Compounds and their applications in organic optoelectronic devices

Abstract

The present invention relates to the field of organic electroluminescent materials, particularly to a compound and its application in organic optoelectronic devices. The compound has the chemical structure of Formula (I): #imgabs0#. When applied to organic devices, the compound of the present invention can improve the device's electron or hole transport efficiency. The molecule also exhibits high stability, thereby enhancing the device's luminous efficiency and service life.

Description

Technical Field

[0001] The present invention relates to the field of organic electroluminescent materials, in particular to a compound and its application in organic photoelectric devices. Background Art

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers sandwiched between layers of organic functional materials. Currently, this technology has been widely adopted in display panels for products such as new lighting fixtures, smartphones, and tablets, and is expected to expand into large-scale display products such as televisions. It is a rapidly developing and technologically demanding new display technology. Common functional organic materials used in OLED devices include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as luminescent host materials and luminescent guest materials (dyes). To this end, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve low startup voltages, high luminous efficiency, and extended device lifespans. To date, the development of existing OLED optoelectronic functional materials lags far behind the requirements of panel manufacturers. Therefore, the development of higher-performing organic functional materials to meet the current demands of the industry is urgent. Currently, hole transport materials primarily employ aromatic amine compounds with excellent hole transport properties. N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB) is widely used in organic electroluminescent devices with various colors of light due to its moderate highest occupied orbital energy level and good hole mobility. However, the glass transition temperature of this molecule is low (98°C), and the device is prone to phase change under the action of accumulated Joule heat when working for a long time, which has a great impact on the life of the device. Therefore, it is very necessary to design hole transport materials with both high mobility and glass transition temperature. In addition, the mobility performance of electron transport materials needs to be further improved, and the solubility of the material in common solvents needs to be improved in order to be suitable for industrial production. Summary of the Invention

[0003] In view of the above-mentioned shortcomings of the prior art, an object of the present invention is to provide a compound and its application in an organic optoelectronic device to solve the problems in the prior art.

[0004] To achieve the above-mentioned and other related purposes, the present invention provides a compound having a chemical structure as shown in formula (I):

[0005]

[0006] in:

[0007] Said A is selected from CR5R6, SiR7R8, NR9, O, S:

[0008] R1-R4 are the same or different and are independently selected from hydrogen, deuterium, substituted or unsubstituted linear or branched C1-C30 alkyl; substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl, or substituted or unsubstituted aromatic amine, or bonded to adjacent groups to form a ring;

[0009] R5-R8 are each independently selected from hydrogen, deuterium, C1-C10 alkyl, or C1-C10 deuterated alkyl;

[0010] A is selected from CR9R 10 、SiR 11 R 12 NR 13 , O, or S: Among them, R9-R 13 is selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 deuterated alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 deuterated aryl, substituted or unsubstituted C3-C30 deuterated heteroaryl, or R9, R 10 Bonding ring, R 11 、R 12 Bond to form a ring.

[0011] In some cases, A is preferably selected from the following:

[0012]

[0013] Among them, R 13 is a substituted or unsubstituted C6-C30 aryl group; * is an atom connection site.

[0014] Another aspect of the present invention provides an organic layer comprising the compound according to the first aspect of the present invention.

[0015] Another aspect of the present invention provides use of the compound of the present invention and / or the organic layer of the present invention in an organic optoelectronic device.

[0016] Another aspect of the present invention provides an organic photoelectric device, comprising a first electrode, a second electrode and an organic layer as described in the present invention, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer.

[0017] Another aspect of the present invention provides a display or lighting device, which includes the organic optoelectronic device of the present invention.

[0018] Compared with the prior art, the present invention has the following beneficial effects:

[0019] The compound provided by the present invention reduces the LUMO of the molecule by introducing a heteroatom group into the benzene ring region of fluorene, and the LUMO of the molecule is fixed in the region of fluorene. The HOMO of the molecule is also reduced, which better matches the HOMO and LUMO energy level requirements of the device. In addition, compared with the compound of the comparative invention, the power supply effect of the aryl and alkyl groups is moderate due to the electric withdrawal effect of the heteroatom, so that the compound of the present invention is applied to organic devices, which can enable the device to have a higher hole mobility and can effectively block electrons and excitons from entering the hole transport layer, and the device has a higher luminous efficiency and service life. DETAILED DESCRIPTION

[0020] The following describes in detail embodiments of the disclosed compounds and their applications in organic optoelectronic devices. Those skilled in the art will readily appreciate the other advantages and benefits of the present invention based on the disclosure herein. The present invention may also be implemented or applied through various other specific embodiments, and the details herein may be modified or altered based on different perspectives and applications without departing from the spirit of the present invention.

[0021] Before further describing the specific embodiments of the present invention, it should be understood that the scope of protection of the present invention is not limited to the specific specific embodiments described below; it should also be understood that the terms used in the examples of the present invention are for describing specific specific embodiments rather than for limiting the scope of protection of the present invention; in the present specification and claims, unless otherwise expressly stated herein, the singular forms "a", "an" and "the" include plural forms.

[0022] When the embodiments provide numerical ranges, it should be understood that, unless otherwise specified in the present invention, both endpoints of each numerical range and any numerical value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those generally understood by those skilled in the art. In addition to the specific methods, equipment, and materials used in the embodiments, according to the understanding of the prior art by those skilled in the art and the description of the present invention, any methods, equipment, and materials of the prior art similar or equivalent to the methods, equipment, and materials described in the embodiments of the present invention may also be used to implement the present invention.

[0023] After extensive research, the inventors of the present invention have provided a compound based on the oxolane series. The inventors of the present invention have found that by introducing oxolane derivatives into triarylamine systems and combining them with electron-withdrawing groups, a series of hole transport materials and electron transport materials with excellent performance are obtained. The introduction of oxolane derivatives, the aliphatic ring has better electron-donating ability than the aromatic group, so that the compound has good hole and electron transport properties and thermal stability. Therefore, this type of compound can provide a longer service life for organic electroluminescent devices. In oxolane derivatives, due to the electron-withdrawing ability of the oxygen atom, when combined with the triazine electron-withdrawing group, the LUMO energy level of the overall molecule can be deepened, thereby enhancing the electron transport ability of the molecule. When the oxolane group is introduced into the bipolar molecular material, it also shows excellent device life and efficiency. On this basis, the present invention was completed.

[0024] Examples of the substituents in the present invention are described below, but the substituents are not limited thereto:

[0025] [Substituted or unsubstituted] means substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heteroaryl group, an acenaphthenyl group, a compound group, or unsubstituted; or substituted with a substituent connecting two or more of the substituents exemplified above, or unsubstituted. For example, a "substituent connecting two or more substituents" may include a biphenyl group, i.e., a biphenyl group may be an aryl group, or a substituent connecting two phenyl groups.

[0026] [Alkyl] can be straight chain or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes but is not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl.

[0027] The above description of the alkyl group also applies to the alkyl group in the aralkyl group, aralkylamino group, alkylaryl group and alkylamino group.

[0028] [Heteroalkyl] can be a straight or branched alkyl containing heteroatoms, and the number of carbon atoms is not particularly limited. In certain embodiments, heteroalkyl includes but is not limited to alkoxy, alkylthio, alkylsulfonyl, etc. Alkoxy, for example, can include but is not limited to methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. Examples of alkylthio groups include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.

[0029] [Cycloalkyl] may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

[0030] [Heterocycloalkyl] can be a cycloalkyl containing heteroatoms, and the number of carbon atoms is not particularly limited. In some embodiments, heterocycloalkyl includes but is not limited to wait.

[0031] [Aryl] There are no particular limitations and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group may be substituted, for example, 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorenyl, and the like. In addition, two of the substituents may be combined to form a spirocyclic structure, for example, 9,9'-spirobifluorenyl, and the like.

[0032] The above description of the aryl group applies to the arylene group, except that the arylene group is divalent.

[0033] The above description of the aryl group can be applied to the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, arylalkyl group, arylalkylamino group, arylalkenyl group, alkylaryl group, arylamino group and arylheteroarylamino group.

[0034] [Heteroaryl] contains one or more of N, O, P, S, Si and Se as heteroatoms. Heteroaryl includes, but is not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, azinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, dihydroindole, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopy ... Pyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoquinazolinyl, benzimidazophenanthridinyl, spiro[fluorene-9,9'-xanthene], benzobinaphthyl, dinaphthofuranyl, naphthylbenzofuranyl, dinaphthothienyl, naphthylbenzothienyl, triphenylphosphine oxide, triphenylborane, etc.

[0035] The above description of the heteroaryl group can be applied to the heteroaryl group in the heteroarylamine group and the arylheteroarylamine group.

[0036] The above description of heteroaryl groups applies to heteroarylene groups, except that the heteroarylene group is divalent.

[0037] [Bonded ring] refers to the formation of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocycle, an aromatic heterocycle, or a condensed ring thereof by adjacent groups. For example, R9, R 10 Bonding into rings can form Combined with the compound of formula (I) Other similar ones are not listed here.

[0038] In one aspect, the present invention provides a compound having a chemical structure as shown in formula (I):

[0039]

[0040] R1-R4 are the same or different and are independently selected from hydrogen, deuterium, a substituted or unsubstituted linear or branched C1-C30 alkyl group; a substituted or unsubstituted C1-C30 heteroalkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted aromatic amine group, or a ring formed by bonding with an adjacent group. The substituted or unsubstituted C3-C60 heteroaryl group may be, for example, a substituted or unsubstituted C3-C60 nitrogen-containing aryl group, a substituted or unsubstituted C3-C60 oxygen-containing aryl group, or a substituted or unsubstituted C3-C60 sulfur-containing aryl group. Alternatively, the substituted or unsubstituted C3-C60 heteroaryl group may be, for example, a substituted or unsubstituted C3-C30 nitrogen atom-containing aryl group, a substituted or unsubstituted C3-C30 oxygen atom-containing aryl group, or a substituted or unsubstituted C3-C30 sulfur atom-containing aryl group.

[0041] R5-R8 are each independently selected from hydrogen, deuterium, C1-C10 alkyl, or C1-C10 deuterated alkyl;

[0042] A is selected from CR9R 10 、SiR 11 R 12 NR 13 , O, or S: Among them, R9-R 13 Each is independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 deuterated alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 deuterated aryl, and substituted or unsubstituted C3-C30 deuterated heteroaryl.

[0043] In some embodiments, the compound is of the general formula

[0044] In some embodiments, in formula (I), the number of carbon atoms of the aforementioned alkyl group may also be 1 to 10, 1 to 20, or 20 to 30, etc. The number of carbon atoms of the aforementioned cycloalkyl group may also be 3 to 10, 3 to 20, or 3 to 30, etc. The number of carbon atoms of the aforementioned heteroalkyl group may also be 3 to 10, 1 to 20, or 20 to 30, etc. The number of carbon atoms of the aforementioned heterocycloalkyl group may also be 3 to 10, 3 to 20, or 20 to 30, etc. The number of carbon atoms of the aforementioned aryl group may also be 6 to 10, 6 to 20, or 20 to 30, etc. The number of carbon atoms of the aforementioned heteroaryl group may also be 6 to 10, 6 to 20, or 20 to 30, etc.

[0045] The above description of the number of carbon atoms in the aryl group and the heteroaryl group is applicable to the arylene group and the heteroarylene group mentioned in the present invention.

[0046] In the compounds provided by the present invention, R1-R4 are the same or different and are independently selected from hydrogen, deuterium, substituted or unsubstituted straight-chain or branched C1-C20 alkyl; substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted aromatic amine, or bonded with adjacent groups to form a ring.

[0047] Optionally, R1-R4 are the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted linear or branched C1-C10 alkyl; substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C30 heteroaryl, or substituted or unsubstituted aromatic amine, or bonded to an adjacent group to form a ring.

[0048] In some embodiments, at least one of R1-R4 is selected from the following structures:

[0049]

[0050] The group of formula (II) is a substituted or unsubstituted aromatic amine group. The group of formula (III) is a substituted or unsubstituted C3-C30 heteroaryl group.

[0051] in:

[0052] L1-L6 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

[0053] Optionally, L1-L6 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C3-C20 heteroaryl group.

[0054] Further optionally, L1 to L6 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted trimphenylene group.

[0055] Preferably, L1 to L6 are each independently selected from a single bond, a phenylene group, a naphthylene group, an anthrylene group, a dibenzofuranylene group, a dibenzothiophenylene group, or 9-phenylcarbazole.

[0056] Ar1 to Ar4 are the same or different, and are independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

[0057] Optionally, Ar1-Ar4 are the same or different, and are independently selected from a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C3-C20 heteroaryl group.

[0058] Further optionally, the Ar1 to Ar4 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or any one of the following substituted or unsubstituted groups:

[0059]

[0060] E is an electron-withdrawing group containing a nitrogen atom, an electron-withdrawing group containing a fluorine atom, an electron-withdrawing group containing a phosphorus atom, an electron-withdrawing group containing an oxygen atom, or an electron-withdrawing group containing a sulfur atom.

[0061] Optionally, E is selected from 1,3,5-triazine.

[0062] When R1-R4 are not selected from the groups represented by formula (II) or formula (III), in some embodiments, R1-R4 are each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, or any one of the following substituted or unsubstituted groups:

[0063]

[0064]

[0065] In the compounds provided by the present invention, R5-R8 are each independently selected from hydrogen, deuterium, C1-C10 alkyl, or C1-C10 deuterated alkyl.

[0066] Optionally, in the compounds provided by the present invention, R5-R8 are each independently selected from hydrogen, deuterium, C1-C4 alkyl, or C1-C4 deuterated alkyl.

[0067] Further optionally, said R5-R8 are each independently selected from methyl or deuterated methyl.

[0068] Since the life of the material is improved after hydrogen atoms are replaced by deuterium atoms, in the compound provided by the present invention, R5-R8 are preferably CD3.

[0069] In the compounds provided by the present invention, A is selected from CR9R 10 、SiR 11 R 12 NR 13 , O, or S: Among them, R9-R 13 are independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 deuterated alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 deuterated aryl, substituted or unsubstituted C3-C30 deuterated heteroaryl, or R9, R 10 Bonding ring, R 11 、R 12 Bond to form a ring.

[0070] In some embodiments, A is selected from NR 13 , O, or S or any one of the following groups:

[0071]

[0072] Among them, R 13 is a substituted or unsubstituted C6-C30 aryl group; * is an atom connection site. 13 It is phenyl or naphthyl, etc.

[0073] In some embodiments, A is selected from NR 13 , R 13 An electron-withdrawing group containing a nitrogen atom is selected from the group consisting of:

[0074]

[0075]

[0076] Among the compounds provided by the present invention, the compound is selected from any one of the following chemical structures:

[0077]

[0078]

[0079]

[0080] Specifically, the above structure may be unsubstituted or substituted with one or more substituents selected from the following, for example, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylheteroarylamine group, an arylphosphino group, and a heteroaryl group.

[0081] Another aspect of the present invention provides an organic layer comprising the aforementioned compound of the present invention.

[0082] Another aspect of the present invention provides use of the aforementioned compound and / or the aforementioned organic layer in an organic optoelectronic device.

[0083] The organic optoelectronic device provided by the present invention comprises a first electrode, a second electrode, and one or more organic layers disposed between the first and second electrodes, forming a bottom- or top-emitting device structure. The organic layer may be a single-layer structure or a multilayer tandem structure comprising two or more organic layers, wherein the organic layer may comprise at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, or an electron transport layer. The device can be prepared using common methods and materials for preparing organic optoelectronic devices. The organic optoelectronic device of the present invention employs a compound as its organic layer.

[0084] In the organic optoelectronic device provided by the present invention, the first electrode serves as the anode layer. The anode material can be, for example, a material with a large work function, which allows for smooth hole injection into the organic layer. Further examples include metals, metal oxides, combinations of metals and oxides, and conductive polymers. Examples of metal oxides include indium tin oxide (ITO), zinc oxide, indium oxide, and indium zinc oxide (IZO).

[0085] In the organic optoelectronic device provided by the present invention, the second electrode serves as the cathode layer. The cathode material can be, for example, a material with a low work function, allowing electrons to be smoothly injected into the organic layer. The cathode material can be, for example, a metal or a multilayer structure. The metal can be, for example, magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, lead, or alloys thereof. The cathode material is preferably selected from magnesium and silver.

[0086] In the organic optoelectronic device provided by the present invention, the material of the hole injection layer is preferably a material whose highest occupied molecular orbital (HOMO) is between the work function of the anode material and the HOMO of the surrounding organic layer, as a material that is advantageous in receiving holes from the anode at low voltage.

[0087] In the organic optoelectronic device provided herein, the hole transport layer is a material having high hole mobility suitable for receiving holes from the anode or hole injection layer and transporting the holes to the light-emitting layer. Materials for the hole transport layer include, but are not limited to, organic materials containing arylamines, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0088] In the organic optoelectronic device provided by the present invention, the material of the light-emitting layer can generally be selected from materials with good quantum efficiency for fluorescence or phosphorescence as materials that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining the holes with the electrons.

[0089] In the organic photoelectric device provided by the present invention, the material of the electron transport layer is a material having high electron mobility, which is suitable as a material that advantageously receives electrons from the cathode and transports the electrons to the light-emitting layer.

[0090] In the organic photoelectric device provided by the present invention, the material of the cover layer generally has a high refractive index, and thus can help improve the light efficiency of the organic light-emitting device, especially help improve the external light-emitting efficiency.

[0091] In the organic photoelectric device provided by the present invention, the organic photoelectric device is an organic photovoltaic device, an organic light-emitting device, an organic solar cell, an electronic paper, an organic photoreceptor, an organic thin film transistor, etc.

[0092] Another aspect of the present invention provides a display or lighting device comprising the organic optoelectronic device of the present invention.

[0093] The following describes the embodiments of the present invention through specific examples.

[0094] Synthesis Example:

[0095] The synthesis of the compound represented by the above formula (I) can be carried out using known methods. For example, a cross-coupling reaction using transition metals such as nickel and palladium. Other synthesis methods are CC, CN coupling reactions using transition metals such as magnesium or zinc. The above reactions are limited to the characteristics of mild reaction conditions and superior selectivity of various functional groups, and the Suzuki and Buchwald reactions are preferred. The compounds of the present invention are illustrated by the following examples, but are not limited to the compounds and synthesis methods illustrated in these examples. The starting raw materials and solvents of the present invention and some commonly used OLED intermediates and other products were purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. were purchased from Sigma-Aldrich. 1 H-NMR data were measured using a JEOL (400 MHz) nuclear magnetic resonance spectrometer; HPLC data were measured using a Shimadzu LC-20AD high performance liquid chromatography spectrometer.

[0096] The compounds used in the examples are:

[0097]

[0098]

[0099] Example 1

[0100] Synthesis of compound H-6

[0101]

[0102] 1) Synthesis of intermediate H-6-1

[0103] Under an argon atmosphere, a reaction vessel was charged with 37.1 g (100 mmol) of compound H-6-A, 19.9 g (100 mmol) of compound H-6-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(dibenzylideneacetonepalladium), 953 mg (2 mmol%) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 ml of water was added, and the mixture was filtered. The filter cake was washed with a large amount of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 34.3 g of compound H-6-1 with an HPLC purity of 99.3% and a yield of 70%. LC MS: M / Z 489.21 (M+).

[0104] 1 H NMR(500MHz,DMSO-d6)δ8.31(m,1H),7.96(d,1H),7.90–7.82(m,2H),7.72(d,1H),7.62–7.57(m,2H) ,7.49(m,1H),7.46–7.39(m,2H),7.23(m,1H),7.18(m,1H),7.02(d,1H),1.59(s,6H),1.55(s,12H).

[0105] 2) Synthesis of compound H-6

[0106] Under an argon atmosphere, a reaction vessel was charged with 49.0 g (100 mmol) of compound H-6-1, 30.7 g (100 mmol) of compound H-6-C, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(dibenzylideneacetonepalladium), 953 mg (2 mmol%) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 ml of water was added, and the mixture was filtered. The filter cake was washed with a large amount of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 48.7 g of compound H-6-1 with an HPLC purity of 99.9% and a yield of 60%. LC MS: M / Z 715.29 (M+).

[0107] 1 H NMR(500MHz,DMSO-d6)δ8.33–8.27(m,2H),8.05(d,1H),7.99(m,2H),7.80(m,2H),7.71(d,1H),7.62–7.50(m,9H) ,7.49(m,1H),7.44–7.37(m,2H),7.29(m,1H),7.25(m,1H),7.15(m,1H),7.05(d,1H),1.60(s,6H),1.56(d,12H).

[0108] Example 2

[0109] Synthesis of compound H-11

[0110]

[0111] The reaction was the same as in Example 1 except that the starting materials were replaced with H-11-A, H-11-B, and H-11-C. LCMS: M / Z 913.39 (M+). Total yield: 41%; HPLC purity: 99.9%.

[0112] 1 H NMR(500MHz,DMSO-d6)δ7.89–7.82(m,2H),7.69(d,1H),7.55–7.43(m,6H),7.42(s,1H),7.40– 7.32(m,2H),7.31–7.18(m,14H),7.16–7.02(m,10H),6.99(m,2H),6.84(d,1H),1.56(s,12H).

[0113] Example 3

[0114] Synthesis of compound H-15

[0115]

[0116] The reaction was the same as in Example 1 except that the starting materials were replaced with H-15-A, H-15-B, and H-15-C. LCMS: M / Z 747.31 (M+). Total yield: 39%; HPLC purity: 99.9%.

[0117] 1H NMR(500MHz,DMSO-d6)δ8.01(m,1H),7.92(d,1H),7.84(m,2H),7.71(d,1H),7.69–7.63(m,2H),7.60–7.52(m,3H),7.51–7.24(m,1 2H),7.20–7.14(m,2H),7.11(d,1H),6.96(d,J=1.6Hz,1H),6.87(dd,J=7.4,1.6Hz,1H),6.83–6.77(m,2H),1.56(d,J=1.1Hz,12H).

[0118] Example 4

[0119] Synthesis of compound H-18

[0120]

[0121] The reaction was the same as in Example 1 except that the starting materials were replaced with H-18-A, H-18-B, and H-18-C. LCMS: M / Z 913.39 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0122] 1 H NMR(500MHz,DMSO-d6)δ7.84(m,1H),7.72(m,2H),7.68–7.63(m,2H),7.57–7.51(m,2H) ,7.46–7.32(m,7H),7.32–7.10(m,20H),7.04(m,2H),7.01–6.96(m,3H),1.56(d,12H).

[0123] Example 5

[0124] Synthesis of compound H-21

[0125]

[0126] The reaction was the same as in Example 1 except that the starting materials were replaced with H-21-A, H-21-B, and H-21-C. LCMS: M / Z 865.39 (M+). Total yield: 38%; HPLC purity: 99.9%.

[0127] 1 H NMR(500MHz,DMSO-d6)δ7.90–7.82(m,2H),7.71–7.63(m,3H),7.61(m,1H),7.54(m,4H),7.48(m,1H),7.46–7 .31(m,7H),7.31–7.15(m,11H),7.05(m,2H),6.99(m,2H),6.84(d,J=1.4Hz,1H),1.61(s,6H),1.56(s,12H).

[0128] Example 6

[0129] Synthesis of compound H-26

[0130]

[0131] The reaction was the same as in Example 1 except that the starting materials were replaced with H-26-A, H-26-B, and H-26-C. LCMS: M / Z 724.31 (M+). Total yield: 38%; HPLC purity: 99.9%.

[0132] 1 H NMR(500MHz,DMSO-d6)δ8.21(d,1H),8.13(m,1H),7.82(m,1H),7.78(m,2H),7.63–7.40(m,15 H),7.40–7.32(m,2H),7.34–7.26(m,2H),7.26–7.20(m,2H),7.20–7.15(m,3H),1.56(s,12H).

[0133] Example 7

[0134] Synthesis of compound H-33

[0135]

[0136] The reaction was the same as in Example 1 except that the starting materials were replaced with H-33-A, H-33-B, and H-33-C. LCMS: M / Z 747.26 (M+). Total yield: 39%; HPLC purity: 99.9%.

[0137] 1H NMR(500MHz,DMSO-d6)δ8.30(m,1H),7.98(m,2H),7.84(d,1H),7.81(m,1H),7.75–7.62(m,5H),7 .59(d,1H),7.57–7.30(m,8H),7.22–7.15(m,3H),7.18–7.11(m,1H),1.59(s,6H),1.56(s,12H).

[0138] Example 8

[0139] Synthesis of compound H-36

[0140]

[0141] The reaction was the same as in Example 1 except that the starting materials were replaced with H-36-A, H-36-B, and H-36-C. LCMS: M / Z 929.37 (M+). Total yield: 39%; HPLC purity: 99.9%.

[0142] 1 H NMR(500MHz,DMSO-d6)δ7.93(m,1H),7.84(m,3H),7.81–7.76(m,1H),7.75–7.66(m,5H),7.64–7.59(m,1H),7.58(t,1H),7.53( t,1H),7.44(m,2H),7.40–7.25(m,12H),7.22(m,2H),6.94(d,1H),6.85–6.79(m,2H),6.75(m,2H),1.59(s,6H),1.56(s,12H).

[0143] Example 9

[0144] Synthesis of compound H-41

[0145]

[0146] The reaction was the same as in Example 1 except that the starting materials were replaced with H-41-A, H-41-B, and H-41-C. LCMS: M / Z 740.34 (M+). Total yield: 38%; HPLC purity: 99.9%.

[0147] 1H NMR(500MHz,DMSO-d6)δ8.10(m,1H),8.03(m,2H),7.91(d,1H),7.65–7.58(m,2H),7.58–7.38(m,12H),7.37–7.32(m ,2H),7.28(m,1H),7.20(m,1H),7.08–6.99(m,2H),6.87(m,1H),2.30–2.13(m,4H),1.94–1.82(m,4H),1.56(s,12H).

[0148] Example 10

[0149] Synthesis of compound H-50

[0150]

[0151] The reaction was the same as in Example 1 except that the starting materials were replaced with H-50-A, H-50-B, and H-50-C. LCMS: M / Z 1062.46 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0152] 1 H NMR(500MHz,DMSO-d6)δ8.30(m,1H),7.97(d,1H),7.83(m,2H),7.69(d,1H),7.6 3–7.57(m,3H),7.52–7.45(m,2H),7.47–7.37(m,3H),7.39–7.32(m,2H),7.32–7. 03(m,18H),7.00(m,2H),6.85(d,1H),2.90(m,1H),2.44–2.33(m,2H),2.33–2.2 1(m,2H),2.19(m,1H),1.95–1.86(m,1H),1.75–1.55(m,9H),1.55–1.41(m,10H).

[0153] Example 11

[0154] Synthesis of compound H-51

[0155]

[0156] The reaction was the same as in Example 1 except that the starting materials were replaced with H-51-A, H-51-B, and H-51-C. LCMS: M / Z 835.29 (M+). Total yield: 39%; HPLC purity: 99.9%.

[0157] 1H NMR(500MHz,DMSO-d6)δ8.30(m,1H),7.97(d,1H),7.84(m,1H),7.81(m,1H),7.76(d,1H),7.73–7.67(m,3H),7.60(d,1H),7 .48(m,2H),7.42(m,1H),7.36(m,1H),7.31–7.17(m,9H),7.05(m,2H),6.98(m,3H),6.84(d,1H),1.56(s,11H),0.47(s,6H).

[0158] Example 12

[0159] Synthesis of compound H-54

[0160]

[0161] The reaction was the same as in Example 1 except that the starting materials were replaced with H-54-A, H-54-B, and H-54-C. LCMS: M / Z 1000.38 (M+). Total yield: 39%; HPLC purity: 99.9%.

[0162] 1 H NMR(500MHz,DMSO-d6)δ8.10(m,1H),8.04(d,1H),7.92(m,2H),7.84(m,3H),7.78(d,1H),7.75(s,1H),7.73–7 .67(m,2H),7.64–7.47(m,6H),7.47–7.19(m,18H),7.16(m,1H),6.87(m,1H),6.85–6.78(m,3H),1.56(s,12H).

[0163] Example 13

[0164] Synthesis of compound H-61

[0165]

[0166] The reaction was carried out as in Example 1 except that the starting materials were replaced with H-61-A and H-61-B. LC MS: M / Z 610.31 (M+). Total yield: 60%; HPLC purity: 99.9%.

[0167] 1H NMR(500MHz,DMSO-d6)δ7.84(m,6H),7.71(m,3H),7.58(s,1H),7.40(s,1H),7.38–7.23(m,13H),7.20(m ,2H),6.98(d,1H),6.88–6.79(m,8H),3.31(m,2H),2.01–1.89(m,7H),1.75–1.61(m,6H),1.56(s,12H).

[0168] Example 14

[0169] Synthesis of compound E-2

[0170]

[0171] Under an argon atmosphere, a reaction vessel was charged with 37.1 g (100 mmol) of compound E-2-A, 40.3 g (100 mmol) of compound E-2-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(dibenzylideneacetonepalladium), 953 mg (2 mmol%) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 ml of water was added, and the mixture was filtered. The filter cake was washed with a large amount of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 43.5 g of compound E-2 with an HPLC purity of 99.9% and a yield of 61%. LC MS: M / Z 649.31 (M+).

[0172] 1 H NMR(500MHz,DMSO-d6)δ8.38(m,2H),8.08–8.04(m,1H),7.98–7.84(m,5H),7.73–7. 64(m,4H),7.62(d,1H),7.54–7.42(m,7H),7.37(s,1H),1.59(s,6H),1.55(d,12H).

[0173] Example 15

[0174] Synthesis of compound E-6

[0175]

[0176] The reaction was carried out as in Example 14 except that the starting materials were replaced with E-6-A and E-6-B. LC MS: M / Z 599.29 (M+). Total yield: 59%; HPLC purity: 99.9%.

[0177] 1 H NMR (500MHz, DMSO-d6) δ8.41–8.34(m,4H),7.88–7.80(m,3H),7.70–7.64(m,2H),7.59(m,1H),7.51–7.39(m,10H),1.60(s,6H),1.55(s,12H).

[0178] Example 16

[0179] Synthesis of compound E-9

[0180]

[0181] The reaction was carried out as in Example 14 except that the starting materials were replaced with E-9-A and E-9-B. LC MS: M / Z 523.26 (M+). Total yield: 61%; HPLC purity: 99.9%.

[0182] 1 H NMR (500MHz, DMSO-d6) δ8.41–8.34(m,4H),7.74(m,1H),7.62(t,1H),7.52–7.43(m,8H),7.21(s,1H),1.60(s,6H),1.55(s,12H).

[0183] Example 17

[0184] Synthesis of compound E-14

[0185]

[0186] Except that the starting materials were replaced with E-14-A and E-14-B, the rest was the same as Example 14. LC MS: M / Z

[0187] 787.32 (M+). Total yield of synthesis: 59%; HPLC purity: 99.9%.

[0188] 1 H NMR(500MHz,DMSO-d6)δ8.42–8.34(m,2H),8.20(m,1H),8.07(d,1H),7.96–7.88(m,2H),7.82(d,1H),7.71–7.64(m ,4H),7.57–7.46(m,3H),7.50–7.39(m,5H),7.31–7.24(m,4H),7.25–7.18(m,2H),7.11–7.05(m,4H),1.56(s,12H).

[0189] Example 18

[0190] Synthesis of compound E-21

[0191]

[0192] The reaction was carried out as in Example 1 except that the starting materials were replaced with E-21-A and E-21-B. LC MS: M / Z 647.29 (M+). Total yield: 59%; HPLC purity: 99.9%.

[0193] 1 H NMR(500MHz,DMSO-d6)δ8.38(m,4H),7.72(m,1H),7.63(t,1H),7.49(s,1H),7.49–7.42(m,6H ),7.42–7.37(m,2H),7.31–7.24(m,4H),7.27–7.18(m,2H),7.12–7.06(m,4H),1.55(s,12H).

[0194] Example 19

[0195] Synthesis of compound E-28

[0196]

[0197] Except that the starting materials were replaced with E-28-A and E-28-B, the rest was the same as Example 14. LC MS: M / Z

[0198] 721.31 (M+). Total yield: 62%; HPLC purity: 99.9%.

[0199] 1 H NMR(500MHz,DMSO-d6)δ8.41–8.34(m,4H),7.89–7.80(m,5H),7.70–7.65(m,2H),7.63(m, 1H),7.51(d,1H),7.49–7.40(m,8H),7.36–7.25(m,4H),6.83–6.78(m,2H),1.56(s,12H).

[0200] Example 20

[0201] Synthesis of compound E-41

[0202]

[0203] Except that the starting materials were replaced with E-28-A and E-28-B, the rest was the same as Example 14. LC MS: M / Z

[0204] 547.23 (M+). Total yield: 59%; HPLC purity: 99.9%.

[0205] 1 H NMR(500MHz,DMSO-d6)δ9.05(t,1H),8.49(m,1H),8.41–8.34(m,2H),8.11(d,1H),8.08–7 .97(m,3H),7.89–7.84(m,1H),7.61(s,1H),7.56–7.43(m,7H),7.28(s,1H),1.56(s,12H).

[0206] Example 21

[0207] Synthesis of compound E-44

[0208]

[0209] Except that the starting materials were replaced with E-44-A and E-44-B, the rest was the same as Example 14. LC MS: M / Z

[0210] 679.23 (M+). Total yield of synthesis: 57%; HPLC purity: 99.9%.

[0211] 1 H NMR(500MHz,DMSO-d6)δ8.51(d,1H),8.41–8.34(m,4H),8.12(d,1H),7.94(d,1H),7.8 9(d,1H),7.73–7.65(m,5H),7.64(d,1H),7.55(m,1H),7.50–7.42(m,6H),1.56(s,12H)

[0212] Example 22

[0213] Synthesis of compound E-45

[0214]

[0215] Except that the starting materials were replaced with E-45-A and E-45-B, the rest was the same as Example 14. LC MS: M / Z

[0216] 722.30 (M+). Total yield of synthesis: 58%; HPLC purity: 99.9%.

[0217] 1H NMR(500MHz,DMSO-d6)δ9.73–9.69(m,1H),8.41–8.34(m,2H),8.30(m,2H),8.10(m,1H),8.02( m,1H),7.97(d,1H),7.90(s,1H),7.82(m,1H),7.73(s,1H),7.65–7.41(m,16H),1.57(s,12H).

[0218] Example 23

[0219] Synthesis of compound E-49

[0220]

[0221] Except that the starting materials were replaced with E-49-A and E-49-B, the rest was the same as Example 14. LC MS: M / Z

[0222] 773.34 (M+). Total yield: 58%; HPLC purity: 99.9%.

[0223] 1H NMR (500MHz, DMSO-d6) δ9.73–9.69(m,1H),8.41–8.34(m,2H),8.30(dd,J=7.2,1.5Hz,2H),8.10(dd,J=7.5,1.6Hz,1H),8.02(dd,J=6.3 ,2.7Hz,1H),7.97(d,J=7.5Hz,1H),7.90(s,1H),7.82(dd,J=7.2,1.8Hz,1H),7.73(s,1H),7.65–7.41(m,16H),1.57(d,J=2.9Hz,12H).

[0224] Example 24

[0225] Synthesis of compound E-57

[0226]

[0227] The reaction was carried out as in Example 1 except that the starting materials were replaced with E-57-A and E-57-B. LC MS: M / Z 563.75 (M+). Total yield: 59%; HPLC purity: 99.9%.

[0228] 1H NMR(500MHz,DMSO-d6)δ8.42–8.34(m,4H),7.74(m,1H),7.59(t,1H),7.51–7.44(m,7H),7 .47–7.39(m,2H),2.26–2.10(m,4H),1.76–1.61(m,4H),1.55(s,12H),1.53–1.37(m,2H).

[0229] Example 25

[0230] Synthesis of compound E-60

[0231]

[0232] Except that the starting materials were replaced with E-60-A and E-60-B, the rest was the same as Example 14. LC MS: M / Z

[0233] 817.40 (M+). Total yield of synthesis: 59%; HPLC purity: 99.9%.

[0234] 1 H NMR(500MHz,DMSO-d6)δ8.41–8.34(m,2H),7.97–7.92(m,2H),7.92–7.83(m,5H),7.87–7.79(m,1H),7.71–7.64(m,5H),7.63(m,1H ),7.59–7.50(m,2H),7.50–7.41(m,5H),7.41–7.36(m,2H),3.31(m,2H),2.02–1.86(m,6H),1.69(m,4H),1.64(t,2H),1.56(s,12H)

[0235] Example 26

[0236] Synthesis of compound E-69

[0237]

[0238] Except that the starting materials were replaced with E-69-A and E-69-B, the rest was the same as Example 14. LC MS: M / Z

[0239] 737.29 (M+). Total yield: 58%; HPLC purity: 99.9%.

[0240] 1H NMR(500MHz,DMSO-d6)δ8.42–8.34(m,4H),8.17(m,1H),8.06(m,1H),7.92(m,2H),7.81–7.75(m, 2H),7.72(s,1H),7.68(s,1H),7.65–7.52(m,6H),7.48–7.41(m,6H),7.38(m,2H),1.56(s,12H).

[0241] Example 27

[0242] Synthesis of compound D-1

[0243]

[0244] 1) Synthesis of intermediate D-1-1

[0245] Under an argon atmosphere, a reaction vessel was charged with 30.0 g (100 mmol) of compound 1-A, 31.2 g (100 mmol) of compound 1-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(dibenzylideneacetonepalladium), 953 mg (2 mmol%) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 ml of water was added, and the mixture was filtered. The filter cake was washed with a large amount of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 37.1 g of compound D-1-1 with an HPLC purity of 99.1% and a yield of 70%. LC MS: M / Z 530.19 (M+).

[0246] 1 H NMR (500MHz, DMSO-d6) δ8.42–8.34(m,4H),8.10(d,1H),7.93(s,1H),7.80(s,1H),7.51–7.40(m,7H),7.31(d,1H),1.55(s,12H).

[0247] 2) Synthesis of Compound D-1

[0248] Under an argon atmosphere, a reaction vessel was charged with 53.1 g (100 mmol) of compound D-1, 22.2 g (100 mmol) of compound D-1-C, 787 mg (1 mmol%) of XPhos Pd G3, 50 ml (300 mmol) of 1.5 M potassium phosphate, and 1000 ml of tetrahydrofuran (THF). The mixture was stirred under reflux overnight. After cooling to room temperature, 800 ml of water was added. A large amount of solid precipitated and was filtered. The filter cake was washed three times with water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 40.4 g of compound D-1, a 60% yield with an HPLC purity of 99.9%. LC-MS: M / Z 672.79 (M+).

[0249] 1 H NMR(500MHz,DMSO-d6)δ8.44(d,J=7.5Hz,1H),8.41–8.34(m,4H),8.21(m,1H),8.13(m,1H),8.07–7.99(m,2H), 7.95(s,1H),7.83(m,1H),7.81–7.75(m,2H),7.61(m,2H),7.58–7.48(m,3H),7.48–7.40(m,6H),1.56(d,12H).

[0250] Example 28

[0251] Synthesis of compound D-8

[0252]

[0253] The reaction was carried out as in Example 27 except that the starting materials were replaced with D-8-A, D-8-B, and D-8-C. LCMS: M / Z 784.36 (M+). Total yield: 35%; HPLC purity: 99.9%.

[0254] 1 H NMR(500MHz,DMSO-d6)δ8.44(m,2H),8.41–8.32(m,7H),7.93–7.87(m,2H),7.71(s,1H) ,7.68–7.61(m,5H),7.60(s,1H),7.52–7.40(m,13H),7.40–7.33(m,1H),1.57(s,12H).

[0255] Example 29

[0256] Synthesis of compound D-12

[0257]

[0258] The reaction was the same as in Example 27 except that the starting materials were replaced with D-12-A, D-12-B, and D-12-C. LCMS: M / Z 828.97 (M+). Total yield: 41%; HPLC purity: 99.9%.

[0259] 1 H NMR(500MHz,DMSO-d6)δ8.45–8.34(m,4H),8.04(m,2H),7.97(m,1H),7.96(s,1H),7.88(m,2H),7.81(s,1H),7.74(d ,1H),7.68–7.58(m,4H),7.60–7.50(m,3H),7.49–7.42(m,4H),7.46–7.37(m,2H),7.41–7.33(m,3H),1.56(s,12H).

[0260] Example 30

[0261] Synthesis of compound D-23

[0262]

[0263] The reaction was the same as in Example 1 except that the starting materials were replaced with D-23-A, D-23-B, and D-23-C. LCMS: M / Z 661.31 (M+). Total yield: 41%; HPLC purity: 99.9%.

[0264] 1 H NMR(500MHz,DMSO-d6)δ8.09(m,1H),7.90(s,1H),7.88–7.82(m,2H),7.80–7.70(m,5H),7.67(m,2H ),7.63(m,1H),7.60–7.53(m,2H),7.52–7.39(m,4H),7.43–7.31(m,3H),1.59(s,6H),1.56(s,12H).

[0265] Example 31

[0266] Synthesis of compound D-32

[0267]

[0268] The reaction was the same as in Example 27 except that the starting materials were replaced with D-32-A, D-32-B, and D-32-C. LCMS: M / Z 633.24 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0269] 1 H NMR(500MHz,DMSO-d6)δ8.19(t,1H),8.14–8.08(m,3H),7.93–7.86(m,3H),7.73–7.68(m,2H),7.67–7.53(m,7H),7.53–7.40(m,3H),1.56(s,12H)

[0270] Example 32

[0271] Synthesis of compound D-35

[0272]

[0273] The reaction was the same as in Example 27 except that the starting materials were replaced with D-35-A, D-35-B, and D-35-C. LCMS: M / Z 793.31 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0274] 1 H NMR(500MHz,DMSO-d6)δ7.98–7.93(m,2H),7.93–7.75(m,8H),7.75–7.68(m,3H) ,7.68–7.59(m,3H),7.47–7.30(m,8H),7.27(m,1H),1.59(s,6H),1.56(s,12H).

[0275] Example 33

[0276] Synthesis of compound D-38

[0277]

[0278] The reaction was the same as in Example 27 except that the starting materials were replaced with D-38-A, D-38-B, and D-38-C. LCMS: M / Z 849.34 (M+). Total yield: 43%; HPLC purity: 99.9%.

[0279] 1 H NMR(500MHz,DMSO-d6)δ8.55(m,1H),8.13(d,1H),8.02(m,1H),7.94(s,1H),7.92–7.84(m,3H),7.82–7.74 (m,3H),7.69–7.53(m,7H),7.46–7.32(m,4H),7.27(m,4H),7.13(m,2H),7.07–6.96(m,4H),1.56(s,12H).

[0280] Example 34

[0281] Synthesis of compound D-39

[0282]

[0283] The reaction was the same as in Example 1 except that the starting materials were replaced with D-39-A, D-39-B, and D-39-C. LCMS: M / Z 751.28 (M+). Total yield: 43%; HPLC purity: 99.9%.

[0284] 1 H NMR(500MHz,DMSO-d6)δ8.40(m,1H),8.10–8.01(m,2H),7.94(s,1H),7.89(d,1H),7.83–7.75(m,4H),7.73–7.67(m ,2H),7.64–7.52(m,6H),7.52–7.45(m,3H),7.47–7.40(m,2H),7.44–7.37(m,2H),7.40–7.33(m,1H),1.56(s,12H).

[0285] Example 35

[0286] Synthesis of compound D-46

[0287]

[0288] The reaction was the same as in Example 1 except that the starting materials were replaced with D-46-A, D-46-B, and D-46-C. LCMS: M / Z 707.21 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0289] 1 H NMR(500MHz,DMSO-d6)δ8.37–8.31(m,1H),8.24(d,J=7.6Hz,1H),8.06–8.02(m,1H),7.98–7.92(m,2H),7.80(s,2H),7.84– 7.76(m,2H),7.73(m,1H),7.70–7.62(m,3H),7.50(m,1H),7.46–7.36(m,4H),7.39–7.32(m,1H),7.28(m,1H),1.56(s,12H).

[0290] Example 36

[0291] Synthesis of compound D-51

[0292]

[0293] The reaction was the same as in Example 1 except that the starting materials were replaced with D-51-A, D-51-B, and D-51-C. LCMS: M / Z 889.33 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0294] 1 H NMR(500MHz,DMSO-d6)δ8.46(d,1H),8.31(d,1H),8.09(m,1H),8.00(m,1H),7.95(s,1H),7.92–7.71(m,7H),7.65(m,1H), 7.61–7.52(m,2H),7.52–7.40(m,3H),7.39–7.32(m,2H),7.32–7.22(m,4H),7.13(m,2H),7.07–6.96(m,4H),1.56(s,12H).

[0295] Example 37

[0296] Synthesis of compound D-53

[0297]

[0298] The same procedure as in Example 1 was used except that the starting materials were replaced with D-53-A, D-53-B, and D-53-C. LCMS: M / Z 710.30 (M+). Total yield: 43%; HPLC purity: 99.9%.

[0299] 1 H NMR(500MHz,DMSO-d6)δ8.41(m,1H),8.12–8.06(m,2H),7.95(s,1H),7.86(m, 1H),7.81–7.73(m,5H),7.69–7.38(m,14H),7.32–7.23(m,2H),1.56(s,12H).

[0300] Example 38

[0301] Synthesis of compound D-57

[0302]

[0303] The reaction was the same as in Example 1 except that the starting materials were replaced with D-57-A, D-57-B, and D-57-C. LCMS: M / Z 707.29 (M+). Total yield: 40%; HPLC purity: 99.9%.

[0304] 1H NMR(500MHz,DMSO-d6)δ8.15(m,3H),7.87–7.80(m,2H),7.74(s,1H),7.68(m,1H),7.68–7.61(m,2H),7.53(s, 1H),7.48(t,1H),7.43(m,1H),7.39(d,1H),7.36(m,1H),7.33–7.19(m,7H),7.17–7.11(m,4H),1.57(s,12H).

[0305] Example 39

[0306] Synthesis of compound D-59

[0307]

[0308] The reaction was the same as in Example 1 except that the starting materials were replaced with D-59-A, D-59-B, and D-59-C. LCMS: M / Z 924.38 (M+). Total yield: 43%; HPLC purity: 99.9%.

[0309] 1 H NMR(500MHz,DMSO-d6)δ8.57–8.51(m,1H),8.46(d,1H),8.31(d,1H),8.09(m,1H),7.97–7. 88(m,2H),7.87–7.82(m,1H),7.82–7.78(m,2H),7.77(d,1H),7.71–7.63(m,3H),7.59(m,1H ),7.53–7.44(m,4H),7.44–7.37(m,1H),7.40–7.33(m,1H),7.36–7.25(m,4H),7.27(d,1H) ,7.28–7.22(m,1H),7.25–7.18(m,2H),7.15–7.04(m,6H),7.03–6.97(m,2H),1.56(s,12H).

[0310] Device Example 1: Preparation of an organic electroluminescent device

[0311]

[0312] The preparation process is as follows:

[0313] 1) A transparent anode ITO film layer (thickness 150 nm) was formed on a glass substrate to obtain a first electrode as an anode.

[0314] 2) A mixed material of Compound T-1 and Compound T-2 was evaporated on the surface of the anode by vacuum evaporation as a hole injection layer with a mixing ratio (mass ratio) of 3:97 and a thickness of 10 nm.

[0315] 3) Compound T-2 was evaporated on the hole injection layer to a thickness of 100 nm to obtain a first hole transport layer. Then, compound H-6 of the present invention was evaporated on the first hole transport layer to a thickness of 10 nm to obtain a second hole transport layer.

[0316] 4) On the second hole transport layer, compound T-3 and compound T-4 were co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer with a thickness of 40 nm.

[0317] 5) On the organic light-emitting layer, compound T-5 was evaporated in sequence to form a hole blocking layer (thickness 10 nm), and compound T-6 and LiQ with a mixing ratio of 4:6 (mass ratio) formed an electron transport layer (thickness 30 nm).

[0318] 6) Mix magnesium (Mg) and silver (Ag) at an evaporation rate of 1:9 and vacuum evaporate them onto the electron injection layer serving as the second electrode, thereby completing the fabrication of the organic light-emitting device.

[0319] Device Examples 2-13

[0320] An organic electroluminescent device was prepared by the same method as in Device Example 1, except that compounds H-11, H-15, H-18, H-21, H-26, H-33, H-36, H-41, H-50, H-51, H-54 and H-61 were used instead of compound H-6 when forming the second hole transport layer.

[0321] Device Comparative Examples 1-2

[0322] An organic electroluminescent device was prepared by the same method as in Device Example 1, except that Compound HT-1 and Compound HT-2 were used instead of Compound H-6 when forming the second hole transport layer.

[0323] Each of the above device embodiments and device comparative example 1 were produced and tested in the same batch as the devices of device comparative example 2. The operating voltage, efficiency, and life of the devices of device comparative example 1 were each recorded as 1, and the ratios of the corresponding indicators of device embodiments 1-20 and the device comparative examples to device comparative example 1 were calculated, as shown in Table 1.

[0324] Table 1 Test results of device embodiments 1 to 13 and device comparative examples 1 to 2

[0325]

[0326]

[0327] According to the results in Table 1, when used as the second hole transport layer of the light-emitting device, the compounds used in device Examples 1 to 13 have lower voltages, higher luminous efficiencies, and significantly improved lifespans compared to the devices formed by the compounds used in device Comparative Examples 1 to 2.

[0328] Device Example 14: Preparation of an organic electroluminescent device

[0329]

[0330] A glass substrate coated with indium tin oxide (ITO) having a thickness of 100 nm as a thin film was placed in distilled water dissolved with a detergent and subjected to ultrasonic cleaning. After cleaning the ITO for 20 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each time. After washing with distilled water, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol, then dried and transferred to a plasma cleaner. In addition, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum depositor. On the transparent ITO electrode prepared as above, a hole injection layer was formed by thermal vacuum deposition of compound HI at a deposition rate of 0.04 to 0.09 nm / s and a total film thickness of 60 nm.

[0331] 1) Compound HAT was vacuum-deposited on the hole injection layer as a first hole transport layer at a deposition rate of 0.04-0.09 nm / s and a total deposition thickness of 5 nm.

[0332] 2) Vacuum-deposit HT on the first hole transport layer as a second hole transport layer at a deposition rate of 0.04-0.09 nm / s and a total deposition thickness of 50 nm.

[0333] 3) A light-emitting layer was formed on the second hole transport layer by vacuum evaporation of compound BH and compound BD at a weight ratio of 25:1. The evaporation rate was 0.04 to 0.09 nm / s, and the total film thickness was 20 nm.

[0334] 4) On the light-emitting layer, an electron transport layer and an injection layer were formed by vacuum evaporating compound E-2 and compound LiQ at a weight ratio of 1:1. The evaporation rate was 0.1 nm / s, and the total film thickness was 35 nm.

[0335] 5) Lithium fluoride (LiF) was deposited on the electron injection and transport layer at a deposition rate of 0.03 nm / s to a total thickness of 1 nm, and then aluminum was deposited at a deposition rate of 0.2 nm / s to a total thickness of 100 nm to form a cathode.

[0336] During this process, the vacuum degree is maintained at 1*10 -7 to 5*10 -5Entrust.

[0337] Device Examples 15-26

[0338] An organic electroluminescent device was prepared by the same method as in device example 14, except that compounds E-6, E-9, E-14, E-21, E-28, E-41, E-44, E-45, E-49, E-57, E-60 and E-69 were used instead of compound E-2 when forming the electron transport layer.

[0339] Device Comparison Examples 3-4

[0340]

[0341] An organic electroluminescent device was prepared by the same method as in Device Example 14, except that Compound ET1 and ET2 were used instead of Compound E-2 when forming the light-emitting layer.

[0342] Each of the above device embodiments and device comparative example 3 were produced and tested in the same batch as the devices of device comparative example 4. The operating voltage, efficiency, and life of the devices of device comparative example 3 were each recorded as 1, and the ratios of the corresponding indicators of device embodiments 14-26 and the device comparative examples to those of device comparative example 1 were calculated, as shown in Table 2.

[0343] Table 2 Test results of device examples 14 to 26 and device comparative examples 3 to 4

[0344]

[0345]

[0346] According to the results in Table 2, when the series of compounds of the present invention replace the commercialized electron transport materials ET1 and ET2 in device comparative examples 3 and 4 as the electron transport layer of the light-emitting device, the voltage is reduced and the current efficiency is improved. The above results show that the new organic material of the present invention is an organic light-emitting functional material with good performance as an electron transport material for organic electroluminescent devices and is expected to be promoted for commercial application.

[0347] Device Example 27: Preparation of an organic electroluminescent device

[0348]

[0349] The basic structural model of the organic optoelectronic device is: ITO / HAT-CN (10 nm) / TAPC (40 nm) / TCTA (10 nm) / EML (compound of the present invention): RD (Ir complex) = 94:6 (40 nm) / ETL (30 nm) / LiF (1 nm) / Al (80 nm).

[0350] The manufacturing method of the organic optoelectronic device of this embodiment:

[0351] (1) A transparent anodized indium tin oxide (ITO) 20 (10Ω / sq) glass substrate was ultrasonically cleaned with acetone, ethanol, and distilled water in sequence, and then treated with ozone plasma for 15 minutes.

[0352] (2) After installing the ITO substrate on the substrate holder of the vacuum vapor deposition equipment, control the system pressure at 10 -6 Then, HAT-CN with a thickness of 10 nm, TAPC with a thickness of 40 nm and TCTA with a thickness of 10 nm were sequentially evaporated onto the ITO substrate.

[0353] (3) A 40 nm thick emitting layer (EML) was deposited on the TCTA, wherein the mass ratio of the compound D-1 of the present invention to RD was 94:6. Compound D-1 was the host material of the emitting layer.

[0354] (4) An electron transport layer (ETL) material was evaporated on the light emitting layer to a thickness of 30 nm.

[0355] (5) LiF was evaporated to a thickness of 1 nm on the electron transport layer as an electron injection layer.

[0356] (6) Finally, Al with a thickness of 80 nm was evaporated on the electron injection layer as a cathode, and the device was encapsulated with a glass encapsulation cover.

[0357] Device Examples 28-39

[0358] An organic electroluminescent device was prepared by the same method as in device example 25, except that compounds D-8, D-12, D-23, D-32, D-35, D-38, D-39, D-46, D-51, D-53, D-57 and D-59 were used instead of compound D-1 when forming the light-emitting layer.

[0359] Device Comparative Examples 5-6

[0360] An organic electroluminescent device was prepared by the same method as in Device Example 27, except that Compound RH-01 and Compound RH-02 were used instead of Compound D-1 when forming the light-emitting layer.

[0361] Each of the above device examples and device comparative example 5 were produced and tested in the same batch as the devices of device comparative example 6. The current efficiency and LT98 (hr) relative values of the devices of device comparative example 5 were both recorded as 1. The ratios of the corresponding indicators of device examples 27-39 and the device comparative examples to those of device comparative example 1 were calculated, as shown in Table 3.

[0362] Table 3 Test results of device examples 27 to 39 and device comparative examples 5 to 6

[0363]

[0364]

[0365] According to the results in Table 3, when used as the light-emitting layer of a light-emitting device, the compounds used in device embodiments 27 to 39 have improved luminous efficiency and significantly improved lifespan compared to the devices formed by the compounds used in device comparison examples 5 to 6.

[0366] Accordingly, the device structures in the above embodiments and comparative examples are identical except for the corresponding functional layers. Based on the device performance of the comparative materials, the current efficiency of the device containing the compound of the present invention has been significantly improved, and its lifespan has also been improved. The above results show that the new organic material of the present invention is an organic light-emitting functional material with good performance and is expected to be promoted for commercial application.

[0367] The above description is only a preferred specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any technician familiar with the technical field, within the technical scope disclosed by the present invention, who makes equivalent replacements or changes based on the technical solution and inventive concept of the present invention, should be covered by the scope of protection of the present invention.

Claims

1. A compound, the chemical structure of which is shown in formula (I): in: R1-R4 are the same or different and are independently selected from hydrogen, substituted or unsubstituted phenyl, biphenyl, The substituted substituent is phenyl; at least one of R1-R4 is selected from the following structures: L1 to L6 are each independently selected from a single bond, phenylene, naphthylene, dibenzofuranylene; Ar1 to Ar4 are each independently selected from phenyl, biphenyl, naphthyl, E is selected from 1,3,5-triazine; R5-R8 are each independently selected from methyl or deuterated methyl; A is selected from NR 13 , O, or S or any one of the following groups: R 13 Selected from phenyl, * is the atomic attachment site.

2. A compound, characterized in that The compound is selected from any one of the following chemical structures:

3. An organic layer comprising the compound according to any one of claims 1 to 2.

4. Use of the compound according to any one of claims 1 to 2 and / or the organic layer according to claim 3 in an organic optoelectronic device.

5. An organic photoelectric device comprising a first electrode, a second electrode and the organic layer according to claim 3, wherein: The organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer.

6. The organic optoelectronic device according to claim 5, wherein The organic photoelectric device is an organic photovoltaic device, an organic light-emitting device, an organic photoreceptor, or an organic thin film transistor.

7. The organic optoelectronic device according to claim 6, wherein The organic photoelectric device is an organic solar cell.

8. A display or lighting device comprising the organic optoelectronic device according to any one of claims 5 to 7.

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