 g, 16.81 mmol), 4-aminobiphenyl (2.84 g, 16.81 mmol) and toluene (80 mL) were added to a three-necked flask, the temperature was raised to reflux, tri(dibenzylideneacetone)dipalladium (0.15 g, 0.1681 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.16 g, 0.3362 mmol), sodium tert-butoxide (3.48 g, 25.22 mmol) were added, heated to 108 ° C, stirred for 1 h; then cooled to room temperature, the reaction solution was washed with water until neutral, the organic phase was collected, anhydrous magnesium sulfate was added to the organic phase for drying, the filtrate was concentrated after filtration; the crude product was recrystallized and purified using a dichloromethane / n-heptane system to obtain a gray solid IM A-8-1 (6.5 g, yield 72.03%).

[0239]

[0240] Under nitrogen protection, IM A-8-1 (6.04 g, 11.26 mmol), 4-bromobiphenyl (2.68 g, 11.49 mmol) and toluene (60 mL) were heated to reflux, tri(dibenzylideneacetone)dipalladium (0.10 g, 0.1126 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.092 g, 0.2252 mmol) and sodium tert-butoxide (1.62 g, 16.89 mmol) were added, heated to 108 ° C, and stirred for 2 h; then cooled to room temperature, the reaction solution was washed with water to obtain an organic phase, the organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated; the crude product was recrystallized and purified using a dichloromethane / n-heptane system to obtain a white solid compound 16 (5.47 g, yield 70.48%), mass spectrum (m / z) = 689.4 [M+H] + .

[0241] Compound X shown in Table 5 was synthesized by referring to the method of compound 16, except that raw material 5 was used instead of IMA-5-1, raw material 6 was used instead of 4-aminobiphenyl, and raw material 7 was used instead of 4-bromobiphenyl, wherein the main raw materials used, the synthesized compounds and their final step yields and mass spectra are shown in Table 5.

[0242] Table 5

[0243]

[0244]

[0245]

[0246]

[0247] 10. Synthesis of Compound A18

[0248]

[0249] Under nitrogen protection, add IM A-6-1 (11.24 g, 22.68 mmol), 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (6.02 g, 15.12 mmol), toluene (72 mL), ethanol (24 mL), water (12 mL) and potassium carbonate (3.13 g, 22.68 mmol) to the reaction bottle; start stirring, heat to 50°C to 60°C, quickly add tetrakis(triphenylphosphine)palladium (0.17 g, 0.1512 mmol) and tetrabutylammonium bromide (TBAB) (0.097 g, 0.30 mmol), then continue to heat to 70°C to 75°C, reflux for 20 hours. After the reaction is complete, cool to room temperature, extract with dichloromethane, wash the organic phase with water until neutral, dry, filter and concentrate. The obtained crude product was recrystallized from toluene / petroleum ether to obtain solid compound A18 (5.39 g, yield 51.91%), mass spectrum (m / z) = 687.3 [M+H] + .

[0250] Compound AX was synthesized by referring to the method of compound A18, except that IM A-6-X was used instead of IM A-6-1, and raw material 8 was used instead of 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole, wherein the main raw materials used, the synthesized compounds, their yields and mass spectra are shown in Table 6.

[0251] Table 6

[0252]

[0253]

[0254]

[0255] 11. Synthesis of IMA-9-1

[0256]

[0257] Under nitrogen protection, 2-bromo-5H-benzocarbazole (13.02 g, 43.95 mmol), 2-bromonaphthalene (9.1 g, 43.95 mmol), and toluene (105 mL) were added to a three-necked flask, and the mixture was stirred and heated to reflux. Then, tri(dibenzylideneacetone)dipalladium (0.4 g, 0.4395 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.42 g, 0.879 mmol) and sodium tert-butoxide (63.4 g, 65.93 mmol) were added, and the mixture was stirred and heated to 110°C for 2 h. The mixture was then cooled to room temperature, and the reaction solution was washed with water to obtain an organic phase. The organic phase was dried by adding anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The crude product was recrystallized and purified using a dichloromethane / n-heptane system to obtain IM A-9-1 (12.03 g, yield 64.81%).

[0258] IMA-9-X was synthesized by referring to the method of IMA-9-1, except that raw material 9 was used instead of 2-bromo-5H-benzocarbazole, and raw material 10 was used instead of 2-bromonaphthalene, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 7.

[0259] Table 7

[0260]

[0261]

[0262] 12. Synthesis of Compound B3

[0263]

[0264] Under nitrogen protection, add IMA-6-1 (11.97 g, 24.15 mmol), IMA-9-4 (6.28 g, 16.1 mmol), toluene (72 mL), ethanol (24 mL), water (12 mL) and potassium carbonate (3.33 g, 24.15 mmol) to the reaction bottle; start stirring, heat to 50-60 ° C, quickly add tetrakis (triphenylphosphine) palladium (0.19 g, 0.161 mmol) and tetrabutylammonium bromide (TBAB) (0.10 g, 0.322 mmol), and then continue to heat to 70-75 ° C, reflux reaction for 16 hours. After the reaction is completed, cool to room temperature, extract with dichloromethane, wash the organic phase with water until neutral, dry, filter and concentrate. Recrystallization with dichloromethane and petroleum ether gave solid compound B3 (5.88 g, yield 53.8%), mass spectrum (m / z) = 679.3 [M+H] + .

[0265] Compound BX was synthesized by referring to the method of compound B3, except that IM A-6-X was used instead of IM A-6-1, and raw material 11 was used instead of IM A-9-4, wherein the main raw materials used, the synthesized compounds and their yields and mass spectra are shown in Table 8.

[0266] Table 8

[0267]

[0268]

[0269] The NMR data of the compound are shown in Table 9:

[0270] Table 9

[0271]

[0272] Preparation and evaluation of organic electroluminescent devices:

[0273] Example 1: Preparation of blue organic electroluminescent device

[0274] The organic electroluminescent device was prepared by the following process: a substrate coated with ITO / Ag / ITO (10nm / 100nm / 10nm) electrodes was cut into a size of 40mm×40mm×0.5mm, and a photolithography process was used to prepare an experimental substrate with cathode, anode and insulating layer patterns. 2 :N 2 Plasma surface treatment was performed to increase the work function of the anode (experimental substrate) and to remove scum.

[0275] The compound HAT-CN was vacuum-deposited on the experimental substrate (anode) to form a layer with a thickness of Then, a compound 16 is vacuum-evaporated on the hole injection layer to form a hole injection layer with a thickness of A first hole transport layer (HTL) is formed.

[0276] The compound TCTA was evaporated on the first hole transport layer (HTL) as an electron blocking layer (EBL) with a thickness of

[0277] BH-01 was evaporated on the electron blocking layer (EBL) as the main body, and BD-1 was doped with a weight ratio of 2% to form a layer with a thickness of of an organic light-emitting layer (blue light-emitting layer, B-EML).

[0278] TPBi and LiQ with a weight ratio of 1:1 were evaporated on the organic light-emitting layer (EML) as an electron transport layer (ETL) with a thickness of

[0279] Evaporation on the electron transport layer (ETL) The metal Yb is used as the electron injection layer (EIL), the weight ratio of silver (Ag) and magnesium (Mg) is 9:1 as the cathode, and the thickness is

[0280] Compound CP-1 was evaporated on the cathode as an organic capping layer (CPL) with a thickness of

[0281] The vapor-deposited device is encapsulated with ultraviolet curing resin in a nitrogen glove box (the water and oxygen content must be strictly controlled).

[0282] Example 2 to Example 21

[0283] In the above device structure, except that the recorded compound was used instead of Compound 16 in the first hole transport layer (HTL), the organic electroluminescent devices were manufactured in the same manner as in Example 1. The prepared devices were recorded as Examples 2 to 21.

[0284] Comparative Example 1 to Comparative Example 3

[0285] In Comparative Examples 1 to 3, except that Compound A, Compound B, and Compound C are used as materials of the first hole transport layer (HTL) instead of Compound 16, the same method as Example 1 is used to manufacture organic electroluminescent devices, which are respectively referred to as Comparative Examples 1 to 3.

[0286] Among them, the structural formulas of HAT-CN, TCTA, LiQ, TPBi, CP-1, BH-01, BD-1, compound A, compound B, and compound C are shown in Table 10.

[0287] Table 10

[0288]

[0289]

[0290] For the organic electroluminescent device prepared as above, at 15 mA / cm 2 The IVL performance and device life of the device were tested under the conditions of , and the results are shown in Table 11 below.

[0291] Table 11

[0292]

[0293] It can be seen from the above table that, compared with the organic electroluminescent devices of comparative examples 1 to 3, the performance of the organic electroluminescent devices of embodiments 1 to 21 is greatly improved, mainly manifested in that the current efficiency of the device is increased by at least 13.1%, and the T95 life is increased by at least 14.3%.

[0294] Example 22: Preparation of green organic electroluminescent device

[0295] The organic electroluminescent device was prepared by the following process: a substrate coated with ITO / Ag / ITO (10nm / 100nm / 10nm) electrodes was cut into a size of 40mm×40mm×0.5mm, and a photolithography process was used to prepare an experimental substrate with cathode, anode and insulating layer patterns. 2 :N 2 Plasma surface treatment was performed to increase the work function of the anode (experimental substrate) and to remove scum.

[0296] The compound HAT-CN was vacuum-deposited on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer (HIL) of 100 mm thick is formed by vacuum evaporating a compound HT-01 on the hole injection layer to form a A first hole transport layer (HTL) is formed.

[0297] Compound HT-02 was evaporated on the first hole transport layer (HTL) as the second hole transport layer with a thickness of

[0298] On the second hole transport layer, compound A18: compound N: Ir(ppy) 3 The co-evaporation is performed at an evaporation rate of 50%:40%:10% to form a film with a thickness of of an organic light-emitting layer (green light-emitting layer, G-EML).

[0299] TPBi and LiQ were evaporated on the organic light-emitting layer (EML) in a ratio of 1:1 (weight ratio) as an electron transport layer (ETL) with a thickness of

[0300] Evaporation on the electron transport layer (ETL) The metal Yb is used as the electron injection layer (EIL), the weight ratio of silver (Ag) and magnesium (Mg) is 9:1 as the cathode, and the thickness is

[0301] Compound CP-1 was evaporated on the cathode as an organic capping layer (CPL) with a thickness of

[0302] The vapor-deposited device is encapsulated with ultraviolet curing resin in a nitrogen glove box (the water and oxygen content must be strictly controlled).

[0303] Example 23 to Example 32

[0304] In the above device structure, except that the compound in Table 12 was used to replace compound A18 of the organic light-emitting layer (G-EML), the organic electroluminescent device was manufactured by the same method as Example 22. The prepared devices were recorded as Examples 23 to 32.

[0305] Comparative Example 4 to Comparative Example 5

[0306] In Comparative Examples 4 to 5, except for using Compound D and Compound E to replace the P-type host material Compound A18 in the organic light-emitting layer (G-EML), the same method as Example 22 was used to manufacture organic electroluminescent devices, which are respectively recorded as Comparative Examples 4 to 5.

[0307] The structural formulas of the compounds used are shown in Table 12.

[0308] Table 12

[0309]

[0310]

[0311] For the organic electroluminescent device prepared as above, at 15 mA / cm 2 The IVL performance and device life of the device were tested under the conditions of , and the results are shown in Table 13.

[0312] Table 13

[0313]

[0314] As can be seen from the above table, compared with the organic electroluminescent devices of comparative examples 4 to 5, the operating voltage of the organic electroluminescent devices of embodiments 22 to 32 is slightly improved, and the efficiency and life of the device performance are greatly improved; among them, the current efficiency is increased by at least 12.2%, and the T95 life is increased by at least 13.2%.

[0315] Example 33: Preparation of red organic electroluminescent device

[0316] The organic electroluminescent device was prepared by the following process: a substrate coated with ITO / Ag / ITO (10nm / 100nm / 10nm) electrodes was cut into a size of 40mm×40mm×0.5mm, and a photolithography process was used to prepare an experimental substrate with cathode, anode and insulating layer patterns. 2 :N 2Plasma surface treatment was performed to increase the work function of the anode (experimental substrate) and to remove scum.

[0317] The compound HAT-CN was vacuum-deposited on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer (HIL) of 100 mm thick is formed by vacuum evaporating a compound HT-01 on the hole injection layer to form a A first hole transport layer (HTL) is formed.

[0318] Compound HT-03 was evaporated on the first hole transport layer (HTL) as the second hole transport layer with a thickness of

[0319] On the second hole transport layer, compound B3: compound RH-n: Ir(Mphq) 3 The co-evaporation was performed at an evaporation rate of 48.5%:48.5%:3% to form a film with a thickness of of an organic light-emitting layer (red light-emitting layer, R-EML).

[0320] TPBi and LiQ were evaporated on the organic light-emitting layer (EML) in a ratio of 1:1 (weight ratio) as an electron transport layer (ETL) with a thickness of

[0321] Evaporation on the electron transport layer (ETL) The metal Yb is used as the electron injection layer (EIL), the weight ratio of silver (Ag) and magnesium (Mg) is 9:1 as the cathode, and the thickness is

[0322] Compound CP-1 was evaporated on the cathode as an organic capping layer (CPL) with a thickness of

[0323] The vapor-deposited device is encapsulated with ultraviolet curing resin in a nitrogen glove box (the water and oxygen content must be strictly controlled).

[0324] Embodiment 34 to Embodiment 39

[0325] In the above device structure, except that the compound in Table 14 was used to replace the compound B3 of the organic light-emitting layer (R-EML), an organic electroluminescent device was manufactured by the same method as Example 33. The prepared devices were recorded as Examples 34 to 39.

[0326] Comparative Example 6 to Comparative Example 7

[0327] In Comparative Examples 6 to 7, except for using Compound H and Compound I to replace the P-type host material Compound B3 in the organic light-emitting layer (R-EML), the same method as Example 33 is used to manufacture organic electroluminescent devices, which are respectively recorded as Comparative Examples 6 to 7.

[0328] The structural formulas of the compounds used are shown in Table 14.

[0329] Table 14

[0330]

[0331] For the organic electroluminescent device prepared as above, at 15 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 at 20mA / cm 2 The results are shown in Table 15.

[0332] Table 15

[0333]

[0334] It can be seen from the above table that compared with the organic electroluminescent devices of Comparative Examples 6 and 7, the performance of the organic electroluminescent devices of Examples 33 to 39 is greatly improved, the current efficiency is at least increased by 15.6% compared with the comparative examples, and the T95 life is at least increased by 21.7% compared with the comparative examples.

[0335] It should also be noted that the various specific technical features described in the above specific implementation methods can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not further describe various possible combinations.

Claims

1. Organic compounds, It is characterized in that The organic compound has a structure as shown in Formula 1: Wherein, m is 1 or 2; R a and R b are the same or different and are each independently selected from methyl or hydrogen; X is selected from O, S, N (R c ) or C(R d R e ); R c Phenyl, R d and R e All are methyl; M is selected from one of Formula II and Formula III: in, Represents a chemical bond; Ring A, Ring B, Ring C and Ring D are the same or different, and are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring; Rr is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl; The substituents in Rr are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 R i Indicates that n 1 、n 2 、n 3 、n 4 、n 5 、n 6 and n 7 n i Indicates that n i Represents R i The number of, i is a variable, representing 1, 2, 3, 4, 5, 6 and 7. When i is 1, 3, n i Selected from 0, 1, 2, 3; when i is 2, n i is selected from 0, 1, 2, 3, 4; when i is 4, 5, 7, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; when i is 6, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7; and when n i When it is greater than 1, any two R i Same or different; L 1 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; L 1 The substituents in are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl or phenyl; L, L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolylene group; L, L 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl.

2. The organic compound according to claim 1, It is characterized in that The organic compound is selected from the group consisting of the following compounds:

3. Electronic components, It is characterized in that The invention comprises an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the characteristic is that the functional layer comprises the organic compound according to any one of claims 1 to 2.

4. The electronic component according to claim 3, It is characterized in that The electronic element is an organic electroluminescent device or a photoelectric conversion device.

5. The electronic component according to claim 3, It is characterized in that The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

6. The electronic component according to claim 5, It is characterized in that The electronic component is an organic electroluminescent device, the hole transport layer includes a first hole transport layer and a second hole transport layer, the first hole transport layer is closer to the anode than the second hole transport layer, and the first hole transport layer contains the organic compound.

7. The electronic component according to claim 3, It is characterized in that The electronic component is an organic electroluminescent device, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer contains the organic compound.

8. Electronic devices, It is characterized in that An electronic component comprising any one of claims 3 to 7.

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