Organic compound, electronic component and electronic device containing the same

Abstract

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

Description

Technical Field

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

[0002] With the development of electronic technology and the progress of materials science, the research scope of electronic components for electroluminescence or photoelectric conversion is becoming more and more extensive. Among them, organic electroluminescent devices, also known as organic light-emitting diodes, refer to the phenomenon that organic light-emitting materials emit light under the action of an electric field and are excited by current. 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. 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 arranged in sequence. When a voltage is applied to 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 to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] Organic charge transport materials are organic semiconductor materials that can achieve directional, orderly and controllable migration of carriers under the action of an electric field to transport charges when carriers (electrons or holes) are injected. This type of material requires excellent electron-donating properties, low ionization potential, high hole mobility, good solubility and amorphous film-forming properties, strong fluorescence properties and photostability. At present, hole transport layer materials are mainly poly(p-phenylene vinylene), triarylamines, hydrazones, butadiene, etc. The excellent performance of triarylamine materials is one of the research hotspots, and the prior art discloses materials that can be used to prepare hole transport layers in organic electroluminescent devices. However, the existing triarylamine hole transport layer materials perform poorly in terms of voltage, luminous efficiency, power and life in the device, and there is a lot of room for improvement. Therefore, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the invention

[0004] In view of the above-mentioned problems existing in the prior art, the purpose of the present application is to provide an organic compound and an electronic component and an electronic device containing the same, wherein the organic compound can improve the performance of the electronic component and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.

[0005] In order to achieve the above-mentioned invention object, the present application adopts the following technical solutions:

[0006] According to the first aspect of the present application, an organic compound is provided, having a structure represented by Formula 1:

[0007]

[0008] Among them, each R 1 , R 2 , R 3 and R 4 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms;

[0009] R 5 , R 6 , R 7 and R 8 are independently selected from hydrogen or the structure shown in Formula 1-1, and R 5 , R 6 , R 7 and R 8 At least one of the structures is selected from the structure shown in Formula 1-1;

[0010] L, L 1 and L 2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0011] Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] Ar 2 A group selected from the group shown in formula 1-2;

[0013] X is selected from C(R 11 R 12 ), O or S;

[0014] Each R 9 and R 10 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms;

[0015] R 11 and R 12 are the same or different, and are independently selected from an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms;

[0016] n 1 For R 1The number of is selected from 0, 1, 2, 3 or 4. 1 When it is greater than 1, any two R 1 Same or different;

[0017] n 2 For R 2 The number of is selected from 0, 1, 2, 3 or 4. 2 When it is greater than 1, any two R 1 Same or different;

[0018] n 3 For R 3 The number of is selected from 0, 1 or 2, when n 3 When it is greater than 1, any two R 3 Same or different;

[0019] n 4 For R 4 The number of is selected from 0, 1, 2, 3 or 4. 4 When it is greater than 1, any two R 4 Same or different;

[0020] n 9 For R 9 The number of is selected from 0, 1, 2 or 3. 9 When it is greater than 1, any two R 9 Same or different;

[0021] n 10 For R 10 The number of is selected from 0, 1, 2, 3 or 4. 10 When it is greater than 1, any two R 10 Same or different;

[0022] The L, L 1 , L 2 and Ar 1 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 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 5 to 20 carbon atoms;

[0023] Optionally, Ar 1 Any two adjacent substituents in the form a ring.

[0024] According to a second aspect of the present application, an electronic component is provided, 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 above-mentioned organic compound.

[0025] According to a third aspect of the present application, an electronic device is provided, comprising the electronic component described in the second aspect.

[0026] The organic compound of the present application connects the aromatic amine group to a special large planar conjugated group and a dibenzo pentacyclic group, wherein the special conjugated group used in the organic compound of the present application has a higher T1 value, which is conducive to the transmission of carriers and energy. This connection mode of the present application makes the compound molecule have a high HOMO orbital coverage and a strong polarity, so as to have a good hole mobility. The organic compound of the present application can effectively avoid intermolecular stacking and improve the film-forming property of the compound. When the organic compound of the present application is used as a hole transport layer material of an organic electroluminescent device, the operating voltage of the device can be significantly reduced, and the efficiency and life of the device can be improved.

[0027] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] 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.

[0029] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0030] Figure 2 It is a structural schematic diagram of an electronic device of the present application.

[0031] Reference numerals

[0032] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0033] 320, hole transport layer 330, electron blocking layer 340, organic light emitting layer 350, electron transport layer

[0034] 360. Electron injection layer 400. Electronic device DETAILED DESCRIPTION

[0035] 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.

[0036] In a first aspect, the present application provides an organic compound having a structure represented by Formula 1:

[0037]

[0038] Among them, each R 1 , R 2 , R 3 and R 4 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms;

[0039] R 5 , R 6 , R 7 and R 8 are independently selected from hydrogen or the structure shown in Formula 1-1, and R 5 , R 6 , R 7 and R 8 At least one of the structures is selected from the structure shown in Formula 1-1;

[0040] L, L 1 and L 2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0041] Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0042] Ar 2 A group selected from the group shown in formula 1-2;

[0043] X is selected from C(R 11 R 12 ), O or S;

[0044] Each R 9 and R 10 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms;

[0045] R 11 and R 12 are the same or different, and are independently selected from an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms;

[0046] n 1 For R 1The number of is selected from 0, 1, 2, 3 or 4. 1 When it is greater than 1, any two R 1 Same or different;

[0047] n 2 For R 2 The number of is selected from 0, 1, 2, 3 or 4. 2 When it is greater than 1, any two R 1 Same or different;

[0048] n 3 For R 3 The number of is selected from 0, 1 or 2;

[0049] n 4 For R 4 The number of is selected from 0, 1, 2, 3 or 4. 4 When it is greater than 1, any two R 4 Same or different;

[0050] n 9 For R 9 The number of is selected from 0, 1, 2 or 3. 9 When it is greater than 1, any two R 9 Same or different;

[0051] n 10 For R 10 The number of is selected from 0, 1, 2, 3 or 4. 10 When it is greater than 1, any two R 10 Same or different;

[0052] The L, L 1 , L 2 ,Ar 1 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 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 5 to 20 carbon atoms;

[0053] Optionally, Ar 1 Any two adjacent substituents in the form a ring.

[0054] In the present application, the fluorenyl group may be substituted by 1 or 2 substituents, wherein, when the fluorenyl group is substituted, it may be: etc., but not limited thereto.

[0055] In this application, the descriptions "each ... is independently" and "... are independently" and "... are independently selected from" are interchangeable and should be understood in a broad sense, 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.

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

[0057] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms. 1 If it is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents on the arylene group is 12.

[0058] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Wherein, 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. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0059] In the present application, terphenyl includes

[0060] In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.

[0061] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms 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 benzothiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. Among them, thienyl, furanyl, phenanthroline, etc. are heteroaryl groups of single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of polycyclic system type connected by carbon-carbon bond conjugation. In this application, the heteroaryl group involved refers to a divalent group formed by further losing a hydrogen atom of the heteroaryl group.

[0062] 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, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0063] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can be 6-25, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25.

[0064] In the present application, specific examples of aryl as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, base.

[0065] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be 5-20, for example, the number of carbon atoms can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20.

[0066] In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to, triazine, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl, carbazolyl, and N-phenylcarbazolyl.

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

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

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

[0070] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl and cyclohexyl.

[0071] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that penetrate the bicyclic ring, and its meaning includes any possible connection mode shown in formula (f-1) to formula (f-10).

[0072]

[0073] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formula (X'-1) to formula (X'-4).

[0074]

[0075] In some embodiments of the present application, R 5 , R 6 , R 7 and R 8 There is only one structure selected from the structure shown in formula 1-1.

[0076] In some embodiments of the present application, the organic compound has a structure shown in Formula 1-A:

[0077]

[0078] In some embodiments of the present application, Ar 1 It is 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.

[0079] Optionally, Ar 1 is selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0080] Optionally, Ar 1 The substituents in are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms.

[0081] Optionally, in Ar 1 Any two adjacent substituents can form a cyclohexane Cyclopentane Benzene ring, naphthalene ring or fluorene ring

[0082] Optionally, Ar 1 Any two adjacent substituents in the group form a saturated or unsaturated ring having 5 to 13 carbon atoms.

[0083] Specifically, Ar 1Specific examples of substituents in include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenyl.

[0084] In other embodiments of the present application, Ar 1 is 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 dibenzothienyl, and substituted or unsubstituted spirobifluorenyl.

[0085] Optionally, Ar 1 The substituents in are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenyl.

[0086] In some embodiments of the present application, Ar 1 is selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the following groups:

[0087]

[0088] 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, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0089] Optionally, Ar 1 Selected from the group consisting of:

[0090]

[0091] In some specific embodiments, Ar 1 Selected from the following groups:

[0092]

[0093] In some embodiments of the present application, n 1 、n 2 、n 3 and n 4 Both are 0.

[0094] In some embodiments of the present application, each R 1 , R 2 , R 3 and R 4are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0095] In some embodiments of the present application, n 9 and n 10 Both are 0.

[0096] In some embodiments of the present application, each R 9 and R 10 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0097] In some embodiments of the present application, X is selected from C(R 11 R 12 ), and R 11 and R 12 All are methyl.

[0098] In some embodiments of the present application, X is selected from O or S.

[0099] In some embodiments of the present application, Ar 2 Selected from the group consisting of:

[0100]

[0101] Each R 9 and R 10 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0102] In some embodiments of the present application, Ar 2 Selected from the group consisting of:

[0103]

[0104] In some specific embodiments of the present application, Ar 2 Selected from the group consisting of:

[0105]

[0106] In some embodiments of the present application, L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 20 carbon atoms.

[0107] Optionally, L, L 1 and L 2the same or different, 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.

[0108] Optionally, L, L 1 and L 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0109] Optionally, L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0110] Optionally, L 1 and L 2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

[0111] In some embodiments of the present application, L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group.

[0112] Optionally, L, L 1 and L 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl or phenyl.

[0113] Optionally, L is 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 fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.

[0114] Optionally, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene.

[0115] When L is not a single bond, that is, when the nitrogen-containing group of the organic compound of the present application is connected to the aromatic amine through an aromatic group or a heteroaromatic group, the material has a deeper HOMO energy level, which is beneficial to the injection and transmission of holes.

[0116] Optionally, L 1 is 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.

[0117] Optionally, L 2 is selected from a single bond, and substituted or unsubstituted phenylene.

[0118] In some embodiments of the present application, L, L 1 and L 2 are the same or different, each independently selected from a single bond, a substituted or unsubstituted group Q; wherein the unsubstituted group Q is selected from the group consisting of the following groups:

[0119]

[0120] The substituted group Q has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.

[0121] Optionally, L, L 1 and L 2 The same or different, each independently selected from a single bond or the group consisting of the following groups:

[0122]

[0123] Further optionally, L is selected from a single bond or the following groups:

[0124]

[0125] Further optionally, L 1 Independently selected from a single bond or the following groups:

[0126]

[0127] Further optionally, L 2 Select from single bond or

[0128] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] 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.

[0144] Optionally, the electronic component is an organic electroluminescent device.

[0145] In some embodiments of the present application, the electronic component is an organic electroluminescent device. Figure 1 As 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.

[0146] In some specific embodiments of the present application, the organic electroluminescent device is a blue organic electroluminescent device.

[0147] Optionally, the anode 100 includes the following anode materials, which are optionally materials with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole and polyaniline, but not limited thereto. A transparent electrode including indium tin oxide (ITO) as an anode is preferred.

[0148] Optionally, the hole transport layer 320 includes one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and those skilled in the art can select them according to the prior art.

[0149] In one specific embodiment, the hole transport layer 320 is an organic compound as described herein.

[0150] Optionally, the electron blocking layer 330 includes one or more electron blocking materials, and the electron blocking material can be selected from carbazole polymers or other types of compounds, which are not specifically limited in the present application. For example, the material of the electron blocking layer 330 is selected from the group consisting of the following compounds:

[0151]

[0152] In some embodiments of the present application, the electron blocking layer 330 is HT-16.

[0153] Optionally, a hole injection layer 310 may be 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 made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example;

[0154]

[0155] In some embodiments of the present application, the hole injection layer 310 is composed of F4-TCNQ.

[0156] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a main material and a doping material. Optionally, the organic light-emitting layer 340 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 340 and electrons injected into the organic light-emitting layer 340 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.

[0157] The main material of the organic light-emitting layer 340 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special limitation thereto.

[0158] In some embodiments of the present application, the main material of the organic light-emitting layer 340 is BH-01.

[0159] The guest material of the organic light-emitting layer 340 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. For example, specific examples of the blue light fluorescent dopant include but are not limited to:

[0160]

[0161]

[0162] In some specific embodiments of the present application, the guest material of the organic light-emitting layer 340 is BD-01.

[0163] The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions. The materials of the electron transport layer 350 include but are not limited to the following compounds:

[0164]

[0165] In some specific embodiments of the present application, the electron transport layer 350 is composed of BCP and LiQ.

[0166] In the present application, cathode 200 may include cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.

[0167] Optionally, an electron injection layer 360 may be 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 a complex of an alkali metal and an organic substance. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0168] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0169] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The 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.

[0170] 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.

[0171] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0172] Synthesis Example

[0173] 1. Synthesis of aX

[0174] Synthesis of a1

[0175]

[0176] Indolecarbazole (50.0 g; 195.1 mmol), 2,4-dibromo-1-fluorobenzene (41.3 g; 162.6 mmol), cesium carbonate (105.9 g; 325.1 mmol), N,N-dimethylformamide (500 mL) were added to a round-bottom flask, stirred and heated to 150°C-153°C under nitrogen protection, and reacted for 12 hours. The reaction mixture was cooled to room temperature, washed with water, the organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as an eluent, and then recrystallized and purified using toluene / n-heptane to obtain a white solid intermediate a1 (38.6 g; yield 58%).

[0177] Referring to the synthesis method of intermediate a1, reactant A in Table 1 was used to replace 2,4-dibromo-1-fluorobenzene to synthesize intermediate a2 shown in Table 1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0178] Table 1

[0179]

[0180] 2. Synthesis of intermediate a1-X

[0181] Synthesis of intermediate a1-1

[0182]

[0183] The intermediate a1 (25 g; 61.1 mmol), 4-chlorophenylboronic acid (11.5 g; 73.3 mmol), tetrakis(triphenylphosphine)palladium (0.7 g; 0.6 mmol), potassium carbonate (16.9 g; 122.2 mmol), tetrabutylammonium bromide (2.0 g; 6.1 mmol), toluene (200 mL), ethanol (100 mL) and deionized water (50 mL) were added to a round-bottom flask, stirred and heated to 75°C-80°C under nitrogen protection, and reacted for 12 hours. The reaction mixture was cooled to room temperature, washed with water, the organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as an eluent, and then purified by recrystallization using toluene / n-heptane to obtain a white solid intermediate a1-1 (20.2 g; yield 75%).

[0184] Referring to the synthesis method of intermediate a1-1, the reactant B in Table 2 was used to replace 4-chlorophenylboronic acid to synthesize the intermediates shown in Table 2. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0185] Table 2

[0186]

[0187]

[0188]

[0189] Referring to the synthesis method of intermediate a1-1, intermediate a2 was used to replace a1, and reactant C in Table 3 was used to replace 4-chlorophenylboronic acid to synthesize the intermediates shown in Table 3. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0190] Table 3

[0191]

[0192] 3. Synthesis of compounds

[0193] Synthesis of compound 1

[0194]

[0195] The intermediate a1 (10 g; 24.4 mmol), N-phenyl-3-dibenzofuran-2-amine (5.8 g; 22.2 mmol), tri(dibenzylideneacetone)dipalladium (0.2 g; 0.2 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (0.2 g; 0.4 mmol), sodium tert-butoxide (3.2 g; 33.3 mmol) and toluene (200 mL) were added to a round-bottom flask protected by nitrogen, heated to 105° C. to 110° C. under stirring, and reacted for 16 hours; the reaction solution was cooled to room temperature, washed with water and then the organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using dichloromethane / n-heptane, and then purified by recrystallization using toluene / n-heptane to obtain a white solid compound 1 (9.8 g; yield 75%).

[0196] Synthesis example 2-13:

[0197] Referring to the synthesis method of compound 1, reactant D in Table 4 was used to replace N-phenyl-3-dibenzofuran-2-amine to synthesize the compounds in Table 4. The main raw materials used, the synthesized compounds and the final step yields are shown in Table 4.

[0198] Table 4

[0199]

[0200]

[0201] Synthesis examples 14 to 39:

[0202] Referring to the synthesis method of compound 1, reactant E in Table 5 was used to replace intermediate a1, and reactant F was used to replace N-phenyl-3-dibenzofuran-2-amine to synthesize the compounds in Table 5. The main raw materials used, the synthesized compounds and the final step yields are shown in Table 5.

[0203] Table 5

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] Compound characterization data:

[0211] The mass spectrum data of the compound are shown in Table 6 below:

[0212] Table 6

[0213] Compound 1 <![CDATA[m / z=588.2[M+H] + ]]> Compound 263 <![CDATA[m / z=756.2[M+H] + ]]> Compound 4 <![CDATA[m / z=664.2[M+H] + ]]> Compound 265 <![CDATA[m / z=766.3[M+H] + ]]> Compound 21 <![CDATA[m / z=754.2[M+H] + ]]> Compound 266 <![CDATA[m / z=796.3[M+H] + ]]> Compound 47 <![CDATA[m / z=638.2[M+H] + ]]> Compound 270 <![CDATA[m / z=816.3[M+H] + ]]> Compound 96 <![CDATA[m / z=740.3[M+H] + ]]> Compound 272 <![CDATA[m / z=740.3[M+H] + ]]> Compound 117 <![CDATA[m / z=704.3[M+H] + ]]> Compound 275 <![CDATA[m / z=832.3[M+H] + ]]> Compound 137 <![CDATA[m / z=704.2[M+H] + ]]> Compound 276 <![CDATA[m / z=756.2[M+H] + ]]> Compound 174 <![CDATA[m / z=806.3[M+H] + ]]> Compound 277 <![CDATA[m / z=790.3[M+H] + ]]> Compound 190 <![CDATA[m / z=770.2[M+H] + ]]> Compound 278 <![CDATA[m / z=842.4[M+H] + ]]> Compound 209 <![CDATA[m / z=844.3[M+H] + ]]> Compound 279 <![CDATA[m / z=766.3[M+H] + ]]> Compound 216 <![CDATA[m / z=690.3[M+H] + ]]> Compound 280 <![CDATA[m / z=806.3[M+H] + ]]> Compound 231 <![CDATA[m / z=766.3[M+H] + ]]> Compound 281 <![CDATA[m / z=816.3[M+H] + ]]> Compound 297 <![CDATA[m / z=632.2[M+H] + ]]> Compound 282 <![CDATA[m / z=830.3[M+H] + ]]> Compound 237 <![CDATA[m / z=704.3[M+H] + ]]> Compound 283 <![CDATA[m / z=796.3[M+H] + ]]> Compound 241 <![CDATA[m / z=670.3[M+H] + ]]> Compound 284 <![CDATA[m / z=872.3[M+H] + ]]> Compound 249 <![CDATA[m / z=796.3[M+H] + ]]> Compound 285 <![CDATA[m / z=830.3[M+H] + ]]> Compound 251 <![CDATA[m / z=730.2[M+H] + ]]> Compound 295 <![CDATA[m / z=669.3[M+H] + ]]> Compound 255 <![CDATA[m / z=766.3[M+H] + ]]> Compound 298 <![CDATA[m / z=720.3[M+H] + ]]> Compound 257 <![CDATA[m / z=780.3[M+H] + ]]> Compound 299 <![CDATA[m / z=705.2[M+H] + ]]> Compound 260 <![CDATA[m / z=680.2[M+H] + ]]>

[0214] The NMR data of some intermediates and compounds are shown in Table 7 below:

[0215] Table 7

[0216]

[0217]

[0218] Preparation and evaluation of organic electroluminescent devices:

[0219] The present application also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes the organic compound of the present application. The organic electroluminescent device of the present application is described in detail below by way of examples. However, the following examples are merely examples of the present application, and do not limit the present application.

[0220] Example 1: Preparation of blue organic electroluminescent device

[0221] The anode was prepared by the following process: The ITO substrate (made by Corning) was cut into a size of 40 mm × 40 mm × 0.7 mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography. 2 :N 2 Plasma surface treatment was performed to increase the work function of the anode (experimental substrate) and to remove scum.

[0222] F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer (HIL) is formed by evaporating compound 1 on the hole injection layer to form a layer with a thickness of of a hole transport layer (HTL).

[0223] HT-16 was vacuum-deposited on the hole transport layer to form a layer with a thickness of The electron blocking layer (EBL)

[0224] On the electron blocking layer, BD-01 doped with BH-01 by 1% (film thickness ratio) was co-evaporated to form a film with a thickness of organic light-emitting layer (blue light-emitting layer, B-EML).

[0225] On the organic light-emitting layer, BCP and LiQ are evaporated at a weight ratio of 1:1 to form Thick electron transport layer (ETL).

[0226] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium and silver are vacuum-deposited on the electron injection layer at a deposition rate of 1:10 to form a layer with a thickness of cathode.

[0227] In addition, a layer with a thickness of The CP-01 is used to form an organic cover layer (CPL), thereby completing the manufacture of the organic light-emitting device.

[0228] Example 2-Example 39:

[0229] The organic electroluminescent device was prepared by the same method as in Example 1, except that when preparing the hole transport layer, Compound 1 was replaced by the compounds shown in Table 8.

[0230] Comparative Example 1-Comparative Example 4:

[0231] An organic electroluminescent device was prepared by the same method as in Example 1, except that when preparing the hole transport layer, Compound 1 was replaced by Compound A, Compound B, Compound C, and Compound D, respectively.

[0232] When preparing the organic electroluminescent device, the structures of the materials used in the comparative examples and the examples are as follows:

[0233]

[0234]

[0235] The performance of the blue organic electroluminescent devices prepared in Examples 1-39 and Comparative Examples 1-4 was tested. Specifically, at 20 mA / cm 2 The photoelectric performance of the device was tested under the conditions of , and the test results are shown in Table 8.

[0236] Table 8

[0237]

[0238]

[0239] Referring to the above table, it can be seen that when the compounds of the present application are used as hole transport layer materials in Examples 1-39, compared with Comparative Examples 1-4, there are more obvious improvements in the current, voltage and life of the device, with the current efficiency being increased by at least 10.7% and the life being increased by at least 12%.

[0240] The device performance of the compounds of the present application is improved compared with Comparative Examples 1 to 4. Compared with Comparative Example 1, the organic compounds of the present application use aromatic amine groups to connect special nitrogen-containing groups and dibenzopentacyclic rings, which can greatly improve the hole mobility of the compound molecules, thereby reducing the voltage of the device and improving the luminous efficiency.

[0241] Compared with Comparative Examples 2-4, the compounds of the present application have relatively suitable energy band width and ultraviolet-visible light absorption range, and can reduce the extinction effect and improve efficiency when used as a hole transport layer.

[0242] Therefore, when the organic compound of the present application is used to prepare a blue organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be effectively improved and its life can be extended. In particular, when the nitrogen-containing group of the organic compound of the present application is connected to the aromatic amine through an aromatic group or a heteroaromatic group, the device life is improved more significantly. The reason may be that when the nitrogen-containing group of the organic compound of the present application is connected to the aromatic amine through an aromatic group or a heteroaromatic group, the material has a deeper HOMO energy level, which is conducive to the injection and transmission of holes.

[0243] Therefore, when the organic compound of the present application is used to prepare an organic electroluminescent device, the driving voltage of the device can be effectively reduced, and the efficiency and life of the device can also be improved.

[0244] Those skilled in the art will appreciate that the above-mentioned embodiments are specific examples for implementing the present application, and in actual applications, various changes may be made thereto in form and detail without departing from the spirit and scope of the present application.

Claims

1. An organic compound, It is characterized in that The organic compound has a structure as shown in Formula 1-A: Among them, each R 1 , R 2 , R 3 and R 4 Same, selected from deuterium; L is 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 fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiopheneene group; L 1 and L 2 are the same or different, each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; L, L 1 and L 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl; Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl; Ar 1 The substituents are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl; Ar 2 A group selected from the group shown in formula 1-2; X is selected from C(R 11 R 12 ), O or S; Each R 9 and R 10 Same, selected from deuterium; R 11 and R 12 Same, selected from methyl; n 1 For R 1 The number of is selected from 0, 1, 2, 3 or 4; n 2 For R 2 The number of is selected from 0, 1, 2, 3 or 4; n 3 For R 3 The number of is selected from 0, 1 or 2; n 4 For R 4 The number of is selected from 0, 1, 2, 3 or 4; n 9 For R 9 The number of is selected from 0, 1, 2 or 3; n 10 For R 10 The number is selected from 0, 1, 2, 3 or 4.

2. The organic compound according to claim 1, in, The Ar 2 Selected from the group consisting of:

3. The organic compound according to claim 1, in, The Ar 2 Selected from the group consisting of:

4. The organic compound according to claim 1, in, 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; in, The functional layer comprises the organic compound according to any one of claims 1 to 4; The electronic component is an organic electroluminescent device; The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

6. An electronic device comprising the electronic component according to claim 5.

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