Organic compounds, organic electroluminescent devices and electronic devices comprising the same

Abstract

The present application relates to an organic compound, an organic electroluminescence device comprising the same, and an electronic device. The structural formula of the organic compound of the present application comprises a structure shown in formula I, and the application of the organic compound in an organic electroluminescence device can significantly improve the performance of the device.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic materials, and particularly relates to an organic compound, an organic electroluminescent device containing the same, and an electronic device. BACKGROUND

[0002] At present, an organic electroluminescent device (OLED) is considered as the next generation display and lighting technology due to the advantages of active light-emitting, high light-emitting efficiency, low power consumption, lightness, thinness, fast response speed, and large viewing angle. The organic electroluminescent device generally comprises a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move to the electroluminescent layer, and holes on the anode side also move to the electroluminescent layer. The electrons and the holes combine to form excitons in the electroluminescent layer. The excitons in the excited state release energy to the outside, and then the electroluminescent layer emits light.

[0003] The organic electroluminescent device can be of various structures, such as a single-layer structure and a stacked structure. The single-layer organic electroluminescent device comprises only one light-emitting unit between the cathode and the anode, and the stacked organic electroluminescent device is stacked by multiple light-emitting units. One light-emitting unit generally comprises at least one light-emitting layer, one hole transport layer, and one electron transport layer. On this basis, the light-emitting unit can further comprise a hole injection layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. There is a charge generation layer (CGL) between adjacent light-emitting units for the generation and movement of charges. The CGL is constructed in the form of p-n, comprising an n-type charge generation layer (n-CGL) and a p-type charge generation layer (p-CGL). Among them, the p-type material mainly generates holes, and the n-type material is doped with a low work function metal through an electron transport layer material to generate electrons.

[0004] The most important problems in the existing organic electroluminescent device are the service life and the efficiency. With the large-area display, the voltage is also increased. Therefore, it is necessary to continue to develop new materials to further improve the performance of the organic electroluminescent device. SUMMARY

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

[0006] The first aspect of the present application provides an organic compound having the structure shown in Formula I:

[0007]

[0008] wherein Q1 is Q2 is

[0009] each R is independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having a carbon number of 1-10, a haloalkyl group having a carbon number of 1-10, a deuterated alkyl group having a carbon number of 1-10, an aryl group having a carbon number of 6-12, or a deuterated aryl group having a carbon number of 6-12;

[0010] n represents the number of R, and n is selected from 0, 1, 2, or 3; when n is greater than 1, any two R are the same or different; optionally, any two adjacent R form a benzene ring;

[0011] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon number of 6-30, or a substituted or unsubstituted heteroaryl group having a carbon number of 3-30;

[0012] L a , L b , L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having a carbon number of 6-30, or a substituted or unsubstituted heteroarylene group having a carbon number of 3-30; and at least one of L a , L b , L1and L2is not a single bond;

[0013] Ar1, Ar2, L a , L b , L1and L2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon number of 1-10, a haloalkyl group having a carbon number of 1-10, a deuterated alkyl group having a carbon number of 1-10, a trialkylsilyl group having a carbon number of 3-12, a deuterated aryl group having a carbon number of 6-12, an aryl group having a carbon number of 6-20, or a heteroaryl group having a carbon number of 3-20;

[0014] provided that at least one of Ar1, Ar2, L a , L b , L1and L2contains a nitrogen-containing heteroaryl group, and the nitrogen-containing heteroaryl group has 1, 2, or 3 unsaturated nitrogen atoms.

[0015] A second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound described above.

[0016] A third aspect of the present application provides an electronic device comprising the organic electroluminescent device of the second aspect.

[0017] The compounds of this application are based on isoquinoline and pyridine as their cores. Nitrogen-containing heteroaryl groups are further introduced to expand the molecular conjugation range and effectively adjust the intermolecular stacking, thereby improving electron mobility and reducing device voltage. Furthermore, the compounds of this application have excellent metal complexing ability. They can form stable N-metal coordination bonds with metals such as Li and Yb, effectively inhibiting metal oxidation and improving charge generation efficiency. This, in turn, increases luminous efficiency and extends the service life of organic electroluminescent devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] 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.

[0019] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to one embodiment of the present application.

[0020] Figure 2 It is a schematic structural diagram of an organic electroluminescent device according to another embodiment of the present application.

[0021] Figure 3 It is a schematic structural diagram of an electronic device according to one embodiment of the present application.

[0022] Reference numerals

[0023] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0024] 321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer

[0025] 350, electron injection layer 411, first hole transport layer 412, first hole adjustment layer 413, first light-emitting layer

[0026] 414, first electron transport layer 421, n-type charge generation layer 422, p-type charge generation layer 431, second hole transport layer

[0027] 432, second hole adjustment layer 433, second light-emitting layer 434, second electron transport layer 410, first light-emitting unit

[0028] 420, charge generation layer 430, second light emitting unit 500. Electronic devices DETAILED DESCRIPTION

[0029] Example implementations will now be described more fully with reference to the accompanying drawings. Example implementations, however, can be implemented in many different forms and should not be construed as limited to the examples set forth herein; rather, these examples are provided so that this disclosure will be thorough and complete, and will fully convey the scope of example implementations to those skilled in the art. The described features, structures, or characteristics can be combined in one or more implementations. In the following description, numerous specific details are provided to give a thorough understanding of example implementations.

[0030] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0031]

[0032] wherein Q1is Q2is

[0033] each R is independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having a carbon number of 1-10, a haloalkyl group having a carbon number of 1-10, a deuterated alkyl group having a carbon number of 1-10, an aryl group having a carbon number of 6-12, or a deuterated aryl group having a carbon number of 6-12;

[0034] n represents the number of R, and n is selected from 0, 1, 2, or 3; when n is greater than 1, any two R are the same or different; optionally, any two adjacent R form a benzene ring;

[0035] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon number of 6-30, or a substituted or unsubstituted heteroaryl group having a carbon number of 3-30;

[0036] L a , L b , L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having a carbon number of 6-30, or a substituted or unsubstituted heteroarylene group having a carbon number of 3-30; and L a , L b , at least one of L a , L b , the substituents in Ar1, Ar2, L a , L b , L1and L2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon number of 1-10, a haloalkyl group having a carbon number of 1-10, a deuterated alkyl group having a carbon number of 1-10, a trialkylsilyl group having a carbon number of 3-12, a deuterated aryl group having a carbon number of 6-12, an aryl group having a carbon number of 6-20, or a heteroaryl group having a carbon number of 3-20;

[0038] The condition is that Ar1, Ar2, L a , L b At least one of L1 and L2 contains a nitrogen-containing heteroaryl group, and the nitrogen-containing heteroaryl group has 1, 2 or 3 unsaturated nitrogen atoms.

[0039] In this 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 R forms a benzene ring" includes: the scenario where any two adjacent R form a benzene ring, and the scenario where any two adjacent R form a benzene ring. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms each having one substituent; 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 each of two adjacent atoms, the two substituents can be fused into a ring.

[0040] In this application, the descriptions used in this application are interchangeable with "each ... independently is" and "... are respectively independently" and "... are each independently" and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, " ", wherein each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents 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 represents 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.

[0041] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease 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 aryl group without a substituent. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, etc. The number of substituents can be one or more.

[0042] In the present application, a group may be a monovalent group or a multivalent group formed by substitution.

[0043] In this application, "plurality" refers to two or more, for example, 2, 3, 4, 5, 6, etc.

[0044] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0045] 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).

[0046] “D” in the structural formula of the compound of the present application represents deuteration.

[0047] 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 (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, two or more condensed ring aryl groups connected by carbon-carbon bond. That is, unless otherwise stated, two or more aromatic groups connected by carbon-carbon bond can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Examples of aryl include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, perylene, benzo [9,10] phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0048] In the present application, "arylene group" refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0049] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, or 30.

[0050] In this application, Ar1, Ar2, L a 、L b The aryl groups of the substituents of L1 and L2 are exemplified but not limited to phenyl, naphthyl, phenanthrenyl, biphenyl and the like.

[0051] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. For 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 triazinyl 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 silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0052] 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.

[0053] In the present application, the number of carbon atoms in 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, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.

[0054] In this application, Ar1, Ar2, L a 、L b The heteroaryl groups of the substituents of L1 and L2 are exemplified but not limited to triazinyl, pyridyl, quinolyl, isoquinolyl and the like.

[0055] 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 a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a deuterated alkyl group, a halogenated alkyl group, or the like.

[0056] 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 in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. 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, and n-hexyl.

[0057] In the present application, a halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0058] In the present application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0059] In the present application, the number of carbon atoms of a deuterated alkyl group having 1 to 10 carbon atoms 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, trideuteromethyl.

[0060] In the present application, the number of carbon atoms of a halogenated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of halogenated alkyl groups include, but are not limited to, trifluoromethyl.

[0061] In the present application, specific examples of deuterated aryl groups include, but are not limited to, penta-deuterophenyl.

[0062] In the present application, denotes a chemical bond to which other groups are attached.

[0063] In the present application, an indefinite position connection bond refers to a single bond "— " extending from a ring system , which indicates that one end of the connection bond can be connected to any position in the ring system through which the bond passes, and the other end is connected to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions in the molecule through two indefinite position connection bonds that pass through the bicyclic ring, and the meaning represented thereby includes any possible connection mode as shown in formulae (f-1) to (f-10).

[0064]

[0065] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions in the molecule through one indefinite position connection bond extending from the middle of one of the benzene rings, and the meaning represented thereby includes any possible connection mode as shown in formulae (X'-1) to (X'-4).

[0066]

[0067] In the present application, an indefinite position substituent refers to a substituent connected through a single bond extending from the center of a ring system, which indicates 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 one indefinite position connection bond, and the meaning represented thereby includes any possible connection mode as shown in formulae (Y-1) to (Y-7).

[0068]

[0069] In this application, regarding Ar1, Ar2, L a , L b Any limitation of Ar1, Ar2, L1 and L2 is made under the following premise: a , L b At least one of L1 and L2 contains a nitrogen-containing heteroaryl group, and the nitrogen-containing heteroaryl group has 1, 2 or 3 unsaturated nitrogen atoms.

[0070] More specifically, the compound of formula I of the present application satisfies the following conditions: a , L b At least one of L1 and L2 contains a specific nitrogen-containing heteroaryl group (subunit): pyridine, pyrimidine, pyrazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, acridine, phenazine, dibenzo[C,H]acridine, phenanthroline, benzoxazole, benzofuro[3,2-c]pyridine, benzofuro[2,3-c]pyridine, benzofuro[2,3-b]pyridine. In the compounds of the present application, Ar1, Ar2, L a , L b At least one group among L1 and L2 is selected from the listed substituted or unsubstituted specific nitrogen-containing heteroaryl groups (subunits), and the listed nitrogen-containing heteroaryl groups all contain 1, 2 or 3 unsaturated nitrogen atoms. This can make the compound as a whole have a more suitable metal complexing ability, ensure that the material can have better electron mobility in the device, and can effectively inhibit metal oxidation, thereby improving the luminescence characteristics of the device.

[0071] Furthermore, the compound of formula I of the present application satisfies the following conditions: a , L b , L1 and L2: at least one of Ar1 and Ar2 is selected from the following substituted or unsubstituted groups V1, and the unsubstituted group V1 is selected from the group consisting of the following groups:

[0072]

[0073] or L a , L b At least one of L1 and L2 is selected from a substituted or unsubstituted group V 2， The unsubstituted group V2 is selected from the group consisting of:

[0074]

[0075] The substituted groups V1 and V2 have one or more substituents, and the substituents of the substituted groups V1 and V2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1-10 carbon atoms, a haloalkyl group having 1-10 carbon atoms, a deuterated alkyl group having 1-10 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, a deuterated aryl group having 6-12 carbon atoms, an aryl group having 6-20 carbon atoms, or a heteroaryl group having 3-20 carbon atoms. When the number of the substituents is greater than 1, the substituents are the same or different.

[0076] In some embodiments of the present application, each R is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl; n represents the number of R, and n is selected from 0, 1, 2 or 3; when n is greater than 1, any two Rs are the same or different; optionally, any two adjacent Rs form a benzene ring; that is, any two adjacent Rs may form a benzene ring or may not form a benzene ring.

[0077] In some embodiments of the present application, Q1 is And L a and L1 are selected from single bonds; Q2 is And L b At least one of L and L2 is not a single bond.

[0078] In some embodiments of the present application, Q1 is And L a and L1 is not a single bond; Q2 is And L b and L2 are both selected from single bonds.

[0079] In the present application, Ar1 and Ar2 are the same or different and can be independently 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, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0080] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 21 carbon atoms;

[0081] Optionally, each of the substituents in Ar1and Ar2is independently selected from the group consisting of deuterium, fluorine, cyano, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbon atoms, deuterated alkyl of 1 to 5 carbon atoms, trialkylsilyl of 3 to 7 carbon atoms, deuterated aryl of 6 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, heteroaryl of 3 to 9 carbon atoms;

[0082] provided that at least one of Ar1and Ar2is selected from the group consisting of the following substituted or unsubstituted groups V a b at least one of L1and L2is selected from the group consisting of the following substituted or unsubstituted groups V

[0083] In some embodiments of the present application, Ar1and Ar2are the same or different, and each is independently selected from the group consisting of substituted or unsubstituted groups W, wherein the unsubstituted groups W are selected from the group consisting of:

[0084]

[0085] wherein the substituted groups W have one or more than one substituents, each of which is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazinyl, pyridyl, quinolinyl, or isoquinolinyl; and when the number of substituents is more than one, each substituent is the same or different;

[0086] provided that at least one of Ar1and Ar2is selected from the group consisting of the following substituted or unsubstituted groups V 1， the unsubstituted groups V1are selected from the group consisting of:

[0087]

[0088] or L a b at least one of L1and L2is selected from the group consisting of the following substituted or unsubstituted groups V 2， the unsubstituted groups V2are selected from the group consisting of:

[0089]

[0090] ​​and substituted groups V1and V2have one or two or more substituents each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazinyl, pyridyl, quinolinyl, or isoquinolinyl; and when the number of substituents is more than one, each substituent is the same or different.

[0091] In some embodiments of the present application, Ar1and Ar2are the same or different and each is independently selected from the group consisting of:

[0092]

[0093]

[0094] provided that when L a , L b , L1and L2are each independently selected from a single bond, substituted or unsubstituted phenylene, biphenylene, naphthylene, anthrylene, phenanthrylene, pyrenylene, at least one of Ar1and Ar2is selected from the group consisting of:

[0095]

[0096]

[0097] In some embodiments of the present application, Ar1and Ar2are the same or different and each is independently selected from the group consisting of:

[0098]

[0099]

[0100] In the present application, L a , L b , L1and L2are the same or different and can each be independently selected from a single bond, substituted or unsubstituted arylene having a carbon number of 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, substituted or unsubstituted heteroarylene having a carbon number of 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, or 30; and at least one of L a , L b , L1and L2is not a single bond.

[0101] In some embodiments of the present application, La L b L1and L2are the same or different and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 16 carbon atoms, a substituted or unsubstituted heteroarylene group having 4 to 24 carbon atoms; and L a L b at least one of L1and L2is not a single bond;

[0102] L a L b each substituent in L1and L2is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazinyl, pyridyl, quinolyl or isoquinolyl;

[0103] provided that at least one of Ar1and Ar2is selected from a substituted or unsubstituted group V a L b at least one of L1and L2is selected from a substituted or unsubstituted group V

[0104] In some embodiments of the present application, L a L b L1and L2are the same or different and each is independently selected from a single bond, a substituted or unsubstituted group U, and L a L b at least one of L1and L2is not a single bond, wherein the unsubstituted group U is selected from the group consisting of:

[0105]

[0106] wherein the substituted group U has one or more than one substituent, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazinyl, pyridyl, quinolyl or isoquinolyl, and when the number of the substituents is more than one, each substituent is the same or different;

[0107] provided that at least one of Ar1and Ar2is selected from a substituted or unsubstituted group V 1，the unsubstituted group V1is selected from the group consisting of

[0108]

[0109] or L a , L b , at least one of L1and L2is selected from the group consisting of a substituted or unsubstituted group V 2， the unsubstituted group V2is selected from the group consisting of

[0110]

[0111] and substituted groups V1and V2have one or two or more substituents each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, iso-propyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazinyl, pyridyl, quinolinyl or isoquinolinyl; the number of substituents being more than one, the substituents being identical or different.

[0112] In some embodiments of the application, L a , L b , L1and L2are identical or different and each independently selected from the group consisting of a single bond or a , L b , at least one of L1and L2is not a single bond;

[0113]

[0114]

[0115] provided that when Ar1and Ar2are each independently selected from the group consisting of a substituted or unsubstituted phenylene, biphenylene, naphthylene, anthrylene, phenanthrylene, pyrylene, triphenylylene, pyridylene, quinolinylene or isoquinolinylene, at least one of L a , L b , L1and L2are identical or different and each independently selected from the group consisting of a single bond or

[0116] In some embodiments, L a and L b are selected from the group consisting of a single bond or

[0117]

[0118] L1and L2are each independently selected from the group consisting of a single bond or

[0119]

[0120] And L a , L b At least one of L1 and L2 is not a single bond.

[0121] In some embodiments of the present application, L a , L b , L1 and L2 are the same or different and are each independently selected from a single bond or the following groups, and L a , L b At least one of L1 and L2 is not a single bond

[0122]

[0123] In some embodiments of the present application, Q1 is selected from the group consisting of:

[0124]

[0125] Q2 is selected from the group consisting of:

[0126]

[0127]

[0128]

[0129] In some embodiments of the present application, Q2 is selected from the group consisting of:

[0130] Q1 is selected from the group consisting of:

[0131]

[0132]

[0133] In some embodiments of the present application, the compound of the present application is selected from the structure shown in the following formula Ia or Ib:

[0134]

[0135] In the above formula Ia, each R is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuteromethyl, phenyl, pentadeuterophenyl or naphthyl.

[0136] In the present application, compared with the compound represented by Formula Ia, the compound represented by Formula Ib has a higher degree of structural conjugation and a faster carrier mobility.

[0137] In some embodiments of the application, in the above formula I-a, Q1 is and L a and L1 are each selected from a single bond; Q2 is and L b at least one of L and L2 is other than a single bond.

[0138] In some embodiments of the application, in the above formula I-a, Q1 is selected from the group consisting of:

[0139]

[0140] Q2 is selected from the group consisting of:

[0141]

[0142]

[0143]

[0144] In some embodiments of the application, in the above formula I-a, Q1 is and L a at least one of L and L1 is other than a single bond; Q2 is and L b and L2 are each selected from a single bond.

[0145] In some embodiments of the application, in the above formula I-a, Q2 is selected from the group consisting of:

[0146]

[0147] Q1 is selected from the group consisting of:

[0148]

[0149]

[0150]

[0151] In some embodiments of the application, in the above formula I-b, Q1 is and L a and L1 are each selected from a single bond; Q2 is and L b at least one of L and L2 is other than a single bond.

[0152] In some embodiments of the application, in the above formula I-b, Q1 is selected from the group consisting of:

[0153]

[0154] Q2is selected from the group consisting of:

[0155]

[0156]

[0157] Optionally, the organic compound is selected from the group consisting of:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] The second aspect of the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound described in the present application.

[0177] In an embodiment of the present application, the functional layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer. The electron transport layer comprises the organic compound described in the present application.

[0178] In an embodiment of the present application, the structure of the organic electroluminescent device is as shown in Figure 1 The functional layer 300 comprises a hole injection layer 310, a hole transport layer 321, a hole adjustment layer 322, a light emitting layer 330, an electron transport layer 340 and an electron injection layer 350, wherein the electron transport layer 340 comprises the organic compound described in the present application.

[0179] In the present application, the anode 100 comprises an anode material, which is optionally a material with large work function that facilitates hole injection into the functional layer. Specific examples of the anode material 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); combined metal and oxide 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. Optionally, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0180] In the present application, the hole injection layer 310 can be selected from diphenylamine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 is selected, for example, from the following compounds or any combination thereof.

[0181]

[0182] In an embodiment of the present application, the hole injection layer 310 is composed of HT-1 and NDP-9.

[0183] In some embodiments of the present application, the hole transport material can be selected from triarylamine compounds or other types of compounds, which can be selected by those skilled in the art with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of the following compounds.

[0184]

[0185] In an embodiment of the present application, the material of the hole transport layer 321 comprises HT-1.

[0186] In one embodiment of the present application, the electron blocking layer 322 comprises one or more electron blocking materials, which can be selected from carbazole polymers or other types of compounds, without specific limitation. For example, in some embodiments of the present application, the electron blocking layer 322 is composed of a compound EB-1 .

[0187] Optionally, the light-emitting layer material can be composed of a single light-emitting material, or can comprise a host material and a guest material

[0188] In one embodiment of the present application, the light-emitting layer 330 is composed of a host material and a guest material

[0189] Optionally, the host material of the light-emitting layer 330 can comprise a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. The host material of the organic light-emitting layer 330 can be a compound, a combination of two or more compounds.

[0190] In one embodiment of the present application, the host material of the organic light-emitting layer 330 is BH-1

[0191] In one specific embodiment of the present application, the guest material of the light-emitting layer 330 is BD-1

[0192] In the present application, the electron injection layer 350 can comprise inorganic materials such as alkali metal sulfides, alkali metal halides, or can comprise complexes of alkali metals and organic materials. In one embodiment of the present application, the electron injection layer 350 comprises Yb.

[0193] In the present application, the cathode 200 comprises a cathode material, which is a material with small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material 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 multi-layered materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.

[0194] Further, the present application also provides another organic electroluminescent device as Figure 2 shown in FIG. 2, which comprises an anode and a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises a first light-emitting unit, a second light-emitting unit, and a charge generation layer; and the charge generation layer comprises an organic compound described in the present application. The Figure 2The organic electroluminescent device shown below is also referred to as a stacked organic electroluminescent device.

[0195] In an embodiment of the present application, the stacked organic electroluminescent device comprises an anode 100, a cathode 200, a hole injection layer 310, an electron injection layer 350, a first light-emitting unit 410, a second light-emitting unit 430, and a charge generation layer 420. The first light-emitting unit 410, the second light-emitting unit 430, and the charge generation layer 420 are located between the anode 100 and the cathode 200, the charge generation layer 420 is located between the first light-emitting unit 410 and the second light-emitting unit 430, and the charge generation layer 420 comprises an organic compound described in the present application.

[0196] In an embodiment of the present application, the first light-emitting unit 410 comprises a first hole transport layer 411, a first hole adjustment layer 412, a first light-emitting layer 413, and a first electron transport layer 414; and the second light-emitting unit 430 comprises a second hole transport layer 431, a second hole adjustment layer 432, a second light-emitting layer 433, and a second electron transport layer 434.

[0197] In an embodiment of the present application, the charge generation layer 420 comprises an n-type charge generation layer (n-CGL) 421 and a p-type charge generation layer (p-CGL) 422, the n-type charge generation layer 421 provides electrons to the first electron transport layer 414 of the first light-emitting unit 410, and the p-type charge generation layer 422 provides holes to the second hole transport layer 431 of the second light-emitting unit 430. In an embodiment of the present application, the n-type charge generation layer comprises an organic compound described in the present application.

[0198] In an embodiment of the present application, the n-type charge generation layer is composed of an organic compound described in the present application and a metal-doped material. Optionally, the metal-doped material is Li, Ca, Ag, Cs, or Yb.

[0199] In an embodiment of the present application, the p-CGL layer comprises HT-1 and NDP-9

[0200] In the present application, the anode 100 comprises an anode material, which optionally comprises indium tin oxide (ITO).

[0201] In an embodiment of the present application, the hole injection layer 310 is composed of HT-1 and NDP-9.

[0202] In an embodiment of the present application, the materials of the first hole transport layer 411 and the second hole transport layer 431 comprise HT-1.

[0203] In an embodiment of the present application, the material of the first hole adjustment layer 412 and the second hole adjustment layer 432 comprises RP-1

[0204] In the present application, the first light-emitting layer of the first light-emitting unit; and the second light-emitting layer of the second light-emitting unit, each can comprise the same or different host material and the same or different guest material.

[0205] In a specific embodiment of the present application, the host material of the first light-emitting layer 413 and the second light-emitting layer 433 is RH-1

[0206] In a specific embodiment of the present application, the guest material of the first light-emitting layer 413 and the second light-emitting layer 433 is RD-1

[0207] In a specific embodiment of the present application, the material of the first electron transport layer 414 and the second electron transport layer 434 comprises ET-1

[0208] In an embodiment of the present application, the electron injection layer 350 comprises Yb.

[0209] In a specific embodiment of the present application, the cathode 200 comprises a cathode material, and the cathode material comprises magnesium and silver.

[0210] The third aspect of the present application provides an electronic device comprising the organic electroluminescent device of the second aspect of the present application.

[0211] According to an embodiment, as shown in Figure 3 The electronic device provided can be an electronic device 500 comprising the organic electroluminescent device described above. The electronic device 500 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, electronic paper, an emergency lighting lamp, an optical module, and the like.

[0212] The synthesis method of the organic compound of the present application will be specifically described below in combination with the synthesis examples, but the present application is not limited in this way.

[0213] Synthesis Example

[0214] Synthesis of Intermediates

[0215] 1. Synthesis of Intermediate IMA-1

[0216]

[0217] After 1-chloro-3-phenylisoquinoline (15 g, 62.6 mmol) was dissolved in 1,4-dioxane, bis(pinacolato)diboron (19 g, 75.1 mmol), Pd(dppf)Cl2(0.9 g, 1.3 mmol) and potassium acetate (12.3 g, 125.2 mmol) were added. The reaction was stirred at 80°C for 4 hours under nitrogen atmosphere. After cooling to room temperature, the reaction was extracted with water and dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product, which was recrystallized with ethanol to obtain the intermediate IMA-1 (12.9 g, yield 62%).

[0218] 2. Synthesis of the intermediate IM B-X and the intermediate IM B-X-Y

[0219]

[0220] After 1-chloro-3-phenylisoquinoline (15 g, 62.6 mmol) was dissolved in 1,4-dioxane, bis(pinacolato)diboron (19 g, 75.1 mmol), Pd(dppf)Cl2(0.9 g, 1.3 mmol) and potassium acetate (12.3 g, 125.2 mmol) were added. The reaction was stirred at 80°C for 4 hours under nitrogen atmosphere. After cooling to room temperature, the reaction was extracted with water and dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product, which was recrystallized with ethanol to obtain the intermediate IMA-1 (12.9 g, yield 62%).

[0221] The intermediates IM B-2 to IM B-15 were prepared according to the synthesis method of the intermediate IM B-1, except that the starting material 2 was used instead of 1-chloro-3-phenylisoquinoline, and the starting material 3 / intermediate IMA-1 was used instead of 2-phenylpyridine-6-boronic acid pinacol ester, as shown in Table 1.

[0222] Table 1

[0223]

[0224]

[0225]

[0226] The intermediates IM B-2-1, IM B-3-1, IM B-3-2, IM B-8-1, IM B-11-1, IM B-12-1 were prepared according to the synthesis method of the intermediate IM B-1, except that the intermediate IM B-X was used instead of 1-chloro-3-phenylisoquinoline, and the starting material 4 was used instead of 2-phenylpyridine-6-boronic acid pinacol ester, as shown in Table 2.

[0227] Table 2

[0228]

[0229]

[0230] 3. Synthesis of intermediates IM C-X

[0231] Referring to the synthesis method of intermediate IM A-1, the difference is only that intermediate of intermediate IM B-X column is used instead of 1-chloro-3-phenylisoquinoline to prepare intermediate IM C-1 to intermediate IM C-5, which is shown in Table 3.

[0232] Table 3

[0233]

[0234]

[0235] Synthesis of compounds

[0236] Synthesis Example 1: Synthesis of compound 2

[0237]

[0238] Dissolve 2,6-dibromo-4-chloropyridine (5 g, 15.5 mmol) and intermediate IM A-1 (12.9 g, 38.8 mmol) in 30 mL of toluene, and then add tetrakis(triphenylphosphine)palladium (0.18 g, 0.16 mmol), K2CO3 (6.4 g, 46.6 mmol), 10 mL of ethanol, and 5 mL of water. Heat to reflux under a nitrogen atmosphere for 12 hours. After cooling to room temperature, stir in 100 mL of water for 30 minutes, and then suction filter, and rinse the filter cake with 100 mL of ethanol three times. Recrystallize the obtained solid with dichloromethane to obtain 5.1 g of compound 2 at a yield of 58%. m / z: 562.22 [M+H] + .

[0239] Synthesize the compounds in Table 4 by referring to the synthesis method of compound 2, except that raw material 5 / intermediate IM B-X is used instead of 2,6-dibromo-4-chloropyridine, and raw material 6 / intermediate of the intermediate IM C-X column is used instead of intermediate IM A-1; the raw material for synthesizing the compound, structure, yield, and mass spectrum are shown in Table 4.

[0240] Table 4

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] The compound nuclear magnetic data is shown in Table 5:

[0251] Table 5

[0252]

[0253] Example 1: Blue organic electroluminescent device

[0254] The anode was prepared by cutting an ITO / Ag / ITO substrate having a thickness of 1,100 A to a size of 40 mm (length) x 40 mm (width) x 0.7 mm (thickness), preparing it into an experimental substrate having a cathode, anode, and insulating layer pattern using a photolithography process, and performing surface treatment using UV ozone and O2:N2 plasma to increase the work function of the anode, and cleaning the ITO substrate surface with an organic solvent to remove impurities and oil on the ITO substrate surface.

[0255] Compound HT-1 and NDP-9 were co-evaporated on the experimental substrate (anode) in a thickness ratio of 98:2 to form a hole injection layer (HIL) having a thickness of 200 A, and then HT-1 was vacuum-evaporated on the hole injection layer to form a hole transport layer having a thickness of 200 A.

[0256] EB-1 was vacuum-evaporated on the hole transport layer to form an electron blocking layer having a thickness of 200 A.

[0257] Next, compound BH-1 (doped host) and compound BD-1 (doped guest) were co-evaporated on the hole adjustment layer in a ratio of 98:2 to form an emission layer (EML) having a thickness of 200 A.

[0258] Compound 2 and LiQ were mixed and evaporated on the emission layer in a thickness ratio of 1:1 to form a cathode having a thickness of 200 A. ​​​​​a thick electron transport layer (ETL), Yb was evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of then Mg and Ag were mixed at a ratio of 1:10 and evaporated on the electron injection layer to form a cathode with a thickness of

[0259] In addition, CP-1 was evaporated on the cathode to a thickness of thereby completing the manufacture of the green organic electroluminescent device.

[0260] Examples 2-7:

[0261] An organic electroluminescent device was prepared using the same method as Example 1, except that Compound 2 was replaced with the compounds in Table 7 below when forming the electron transport layer.

[0262] Comparative Examples 1-2

[0263] An organic electroluminescent device was prepared using the same method as Example 1, except that Compound 2 was replaced with Compound A, B in Table 6 below when forming the electron transport layer.

[0264] The main material structures used in the above examples and comparative examples are shown in Table 6.

[0265] Table 6

[0266]

[0267] The blue organic electroluminescent devices prepared in Examples 1-7 and Comparative Examples 1-2 were tested for performance, specifically the IVL performance of the devices was tested at 10 mA / cm 2 T 95 The device lifetime was tested at 15 mA / cm 2 The test results are shown in Table 7 below:

[0268] Table 7

[0269]

[0270]

[0271] As can be seen from Table 7 above, Examples 1-7 used the compounds of the present application as the electron transport layer material, compared with Comparative Examples 1-2, the voltage was reduced by at least 0.18 V, the luminous efficiency was increased by at least 12.7%, and the device lifetime was increased by at least 15.9%. It can be seen that using the organic compounds of the present application in the electron transport layer of an organic electroluminescent device can reduce the device voltage and improve the luminous efficiency and T 95 lifetime of the organic electroluminescent device.​

[0272] In order to further illustrate the application of the compound of the present application as a charge generation layer in a stacked organic electroluminescent device, the performance of the material of the present application is studied by constructing a stacked device.

[0273] Example 8: Red stacked organic electroluminescent device

[0274] 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) × 0.7 mm (thickness), and is prepared into an experimental substrate with a cathode overlap area, an anode, and an insulating layer pattern 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.

[0275] Compounds HT-1 and NDP-9 were co-evaporated on the experimental substrate (anode) at a thickness ratio of 98%:2% to form a A hole injection layer (HIL) was formed, and HT-1 was vacuum evaporated on the hole injection layer to form a thickness of hole transport layer.

[0276] RP-1 was vacuum-deposited on the hole transport layer to form a layer with a thickness of The first hole adjustment layer (prime-1) is formed.

[0277] Next, compound RH-1 and compound RD-1 were co-evaporated on the first hole adjustment layer at a thickness ratio of 98%:2% to form a layer with a thickness of a first emitting layer (EML) of the present invention.

[0278] On the first light-emitting layer, compound ET-1 and LiQ were co-deposited at a thickness ratio of 1:1 to form A thick first electron transport layer (ETL).

[0279] The above is the first light-emitting unit.

[0280] Next, compound 2 and Yb were co-evaporated on the electron transport layer at a thickness ratio of 99%:1% to form a layer with a thickness of The n-type charge generation layer (n-CGL) is then co-evaporated with compounds HT-1 and NDP-9 at a thickness ratio of 95%:5% to form a layer with a thickness of p-type charge generation layer (p-CGL).

[0281] The above is the charge generation layer (CGL).

[0282] On the p-type charge generation layer, HT-1 was evaporated to form a second hole transport layer having a thickness of 50 A, and RP-1 was vacuum evaporated on the second hole transport layer to form a second hole adjustment layer (prime-2) having a thickness of 50 A.

[0283] Next, on the second hole transport layer, compound RH-1 and compound RD-1 were co-evaporated at a thickness ratio of 98%:2% to form a second light emitting layer (EML-2) having a thickness of 200 A.

[0284] On the second light emitting layer, compound ET-1 and LiQ were co-evaporated at a thickness ratio of 1:1 to form a second electron transport layer (ETL-2) having a thickness of 200 A.

[0285] The above is the second light emitting unit.

[0286] Finally, Yb was evaporated on the electron transport layer to form an electron injection layer (EIL) having a thickness of 50 A, and then magnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1:9 and vacuum evaporated on the electron injection layer to form a cathode having a thickness of 200 A.

[0287] In addition, CP-1 having a thickness of 200 A was vacuum evaporated on the above cathode to form an organic cover layer (CPL), thereby completing the manufacture of a red stacked organic electroluminescent device. Examples 9-60:

[0288] An organic electroluminescent device was prepared using the same method as in Example 8, except that in preparing the n-type charge generation layer, the compound 2 in Example 8 was replaced with the compounds in Table 9.

[0289] Comparative Examples 3-6

[0290] An organic electroluminescent device was prepared using the same method as in Example 8, except that in preparing the n-type charge generation layer, the compound 2 in Example 8 was replaced with the compounds C, D, E, F in Table 8.

[0291] In preparing the organic electroluminescent device, the structures of the respective materials used in the comparative examples and examples are as follows:

[0292] The structures of the main materials used in the above examples and comparative examples are shown in Table 8.

[0293] Table 8

[0294]

[0295] ​​​​​​​

[0296] The red stacked organic electroluminescent devices prepared in Examples 8-60 and Comparative Examples 3-6 were tested for performance, specifically for IVL performance at 10 mA / cm 2 The device lifetime was tested at 30 mA / cm 95 The device lifetime was tested at 30 mA / cm 2 The results are shown in Table 9 below.

[0297] Table 9

[0298]

[0299]

[0300] As can be seen from Table 9 above, the use of the compound of the present application as the n-type charge generation layer material in Examples 8-60 reduced the voltage by at least 0.33 V, increased the luminous efficiency by at least 11.8%, and increased the device lifetime by at least 13.3% compared to Comparative Examples 3-6.

[0301] It can be seen that the use of the organic compound of the present application in the n-type charge generation layer of an organic electroluminescent device can reduce the device voltage and significantly improve the luminous efficiency and device lifetime of the organic electroluminescent device.

[0302] The reason for this is that the compound of the present application has isoquinoline and pyridine as the core, and further introduces nitrogen-containing heteroaryl groups, which increases the conjugation range of the molecule and effectively adjusts the intermolecular packing, thereby improving the electron mobility and reducing the device voltage. At the same time, the compound of the present application has excellent metal complexing ability, and the compound can form a stable N-metal coordination bond with metals such as Li and Yb, effectively inhibiting the oxidation of the metal, which is conducive to improving the charge generation efficiency; and further improves the luminous efficiency and extends the service life of the organic electroluminescent device.

[0303] The above describes preferred embodiments of the present application, but the present application is not limited to the specific details of the above-described embodiments, and various simple modifications can be made to the technical solutions of the present application within the scope of the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula I: Formula I is selected from the structures shown in the following formulas Ia or Ib: Among them, Q1 is L a and L1 are selected from single bonds, Q2 is And L b and L2 is not a single bond; or Q1 is L a and at least one of L1 is not a single bond, Q2 is And L b and L2 are both selected from single bonds; each R is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuteromethyl, phenyl, pentadeuterophenyl, or naphthyl; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; L a 、L b , L1 and L2 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; Ar1, Ar2, L a , L b , the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; The condition is that Ar1, Ar2, L a 、L b At least one of L1 and L2 contains a nitrogen-containing heteroaryl group, and the nitrogen-containing heteroaryl group has 1, 2 or 3 unsaturated nitrogen atoms.

2. The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 21 carbon atoms; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 14 carbon atoms, and a heteroaryl group having 3 to 9 carbon atoms; Provided that at least one of Ar1 and Ar2 is selected from the group consisting of substituted or unsubstituted pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazoline, acridinyl, phenazinyl, dibenzo[C,H]acridinyl, phenanthroline, benzoxazolyl, benzofuro[3,2-c]pyridinyl, benzofuro[2,3-c]pyridinyl, benzofuro[2,3-b]pyridinyl, or L a , L b , L1 and L2 at least one is selected from substituted or unsubstituted: pyridylene, pyrimidylene, pyrazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, phenanthrolineylene.

3. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups: wherein the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazinyl, pyridyl, quinolyl or isoquinolyl; when the number of substituents is greater than 1, the substituents are the same or different; Provided that at least one of Ar1 and Ar2 is selected from a substituted or unsubstituted group V1, wherein the unsubstituted group V1 is selected from the group consisting of: or L a 、L b At least one of L1 and L2 is selected from a substituted or unsubstituted group V 2， The unsubstituted group V2 is selected from the group consisting of: The substituted groups V1 and V2 have one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazinyl, pyridyl, quinolyl or isoquinolyl; when the number of substituents is greater than 1, the substituents are the same or different.

4. The organic compound according to claim 1, wherein L a 、L b , L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 4 to 18 carbon atoms; and L a 、L b , at least one of L1 and L2 is not a single bond; L a 、L b , L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazinyl, pyridyl, quinolyl or isoquinolyl; Provided that at least one of Ar1 and Ar2 is selected from the group consisting of substituted or unsubstituted pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazoline, acridinyl, phenazinyl, dibenzo[C,H]acridinyl, phenanthroline, benzoxazolyl, benzofuro[3,2-c]pyridinyl, benzofuro[2,3-c]pyridinyl, benzofuro[2,3-b]pyridinyl, or L a 、L b , L1 and L2 at least one is selected from substituted or unsubstituted: pyridylene, pyrimidylene, pyrazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, phenanthrolineylene.

5. The organic compound according to claim 1, wherein L a 、L b , L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted group U, and L a 、L b , L1 and L2 is not a single bond, wherein the unsubstituted group U is selected from the group consisting of the following groups: wherein the substituted group U has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazinyl, pyridyl, quinolyl or isoquinolyl, and when the number of substituents is greater than 1, the substituents are the same or different; Provided that at least one of Ar1 and Ar2 is selected from the following substituted or unsubstituted groups V 1， The unsubstituted group V1 is selected from the group consisting of: or L a , L b At least one of L1 and L2 is selected from a substituted or unsubstituted group V 2， The unsubstituted group V2 is selected from the group consisting of: The substituted groups V1 and V2 have one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazinyl, pyridyl, quinolyl or isoquinolyl; when the number of substituents is greater than 1, the substituents are the same or different.

6. The organic compound according to claim 1, wherein Q1 is selected from the group consisting of: Q2 is selected from the group consisting of:

7. The organic compound according to claim 1, wherein Q2 is selected from the group consisting of: Q1 is selected from the group consisting of:

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

9. An organic electroluminescent device comprising an anode and a cathode, 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 8.

10. The organic electroluminescent device according to claim 9, wherein The functional layer includes an electron transport layer, and the electron transport layer comprises the organic compound according to any one of claims 1 to 8.

11. The organic electroluminescent device according to claim 9, wherein the functional layer comprises a first light-emitting unit, a second light-emitting unit and a charge generation layer; and the charge generation layer comprises the organic compound according to any one of claims 1 to 8.

12. An electronic device comprising the organic electroluminescent device according to any one of claims 9 to 11.

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