Organic compound, and organic electroluminescent device and electronic device comprising same

Abstract

The invention relates to an organic compound, and an organic electroluminescent device and an electronic device comprising the same. The structural formula of the organic compound comprises the structure shown in the formula I. When the organic compound is applied to the organic electroluminescent device, the performance of the device can be remarkably improved. # imgabs0 #

Description

Technical Field

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

[0002] At present, organic electroluminescent devices (OLEDs) are regarded as the next generation of display and lighting technology due to their advantages such as active light emission, high light emission efficiency, low power consumption, light weight, thinness, fast response speed, and wide viewing angle. Organic electroluminescent devices usually include a cathode and an anode arranged opposite to each other, and a functional layer arranged between the cathode and the anode. When 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 toward the electroluminescent layer, and the holes on the anode side also move toward 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] Organic electroluminescent devices can be of various structures, such as single-layer structures and stacked structures. A single-layer organic electroluminescent device contains only one light-emitting unit between the anode and cathode, while a stacked organic electroluminescent device is composed of multiple light-emitting units stacked. A light-emitting unit usually contains at least one light-emitting layer, a hole transport layer and an electron transport layer. On this basis, the light-emitting unit may further contain 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 charge generation and movement. CGL is constructed in a pn form, including 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, while the n-type material is doped with a low work function metal through the electron transport layer material to generate electrons.

[0004] The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the area of ​​displays increases, the voltage also increases. 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 organic electroluminescent device and an electronic device containing the same. The organic compound can be used in the organic electroluminescent device to improve the performance of the device.

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

[0007]

[0008] Among them, Q1 is Q2 is

[0009] Each R is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, or a deuterated aryl group having 6 to 12 carbon atoms;

[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 Rs are the same or different; optionally, any two adjacent Rs form a benzene ring;

[0011] 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;

[0012] 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; and L a , L b , at least one of L1 and L2 is not a single bond;

[0013] Ar1, Ar2, L a , L b , the substituents in L1 and L2 are the same or different and are 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;

[0014] The condition is that Ar1, Ar2, L a , L b At least one of L1, L2 and L4 contains a nitrogen-containing heteroaryl group, and the nitrogen-containing heteroaryl group has 1, 2 or 3 unsaturated nitrogen atoms.

[0015] The 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 above-mentioned organic compound.

[0016] In a third aspect of the present application, an electronic device is provided, which includes the organic electroluminescent device described in the second aspect.

[0017] The compounds of the present application are based on isoquinoline and pyridine, and further introduce nitrogen-containing heteroaryl groups on this basis, which increases the conjugation range of the molecule and effectively adjusts the stacking between molecules, thereby improving the mobility of electrons and reducing the device voltage. At the same time, the compounds of the present application have excellent metal complexing ability. The compounds can form stable N-metal coordination bonds with metals such as Li and Yb, effectively inhibiting the oxidation of metals, which is beneficial to improving the efficiency of charge generation; thereby improving the luminous efficiency and extending 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 diagram of the structure 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 diagram of the structure of an electronic device according to an 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 device DETAILED DESCRIPTION

[0029] 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.

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

[0031]

[0032] Among them, Q1 is Q2 is

[0033] Each R is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, or a deuterated aryl group having 6 to 12 carbon atoms;

[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 Rs are the same or different; optionally, any two adjacent Rs form a benzene ring;

[0035] 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;

[0036] 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; and L a , L b , at least one of L1 and L2 is not a single bond;

[0037] Ar1, Ar2, L a , L b , the substituents in L1 and L2 are the same or different and are 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;

[0038] The condition is that Ar1, Ar2, L a , L b At least one of L1, L2 and L4 contains a nitrogen-containing heteroaryl group, and the nitrogen-containing heteroaryl group has 1, 2 or 3 unsaturated nitrogen atoms.

[0039] 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 Rs form a benzene ring" includes: the scenario where any two adjacent Rs form a benzene ring, and the scenario where any two adjacent Rs form a benzene ring. "Any two adjacent" may include two substituents on the same atom, and may also include two adjacent atoms each having one substituent; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are connected; when there is one substituent on two adjacent atoms each, the two substituents may be fused into a ring.

[0040] In this application, the descriptions used in the phrases "each ... independently is" and "... are independently" and "... are independently" are interchangeable 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 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 with a substituent Rc or an aryl 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 1 or more.

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

[0043] In the present application, "plurality" means more than 2, 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] The "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. The aryl group can be a monocyclic aryl group (such as phenyl) or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bonds can also be regarded as aryl groups of the present application. Among them, condensed ring aryl groups can include, for example, bicyclic condensed aryl groups (such as naphthyl), tricyclic condensed aryl groups (such as phenanthrenyl, fluorenyl, anthracenyl), etc. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, 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 the present application, Ar1, Ar2, L a , L b The aryl substituents of L1 and L2 are exemplified, but not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl and the like.

[0051] 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 conjugated by carbon-carbon bonds, 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.

[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 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, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.

[0054] In the present application, Ar1, Ar2, L a , L b The heteroaryl substituents of L1 and L2 include, but are not limited to, triazine, 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, 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.

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

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

[0059] In the present application, the carbon number of the 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 the deuterated alkyl group include, but are not limited to, trideuterated methyl group.

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

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

[0062] In this application, Refers to the chemical bonds that connect to other groups.

[0063] In this application, the single bond extending from the ring system without positioning the connecting bond is " ", which 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, and the meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10).

[0064]

[0065] 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 its meaning includes any possible connection method shown in formula (X'-1) to formula (X'-4).

[0066]

[0067] The non-positional 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-positional connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (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, L2 and L4 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, benzofurano[3,2-c]pyridine, benzofurano[2,3-c]pyridine, benzofurano[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 R are the same or different; optionally, any two adjacent R form a benzene ring; that is, any two adjacent R 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 at least one of 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 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 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, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, alkyl having 1-5 carbon atoms, haloalkyl having 1-5 carbon atoms, deuterated alkyl having 1-5 carbon atoms, trialkylsilyl having 3-7 carbon atoms, deuterated aryl having 6-12 carbon atoms, aryl having 6-14 carbon atoms, heteroaryl having 3-9 carbon atoms;

[0082] 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, benzofurano[3,2-c]pyridinyl, benzofurano[2,3-c]pyridinyl, benzofurano[2,3-b]pyridinyl, or L a , L b , at least one of L1 and L2 is selected from substituted or unsubstituted: pyridylene, pyrimidylene, pyrazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, phenanthrolineylene.

[0083] 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 group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:

[0084]

[0085] Wherein, the substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazine, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different;

[0086] 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:

[0087]

[0088] 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:

[0089]

[0090] The substituted groups V1 and V2 have one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazine, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different.

[0091] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of the following groups:

[0092]

[0093]

[0094] The condition is that when L a , L b , L1 and L2 are each independently selected from a single bond, substituted or unsubstituted: phenylene, biphenylene, naphthylene, anthrylene, phenanthrenyl, pyrenylene, at least one of Ar1 and Ar2 is selected from:

[0095]

[0096]

[0097] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of the following groups:

[0098]

[0099]

[0100] In this application, L a , L b , L1 and L2 are the same or different and can be independently selected from: a single bond, a substituted or unsubstituted arylene group 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 a substituted or unsubstituted heteroarylene group 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; and L a , L b At least one of L1 and L2 is not a single bond.

[0101] In some embodiments of the present application, La , 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 16 carbon atoms, or a substituted or unsubstituted heteroarylene group having 4 to 24 carbon atoms; and L a , L b , at least one of L1 and L2 is not a single bond;

[0102] 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, phenanthryl, triazine, pyridyl, quinolyl or isoquinolyl;

[0103] 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, benzofurano[3,2-c]pyridinyl, benzofurano[2,3-c]pyridinyl, benzofurano[2,3-b]pyridinyl, or L a , L b , at least one of L1 and L2 is selected from substituted or unsubstituted: pyridylene, pyrimidylene, pyrazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, phenanthrolineylene.

[0104] 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, a substituted or unsubstituted group U, and L a , L b At least one of L1 and L2 is not a single bond, wherein the unsubstituted group U is selected from the group consisting of the following groups:

[0105]

[0106] Wherein, the substituted group U has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazine, pyridyl, quinolyl or isoquinolyl. When the number of the substituents is greater than 1, the substituents are the same or different;

[0107] 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:

[0108]

[0109] 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:

[0110]

[0111] The substituted groups V1 and V2 have one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazine, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different.

[0112] 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;

[0113]

[0114]

[0115] Provided that, when Ar1 and Ar2 are each independently selected from substituted or unsubstituted: phenylene, biphenylene, naphthylene, anthrylene, phenanthrenyl, pyrenyl, triphenylene, L a , L b At least one of L1 and L2 is selected from

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

[0117]

[0118] L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

[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 the following groups:

[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 the following groups:

[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, trideuterated methyl, phenyl, pentadeuterated phenyl 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 present application, in the above formula Ia, 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.

[0138] In some embodiments of the present application, in the above formula Ia, Q1 is selected from the group consisting of the following groups:

[0139]

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

[0141]

[0142]

[0143]

[0144] In some embodiments of the present application, in the above formula Ia, Q1 is And 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.

[0145] In some embodiments of the present application, in the above formula Ia, Q2 is selected from the group consisting of the following groups:

[0146]

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

[0148]

[0149]

[0150]

[0151] In some embodiments of the present application, in the above formula Ib, 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.

[0152] In some embodiments of the present application, in the above formula Ib, Q1 is selected from the group consisting of the following groups:

[0153]

[0154] Q2 is selected from the group consisting of:

[0155]

[0156]

[0157] Optionally, the organic compound is selected from the group consisting of the following compounds.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] A second aspect of the present application provides an organic electroluminescent device, 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 present application.

[0177] In one embodiment of the present application, the functional layer includes 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 includes the organic compound described in the present application.

[0178] In one embodiment of the present application, the structure of the organic electroluminescent device is as follows: Figure 1 As shown, it includes an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes 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, and the electron transport layer 340 contains the organic compound described in the present application.

[0179] In the present application, the anode 100 includes an anode material, which is optionally 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. Optionally, a transparent electrode including indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0180] In the present application, 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;

[0181]

[0182] In one 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 may be selected from triarylamine compounds or other types of compounds, and those skilled in the art may select them 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 one embodiment of the present application, the material of the hole transport layer 321 includes HT-1.

[0186] In one embodiment of the present application, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials can be selected from carbazole polymers or other types of compounds, which are not specifically limited in the present application. For example, in some embodiments of the present application, the electron blocking layer 322 is composed of compound EB-1 composition.

[0187] Optionally, the light-emitting layer material may consist of a single light-emitting material, or may include 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] Alternatively, the host material of the light emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. The host material of the organic light emitting layer 330 may be one compound or a combination of two or more compounds.

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

[0191] In a 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 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of alkali metals and organic matter. In one embodiment of the present application, the electron injection layer 350 includes Yb.

[0193] In the present application, cathode 200 includes 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 alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.

[0194] In addition, the present application also provides another Figure 2 The organic electroluminescent device shown in the figure 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 the organic compound described in the present application. Figure 2The organic electroluminescent device shown is also referred to as a stacked organic electroluminescent device hereinafter.

[0195] In one embodiment of the present application, the stacked organic electroluminescent device includes 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 cathode 100 and the anode 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 contains the organic compound described in the present application.

[0196] In one embodiment of the present application, the first light-emitting unit 410 includes 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; the second light-emitting unit 430 includes 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 one embodiment of the present application, the charge generation layer 420 includes 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 one embodiment of the present application, the n-type charge generation layer includes the organic compound described in the present application.

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

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

[0200] In the present application, the anode 100 includes an anode material. Optionally, the anode material includes indium tin oxide (ITO).

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

[0202] In one embodiment of the present application, the material of the first hole transport layer 411 and the second hole transport layer 431 includes HT-1.

[0203] In one embodiment of the present application, the materials of the first hole adjustment layer 412 and the second hole adjustment layer 432 include 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 may include the same or different host materials and the same or different guest materials.

[0205] In a specific embodiment of the present application, the main 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 materials of the first electron transport layer 414 and the second electron transport layer 434 include ET-1

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

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

[0210] A 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 one embodiment, Figure 3 As shown, the provided electronic device is an electronic device 500, which includes the above-mentioned organic electroluminescent device. 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, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0212] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0213] Synthesis example

[0214] Synthesis of intermediates

[0215] 1. Synthesis of intermediate IMA-1

[0216]

[0217] 1-Chloro-3-phenylisoquinoline (15 g, 62.6 mmol) was dissolved in 1,4-dioxane, and then bis(pinacol)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 in a nitrogen atmosphere. After cooling to room temperature, the reaction solution was extracted with water and dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain the intermediate IMA-1 (12.9 g, yield 62%).

[0218] 2. Synthesis of intermediate IM BX and intermediate IM BXY

[0219]

[0220] Dissolve 1-bromo-3-chloroisoquinoline (12g, 49.8mmol) and 2-phenylpyridine-6-boronic acid pinacol ester (16.7g, 59.4mmol) in 80mL toluene, and then add tetrakis(triphenylphosphine)palladium (0.57g, 0.50mmol), K2CO3 (10.2g, 74.2mmol), 40mL ethanol, and 20mL water. Heat and reflux for 12 hours under nitrogen atmosphere. After cooling to room temperature, extract with water and dichloromethane, dry with anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. The obtained solid was dissolved in dichloromethane and dried, and purified by silica gel chromatography column, dichloromethane: n-heptane = 1:1 as eluent to obtain intermediate IM B-1 (8.8g, yield 56%).

[0221] According to the synthesis method of intermediate IMB-1, the only difference is that raw material 2 is used instead of 1-bromo-3-chloroisoquinoline, and raw material 3 / intermediate IMA-1 is used instead of 2-phenylpyridine-6-boronic acid pinacol ester to prepare intermediates IMB-2 to IMB-15, as shown in Table 1.

[0222] Table 1

[0223]

[0224]

[0225]

[0226] Referring to the synthesis method of intermediate IM B-1, the only difference is that intermediate IM BX is used instead of 1-bromo-3-chloroisoquinoline, and raw material 4 is used instead of 2-phenylpyridine-6-boronic acid pinacol ester to prepare intermediates IM B-2-1, IM B-3-1, IM B-3-2IM, B-8-1, IM B-11-1, and IM B-12-1 as shown in Table 2.

[0227] Table 2

[0228]

[0229]

[0230] 3. Synthesis of Intermediate IM CX

[0231] Referring to the synthesis method of intermediate IMA-1, the only difference is that the intermediates in the intermediate IM BX series are used instead of 1-chloro-3-phenylisoquinoline to prepare intermediates IM C-1 to IM C-5, as 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 (5g, 15.5mmol) and intermediate IMA-1 (12.9g, 38.8mmol) in 30mL toluene, and then add tetrakis(triphenylphosphine)palladium (0.18g, 0.16mmol), K2CO3 (6.4g, 46.6mmol), 10mL ethanol, and 5mL water. Heat to reflux for 12 hours under a nitrogen atmosphere. After cooling to room temperature, add 100mL water and stir for 30min, filter, rinse with 100mL ethanol, and repeat 3 times. The obtained solid was recrystallized with dichloromethane to obtain 5.1g of compound 2 with a yield of 58%. m / z: 562.22[M+H] + .

[0239] The compounds in Table 4 were synthesized by referring to the synthesis method of compound 2, except that raw material 5 / intermediate IMB-X was used instead of 2,6-dibromo-4-chloropyridine, and raw material 6 / intermediates in the series of intermediates IM CX were used instead of intermediate IMA-1; the raw materials, structures, yields and mass spectra of the synthesized compounds are shown in Table 4.

[0240] Table 4

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] The NMR data of the compound are shown in Table 5:

[0251] Table 5

[0252]

[0253] Example 1: Blue organic electroluminescent device

[0254] 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 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.

[0255] Compounds HT-1 and NDP-9 were co-evaporated at a thickness ratio of 98%:2% on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer (HIL) is formed by vacuum evaporating HT-1 on the hole injection layer to form a layer with a thickness of hole transport layer.

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

[0257] Next, on the hole adjustment layer, compound BH-1 (doping host) and compound BD-1 (doping guest) were co-evaporated at a ratio of 98%:2% to form a layer with a thickness of of the light emitting layer (EML).

[0258] On the light-emitting layer, compound 2 and LiQ were mixed in a thickness 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 deposition rate of 1:10 and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.

[0259] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the manufacture of green organic electroluminescent devices.

[0260] Embodiment 2-embodiment 7:

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

[0262] Comparative Example 1-Comparative Example 2

[0263] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound 2 was replaced by compounds A and B in Table 6 below when forming the electron transport layer.

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

[0265] Table 6

[0266]

[0267] The performance of the blue organic electroluminescent devices prepared in Examples 1-7 and Comparative Examples 1-2 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 15mA / cm 2 The test was carried out under the conditions of , and the test results are shown in the following Table 7:

[0268] Table 7

[0269]

[0270]

[0271] Referring to Table 7 above, it can be seen that in Examples 1-7, the compounds of the present invention are used as electron transport layer materials. Compared with Comparative Examples 1-2, the voltage is reduced by at least 0.18V, the luminous efficiency is increased by at least 12.7%, and the device life is 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 the organic electroluminescent device can reduce the device voltage and improve the luminous efficiency and T of the organic electroluminescent device. 95 life.

[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 overlapping 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 at a thickness ratio of 98%:2% on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer (HIL) is formed by vacuum evaporating HT-1 on the hole injection layer to form a layer with 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, on the first hole adjustment layer, compound RH-1 and compound RD-1 were co-evaporated at a thickness ratio of 98%:2% to form a layer with a thickness of The first light emitting layer (EML) of

[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 A p-type charge generation layer (p-CGL) is formed.

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

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

[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 layer with a thickness of The second emitting layer (EML-2)

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

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

[0286] Finally, 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.

[0287] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1 is formed to form an organic cover layer (CPL), thereby completing the manufacture of a red stacked organic electroluminescent device.

[0288] Embodiment 9-embodiment 60:

[0289] An organic electroluminescent device was prepared in the same manner as in Example 8, except that the compound in Table 9 was used instead of Compound 2 in Example 8 when preparing the n-type charge generation layer.

[0290] Comparative Example 3-Comparative Example 6

[0291] An organic electroluminescent device was prepared in the same manner as in Example 8, except that Compounds C, D, E and F in Table 8 were used instead of Compound 2 in Example 8 when preparing the n-type charge generation layer.

[0292] When preparing the organic electroluminescent device, the structures of the materials used in the comparative examples and the examples are as follows:

[0293] The main material structures used in the above embodiments and comparative examples are shown in Table 8.

[0294] Table 8

[0295]

[0296] The performance of the red stacked organic electroluminescent devices prepared in Examples 8-60 and Comparative Examples 3-6 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 9 below.

[0297] Table 9

[0298]

[0299]

[0300] Referring to Table 9 above, it can be seen that in Examples 8-60, the compounds of the present application are used as n-type charge generation layer materials. Compared with Comparative Examples 3-6, the voltage is reduced by at least 0.33 V, the luminous efficiency is increased by at least 11.8%, and the device life is increased by at least 13.3%.

[0301] It can be seen that using 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 life of the organic electroluminescent device.

[0302] The reason is that the compounds in the application are based on isoquinoline and pyridine as the core, and nitrogen-containing heteroaryl groups are further introduced on this basis, which increases the conjugation range of the molecule and effectively adjusts the stacking between molecules, thereby improving the mobility of electrons and reducing the device voltage. At the same time, the compounds in the application have excellent metal complexing ability. The compounds can form stable N-metal coordination bonds with metals such as Li and Yb, effectively inhibiting the oxidation of metals, which is beneficial to improving the efficiency of charge generation; thereby improving the luminous efficiency and extending the service life of organic electroluminescent devices.

[0303] The preferred embodiments of the present application are described in detail above; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within 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: Among them, Q1 is Q2 is Each R is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, or a deuterated aryl group having 6 to 12 carbon atoms; 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; 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; and L a , L b , at least one of L1 and L2 is not a single bond; Ar1, Ar2, L a , L b , the substituents in L1 and L2 are the same or different and are 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, L2 and L4 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 Each R is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuteromethyl, phenyl, pentadeuterophenyl or naphthyl; n is 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.

3. The organic compound according to claim 1, wherein Formula I is selected from the structures shown in the following formula Ia or Ib: In the above formula Ia, each R is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, pentadeuterated phenyl or naphthyl.

4. The organic compound according to claim 1, wherein 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.

5. 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; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, alkyl having 1-5 carbon atoms, haloalkyl having 1-5 carbon atoms, deuterated alkyl having 1-5 carbon atoms, trialkylsilyl having 3-7 carbon atoms, deuterated aryl having 6-12 carbon atoms, aryl having 6-14 carbon atoms, heteroaryl having 3-9 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, benzofurano[3,2-c]pyridinyl, benzofurano[2,3-c]pyridinyl, benzofurano[2,3-b]pyridinyl, or L a , L b , at least one of L1 and L2 is selected from substituted or unsubstituted: pyridylene, pyrimidylene, pyrazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, phenanthrolineylene.

6. 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, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazine, pyridyl, quinolyl or isoquinolyl; when the number of the 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, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazine, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different.

7. 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, phenanthryl, triazine, 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, benzofurano[3,2-c]pyridinyl, benzofurano[2,3-c]pyridinyl, benzofurano[2,3-b]pyridinyl, or L a , L b , at least one of L1 and L2 is selected from substituted or unsubstituted: pyridylene, pyrimidylene, pyrazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, phenanthrolineylene.

8. 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 At least one of 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, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triazine, pyridyl, quinolyl or isoquinolyl. When the number of the 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, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, naphthyl, biphenyl, phenanthryl, triazine, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different.

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

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

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

12. 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 11.

13. The organic electroluminescent device according to claim 12, wherein: The functional layer includes an electron transport layer, and the electron transport layer includes the organic compound according to any one of claims 1 to 11. 14 . The organic electroluminescent device according to claim 12 , 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 claim 1 .

15. An electronic device comprising the organic electroluminescent device according to any one of claims 12 to 14.

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