CN112625032A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN112625032A
CN112625032A CN202011120764.6A CN202011120764A CN112625032A CN 112625032 A CN112625032 A CN 112625032A CN 202011120764 A CN202011120764 A CN 202011120764A CN 112625032 A CN112625032 A CN 112625032A
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substituted
unsubstituted
aryl
heteroaryl
alkyl
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CN112625032B (en
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陈志宽
李祥智
蔡烨
丁欢达
魏定纬
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Ningbo Lumilan New Material Co ltd
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Abstract

The organic compound has a structure shown in a formula I, has a parent nucleus structure of benzophenanthro [4,5-bcd ] thiophene, and is good in planarity and conjugation, strong in hole and electron transmission capacity, good in thermal stability, long in service life of a prepared device and high in current efficiency.

Description

Organic compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic compound and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) have recently attracted attention due to an increase in demand for flat panel displays. An organic light emitting diode is a device that converts electric energy into light by applying current to an organic light emitting material, and has a structure in which an organic layer is disposed between an anode and a cathode.
The performance of an organic light emitting diode may be influenced by the characteristics of the organic layers and, among other things, mainly by the characteristics of the organic materials of the organic layers. In particular, it is required to develop an organic material capable of improving hole and electron mobility and simultaneously improving electrochemical stability so that the organic light emitting diode can be applied to a large-sized flat panel display.
Disclosure of Invention
In view of the shortcomings of the prior art, the present invention aims to provide an organic compound and its application. The organic compound has benzophenanthro [4,5-bcd ] thiophene group, and has the advantages of good planarity, good conjugation, strong hole and electron transmission capability, good thermal stability, long service life of the prepared device and high current efficiency.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic compound having a structure represented by formula I below:
Figure BDA0002731949470000011
wherein R is1Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, or-L6NAr6Ar7；
Ar6And Ar7Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and adjacent R1Between which is not connected or adjacent to R1Are connected to form a heterocyclic ring containing N;
L6selected from single bond, substituted or unsubstituted aryl of C6-C30; n is an integer of 0 to 4 (e.g., 0, 1,2, 3 or 4)
In the present invention, when one or more groups are simultaneously defined, definitions of the same group at different positions are independent of each other; for example R1The groups are in different positions but are simultaneously defined as "hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, or-L606NAr6 Ar7", then R1The groups may be the same or different at different positions, and are present independently of each other, the same below.
The organic compound has a parent nucleus structure of benzophenanthro [4,5-bcd ] thiophene, so that the organic compound has good planarity and conjugation, strong hole and electron transmission capability, good thermal stability, long service life of a prepared device and high current efficiency.
In the invention, the indolocarbazole structure can further improve the hole transmission capability, balance the hole and electron transmission rates, improve the triplet state energy level and prevent excitons from flowing out of the light-emitting layer.
In the present invention, the heteroaryl group contains at least one atom selected from B, N, O, S, Si or P.
In the present invention, the substituted or unsubstituted alkyl group of C1-C10 is a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10 alkyl group; the substituted or unsubstituted alkenyl group of C2-C10 is a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9 or C10 alkenyl group; the substituted or unsubstituted aryl group of C6-C60 is substituted or unsubstituted aryl group of C6, C7, C8, C10, C12, C15, C18, C20, C25, C28, C30, C33, C35, C40, C45, C50, C55 and C60; the substituted or unsubstituted heteroaryl of C3-C30 is substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9 or C10 heteroaryl.
When the group contains a substituent group, the substituent group refers to that hydrogen atoms in the group are substituted by other groups, and the substituent group is selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, C3-C12 heteroaryl, C3-C12 heteroarylamine, or C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, C3-C12 heteroaryl and C3-C12 heteroaryl, wherein the alkyl is substituted by one or at least two of deuterium, halogen, nitro and cyano;
preferably, when said group contains a substituent, the substituent is selected from any one or at least two of deuterium atom, halogen, cyano, nitro, C1-C4 alkyl, halogen substituted C1-C4 alkyl, deuterium substituted C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, halogen substituted C1-C4 alkenyl, deuterium substituted C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, halogen substituted C6-C12 aryl, deuterium substituted C6-C12 aryl, cyano substituted C6-C12 aryl, C3-C12 heteroaryl, C3-C12 heteroarylamine, halogen substituted C3-C12 heteroaryl or deuterium substituted C3-C12 heteroaryl.
In the present invention, the alkyl group is preferably a C1-C4 alkyl group such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl.
The aryl groups of the present invention include monocyclic, polycyclic, fused ring aromatic groups, which rings may be interrupted by short nonaromatic units such as methylene.
Preferably, the aryl group is preferably selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl or spirobifluorenyl.
The heteroaryl groups of the present invention include monocyclic, polycyclic, fused ring groups, and the rings may be interrupted by short nonaromatic units such as methylene, O, S, N. Preferably, the heteroaryl group is preferably selected from dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthoimidazolyl, naphthooxazolyl, naphthothiazolyl, phenanthroimidazolyl, phenanthroizooxazolyl, phenanthroizothiazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidyl, benzofuropyrazinyl, benzofuropyrimidinyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl, indenopyrimidinyl, spiro (fluorene-9, 1 '-indene) pyrazinyl, spiro (fluorene-9, 1' -indene) pyrimidyl, benzofurocarbazolyl or benzothiophenocarbazolyl.
The adjacent groups form a ring, namely 2-4 substituents at adjacent positions in the same six-membered ring or adjacent six-membered rings can be connected with each other through chemical bonds to form the ring.
Figure BDA0002731949470000021
Indicating an access site, as will appear hereinafter
Figure BDA0002731949470000022
The meaning of the indication is the access point, and is not described in detail later.
Preferably, the organic compound has a structure represented by formula II-1 or formula II-2 below:
Figure BDA0002731949470000023
Figure BDA0002731949470000031
wherein R is1And n is as defined for formula I, Ar5Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl or-L6NAr6 Ar7Wherein Ar is6And Ar7And L6Is as defined in formula I, m is an integer of 0 to 4 (e.g., 0, 1)2, 3 or 4);
L5selected from single bond, substituted or unsubstituted C6-C30 aryl.
R is selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, C3-C12 heteroaryl and C3-C12 heteroarylamine; or C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, C3-C12 heteroaryl and C3-C12 heteroarylamine which are substituted by one or at least two of deuterium, halogen, nitro and cyano;
preferably, R is selected from at least one of deuterium atom, halogen, cyano, nitro, C1-C4 alkyl, halogen substituted C1-C4 alkyl, deuterium substituted C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, halogen substituted C1-C4 alkenyl, deuterium substituted C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, halogen substituted C6-C12 aryl, deuterium substituted C6-C12 aryl, cyano substituted C6-C12 aryl, C3-C12 heteroaryl, C3-C12 heteroarylamine, halogen substituted C3-C12 membered heteroaryl or deuterium substituted C3-C12 heteroaryl.
Preferably, the organic compound is any one of the following compounds P-1 to P-60 and n-1 to n-80:
Figure BDA0002731949470000032
Figure BDA0002731949470000041
Figure BDA0002731949470000051
Figure BDA0002731949470000061
Figure BDA0002731949470000071
Figure BDA0002731949470000081
Figure BDA0002731949470000091
Figure BDA0002731949470000101
Figure BDA0002731949470000111
in the present invention, the organic compound can be prepared by the following preparation method:
Figure BDA0002731949470000121
in another aspect, the present invention provides an organic electroluminescent material comprising the organic compound as described above.
Preferably, the organic compound is used as an organic electroluminescent host material.
In another aspect, the present invention provides an organic electroluminescent composition comprising the organic compound as described above.
Preferably, the organic electroluminescent composition further comprises another compound W, and the compound W is any one of triazine compounds, pyrimidine compounds, quinoxaline compounds, quinazoline compounds or carbazole compounds.
Preferably, the carbazole compound is any one of A1-A3 in the following compounds:
Figure BDA0002731949470000122
wherein R is1、R2Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or-L6NAr6Ar7；
Ar6And Ar7Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
Y1、Y2each independently selected from O, S, CR3R4、NR5，
R3、R4Each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl; r5、Ar5Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl or-L6NAr6Ar7Wherein Ar is6And Ar7The same limitations as above;
L5、L6selected from single bond, substituted or unsubstituted aryl of C6-C30,
n and m are independently integers of 0-4;
adjacent substituents are not linked or connected to each other to form a ring.
The ring is preferably selected from a substituted or unsubstituted C6-C20 aromatic ring, a substituted or unsubstituted C3-C20 aromatic heterocycle; the ring is more preferably selected from the group consisting of substituted or unsubstituted: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, an indene ring, an indole ring, a benzofuran ring or a benzothiophene ring. When the number of rings is two or more, the rings may be the same or different.
Preferably, the carbazole compound is any one of the following compounds I-1 to I-32:
Figure BDA0002731949470000131
Figure BDA0002731949470000141
Figure BDA0002731949470000151
preferably, the structural formula of the triazine compound is as follows:
Figure BDA0002731949470000152
wherein L is1-L3Each independently selected from single bond, substituted or unsubstituted C6-C30 aryl, Ar1-Ar3Each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring. The rings are as defined above. Preferably, the structural formula of the pyrimidine compound is as follows:
Figure BDA0002731949470000153
wherein, X1-X3Each independently selected from N, CR6Two of which are selected from N;
R6selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
L1-L3each is independently selected fromA bond, a substituted or unsubstituted C6-C30 aryl group,
Ar1-Ar3each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring. The rings are as defined above.
Preferably, the quinoxaline compound has the following structure:
Figure BDA0002731949470000154
wherein, X4And X7Is selected from N, X5And X6Selected from the group consisting of CR6，L4Each independently selected from single bond, substituted or unsubstituted aryl of C6-C30, R6Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar4each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
k is an integer from 1 to 2, and ring A is a substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring. The rings are as defined above.
Preferably, the quinazoline compound has the following structure:
Figure BDA0002731949470000161
wherein, X5And X7Is selected from N, X4And X6Selected from the group consisting of CR6(ii) a Or X4And X6Is selected from N, X5And X7Selected from the group consisting of CR6；
L4Each independently selected from single bond, substituted or unsubstituted aryl of C6-C30, R6Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar4each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
k is an integer from 1 to 2, and ring A is a substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring. The rings are as defined above.
Preferably, ring a is a substituted or unsubstituted group as follows: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, an indene ring, an indole ring, a benzofuran ring or a benzothiophene ring.
The substituents are as defined above.
The triazine compounds, pyrimidine compounds, quinoxaline compounds and quinazoline compounds are preferably selected from any one of II-1 to II-32.
Figure BDA0002731949470000162
Figure BDA0002731949470000171
Figure BDA0002731949470000181
Preferably, the organic electroluminescent composition is a combination of an electron transport type compound and a hole transport type compound.
Preferably, the organic compound of the present invention in the organic electroluminescent composition serves as an electron transport compound and a hole transport compound.
In another aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer comprising the organic electroluminescent compound as described above.
In the present invention, the organic layer includes at least one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and contains at least a light emitting layer.
Preferably, the light-emitting layer comprises a host material and a guest material, the host material comprising an organic compound as described above, or an organic electroluminescent composition as described above.
Preferably, the guest material is a phosphorescent dopant.
Preferably, the phosphorescent dopant comprises at least one of Ir, Pt, Ni, Au, Os, Re, Rh, Zn, Ag, Fe, W, preferably Ir.
Preferably, the phosphorescent dopant emits light at a wavelength of 550nm to 750 nm.
Preferably, the mass percentage of the host material in the light-emitting layer is 0.1% to 10%, such as 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10%, preferably 3% to 8%, and the mass percentage of the guest material is 90% to 99.9%, such as 90%, 92%, 94%, 96%, 97%, 98%, 99% or 99.9%, preferably 92% to 97%.
The hole injecting/transporting material used in the present invention is not particularly limited, and any compound may be used as long as the compound is generally used as a hole injecting/transporting material. Examples of materials include (but are not limited to): phthalocyanine or porphyrin derivatives; an aromatic amine derivative; indolocarbazole derivatives; a fluorocarbon-containing polymer; a polymer having a conductive dopant; conductive polymers such as PEDOT/PSS; self-assembling monomers derived from compounds such as phosphonic acids and silane derivatives; metal oxide derivatives such as MoOx; a p-type semiconductive organic compound; a metal complex; and a crosslinkable compound.
In the present invention, examples of the hole injection layer material are as follows:
Figure BDA0002731949470000191
in the present invention, examples of the aromatic derivative of the hole injection layer or the hole transport layer are as follows:
Figure BDA0002731949470000201
wherein Ar is6To Ar14Each of which is independently selected from: a group consisting of aromatic hydrocarbon cyclic groups such as: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene, and azulene; a group consisting of aromatic heterocyclic groups such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzoselenenopyridine, and selenenopyridine; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Each timeEach Ar may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In the present invention, an Electron Blocking Layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a barrier layer in a device may result in substantially higher efficiency and/or longer lifetime compared to a similar device lacking a barrier layer. In addition, a blocking layer may be used to confine excitons in the light emitting layer.
In the present invention, the electron blocking layer material may be:
Figure BDA0002731949470000202
wherein L is3-L5Each independently selected from a linking bond, phenyl, biphenylyl or terphenyl,
R21-R22each independently selected from hydrogen, methyl, ethyl, tert-butyl or phenyl,
Ar15-Ar16each independently selected from 9, 9-dimethylfluorene, 9-diphenylfluorene, phenyl, naphthalene, biphenylyl, terphenyl or carbazolyl,
in the present invention, the electron blocking layer material can be exemplified as follows:
Figure BDA0002731949470000203
Figure BDA0002731949470000211
in the present invention, a Hole Blocking Layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a barrier layer in a device may result in substantially higher efficiency and/or longer lifetime compared to a similar device lacking a barrier layer. In addition, blocking layers may be used to confine excitons in the light-emitting layer. Suitable existing materials may be used, for example triazine based compounds.
In the present invention, the Electron Transport Layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complex or organic compound may be used as long as it is generally used to transport electrons.
In the invention, the material of the electron injection layer is selected from KF, LiF, NaCl and Li2O, Mg, or the like, or consists of a lithium halide or a lithium organic compound.
In the present invention, the light emitting layer includes a host material and a dopant material, the dopant material is a phosphorescent dopant, and the phosphorescent dopant is exemplified by the following:
Figure BDA0002731949470000212
wherein R is7-R19Each independently selected from H, deuterium, C1-C12 alkyl, C1-C12 cycloalkyl, C6-C20 aryl and C1-C12 alkyl substituted C6-C20 aryl.
Specific phosphorescent dopants are exemplified by:
Figure BDA0002731949470000213
in another aspect, the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device comprises at least two organic electroluminescent devices stacked to form a series structure.
In another aspect, the present invention provides the use of an organic electroluminescent device as described above in a display device or a lighting device.
Compared with the prior art, the invention has the following beneficial effects:
the organic compound has benzophenanthro [4,5-bcd ] thiophene group, and has the advantages of good planarity, good conjugation, strong hole and electron transmission capability, good thermal stability, long service life of the prepared device and high current efficiency.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device of the present invention, in which 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, 7 is an electron injection layer, and 8 is a cathode.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthesis examples:
compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially. The solvent and reagents used in the present invention, such as potassium carbonate, toluene, palladium catalyst, methylene chloride, anhydrous magnesium sulfate, etc., are commercially available from the domestic chemical product market, such as from national drug group reagent company, TCI company, shanghai Bigdi medicine company, Bailingwei reagent company, etc. In addition, they can be synthesized by a known method by those skilled in the art.
The analytical detection of intermediates and compounds in the present invention uses a mass spectrometer (model Orbitrap ID-X Tribrid) and an organic element analyzer (model PE2400 II).
Synthesis example 1
Figure BDA0002731949470000221
Synthesis of intermediate n-19-1: in a 50 ml three-necked flask, raw material 1(2.62 g, 0.01mol), raw material 2(1.56 g, 0.01mol), potassium carbonate (1.66 g, 0.012mol), toluene (25 ml), water (5 ml), tetrakis (triphenylphosphine) palladium (5.8 g, 0.5mmol) were added under nitrogen protection, stirred at 100 ℃ for 10 hours, reacted and cooled to room temperature. Adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10) to give intermediate n-19-1(1.41 g, 48% yield).
And (3) synthesizing an intermediate n-19-2: taking a 100 ml double-neck round-bottom flask, putting a stirrer and an upper reflux pipe, introducing nitrogen after drying, and respectively adding an intermediate n-19-1(2.94 g, 0.01mol), palladium acetate (0.5mmol), tri-tert-butylphosphine (0.01mol), pivalic acid (t-BuCO)2H, 0.015mol), potassium carbonate (K)2CO30.01mol) and toluene (40 ml), stirred at 120 ℃ for 10 hours, cooled to room temperature after completion of the reaction, concentrated and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (vol.%)) to give intermediate n-19-2(1.73 g, 67% yield).
And (3) synthesizing an intermediate n-19-3: a100 ml double-neck round-bottom bottle is taken, a stirrer and an upper reflux pipe are placed in the bottle, nitrogen is filled after drying, an intermediate n-19-2(2.58 g and 0.01mol) is respectively added, n-butyllithium (0.01mol) and 50 ml tetrahydrofuran are dropwise added at 78 ℃, stirring is carried out for 1 hour, 1, 2-dibromoethane (0.01mol) is added, and stirring is carried out for 5 hours at room temperature. After the reaction is completed, water is added for quenching. Extracting the reaction system for three times by using dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (EtOAc/hexane, 1/10) to afford intermediate n-19-3(2.05 g, 61% yield).
And (3) synthesizing an intermediate n-19-4: in a 100 ml three-neck bottle, adding the intermediate n-19-3(0.01mol) and tetrahydrofuran (40 ml) under the protection of nitrogen, dropwise adding n-butyllithium (0.011mol) at 78 ℃, stirring for 1 hour, adding trimethyl borate (0.015mol), subsequently heating to room temperature, stirring for 12 hours, washing a crude product with dilute hydrochloric acid, extracting with ethyl acetate, and removing a solvent to obtain the intermediate n-19-4(2.63 g, the yield is 87%).
Synthesis of n-19: in a 50 ml three-necked flask, under the protection of nitrogen, the intermediate n-19-4(3.02 g, 0.01mol), the raw material 3(4.63 g, 0.01mol), potassium carbonate (1.66 g, 0.012mol), toluene (25 ml), water (5 ml), tetrakis (triphenylphosphine) palladium (5.8 g, 0.5mmol) were added, stirred at 100 ℃ for 10 hours, and then cooled to room temperature after reaction. Adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10) to give n-19(5.26 g, 82% yield).
Elemental analysis: theoretical value of C45H27N 3S: c, 84.22, H, 4.24, N, 6.55, S, 5.00, found: c, 84.17, H, 4.24, N, 6.58, S, 5.01, HRMS (ESI) M/z (M +): theoretical value: 641.1926, found: 641.1932.
Figure BDA0002731949470000231
Synthesis of p-11: the same procedure as for the synthesis of intermediate n-19-1 was followed except that starting material 5(0.01mol) was used instead of starting material 1 and intermediate n-19-4 was used instead of starting material 2(0.01mol) to give p-11(5.29 g, 81% yield).
Elemental analysis: theoretical value of C48H29 NS: c, 88.45, H, 4.48, N, 2.15, S, 4.92, found: c, 88.49, H, 4.46, N, 2.15, S, 4.90, HRMS (ESI) M/z (M +): theoretical value: 651.2021, found: 651.2016.
Synthesis example 2
Figure BDA0002731949470000232
Synthesis of intermediate p-38-1: taking a 100 ml double-neck round-bottom flask, putting a stirrer and an upper reflux pipe, introducing nitrogen after drying, respectively adding intermediates n-19-3(3.36 g, 0.1mol), o-chloroaniline (0.01mol), palladium acetate (0.05mmol), tri-tert-butylphosphine (0.055mmol), sodium tert-butoxide (0.015mol) and toluene (30 ml), heating to 80 ℃ for reaction for 2 hours, adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10) to give intermediate p-38-1(3.18 g, 83% yield).
Synthesis of intermediate p-38-2: taking a 100 ml double-neck round-bottom flask, putting a stirrer and an upper reflux pipe, introducing nitrogen after drying, and respectively adding an intermediate p-38-1(3.83 g, 0.01mol), palladium acetate (0.5mmol), tri-tert-butylphosphine (0.01mol), pivalic acid (t-BuCO)2H, 0.015mol), potassium carbonate (K)2CO30.01mol) and toluene (40 ml), stirred at 120 ℃ for 10 hours, cooled to room temperature after completion of the reaction, concentrated and the crude product purified by chromatography (ethyl acetate/n-hexane, 1/10 (vol.%)) to give intermediate p-38-2(2.08 g, 60% yield).
Synthesis of intermediate p-38-3: in a 50 ml three-necked flask, the intermediates p-38-2(3.47 g, 0.01mol), bromobenzene (0.01mol), potassium carbonate (0.012mol), toluene (25 ml), water (5 ml), tetrakis (triphenylphosphine) palladium (0.5mmol) were added under nitrogen protection, stirred at 100 ℃ for 10 hours, and cooled to room temperature after reaction. Adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10) to give intermediate p-38-3(3.76 g, 89% yield).
Synthesis of intermediate p-38-4: a100 ml double-neck round-bottom bottle is taken, a stirrer and an upper reflux pipe are placed in the bottle, nitrogen is filled after drying, an intermediate p-38-3(4.23 g, 0.01mol), N-bromosuccinimide (0.015mol) and 50 ml tetrahydrofuran are respectively added, and stirring is carried out for 15 hours at room temperature. After the reaction is completed, water is added for quenching. Extracting the reaction system for three times by using dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (EtOAc/hexane, 1/10) to afford intermediate p-38-4(3.46 g, 69% yield).
Synthesis of p-38: the same synthesis as intermediate n-19-1 was performed except that intermediate p-38-4(0.01mol) was used instead of starting material 1 and starting material 4(0.01mol) was used instead of starting material 2, to give p-38(5.11 g, 77% yield).
Elemental analysis: theoretical value of C48H28N 2S: c, 86.72, H, 4.25, N, 4.21, S, 4.82, found: c, 86.67, H, 4.27, N, 4.22, S, 4.84, HRMS (ESI) M/z (M +): theoretical value: 664.1973, found: 664.1978.
Figure BDA0002731949470000241
Synthesis of n-46: in a 50 ml three-necked flask, the intermediate p-38-2(3.47 g, 0.01mol), the raw material 6(0.01mol), potassium carbonate (0.012mol), toluene (25 ml), water (5 ml), and tetrakis (triphenylphosphine) palladium (0.5mmol) were added under nitrogen protection, stirred at 100 ℃ for 10 hours, and cooled to room temperature after reaction. Adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10) to give n-46(5.69 g, 87% yield).
Elemental analysis: theoretical value of C45H26N 4S: c, 82.54, H, 4.00, N, 8.56, S, 4.90, found: c, 82.59, H, 4.00, N, 8.53, S, 4.88, HRMS (ESI) M/z (M +): theoretical value: 654.1878, found: 654.1886.
Figure BDA0002731949470000251
Synthesis of n-81: the same as the synthesis of n-46, except that starting material 6 was replaced with starting material 13(0.01mol), gave n-81 (78% yield).
Elemental analysis: theoretical value of C40H21N3S 2: c, 79.05, H, 3.48, N, 6.91, S, 10.55, found: c, 78.99, H, 3.50, N, 6.92, S, 10.59, HRMS (ESI) M/z (M +): theoretical value: 607.1177, found: 607.1182.
Figure BDA0002731949470000252
Synthesis of n-83: the same as in the synthesis of n-46 except that starting material 6 was replaced with starting material 14(0.01mol) gave n-81 (81% yield).
Elemental analysis: theoretical value of C39H20N2 SO: c, 82.96, H, 3.57, N, 4.96, S, 5.68, found: c, 82.93, H, 3.56, N, 4.98, S, 5.70, HRMS (ESI) M/z (M +): theoretical value: 564.1296, found: 564.1301.
Figure BDA0002731949470000253
Synthesis of p-43: the same synthesis as intermediate n-19-1 was performed except that intermediate p-38-4(0.01mol) was used instead of starting material 1 and starting material 7(0.01mol) was used instead of starting material 2, to give p-43(5.79 g, 74% yield).
Elemental analysis: theoretical value of C57H38N 2S: c, 87.44, H, 4.89, N, 3.58, S, 4.09, found: c, 87.41, H, 4.91, N, 3.58, S, 4.10, HRMS (ESI) M/z (M +): theoretical value: 782.2756, found: 782.2759.
Figure BDA0002731949470000261
Synthesis of p-44: the synthesis of p-43 was identical except that starting material 15 was used instead of starting material 7 to give p-44(5.82 g, 77% yield)
Elemental analysis: theoretical value of C54H32N2 SO: c, 85.69, H, 4.26, N, 3.70, S, 4.24, found: c, 85.72, H, 4.25, N, 3.69, S, 4.22, HRMS (ESI) M/z (M +): theoretical value: 756.2235, found: 756.2243.
Figure BDA0002731949470000262
Synthesis of n-53: in a 50 ml three-necked flask, the intermediate p-38-2(3.47 g, 0.01mol), the raw material 8(0.01mol), potassium carbonate (0.012mol), toluene (25 ml), water (5 ml), and tetrakis (triphenylphosphine) palladium (0.5mmol) were added under nitrogen protection, stirred at 100 ℃ for 10 hours, and cooled to room temperature after reaction. Adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10) to give n-46(6.31 g, 82% yield).
Elemental analysis: theoretical value of C54H34N 4S: c, 84.13, H, 4.45, N, 7.27, S, 4.16, found: c, 84.18, H, 4.43, N, 7.24, S, 4.15, HRMS (ESI) M/z (M +): theoretical value: 770.2504, found: 770.2509.
Synthesis example 3
Figure BDA0002731949470000271
Synthesis of intermediate p-51-1: the difference from the synthesis of intermediate n-19-1 was that starting material 9(0.01mol) was used instead of starting material 1 and intermediate n-19-4(0.01mol) was used instead of starting material 2, giving intermediate p-51-1(2.96 g, 78% yield).
Synthesis of intermediate p-51-2: a100 ml double-neck round-bottom bottle is taken and put into a stirrer and an upper reflux pipe, nitrogen is filled after drying, an intermediate p-51-1(3.79 g, 0.01mol), triphenylphosphine (0.02mol) and 1, 2-dichlorobenzene (40 ml) are respectively added, heating reaction is carried out at 180 ℃ for 12 hours, cooling is carried out to room temperature after the reaction is finished, the reaction system is concentrated, and a crude product is purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain an intermediate p-51-2(2.91 g, 84% yield).
Synthesis of intermediate p-51-3: the difference from the synthesis of intermediate p-38-3 was that intermediate p-51-3(3.76 g, 89% yield) was obtained by substituting intermediate p-51-2(0.01mol) for intermediate p-38-2
Synthesis of intermediate p-51-4: a100 ml double-neck round-bottom bottle is taken, a stirrer and an upper reflux pipe are placed in the bottle, nitrogen is filled after drying, an intermediate p-51-3(4.23 g, 0.01mol), N-bromosuccinimide (0.011mol) and 40 ml tetrahydrofuran are respectively added, and stirring is carried out for 6 hours at room temperature. After the reaction was complete, 5 ml of water were added. Extracting the reaction system for three times by using dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (EtOAc/hexane, 1/10) to afford intermediate p-51-4(2.56 g, 51% yield).
Synthesis of p-51: the same synthesis as intermediate n-19-1 was performed except that intermediate p-51-4(0.01mol) was used instead of starting material 1 and starting material 10(0.01mol) was used instead of starting material 2, to give p-51(5.57 g, 78% yield).
Elemental analysis: theoretical value of C52H30N 2S: c, 87.37, H, 4.23, N, 3.92, S, 4.48, found: c, 87.34, H, 4.24, N, 3.93, S, 4.49, HRMS (ESI) M/z (M +): theoretical value: 714.2130, found: 714.2138.
Synthesis example 4
Figure BDA0002731949470000272
Synthesis of intermediate n-72-1: the synthesis of n-53 was identical except that starting material 11(0.01mol) was used instead of starting material 8, giving intermediate n-72-1(4.49 g, 90% yield).
Synthesis of intermediate n-72-2: a100 ml double-neck round-bottom bottle is taken, a stirrer and an upper reflux pipe are placed in the bottle, nitrogen is filled after drying, an intermediate n-72-1(2.58 g and 0.01mol) is respectively added, n-butyllithium (0.01mol) and 50 ml tetrahydrofuran are dropwise added at 78 ℃, stirring is carried out for 1 hour, 1, 2-dibromoethane (0.01mol) is added, and stirring is carried out for 5 hours at room temperature. After the reaction is completed, water is added for quenching. Extracting the reaction system for three times by using dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (EtOAc/hexane, 1/10) to afford intermediate n-72-2(2.37 g, 41% yield).
Synthesis of n-72: the same synthesis method as that of intermediate n-19-1 was used except that intermediate n-72-2(0.01mol) was used instead of raw material 1 and raw material 12(0.01mol) was used instead of raw material 2, to obtain n-72(5.62 g, 77% yield).
Elemental analysis: theoretical value of C51H30N 4S: c, 83.81, H, 4.14, N, 7.67, S, 4.39, found: c, 83.84, H, 4.15, N, 7.64, S, 4.37, HRMS (ESI) M/z (M +): theoretical value: 730.2191, found: 730.2198.
Device embodiments
Device example 1
The present embodiment provides an organic electroluminescent device, which has a schematic structural diagram as shown in fig. 1, and includes an anode layer 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8, which are sequentially disposed on a substrate 1 from bottom to top.
The anode 2 is made of an ITO material, and the hole injection layer 3 is made of NDP-9 and DNTPD, wherein the mass ratio of NDP-9 to DNTPD is 3 to 97; the hole transport layer 4 is NPB; the light-emitting layer 5 is composed of a host material and a doping material, the host material is a compound (shown in table 1) of the invention, the guest material is RD-1, and the mass ratio of the host material to the guest material is 96: 4; the electron transport layer 6 is made of ET-2 and LiQ, wherein the weight ratio of ET-2 to LiQ is 1:1 (mass ratio); the electron injection layer 7 is LiQ; the cathode 8 is made of Mg/Ag, wherein the ratio of Mg to Ag is 9:1 (mass ratio).
Figure BDA0002731949470000281
The preparation process of the organic electroluminescent device is as follows:
(1) substrate cleaning: carrying out ultrasonic treatment on the motor substrate coated with the transparent ITO in an aqueous cleaning agent (the components and concentration of the aqueous cleaning agent are that ethylene glycol solvent is less than or equal to 10 wt% and triethanolamine is less than or equal to 1 wt%), washing in deionized water, carrying out ultrasonic oil removal in a mixed solvent of acetone and ethanol (volume ratio is 1:1), baking in a clean environment until moisture is completely removed, and then cleaning by using ultraviolet light and ozone;
(2) evaporation: placing the glass substrate with anode layer in vacuum chamber, and vacuumizing to 1 × 10-6To 2X 10-4Pa, carrying out vacuum evaporation on the anode layer film by using a co-evaporation mode to obtain a hole injection material, adjusting the rate of NDP-9 and DNTPD according to the mass ratio, wherein the total evaporation rate is 0.1nm/s, and the evaporation thickness is 10 nm;
(3) evaporating a hole transport layer on the hole injection layer at the evaporation rate of 0.1nm/s and the evaporation film thickness of 80 nm;
(4) evaporating a luminescent layer on the hole transport layer, and evaporating a luminescent host material and an object material in vacuum in a co-evaporation mode, wherein the evaporation rate of the host material and the object material is adjusted according to the mass ratio, the total evaporation rate is 0.01nm/s, and the total evaporation film thickness is 40 nm;
(5) vacuum evaporating an electron transport layer on the luminescent layer, and adjusting the evaporation rate according to the mass ratio, wherein the total evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
(6) vacuum evaporating an electron injection layer on the electron transport layer, wherein the evaporation rate is 0.05nm/s, and the total film thickness is 1 nm;
(7) Mg/Ag is used as a cathode layer of the device, the evaporation rate is adjusted according to the mass ratio, the total evaporation rate is 0.1nm/s, and the total evaporation film thickness is 80 nm.
The following tests were carried out for the organic electroluminescent devices (the host materials of the light-emitting layer in the devices are shown in table 1) in some of the device examples and 1 device comparative examples provided by the present invention:
the characteristics of the device such as current, voltage, brightness, luminescence spectrum and the like are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system, and the test conditions are as follows: the current density is 20mA/cm2Room temperature;
and (3) life test: the time (in hours) was recorded when the device brightness dropped to 98% of the original brightness.
The results are shown in Table 1.
TABLE 1
Figure BDA0002731949470000291
As can be seen from the test data in Table 1, the life and efficiency of the prepared device are higher than those of the device prepared by using the compound containing benzophenanthro [4,5-bcd ] thiophene as the main material of the luminescent layer; the combination of n and p type compounds as the main body material has obviously improved service life and current efficiency.
The applicant states that the present invention is illustrated by the above examples of the organic compounds of the present invention and their applications, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must rely on the above examples to be practiced. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.

Claims (10)

1. An organic compound having a structure represented by formula I:
Figure FDA0002731949460000011
wherein R is1Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, or-L6NAr6Ar7；
Ar6And Ar7Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and adjacent R1Between which is not connected or adjacent to R1Are connected to form a heterocyclic ring containing N;
L6selected from single bond, substituted or unsubstituted aryl of C6-C30; n is an integer of 0 to 4.
2. An organic compound according to claim 1, wherein when the groups contain a substituent, the substituent is independently selected from deuterium, halogen, nitro, cyano, alkyl of C1-C4, alkoxy of C1-C4, alkenyl of C1-C4, aryl of C6-C12, aryloxy of C6-C12, arylamine of C6-C12, heteroaryl of C3-C12, heteroarylamine of C3-C12, or alkyl of C1-C4, alkoxy of C1-C4, alkenyl of C1-C4, aryl of C6-C12, aryloxy of C6-C12, arylamine of C6-C12, heteroaryl of C3-C12, heteroaryl of C3-C12, substituted by one or at least two of deuterium, halogen, nitro and cyano;
preferably, when said group contains a substituent, the substituent groups are respectively and independently selected from at least one or two of deuterium atoms, halogens, cyano groups, nitro groups, C1-C4 alkyl groups, halogen-substituted C1-C4 alkyl groups, deuterium-substituted C1-C4 alkyl groups, C1-C4 alkoxy groups, C1-C4 alkenyl groups, halogen-substituted C1-C4 alkenyl groups, deuterium-substituted C1-C4 alkenyl groups, C6-C12 aryl groups, C6-C12 aryloxy groups, C6-C12 arylamine groups, halogen-substituted C6-C12 aryl groups, deuterium-substituted C6-C12 aryl groups, cyano-substituted C6-C12 aryl groups, C3-C12 heteroaryl groups, C3-C12 heteroaryl groups, halogen-substituted C3-C12 heteroaryl groups or deuterium-substituted C12 heteroaryl groups.
3. An organic compound according to claim 1 or 2, characterized in that the alkyl group is preferably a C1-C4 alkyl group;
preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl or spirobifluorenyl;
preferably, the heteroaryl group is selected from dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthoimidazolyl, naphthooxazolyl, naphthothiazolyl, phenanthroimidazolyl, phenanthroizooxazolyl, phenanthroizothiazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidinyl, benzofuropyrazinyl, benzofuropyrimidinyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl, indenopyrimidinyl, spiro (fluorene-9, 1 '-indene) pyrazinyl, spiro (fluorene-9, 1' -indene) pyrimidyl, benzofurocarbazolyl, or benzothiophenocarbazolyl.
4. The organic compound of any one of claims 1-3, wherein the organic compound has a structure represented by formula II-1 or formula II-2 below:
Figure FDA0002731949460000021
Figure FDA0002731949460000031
wherein R is1And n is as defined for formula I, Ar5Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl or-L6NAr6Ar7Wherein Ar is6And Ar7And L6Is the same as in formula I, m is an integer of 0 to 4;
L5selected from single bond, substituted or unsubstituted aryl of C6-C30;
r is selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, C3-C12 heteroaryl and C3-C12 heteroarylamine; or C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, C3-C12 heteroaryl and C3-C12 heteroarylamine which are substituted by one or at least two of deuterium, halogen, nitro and cyano;
preferably, R is selected from at least one of deuterium atom, halogen, cyano, nitro, C1-C4 alkyl, halogen substituted C1-C4 alkyl, deuterium substituted C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, halogen substituted C1-C4 alkenyl, deuterium substituted C1-C4 alkenyl, C6-C12 aryl, C6-C12 aryloxy, C6-C12 arylamine, halogen substituted C6-C12 aryl, deuterium substituted C6-C12 aryl, cyano substituted C6-C12 aryl, C3-C12 heteroaryl, C3-C12 heteroarylamine, halogen substituted C3-C12 membered heteroaryl or deuterium substituted C3-C12 heteroaryl.
5. The organic compound according to any one of claims 1 to 4, wherein the organic compound is any one of the following compounds P-1 to P-60 and n-1 to n-80:
Figure FDA0002731949460000032
Figure FDA0002731949460000041
Figure FDA0002731949460000051
Figure FDA0002731949460000061
Figure FDA0002731949460000071
Figure FDA0002731949460000081
Figure FDA0002731949460000091
Figure FDA0002731949460000101
Figure FDA0002731949460000111
Figure FDA0002731949460000121
6. an organic electroluminescent material, characterized in that the organic electroluminescent material comprises the organic compound according to any one of claims 1 to 5;
preferably, the organic compound is used as an organic electroluminescent host material.
7. An organic electroluminescent composition, characterized in that it comprises an organic compound according to any one of claims 1 to 5;
preferably, the organic electroluminescent composition further comprises another compound W, wherein the compound W is any one of triazine compounds, pyrimidine compounds, quinoxaline compounds, quinazoline compounds or carbazole compounds;
preferably, the carbazole compound is any one of A1-A3 in the following compounds:
Figure FDA0002731949460000131
wherein R is1、R2Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or-L6NAr6Ar7；
Ar6And Ar7Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
Y1、Y2each independently selected from O, S, CR3R4、NR5，
R3、R4Each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl; r5、Ar5Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl or-L6NAr6Ar7Wherein Ar is6And Ar7The same limitations as above;
L5、L6selected from single bond, substituted or unsubstituted aryl of C6-C30,
n and m are independently integers of 0-4;
adjacent substituents are not connected or connected to form a ring;
preferably, the carbazole compound is any one of the following compounds I-1 to I-32:
Figure FDA0002731949460000141
Figure FDA0002731949460000151
Figure FDA0002731949460000161
Figure FDA0002731949460000171
Figure FDA0002731949460000181
preferably, the structural formula of the triazine compound is as follows:
Figure FDA0002731949460000182
wherein L is1-L3Each independently selected from single bond, substituted or unsubstituted C6-C30 aryl, Ar1-Ar3Each independently selected from hydrogen, andsubstituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; adjacent substituents are not connected or connected to form a ring;
preferably, the structural formula of the pyrimidine compound is as follows:
Figure FDA0002731949460000183
wherein, X1-X3Each independently selected from N, CR6Two of which are selected from N;
R6selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
L1-L3each independently selected from single bond, substituted or unsubstituted aryl of C6-C30,
Ar1-Ar3each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring;
preferably, the quinoxaline compound has the following structure:
Figure FDA0002731949460000191
wherein, X4And X7Is selected from N, X5And X6Selected from the group consisting of CR6，L4Each independently selected from single bond, substituted or unsubstituted aryl of C6-C30, R6Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar4each independently selected from hydrogenSubstituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
k is an integer from 1 to 2, and ring A is a substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring;
preferably, the quinazoline compound has the following structure:
Figure FDA0002731949460000192
wherein, X5And X7Is selected from N, X4And X6Selected from the group consisting of CR6(ii) a Or X4And X6Is selected from N, X5And X7Selected from the group consisting of CR6；
L4Each independently selected from single bond, substituted or unsubstituted aryl of C6-C30, R6Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar4each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
k is an integer from 1 to 2, and ring A is a substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl;
adjacent substituents are not connected or connected to form a ring;
preferably, ring a is a substituted or unsubstituted group as follows: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, an indene ring, an indole ring, a benzofuran ring or a benzothiophene ring.
8. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer comprising the organic electroluminescent compound according to any one of claims 1 to 5;
preferably, the organic layer comprises at least one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and at least comprises a light emitting layer;
preferably, the light-emitting layer comprises a host material and a guest material, the host material comprising an organic compound according to any one of claims 1 to 5, or an organic electroluminescent composition according to claim 6;
preferably, the guest material is a phosphorescent dopant;
preferably, the phosphorescent dopant comprises at least one of Ir, Pt, Ni, Au, Os, Re, Rh, Zn, Ag, Fe, W, preferably Ir;
preferably, the phosphorescent dopant emits light at a wavelength of 550nm to 750 nm;
preferably, the mass percentage of the guest material in the light-emitting layer is 0.1% to 10%, preferably 3% to 8%, and the mass percentage of the host material is 90% to 99.9%, preferably 92% to 97%.
9. An organic electroluminescent device, wherein at least two organic electroluminescent devices as claimed in claim 8 are stacked to form a series structure.
10. Use of the organic electroluminescent device according to claim 8 in a display device or a lighting device.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112961144A (en) * 2021-02-05 2021-06-15 南京高光半导体材料有限公司 Compound, mixture and organic electroluminescent device
CN113135928A (en) * 2020-01-17 2021-07-20 江苏三月光电科技有限公司 Organic compound and organic electroluminescent device comprising same
CN113277997A (en) * 2021-05-28 2021-08-20 南京高光半导体材料有限公司 Compound containing anthracene-based structure and organic electroluminescent device
CN113429334A (en) * 2021-05-31 2021-09-24 南京高光半导体材料有限公司 Compound containing benzophenanthrene furan structure and organic electroluminescent device thereof
WO2022229298A1 (en) * 2021-04-29 2022-11-03 Merck Patent Gmbh Materials for organic electroluminescent devices
EP4223853A1 (en) * 2022-02-04 2023-08-09 Samsung Display Co., Ltd. Organic electroluminescent devices

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004018665A (en) * 2002-06-17 2004-01-22 Toyo Ink Mfg Co Ltd Organic electroluminescent device material and organic electroluminescent device using the same
CN102858913A (en) * 2010-04-28 2013-01-02 通用显示公司 Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
CN103180407A (en) * 2010-10-15 2013-06-26 默克专利有限公司 Triphenylene-based materials for organic electroluminescent devices
WO2018159961A1 (en) * 2017-02-28 2018-09-07 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device
CN110862381A (en) * 2019-12-04 2020-03-06 宁波卢米蓝新材料有限公司 Organic electroluminescent compound and preparation method and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004018665A (en) * 2002-06-17 2004-01-22 Toyo Ink Mfg Co Ltd Organic electroluminescent device material and organic electroluminescent device using the same
CN102858913A (en) * 2010-04-28 2013-01-02 通用显示公司 Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
CN103180407A (en) * 2010-10-15 2013-06-26 默克专利有限公司 Triphenylene-based materials for organic electroluminescent devices
WO2018159961A1 (en) * 2017-02-28 2018-09-07 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device
CN110862381A (en) * 2019-12-04 2020-03-06 宁波卢米蓝新材料有限公司 Organic electroluminescent compound and preparation method and application thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
KLEMM, L. H.，等: "Chemistry of condensed thiophenes. III. Acetylation of triphenyleno[1,12-bcd]thiophene", 《JOURNAL OF HETEROCYCLIC CHEMISTRY 》 *
MASAICHI SAITO，等: "Synthesis and structures of heterasumanenes having different heteroatom functionalities", 《TETRAHEDRON LETTERS》 *
TAKESHI KIMURA,等: "Effect of Through-Space Interaction on the Photolytic Desulfurization or Deselenization and Intramolecular Cyclization Reactions of 1,9-Disubstituted Dibenzochalcogenophenes", 《J. ORG. CHEM.》 *
TAKESHI KIMURA，等: "Evidence of Through-Space Interaction between the Sulfur and Aromatic Ring on Photo|ysis of 1-(Phenylthio)-9-aryldibenzothiophenes", 《TETRAHEDRON LETTERS》 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113135928A (en) * 2020-01-17 2021-07-20 江苏三月光电科技有限公司 Organic compound and organic electroluminescent device comprising same
CN113135928B (en) * 2020-01-17 2024-02-13 江苏三月科技股份有限公司 Organic compound and organic electroluminescent device comprising same
CN112961144A (en) * 2021-02-05 2021-06-15 南京高光半导体材料有限公司 Compound, mixture and organic electroluminescent device
WO2022229298A1 (en) * 2021-04-29 2022-11-03 Merck Patent Gmbh Materials for organic electroluminescent devices
CN113277997A (en) * 2021-05-28 2021-08-20 南京高光半导体材料有限公司 Compound containing anthracene-based structure and organic electroluminescent device
CN113277997B (en) * 2021-05-28 2023-09-29 南京高光半导体材料有限公司 Anthracene-based structure-containing compound and organic electroluminescent device
CN113429334A (en) * 2021-05-31 2021-09-24 南京高光半导体材料有限公司 Compound containing benzophenanthrene furan structure and organic electroluminescent device thereof
EP4223853A1 (en) * 2022-02-04 2023-08-09 Samsung Display Co., Ltd. Organic electroluminescent devices

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