Organic materials, compositions, organic electroluminescent devices, and electronic devices

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to an organic material, a composition, an organic electroluminescent device and an electronic device. The organic material has a structure as shown in formula 1. When the organic material is used in an organic electroluminescent device, the performance of the organic electroluminescent device can be significantly improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and more particularly to an organic material, a composition comprising the same, and organic electroluminescent devices and electronic devices. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide, such as organic light-emitting diodes (OLEDs). These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes a hole transport layer, a light-emitting modulation layer, an organic light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Taking an organic light-emitting diode (OLED) device as an example, it generally includes an anode, a hole transport layer, a light-emitting modulation layer, an organic light-emitting layer, an electron transport layer, and a cathode, which are 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 the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. Electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light.

[0004] Existing technologies have disclosed organic light-emitting layer materials that can be fabricated in organic electroluminescent devices. However, it remains necessary to continue developing new materials to further improve the performance of electronic components. 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 material, a composition comprising the organic material, an organic electroluminescent device and an electronic device, wherein the organic material used in the organic electroluminescent device can improve the performance of the device.

[0006] A first aspect of this application provides an organic material having a structure as shown in Formula 1:

[0007]

[0008] Where D represents deuterium; t represents the number of D, selected from 0, 1, 2, 3, 4 or 5; t is selected from 0, 1 or 2.

[0009] L is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0010] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0011] L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0012] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl groups with 6 to 30 carbon atoms respectively.

[0013] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, or alkoxy with 1 to 10 carbon atoms;

[0014] Each R1, each R2, and each R3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0015] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0016] n is the number of R2s, selected from 0, 1, 2, 3, 4 or 5. When n is greater than 1, any two R2s are the same or different.

[0017] m is the number of R3s, selected from 0, 1, 2, 3, 4 or 5. When m is greater than 1, any two R3s are the same or different.

[0018] A second aspect of this application provides a composition comprising the organic material (first compound) disclosed in the first aspect of this application and a second compound having the structure shown in Formula 2.

[0019] A third aspect of this application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the organic material disclosed in the first aspect of this application or the composition disclosed in the second aspect of this application.

[0020] The fourth aspect of this application provides an electronic device including the organic electroluminescent device disclosed in the third aspect of this application.

[0021] This application provides an organic material with a core structure in which carbazole and triazine are ortho-linked to a phenylene group. Both the para- and ortho-positions of the carbazole have phenyl substituents, and the triazine contains a specific aromatic group. This linkage enhances the compound's electronic properties, thereby improving electron-hole recombination and luminescence efficiency. Furthermore, the organic material contains carbazole and triazine ortho-linked to a phenylene group, with the carbazole ortho-linked to a phenyl group. This linkage increases the steric hindrance of the compound, resulting in exceptionally high energy transfer efficiency for phosphorescent dopants, further improving efficiency. The para-linked phenyl group on the carbazole group contributes to improved compound stability. The presence of a triazine group with specific aromatic substitutions in the organic material increases the compound's electron mobility, thus enhancing its luminescence efficiency. Therefore, using this organic material as the host material for organic electroluminescent devices can significantly improve the device's luminescence efficiency and lifetime.

[0022] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0023] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0024] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0025] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0026] Figure Labels

[0027] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0028] 320, Hole transport layer; 330, Luminescent adjustment layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0029] 360°, Electron Injection Layer 400°, First Electronic Device Detailed Implementation

[0030] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments 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, numerous specific details are provided to give a full understanding of embodiments of this application.

[0031] A first aspect of this application provides an organic material having a structure as shown in Formula 1:

[0032]

[0033] Where D represents deuterium; t represents the number of D, selected from 0, 1 or 2;

[0034] L is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0035] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0036] L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0037] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl groups with 6 to 30 carbon atoms respectively.

[0038] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, or alkoxy with 1 to 10 carbon atoms;

[0039] Each R1, each R2, and each R3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0040] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0041] n is the number of R2s, selected from 0, 1, 2, 3, 4 or 5. When n is greater than 1, any two R2s are the same or different.

[0042] m is the number of R3s, selected from 0, 1, 2, 3, 4 or 5. When m is greater than 1, any two R3s are the same or different.

[0043] In some embodiments of this application, the organic material has the structure described in Formula 1-A:

[0044]

[0045] Where D represents deuterium;

[0046] t, n, and m represent the number of D, where n and m are the same or different, and are independently selected from 0, 1, 2, 3, 4, or 5 respectively; t is selected from 0, 1, or 2.

[0047] L is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0048] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, and deuterated aryl with 6 to 20 carbon atoms.

[0049] L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0050] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted dibenzothiophene group with 6 to 30 carbon atoms respectively;

[0051] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, or alkoxy with 1 to 10 carbon atoms;

[0052] Each R1 may be the same or different, and is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0053] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0054] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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 context, each q is independently 0, 1, 2, or 3, and each R” is independently selected from hydrogen, deuterium, fluorine, and 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, and the options of each R” do not affect each other.

[0055] 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 aforementioned substituents, i.e., Rc, can be, for example, deuterium, cyano, halogen, alkyl, aryl, heteroaryl, deuterated aryl, haloaryl, cycloalkyl, alkoxy, alkylthio, etc. The number of substituents can be one or more.

[0056] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0057] 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 a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0058] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group 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. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0059] In this application, terphenyl includes

[0060] In this application, the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0061] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0062] In this application, aryl groups that serve as substituents for L, L1, L2, L4, L5, Ar1, Ar2, Ar4, and Ar5 are, for example, but not limited to, phenyl groups.

[0063] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 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 linked by carbon-carbon bonds, 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.

[0064] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 12 to 18 carbon atoms.

[0065] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, deuterated aryl groups, and haloaryl groups. 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.

[0066] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0067] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0068] In this application, deuterated aryl refers to an aryl group containing at least one deuterated substituent. Specific embodiments of deuterated aryl include, but are not limited to, pentadeuterated phenyl, pentadeuterated biphenyl, and nonadeuterated biphenyl.

[0069] In this application, deuterated alkyl means an alkyl group containing at least one deuterated substituted group, and specific examples of deuterated alkyl include, but are not limited to, trideuterated methyl.

[0070] In this application, specific examples of alkoxy groups include, but are not limited to, methoxy groups.

[0071] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0072] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can be connected to any position in the ring system that the linker penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0073]

[0074]

[0075] 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.

[0076]

[0077] In some embodiments of this application, L, L1, and L2 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups with a single bond and 6 to 12 carbon atoms. For example, L, L1, and L2 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups with a single bond and 6, 7, 8, 9, 10, 11, or 12 carbon atoms.

[0078] Optionally, the substituents in L, L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, phenyl groups or pentadeuterated phenyl groups.

[0079] In some embodiments of this application, L, L1, and L2 may be the same or different, and are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0080] Optionally, the substituents in L, L1, and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, or pentadeuterated phenyl.

[0081] In some embodiments of this application, L, L1, and L2 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of:

[0082] Specifically, L, L1, and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or groups consisting of the following:

[0083]

[0084] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted carbazole groups having 6 to 20 carbon atoms. For example, when Ar1 or Ar2 is selected from aryl groups, Ar1 and Ar2 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

[0085] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, alkoxy with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 6 to 12 carbon atoms.

[0086] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl.

[0087] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, methoxy, phenyl, naphthyl or pentadeuterated phenyl.

[0088] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of:

[0089]

[0090] Specifically, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0091]

[0092]

[0093] In some embodiments of this application, in formula 1 They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0094]

[0095] Specifically, in Equation 1 They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0096]

[0097]

[0098] In some embodiments of this application, in formula 1 Selected from the group consisting of the following groups:

[0099]

[0100]

[0101] Specifically, in Equation 1 Selected from the group consisting of the following groups:

[0102]

[0103]

[0104] In some embodiments of this application, each R1, each R2 and each R3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, aryl groups with 1 to 12 carbon atoms, and deuterated aryl groups with 6 to 12 carbon atoms.

[0105] Optionally, each R1, each R2, and each R3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, naphthyl, pentadeuterated phenyl, heptadeuterated naphthyl, tetradeuterated biphenyl, pentadeuterated biphenyl, and nonadeuterated biphenyl.

[0106] In some embodiments of this application, each R1, each R2, and each R3 may be the same or different, and are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or the following groups:

[0107]

[0108] Specifically, each of R1, R2, and R3 may be the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or the following groups:

[0109]

[0110] In some embodiments of this application, the organic material is selected from the compounds described in claim 9.

[0111] A second aspect of this application provides a composition comprising a first compound and a second compound;

[0112] The first compound has the structure shown in Formula 1, and the second compound is selected from the structure shown in Formula 2:

[0113]

[0114] Among them, each R4, each R5 and each R6 may be the same or different, and are independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, halogenated aryl with 6 to 20 carbon atoms or heteroaryl with 3 to 20 carbon atoms;

[0115] n4 is the number of R4s, selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different.

[0116] n5 is the number of R5s, which can be selected from 0, 1 or 2. When n5 is greater than 1, any two R5s are the same or different.

[0117] n6 is the number of R6, selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6 are the same or different.

[0118] L4 and L5 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0119] Ar4 and Ar5 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0120] The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and are independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, or cycloalkyl groups with 3 to 10 carbon atoms.

[0121] In some embodiments of this application, the second compound is selected from the structure shown in Formula 2-1:

[0122]

[0123] In Equation 2-1, L4, L5, Ar4, Ar5, R4, R5, R6, n4, n5, and n6 are as defined in Equation 2.

[0124] In some embodiments of this application, in the second compound shown in Formula 2, L4 and L5 may be the same or different, and are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. For example, L4 and L5 may be the same or different, and are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0125] Optionally, the substituents in L4 and L5 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

[0126] In some substantive examination methods of this application, in the second compound shown in Formula 2, L4 and L5 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene.

[0127] Optionally, the substituents in L4 and L5 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0128] In some embodiments of this application, in the second compound shown in Formula 2, L4 and L5 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of:

[0129]

[0130] Specifically, L4 and L5 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of the following:

[0131]

[0132] In some embodiments of this application, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 24 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms. For example, Ar4 and Ar5 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 10, 20, 21, 22, 23 or 24 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.

[0133] Optionally, the substituents in Ar4 and Ar5 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, naphthyl groups, or pentadeuterated phenyl groups.

[0134] In some other embodiments of this application, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0135] Optionally, the substituents in Ar4 and Ar5 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

[0136] In some embodiments of this application, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and are each independently selected from the group consisting of:

[0137]

[0138] Specifically, Ar4 and Ar5 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0139]

[0140]

[0141] In some embodiments of this application, the second compound shown in Formula 2 contains They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0142]

[0143] Specifically, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0144]

[0145]

[0146] In some embodiments of this application, in the second compound shown in Formula 2, each of R4, each of R5 and each of R6 may be the same or different, and each is independently selected from deuterium, phenyl or pentadeuterated phenyl.

[0147] In some embodiments of this application, in the second compound shown in Formula 2, n4 and n6 may be the same or different, and are independently selected from 0 or 4, respectively, and n5 is selected from 0 or 2.

[0148] In some specific embodiments of this application, n4, n5 and n6 in the second compound shown in Formula 2 are all 0.

[0149] In some specific embodiments of this application, in the second compound shown in Formula 2, n4 and n6 are both 4, and n5 is 2.

[0150] In some embodiments of this application, the second compound represented by Formula 2 is selected from the compounds represented as claimed in claim 15.

[0151] In some embodiments of this application, the first compound and the second compound in the composition are vapor-deposited, and the vapor deposition rate ratio (%) of the first compound and the second compound can be 1:99, 20:80, 30:70, 40:60, 45:55, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0152] In some preferred embodiments of this application, the vapor deposition rates of the first compound (compound of formula 1) and the second compound (compound of formula 2) are respectively 30:70, 40:60, 45:55, 50:50, 55:45, 60:40, and 70:30.

[0153] In other embodiments of this application, the mass ratio of the first compound to the second compound in the composition is 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 30:70 to 70:30, and even more preferably 40:60 to 60:40.

[0154] In some preferred embodiments of this application, the mass ratio of the first compound (compound of formula 1) and the second compound (compound of formula 2) in the composition is 30:70 to 70:30.

[0155] In some embodiments of this application, the host material and the guest material can be deposited together by a multi-source evaporation process, so that the host material and the guest material are uniformly dispersed in the organic light-emitting layer. The doping ratio can be adjusted by controlling the evaporation rate of the host material and the guest material during the evaporation process, or by controlling the ratio of the evaporation rate of the host material and the guest material.

[0156] Optionally, the organic light-emitting layer can be deposited using a multi-source co-evaporation method to form an organic light-emitting layer comprising a host material and a guest material. The doping ratio can be controlled by adjusting the evaporation rate of the host material and the guest material during the evaporation process, or by adjusting the film thickness ratio of the host material and the guest material.

[0157] To form each layer constituting the organic electroluminescent device of this application, dry film formation methods such as vacuum deposition, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0158] Furthermore, the first and second compounds can be film-formed using the methods listed above, typically via co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective individual crucible sources and an electric current is simultaneously applied to multiple chambers to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation and an electric current is applied to a chamber to evaporate the materials.

[0159] A third aspect of this application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the organic material disclosed in the first aspect of this application or the composition disclosed in the second aspect of this application.

[0160] In one embodiment of this application, the organic electroluminescent device is a phosphorescent device.

[0161] In one specific embodiment of this application, the organic electroluminescent device is a green phosphorescent organic electroluminescent device.

[0162] In some embodiments of this application, the organic electroluminescent device sequentially includes an anode (ITO substrate), a hole transport layer, a light-emitting modulator, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic capping layer.

[0163] In one specific embodiment of this application, such as Figure 1 As shown, the organic electroluminescent device of this application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer. The functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a light emission adjustment layer 330, an organic light emission layer 340, an electron transport layer 350, and an electron injection layer 360.

[0164] 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.

[0165] Optionally, the hole transport layer 320 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any specific limitations on these materials. For example, in some embodiments of this application, the hole transport layer 320 is composed of HT-1.

[0166] Optionally, the light-emitting adjustment layer 330 (also referred to as a hole adjustment layer, electron blocking layer, hole auxiliary layer, hole buffer layer, light-emitting auxiliary layer, or second hole transport layer) may include one or more hole transport materials. The hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any special limitations on this. For example, in some embodiments of this application, the light-emitting adjustment layer 330 is composed of HT-2.

[0167] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 340 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 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.

[0168] The guest material of the organic light-emitting layer 340 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials, and this application does not impose any special restrictions on this.

[0169] In some embodiments of this application, the organic electroluminescent device is a green organic electroluminescent device, which includes an organic light-emitting layer, and the organic light-emitting layer includes the organic material of this application, the second compound shown in Formula 2, and the guest material GD-1.

[0170] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not make any special limitations in this regard. For example, in some embodiments of this application, the electron transport layer 350 can be composed of ET-1 and LiQ.

[0171] Optionally, the cathode 200 comprises a cathode material having a small work function that 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 silver and magnesium is included as the cathode.

[0172] 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 selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. In some embodiments of this application, the hole injection layer 310 may be composed of PD-1 and HT-1.

[0173] 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 complexes of alkali metals and organic materials. In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0174] A fourth aspect of this application also provides an electronic device comprising the organic electroluminescent device described in the third aspect of this application.

[0175] For example, such as Figure 2 As shown, the electronic device provided in this application is a first electronic device 400, which includes any of the organic electroluminescent devices described in the above-described embodiments. This electronic device can be 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. Since the first electronic device 400 has the aforementioned organic electroluminescent device, it has the same beneficial effects, which will not be repeated here.

[0176] The present application will now be described in detail with reference to embodiments. However, the following description is intended to explain the present application and not to limit the scope of the present application in any way.

[0177] Synthesis Examples

[0178] Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many of the organic materials of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0179] Synthesis of intermediate IM-a:

[0180]

[0181] Under nitrogen protection, 2-(1,1'-biphenyl)-4-yl-4-chloro-6-phenyl-1,3,5-triazine (7.0 g; 20.4 mmol), 3,5-dichloro-2-fluorophenylboronic acid (4.3 g; 20.4 mmol), tetra(triphenylphosphine)palladium (0.5 g; 0.4 mmol), potassium carbonate (5.6 g; 40.7 mmol), tetrabutylammonium bromide (1.3 g; 4.1 mmol), toluene (60 mL), ethanol (15 mL), and deionized water (15 mL) were added to a round-bottom flask. The mixture was heated to 75-80 °C and stirred for 12 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to give a white solid intermediate IM-a (6.8 g; 71%).

[0182] Referring to the synthesis method of intermediate IM-a, reactant 1 in Table 1 below was used to replace intermediate c1 to synthesize the intermediates shown in Table 1 below:

[0183] Table 1

[0184]

[0185]

[0186]

[0187]

[0188] Referring to the synthetic method of intermediate IM-a, reactant 2 was substituted for intermediate 2-(1,1'-biphenyl)-4-yl-4-chloro-6-phenyl-1,3,5-triazine, and reactant 3 was substituted for 3,5-dichloro-2-fluorophenylboronic acid, to synthesize the intermediates shown in Table 2 below:

[0189] Table 2

[0190]

[0191] Synthesis of intermediate IM-t1:

[0192]

[0193] Under nitrogen protection, intermediate IM-FF (7.0 g; 13.2 mmol), (phenyl-d5)-boric acid (1.7 g; 13.2 mmol), tetrakis(triphenylphosphine)palladium (0.3 g; 0.3 mmol), potassium carbonate (3.6 g; 26.4 mmol), tetrabutylammonium bromide (0.9 g; 2.6 mmol), toluene (55 mL), ethanol (15 mL), and deionized water (15 mL) were added to a round-bottom flask. The mixture was heated to 75-80 °C and stirred for 18 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system, and then purified by recrystallization using a toluene / n-heptane solvent system to give a white solid intermediate IM-t1 (5.3 g; yield: 75%).

[0194] Following the synthetic method of intermediate IM-t1, (phenyl-d5)-boronic acid was replaced by reactant 4 in Table 2 to synthesize the intermediates shown in Table 2 below:

[0195] Table 2

[0196]

[0197] Synthesis of intermediate IM-1:

[0198]

[0199] Under nitrogen protection, intermediate IM-a (6.6 g; 14.0 mmol), phenylboronic acid (3.7 g; 30.7 mmol), palladium acetate (0.1 g; 0.3 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.3 g; 0.6 mmol), cesium carbonate (13.7 g; 41.9 mmol), toluene (80 mL), ethanol (20 mL), and deionized water (20 mL) were added to a round-bottom flask. The mixture was heated to 75-80 °C and stirred for 24 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain a white solid intermediate IM-1 (5.9 g; yield: 76%).

[0200] Following the synthetic method of intermediate IM-1, reactant 5 in Table 3 was used to replace intermediate IM-a, and reactant 6 was used to replace phenylboronic acid, to synthesize the intermediates shown in Table 2 below:

[0201] Table 3

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] Synthesis of intermediate IM-34:

[0208]

[0209] Under nitrogen protection, intermediate IM-t1 (5.2 g; 9.8 mmol), ([1,1-biphenyl]-3-yl-d9)boric acid (2.2 g; 10.7 mmol), palladium acetate (0.02 g; 0.1 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g; 0.2 mmol), cesium carbonate (4.8 g; 14.6 mmol), toluene (40 mL), ethanol (10 mL), and deionized water (10 mL) were added to a round-bottom flask. The mixture was heated to 75-80 °C and stirred for 16 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to give a white solid intermediate IM-34 (5.0 g; yield: 78%).

[0210] Following the synthetic method of intermediate IM-34, intermediate t1 was replaced by reactant 7 in Table 4, and ([1,1-biphenyl]-3-yl-d9)boronic acid was replaced by reactant 8 to synthesize the intermediates shown in Table 4 below:

[0211] Table 4

[0212]

[0213] Synthesis of compound 2:

[0214]

[0215] Under nitrogen protection, intermediate 1 (5.8 g; 10.4 mmol), carbazole (1.8 g; 11.0 mmol), cesium carbonate (6.8 g; 20.9 mmol), and dimethylformamide (60 mL) were added to a round-bottom flask and reacted with stirring at 145-150 °C for 12 hours. After cooling to room temperature, the reaction solution was washed with water and separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent, and then the obtained sample was purified by recrystallization using a toluene / n-heptane solvent system to give compound 2 (4.1 g; yield: 56%) as a white solid.

[0216] Following the synthetic method of compound 2, reactant 9 in Table 5 was used to replace intermediate IM-1, and reactant 10 was used to replace carbazole to synthesize the compounds shown in Table 3 below:

[0217] Table 5

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224] Mass spectrometry data of some compounds are shown in Table 6 below.

[0225] Table 6

[0226]

[0227]

[0228] NMR data for some compounds are shown in Table 7 below.

[0229] Table 7

[0230]

[0231] Synthesis of the second compound

[0232]

[0233] Under nitrogen protection, 5-phenyl-5,8-dihydroindolo[2,3-C]carbazole (20.0 g; 60.2 mmol), 1-bromo-3,5-diphenylbenzene (18.6 g; 60.2 mmol), tris(dibenzylacetone)dipalladium (0.5 g; 0.6 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.6 g; 1.2 mmol), sodium tert-butoxide (8.7 g; 90.3 mmol), and xylene (200 mL) were added to a round-bottom flask. The mixture was stirred at 140 °C for 6 hours. After cooling to room temperature, the reaction mixture was washed with water and separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solution as the eluent, and then the product was purified by recrystallization using a toluene / n-heptane solvent system to obtain a white solid compound B3-1 (27.0 g; yield: 80%).

[0234]

[0235] A solution was prepared by adding trifluoromethanesulfonic anhydride (74.0 g, 262.2 mmol) and heavy water (26.2 g, 1310.9 mmol) at 0 °C and stirring for at least 5 hours. B5-1 (15.0 g, 26.8 mmol) was added to 1,2,4-trichlorobenzene (150 mL) and the mixture was stirred. Then, the prepared trifluoromethanesulfonic anhydride and heavy water mixture was slowly added dropwise to the mixture of B5-1 and 1,2,4-trichlorobenzene. After the addition was complete, the temperature was raised to 120 °C. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare compound B5 (9.8 g; yield: 64%).

[0236] Following the synthetic method for compound B5, reactant g was used in the table below to replace compound 5-phenyl-5,8-dihydroindolo[2,3-C]carbazole, and reactant h was used to replace 1-bromo-3,5-diphenylbenzene to synthesize the compounds shown in Table 8 below:

[0237] Table 8

[0238]

[0239] The mass spectrometry data of some of the second compounds are shown in Table 9 below.

[0240] Table 9

[0241] Compound Mass spectral data Compound Mass spectral data Compound B5 m / z = 571.29 (M+H) + ]] Compound B14 m / z = 589.40 (M+H) + ]] Compound B17 m / z = 647.32 (M+H) + ]] Compound B25 m / z = 585.27 (M+H) + ]] Compound B21 m / z = 647.32 (M+H) + ]]

[0242] Fabrication of organic electroluminescent devices

[0243] Example 1: Fabrication of Green Organic Electroluminescent Devices

[0244] At ITO / Ag / ITO thickness On the experimental substrate, surface treatment is performed using ultraviolet light, ozone, and O2:N2 ions to increase the work function of the anode. Organic solvents can be used to clean the surface of the experimental substrate to remove impurities and oil stains.

[0245] Compounds HT-1 and PD-1 were co-deposited on an experimental substrate at a deposition rate ratio of 97%:3%, forming a layer with a thickness of [missing information]. A hole injection layer is formed, and then compound HT-1 is deposited on the hole injection layer to form a layer with a thickness of [missing information]. The hole transport layer.

[0246] Compound HT-2 was deposited on the hole transport layer to form a thickness of [missing information]. The light-emitting adjustment layer.

[0247] On the light-emitting adjustment layer, compound 2 (first compound), compound B5 (second compound), and GD-1 (doped guest) were co-deposited at a deposition rate ratio of 40%:60%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0248] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate ratio to form a layer with a thickness of [missing information]. The electron transport layer.

[0249] Yb is deposited on the electron transport layer to form a thickness of The electron injection layer.

[0250] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a deposition rate ratio of 10%:90%, forming a layer with a thickness of [missing information]. The cathode.

[0251] Compound CP-1 was deposited on the cathode to form a thickness of [missing information]. The organic coating layer is used to complete the fabrication of green organic electroluminescent devices.

[0252] Examples 2 to 41:

[0253] Except that the first and second compound combinations and evaporation rate ratios in Table 10 below are used instead of those in Example 1 when preparing the organic light-emitting layer, the organic electroluminescent device is prepared using the same method as in Example 1.

[0254] Comparative Examples 1 to 4:

[0255] Except that when preparing the organic light-emitting layer, the first and second compound combinations and evaporation rate ratios in Table 10 below are used instead of the first and second compound combinations and evaporation rate ratios in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0256] The compounds used in preparing the devices of the above embodiments and comparative examples have the following structures:

[0257]

[0258] The performance of the green organic electroluminescent devices prepared in Examples 1-41 and Comparative Examples 1-4 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 30 mA / cm. 2 The lifetime of the T95 device was tested under the following conditions, and the test results are shown in Table 10 below.

[0259] Table 10

[0260]

[0261]

[0262] As shown in the table above, compared with Comparative Examples 1 to 4, the device current efficiency of Examples 1 to 41 is improved by at least 13.9%, and the lifetime is improved by at least 15.7%.

[0263] The reason for this may lie in the fact that the core structure of the organic material provided in this application consists of carbazole and triazine linked ortho- and ortho- and phenyl groups on a phenylene oxide. Both the para- and ortho-positions of the carbazole have phenyl substituents, and the triazine contains specific aromatic groups. This linkage method gives the compound stronger electronic properties, thereby improving electron-hole recombination and increasing luminescence efficiency. Furthermore, the organic material in this application contains carbazole and triazine linked ortho- and phenyl substituents on the carbazole, increasing the steric hindrance of the compound and resulting in particularly excellent energy transfer efficiency for phosphorescent dopants. Therefore, this organic material is suitable as a phosphorescent host material. The para-position phenyl substituent on the carbazole helps improve the stability of the compound. The presence of triazine substituted with specific aromatic groups in the organic material of this application increases the electron mobility of the compound, thereby improving its luminescence efficiency.

[0264] Furthermore, this application provides an organic electroluminescent device, wherein the organic layer of the organic electroluminescent device includes an organic light-emitting layer, which comprises a first compound with strong electronic properties (the first compound is the organic material of this application) and a second compound with strong hole properties. Using the first and second compounds together as the host material of the organic light-emitting layer can regulate the balance of holes and electrons, enabling the organic light-emitting layer to generate more excitons, thereby improving the performance of the organic electroluminescent device. The second compound of this application is an indole-carbazole compound with a specific fusion method. This compound has strong hole properties, and its combination with the organic material of this application as the host material of the organic light-emitting layer can reduce the operating voltage of the organic electroluminescent device and improve the luminous efficiency and lifetime. In particular, when the core of the second compound is fully deuterated, the device performance is even better when combined with the first compound. In particular, the device performance is even better when all aromatic groups on the triazine are aryl groups.

[0265] The 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.

Claims

1. An organic material, characterized in that, The organic material has the structure shown in Formula 1: Where D represents deuterium; t represents the number of D, selected from 0, 1 or 2; L is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 30 carbon atoms; The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms. L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl groups with 6 to 30 carbon atoms respectively. The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, or alkoxy with 1 to 10 carbon atoms; Each R1, each R2, and each R3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms; n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different. n is the number of R2s, selected from 0, 1, 2, 3, 4 or 5. When n is greater than 1, any two R2s are the same or different. m is the number of R3s, selected from 0, 1, 2, 3, 4 or 5. When m is greater than 1, any two R3s are the same or different.

2. The organic material according to claim 1, characterized in that, The organic material has the structure shown in Formula 1-A: Where D represents deuterium; t, n, and m represent the number of D, where n and m are the same or different, and are independently selected from 0, 1, 2, 3, 4, or 5 respectively; t is selected from 0, 1, or 2. L is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 30 carbon atoms; The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms. L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl groups with 6 to 30 carbon atoms respectively. The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, or alkoxy with 1 to 10 carbon atoms; Each R1 may be the same or different, and is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms. n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

3. The organic material according to claim 1, characterized in that, 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 to 12 carbon atoms; Optionally, the substituents in L, L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, phenyl groups or pentadeuterated phenyl groups.

4. The organic material according to claim 1, characterized in that, L, L1, and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene. Optionally, the substituents in L, L1, and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, or pentadeuterated phenyl.

5. The organic material according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl groups with 6 to 20 carbon atoms respectively; Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, alkoxy with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 6 to 12 carbon atoms.

6. The organic material according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl. Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, methoxy, phenyl, naphthyl or pentadeuterated phenyl.

7. The organic material according to claim 1, characterized in that, In Equation 1 and They may be the same or different, and each is independently selected from the group consisting of the following groups:

8. The organic material according to claim 1, characterized in that, In Equation 1 Selected from the group consisting of the following groups:

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

10. A composition, characterized in that, The composition comprises a first compound and a second compound; The first compound is selected from the organic materials according to any one of claims 1 to 8, and the second compound is selected from the structure shown in Formula 2: Among them, each R4, each R5 and each R6 may be the same or different, and are independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, halogenated aryl with 6 to 20 carbon atoms or heteroaryl with 3 to 20 carbon atoms; n4 is the number of R4s, selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. n5 is the number of R5s, which can be selected from 0, 1 or 2. When n5 is greater than 1, any two R5s are the same or different. n6 is the number of R6, selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6 are the same or different. L4 and L5 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar4 and Ar5 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively. The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and are independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, or cycloalkyl groups with 3 to 10 carbon atoms.

11. The composition according to claim 10, characterized in that, In the second compound shown in Formula 2, L4 and L5 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl. Optionally, the substituents in L4 and L5 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

12. The composition according to claim 10, characterized in that, In the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiopheneyl. Optionally, the substituents in Ar4 and Ar5 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

13. The composition according to claim 10, characterized in that, The second compound shown in Formula 2 and They may be the same or different, and each is independently selected from the group consisting of the following groups:

14. The composition according to claim 10, characterized in that, In the second compound shown in Formula 2, each of R4, each of R5 and each of R6 may be the same or different, and each is independently selected from deuterium, phenyl or pentadeuterated phenyl.

15. The composition according to claim 10, characterized in that, The second compound shown in Formula 2 is selected from the group consisting of the following compounds:

16. An organic electroluminescent device, characterized in that, It includes an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; The functional layer comprises the organic material according to any one of claims 1 to 9 or the composition according to any one of claims 10 to 15; Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic material according to any one of claims 1 to 9 or the composition according to any one of claims 9 to 15; Optionally, the functional layer further includes a hole injection layer, a hole transport layer, a light emission adjustment layer, an electron transport layer, and an electron injection layer.

17. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 16.

Images