Organic compound, organic electroluminescent device, and electronic device

Abstract

The invention relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device containing the same and an electronic device. According to the compound, tetramethyl cyclohexane carbazolyl fused aryl five-membered ring serves as a core structure of the compound, and when the compound serves as a main body material of a light-emitting layer, carrier balance in the light-emitting layer can be improved, a carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, the light-emitting efficiency of a device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to organic compounds and organic electroluminescent devices and electronic devices containing the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Organic electroluminescent devices (OLEDs) generally include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases. In organic electroluminescent devices, the light-emitting layer material has the most significant impact on lifespan and efficiency. Therefore, in order to improve the light-emitting efficiency and service life, it is necessary to continuously improve the light-emitting layer material.

[0004] Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the invention

[0005] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound and an electronic component and an electronic device containing the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0006] According to a first aspect of the present application, an organic compound is provided, which has a structure shown by the following formula 1:

[0007]

[0008] Ring A is selected from a benzene ring, a naphthalene ring or a phenanthrene ring;

[0009] X is selected from O, S, C(R4R5);

[0010] R4 and R5 are each independently selected from an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or R4 and R5 are connected to each other and form a ring with the carbon atom to which they are connected;

[0011] W is selected from the structure shown in formula a-1 or the structure shown in formula a-2;

[0012]

[0013] L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0014] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0015] Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;

[0016] Ar1 and Ar2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0017] The substituents in L, L1, L2, L3, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, and optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0018] Each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms;

[0019] n1 is selected from 0, 1 or 2; when n1 is greater than, each R1 is the same or different;

[0020] n2 is selected from 0, 1 or 2; when n2 is greater than, each R2 is the same or different; optionally, adjacent R2 forms a benzene ring;

[0021] n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n3 is greater than, each R3 is the same or different.

[0022] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0023] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0024] The structure of the compound of the present application contains tetramethylcyclohexane and carbazole-fused aryl and five-membered ring as the parent core, and the parent core is further connected to an aryl or heteroaryl group through the N atom in carbazole. The tetramethylcyclohexane and carbazole in the parent core has excellent hole transport ability, and the structure of tetramethylcyclohexane can further enhance the hole transport ability of the group through the hyperconjugation effect, giving the compound of the present application excellent hole transport ability. When the parent core of the compound of the present application is connected to an aryl or heteroaryl group, it can constitute a main material with an excellent light-emitting layer. The spatial configuration of tetramethylcyclohexane is outside the conjugated plane of the entire group, forming a certain steric hindrance, which can finely regulate the stacking between compound molecules, and can make the compound form a better amorphous film. When the compound of the present application is used as the main material, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the device luminous efficiency and life can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0026] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0027] Figure 2 It is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.

[0028] Reference numerals

[0029] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0030] 321, first hole transport layer 322, second hole transport layer 320, hole transport layer 330, organic light emitting layer

[0031] 340, electron transport layer 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0032] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0033] In a first aspect, the present application provides an organic compound having a structure shown in the following formula 1:

[0034]

[0035] Wherein, ring A is selected from a benzene ring, a naphthalene ring or a phenanthrene ring;

[0036] X is selected from O, S, C(R4R5);

[0037] R4 and R5 are each independently selected from an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or R4 and R5 are connected to each other and form a ring with the carbon atom to which they are connected;

[0038] W is selected from the structure shown in formula a-1 or the structure shown in formula a-2;

[0039]

[0040] L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0041] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0042] Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;

[0043] Ar1 and Ar2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0044] The substituents in L, L1, L2, L3, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, and optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0045] Each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms;

[0046] n1 is selected from 0, 1 or 2; when n1 is greater than, each R1 is the same or different;

[0047] n2 is selected from 0, 1 or 2; when n2 is greater than, each R2 is the same or different; optionally, adjacent R2 forms a benzene ring;

[0048] n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n3 is greater than, each R3 is the same or different.

[0049] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. For another example, "L, L1, L2, L3, Ar1, Ar2 and Ar3, optionally, any two adjacent substituents form a ring" means that any two adjacent substituents in L, L1, L2, L3, Ar1, Ar2 and Ar3 are connected to each other to form a ring, or any two adjacent substituents in Ar1, Ar2 and Ar3 can also exist independently. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms having one substituent respectively; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are connected; when there is one substituent on two adjacent atoms respectively, the two substituents can be fused into a ring.

[0050] In this application, the descriptions "each ... independently is" and "... independently is" and "... independently is" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example,

[0051] Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0052] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be 1 or more.

[0053] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0054] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0055] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0056] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl connected by a carbon-carbon single bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon single bond, two or more condensed ring aryl connected by a carbon-carbon single bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon single bond can also be regarded as aryl of the present application. Wherein, condensed ring aryl, for example, can include a dicyclic condensed aryl (e.g., naphthyl), a tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0057] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0058] In the present application, terphenyl includes

[0059] In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents is 18.

[0060] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38 or 40, etc. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 40 carbon atoms; in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms; in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.

[0061] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0062] In the present application, the aryl group as a substituent of L, L1, L2, L3, Ar1, Ar2 and Ar3 includes, but is not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0063] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon single bond, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0064] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0065] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 40; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12.

[0066] In the present application, the heteroaryl groups as substituents of L, L1, L2, L3, Ar1, Ar2 and Ar3 are exemplified but not limited to pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl and dibenzofuranyl.

[0067] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

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

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

[0070] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0071] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0072] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0073] In the present application, a deuterated aryl group refers to an aryl group containing deuterium, such as but not limited to, a deuterated phenyl group, a deuterated naphthyl group, a deuterated biphenyl group, and the like.

[0074] In the present application, the halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl and the like.

[0075] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0076] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. "-#", It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0077]

[0078] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

[0079]

[0080] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, and the meaning represented by it includes any possible connection mode shown in formula (Y-1) to formula (Y-7):

[0081]

[0082] In some embodiments, the structure of Formula 1 is selected from the following structures represented by Formulas (i-1) to (i-34):

[0083]

[0084]

[0085]

[0086] In some embodiments, in formula (i-1) to formula (i-34), each R1, R2 and R3 are the same or different, and are each independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0087] In some embodiments, each R1, R2 and R3 are the same or different and are each independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, and optionally, any two adjacent R2 form a benzene ring.

[0088] In some embodiments, R4 and R5 are the same or different and are independently selected from trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, or R4 and R5 are connected to each other and form a fluorene ring, cyclopentane or cyclohexane with the carbon atom to which they are connected.

[0089] In the compounds of the present application, tetramethylcyclohexane and carbazole are fused with an aromatic group and a five-membered ring connected to a W group. When the W group is selected from a hole transport group, a material with excellent hole transport properties can be formed; when the W group contains an electron-deficient nitrogen-containing heteroaryl, an electronic light-emitting layer main material or a bipolar light-emitting layer main material can be formed. Specifically, in the compounds of the present application, cyclohexane is fused to the benzene ring on one side of the carbazole ring, and an aromatic group and a five-membered ring are fused to the benzene ring on the other side of the carbazole ring. This parent core structure enables the compound to have a higher hole transport efficiency. When the parent core is connected to a hole transport group, there is a wider conjugated region between the parent core and the W group, and the hole mobility is further improved. The compound can significantly improve the luminous efficiency and life of the device as a hole transport type light-emitting layer main body; when the parent core is connected to an electron transport group, the parent core and the W group have hole and electron transport capabilities respectively, and the compound has dual carrier transport capabilities. As a bipolar light-emitting layer main body, the luminous efficiency and life of the device can be significantly improved.

[0090] In some embodiments, Het is selected from the following groups:

[0091]

[0092]

[0093] -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In the above formula, L2 is a single bond and Ar2 is hydrogen.

[0094] Optionally, Het is selected from the following groups:

[0095]

[0096] -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In the above formula, L2 is a single bond and Ar2 is hydrogen.

[0097] In some embodiments, L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0098] In some embodiments, L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0099] Optionally, the substituents in L, L1, L2 and L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group.

[0100] In some embodiments, L, L1, L2 and L3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.

[0101] Optionally, the substituents in L, L1, L2 and L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0102] In some embodiments, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0103]

[0104] In some embodiments, L and L3 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0105]

[0106] In some embodiments, L and L3 are each independently selected from a single bond or the following groups:

[0107]

[0108] In some embodiments, L1 and L2 are each independently selected from a single bond or the following groups:

[0109]

[0110]

[0111] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms.

[0112] In some embodiments, Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.

[0113] In some embodiments, Ar1 and Ar3 are each independently selected from hydrogen, substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0114] In some embodiments, Ar2 is selected from hydrogen, substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0115] In some embodiments, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a trialkylsilyl group having 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0116] In some embodiments, Ar1 and Ar3 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or substituted or unsubstituted benzimidazolyl.

[0117] Optionally, Ar2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0118] Optionally, the substituents in Ar1, Ar2 and Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl.

[0119] In some embodiments, Ar1 is selected from the following groups:

[0120]

[0121]

[0122] Optionally, Ar2 is selected from the following groups:

[0123]

[0124] Optionally, Ar3 is selected from the following groups:

[0125]

[0126] In some embodiments, Ar1 and Ar3 are each independently selected from the following groups; Ar2 is selected from hydrogen or the following groups:

[0127]

[0128]

[0129] In some embodiments, Selected from the group consisting of:

[0130]

[0131] In some embodiments, Selected from the group consisting of the following groups, is selected from hydrogen or the following groups:

[0132]

[0133]

[0134] In some embodiments, Selected from the group consisting of:

[0135]

[0136]

[0137] Optionally, the organic compound is selected from the group consisting of the compounds shown below:

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] In a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of the present application.

[0146] The organic compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and life span of the organic electroluminescent device.

[0147] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound. The organic light-emitting layer can be composed of the organic compound provided in the present application, or can be composed of the organic compound provided in the present application and other materials.

[0148] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, the 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 light-emitting 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 in sequence.

[0149] In the present 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0150] In the present application, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer (also called a light-emitting auxiliary layer) 322, which 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, and may be specifically selected from the following compounds or any combination thereof:

[0151]

[0152]

[0153] In one embodiment, the first hole transport layer 321 may be composed of NPB.

[0154] In one embodiment, the second hole transport layer 322 is composed of HT-1.

[0155] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any special restrictions on this. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;

[0156]

[0157] In one embodiment, the hole injection layer 310 is composed of HAT-CN.

[0158] In the present application, the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0159] The host material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. Optionally, the host material includes the organic compound of the present application.

[0160] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,

[0161]

[0162]

[0163] In one embodiment of the present 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 organic compound of the present application. The guest material is, for example, Ir(piq)2acac.

[0164] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions. The materials of the electron transport layer 340 include but are not limited to the following compounds:

[0165]

[0166] In one embodiment of the present application, the electron transport layer 340 may consist of ET-1 and LiQ, or consist of ET-2 and LiQ.

[0167] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0168] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).

[0169] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0170] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0171] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereby.

[0172] Synthesis Example

[0173] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds of the synthetic methods not mentioned in the present invention are all raw materials obtained through commercial channels.

[0174] Synthesis of R-0:

[0175]

[0176] Under nitrogen atmosphere, CAS: 2221994-80-3 (15.0 g, 50 mmol), diboronic acid pinacol ester (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and when the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added, and the temperature was continued to rise to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, stirred thoroughly for 30 min, and filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved with 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, a white solid R-0 (11.84 g, yield 68%) was obtained.

[0177] Synthesis of R-3:

[0178]

[0179] Under nitrogen atmosphere, CAS: 1674335-43-3 (18.66 g, 50 mmol), diboronic acid pinacol ester (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and when the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added, and the temperature was continued to rise to reflux, and the reaction was stirred overnight. After the system is cooled to room temperature, 200 mL of water is added to the system, stirred thoroughly for 30 min, and filtered under reduced pressure. The filter cake is washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid; the crude product is slurried once with n-heptane, dissolved with 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, a white solid R-3 (13.45 g, yield 64%) is obtained.

[0180] Synthesis of Sub-c1:

[0181]

[0182] Under nitrogen atmosphere, add Sub-b1 (20g, 58.1mmol), raw material R-1 (CAS: 116233-18-2, 18.1g, 58.1mmol), tetrakis(triphenylphosphine)palladium (0.67g, 0.58mmol), anhydrous potassium carbonate (12.0g, 87.2mmol), tetrabutylammonium bromide (0.4g, 1.2mmol), toluene (160mL), anhydrous ethanol (80mL) and deionized water (40mL) to a 1000mL three-necked flask in sequence, start stirring and heating, and heat to reflux for 16h. After the system is cooled to room temperature, extract with dichloromethane (100mL×3 times), combine the organic phases and dry with anhydrous sodium sulfate, filter and remove the solvent by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-c1 (19.6 g, yield 75%).

[0183] Referring to the synthesis method of Sub-c1, reactant C shown in Table 1 was used to replace Sub-b1, and the remaining raw materials and steps were the same to synthesize intermediates Sub-c2 to Sub-c18.

[0184] Table 1: Synthesis of Sub-c2 to Sub-c18

[0185]

[0186]

[0187]

[0188]

[0189] Synthesis of Sub-d1:

[0190]

[0191] Under nitrogen atmosphere, add Sub-c1 (20.0 g, 44.5 mmol), triphenylphosphine (29.2 g, 111.2 mmol) and o-dichlorobenzene (200 mL) to a 250 mL three-necked flask, start stirring and heating, and heat to reflux for 16 h. After the system is cooled to room temperature, the solvent is removed by vacuum distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a gray-green solid intermediate Sub-d1 (9.3 g, yield 50%).

[0192] Referring to the preparation method of Sub-d1, the reactant D structure shown in Table 2 was used to replace Sub-c1 to synthesize intermediates Sub-d2 to Sub-d39.

[0193] Table 2: Synthesis of Sub-d2 to Sub-d39

[0194]

[0195]

[0196]

[0197]

[0198] Synthesis of compound 366:

[0199]

[0200] Under nitrogen atmosphere, Sub-d1 (10.0 g, 23.9 mmol), R-2 (CAS: 142475-00-1 (5.8 g, 23.9 mmol), tris(dibenzylideneacetone)dipalladium (0.22 g, 0.24 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (SPhos, 0.19 g, 0.48 mmol), sodium tert-butoxide (3.4 5g, 35.9mmol) and xylene (120mL), heated to reflux, stirred and reacted overnight. After the system was cooled to room temperature, it was extracted with dichloromethane (100mL×3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered and then distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of n-heptane / dichloromethane as the mobile phase to obtain a white solid 366 (9.7g; yield 70%, m / z=579.3[M+H] + ).

[0201] Referring to the synthesis of compound 366, the reactant K shown in Table 3 was used to replace Sub-d1, and the reactant L was used to replace the raw material R-2 to synthesize the compounds of the present application in Table 3 below:

[0202] Table 3: Synthesis of some compounds in this application

[0203]

[0204]

[0205]

[0206] Synthesis of compound 329:

[0207]

[0208] Under nitrogen atmosphere, Sub-d1 (10 g, 23.9 mmol), 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (12.4 g, 35.9 mmol) and dry DMF (100 mL) were added to a 500 mL three-necked flask in sequence, the system was cooled to -10 ° C, sodium hydrogen (1.26 g, 53 mmol) was quickly added, and the reaction was stirred overnight. The reaction solution was poured into 200 mL of deionized water, stirred for 30 min, filtered and the filtered solid was taken, the filtered solid was washed with deionized water until neutral, and then rinsed with anhydrous ethanol (200 mL) to obtain a crude product; the crude product was purified by silica gel column chromatography using a mixed solvent of n-heptane / dichloromethane as the mobile phase to obtain a white solid compound 329 (12.1 g, yield 70%, m / z=725.3 [M+H] + ).

[0209] Referring to the synthesis of compound 329, reactant M shown in Table 4 was used to replace Sub-d1, and reactant N was used to replace 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine to synthesize the compounds of the present application in Table 4.

[0210] Table 4: Synthesis of some compounds in this application

[0211]

[0212]

[0213]

[0214]

[0215] Compound 366: 1 H-NMR(400MHz,CD2Cl2)δppm 8.62(s,1H),8.08(d,1H),8.05(d,1H),7.95(d,1H),7.67-7.64(m,2H),7.53(s,1H), 7.47(s,1H),7.45(s,1H),7.40-7.39(m,1H),1.82(s,4H),1.30(s,6H),1.27(s,6H).

[0216] Compound 329: 1H-NMR(400MHz,CD2Cl2)δppm9.07(s,1H),8.55(d,2H),8.37(d,2H),8.09(s,1H),8.07(d,1H),8.05(d,1H),7.96-7.93 (m,3H),7.83(s,1H),7.67-7.65(m,3H),7.59-7.51(m,7H),7.45-7.36(m,2H),1.80(s,4H),1.31(s,6H),1.29(s,6H).

[0217] Preparation and evaluation of organic electroluminescent devices:

[0218] Example 1: Red organic electroluminescent device

[0219] The anode was prepared by the following process: ITO / Ag / ITO with a thickness of The ITO substrate is cut into a size of 40 mm (length) × 40 mm (width) × 0.5 mm (thickness), and is prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface can be treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate can be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0220] HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a layer with a thickness of Then, NPB is vacuum evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer is formed by a plurality of holes.

[0221] Compound HT-1 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is formed by a plurality of holes.

[0222] Next, on the second hole transport layer, compound 358:Ir(piq)2acac was co-evaporated at an evaporation rate ratio of 97%:3% to form a layer with a thickness of The red light emitting layer (EML)

[0223] On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0224] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the manufacture of the red organic electroluminescent device.

[0225] Embodiments 2 to 28

[0226] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound X in the following Table 1 was used instead of the compound 358 in Example 1 when preparing the light-emitting layer.

[0227] Comparative Examples 1 to 3

[0228] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 358 in Example 1 respectively when preparing the light-emitting layer.

[0229] Among them, in each embodiment and comparative example, the compound structure used is as follows:

[0230]

[0231] The performance of the red organic electroluminescent devices prepared in Examples 1 to 28 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T 95 Device life at 30mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 5.

[0232] Table 5

[0233]

[0234]

[0235] Referring to Table 1 above, it can be seen that the performance of the organic electroluminescent devices of Examples 1 to 28 is greatly improved compared with the organic electroluminescent devices of Comparative Examples 1 to 3. Specifically, the operating voltage of the device is reduced by at least 0.1V, the luminous efficiency is increased by at least 16.9%, and the T95 life is greatly increased by at least 17.1%.

[0236] Example 29: Red organic electroluminescent device

[0237] The anode was prepared by the following process: ITO / Ag / ITO with a thickness of The ITO substrate is cut into a size of 40 mm (length) × 40 mm (width) × 0.5 mm (thickness), and is prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface can be treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate can be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0238] HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a Then, NPB is vacuum-evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer is formed by a plurality of holes.

[0239] Compound HT-1 is vacuum-evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is formed by a plurality of holes.

[0240] Next, on the second hole transport layer, compound 366: RH-1: Ir(piq)2acac was co-evaporated at an evaporation rate ratio of 48%: 48%: 4% to form a layer with a thickness of The red light emitting layer (EML)

[0241] The vacuum evaporation compound and LiQ are mixed in a weight ratio of 1:1 and evaporated on the light-emitting layer to form Thick electron transport layer.

[0242] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0243] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the manufacture of the red organic electroluminescent device.

[0244] Examples 30 to 46

[0245] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound Y in the following Table 2 was used instead of compound 366 in Example 29 when preparing the light-emitting layer.

[0246] Comparative Examples 4 to 6

[0247] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound D, compound E and compound F were used to replace compound 366 in Example 1 respectively when preparing the light-emitting layer.

[0248] Among them, in Examples 29 to 46 and Comparative Examples 4 to 6, the structures of the compounds used are as follows:

[0249]

[0250] The performance of the red organic electroluminescent devices prepared in Examples 29 to 46 and Comparative Examples 4 to 6 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 30mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 6.

[0251] Table 6

[0252]

[0253]

[0254] Referring to Table 6 above, it can be seen that the performance of the organic electroluminescent devices of Examples 29 to 46 is greatly improved compared to the organic electroluminescent devices of Comparative Examples 4 to 6. Specifically, the operating voltage of the device is similar, but the luminous efficiency is at least increased by 15.2%, and the T95 life is greatly increased by at least 19.5%.

[0255] The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

1. An organic compound, characterized in that It has a structure shown in the following Formula 1: Ring A is selected from a benzene ring, a naphthalene ring or a phenanthrene ring; X is selected from O, S, C(R4R5); R4 and R5 are each independently selected from an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or R4 and R5 are connected to each other and form a ring with the carbon atom to which they are connected; W is selected from the structure shown in formula a-1 or the structure shown in formula a-2; L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; The substituents in L, L1, L2, L3, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, and optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms; n1 is selected from 0, 1 or 2; when n1 is greater than, each R1 is the same or different; n2 is selected from 0, 1 or 2; when n2 is greater than, each R2 is the same or different; optionally, adjacent R2 forms a benzene ring; n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n3 is greater than, each R3 is the same or different.

2. The organic compound according to claim 1, wherein Each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl; optionally, any two adjacent R2 form a benzene ring.

3. The organic compound according to claim 1, wherein R4 and R5 are the same or different and are independently selected from trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, or R4 and R5 are connected to each other and form a fluorene ring, cyclopentane or cyclohexane with the carbon atom to which they are connected.

4. The organic compound according to claim 1, wherein L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; Optionally, the substituents in L, L1, L2 and L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group.

5. The organic compound according to claim 1, wherein L, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group; Optionally, the substituents in L, L1, L2 and L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

6. The organic compound according to claim 1, wherein Het is selected from the following groups: -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In the above formula, L2 is a single bond and Ar2 is hydrogen.

7. The organic compound according to claim 1, wherein Het is selected from the following groups: -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In the above formula, L2 is a single bond and Ar2 is hydrogen.

8. The organic compound according to claim 1, wherein Ar1 and Ar3 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms; Ar2 is selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms; Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

9. The organic compound according to claim 1, wherein Ar1 and Ar3 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzimidazolyl; Optionally, Ar2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1, Ar2 and Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl.

10. The organic compound according to claim 1, wherein Ar1 is selected from the following groups: Optionally, Ar2 is selected from the following groups: Optionally, Ar3 is selected from the following groups:

11. The organic compound according to claim 1, wherein Selected from the group consisting of:

12. The organic compound according to claim 1, wherein Selected from the group consisting of:

13. The organic compound according to claim 1, wherein The organic compound is selected from the group consisting of the following compounds:

14. 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; characterized in that: The functional layer comprises the organic compound according to any one of claims 1 to 13; Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the organic compound.

15. An electronic device, characterized in that The organic electroluminescent device according to claim 14 is included.

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