Organic compound and electronic component and electronic device using the same

Abstract

The present invention relates to an organic compound and an electronic component and an electronic device using the same. The organic compound has a structure shown in Formula I, and 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 relates to the technical field of organic electroluminescence, and in particular, to an organic compound and an electronic component and an electronic device using the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Such electronic components usually include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

[0003] Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence. When voltage is applied between the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, which are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0004] In the prior art, WO2016087017A1, KR1020110110508A, CN 111094234A, etc. disclose materials that can be used in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the invention

[0005] The purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0006] The first aspect of the present application provides an organic compound having a structure shown in Formula I:

[0007]

[0008] Wherein, X is selected from O, S, C(R9R 10 ) or N(R 11 );

[0009] R9, R 10 and R 11 are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0010] R1, R2, R3 and R4 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 deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

[0011] R1, R2, R3 and R4 are R i Indicates that n1, n2, n3 and n4 are n i Indicates that n i Represents R i The number of, i is a variable, 1, 2, 3 or 4, when i is 1, 2, 3 or 4, n i Select from 0, 1, 2, 3, 4; and when n i When it is greater than 1, any two R i Same or different;

[0012] R5, R6, R7 and R8 are the same or different and are independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms;

[0013] Ar1 and Ar2 are the same or different and are each independently 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;

[0014] L, L1 and L2 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;

[0015] The substituents in Ar1, Ar2, L, L1 and L2 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 deuterated alkyl group having 1 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.

[0016] The organic compound of the present application is composed of a dibenzo six-membered ring spiro diphenyl seven-membered ring The structure formed by connecting the triarylamine structure through a single bond or an arylide, the formed compound has an appropriate torque in space, and this structure can improve the spatial configuration of the molecule, improve the film-forming property of the molecule, and can improve the carrier mobility, thereby improving the efficiency of the device. On the one hand, the dibenzo hexacyclic spirodiphenyl heptad has a higher triplet energy level, which has a good effect on blocking excitons, reduces molecular stacking in space, effectively reduces the possibility of molecular crystallization, greatly improves molecular stability, and improves the life span; on the other hand, the triarylamine structure has excellent hole transport performance, so that the hole transport efficiency of the entire molecule is improved. The organic compound of the present application is applied to an organic electroluminescent device, which can simultaneously improve the efficiency and service life of the device.

[0017] 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.

[0018] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0019] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] 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.

[0021] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0022] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0023] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0024] Figure 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0025] Description of Reference Numerals

[0026] 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

[0027] 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.

[0028] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0029]

[0030] Wherein, X is selected from O, S, C(R9R 10 ) or N(R 11 );

[0031] R9, R 10 and R 11 are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0032] R1, R2, R3 and R4 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 deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

[0033] R1, R2, R3 and R4 are R i Indicates that n1, n2, n3 and n4 are n i Indicates that n i Represents R i The number of i is a variable, which is 1, 2, 3 or 4, n i is selected from 0, 1, 2, 3, 4 (i.e., n1, n2, n3 and n4 are each independently selected from 0, 1, 2, 3, 4); and when n i When it is greater than 1, any two R i Same or different;

[0034] R5, R6, R7 and R8 are the same or different and are independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms;

[0035] Ar1 and Ar2 are the same or different and are each independently 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;

[0036] L, L1 and L2 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;

[0037] The substituents in Ar1, Ar2, L, L1, and L2 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 deuterated alkyl group having 1 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.

[0038] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may but need not occur, and the description includes occasions where the event or environment 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: the situation where two adjacent substituents form a ring and the situation where two adjacent substituents do not form a ring. For another example, "optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3-15-membered ring" means that any two adjacent substituents in Ar1 can be connected to each other to form a saturated or unsaturated 3-15-membered ring, or any two adjacent substituents in Ar1 can also exist independently. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms having one substituent each; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are connected; when there are two adjacent atoms having one substituent each, the two substituents can be fused into a ring.

[0039] In this application, Refers to chemical bonds to other substituents or bonding positions.

[0040] In this application, the descriptions "each independently selected from" and "respectively independently selected from" are interchangeable and should be understood in a broad sense, which 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.

[0041] 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 substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, etc. The number of substituents Rc can be one or more. When two substituents Rc are connected to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the adjacent substituents Rc can exist independently or be fused into a ring with the functional group to which they are connected.

[0042] 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 L1 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.

[0043] 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 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 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, Ji et al.

[0044] In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0045] 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, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, halogenated alkyl groups, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl 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 refers to the total number of carbon atoms in the aryl group and the substituents.

[0046] 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 at least one 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 phenothiazinyl group, a silyfluorenyl 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, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic system type connected by conjugation via carbon-carbon bonds.

[0047] In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

[0048] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl groups, phenyl-substituted dibenzothienyl groups, phenyl-substituted pyridyl 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.

[0049] In the present application, the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may 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, anthracenyl, base.

[0050] In the present application, the number of carbon atoms of the heteroaryl group as a 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, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0051] 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-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0052] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0053] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0054] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0055] In this application, an unpositioned 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 that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0056]

[0057] 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 the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

[0058]

[0059] In the present application, in Formula I, Can be connected to For example, it can be connected to the benzene ring, or to X or R5 to R8, preferably to the benzene ring.

[0060] Optionally, the structure of the organic compound is as shown in Formula II or Formula I-II:

[0061]

[0062] Preferably, the organic compound has a structure as shown in Formula II.

[0063] Specifically, the structure of the organic compound is selected from at least one of the following structures:

[0064]

[0065] Further preferably, the structure of the organic compound is selected from at least one of the following structures:

[0066]

[0067] In one embodiment of the present application, R9, R 10 and R 11 Each is independently selected from an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 5 to 12 carbon atoms.

[0068] Optionally, R9, R 10 and R 11 Each is independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0069] Further optionally, R9, R 10 are each independently methyl or phenyl, R 11 It is phenyl.

[0070] In one embodiment of the present application, R1, R2, R3 and R4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or carbazolyl.

[0071] In one embodiment of the present application, R5, R6, R7 and R8 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

[0072] Optionally, R5, R6, R7 and R8 are each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.

[0073] In one embodiment of the present application, Ar1 and Ar2 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 5 to 20 carbon atoms. For example, Ar1 and Ar2 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 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0074] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated 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;

[0075] Optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 5-13 membered ring;

[0076] Optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 5-13 membered ring.

[0077] Optionally, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0078] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl;

[0079] Optionally, any two adjacent substituents in Ar1 form a cyclopentane, cyclohexane or fluorene ring;

[0080] Optionally, any two adjacent substituents in Ar2 form a cyclopentane, cyclohexane or fluorene ring.

[0081] In one embodiment, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:

[0082]

[0083] 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, trimethylsilyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0084] Optionally, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0085]

[0086]

[0087] Further optionally, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0088]

[0089] In one embodiment of the present application, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. For example, L, L1 and L2 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, 10, 20 carbon atoms.

[0090] Optionally, the substituents in L, L1 and L2 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, and a heteroaryl group having 5 to 12 carbon atoms.

[0091] Alternatively, L, L1 and L2 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 fluorenylene group.

[0092] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0093] In one embodiment, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group Q; the unsubstituted group Q is selected from the group consisting of the following groups:

[0094]

[0095] Wherein, the substituted group Q has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentane, cyclohexane, phenyl or naphthyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0096] Optionally, L, L1 and L2 are each independently selected from a single bond or the following group consisting of:

[0097]

[0098] Further optionally, L, L1 and L2 are each independently selected from a single bond or the following group consisting of:

[0099]

[0100] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] 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.

[0109] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device. Further optionally, the electronic component is a green organic electroluminescent device.

[0110] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound of the present application.

[0111] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is closer to the anode than the second hole transport layer, wherein the second hole transport layer contains the organic compound of the present application.

[0112] In one embodiment, the electronic component is an organic electroluminescent device. Figure 1 As shown, the organic electroluminescent device may include a stacked 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. The first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320.

[0113] Optionally, the anode 100 includes the following anode material, which is preferably a material 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 SnO2:Sb; or conductive polymers 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 including indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0114] Optionally, the hole transport layer 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 this application does not make special provisions for this. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0115]

[0116]

[0117] In one specific embodiment, the first hole transport layer 321 is compound HT-1.

[0118] Optionally, the second hole transport layer 322 is the compound of the present application.

[0119] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest 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 host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0120] The main material of the organic light-emitting layer 330 can 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 on this. The main material can be a single main material or a mixed main material. In one embodiment of the present application, the main material of the organic light-emitting layer 330 is CBP.

[0121] The guest material of the organic light-emitting layer 330 can be selected according 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 guest material include, but are not limited to,

[0122]

[0123] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is Ir(ppy)3.

[0124] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials, and the electron transport material can generally include a metal complex or / and a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, 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. Specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, ET-20, BimiBphen, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below. In one embodiment of the present application, the electron transport layer 340 is composed of ET-20 and LiQ.

[0125]

[0126] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that helps inject electrons 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 their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.

[0127] Alternatively, if Figure 1 As shown, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting 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 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:

[0128]

[0129] In a specific embodiment of the present application, the hole injection layer 310 is m-MTDATA.

[0130] Alternatively, if Figure 1 As shown, an electron injection layer 350 is further 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 alkali metals and organic matter. For example, the electron injection layer 350 includes LiQ.

[0131] According to another embodiment, 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.

[0132] According to a specific implementation mode, Figure 3 As shown, the photoelectric conversion device includes 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. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0133] Optionally, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, in one embodiment of the present application, the solar cell comprises 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 comprises the organic compound of the present application.

[0134] In a third aspect, the present application provides an electronic device, comprising the electronic component provided in the second aspect of the present application.

[0135] According to one embodiment, 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.

[0136] According to another embodiment, 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.

[0137] 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.

[0138] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0139] Synthesis example

[0140] 1. Synthesis of IMA

[0141]

[0142] Under nitrogen protection, raw material a-1 (200g, 869mmol) and dichloromethane (1600mL) were added to the reaction vessel. After dissolving, the temperature was lowered to -30°C and kept warm for 30min. Bromine (139g, 869mmol) was added dropwise to the reaction vessel. After the addition was complete, the reaction was carried out at -30°C to -20°C for 5h. After the reaction was completed, acid water (sulfuric acid: water (v / v) = 10mL: 200mL) was added dropwise to the reaction vessel, extracted with dichloromethane and water, the organic phase was washed with water until neutral, dried with anhydrous sodium sulfate, filtered and concentrated. Recrystallization was performed using solvent toluene: n-heptane (v / v) = 1:4 to obtain a white solid IMA-1 (201.5g, yield 75.7%).

[0143]

[0144] Under nitrogen protection, IMA-1 (200 g, 646 mmol) and tetrahydrofuran (1200 mL) were added to the reaction vessel, dissolved, cooled to -78 ° C, n-butyl lithium (82 g, 775 mmol) was slowly added dropwise, and kept at -78 ° C for 1 h. The raw material a-2 (138.5 g, 646 mmol) was dissolved in tetrahydrofuran (50 mL), added dropwise to the reaction vessel, reacted at -78 ° C for 3 h, and then the reaction was stopped. The organic phase was extracted with ethyl acetate (300 mL) and water, washed with water until neutral, anhydrous sodium sulfate was added, filtered and concentrated, and then passed through a silica gel column with dichloromethane: n-heptane (v / v) = 1:4 as the eluent. The liquid after the column was concentrated to obtain a white solid IMA-2 (241.1 g, yield 85.5%).

[0145]

[0146] Under nitrogen protection, IMA-2 (200 g, 455 mmol), glacial acetic acid (2000 mL) and sulfuric acid (20 mL) were placed in a reaction vessel, refluxed at 60°C for 4 h, and the reaction was stopped. The reaction temperature was lowered to room temperature, extracted with water and dichloromethane, the organic phase was washed with water until neutral, dried with anhydrous sodium sulfate, filtered and concentrated. Recrystallization using solvent dichloroethane: n-heptane (v / v) = 1:5 gave white solid IMA (155.7 g, yield 81.2%).

[0147] The IMX listed in Table 1 was synthesized by referring to the method of IMA, except that raw material 1 was used instead of raw material a-1, wherein the main raw materials used, the intermediates synthesized and the final step yields thereof are shown in Table 1:

[0148] Table 1

[0149]

[0150] 2. Synthesis of IM-I

[0151]

[0152] Under the protection of N2, IMA (10 g, 0.02 mol), p-chlorophenylboronic acid (4.5 g, 0.02 g), tetrakis(triphenylphosphine)palladium (0.11 g, 0.0001 mol), tetrabutylammonium bromide (0.6 g, 0.002 mol), potassium carbonate (5.5 g, 0.04 mol), toluene (60 mL), anhydrous ethanol (20 mL) and deionized water (20 mL) were placed in a 250 mL three-necked flask, and the reaction was stopped after reflux at 80°C for 12 h. The reaction solution was cooled to room temperature, extracted with toluene and water, the organic phase was washed with water until neutral, dehydrated and dried with anhydrous magnesium sulfate, filtered and concentrated, and passed through a silica gel funnel column with toluene as the eluent. The liquid after the column was concentrated and recrystallized using dichloromethane: n-heptane (v / v) = 1:3 to obtain a white solid IMI (8.45 g, yield 85%).

[0153] 3. Synthesis of compounds

[0154]

[0155] Under nitrogen protection, IMA (10 g, 23.7 mmol), aniline (2.2 g, 23.7 mmol) and toluene (80 mL) were placed in a reaction vessel, refluxed for 30 min, cooled to 75°C-85°C, sodium tert-butoxide (3.43 g, 35.7 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.23 g, 0.4 mmol) and tris(dibenzylideneacetone)dipalladium (0.18 g, 0.24 mmol) were added, refluxed for 2 h, the reaction was stopped, the reaction solution was cooled to room temperature, extracted with water and toluene, the organic phase was washed with water until neutral, anhydrous magnesium sulfate was added to dry, filtered and concentrated, passed through a silica gel funnel column with toluene as the eluent, and the liquid after the column was concentrated. Recrystallization was performed using a solvent of dichloromethane: n-heptane (v / v) = 1:4 to obtain a white solid IM 4 (9.8 g, yield 86.5%).

[0156]

[0157] Under nitrogen protection, IM 4 (9.8 g, 20.5 mmol), 4-bromobiphenyl (4.7 g, 20.5 mmol) and toluene (80 mL) were placed in a reaction vessel, refluxed for 30 min, cooled to 75°C-85°C, sodium tert-butoxide (2.9 g, 30.7 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl (0.17 g, 0.4 mmol) and tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) were added, refluxed for 5 h, the reaction was stopped, the reaction solution was cooled to room temperature, extracted with water and toluene, the organic phase was washed with water until neutral, anhydrous magnesium sulfate was added for drying, filtered and concentrated, passed through a silica gel funnel column with toluene as the eluent, and the liquid after the column was concentrated. Recrystallization was performed using a solvent of dichloromethane: n-heptane (v / v) = 1:4 to obtain a white solid compound 4 (10.14 g, yield 78.6%), mass spectrum (m / z) = 630.31 [M+H] + .

[0158] The compounds listed in Table 3 were synthesized by referring to the method of compound 4, except that IM X was used instead of IMA, raw material 3 was used instead of aniline, and raw material 4 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 2:

[0159] Table 2

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] NMR data of some compounds

[0166] Compound 4: 1 H-NMR (400MHz, CD2Cl2): δppm 7.86(s,1H),7.85(d,2H),7.83(s,1H),7.79-7.55(m,9H),7.53-7.51(d,2H),7.35-7.2 5(m,9H),7.24(d,4H),7.12(s,1H),3.53-3.42(m,2H),3.10-3.01(m,2H),1.68(s,6H).

[0167] Compound 176: 1H-NMR (400MHz, CD2Cl2): δppm 8.52(m,1H),7.33-7.31(d,1H),7.98-7.65(m,10H),7.62-7.52(m,5H),7.43-7.40(m,3 H),7.34-7.17(m,8H),7.06(d,1H),3.53-3.42(m,2H),3.10-3.01(m,2H),1.68(s,6H).

[0168] Preparation and performance evaluation of organic electroluminescent devices

[0169] Example 1

[0170] Green organic electroluminescent devices were prepared by the following method

[0171] The thickness is The ITO / Ag / ITO substrate was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness) and prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0172] On the experimental substrate (anode), m-MTDATA was vacuum-deposited to form a layer with a thickness of A hole injection layer (HIL) of 100 mm thick was formed by vacuum evaporating HT-1 on the hole injection layer. The first hole transport layer is formed by a plurality of holes.

[0173] Compound 4 is evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is

[0174] On the second hole transport layer, CBP and Ir(ppy)3 were co-evaporated at an evaporation ratio of 100:8 to form a layer with a thickness of of an organic light-emitting layer (EML).

[0175] On the organic light-emitting layer, ET-20 and LiQ were co-deposited at a 1:1 evaporation ratio to form a layer with a thickness of The electron transport layer (ETL) is formed by evaporating LiQ on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) are vacuum-deposited on the electron injection layer at a deposition rate of 1:9 to form a layer with a thickness of cathode.

[0176] Finally, CP-1 is evaporated on the cathode to form a layer with a thickness of An organic cover layer (CPL) is formed on the organic light-emitting device to complete the manufacturing process.

[0177] Embodiments 2 to 34

[0178] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in the following Table 4 was used instead of Compound 4 when forming the second hole transport layer.

[0179] Comparative Examples 1 to 4

[0180] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound A, B, C, and D were used to replace compound 4 when forming the second hole transport layer.

[0181] The main material structures used in the above embodiments and comparative examples are shown in Table 3 below:

[0182] Table 3

[0183]

[0184] The performance of the devices prepared in the examples and comparative examples was tested, wherein IVL (driving voltage, current efficiency, color coordinates, external quantum efficiency) and lifetime were measured at 20 mA / cm 2 The results are shown in Table 4.

[0185] Table 4

[0186]

[0187] According to the results in Table 4, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the performance of the organic electroluminescent devices of Examples 1 to 34 is improved. Specifically, the luminous efficiency (Cd / A) of the organic electroluminescent devices of Examples 1 to 34 is at least 13.7% higher than that of the comparative examples, the external quantum efficiency is at least 12.62% higher, and the life span is at least 12.85%. Therefore, using the organic compound of the present application as the second hole transport layer of the organic electroluminescent device can improve the efficiency and life span.

[0188] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the protection scope of the present application.

[0189] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not further describe various possible combinations.

[0190] In addition, the various different implementation modes of the present application may be arbitrarily combined, and as long as they do not violate the concept of the present application, they should also be regarded as the contents disclosed in the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula II: Wherein, X is selected from O, S, C(R9R 10 ) or N(R 11 ); R9, R 10 and R 11 are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl or phenyl; R1, R2, R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, deuterated methyl or phenyl; R1, R2, R3 and R4 are R i Indicates that n1, n2, n3 and n4 are n i Indicates that n i Represents R i The number of, i is a variable, 1, 2, 3 or 4, when i is 1, 2, 3 or 4, n i Select from 0, 1, 2, 3, 4; and when n i When it is greater than 1, any two R i Same or different; R5, R6, R7 and R8 are the same or different and are each independently selected from hydrogen or deuterium; Ar1 and Ar2 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 terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuterated methyl, trifluoromethyl or phenyl; L, L1 and L2 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, or a substituted or unsubstituted biphenylene group; The substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

2. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from the group consisting of:

3. The organic compound according to claim 1, wherein L, L1 and L2 are each independently selected from 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, characterized in that The electronic component comprises an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to any one of claims 1 to 4.

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

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

8. The electronic component according to claim 7, wherein: The organic electroluminescent device is a green organic electroluminescent device.

9. An electronic device, characterized in that The electronic device includes the electronic component according to any one of claims 5 to 8.

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