Triazine compounds, organic electroluminescent devices and electronic devices

Abstract

This application belongs to the field of organic electroluminescence technology, and relates to a triazine compound and an organic electroluminescent device and electronic device using the same. The triazine compound has a structure as shown in Formula I. Using the triazine compound in an organic electroluminescent device can improve the performance of the organic electroluminescent device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to a triazine compound, an organic electroluminescent device, and an electronic device. Background Technology

[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), 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 an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, 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 light-emitting 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.

[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] The purpose of this application is to provide a triazine compound, an organic electroluminescent device, and an electronic device to improve the performance of the organic electroluminescent device.

[0005] To achieve the above-mentioned objectives, this application adopts the following technical solution:

[0006] According to a first aspect of this application, a triazine-containing compound is provided, having the structure shown in Formula I:

[0007]

[0008] In formula I,

[0009] L1, L2 and L3 may be the same or different, and each is independently selected from the group consisting of single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups with 3 to 30 carbon atoms.

[0010] Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, and group A, and at least one of Ar1 and Ar2 is selected from group A;

[0011] Each R4 is independently selected from the group consisting of deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, deuteryl group with 1 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, triphenylsilyl group, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, and cycloalkyl group with 3 to 10 carbon atoms.

[0012] n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13;

[0013] The group A has the structure shown in Formula II:

[0014]

[0015] X is selected from O, S, N, N(Ar), CR, or C(R2R3);

[0016] Ar is selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0017] R, R2, and R3 may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuteralkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterylaryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 3 to 30 carbon atoms, or R2 and R3 together with the carbon atoms they are attached to form saturated or unsaturated 3 to 15-membered rings;

[0018] Each R1 is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0019] n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0020] The substituents in L1, L2, L3, Ar, Ar1, Ar2, R1, and R4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3 to 15-membered ring.

[0021] The triazine-containing compound provided in this application uses [5]helicene as the core and connects to a dibenzo5-substituted triazine. Both [5]helicene and the dibenzo5-substituted triazine have large conjugated planes and rigidity, and the triazine has excellent electron transport performance. After connecting [5]helicene and the dibenzo5-substituted triazine, on the one hand, the dibenzo5-substituted triazine has good electron transport characteristics, and combined with the rigid [5]helicene, it can further improve the electron mobility of the material; on the other hand, the first and fifth benzene rings at the end of [5]helicene are located in different planes due to the steric hindrance effect of hydrogen atoms, thus forming spatial planes with different multiple included angles within the molecule, which can effectively suppress the stacking between molecules and improve the film-forming properties of the material. When the triazine-containing compound of this application is used as the main material of the light-emitting layer, it can improve the balance of charge carriers in the light-emitting layer, improve the utilization rate of charge carriers, broaden the recombination region of charge carriers, and thus significantly improve the efficiency and lifetime of the device.

[0022] According to a second aspect of this application, an organic electroluminescent device is provided, 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 aforementioned triazine-containing compound.

[0023] According to a third aspect of this application, an electronic device is provided, the electronic device comprising the above-described organic electroluminescent device. Attached Figure Description

[0024] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application, wherein 100 represents the anode, 200 represents the cathode, 300 represents the functional layer, 310 represents the hole injection layer, 321 represents the first hole transport layer, 322 represents the second hole transport layer, 330 represents the organic light-emitting layer, 340 represents the electron transport layer, and 350 represents the electron injection layer.

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

[0026] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the 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.

[0027] In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0028] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

[0029] In a first aspect, this application provides a triazine-containing compound having the structure shown in Formula I:

[0030]

[0031] In formula I,

[0032] L1, L2 and L3 may be the same or different, and each is independently selected from the group consisting of single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups with 3 to 30 carbon atoms.

[0033] Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, and group A, and at least one of Ar1 and Ar2 is selected from group A;

[0034] Each R4 is independently selected from the group consisting of deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, deuteryl group with 1 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, triphenylsilyl group, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, and cycloalkyl group with 3 to 10 carbon atoms.

[0035] In this application, n4 refers to the number of substituents R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; when n4 is greater than 1, the substituents R4 may be the same or different.

[0036] The group A has the structure shown in Formula II:

[0037]

[0038] X is selected from O, S, N, N(Ar), C(R), or C(R2R3);

[0039] Ar is selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0040] R, R2, and R3 may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuteralkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterylaryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 3 to 30 carbon atoms, or R2 and R3 together with the carbon atoms they are attached to form saturated or unsaturated 3 to 15-membered rings;

[0041] Each R1 is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0042] In this application, n1 refers to the number of substituents R1, and n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n1 is greater than 1, the substituents R1 are the same or different;

[0043] The substituents in L1, L2, L3, Ar, Ar1, Ar2, R1, and R4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3 to 15-membered ring.

[0044] For example, in this application, "R2 and R3 together with the carbon atoms they are connected to form saturated or unsaturated 3- to 15-membered rings" means that R2 and R3 can be connected to each other to form a ring, or they can exist independently of each other; when they form a ring, the ring can be a 5-membered ring, such as... It can also be a 6-membered ring, such as It could also be a 13-membered ring, such as Other types of cyclic formation will not be listed here.

[0045] The triazine-containing compound provided in this application uses [5]helicene as the core and connects to a dibenzo5-substituted triazine. Both [5]helicene and the dibenzo5-substituted triazine have large conjugated planes and rigidity, and the triazine has excellent electron transport performance. After connecting [5]helicene and the dibenzo5-substituted triazine, on the one hand, the dibenzo5-substituted triazine has good electron transport characteristics, and combined with the rigid [5]helicene, it can further improve the electron mobility of the material; on the other hand, the first and fifth benzene rings at the end of [5]helicene are located in different planes due to the steric hindrance effect of hydrogen atoms, thus forming spatial planes with different multiple included angles in the molecule, which can effectively suppress the stacking between molecules and improve the film-forming properties of the material. When the triazine-containing compound of this application is used as the electron transport host material in the hybrid host material, it can improve the balance of charge carriers in the light-emitting layer, improve the carrier utilization rate, broaden the carrier recombination region, and thus significantly improve the efficiency and lifetime of the device.

[0046] In this application, the descriptive phrases "each...independently selected from," "...each independently selected from," and "...each 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.

[0047] 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, halogen groups, cyano, heteroaryl, aryl, trialkylsilyl, triphenylsilyl, alkyl, haloalkyl, cycloalkyl, deuterated phenyl, etc. The number of substituents can be one or more.

[0048] In this application, "multiple" means two or more, such as two, three, four, five, six, seven, eight, nine, ten or more.

[0049] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the sum of the number of carbon atoms in that functional group and all its substituents.

[0050] In this application, the number of carbon atoms in L1, L2, L3, R, R1, R2, R3, R4, Ar1, and Ar2 refers to the total number of carbon atoms in that group. For example, if Ar1 is selected from an aryl group with 10 substituted carbon atoms, then the total number of carbon atoms in the aryl group and its substituents is 10. As another example, if Ar1 is 9,9-dimethylfluorenyl, then Ar1 is a fluorenyl group with 15 substituted carbon atoms, and the number of carbon atoms in the cyclic group of Ar1 is 13.

[0051] In this application, unless otherwise specifically defined, "heteroatom" means a functional group comprising at least one heteroatom such as B, N, O, S, Si, Se, or P, with the remaining atoms being carbon and hydrogen. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.

[0052] In this application, "ring" includes saturated rings and unsaturated rings; saturated rings are saturated aliphatic rings, and unsaturated rings are partially unsaturated rings, such as cyclohexene or aromatic rings, such as aromatic rings and heteroaromatic rings.

[0053] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered ring. Saturated or unsaturated 3- to 15-membered rings refer to cyclic groups having 3 to 15 ring atoms. Examples of 3- to 15-membered rings include cyclopentane, cyclohexane, fluorene rings, and benzene rings.

[0054] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0055] 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. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0056] In this application, the term "arylene" refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0057] In this application, terphenyl includes

[0058] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, or 30 carbon atoms. 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 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0059] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0060] 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 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.

[0061] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0062] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl 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 a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 12.

[0063] 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 atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0064] 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.

[0065] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0066] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0067] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0068] 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.

[0069] In this application, the number of carbon atoms in the deuterated alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0070] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.

[0071] In this application, It refers to the chemical bond that connects with other groups.

[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 connect to any position in the ring system it traverses, and the other end connects 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 traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0073]

[0074] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0075]

[0076] 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):

[0077]

[0078] Optionally, the triazine-containing compound is selected from the structures shown in Formulas I-1 to I-7:

[0079]

[0080]

[0081] In the structures shown in Equations I-1 to I-7, the constraints of R4, L1, L2, L3, Ar1, Ar2, and n4 are the same as in Equation I.

[0082] In some embodiments, the group A is selected from the group consisting of structures shown in Formula II-1 to Formula II-2:

[0083]

[0084] In Equation II-1, X1 is selected from O, S, N (Ar) or C (R2R3), n1 is 0, 1, 2, 3, 4, 5, 6 or 7, and the restrictions of Ar, R1, R2 and R3 are the same as in Equation II.

[0085] In Equation II-2, X2 is selected from N or C(R), n1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the constraints of R and R1 are the same as in Equation II.

[0086] Optionally, the group A is selected from the group consisting of structures shown in Formula II-3 to Formula II-5:

[0087]

[0088] In Equation II-3, X1 is selected from O, S, N (Ar) or C (R2R3), n1 is 0, 1, 2 or 3, and the constraints of Ar, R1, R2 and R3 are the same as in Equation II;

[0089] In Equation II-4, X2 is selected from O, S, N (Ar) or C (R2R3), n1 is 0, 1, 2, 3, 4, 5 or 6, and the constraints of Ar, R, R1, R2 and R3 are the same as in Equation II;

[0090] In Equation II-5, X2 is selected from N or C(R), n1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the constraints of R and R1 are the same as in Equation II.

[0091] In some embodiments, group A is selected from the group consisting of:

[0092]

[0093]

[0094] Optionally, Ar is selected from aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 12 carbon atoms, or heteroaryl groups having 5 to 12 carbon atoms;

[0095] R, R2, and R3 may be the same or different, and each is independently selected from alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, deuteralkyl groups having 1 to 4 carbon atoms, aryl groups having 6 to 12 carbon atoms, deuteralkyl groups having 6 to 12 carbon atoms, or heteroaryl groups having 5 to 12 carbon atoms, or R2 and R3 together with the carbon atoms they are connected to form a fluorene ring.

[0096] Optionally, each R1 is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuteryl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, triphenylsilyl, substituted or unsubstituted aryl with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl with 5 to 18 carbon atoms;

[0097] n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0098] Optionally, the substituents in R1 are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 4 carbon atoms, haloalkyl groups with 1 to 4 carbon atoms, deuteralkyl groups with 1 to 4 carbon atoms, alkoxy groups with 1 to 4 carbon atoms, alkylthio groups with 1 to 4 carbon atoms, trialkylsilyl groups with 3 to 8 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 12 carbon atoms, and heteroaryl groups with 5 to 12 carbon atoms.

[0099] In some embodiments, the group A is selected from the group consisting of groups represented by formulas A1 to A9:

[0100]

[0101] In equations A1 to A9 above, the constraints of R1 and n1 are the same as in equation I.

[0102] Optionally, in the above formulas A1 to A9, each R1 is independently selected from deuterium, cyano, fluorine, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuteryl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl with 5 to 18 carbon atoms.

[0103] Optionally, the substituents in R1 are each independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, deuterated alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms, or heteroaryl with 5-12 carbon atoms.

[0104] In some embodiments, each R1 and R4 is independently selected from alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, deuteralkyl groups having 1 to 4 carbon atoms, 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 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0105] Optionally, the substituents in each of R1 and R4 are independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl.

[0106] In some embodiments, each R1 and R4 is independently selected from deuterium, cyano, fluorine, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuteryl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl with 5 to 18 carbon atoms.

[0107] In some embodiments, R1 and R4 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl.

[0108] Optionally, the substituents in R1 and R4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophene, or trimethylsilyl.

[0109] Preferably, R1 and R4 are each independently selected from the group consisting of deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, or the group consisting of:

[0110]

[0111] In some embodiments, each R4 is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, or the following groups:

[0112]

[0113]

[0114] In some embodiments, each R1 is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or the following groups:

[0115]

[0116] In some embodiments, R, R2, and R3 are each independently selected from alkyl groups having 1 to 6 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, deuteralkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 16 carbon atoms, deuteralkyl groups having 6 to 16 carbon atoms, or heteroaryl groups having 3 to 15 carbon atoms.

[0117] Optionally, Ar is selected from aryl groups having 6 to 16 carbon atoms, deuterated aryl groups having 6 to 16 carbon atoms, or heteroaryl groups having 3 to 15 carbon atoms.

[0118] Optionally, R, R2 and R3 are each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated naphthyl or deuterated biphenyl.

[0119] Ar can optionally be selected from phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated naphthyl or deuterated biphenyl.

[0120] In some embodiments, group A is selected from the group consisting of:

[0121]

[0122]

[0123] In some embodiments, L1, L2, and L3 are each independently selected from single bonds, 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 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0124] In some embodiments, L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms.

[0125] Optionally, the substituents in L1, L2 and L3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 5-12 carbon atoms.

[0126] In some embodiments, L1, L2, and L3 are selected from the group consisting of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl, or a subunit group formed by connecting two or three of the above subunits through a single bond, such as a subunit group formed by connecting phenylene and naphthylene through a single bond, or a subunit group formed by connecting phenylene and biphenylene through a single bond.

[0127] Optionally, the substituents in L1, L2 and L3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl or pyridyl.

[0128] In some embodiments, L1, L2, and L3 may be the same or different, and each is independently selected from single-bonded or substituted or unsubstituted groups Q, wherein the unsubstituted group Q is selected from the group consisting of:

[0129]

[0130] The substituents in the above-mentioned substituted groups Q may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl or pyridyl.

[0131] In some embodiments, L1 is selected from single bonds or the following groups:

[0132]

[0133] In some embodiments, L2 and L3 are each independently selected from single bonds or the following groups:

[0134]

[0135] In some embodiments, one of Ar1 and Ar2 is group A, and the other is selected from the group consisting of 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, substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, or group A.

[0136] In some embodiments, one of Ar1 and Ar2 is group A, and the other is selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms, and group A.

[0137] Further optionally, Ar1 is group A, and Ar2 is selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms, and group A.

[0138] Alternatively, Ar1 and Ar2 are both groups A.

[0139] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, deuterated alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms, or heteroaryl with 5-12 carbon atoms.

[0140] In some embodiments, Ar1 is group A, and Ar2 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 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0141] In some embodiments, Ar1 is group A, and Ar2 is selected from substituted or unsubstituted group T, wherein the unsubstituted group T is selected from the group consisting of:

[0142]

[0143] The substituted group T has one or more substituents, each substituent being independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl, and when the number of substituents in the group W is greater than 1, the substituents may be the same or different.

[0144] Alternatively, Ar2 is selected from the group consisting of:

[0145]

[0146] Optionally, for and Selected from the group consisting of the following groups:

[0147]

[0148] Optionally, Selected from the group consisting of the following groups:

[0149]

[0150]

[0151]

[0152] Further optional, Selected from the group consisting of the following groups:

[0153]

[0154]

[0155] Optionally, the triazine-containing compound is selected from the group consisting of:

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] A second 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 comprises the aforementioned triazine compound to improve the voltage characteristics, efficiency characteristics and lifetime characteristics of the organic electroluminescent device.

[0166] Optionally, the triazine-containing compound provided in this application can be used to form at least one organic film layer in the functional layer.

[0167] Optionally, the functional layer includes an organic light-emitting layer, which includes the triazine-containing compound. The organic light-emitting layer may be composed of the triazine-containing compound provided in this application, or it may be composed of the triazine-containing compound provided in this application and other materials.

[0168] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (also called a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked sequentially.

[0169] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or 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.

[0170] In this application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0171]

[0172] In one embodiment, the first hole transport layer 321 may be composed of HT-1.

[0173] In one embodiment, the second hole transport layer 322 is composed of HT-2.

[0174] Optionally, a hole injection layer 310 is further provided 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. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof:

[0175]

[0176]

[0177] In one embodiment, the hole injection layer 310 is composed of PD and α-NPD.

[0178] 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. Optionally, 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.

[0179] The host material of the organic light-emitting layer 330 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material comprises a triazine-containing compound of this application; further optionally, the host material of the organic light-emitting layer 330 comprises at least one of compounds 1 to 324 of this application. Optionally, the host material may also comprise RH-P.

[0180] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to:

[0181]

[0182] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the triazine-containing compound of this application. The guest material is, for example, RD-1.

[0183] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the triazine-containing compound of this application. The guest material may be, for example, fac-Ir(ppy)3.

[0184] 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 materials may be selected from, but are not limited to, BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0185]

[0186] In one embodiment of this application, the electron transport layer 340 may be composed of ET-1 and LiQ, or ET-2 and LiQ.

[0187] 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. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0188] Optionally, 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. In one embodiment of this application, the electron injection layer 350 may include ytterbium (Yb).

[0189] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0190] According to one implementation method, such as Figure 2As shown, the provided 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 including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0191] Synthesis example

[0192] The following synthetic examples and embodiments are used to further illustrate and explain the contents of this application.

[0193] Generally, the nitrogen-containing compounds of this application can be prepared by the methods described herein. Unless otherwise specified, the meanings of the substituent symbols in this application are the same as those in Chemical Formula I. Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many other triazine-containing compounds of this application, and other methods for preparing the triazine-containing compounds of this application are considered to be within the scope of this invention.

[0194] For example, those skilled in the art can synthesize other triazine-containing compounds of this application by referring to or appropriately modifying the preparation methods provided in this application, such as by using appropriate protecting groups, utilizing other known reagents other than those described in this application, or modifying reaction conditions.

[0195] In the synthesis examples described below, all temperatures are in degrees Celsius unless otherwise stated. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company, Arco Chemical Company, and Alfa Chemical Company, and were used without further purification unless otherwise stated. Some common reagents were purchased from Shantou Xilong Chemical Plant, Guangdong Guanghua Chemical Reagent Plant, Guangzhou Chemical Reagent Plant, Tianjin Haoyuyu Chemical Co., Ltd., Tianjin Fuchen Chemical Reagent Plant, Wuhan Xinhuayuan Technology Development Co., Ltd., Qingdao Tenglong Chemical Reagent Co., Ltd., and Qingdao Haiyang Chemical Plant. Toluene was obtained by reflux drying with metallic sodium. n-Hexane was pre-dried with anhydrous sodium sulfate before use.

[0196] Unless otherwise stated, the following reactions are generally carried out under positive pressure of nitrogen or argon, or with a drying tube attached to an anhydrous solvent; reaction flasks are sealed with suitable rubber stoppers, and the substrate is injected into the reaction flasks using a syringe. All glassware is dried.

[0197] 1 HNMR spectra were recorded using a Bruker 400MHz or 600MHz nuclear magnetic resonance spectrometer. 1¹H NMR spectra use CDCl₃, CD₂Cl₂, D₂O, DMSO-d₆, CD₃OD, or acetone-d₆ as solvents (in ppm), and TMS (0 ppm) or chloroform (7.26 ppm) as reference standards. When multiplets are observed, the following abbreviations are used: s (singlet), d (doublet), t (triplet), m (multiplet), br (broadened), dd (doublet of doublets), ddd (doublet of doublets), dddd (doublet of doublets), dt (doublet of triplets), tt (triplet of triplets). The coupling constant J is expressed in Hertz (Hz). The determination conditions for low-resolution mass spectrometry (MS) data were as follows: Agilent 6120 quadrupole HPLC-M (column model: Zorbax SB-C18, 2.1 × 30 mm, 3.5 μm, 6 min, flow rate: 0.6 mL / min; mobile phase: 5%-95% (acetonitrile containing 0.1% formic acid) in (H2O containing 0.1% formic acid), electrospray ionization (ESI) at 210 nm / 254 nm, and UV detection.

[0198] Synthesis of Sub-a1:

[0199]

[0200] Under a nitrogen atmosphere, RM-1 (CAS: 1427675-68-0, 13.41 g, 50 mmol), 1-iodo-3-bromonaphthalene (16.64 g, 50 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous sodium carbonate (10.6 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (13.31 g, yield 62%).

[0201] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a4 were synthesized by replacing 1-iodo-3-bromonaphthalene with reactant A shown in Table 1.

[0202] Table 1: Synthesis of Sub-a2 to Sub-a4

[0203]

[0204] Synthesis of Sub-b1:

[0205]

[0206] Under a nitrogen atmosphere, Sub-a1 (21.47 g, 50 mmol), tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution, 150 mL), and deionized water (150 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred at room temperature for 2 hours. The flask was then extracted with dichloromethane (50 mL × 3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (15.72 g; yield 88%).

[0207] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b4 were synthesized by replacing Sub-a1 with reactant B shown in Table 2.

[0208] Table 2: Synthesis of Sub-b2 to Sub-b4

[0209]

[0210] Synthesis of Sub-c1:

[0211]

[0212] Under a nitrogen atmosphere, Sub-b1 (17.86 g, 50 mmol), platinum dichloride (0.916 g, 0.66 g, 2.5 mmol), and toluene (180 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred for 24 hours. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (13.93 g; yield 78%).

[0213] Sub-c2 to Sub-c4 were synthesized by replacing Sub-b1 with reactant C as shown in Table 3, referring to Sub-c1.

[0214] Table 3: Synthesis of Sub-c2 to Sub-c4

[0215]

[0216]

[0217] Synthesis of Sub-c5:

[0218]

[0219] Under a nitrogen atmosphere, RM-2 (CAS: 221683-78-9, 26.17 g, 60 mmol), phenylboronic acid (6.10 g, 50 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous sodium carbonate (10.6 g, 100 mmol), toluene (140 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (11.70 g, yield 54%).

[0220] Sub-c6 and Sub-c7 were synthesized by replacing phenylboronic acid with reactant D shown in Table 4, as in Sub-c5.

[0221] Table 4: Synthesis of Sub-c6 and Sub-c7

[0222]

[0223] Synthesis of Sub-d1:

[0224]

[0225] Under a nitrogen atmosphere, Sub-c1 (25.0 g, 70 mmol) and tetrahydrofuran (dry, 250 mL) were added to a 500 mL three-necked flask. The system was cooled to -78 °C, and a solution of n-butyllithium (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the system was kept at -78 °C and stirred for 1 hour. Trimethyl borate (10.91 g, 105 mmol) was added dropwise while maintaining the temperature at -78 °C. After the addition was complete, the system was kept at -78 °C for another 1 hour, and then allowed to warm to room temperature naturally. Dilute hydrochloric acid (2 M, 58 mL) was added dropwise to the reaction solution and stirred for 30 minutes. The mixture was extracted with dichloromethane (100 mL × 3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was slurried with n-heptane and filtered to obtain a white solid product, Sub-d1 (13.98 g, yield 62%).

[0226] Sub-d2 to Sub-d9 were synthesized by replacing Sub-c1 with reactant E as shown in Table 5, referring to Sub-d1.

[0227] Table 5: Synthesis of Sub-d2 to Sub-d9

[0228]

[0229]

[0230] Synthesis of Sub-e1:

[0231]

[0232] Under a nitrogen atmosphere, 2-(1,1'-phenyl-2-yl)-4,6-dichloro-1,3,5-triazine (22.66 g, 75 mmol), N-phenyl-3-carbazoleboric acid (14.35 g, 50 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (220 mL), and deionized water (55 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the reaction was carried out at 65-70 °C for 16 hours. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was recrystallized from toluene to give a white solid Sub-e1 (14.25 g, yield 56%).

[0233] Referring to Sub-e1, Sub-e2 to Sub-e19 were synthesized by replacing 2-(1,1'-phenyl-2-yl)-4,6-dichloro-1,3,5-triazine with reactant F shown in Table 6 and replacing N-phenyl-3-carbazoleboronic acid with reactant G.

[0234] Table 6: Synthesis of Sub-e2 to Sub-e19

[0235]

[0236]

[0237]

[0238] Synthesis of Sub-f1:

[0239]

[0240] Under a nitrogen atmosphere, RM-3 (CAS: 2173555-96-7, 18.69 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (180 mL), tetrahydrofuran (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 hours. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (17.77 g, yield 79%).

[0241] Referring to Sub-f1, Sub-f2 to Sub-f20 were synthesized by replacing RM-3 with reactant H and 3-chlorophenylboronic acid with reactant J as shown in Table 7.

[0242] Table 7: Synthesis of Sub-f2 to Sub-f20

[0243]

[0244]

[0245]

[0246] Synthesis of Compound 1:

[0247]

[0248] Under a nitrogen atmosphere, Sub-d5 (17.72 g, 55 mmol), RM-4 (CAS: 2142681-84-1, 17.89 g, 50 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (180 mL), tetrahydrofuran (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 hours. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase, yielding a white solid (24.58 g, yield 82%, m / z = 600.2 [M+H)). + ).

[0249] Referring to the synthesis of compound 1, reactant K was used instead of Sub-d5 and reactant L was used instead of RM-4 as shown in Table 8 to synthesize the compounds of this application in Table 8.

[0250] Table 8: Synthesis of the compounds in this application

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] The NMR data for some compounds are as follows:

[0258]

[0259] Synthesis of compound 116:

[0260]

[0261] Under a nitrogen atmosphere, Sub-f1 (22.49 g, 50 mmol), Sub-d1 (17.72 g, 55 mmol), palladium acetate (0.12 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.47 g, 1.0 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), tetrahydrofuran (220 mL), and deionized water (55 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 hours. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase, yielding a white solid (25.94 g, yield 75%, m / z = 692.2 [M+H)). + ).

[0262] Referring to the synthesis of compound 116, reactant M was used instead of Sub-f1 and reactant N was used instead of Sub-d1 as shown in Table 9 to synthesize the compounds of this application in Table 9.

[0263] Table 9: Synthesis of the compounds in this application

[0264]

[0265]

[0266]

[0267] The NMR data for compound 188 are as follows:

[0268] 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm8.91(s1H),8.85(d,2H),8.64(d,1H),8.39(d,1H),8.35( d,1H),8.25(d,1H),8.07(d,1H),7.98(d,1H),7.95-7.55(m,18H),7.52-7.44(m,2H),7.38-7.33(m,2H).

[0269] Synthesis of compound 274:

[0270]

[0271] Under a nitrogen atmosphere, compound 188 (18.15 g, 25 mmol) and 200 mL of benzene-D6 were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 minutes. A saturated aqueous solution of K3PO4 was then added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the combined organic phases were dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give a white solid (12.68 g, yield 67%, m / z = 757.4 [M+H)). + ).

[0272] Device Examples

[0273] This invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises the aforementioned organic compound of this invention. The organic electroluminescent device of this invention will now be described in detail through embodiments. However, the following embodiments are merely examples of this invention and are not intended to limit the invention.

[0274] Example 1: Red Organic Electroluminescent Device

[0275] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0276] On the experimental substrate (anode), PD:α-NPD was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then an α-NPD is vacuum-deposited on the hole injection layer to form a layer with a thickness of [missing information]. The first hole transport layer.

[0277] Compound HT-2 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0278] Next, on the second hole transport layer, compound 1:RH-P:RD-1 was co-deposited at a deposition rate of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0279] On the light-emitting layer, compound ET-1 and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition. A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with 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.

[0280] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP-1 forms a capping layer (CPL), thereby completing the fabrication of the red organic electroluminescent device.

[0281] Examples 2-58

[0282] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compounds 3 to 311 in Table 10 were used instead of compound 1 in Example 1 when fabricating the light-emitting layer.

[0283] Comparative Examples 1-4

[0284] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compound A, compound B, and compound C were used instead of compound 1 in Example 1 when fabricating the light-emitting layer.

[0285] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0286]

[0287] The performance of the red organic electroluminescent devices prepared in Examples 1-58 and Comparative Examples 1-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 10.

[0288] Table 10

[0289]

[0290]

[0291]

[0292] Referring to Table 10 above, by comparing the performance of the organic electroluminescent devices prepared in Examples 1 to 58 with those in Comparative Examples 1 to 4, when the triazine compound of the present invention is used as the main material of the red organic electroluminescent device, the luminous efficiency of the organic electroluminescent device is increased by at least 14.3% and the lifetime is increased by at least 12.8%.

[0293] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

[0294] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention will not describe the various possible combinations separately.

[0295] Furthermore, various different embodiments of the present invention can be combined in any way, as long as they do not violate the spirit of the present invention, they should also be regarded as the content disclosed by the present invention.

Claims

1. A triazine-containing compound, characterized by, The triazine-containing compound has the structure shown in Formula I: Formula I In formula I, L1 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted phenanthrene; L2 and L3 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted dibenzothiopheneylene. Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of substituted or unsubstituted groups T and groups A, and at least one of Ar1 and Ar2 is selected from group A; the unsubstituted group T is selected from the group consisting of the following groups: ； The group A has the structure shown in Formula II: Formula II X is selected from O, S, N, N(Ar), C(R), or C(R2R3); Ar is selected from phenyl or deuterated phenyl; R is selected from phenyl or deuterated phenyl; R2 and R3 may be the same or different, and each is independently selected from methyl, phenyl or deuterated phenyl, or R2 and R3 together with the carbon atom they are connected to form a spirodifluorene ring; Each R1 and each R4 are independently selected from deuterium, fluorine, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, or substituted or unsubstituted phenanthryl; n1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; The substituents in L1, L2, L3, groups T, R1, and R4 may be the same or different, and each is independently selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl. Furthermore, the triazine-containing compound is not one of the following compounds: 。 2. The triazine-containing compound according to claim 1, characterized in that, The compounds are selected from the structures shown in Formulas I-1 to I-7: Formula I-1 Formula I-2 Formula I-3 Formula I-4 Formula I-5 Formula I-6 Formula I-7 In the structures shown in Equations I-1 to I-7, the constraints of R4, L1, L2, L3, Ar1, Ar2, and n4 are the same as in Equation I.

3. The triazine-containing compound according to claim 1 or 2, characterized in that, Group A is selected from the group consisting of the following groups: Restricted isoform II for Ar, R, R1, n1, R2, and R3.

4. The triazine-containing compound according to claim 1 or 2, characterized in that, Group A is selected from the groups represented by the following formulas A1 to A9: Formula A1 Formula A2 Formula A3 A4, A5, A6 Type A7, Type A8, Type A9 In the above formulas A1 to A9, the limitation of each R1 is the same as in formula II.

5. The triazine-containing compound according to claim 1 or 2, characterized in that, Each R1 and R4 is independently selected from the group consisting of deuterium, fluorine, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or the following groups: 。 6. The triazine-containing compound according to claim 1 or 2, characterized by Group A is selected from the group consisting of the following groups: 。 7. The triazine-containing compound according to claim 1 or 2, characterized in that, selected from the group consisting of: 。 8. Triazine-containing compounds characterized in that, The triazine-containing compound is selected from the group consisting of the following compounds: 。 9. An organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises a triazine-containing compound as described in any one of claims 1-8.

10. The organic electroluminescent device according to claim 9, which comprises an organic light-emitting layer, characterized in that The organic light-emitting layer includes the triazine-containing compound.

11. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 9 or 10.

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