Organic compounds and organic electroluminescent devices and electronic devices

Abstract

This application belongs to the field of organic light-emitting materials, specifically relating to an organic compound and organic electroluminescent devices and electronic devices using the same. The structure of the organic compound is shown in Formula 1, and the organic compound, when used in an organic electroluminescent device, can improve the performance of the device.

Description

Technical Field

[0001] This application belongs to the field of organic light-emitting materials technology, specifically providing an organic compound and an organic electroluminescent device and electronic device using the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting materials, emit light when excited by an electric current under the influence of an electric field. It is a process of converting electrical energy into light energy. Compared to inorganic light-emitting materials, OLEDs offer advantages such as active light emission, a wide optical path range, low driving voltage, high brightness, high efficiency, low energy consumption, and simple fabrication processes. Due to these advantages, organic light-emitting materials and devices have become a very popular research topic in both scientific and industrial communities.

[0003] Organic electroluminescent devices generally consist of an anode, a hole transport layer, an electroluminescent layer (serving as an energy conversion layer), an electron transport layer, and a cathode, stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the electroluminescent layer. Electrons and holes combine in the electroluminescent layer to form excitons. These excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0004] Currently, OLED display technology has been applied in smartphones, tablets, and other fields, and will further expand into large-screen applications such as televisions. However, compared with the requirements of actual product applications, the luminous efficiency, lifespan, and other performance characteristics of OLED devices still need further improvement. Research on improving the performance of OLED light-emitting devices includes: reducing the operating voltage of the devices, increasing the luminous efficiency, and extending the lifespan. To continuously improve the performance of OLED devices, innovation is needed not only in OLED device structure and manufacturing processes, but also in the continuous research and innovation of OLED optoelectronic functional materials to create functional materials for higher-performance OLEDs. Summary of the Invention

[0005] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device using the same, wherein the organic compound used in the organic electroluminescent device can improve the performance of the device.

[0006] To achieve the above objectives, the first aspect of this application provides an organic compound having a structure as shown in Formula 1:

[0007]

[0008] Where X is selected from O or S;

[0009] Ar is selected from substituted or unsubstituted aryl groups having 6-15 carbon atoms, and the substituents in Ar are each independently selected from deuterium, cyano or alkyl groups having 1-4 carbon atoms;

[0010] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms.

[0011] Ar1 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms and substituted or unsubstituted heteroaryl groups with 5-40 carbon atoms;

[0012] The substituents in L, L1, L2, and Ar1, as well as R1, R2, and R3, may be the same or different, and each is independently selected from deuterium, cyano, aryl with 6-18 carbon atoms, heteroaryl with 5-18 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, or triphenylsilyl; optionally, in Ar1, any two adjacent substituents form a 3-15 member saturated or unsaturated ring;

[0013] n1 represents the number of R1s, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, all R1s may be the same or different.

[0014] n2 represents the number of R2s, and is selected from 0, 1, 2 or 3; when n2 is greater than 1, all R2s may be the same or different.

[0015] n3 represents the number of R3s, and is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, all R3s are the same or different.

[0016] A second aspect of this application provides an organic electroluminescent device comprising the organic compound described in the first aspect of this application.

[0017] A third aspect of this application provides an electronic device, the electronic device including the organic electroluminescent device described in the second aspect of this application.

[0018] The organic compound of this application is a triarylamine structure having an N-phenylcarbazole and a dibenzofuran (thiophene) group. The simultaneous introduction of fluorine (F) and aromatic substituents onto the benzene ring of the carbazole allows the organic compound to effectively inhibit electron migration while promoting hole transport, exhibiting high hole transport efficiency. Furthermore, the compound possesses appropriate steric torque, thereby improving its thermal stability. When applied to organic electroluminescent devices, the compound can further improve the device's lifespan and luminous efficiency.

[0019] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0020] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0021] Figure 2 This is a schematic diagram of an electronic device according to one embodiment of this application.

[0022] Explanation of reference numerals in the attached figures

[0023] 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; 400, Electronic device. Detailed Implementation

[0024] The specific embodiments of this application will be described in detail below with reference to the accompanying drawings. It should be understood that the specific embodiments described herein are for illustration and explanation only and are not intended to limit this application.

[0025] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0026]

[0027] Ar is selected from substituted or unsubstituted aryl groups having 6-15 carbon atoms, and the substituents in Ar are each independently selected from deuterium, cyano or alkyl groups having 1-4 carbon atoms;

[0028] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms.

[0029] Ar1 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms and substituted or unsubstituted heteroaryl groups with 5-40 carbon atoms;

[0030] The substituents in L, L1, L2, and Ar1, as well as R1, R2, and R3, may be the same or different, and each is independently selected from deuterium, cyano, aryl with 6-18 carbon atoms, heteroaryl with 5-18 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, or triphenylsilyl; optionally, in Ar1, any two adjacent substituents form a 3-15 member saturated or unsaturated ring;

[0031] n1 represents the number of R1s, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, all R1s may be the same or different.

[0032] n2 represents the number of R2s, and is selected from 0, 1, 2 or 3; when n2 is greater than 1, all R2s may be the same or different.

[0033] n3 represents the number of R3s, and is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, all R3s are the same or different.

[0034] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. 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. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0035] In this application, the terms "optional" or "optionally" mean that the event or situation described below may, but does not have to, occur, and the description includes situations in which the event or situation occurs or does not occur. For example, "optionally, two adjacent substituents form a ring" means that the two substituents may form a ring but are not required to form a ring, which includes both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring.

[0036] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The substituents mentioned above, i.e., Rc, can be, for example, deuterium, cyano, heteroaryl, aryl, alkyl, cycloalkyl, deuterated alkyl, trialkylsilyl, etc. The "substituted" functional group can be substituted by one or more of the substituents mentioned above in Rc; when two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a spirocyclic ring with the atom; when two adjacent substituents Rc are present on a functional group, the two adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0037] In this application, the term "ring" includes saturated rings and unsaturated rings; saturated rings are cycloalkyl and heterocycloalkyl groups, while unsaturated rings include cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl groups. In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl group; fluorene is a 13-membered ring; cyclohexane is a 6-membered ring; and adamantane is a 10-membered ring.

[0038] In this application, the phrase "any two adjacent substituents form a 3-15 member saturated or unsaturated ring" refers to a saturated or unsaturated ring, where a saturated ring is, for example, cyclopentane. Cyclohexane Unsaturated rings, such as benzene rings, naphthalene rings, or fluorene rings.

[0039] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12. For example: Ar1 is... Therefore, its carbon atom number is 10; L1 is It has 12 carbon atoms.

[0040] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. It should be noted that biphenyl and fluorene are both considered aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. Base, etc.

[0041] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are substituted by groups such as deuterium, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, deuterated alkyl, cycloalkyl, triphenylsilyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and its substituents. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and its substituents is 18. Furthermore, in this application, the fluorene group can be substituted, and when it has two substituents, the two substituents can combine with each other to form a spirostructure. Specific examples of substituted fluorene groups include, but are not limited to,

[0042]

[0043] In this application, the term arylene refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0044] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6-40. For example, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40.

[0045] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing one, two, three, four, five or more heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. Among them, thienyl, furanyl, and phenanthroline are heteroaryl groups of the single aromatic ring type, while N-phenylcarbazoyl is a heteroaryl group of the polycyclic system type connected by carbon-carbon bonds. In this application, the hypoaryl group refers to the divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0046] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, deuterated alkyl, cycloalkyl, triphenylsilyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0047] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 5-40. For example, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39 or 40.

[0048] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0049] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule via two non-positional linkages that span the bicyclic ring. This can mean any of the possible connection schemes shown in equations (f-1) to (f-10):

[0050]

[0051] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0052]

[0053] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0054]

[0055] In this application, the number of carbon atoms in an alkyl group can be 1-10, specifically 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Alkyl groups can include straight-chain alkyl groups and branched-chain alkyl groups. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0056] In this application, the number of carbon atoms of the aryl group used as a substituent can be 6-18, specifically 6, 10, 12, 13, 14, 15, etc. Specific examples of aryl groups include, but are not limited to, phenyl, naphthyl, biphenyl, phenanthryl, anthracene, etc.

[0057] In this application, the number of carbon atoms of the heteroaryl group used as a substituent can be 5-18, and the specific number of carbon atoms is, for example, 5, 8, 9, 10, 12, 13, 14, 15, etc. Specific examples of heteroaryl groups include, but are not limited to, pyridyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, etc.

[0058] In this application, the number of carbon atoms in the trialkylsilyl group used as a substituent can be 3-12, such as 3, 6, 7, 8, 9, etc., and specific examples include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, triethylsilyl, etc.

[0059] In this application, the number of carbon atoms in the cycloalkyl group used as a substituent can be 3-10, for example 5, 6, 8 or 10, and specific examples include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, etc.

[0060] In this application, the number of carbon atoms in the deuterated alkyl group used as a substituent can be 1-10. For example, the deuterated alkyl group is a deuterated alkyl group with 1-4 carbon atoms. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0061] In this application, the structure of the organic compound may be as shown in Formula 1-1 or Formula 1-2:

[0062]

[0063] Optionally, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and the substituents in Ar are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl or tert-butyl.

[0064] In one embodiment, Ar is selected from the group consisting of:

[0065]

[0066] Alternatively, Ar is selected from the group consisting of:

[0067]

[0068] In this application, L, L1, and L2 can each be independently selected from single bonds, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30 carbon atoms.

[0069] In one embodiment, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12-18 carbon atoms.

[0070] Optionally, L and L2 are each independently selected from single-bonded substituted or unsubstituted aryl groups with 6-15 carbon atoms.

[0071] Optionally, L1 is selected from single bonds, substituted or unsubstituted aryl groups with 6-15 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12-18 carbon atoms.

[0072] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted carbazolyl.

[0073] In one embodiment, the substituents in L, L1 and L2 are each independently selected from deuterium, cyano, aryl with 6-12 carbon atoms, heteroaryl with 5-12 carbon atoms, trialkylsilyl with 3-7 carbon atoms or alkyl with 1-4 carbon atoms.

[0074] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazoyl.

[0075] In one embodiment, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded, substituted, or unsubstituted groups Z, wherein the unsubstituted group Z is selected from the group consisting of:

[0076]

[0077] The substituents in the substituted group Z are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl or naphthyl. When the number of substituents is greater than 1, the substituents may be the same or different.

[0078] Optionally, L, L1, and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0079]

[0080] In one specific embodiment, L and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0081]

[0082] In one specific embodiment, L1 is selected from the group consisting of single bonds or the following groups:

[0083]

[0084] Optionally, Ar1 is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0085] In one embodiment, Ar1 is selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12-25 carbon atoms.

[0086] In some embodiments, Ar1 is 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 anthraquinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoleyl.

[0087] In one embodiment, the substituents in Ar1 are each independently selected from deuterium, cyano, aryl with 6-12 carbon atoms, heteroaryl with 5-12 carbon atoms, trialkylsilyl with 3-7 carbon atoms, alkyl with 1-4 carbon atoms, deuterated alkyl with 1-4 carbon atoms, or cycloalkyl with 5-10 carbon atoms; optionally, in Ar1, any two adjacent substituents form a 5-15 saturated or unsaturated ring.

[0088] Optionally, the substituents in Ar1 are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, trimethylsilyl, trideuterated methyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl; optionally, any two adjacent substituents form a benzene ring, cyclopentane, cyclohexane, or fluorene ring.

[0089] In one embodiment, Ar1 is selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of:

[0090]

[0091] The substituents in the substituted group W are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl. When the number of substituents is greater than 1, the substituents may be the same or different.

[0092] Alternatively, Ar1 is selected from the group consisting of:

[0093]

[0094] Further, optionally, Ar1 is selected from the group consisting of:

[0095]

[0096]

[0097] In one implementation, Selected from the group consisting of the following groups:

[0098]

[0099] In one embodiment, R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, cyano, aryl with 6-12 carbon atoms, trialkylsilyl with 3-7 carbon atoms, alkyl with 1-4 carbon atoms, or deuterated alkyl with 1-4 carbon atoms.

[0100] Optionally, R1, R2, and R3 may be the same or different, and each may be independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, or naphthyl.

[0101] Optionally, the organic compound is selected from the group consisting of:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] This application does not specifically limit the synthetic methods of the provided organic compounds. Those skilled in the art can determine suitable synthetic methods based on the organic compounds described in the Synthesis Examples section of this application, combined with the preparation methods provided. In other words, the Synthesis Examples section of this application exemplarily provides methods for preparing organic compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all the organic compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic compounds are not detailed here, and should not be construed as limiting this application.

[0116] A second aspect of this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises the organic compound described in the first aspect of this application. The organic compound provided in this application can be used to form at least one organic film layer in the functional layer to improve characteristics such as the lifespan of electronic components.

[0117] Optionally, the functional layer includes a hole transport layer, which contains the organic compounds of this application.

[0118] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer (also referred to as an "electron blocking layer" or "light-emitting auxiliary 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.

[0119] According to a specific implementation method, such as Figure 1 As shown, the organic electroluminescent device includes an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330 serving as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are stacked sequentially. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0120] Optionally, the anode 100 comprises an anode material, preferably one with a high 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 alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0121] Optionally, the first hole transport layer 321 may comprise one or more hole transport materials. These materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any specific limitations on this. Specific examples of the hole transport materials include, but are not limited to, […].

[0122]

[0123] In one specific embodiment, the material of the first hole transport layer 321 is HT-4.

[0124] Optionally, the material of the second hole transport layer 322 is selected from the organic compounds of this application.

[0125] In this application, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can include a host material and a guest material. Preferably, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. 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.

[0126] The host material of the organic light-emitting layer 330 can be a metal chelating compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. Specific examples of the host material include, but are not limited to, the following compounds:

[0127]

[0128] In one specific embodiment, the main material is BH-2.

[0129] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and this application does not impose any special limitations on this. For example, the guest material is selected from at least one of the following compounds:

[0130]

[0131] In one specific embodiment, the object material is BD-3.

[0132] In this application, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport material is selected from, but is not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. For example, the electron transport layer material is selected from the group consisting of LiQ and the following compounds:

[0133]

[0134] In one specific embodiment, the electron transport layer 340 is composed of LiQ and ET-2.

[0135] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. 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, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode comprising magnesium and silver is included as the cathode.

[0136] Optionally, such as Figure 1 As shown, a hole injection layer 310 is further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the hole injection layer 310 is selected from one or more of the following compounds:

[0137]

[0138]

[0139] In one specific embodiment, the hole injection layer 310 is made of F4-TCNQ material.

[0140] Optionally, such as Figure 1As shown, an electron injection layer 350 is further disposed 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 complexes of alkali metals and organic materials. For example, the electron injection layer 350 contains LiQ or Yb.

[0141] A third aspect of this application provides an electronic device comprising the organic electroluminescent device described in the second aspect of this application.

[0142] According to one implementation method, such as Figure 2 As shown, the electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. 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, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0143] The present application is further illustrated by the following examples, but the present application is not limited thereto. Compounds synthesized using methods not mentioned in this application are all commercially available raw material products.

[0144] 1. Synthesis of intermediate IMAX

[0145] Let's take IMA1 as an example to illustrate IMAX compositing.

[0146]

[0147] (1) 4-Biphenylboronic acid (19.8 g, 100.00 mmol), 2-bromo-4-fluoronitrobenzene (22.00 g, 100.00 mmol), tetratriphenylphosphine palladium (2.31 g, 2.00 mmol), tetrabutylammonium bromide (3.22 g, 10.00 mmol) and potassium carbonate (27.6 g, 200 mmol) were added to a mixed solvent of toluene (80 mL), ethanol (40 mL) and water (20 mL). The mixture was heated to 72 °C under nitrogen protection and stirred for 15 h. The mixture was then cooled to room temperature. The resulting reaction solution was washed with water and dried with magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization with toluene (1 g crude product: 3 mL toluene) to obtain a pale yellow intermediate IMA1-1 (21.09 g, yield 72%).

[0148]

[0149] (2) IMA1-1 (14.66 g, 50.00 mmol), triphenylphosphine (39.34 g, 150.00 mmol) and o-dichlorobenzene (150 mL) were added to a 250 mL three-necked flask, heated to 160 °C under nitrogen protection, and stirred for 18 h. Then cooled to room temperature, the resulting reaction solution was washed with water, extracted with toluene, dried with magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization with n-heptane and dichloromethane to obtain intermediate IMA1 (9.93 g, yield 76%).

[0150] Other IMAXs were synthesized using the same method as IMA1, except that 4-biphenylboronic acid was replaced by raw material 1 and 2-bromo-4-fluoronitrobenzene was replaced by raw material 2. The main raw materials used, the synthesized IMAXs and their total yields are shown in Table 1.

[0151] Table 1

[0152]

[0153]

[0154]

[0155] 2. Synthesis of intermediate IM BX

[0156] The synthesis of IMBX is illustrated using IMB1 as an example.

[0157]

[0158] IMA1 (6.53 g, 25.00 mmol), 3-chloro-1-bromobenzene (4.78 g, 25.00 mmol), tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.24 g, 0.50 mmol), and sodium tert-butoxide (4.8 g, 50.0 mmol) were added to toluene (50 mL). The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, the resulting reaction solution was washed with water, dried with magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure to obtain the crude product. The crude product was purified by recrystallization from toluene (1 g crude product: 6 mL toluene) to give the white intermediate IM B1 (4.83 g, yield 52.0%).

[0159] Other IM BX were synthesized using the same method as IM B1, except that raw material 3 was used instead of IMA1 and raw material 4 was used instead of 3-chloro-1-bromobenzene. The synthesized IM BX and their yields are shown in Table 2.

[0160] Table 2

[0161]

[0162]

[0163]

[0164] Synthesis example 1

[0165]

[0166] IM B1 (7.43 g, 20.00 mmol), SubA (8.23 g, 20.00 mmol), tris(dibenzylacetone)dipalladium (0.18 g, 0.20 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.40 mmol), and sodium tert-butoxide (3.85 g, 40.00 mmol) were added to toluene (100 mL). The mixture was heated to 105 °C under nitrogen protection and stirred for 4 h. After cooling to room temperature, the resulting reaction solution was washed with water, dried with magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization from toluene (1 g crude product: 12 mL toluene) to give a white solid, compound 1 (10.91 g, yield 73%), mass spectrometry: m / z = 747.3 [M+H]. + .

[0167] Synthesis example 2-37

[0168] Other compounds were synthesized using the same method as compound 1, except that raw material 5 was used instead of IM B1 and raw material 6 was used instead of SubA. The main raw materials used, the synthesized compounds, their yields, and mass spectrometry results are shown in Table 3.

[0169] Table 3

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] NMR data of compound 216 (1H-NMR, 400MHz, CD2Cl2) δppm: 8.22 (d, 1H), 7.97 (d, 1H), 7.93 (d, 1H), 7.76–7.72 (m, 2H), 7.62 (d, 2H), 7.55–7.51 (m, 4H), 7.50–7.46 (m, 3H), 7.45–7.31 (m, 8H), 7.23 (d, 1H), 7.21 (s, 1H), 7.10 (s, 1H), 7.03 (d, 1H), 6.98 (d, 1H), 6.92 (d, 1H), 6.82 (s, 1H), 6.72 (d, 2H).

[0178] Fabrication and Evaluation of Organic Electroluminescent Devices

[0179] Example 1: Blue Organic Electroluminescent Device

[0180] Organic electroluminescent devices are fabricated using the following process: [The following steps are described, and the following steps are performed with thicknesses sequentially as follows:] The ITO / Ag / ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness). The substrate was then prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The substrate was then surface-treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The substrate surface was then cleaned with organic solvents to remove impurities and oil stains.

[0181] F4-TCNQ was vacuum-deposited on the experimental substrate (anode) to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and HT-4 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. The first hole transport layer (HTL-1).

[0182] Compound 1 is vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The second hole transport layer (HTL-2).

[0183] On the second hole transport layer, BH-2 is used as the main body, and BD-3 is simultaneously doped and deposited at a film thickness ratio of 100:3 to form a layer with a thickness of [missing information]. Organic light-emitting layer (EML).

[0184] On the organic light-emitting layer, ET-2 and LiQ were co-deposited at a 1:1 film thickness ratio to form a film with a thickness of [missing information]. An electron transport layer (ETL) is formed, and then Yb is deposited on the electron transport layer to form a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0185] Furthermore, CP-1 is deposited on the aforementioned cathode to form a thickness of [missing information]. The organic capping layer (CPL) is used to complete the fabrication of organic electroluminescent devices.

[0186] Example 2-37

[0187] The organic electroluminescent device was fabricated using the same method as in Example 1, except that when forming the second hole transport layer, compound 1 was replaced with the other compounds shown in Table 4 ("HTL-2" column).

[0188] Comparative Examples 1-3

[0189] Except that when forming the second hole transport layer, compound 1 was replaced with compound A, compound B and compound C respectively, the organic electroluminescent device was fabricated using the same method as in Example 1.

[0190] The structures of the main materials used in the above embodiments and comparative examples are shown below.

[0191]

[0192]

[0193] The performance of the organic electroluminescent devices prepared in the above embodiments and comparative examples was analyzed. Specifically, at 10 mA / cm², the performance was... 2 The IVL performance (voltage, color coordinates, and efficiency) of the device was analyzed at a current density of 20 mA / cm². 2 The T95 lifetime of the device was analyzed at the specified current density. The results are shown in Table 4.

[0194] Table 4

[0195]

[0196]

[0197] Based on the results in Table 4, comparing Examples 1-37 with Comparative Examples 1-3, under the condition of comparable color coordinates, the organic electroluminescent devices prepared in Examples 1-37 using the organic compound of this application as the second hole transport layer (i.e., electron blocking layer) showed at least a 12.5% ​​increase in current efficiency and at least a 10.7% increase in T95 lifetime while maintaining a low operating voltage. It is evident that applying the compound of this application as the second hole transport layer to organic electroluminescent devices can further improve the luminous efficiency and lifespan of the device while maintaining a low operating voltage.

[0198] The preferred embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application. Furthermore, various different embodiments of this application can be arbitrarily combined, as long as they do not violate the spirit of this disclosure, they should also be regarded as the content disclosed in this application.

Claims

1. An organic compound, wherein, The organic compound is selected from the group consisting of the following compounds: 。 2. An organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, characterized in that, The functional layer comprises the organic compound of claim 1.

3. The organic electroluminescent device according to claim 2, wherein The functional layer includes a hole transport layer, which contains the organic compound.

4. The organic electroluminescent device according to claim 3, wherein 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.

5. An electronic device comprising the organic electroluminescent device according to any one of claims 2 to 4.

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