CN110903276A - Organic compound and organic electroluminescent device - Google Patents

Organic compound and organic electroluminescent device Download PDF

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CN110903276A
CN110903276A CN201811082013.2A CN201811082013A CN110903276A CN 110903276 A CN110903276 A CN 110903276A CN 201811082013 A CN201811082013 A CN 201811082013A CN 110903276 A CN110903276 A CN 110903276A
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王志鹏
曾礼昌
邵爽
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Beijing Eternal Material Technology Co Ltd
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Abstract

The present invention relates to the field of organic electroluminescence, which can provide an organic compound represented by general formula (1). The invention also includes an organic electroluminescent element made by using the compound as a hole transport material.

Description

Organic compound and organic electroluminescent device
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to a novel compound material taking fluorenyl and 2, 4-diphenylaniline as a central framework and application thereof in an OLED device structure.
Background
The OLED (Organic light-Emitting diode) display technology has the advantages of self-luminescence, high contrast, fast response speed and high color saturation, and particularly, the OLED display technology does not contain a backlight source, has a simple device structure and a wide working temperature range, can prepare flexible display on a flexible substrate, becomes a next generation display technology following an LCD, and gradually shows a wide commercial application prospect.
The simplest OLED device structure is generally formed by depositing an organic light emitting material several tens to several hundreds nanometers thick between two electrodes, and applying a certain voltage across the two electrodes to cause the material to emit light. In order to achieve higher luminous efficiency and lifetime, various auxiliary layers are also required to be introduced to balance the transport of carriers, and generally include a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. An organic electroluminescent device with good efficiency and long service life is generally the result of optimized matching of a device structure and various organic materials, and in order to realize higher luminous efficiency and longer service life of the device with lower working voltage, researchers are constantly dedicated to research and develop new organic electroluminescent materials so as to obtain materials with higher performance and enable an OLED (organic light emitting diode) to achieve a better working state.
In an OLED device, a hole transport material can improve the transport efficiency of holes in the device, which requires that it have high hole mobility, and at the same time, its Highest Occupied Molecular Orbital (HOMO) level is sufficient to enable efficient injection and transport between interfaces in contact with it.
In patent CN104603111, a compound of fluorene substituted in 1,3,4 position is reported.
In patent TW201726638A, a novel compound structure using dibenzofuran or dibenzothiophene, which is substituted at the 2,4 position, is reported.
Although the above-mentioned compounds are known, there is still room for improvement in improving and balancing mobility of holes in devices, and in order to meet the requirements for use of devices in practice, development of new hole transport materials is still required.
Disclosure of Invention
In view of the above problems of the prior art, the present inventors have conducted intensive studies. A series of compounds which have better performance compared with the known compounds and can be used for hole transport materials are designed and synthesized, and the efficiency and the service life of the device can be improved by using the compounds in an organic electroluminescent device.
Specifically, the present invention provides a compound represented by the following general formula (I),
Figure BDA0001802199990000011
wherein L independently represents a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene,
Ra、Rbthe same or different, each is independently selected from alkyl of C1-C20, alkenyl of C1-C20, alkynyl of C1-C20, Ra、RbR is selected from alkyl of C1-C20, alkenyl of C1-C20, alkynyl of C1-C20, alkoxy of C1-C20, aryl of C6-C30 and heteroaryl of C3-C30,
p is an integer of 0 to 7,
ar is selected from heteroaryl represented by the general formula A or substituted or unsubstituted aryl of C6-C30,
Figure BDA0001802199990000021
in the formula A, the reaction solution is prepared,
L1independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group, "-" represents a site of attachment to the parent nucleus,
R1selected from C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, multiple R1Identical or different, two R in adjacent position1May be linked to form a ring; q is an integer of 0 to 7, preferably 0 or 1,
x is selected from O, S, NR2、SiR3R4Preferably NR2、O、S；R2、R3、R4Each independently selected from C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, R3And R4Can be interconnected to form a ring,
the above-mentioned "substituted or unsubstituted" means substituted by one or more groups selected from C1～C12Alkyl of (C)1～C12Alkoxy group of (C)6～C12Aryl of (C)3～C12The heteroaryl group, cyano group or hydroxyl group in (1) is substituted, and a connecting bond between the substituents "-" represents a ring structure, and represents a connecting site at an arbitrary position on the ring structure where a bond can be formed.
As another aspect of the present invention, there is also provided a use of the organic electroluminescent material as described above in an organic electroluminescent device. The compound of the present invention has high electric-rich property, is suitable for use as a hole transport material, and the application field is not limited to organic electroluminescent materials, and can be applied to other fields.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer including at least a light-emitting layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains therein an organic electroluminescent material as described above.
The novel compound related by the invention takes a mother nucleus combined by fluorene and 2, 4-diphenylaniline as a main structure, and can ensure that the compound has good hole transport performance or electron blocking performance through the defined substituent group with a special structure. The specially limited substituent group is the heterocyclic group with the large conjugated structure or the condensed aromatic ring with the large conjugation, and the introduction of the condensed aromatic group with the large conjugation can increase the plane conjugation degree of the compound molecule, is favorable for improving the HOMO energy level of the molecule, can reduce the injection barrier of holes, increases the mobility of carriers and is favorable for reducing the starting voltage of the device; on the other hand, the introduction of the large conjugated fused aromatic ring can increase the thermal stability of molecules, improve the glass transition temperature of the molecules, facilitate the stability of devices and prolong the service life of the devices.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below.
In the present specification, unless otherwise indicated, the following terms have the following meanings:
in the present invention, the expression of Ca to Cb means that the group has carbon atoms a to b, and the carbon atoms do not include the carbon atoms of the substituents unless otherwise specified. In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium". In the present invention, "D" may be used to represent "deuterium".
In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of halogen, cyano, hydroxyl, alkyl groups of C1 to C12, alkoxy groups of C1 to C12, aryl groups of C6 to C12, heteroaryl groups of C3 to C12, cyano and hydroxyl, preferably fluorine, cyano, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, quinolyl, phenylpyridinyl, pyridylphenyl and the like.
In the present specification, the alkyl group may be linear or branched, and includes cycloalkyl groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 12. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, decyl, and the like.
In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms. Specific examples of aryl groups include phenyl, biphenyl, naphthyl, anthryl, phenanthryl, and the like. In the present specification, the heteroaryl group is a heteroaryl group containing at least one of O, N, S, Si as a heteroatom, and the number of carbon atoms is preferably 3 to 30. Specific examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, and the like. Wherein both aryl and heteroaryl groups include fused ring groups.
In the present specification, the expression of the "-" underlined loop structure means that the linking site is located at an arbitrary position on the loop structure where the linking site can be bonded.
The following describes various aspects of the present invention.
The present invention provides a compound represented by the following general formula (I),
Figure BDA0001802199990000031
wherein L independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group, and examples of the C6-C30 arylene group include a phenyl group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrenylene group, a fluorenylene group, a pyrenylene group
Figure BDA0001802199990000032
Mesitylene, fluorenylene, benzolene [ a]Anthracenyl, benzo [ c ] idene]Phenanthrene, triphenylene, or benzo [ k ]]Fluoranthenyl, benzidene [ g ]]
Figure BDA0001802199990000033
Radical, phenylene [ b]Triphenylene, phenyleneyl, peryleneyl, etc., among which phenylene, naphthylene, biphenylene are preferred, and phenylene is more preferred.
Ra、RbIs selected fromExamples of the alkyl group having from C1 to C20, the alkenyl group having from C1 to C20, and the alkynyl group having from C1 to C20 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, or octynyl, Ra and Rb are more preferably an alkyl group having from C1 to C12, and examples of the alkyl group having from C1 to C12 include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the like, wherein methyl, ethyl, n-propyl, isopropyl are preferred, and R isa、RbMore preferably methyl;
Ra、Rbthe rings may be linked to form a ring structure, and may be interlinked to form a ring, and such rings are preferably five-membered rings and six-membered rings, and may be, for example, a ring structure in which a cyclohexane ring, cyclopentane, 2-biphenylene group are linked (a spiro-fluorene structure is formed at the X position).
R is selected from C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, more preferably C1-C12 alkyl, C6-C30 aryl, C3-C30 heteroaryl,
examples of the C1-C12 alkyl group include the same ones as described above, and examples of the C6-C30 aryl group include: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, pyrenyl,
Figure BDA0001802199990000035
Fluoro, anthryl, benzo [ a ]]Anthracenyl, benzo [ c ]]Phenanthryl, triphenylene, benzo [ k ]]Fluoranthenyl, benzo [ g ]]
Figure BDA0001802199990000034
Radical, benzo [ b]Triphenylene, picene, perylene, etc., of which phenyl and naphthyl are preferred, and phenyl is more preferred; specific examples of the heteroaryl group having C3 to C30 include: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl, indazolyl, imidazopyridinyl, benzotriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl, benzisothiazolyl, benzooxadiazolyl, benzothiadiazolyl, dibenzofuranyl, dibenzothienyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like, but not limited thereto.
Preferred examples of the group of R include: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, idobenzene, terphenyl, tetrabiphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, triindene, isotridendene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pentacene, terphenyl, thiophene, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthoxazole, anthraoxazole, phenanthreneoxazole, isooxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4,5,9, 10-tetraaza, pyrazine, phenazine, phenoxazine, phenothiazine, fluoranthene, naphthyridine, azacarbazole, benzocaine, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, phenanthroline, 1,2, 3-triazole, 1, 4-oxadiazole, 1, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or combinations thereof. More preferred groups as R are phenyl, or naphthyl.
p is an integer of 0 to 7, preferably 0 or 1.
Ar in the general formula is selected from heteroaryl represented by the general formula A or substituted or unsubstituted aryl of C6-C30 which is different from the general formula (A),
Figure BDA0001802199990000041
in the formula A, L1Independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group, "+" represents the site of attachment to the parent nucleus, R1Selected from C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, multiple R1Q is an integer of 0 to 7, preferably 0 or 1, and two R's in adjacent positions1May be linked to form a ring, which may be aliphatic or aromatic, e.g. R at adjacent positions1Can be connected to form a ring structure such as a benzene ring, a fluorene ring and the like,
x is selected from O, S, NR2、SiR3R4Preferably NR2、O、S；R2、R3、R4Each independently selected from C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, R3And R4Can be interconnected to form a ring,
examples of the substituted or unsubstituted aryl group having C6 to C30, which is different from the aryl group of the general formula (A), include naphthyl, phenanthryl, benzophenanthryl, fluoranthenyl, anthryl, pyrene, dihydropyrene, fennel, perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, thiophene, benzothiophene, isobenzothiophene, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthoxazole, anthra , phenanthroizole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarbazine, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-crimp, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pyridine, piperidine, 2, 4-tetrazine, 3, 5-tetrazine, and their salts, Indolizines and benzothiadiazoles or combinations of these groups, which may also have corresponding substituents.
The above-mentioned "substituted or unsubstituted" means substituted by one or more groups selected from halogen and C1～C12Alkyl of (C)1～C12Alkoxy group of (C)6～C12Aryl of (C)3～C12The heteroaryl group, cyano group or hydroxyl group in (1) is substituted, and a connecting bond between the substituents "-" represents a ring structure, and represents a connecting site at an arbitrary position on the ring structure where a bond can be formed.
Above, C1～C12Alkyl of (C)6～C12Aryl of (C)3～C12As examples of the heteroaryl group in (1), the same ones as those mentioned above can be cited, and as the C1-C12 alkoxy group, there can be mentioned a group in which the above-mentioned examples of the C1-C12 alkyl group are bonded to-O-, for example, a methoxy group and an ethoxy groupPropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, propoxy and more preferably methoxy are preferred.
For the compound of the invention, the mother nucleus of the combination of fluorene and 2, 4-diphenylaniline is the main structure, and the compound can be ensured to have good hole transport performance or electron blocking performance by the defined substituent group with a special structure. The introduction of 2, 4-diphenyl benzene is extremely important for the compound of the invention, and the high steric hindrance of the 2, 4-diphenyl benzene directly influences the charge transport performance of the compound, so that charges are smoothly transferred in molecules, and the self-assembly property during film forming is more favorable for intermolecular charge transport due to the high steric hindrance.
On the other hand, the specific 2-position and 4-position substituted aniline is selected as a mother nucleus structure component of the molecule, the 2 and 4 positions are substituted to increase the thermal stability of the molecule and reduce the possibility of oxidation of the molecule, so that the service life of the device is prolonged, and meanwhile, due to the introduction of the 2-position substituent, the steric hindrance between molecules can be increased, so that the molecules are prevented from clustering, film formation during evaporation is facilitated, the potential energy between contact interfaces of the film layers is reduced, and charge transfer is facilitated. The parent nucleus of the compound of the present invention can be favorable to raising charge transmission efficiency and prolonging life.
As such a parent structure, it is preferable that the compound of the general formula (I) is a compound represented by the following general formula (I-1) or (I-2),
Figure BDA0001802199990000051
in the general formula (I-1) or (I-2),
Ra、Rbselected from C1-C6 alkyl, Ra、RbMay be linked to form a ring structure, p is 0 or 1, R is a substituted or unsubstituted aryl group of C6 to C12, preferably phenyl, biphenyl or naphthyl, and Ar is as defined above. When the compound is represented by the above formula (I-1) or (I-2), it is possible to provide a more excellent hole transportPerformance or electron blocking performance.
As for Ar, as the substituted or unsubstituted aryl group of C6 to C30 different from the general formula (a), a condensed ring aryl group or a condensed heterocyclic group having a large pi conjugate is preferable because the present inventors found that the charge mobility of the hole transport material can be improved to some extent by adjusting the degree of plane conjugation of the molecule, the HOMO level of the molecule can be adjusted by introducing a large conjugated condensed aromatic ring molecule into the designed molecule, the injection barrier of the charge is lowered, and the current efficiency is improved, and the operating voltage is lowered. The novel compound in which the fluorenyl group and the specific terphenyl group are combined and then coupled with the specific fused aromatic ring can realize the improvement and balance of the mobility of holes in the device and the reduction of the voltage of the device.
Such a group generally means a group in which pi electrons formed by fusing at least two aromatic rings or heteroaromatic rings can be delocalized over a wide range, and the planarity of such a group is more excellent. Examples of such groups include: naphthyl, phenanthryl, benzophenanthryl, fluoranthenyl, anthracyl, pyrene, dihydropyrene, fennel, perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenazine, indazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyrazole, benzopyrazole, pyridopyridine, pyridoimidazole, pyrazinoimidazole, quinoxalimidazole, benzoxazole, naphthoxazole, anthraxazole, phenanthrooxazole, benzothiazole, benzopyrazine, pyrimidine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarbazine, phenanthroline, benzotriazole, purine, pteridine, perylene, Indolizine and benzothiadiazole, or combinations of these groups. The groups can be used for improving the charge transmission efficiency, and simultaneously, the groups can be well matched with a mother nucleus combined by fluorene and 2, 4-diphenylaniline in space, so that molecules with proper steric hindrance are obtained, the film forming and the stability of the molecules are facilitated, and the service life can be correspondingly prolonged.
When Ar is formula A, L1Represents a single bond, or a substituted or unsubstituted C6-C12 arylene group, R1Selected from aryl of C6-C30 and heteroaryl of C3-C30, q is 0 or 1, X is preferably NR2、O、S；R2Is substituted or unsubstituted C6-C30 aryl. For the reason that the charge transport efficiency can be improved by achieving better planarity, it is also preferable that the general formula (A) is a group represented by the following general formula (A1),
Figure BDA0001802199990000061
(A1) in which X is selected from N-Ph, O, S, R1Is selected from aryl of C6-C12, r is 0 or 1, t is 0 or 1, r and t are not simultaneously 1, Ph represents phenyl, L1Represents a single bond, or a substituted or unsubstituted phenylene group, naphthylene group, or biphenylene group.
The compound of the present invention is also preferably a compound represented by the following general formula (II),
Figure BDA0001802199990000062
l, Ar is the same as above, and n is an integer of 0 to 10, wherein Ar is more preferably a group in which pi electrons formed by fusing two aromatic or heteroaromatic rings can be delocalized over a wide range, and preferred examples thereof are the same as above.
Further, for better charge transport performance, in the general formula (II), Ar is more preferably quinoline, benzopyrazole, pyridopyridine, or the like, and in the general formula (II), a structure of the general formula (II-1) is more preferably used, wherein L, Ar, and n have the same meanings as described above:
Figure BDA0001802199990000063
Figure BDA0001802199990000071
preferably, the compound of the present invention is selected from any one of the following compounds,
Figure BDA0001802199990000081
Figure BDA0001802199990000091
Figure BDA0001802199990000101
Figure BDA0001802199990000111
Figure BDA0001802199990000121
Figure BDA0001802199990000131
Figure BDA0001802199990000141
Figure BDA0001802199990000151
Figure BDA0001802199990000161
Figure BDA0001802199990000171
Figure BDA0001802199990000181
Figure BDA0001802199990000191
in addition, the invention also provides the application of the compound in an organic electroluminescent device.
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
Figure BDA0001802199990000201
Figure BDA0001802199990000211
Figure BDA0001802199990000221
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
Figure BDA0001802199990000222
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but is not limited to, the combination of one or more of BFH-1 through BFH-16 listed below.
Figure BDA0001802199990000231
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
Figure BDA0001802199990000232
Figure BDA0001802199990000241
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0001802199990000242
Figure BDA0001802199990000251
Figure BDA0001802199990000261
Figure BDA0001802199990000271
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
Examples
The present invention will be described in further detail below with reference to specific embodiments in order to make the present invention better understood by those skilled in the art.
Compounds of synthetic methods not mentioned in the examples are all starting products obtained commercially. Basic chemical raw materials such as petroleum ether, ethyl acetate, toluene, tetrahydrofuran, N-dimethylformamide, methylene chloride, cesium carbonate, potassium carbonate, palladium acetate, 2-dicyclohexylphosphine-2, 4, 6-triisopropylbiphenyl (XPhos), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (SPhos), tetrakis (triphenylphosphine) palladium, bis (4-biphenylyl) amine, carbazole, 1-bromo-3-chloro-5-fluorobenzene, 4-biphenylboronic acid, sodium tert-butoxide, and the like, which are used in examples, are commercially available in domestic chemical product markets.
Analytical testing of intermediates and compounds in the present invention used an ABCIEX mass spectrometer (4000QTRAP) and Brookfield nuclear magnetic resonance spectrometer (400M).
The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples. The compound represented by the general formula (1) is prepared by the steps of firstly carrying out Suzuki reaction on 2, 4-dibromoaniline and phenylboronic acid to obtain an intermediate 2, 4-diphenylaniline, then carrying out reaction on the intermediate and 2-bromo-9, 9-dimethylfluorene to obtain an intermediate A-1, and then carrying out Buchwald-Hartwig coupling reaction on a halide and the intermediate A-1.
A representative synthetic route for the compounds of the general formula of the present invention is as follows:
synthesis of intermediate A-2
Figure BDA0001802199990000272
The intermediate A-2 can be used for synthesizing the compound of the general formula (I-1), and the compound of the general formula (I-2) can be obtained similarly based on the same principle, and other homologues can be obtained based on the similar synthetic method.
Synthesis of A-1:
in a four-neck flask equipped with a condenser tube, raw materials of 2, 4-dibromoaniline (50g, 199mmol), phenylboronic acid (54g, 438mmol) and potassium carbonate (83g, 598mmol) are added into a mixed solvent of Tetrahydrofuran (THF) (600mL) and water (300mL), the mixture is stirred uniformly, and then Pd (PPh) is added under the protection of nitrogen gas3)4(9.2g, 7.97mmol), heated to 70 ℃ and reacted for 18 h. After cooling to room temperature, 500mL of water is directly added for liquid separation, the water phase is extracted twice by 300mL of ethyl acetate, the organic phases are combined, dried by anhydrous sodium sulfate and concentrated to obtain a crude product. Purifying the crude product by column chromatography (PE/EA, 5/1) to obtain light yellow powder 38 g;
synthesis of A-2:
a-1(38g, 135 mmol), 2-bromo-9, 9-dimethylfluorene ((41g, 148mmol), sodium tert-butoxide (32.4g, 337mmol), toluene (500mL) were added to a four-necked flask equipped with a condenser tube, and Pd (dppf) Cl was added thereto under nitrogen protection2(1.5g, 2.02mmol) and SPhos (1.7g, 4.05mmol), the reaction solution was heated to 100 ℃ and reacted for 18 h. After cooling to room temperature, 250mL of saturated brine was added directly for liquid separation, the aqueous phase was extracted three times with 200mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give a crude product. The crude product was purified by silica gel column chromatography (PE/EA, 10/1) to obtain 45g of a pale yellow solid.
General Synthesis of Compounds of formula
Figure BDA0001802199990000281
Synthesis example 1
Synthesis of Compound-1
Figure BDA0001802199990000282
Synthesis of intermediate M1
In a four-mouth bottle equipped with a condenser tube, raw materials of 4-dibenzothiophene borate (40g, 175mmol), bromobenzene (33g, 211mmol) and potassium carbonate (36g, 263mmol) are added into a mixed solvent of toluene (500mL), ethanol (100mL) and water (100mL), the mixture is stirred uniformly, and then Pd (PPh) is added under the protection of nitrogen gas3)4(4.1g, 3.51mmol) and heated to 100 ℃ for 18 h. After cooling to room temperature, 300mL of saturated saline solution is directly added for liquid separation, the water phase is extracted twice by 300mL of ethyl acetate, the organic phases are combined, dried by anhydrous sodium sulfate and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM, 20/1) to give 30g of a white powder;
synthesis of intermediate M2
A fully dried compound M1(20g, 76.8mmol) was charged into a dry three-necked flask equipped with a constant pressure dropping funnel, low temperature thermometer. Anhydrous tetrahydrofuran (300mL) was added, the mixture was stirred to dissolve the compound, and then the reaction system was cooled to-78 ℃ by a liquid nitrogen-ethanol bath under nitrogen protection. Then, s-BuLi (71mL, 1.3M,92.2mmol) is dripped through a constant pressure dropping funnel, the dripping speed is controlled to keep the temperature of the reaction system between-60 ℃ and-70 ℃, and the temperature is kept for 30min after the dripping is finished, so that the solution is mauve. 1, 2-dibromoethane (18.8g, 99.9mmol) was dissolved in THF (100mL), and the solution was gradually yellow by dropwise addition, after dropwise addition, the temperature was naturally raised to room temperature, and stirring was carried out for 4 hours. The reaction system was poured into 300mL of saturated brine, extracted twice with ethyl acetate (200mL), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give a solid, which was stirred with petroleum ether for 30min to give a white solid (18 g).
Synthesis of intermediate M3
At the fourth position equipped with a condenser tubeCharging raw material M2(17g, 50mmol), p-chlorobenzoic acid (9.4g, 60mmol) and potassium carbonate (10.4g, 75.2mmol) into a bottle, adding into a mixed solvent of toluene (200mL), ethanol (50mL) and water (50mL), stirring uniformly, and then adding Pd (PPh) under nitrogen protection3)4(0.6g, 0.5mmol) and heated to 100 ℃ for 18 h. After cooling to room temperature, 300mL of saturated brine was added directly for liquid separation, the aqueous phase was extracted twice with 300mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give a brown oil. The crude product was purified by silica gel column chromatography (PE/DCM, 20/1) to give 10g of a white powder;
synthesis of Compound-1
Intermediate A-2(10g, 22.8mmol), M3(10.2g, 27.4mmol) and sodium tert-butoxide (2.9g, 29.7mmol) were placed in a three-necked flask, 100mL of toluene solvent was added and stirred uniformly, and catalyst Pd2(dba)3(209mg, 0.228mmol) and SPhos (188mg, 0.457mmol) were added under nitrogen. Heating to 110 ℃, gradually making the solution brown red, and keeping the temperature for reaction overnight. Cooling, pouring into 200mL water, extracting with EA (200 mL. multidot.2), combining organic phases, drying with sodium sulfate, concentrating to obtain brown oil, purifying crude product with column chromatography to obtain PE/DCM, 5/1), and concentrating to obtain light yellow solid. The product was recrystallized from a mixed solvent of n-hexane and toluene (15/1) to give 10g of a pale yellow solid.
Synthesis example 2
Synthesis of Compound-3
Figure BDA0001802199990000291
Synthesis of intermediate M4
In a four-necked flask equipped with a condenser tube, 2-bromodibenzothiophene (20g, 76mmol), p-chlorobenzoic acid (14.3g, 91mmol) and potassium carbonate (15.8g, 114mmol) were added to a mixed solvent of toluene (200mL), ethanol (50mL) and water (50mL), stirred well, and then Pd (PPh) was added under nitrogen protection3)4(0.9g, 0.76mmol) and heated to 100 deg.C for 18 h. Cooling to room temperature, adding 300mL saturated salt solution directly, separating, extracting the water phase with 300mL ethyl acetate twice, combining the organic phases, drying with anhydrous sodium sulfate,concentrating to obtain light yellow solid. Recrystallizing the crude product by using methanol and dichloromethane to obtain 10g of white solid;
synthesis of Compound-3
Synthesis of Compound-3 referring to Compound-1, intermediate M4 was substituted for M3 to give a pale yellow solid.
Synthesis example 3
Synthesis of Compound-2
Figure BDA0001802199990000301
Synthesis of intermediate M5
The synthesis method of the intermediate M5 is the same as that of the intermediate M4, and the reaction raw material is changed into 4-bromodibenzothiophene. A white solid was obtained.
Synthesis of Compound-2
The synthesis of compound-2 is the same as the synthesis of compound-1. Intermediate M5 was used as the starting material in place of M3 to give a pale yellow solid.
Synthesis example 4
Synthesis of Compound-5
Figure BDA0001802199990000302
Synthesis of intermediate M6
Adding N-phenyl-3-bromocarbazole (70g, 218mmol), p-chlorobenzoic acid (41g, 260mmol) and potassium carbonate (45g, 325mmol) into a mixed solvent of THF (700mL) and water (100mL) in a four-mouth bottle equipped with a condenser tube, stirring uniformly, and then adding Pd under the protection of nitrogen2(dba)3(1.26g, 1.38mmol), heated to 60 ℃ and reacted for 18 h. After cooling to room temperature, 500mL of saturated brine was added directly for liquid separation, the aqueous phase was extracted twice with 500mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give a brown oil. The crude product was extracted with a mixed solution of petroleum ether and ethyl acetate and concentrated to give 65g of a yellow solid.
Synthesis of Compound-5
Referring to the synthesis of compound-1, intermediate M6 was used instead of M3 to give a pale yellow solid.
Synthesis example 5
Synthesis of Compound-6
Figure BDA0001802199990000311
Synthesis of intermediate M7
In a four-necked flask equipped with a condenser tube, 3-bromofluoranthene (20g, 71mmol), p-chlorophenylboronic acid (12.3g, 78mmol) and potassium carbonate (12.9g, 92.5mmol) were added to a mixed solvent of THF (350mL) and water (50mL), stirred well, and then Pd (PPh) was added under nitrogen protection3)4(822mg, 0.71mmol), heated to 100 ℃ and reacted for 18 h. After cooling to room temperature, 300mL of saturated brine was added directly for liquid separation, the aqueous phase was extracted twice with 300mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give a pale yellow solid. Recrystallizing the crude product by using methanol and dichloromethane to obtain 16g of yellow solid;
synthesis of Compound-6
Referring to the synthesis of compound-1, intermediate M7 was used instead of M3 to give a yellow solid.
Synthesis example 6
Synthesis of Compound-16
Figure BDA0001802199990000312
Synthesis of intermediate M8
Adding carbazole (20g, 120mmol), 4-bromo-2-chloro-1-fluorobenzene (30g, 144mmol), cesium carbonate (30g, 155mmol) and DMF (400mL) into a three-neck flask, heating to 100 ℃ under the protection of nitrogen, stirring for reaction for 20 hours, pouring the reaction liquid into 500mL of saturated saline solution after cooling, extracting twice with 300mL of ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, concentrating, and purifying a crude product by silica gel column chromatography (PE/EA, 7/1) to obtain 30g of a white solid.
Synthesis of intermediate M9
In a four-necked flask equipped with a condenser tube, M8(20g, 56mmol), phenylboronic acid (8) were charged.2g, 67mmol) and potassium carbonate (10g, 73mmol) are added into a mixed solvent of toluene (300mL), ethanol (150mL) and water (150mL), stirred uniformly and then Pd (PPh) is added under the protection of nitrogen3)4(1.3g, 1.12mmol), heated to 100 ℃ and reacted for 18 h. After cooling to room temperature, 300mL of saturated brine was added directly for liquid separation, the aqueous phase was extracted twice with 300mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give a pale yellow solid. The crude product was purified by silica gel column to obtain 11g of a yellow solid.
Synthesis of Compound-16
Referring to the synthesis method of the compound-1, intermediate M9 is used for replacing M3, xylene is used for replacing toluene as a solvent, and the temperature is refluxed to obtain a product which is yellow solid.
Synthesis example 7
Synthesis of Compound-250
Analogous compound-250 is obtained by the following synthetic route
Figure BDA0001802199990000321
The specific synthesis method can be referred to the synthesis conditions of the compound-1. A pale yellow solid was obtained.
Synthesis example 8
Synthesis of Compound-248
Figure BDA0001802199990000322
The specific synthesis method can be referred to the synthesis conditions of the compound-1. A yellow solid was obtained.
By replacing different Ar-X2(sometimes referred to in the art as aryl halides) different target compounds can be obtained. It should be noted that the above synthesis method is to link intermediate M to intermediate A-2 using Buchwald-Hartwig coupling, but the method is not limited to this coupling method, and those skilled in the art may select other methods such as but not limited to Stille coupling method, Grignard reagent method, Kumada-Tamao and the like, and any equivalent synthesis method may be used to link the intermediate M to intermediate A-2By effecting the substitution of a1And A2The purpose of the attachment to the benzopyrene ring may be selected as desired.
Device embodiments
The compounds of the present invention were used as hole transport materials in the light emitting layer, and HT-35 and HT-39 are comparative example 1 and comparative example 2, respectively.
The organic electroluminescent device of comparative example 1 was prepared as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to obtain HI-1 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT35 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 80 nm;
a luminescent layer of the device is evaporated in vacuum on the hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH4 is adjusted to be 0.1nm/s, the evaporation rate of the dye BFD-2 is set in a proportion of 3%, and the total film thickness of evaporation is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material ET29 of the device on the light-emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Comparative example 2
An organic electroluminescent device was produced in the same manner as in the comparative example, except that HT39 was replaced with the compound HT35
Device example 1
The compound of the present invention is used as a hole transport material.
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 1 synthesized in the present invention.
Device example 2
The compound of the present invention is used as a hole transport material.
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 2 synthesized in the present invention.
Device example 3
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 3 synthesized in the present invention.
Device example 4
An organic electroluminescent device was produced in the same manner as in the comparative example, except that H35 was replaced with compound 4 synthesized in the present invention.
Device example 5
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 5 synthesized in the present invention.
Device example 6
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 6 synthesized in the present invention.
Device example 7
An organic electroluminescent device was produced in the same manner as in the comparative example, except that HT35 was replaced with compound 7 synthesized in the present invention.
Device example 8
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 8 synthesized in the present invention.
Device example 9
An organic electroluminescent device was produced in the same manner as in the comparative example, except that HT35 was replaced with compound 24 synthesized in the present invention.
Device example 10
An organic electroluminescent device was produced in the same manner as in the comparative example, except that HT35 was replaced with compound 86 synthesized in the present invention.
Device example 11
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 250 synthesized in the present invention.
Device example 12
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that HT35 was replaced with compound 248 synthesized in the present invention.
Device example 13
An organic electroluminescent device was produced in the same manner as in the comparative example, except that HT35 was replaced with compound 257 synthesized in the present invention.
The testing method of the device comprises the following steps:
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in the examples and comparative examples and the lifetime of the devices were measured at the same luminance using a Photo-radiometer model ST-86LA model photoradiometer model PR750 from Photo Research corporation (photoelectric instrument factory, university of beijing) and Keithley 4200. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the luminance to the current density is the current efficiency.
The organic electroluminescent device properties are given in the following table:
Figure BDA0001802199990000341
Figure BDA0001802199990000351
in the case of the same other materials in the structure of the organic electroluminescent element, when the compound of the general formula of the present invention was used as a hole transport material instead of the prior art compound HT32 in the example of the comparative element, the operating voltage of the element prepared in example 5 was reduced as compared with 4.7V in comparative example 1, which was prepared using the prior art as a hole transport material, and the element prepared in the example had a voltage of 1000cd/m2The current efficiency measured under the brightness reaches 8.2cd/A, and is obviously improved compared with the comparative example of 7.1 cd/A; meanwhile, the common commercial material HT-39, 1000cd/m is compared2The current efficiency of the invention is significantly improved at brightness.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.

Claims (10)

1. A compound represented by the following general formula (I),
Figure FDA0001802199980000011
wherein L independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group,
Ra、Rbthe same or different, each is independently selected from alkyl of C1-C20, alkenyl of C1-C20, alkynyl of C1-C20, Ra、RbR is selected from alkyl of C1-C20, alkenyl of C1-C20, alkynyl of C1-C20, alkoxy of C1-C20, aryl of C6-C30 and heteroaryl of C3-C30,
p is an integer of 0 to 7,
ar is selected from heteroaryl represented by the general formula A, substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C3-C30 which is different from the general formula (A),
Figure FDA0001802199980000012
in the formula A, the reaction solution is prepared,
L1independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group, "-" represents a site of attachment to the parent nucleus,
R1selected from C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, multiple R1Identical or different, two R in adjacent position1May be linked to form a ring; q is an integer of 0 to 7, preferably 0 or 1,
x is selected from O, S, NR2、SiR3R4；R2、R3、R4Each independently selected from C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, R3And R4Can be interconnected to form a ring,
the above-mentioned "substituted or unsubstituted" means substituted by one or more groups selected from halogen and C1～C12Alkyl of (C)1～C12Alkoxy group of (C)6～C12Aryl of (C)3～C12The heteroaryl group, cyano group or hydroxyl group in (1) is substituted, and a connecting bond between the substituents "-" represents a ring structure, and represents a connecting site at an arbitrary position on the ring structure where a bond can be formed.
2. The compound according to claim 1, wherein the compound of the formula (I) is a compound represented by the following formula (I-1) or (I-2),
Figure FDA0001802199980000021
Ra、Rbis selected fromC1-C6 alkyl, Ra、RbCan be connected to form a ring structure, p is 0 or 1, R is substituted or unsubstituted aryl of C6-C12,
ar is as defined in formula (I).
3. The compound according to claim 1, wherein Ar is selected from a heteroaryl group represented by the general formula A, or a condensed aryl group or a condensed heteroaryl group having a large conjugated structure of C6 to C30,
in the formula A, L1Represents a single bond or a substituted or unsubstituted C6-C12 arylene group,
R1selected from aryl of C6-C30, heteroaryl of C3-C30, q is 0 or 1,
x is selected from NR2、O、S；R2Is substituted or unsubstituted C6-C30 aryl.
4. The compound according to claim 3, wherein the general formula (A) is a group represented by the following general formula (A1),
Figure FDA0001802199980000022
wherein X is selected from N-Ph, O, S, R1Selected from aryl of C6-C12, r is 0 or 1, t is 0 or 1, and r and t are not simultaneously 1, Ph represents phenyl,
L1represents a single bond or a substituted or unsubstituted phenylene group,
the condensed aryl or condensed heteroaryl with a large conjugated structure of C6-C30 is selected from substituted or unsubstituted naphthyl, phenanthryl, benzophenanthryl, fluoranthenyl, anthryl, pyrene, dihydropyrene, anise, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene, quinoline, isoquinoline, acridine, phenanthridine, benzopyrazole, pyridopyridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenazine, indazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalimidazole, benzoxazole, naphthoxazole, anthraxazole, phenanthroizole, benzothiazole, benzopyrazine, benzopyrimidine, quinoxaline, phenazine, phenanthroiidine, benzfuran, isobenzofuran, thiophene, phenanthrene, anthracene, phenanthrene, perylene, phenanthrene, benzopyrene, Naphthyridine, azacarbazole, benzocarbazine, phenanthroline, benzotriazole, purine, pteridine, indolizine, and benzothiadiazole, or combinations of these groups.
5. The compound according to claim 1, which is a compound represented by the following general formula (II),
Figure FDA0001802199980000023
l, Ar is as defined in claim 1, wherein n is an integer of 0 to 10.
6. The compound according to claim 1, which is one of the following specific compounds:
Figure FDA0001802199980000031
Figure FDA0001802199980000041
Figure FDA0001802199980000051
Figure FDA0001802199980000061
Figure FDA0001802199980000071
Figure FDA0001802199980000081
Figure FDA0001802199980000091
Figure FDA0001802199980000101
Figure FDA0001802199980000111
Figure FDA0001802199980000121
Figure FDA0001802199980000131
Figure FDA0001802199980000141
7. use of a compound according to any one of claims 1 to 6 as an electron blocking material, a hole transporting material or a hole injecting material.
8. Use of a compound according to any one of claims 1 to 6 in an organic electroluminescent device.
9. An organic electroluminescent element comprising a first electrode, a second electrode and an organic layer comprising at least one light-emitting layer interposed between the first electrode and the second electrode, the organic layer further comprising one or more layers selected from the group consisting of an electron-injecting layer, an electron-transporting layer, a hole-injecting layer, a hole-blocking layer and a hole-transporting layer, wherein the compound according to any one of claims 1 to 6 is contained in the organic layer.
10. The organic electroluminescent device according to claim 9, wherein the organic layer containing the compound is one or more layers selected from an electron blocking layer, a hole transporting layer, a hole injecting layer, and a light emitting layer.
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