Organic Compounds and Electronic Components and Devices Containing the Same

Abstract

The present application relates to an organic compound and an electronic component and an electronic device comprising the same. The structural formula of the organic compound of the present application is shown in Formula 1. When the organic compound is applied to an organic electroluminescent device, the performance of the device can be significantly improved.

Description

Technical Field

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

[0002] Organic semiconductors are used as functional materials in organic light-emitting diodes (OLEDs), which are a new generation of all-solid-state flat panel display technologies. Currently, they have gradually entered daily life. For example, smartphones, smartwatches, portable notebooks, etc. have all adopted OLED display technology. Compared with other display technologies, OLED technology has the advantages of a wide viewing angle, fast response speed, low driving voltage, a wide display temperature range, and full-color display from the blue to red spectral regions.

[0003] Currently, the research on OLEDs has been very in-depth. The OLED optoelectronic functional materials used in OLED devices can be classified into charge injection and transport materials and light-emitting materials according to their uses; according to the functions of each layer of materials, the charge injection and transport materials can also be divided into electron injection and transport materials, electron blocking materials, hole injection and transport materials, and hole blocking materials; therefore, the OLED optoelectronic functional material film layer that constitutes an OLED device includes at least two or more structures. The OLED device structure used in the industry includes multiple film layers such as a hole injection layer, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. That is to say, the optoelectronic functional materials used in OLED devices at least include hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron transport materials, etc. By adjusting the energy level matching of the functional layer materials and the light-emitting host material, holes and electrons can be made to gather in the light-emitting host layer and collide, causing the light-emitting material to be excited and emit light. Currently, it is still necessary to further improve the performance of OLED displays, such as driving voltage, efficiency, and display life. It is necessary to continuously develop organic light-emitting devices with low-voltage driving, high efficiency, high brightness, and long life to achieve a more practical purpose.

[0004] The hole transport material plays an important role in transferring the holes injected from the anode to the light-emitting layer. A hole transport material with excellent hole mobility is beneficial to the injection balance of carriers in the device, thereby achieving a reduction in the device driving voltage. On the other hand, since the excitons generated in the light-emitting layer will move towards the hole transport layer, eventually causing light emission at the interface between the hole transport layer and the organic light-emitting layer, problems such as color shift and reduced light-emitting efficiency occur. Therefore, in order to improve the efficiency of the organic light-emitting layer, an electron blocking layer needs to be added between the hole transport layer and the organic light-emitting layer to prevent efficiency roll-off and improve the stability of the device.

[0005] Therefore, it is highly necessary to develop a compound with excellent performance that can be used in organic electroluminescent devices. Summary of the Invention

[0006] In view of the above problems existing in the prior art, the purpose of this application is to provide an organic compound, an electronic component, and an electronic device containing the same, and the organic compound can improve the performance of the electronic component and the electronic device.

[0007] The first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0008]

[0009] Wherein, m is 1 or 2,

[0010] R a and R b are the same or different and are each independently selected from methyl or hydrogen;

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

[0012]

[0013] Wherein, represents a chemical bond;

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

[0015] R1, R2, and R3 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, or a heteroaryl group having 3 to 20 carbon atoms;

[0016] R1, R2, and R3 are represented by R i n1, n2, and n3 are represented by n i n i represents the number of R i i is a variable selected from 1, 2, and 3. When i is 1, n i is selected from 0, 1, 2; when i is 2 or 3, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; and when n i is greater than 1, any two R i are the same or different;

[0017] Ar1, Ar2, Ar3 and Ar4 are the same or different, and each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms;

[0018] L a and L b , L1, L2, L3 and L4 are the same or different, and each independently selected from a single bond, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms;

[0019] Ar1, Ar2, Ar3, Ar4, L a and L b , L1, L2, L3 and L4 have substituents that are the same or different, and each independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms or heteroaryl groups having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar3 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar4 form a saturated or unsaturated 3- to 15-membered ring.

[0020] The structure of the organic compound of the present application is that the benzene rings of benzo five-membered / six-membered saturated rings are respectively connected to an arylamine group and a carbazole or arylamine group. This structure can improve the spatial configuration of the molecule, improve the film-forming property of the molecule, and has obvious electron-rich characteristics. When the organic compound of the present application is used in the electron blocking layer and the hole transport layer, it can effectively block electrons from passing through the organic light-emitting layer into the functional layer, thereby reducing the energy transfer barrier between the hole transport layer and the organic light-emitting layer, thereby improving the efficiency of the device and at the same time improving the lifespan of the device.

[0021] The second aspect of the present application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned organic compound.

[0022] The third aspect of the present application provides an electronic device, including the electronic component described in the second aspect.

[0023] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. Description of the Drawings

[0024] The accompanying drawings are used to provide a further understanding of the present application and form a part of the specification. Together with the following detailed description, they are used to explain the present application, but do not constitute a limitation to the present application.

[0025] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0026] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0027] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

[0028] Figure 4 It is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0029] Reference numerals

[0030] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 330, electron blocking layer; 340, organic light-emitting layer; 350, electron transport layer; 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device Detailed description

[0031] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of the present application.

[0032] In a first aspect, the present application provides an organic compound having the structure shown in Formula 1:

[0033]

[0034] Wherein, m is 1 or 2,

[0035] R a and R b are the same or different and each independently selected from methyl or hydrogen;

[0036] M is selected from one of Formula I and Formula II:

[0037]

[0038] Among them, represents a chemical bond;

[0039] Ring A and Ring B are the same or different, and each independently selected from a benzene ring or a fused aromatic ring with 10 to 14 ring carbon atoms;

[0040] R1, R2 and R3 are the same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group with 1 to 10 carbon atoms, a trialkylsilyl group with 3 to 12 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an aryl group with 6 to 20 carbon atoms or a heteroaryl group with 3 to 20 carbon atoms;

[0041] R1, R2 and R3 are represented by R i n1, n2 and n3 are represented by n i n i represents the number of R i i is a variable, selected from 1, 2 and 3. When i is 1, n i is selected from 0, 1, 2; when i is 2 or 3, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; and when n i is greater than 1, any two R i are the same or different;

[0042] Ar1, Ar2, Ar3 and Ar4 are the same or different, and each independently selected from a substituted or unsubstituted aryl group with 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 40 carbon atoms;

[0043] L a 、L b 、L1, L2, L3 and L4 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group with 3 to 30 carbon atoms;

[0044] Ar1, Ar2, Ar3, Ar4, L a 、L bThe substituents in L1, L2, L3 and L4 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 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 or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar3 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar4 form a saturated or unsaturated 3- to 15-membered ring.

[0045] Optionally, in Formula 1, is selected from the group consisting of:

[0046]

[0047] Optionally, the organic compound has the following structure:

[0048]

[0049] Optionally, the organic compound has the following structure:

[0050]

[0051]

[0052] In this application, the terms "optionally" and "optionally" mean that the subsequently described event or circumstance may but need not occur, and this description includes the cases where the thing or circumstance occurs or does not occur. For example, "optionally, any two adjacent substituents ×× form a ring" means that these two substituents may form a ring but do not have to form a ring, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. Another example is "optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3- to 15-membered ring", which means that any two adjacent substituents in Ar2 may be connected to each other to form a 3- to 15-membered ring, or any two adjacent substituents in Ar2 may also exist independently of each other.

[0053] "Any two adjacent" may include having two substituents on the same atom, and may also include having 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 commonly attached; when there is one substituent on each of two adjacent atoms, the two substituents may be fused into a ring.

[0054] In the present application, the fluorenyl group may be substituted by one or two or more substituents. In the case where the above-mentioned fluorenyl group is substituted, it may be: etc., but not limited thereto.

[0055] In the present application, the description methods "each... is independently", "... are independently respectively", and "... are independently selected from" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can also mean that within the same group, the specific options expressed between 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, chlorine", which means that in formula Q-1, 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; in formula Q-2, each benzene ring of the biphenyl has q substituents R", the number q of the 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.

[0056] In the present application, the term "substituted or unsubstituted" means that the functional group described after this term may have or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, namely Rc, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, etc.

[0057] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, if L is a substituted arylene group with 12 carbon atoms, then all the carbon atoms of the arylene group and its substituents are 12.

[0058] In the present application, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused polycyclic aryl group, two or more monocyclic aryl groups conjugated through carbon-carbon bonds, a monocyclic aryl group and a fused polycyclic aryl group conjugated through carbon-carbon bonds, or two or more fused polycyclic aryl groups conjugated through carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as the aryl groups in the present application. Among them, the fused polycyclic aryl group can include, for example, a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), etc. The aryl group 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 groups. Examples of aryl groups can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, etc. In the present application, the arylene group involved refers to a divalent group formed by further removing one hydrogen atom from an aryl group.

[0059] In the present application, a substituted aryl group can 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, haloalkyl groups, etc. It should be understood that the number of carbon atoms in a 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 refers to the total number of carbon atoms in the aryl group and the substituents being 18.

[0060] In the present application, a heteroaryl refers to a monovalent aromatic ring or its derivative containing at least one heteroatom in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se, and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thiophenyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., without being limited thereto. Among them, thiophenyl, furyl, phenanthrolinyl, etc. are heteroaryls of the single aromatic ring system type, and N-phenylcarbazolyl, N-pyridylcarbazolyl are heteroaryls of the polycyclic system type conjugated through carbon-carbon bonds. In the present application, the sub-heteroaryl involved refers to a divalent group formed by further removing one hydrogen atom from the heteroaryl.

[0061] In the present application, the substituted heteroaryl can be such that one or more than two hydrogen atoms in the heteroaryl are substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0062] In the present application, as substituents of Ar1, Ar2, Ar3, Ar4, L a 、L b 、L1, L2, L3, and L4, the number of carbon atoms of the aryl group can be 6-20. 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, phenanthryl, anthracenyl, yl.

[0063] In the present application, as substituents of Ar1, Ar2, Ar3, Ar4, L a 、L b, the number of carbon atoms of the heteroaryl group of the substituents in L1, L2, L3, and L4 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, triazinyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl.

[0064] In the present application, the non-positioning connecting bond refers to a 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 penetrated by the bond, and the other end is connected to the rest of the compound molecule.

[0065] 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 can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. 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, etc.

[0066] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0067] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0068] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0069] In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentane, cyclohexane, adamantane.

[0070] 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-positioning connecting bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connecting manner shown in formulas (f-1) to (f-10).

[0071]

[0072] As another example, as shown in the following formula (X'), the dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned linking bond extending from the middle of one of the benzene rings on one side, and the meanings it represents include any possible linking modes shown in the formulas (X'-1) to (X'-4).

[0073]

[0074] Preferably, m is 1, and R a and R b are both methyl or hydrogen; when m is 2, R a and R b are both hydrogen.

[0075] In one embodiment of the present application, ring A and ring B are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring. For example, both ring A and ring B are benzene rings; or ring A is a naphthalene ring and ring B is a benzene ring; or ring B is a naphthalene ring and ring A is a benzene ring.

[0076] In one embodiment of the present application, Ar1, Ar2, Ar3 and Ar4 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms. For example, Ar1, Ar2, Ar3 and Ar4 are 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.

[0077] Preferably, the substituents in Ar1, Ar2, Ar3 and Ar4 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, trimethylsilyl, trifluoromethyl, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 5- to 13-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 5- to 13-membered ring; optionally, any two adjacent substituents in Ar3 form a saturated or unsaturated 5- to 13-membered ring; optionally, any two adjacent substituents in Ar4 form a saturated or unsaturated 5- to 13-membered ring.

[0078] Optionally, Ar1, Ar2, Ar3, and Ar4 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.

[0079] Preferably, the substituents in Ar1, Ar2, Ar3, and Ar4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; optionally, any two adjacent substituents in Ar1 form a fluorene ring; optionally, any two adjacent substituents in Ar2 form a fluorene ring; optionally, any two adjacent substituents in Ar3 form a fluorene ring; optionally, any two adjacent substituents in Ar4 form a fluorene ring.

[0080] Optionally, Ar1, Ar2, Ar3, and Ar4 are each independently selected from substituted or unsubstituted group W, and the unsubstituted group W is selected from the following groups:

[0081]

[0082] Wherein, the substituted group W has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and when the number of substituents is greater than 1, the substituents are the same or different.

[0083] Optionally, Ar1, Ar2, Ar3, and Ar4 are each independently selected from the group consisting of the following groups:

[0084]

[0085] Further optionally, Ar1, Ar2, Ar3, and Ar4 are each independently selected from the following groups:

[0086]

[0087] In one embodiment of the present application, L a 、L b 、L1, L2, L3, and L4 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene having 5 to 20 carbon atoms. For example, L a 、L b, L1, L2, L3 and L4 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0088] Preferably, the substituents in L a , L b , L1, L2, L3 and L4 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0089] Optionally, L a , L b , L1, L2, L3 and L4 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 terphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0090] Preferably, the substituents in L a , L b , L1, L2, L3 and L4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0091] Optionally, L a , L b , L1, L2, L3 and L4 are each independently selected from a single bond and a substituted or unsubstituted group Q; wherein, the unsubstituted group Q is selected from the group consisting of the following groups:

[0092]

[0093] Among them, the substituted group Q has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0094] Optionally, L a , L b , L1, L2, L3 and L4 are each independently selected from a single bond or the group consisting of the following groups:

[0095]

[0096] Further optionally, L a , L b , L1, L2, L3 and L4 are each independently selected from the group consisting of a single bond or the following groups:

[0097]

[0098] Optionally, R1, R2 and R3 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentane, cyclohexane, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0099] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104] In a second aspect, the present application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of the present application.

[0105] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound described in the present application.

[0106] Optionally, the functional layer includes an electron blocking layer, and the electron blocking layer contains the organic compound described in the present application.

[0107] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0108] In one embodiment, the electronic component is an organic electroluminescent device. As Figure 1 shown, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an electron blocking layer 330, an organic light emitting layer 340, an electron transport layer 350 and a cathode 200 which are sequentially stacked.

[0109] In a specific embodiment, the organic electroluminescent device is a blue organic electroluminescent device.

[0110] Optionally, the anode 100 includes the following anode materials, which are optionally materials with a large work function (work function) that contribute to hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO∶Al or SnO2∶Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, it includes a transparent electrode containing indium tin oxide (ITO) as the anode.

[0111] Optionally, the hole transport layer 320 includes one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and those skilled in the art can select them with reference to the prior art. For example, the material of the hole transport layer 320 is selected from the group consisting of the following compounds:

[0112]

[0113]

[0114] In a specific embodiment, the hole transport layer 320 is the compound HT-1. In another specific embodiment, the hole transport layer 320 contains the organic compound described in the present application.

[0115] Optionally, the electron blocking layer 330 includes one or more electron blocking materials, which can be selected from carbazole polymers or other types of compounds, and the present application does not make special limitations thereto. In a specific embodiment, the electron blocking layer 330 contains the organic compound described in the present application. In another specific embodiment, the electron blocking layer 330 is the compound EB-1.

[0116] Optionally, the organic light-emitting layer 340 can be composed of a single light-emitting layer material, or can include a host material and a doping material. Optionally, the organic light-emitting layer 340 is composed of a host material and a doping material. The holes injected into the organic light-emitting layer 340 and the electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the doping material, so that the doping material can emit light.

[0117] The host material of the organic light-emitting layer 340 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, and this application does not impose special restrictions on this. The host material can be a single host material or a mixed host material.

[0118] In an embodiment of this application, the host material of the organic light-emitting layer 340 is BH-1.

[0119] The doping material of the organic light-emitting layer 340 can be selected with reference to the prior art. For example, it can be selected from iridium(III) organometallic complexes, platinum(II) organometallic complexes, ruthenium(II) complexes, beryllium complexes, etc. Specific examples of the doped materials include, but are not limited to,

[0120]

[0121] In an embodiment of this application, the doping material of the organic light-emitting layer 340 is BD-1.

[0122] Optionally, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials usually can contain metal complexes or / and nitrogen-containing heterocyclic derivatives. Among them, the metal complex materials can be selected from, for example, LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivatives can be aromatic rings with a nitrogen-containing six-membered ring or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as ET-1, Bphen, NBphen, DBimiBphen, BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroaryl nitrogen as shown in the following structure. In an embodiment of this application, the electron transport layer 350 is composed of ET-1 and LiQ.

[0123]

[0124] In this application, the cathode 200 can include a cathode material, which is a material with a small work function that helps the electron injection material reach the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. It is preferably to include a metal electrode containing magnesium and silver as the cathode.

[0125] Optionally, as Figure 1As shown, a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not make special restrictions on this. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0126]

[0127] In a specific embodiment of this application, the hole injection layer 310 is HAT-CN.

[0128] Optionally, as Figure 1 shown, an electron injection layer 360 is further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic compounds. For example, the electron injection layer 360 includes Yb. In a specific embodiment of this application, the electron injection layer 360 is LiF.

[0129] According to another embodiment, the electronic component is a photoelectric conversion device. As Figure 3 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 contains the organic compound provided in this application.

[0130] According to a specific embodiment, as Figure 3 shown, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 370, an electron transport layer 350, and a cathode 200 that are sequentially stacked.

[0131] Optionally, the photoelectric conversion device is a solar cell, especially an organic thin film solar cell. In an embodiment of this application, the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode that are sequentially stacked, wherein the hole transport layer 320 contains the organic compound of this application.

[0132] The third aspect of this application provides an electronic device, including the electronic component provided in the second aspect of this application.

[0133] According to an embodiment, as Figure 2As shown, the electronic device is the 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, and can include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0134] According to another embodiment, as Figure 4 shown, the electronic device is the 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 photodetector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0135] The following combines synthesis examples to specifically illustrate the synthesis method of the organic compound of the present application, but the present application is not limited thereby.

[0136] Compounds for which the synthesis method is not mentioned in the present application are all raw material products obtained through commercial channels.

[0137] Synthesis Example

[0138] 1. Synthesis of IM I-X-1

[0139] Synthesis of IM I-B-1

[0140]

[0141] Under nitrogen protection, 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (60 g, 228.39 mmol) was added to a 1 L three-necked flask, and then 800 mL of dichloromethane solution was added. The temperature was lowered to -30 °C and kept warm. Br2 (40.15 g, 251.23 mmol) was added dropwise, and the addition was completed in about 35 min. The temperature was maintained at -30 °C to -20 °C for reaction for 5 h. Then, 200 mL of H2SO4 (1 mol / L) solution was added dropwise to the reaction solution. Subsequently, the reaction solution was washed with water until neutral, the organic phases were combined and dried with MgSO4 for 30 min, and then the solvent was removed by distillation under reduced pressure. Recrystallization with dichloroethane / n-heptane (volume ratio 1:3) gave a grayish-white solid IM I-B-1 (51.54 g, yield 65.2%).

[0142] IM I-C-1 was synthesized by referring to the method of IM I-B-1, except that raw material 1 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene. The main raw materials used, the synthesized IM I-C-1 and its yield are shown in Table 1.

[0143] Table 1

[0144]

[0145] 2. Synthesis of IM-X

[0146] (1) Synthesis of IM I-A

[0147]

[0148] Under nitrogen protection, carbazole (40 g, 239.22 mmol), 6,7-dibromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (82.80 g, 239.22 mmol), copper(I) iodide (0.91 g, 4.78 mmol), potassium carbonate (66.12 g, 478.44 mmol), 1,10-phenanthroline (21.56 g, 119.61 mmol) and 18-crown-6 (0.63 g, 2.39 mmol) were successively added to a 1 L three-necked flask. Then 500 mL of DMF was added, and nitrogen was continuously passed for 20 min. The mixture was slowly heated to reflux and stirred for 24 h. After cooling to room temperature, the reaction solution was added to 2 L of water to remove DMF, extracted with dichloromethane, dried with anhydrous magnesium sulfate for 30 min, and then the solvent was removed by distillation under reduced pressure. The residue was chromatographed on a silica gel column with dichloromethane / petroleum ether (volume ratio 1:2) to obtain a grayish-white solid IM I-A (76.02 g, yield 73.5%).

[0149] IM I-X listed in Table 2 was synthesized by referring to the same method as that for IM I-A, except that raw material 2 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and raw material 3 was used instead of carbazole. The main raw materials used, the synthesized IM I-X and their yields are shown in Table 2.

[0150] Table 2

[0151]

[0152] (2) Synthesis of IM I-G

[0153]

[0154] Under nitrogen protection, 4-(9-carbazolyl)phenylboronic acid (50 g, 174.14 mmol), 6,7-dibromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (72.32 g, 208.96 mmol), tetrabutylammonium bromide (1.12 g, 3.48 mmol), potassium carbonate (48.13 g, 348.27 mmol), toluene (400 mL), ethanol (150 mL) and water (100 mL) were successively added to a 1 L three-necked flask. Stirring was started and nitrogen protection was applied. The temperature was raised to 50 °C - 60 °C, and tetrakis(triphenylphosphine)palladium (10.06 g, 8.70 mmol) was quickly added. Then, the temperature was further raised to 70 °C - 75 °C and refluxed for 18 h. After the reaction was completed, the temperature was lowered to room temperature, and the mixture was extracted with toluene. The organic phase was washed with water until neutral, dried, filtered, and concentrated. Recrystallization was carried out with a mixed solvent of dichloromethane and n-heptane until LC>99%. After drying, a white solid IM I-G (61.09 g, yield 69.1%) was obtained.

[0155] IM I-X was synthesized by referring to the method of IM I-G, except that raw material 4 was used instead of 6,7-dibromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene, and raw material 5 was used instead of 4-(9-carbazolyl)phenylboronic acid. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0156] Table 3

[0157]

[0158] (3) Synthesis of IM I-H

[0159]

[0160] Under nitrogen protection, diphenylamine (30 g, 174.14 mmol), 6,7-dibromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (72.32 g, 208.96 mmol) and toluene (300 mL) were successively added to a 500 mL three-necked flask. It was heated to completely dissolve and become clear, and then tris(dibenzylideneacetone)dipalladium (1.69 g, 1.77 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.45 g, 3.54 mmol) and sodium tert-butoxide (25.55 g, 265.91 mmol) were added. It was heated to 108 °C under nitrogen protection and stirred for 4 h; then it was cooled to room temperature. The reaction solution was washed with water and then dried with magnesium sulfate. After filtration, the filtrate was passed through a silica gel funnel to remove the catalyst, and then the solvent was removed under reduced pressure to obtain a yellow solid crude product; the crude product was recrystallized and purified with a mixed solvent of dichloromethane and n-heptane to obtain IM I-H (64.43 g, yield 83.7%).

[0161] Synthesize IMI-K by referring to the same method as IMI-H, except that N-phenyl-4-biphenylamine is used instead of diphenylamine to obtain IMI-K (18.1 g, yield 69.5%).

[0162]

[0163] 3. Synthesis of IMI-X-La:

[0164] (1) Synthesis of IMI-A-L1

[0165]

[0166] Charge IMI-A (15.0 g, 34.69 mmol), p-chlorophenylboronic acid (5.7 g, 36.42 mmol), tetrabutylammonium bromide (0.22 g, 0.69 mmol), potassium carbonate (9.69 g, 69.38 mmol), toluene (120 mL), ethanol (40 mL) and water (20 mL) into a 250 mL three-necked flask. Start stirring and protect with nitrogen. Heat up to 50 °C - 60 °C, and quickly add tetrakis(triphenylphosphine)palladium (2.0 g, 1.73 mmol). Then continue to heat up to 70 °C - 75 °C for reflux reaction for 12 h. After the reaction is completed, cool to room temperature, extract with dichloromethane, wash the organic phase with water until neutral, dry, filter and concentrate. Recrystallize with a mixed solvent of ethyl acetate and petroleum ether until LC > 98%. Dry to obtain a white solid IMI-A-L1 (11.62 g, yield 72.2%).

[0167] Synthesize the intermediate IMI-X-La listed in Table 4 by referring to the same method as IMI-A-L1, except that IMI-X is used instead of IMI-A, and raw material 6 is used instead of p-chlorophenylboronic acid. The main raw materials used, the synthesized intermediates and their yields are shown in Table 4.

[0168] Table 4

[0169]

[0170]

[0171] (2) Synthesis of IMI-C-L1

[0172]

[0173] Add isopropyl acetate (200 mL) to a 500 mL three-necked flask, and then add IM I-C (20.00 g, 46.25 mmol), bis(pinacolato)diboron (14.09 g, 55.50 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.85 g, 0.93 mmol), 2-(dicyclohexylphosphino)-2',6'-dimethoxybiphenyl (0.88 g, 1.85 mmol), and potassium acetate (6.81 g, 69.38 mmol). Heat to 85 °C - 90 °C under nitrogen protection and stir for 24 h. Then cool to room temperature, precipitate the product, filter by suction and wash the product until neutral. Dissolve in toluene, remove the catalyst by column chromatography, then evaporate the solvent under reduced pressure and recrystallize with toluene to obtain IM I-C-L1-1 (16.45 g, yield 74.2%).

[0174] Add IM I-C-L1-1 (15.0 g, 31.26 mmol), 1,4-dideuterio-1-bromo-4-biphenyl (7.88 g, 36.42 mmol), tetrabutylammonium bromide (0.22 g, 0.69 mmol), potassium carbonate (9.69 g, 69.38 mmol), toluene (120 mL), ethanol (40 mL), and water (20 mL) to a 250 mL three-necked flask. Start stirring and protect with nitrogen. Heat to 50 °C - 60 °C, and quickly add tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.73 mmol). Then continue to heat to 70 °C - 75 °C and reflux for 12 h. After the reaction is completed, cool to room temperature, extract with dichloromethane, wash the organic phase until neutral, dry, filter, and concentrate. Recrystallize with a mixed solvent of toluene and n-heptane and dry to obtain a white solid IM I-C-L1 (10.22 g, yield 68.2%).

[0175] 4. Synthesis of compounds

[0176] Synthesis of compound 5

[0177]

[0178] Add toluene (200 mL) to a 500 mL flask, and then add IM I-A (26.83 g, 62.04 mmol), 4-aminobiphenyl (10 g, 59.09 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.57 g, 0.59 mmol), 2-(dicyclohexylphosphino)-2',6'-dimethoxybiphenyl (0.57 g, 1.18 mmol), and sodium tert-butoxide (8.48 g, 88.64 mmol). Heat to 108 °C under nitrogen protection and stir for 4 h. Then cool to room temperature, wash the reaction solution with water and add magnesium sulfate for drying. Filter and remove the solvent from the filtrate under reduced pressure to obtain a yellow solid crude product. Then recrystallize and purify the crude product with a toluene system to obtain IM I-A-N (23.69 g, yield 77.0%).

[0179]

[0180] Add toluene (80 mL) into a 250 mL three-necked flask, and then add IMI-A-N (10 g, 19.20 mmol), 4-bromobiphenyl (4.7 g, 20.16 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.18 g, 0.19 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.18 g, 0.38 mmol) and sodium tert-butoxide (2.75 g, 28.81 mmol). Heat to 108 °C under nitrogen protection and stir for 4 h; then cool to room temperature. Wash the reaction solution with water, add magnesium sulfate for drying, filter, and remove the solvent under reduced pressure from the filtrate; Recrystallize and purify the crude product using a toluene system to obtain a white solid compound 5 (8.91 g, yield 53.05%), and the mass spectrum (m / z) = 673.3 [M+H] + 。

[0181] Synthesize the compounds in Table 5 according to the same method as that for compound 5, except that raw material 7 is used instead of IMI-A, raw material 8 is used instead of 3-aminobiphenyl, and raw material 9 is used instead of 3-bromodibenzothiophene. Among them, the main raw materials used, the synthesized compounds and their yields and mass spectra in the last step are shown in Table 5.

[0182] Table 5

[0183]

[0184]

[0185]

[0186] The NMR data of the compounds are shown in Table 6:

[0187] Table 6

[0188]

[0189] Preparation and evaluation of organic electroluminescent devices:

[0190] Example 1: Preparation of blue organic electroluminescent devices

[0191] The thickness of The ITO / Ag / ITO substrate is cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness). Using the photolithography process, it is fabricated into an experimental substrate with an anode and an insulating layer pattern, and ultrasonic washing is carried out for 10 min by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is successively carried out with isopropanol, acetone, and methanol and then dried, and then it is transported to a plasma cleaner. Then, after the above substrate is cleaned with oxygen plasma for 5 min, the substrate is transported to a vacuum evaporator.

[0192] First, HAT-CN is vacuum-evaporated on the experimental substrate (anode) to form a hole injection layer (HIL) with a thickness of , and then HT-1 is vacuum-evaporated on the hole injection layer to form a hole transport layer (HTL) with a thickness of .

[0193] Compound 5 is vacuum-evaporated on the hole transport layer to form an electron blocking layer (EBL) with a thickness of .

[0194] On the electron blocking layer, compound BH-1 and compound BD-1 are co-evaporated at an evaporation ratio of 97%:3% to form an organic light-emitting layer (blue light-emitting layer, B-EML) with a thickness of .

[0195] On the organic light-emitting layer, ET-1 and LiQ are co-evaporated at an evaporation ratio of 1:1 to form an electron transport layer (ETL) with a thickness of , and then LiF is evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of , and then magnesium (Mg) and silver (Ag) are vacuum-evaporated on the electron injection layer at an evaporation rate of 1:9 to form a cathode with a thickness of .

[0196] Finally, CP-1 is evaporated on the cathode to form an organic capping layer (CPL) with a thickness of , and the device is sealed in a glove box, thus completing the fabrication of the blue organic light-emitting device.

[0197] Examples 2 to 16:

[0198] Except that when forming the electron blocking layer, the compound shown in Table 8 is used to replace compound 5, an organic light-emitting device is prepared by the same method as in Example 1.

[0199] Comparative Examples 1 to 2:

[0200] Except that when forming the electron blocking layer, compound A and compound B are used to replace compound 5, an organic light-emitting device is prepared by the same method as in Example 1.

[0201] The main material structures used in the above examples and comparative examples are shown in Table 7:

[0202] Table 7

[0203]

[0204] The performance of the devices prepared in the examples and comparative examples was tested. Among them, the IVL (driving voltage, current efficiency, color coordinates, external quantum efficiency) data was tested at a current density of 10 mA / cm 2 and the T95 lifetime was tested at a current density of 15 mA / cm 2 The results are shown in Table 8.

[0205] Table 8

[0206]

[0207]

[0208] As can be seen from Table 8, when the compound of the present application is used as the electron blocking layer material in the organic electroluminescent device, compared with the device performances of Examples 1-16 and Comparative Examples 1-2, the luminous efficiency is increased by at least 16.92%, the external quantum efficiency is increased by at least 11.3%, and the T95 lifetime is increased by at least 13.8%.

[0209] Example 17: Preparation of a blue organic electroluminescent device

[0210] An ITO / Ag / ITO substrate with a thickness of was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness). Using a photolithography process, an experimental substrate with an anode and an insulating layer pattern was prepared, and ultrasonic washing was carried out for 10 min by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was carried out successively with isopropyl alcohol, acetone, and methanol and then dried, and then transported to a plasma cleaner. Then, the above substrate was cleaned with oxygen plasma for 5 min, and then the substrate was transported to a vacuum evaporation machine.

[0211] First, HAT-CN was vacuum-evaporated on the experimental substrate (anode) to form a hole injection layer (HIL) with a thickness of , and then Compound 137 was vacuum-evaporated on the hole injection layer to form a hole transport layer (HTL) with a thickness of .

[0212] EB-1 was vacuum-evaporated on the hole transport layer to form an electron blocking layer (EBL) with a thickness of .

[0213] On the electron blocking layer, compound BH-1 and compound BD-1 are co-evaporated at an evaporation ratio of 97%:3% to form an organic light-emitting layer (blue light-emitting layer, B-EML) with a thickness of .

[0214] On the organic light-emitting layer, ET-1 and LiQ are co-evaporated at an evaporation ratio of 1:1 to form an electron transport layer (ETL) with a thickness of . Then, LiF is evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of . Then, magnesium (Mg) and silver (Ag) are vacuum-evaporated on the electron injection layer at an evaporation rate of 1:9 to form a cathode with a thickness of .

[0215] Finally, CP-1 is evaporated on the cathode to form an organic capping layer (CPL) with a thickness of , and the device is sealed in a glove box, thus completing the fabrication of the blue organic light-emitting device.

[0216] Examples 18 - 19:

[0217] An organic light-emitting device is prepared by the same method as in Example 17, except that when forming the hole transport layer, the compound shown in Table 9 is used to replace compound 137.

[0218] Comparative Examples 3 - 4:

[0219] An organic light-emitting device is prepared by the same method as in Example 17, except that when forming the hole transport layer, compound C and compound D are used to replace compound 137.

[0220] Table 9

[0221]

[0222] As can be seen from Table 9, when the compound of the present application is used as the hole transport material in an organic light-emitting device, compared with the device performance of Examples 17 - 20 and Comparative Examples 3 - 4, the luminous efficiency is increased by at least 24.4%, the external quantum efficiency is increased by at least 19.96%, and the T95 lifetime is increased by at least 16.45%.

[0223] The preferred embodiments of the present application have been described in detail above. However, the present application is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all fall within the protection scope of the present application.

[0224] In addition, it should be noted that, for the various specific technical features described in the above specific embodiments, they can be combined in any suitable manner without contradiction. To avoid unnecessary repetition, this application will not separately describe various possible combination methods.

[0225] In addition, any combination can also be made among various different embodiments of this application, as long as it does not violate the idea of this application, it should also be regarded as the content disclosed in this application.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: wherein m is 1 or 2, R a and R b are the same or different and each independently selected from methyl or hydrogen; M is selected from Formula II: Among them, represents a chemical bond; Ring A and Ring B are the same and are each selected from benzene rings; R1, R2, and R3 are the same or different and are each independently selected from deuterium, phenyl; R1, R2, and R3 are represented by R i n1, n2, and n3 are represented by n i n i represents the number of R i i is a variable selected from 1, 2, and 3. When i is 1, n i is selected from 0, 1, 2; when i is 2 or 3, n i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; and when n i is greater than 1, any two R i are the same or different; L a , L1, and L2 are each independently selected from a single bond and phenylene; L b selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, and a substituted or unsubstituted fluoreneylene; L b The substituents in it are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl; Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, or phenyl; The organic compound does not include 2. The organic compound according to claim 1, wherein, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

3. The organic compound according to claim 1, wherein, L a , L1, and L2 are each independently selected from the group consisting of a single bond or the following groups: L b selected from the group consisting of a single bond or the following groups:

4. The organic compound according to claim 1, wherein, The organic compound is selected from the group consisting of the following compounds:

5. 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; characterized in that, The functional layer contains the organic compound described in any one of claims 1 to 4.

6. The electronic component according to claim 5, wherein, The electronic component is an organic electroluminescent device or a photoelectric conversion device.

7. The electronic component according to claim 5, wherein, The functional layer includes a hole transport layer, and the hole transport layer contains the organic compound.

8. The electronic component according to claim 5, wherein, The functional layer includes an electron blocking layer, and the electron blocking layer contains the organic compound.

9. An electronic device, characterized in that, An electronic component described in any one of claims 5 to 8 is included.

Images