CN115304574A - Heterocyclic compound and application thereof in organic electroluminescent device - Google Patents

Heterocyclic compound and application thereof in organic electroluminescent device Download PDF

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CN115304574A
CN115304574A CN202210909584.9A CN202210909584A CN115304574A CN 115304574 A CN115304574 A CN 115304574A CN 202210909584 A CN202210909584 A CN 202210909584A CN 115304574 A CN115304574 A CN 115304574A
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heterocyclic compound
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何睦
王湘成
王鹏
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention relates to the field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof in an organic electroluminescent device. The chemical structure of the heterocyclic compound is as follows:
Figure DDA0003773560000000011
the heterocyclic compound has excellent carrier transmission property and stability, is simple in molecular synthesis, can be used for connecting different substituents to be applied to hole transmission materials, light-emitting main body materials, electron transmission materials and other functional materials, can improve the light-emitting efficiency and the service life of a device, and reduces the production cost of the device.

Description

Heterocyclic compound and application thereof in organic electroluminescent device
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof in an organic electroluminescent device.
Background
Organic Light Emitting Diodes (OLEDs) are a type of self-luminous electronic components, and organic electroluminescent displays are generally driven at a low voltage and do not require an additional backlight, compared to Liquid Crystal Display (LCD) devices, and thus have advantages in power consumption and manufacturing processes. In addition, the organic electroluminescent display has the characteristics of high brightness, high contrast, excellent color expression, wide visual angle, high response speed and the like, and is widely concerned by academia and industry.
The working principle of the organic electroluminescent device is as follows: when a voltage is applied to the organic electroluminescent device, holes and electrons are injected from the anode and the cathode, respectively, and recombine in the light emitting layer to form excitons. When the excitons thus formed are restored from an unstable excited state having higher energy to a stable ground state having lower energy, the energy is released in the form of photons, and the device realizes light emission.
At present, in a common organic electroluminescent device, a light-emitting layer material is generally formed by blending a light-emitting host material and a light-emitting guest material, which is beneficial to inhibiting the concentration quenching effect of the light-emitting guest material and improving the light-emitting efficiency of the device. In addition, various functional layers such as a carrier injection layer and a carrier transmission layer are introduced into the device, so that the starting voltage of the device is favorably reduced, and the luminous efficiency is also favorably improved. For example, a typical organic electroluminescent device structure includes: anode/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/emission layer (EML, emission host material: emission guest material)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL)/cathode.
In recent years, the occupation of displays using organic electroluminescent devices in the consumer electronics field has increased year by year, which requires that the displays be driven at low power while the device lifetime and luminous efficiency are not lower than those of other conventional displays. Therefore, it is necessary to develop a functional layer material having a stable chemical structure and excellent performance. In particular, the material should have a suitable molecular weight and be easy to purify, so as to be suitable for deposition under vacuum at a higher purity; meanwhile, high glass transition temperature and thermal decomposition temperature are required to ensure thermal stability, and high electrochemical stability further ensures long service life of the device. The efficiency and stability of the existing materials are all to be further improved.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, it is an object of the present invention to provide a heterocyclic compound and its use in an organic electroluminescent device, which solve the problems of the prior art.
To achieve the above and other related objects, the present invention provides, in one aspect, a heterocyclic compound having a chemical structure represented by formula (1):
Figure BDA0003773559980000021
in the formula (1), Z is selected from O, S or NR 0 (ii) a Wherein R is 0 Selected from substituted or unsubstituted alkyl with C1-C12, substituted or unsubstituted cycloalkyl with C3-C12, substituted or unsubstituted aryl with C6-C30, and substituted or unsubstituted heteroaryl with C2-C30;
the ring A is selected from unsubstituted C6-C18 aromatic condensed rings or C2-C18 heteroaromatic condensed rings; the R is A Any hydrogen atom on the aromatic condensed ring or the heteroaromatic condensed ring can be substituted;
R A and R B Independently selected from deuterium, fluorine, chlorine, bromine, cyano, isonitrile group, trifluoromethyl, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C40 silyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, substituted or unsubstituted C1-C40 keto, substituted or unsubstituted C2-C40 alkoxycarbonyl, substituted or unsubstitutedAn aryloxycarbonyl group having 6 to 40 carbon atoms or a group represented by formula (2); or adjacent R A Bonding to form an aliphatic ring; m is selected from 0 to 8 and is an integer; n is selected from 0 to 6 and is an integer; and m and n are not 0 at the same time; and when m + n is not less than 2, each R A 、R B Are the same or different from each other; and at least one R A 、R B A group conforming to said formula (2);
＊-L 1 -L 2 -(L 3 -Ar) p (2)；
in the formula (2), L 1 And L 3 Each independently selected from single bond, substituted or unsubstituted C6-C40 arylene, substituted or unsubstituted C2-C40 heteroarylene; l is 2 Selected from nitrogen atom, substituted or unsubstituted C6-C40 arylene, substituted or unsubstituted C2-C40 heteroarylene; ar is selected from substituted or unsubstituted C6-C40 aryl and substituted or unsubstituted C2-C40 heteroaryl; p is selected from 1 to 5 and is an integer; and when p is more than or equal to 2, each L 3 Ar groups are the same or different from each other; * Is the bonding site of a chemical bond.
In another aspect, the present invention provides an organic layer comprising the heterocyclic compound.
According to a further aspect of the present invention there is provided the use of a heterocyclic compound as hereinbefore described, and/or an organic layer as hereinbefore described, in an organic electroluminescent device.
In another aspect, the present invention provides an organic electroluminescent device, including a first electrode, a second electrode, and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, or an electron transport layer, and the organic layer includes the heterocyclic compound.
In another aspect, the present invention provides a display or lighting device comprising the organic electroluminescent device as described above.
Compared with the prior art, the invention has the beneficial effects that:
the heterocyclic compound has excellent carrier transmission property and stability, is simple in molecular synthesis, can be used for connecting different substituents to be applied to hole transmission materials, luminescent main body materials, electron transmission materials and other functional materials, can improve the luminous efficiency and service life of devices, and reduces the production cost of the devices.
Drawings
Fig. 1 is a schematic view of a structure of an organic electroluminescent device in the embodiment.
FIG. 2 is a schematic view of another structure of the organic electroluminescent device in the example.
In the figure:
101. substrate
102. A first electrode
103. Hole injection layer
104. First hole transport layer
105. Second hole transport layer
106. Luminescent layer
107. Hole blocking layer
108. Electron transport layer
109. Second electrode
110. Cover layer
Detailed Description
Hereinafter, embodiments of the specifically disclosed heterocyclic compound and its application to an organic electroluminescent device are described in detail. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not to be limited to the specific embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments, and is not intended to limit the scope of the present invention; in the description and claims of the present application, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, the invention may be practiced using any method, device, and material that is similar or equivalent to the methods, devices, and materials described in examples herein, in addition to those described in prior art practice and the description herein.
The invention aims to provide a fluorene-based fused ring organic compound through a great deal of research and study. The spiro structure can improve the rigidity of molecules; meanwhile, the 1, 8-position hydrogen atom of the naphthalene fragment on the spiro ring is replaced by the cycloalkyl, so that the function of protecting the active site of the reaction is achieved. The above factors are beneficial to increasing the thermal stability and chemical stability of the molecule. The crossed stereo configuration and the larger steric hindrance can inhibit the intermolecular accumulation, and are suitable for designing amorphous organic molecules with high glass transition temperature. In addition, fluorene and its derivatives have good carrier transport characteristics and moderate front-line orbital energy level, and different substituent groups are introduced into different positions of molecules, so that the energy level can be regulated and controlled in a larger range, and various functional layer materials with excellent performance can be obtained. For example, when an electron-donating triarylamine group is attached, the resulting molecule can be used as a hole transport layer; and connecting the substituted s-triazine group with electron deficiency, wherein the obtained molecule can be used as a luminescent main body material or an electron transport layer according to different substituents on the s-triazine. On this basis, the present application has been completed.
Examples of the substituent in the present invention are described below, but the substituent is not limited thereto:
[ substituted or unsubstituted ] means substituted with one or more substituents selected from: deuterium, halogen group, cyano-group, nitro-group, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl and C2-C30 heteroaryl.
[ alkyl ] may be linear or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.
The above description of alkyl groups also applies to alkyl groups in aralkyl, aralkylamino, alkylaryl, and alkylamino groups.
[ cycloalkyl ] may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
[ heteroalkyl ] may be a linear or branched alkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl groups include, but are not limited to, alkoxy, alkylthio, alkylsulfonyl, silyl, and the like. Alkoxy groups can include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, and the like. Alkylthio groups may include, for example, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.
[ aryl ] is not particularly limited, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group can be substituted, for example, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, and the like. Further, two of the substituents may be bonded to each other to form a spiro ring structure, such as 9,9 '-spirobifluorenyl, spiro [ cyclopentane-1, 9' -fluorene ] group, or the like.
The description above for aryl groups applies to arylene groups except that arylene groups are divalent.
The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
[ heteroaryl ] comprises one or more of N, O, P, S, si and Se as heteroatoms. <xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , [ -9,9' - ], , , , , , , . </xnotran>
The above description of heteroaryl groups applies to heteroaryl groups in heteroarylamino and arylheteroarylamino groups.
The above description of heteroaryl is applicable to heteroarylenes, except that heteroarylenes are divalent.
[ alkoxycarbonyl ] is represented by-O-C (= O) -R ', wherein R' is an alkyl group according to the present invention.
[ aryloxycarbonyl ] is represented by-O-C (= O) -R ", wherein R" is an aryl group in the present invention.
[ keto ] is represented by R '"-C (= O) -R" ", wherein R'" is an alkyl or aryl group as described herein; r "" is an alkylene or arylene group as described herein.
[ bonded ring ] may mean, for example, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic heterocyclic ring.
An aliphatic hydrocarbon ring means a ring formed only of carbon and hydrogen atoms as a non-aromatic ring. The aliphatic hydrocarbon ring includes, but is not limited to, cycloalkylene, and specific examples may include cyclopropylene, cyclobutylene, cyclobutenyl, cyclopentylene, cyclopentenylene, cyclohexylene, cyclohexenylene, 1, 4-cyclohexadienylene, cycloheptenylene, cyclooctenylene, and the like.
The aromatic hydrocarbon ring is an aromatic ring formed only of carbon and hydrogen atoms. Specific examples of the aromatic hydrocarbon ring may include phenyl, naphthyl, anthryl, phenanthryl, perylenyl, anthryl, triphenylenyl, phenalkenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthenyl, benzofluorenyl, spirofluorenyl, and the like, but are not limited thereto.
By aliphatic heterocycle is meant an aliphatic ring containing one or more heteroatoms. Specific examples of the aliphatic heterocyclic ring may include, but are not limited to, an oxirane group, a tetrahydrofuranyl group, a 1, 4-dioxaylethyl group, a pyrrolidinyl group, a piperidinyl group, a morpholinyl group, an oxetanyl group, an azocyclohexane (azoxane) group, and the like.
The aliphatic hydrocarbon ring may be monocyclic or polycyclic.
The first aspect of the present invention provides a heterocyclic compound, wherein the chemical structure of the heterocyclic compound is represented by formula (1):
Figure BDA0003773559980000061
in the formula (1), Z is selected from O, S or NR 0 (ii) a Wherein R is 0 Selected from substituted or unsubstituted alkyl with C1-C12, substituted or unsubstituted cycloalkyl with C3-C12, substituted or unsubstituted aryl with C6-C30, and substituted or unsubstituted heteroaryl with C2-C30; a is selected from substituted or unsubstituted C6-C18 aromatic condensed rings or C2-C18 heteroaromatic condensed rings; said R is A Any hydrogen atom on the aromatic condensed ring or the heteroaromatic condensed ring can be substituted; r A And R B Each independently selected from deuterium, fluorine, chlorine, bromine, cyano, isonitrile, trifluoromethyl, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C40 silyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, substituted or unsubstituted C1-C40 keto, substituted or unsubstituted C2-C40 alkoxycarbonyl, substituted or unsubstituted C6-C40 aryloxycarbonyl, or a group represented by formula (2); or adjacent R A Bonding to form an aliphatic ring; m is selected from 0 to 8 and is an integer; n is selected from 0 to 6 and is an integer; and m and n are not 0 at the same time; and when m + n is not less than 2, each R A 、R B Are the same or different from each other; and at least one R A 、R B A group conforming to said formula (2).
Figure BDA0003773559980000071
In the formula (2), L 1 And L 3 Each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene group, a substituted or unsubstituted C2-C40 heteroarylene group; l is 2 Selected from nitrogen atom, substituted or unsubstituted C6-C40 arylene, substituted or unsubstituted C2-C40 heteroarylene; ar is selected from substituted or unsubstituted C6-C40 aryl and substituted or unsubstituted C2-C40 heteroaryl; p is selected from 1 to 5 and is an integer; and when p is more than or equal to 2, each L 3 Ar groups are the same or different from each other; * Is the bonding site of a chemical bond.
In the heterocyclic compound provided by the invention, in the formula (1), Z is selected from O, S or NR 0 (ii) a Wherein R is 0 Is selected from substituted or unsubstituted alkyl with C1-C12, substituted or unsubstituted cycloalkyl with C3-C12, substituted or unsubstituted aryl with C6-C30, and substituted or unsubstituted heteroaryl with C2-C30. More specifically, R 0 Selected from the group consisting of:
Figure BDA0003773559980000072
any one and only one of the carbons on the aromatic ring is a bonding site, or any one of the hydrogen atoms may be substituted with one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl.
In the heterocyclic compound provided by the invention, A is selected from unsubstituted C6-C18 aromatic condensed rings or C2-C18 heteroaromatic ringsA condensed ring; the number of ring atoms on the aromatic fused ring or the heteroaromatic fused ring is more than 6. The R is A Any hydrogen atom on the aromatic condensed ring or the heteroaromatic condensed ring can be substituted.
In some embodiments, the a group can be, for example
Figure BDA0003773559980000073
For the sake of corresponding description, compounds of formula (1) may be marked with two ×, as fused sites, i.e. formula (1) is represented by
Figure BDA0003773559980000081
And in the above-mentioned optional a groups, represents a fused site corresponding to that in formula (1). Wherein X 1 ～X 6 The same or different; x 1 ～X 6 Each independently selected from N, CH or CR c (ii) a Wherein R is c The radicals are as defined for R A And R is c And R A The same or different.
More specifically, the heterocyclic compounds are represented by the general structural formulas (3) to (6):
Figure BDA0003773559980000082
in formulae (3) to (6), X 1 ～X 6 The same or different; x 1 ～X 6 Each independently selected from N, CH or CR c (ii) a Wherein R is c The radicals are as defined for R A And R is c And R A The same or different; r is A 、R B Z, m and n are as defined in formula (1).
In some preferred embodiments, the heterocyclic compound has a chemical structure according to formulas (7) to (32):
Figure BDA0003773559980000083
Figure BDA0003773559980000091
wherein R is A 、R B Z, m and n are as defined in formula (1).
In the heterocyclic compound provided by the invention, m and n represent the number of substituent groups R, and m is selected from 0-8 and is an integer. More specifically, m may be selected from 0, 1,2, 3,4,5, 6,7, 8.n is selected from 0 to the largest integer which can be selected according to the difference of A groups, and specifically, n is selected from 0 to 6 and is an integer. More specifically, n may be selected from 0, 1,2, 3,4,5, 6. Preferably, m and n are not both 0. When m + n is not less than 2, each R A 、R B The same or different from each other.
In the heterocyclic compound provided by the invention, when m is more than 2, adjacent R A Bonded to form an aliphatic ring, e.g. to form cyclopentane, which forms with the adjacent A group when A is a naphthalene ring
Figure BDA0003773559980000092
In some embodiments of the invention, the group of formula (2) is 1 -L 2 -(L 3 -Ar) p . More specifically, the group represented by formula (2) is selected from one or more of the following structures:
Figure BDA0003773559980000093
wherein L is 1 ，L 2 ，L 3 Ar is as defined in formula (2). For example, in the group represented by the formula (2), p represents the number of Ar groups, and when p.gtoreq.2, the Ar groups are the same or different from each other.
In some embodiments, according to L 1 And L 2 From 1 to its largest integer that can be selected. Specifically, it is selected from integers of 1 to 5. More specifically, p may be selected from 1,2, 3,4, 5.
In some embodiments of the invention, L 1 、L 2 、L 3 Are identical or differentIn contrast, the L 1 、L 2 、L 3 Each independently selected from the group consisting of:
Figure BDA0003773559980000094
wherein U is independently selected from N, CH, CR 1 Or C a And satisfies that there are and only two U's C a ；R 1 Independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl and C2-C30 heteroaryl; * a is the bonding site of Ar, or corresponds to in formula (2).
V is selected from O, S, NR 2 、CR 3 R 4 、SiR 5 R 6 ；R 2 ～R 6 Each independently selected from C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl and C2-C30 heteroaryl; or, R 3 、R 4 Bonded to form a C5-C12 aliphatic ring, or bonded to form a C12-C30 aromatic condensed ring.
In some preferred embodiments of the invention, L is 1 、L 3 Each independently selected from a single bond or a group; l is 2 Selected from nitrogen atoms or the following groups. And, L 1 ,L 2 ,L 3 Identical to or different from each other:
Figure BDA0003773559980000101
Figure BDA0003773559980000111
for each of the above groups, any two and only two carbons on the aromatic ring are the bonding sites; or any one hydrogen atom may be substituted by one of deuterium, fluoro, chloro, bromo, cyano, nitro, trifluoromethyl, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl.
In some embodiments of the present invention, each time Ar appears, ar in formula (2) is selected from the following groups, and when the number of Ar is more than 1, different Ar are the same or different from each other:
Figure BDA0003773559980000112
wherein X is independently selected from N, CH, CR 7 Or C *b ；R 7 Independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl and C2-C30 heteroaryl; *b is L 3 The bonding site of (2).
Y is selected from O, S, NR 8 、CR 9 R 10 、SiR 11 R 12 ；R 8 ～R 12 Each independently selected from C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl and C2-C30 heteroaryl; or, R 9 、R 10 Bonded to form a C5-C12 aliphatic ring, or bonded to form a C12-C30 aromatic condensed ring.
In some embodiments of the present invention, specifically, the Ar may be selected from the following groups, for example, and when the number of Ar is more than 1, different Ar may be the same or different from each other:
Figure BDA0003773559980000121
Figure BDA0003773559980000131
for each of the above groups, any one and only one of the carbons on the aromatic ring is a bonding site, or any one of the hydrogen atoms may be substituted with one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl.
In the heterocyclic compound provided by the present invention, in the "substituted or unsubstituted" in the formula (1) and the formula (2), the substituent of the "substituted" is selected from one or more of deuterium, a halogen group (for example, fluorine, chlorine, bromine, etc.), a cyano group, a nitro group, a trifluoromethyl group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C1-C12 alkoxy group, a C1-C12 alkylthio group, a C6-C30 aryl group, and a C2-C30 heteroaryl group; and, R 0 、R A 、R B 、L 1 、L 2 、L 3 The substituents in Ar are the same or different from each other; or, the substituents at two adjacent positions may be linked to each other to form a C3-C12 aliphatic ring or a C12-C30 aromatic ring. The alicyclic ring is, for example, cyclohexane, adamantane or the like, and may be formed as a substituent of the fluorenyl group together with the fluorenyl group
Figure BDA0003773559980000141
And the like. The aromatic ring may be fluorene, or the like, and may be a substituent of the fluorene group to form spirofluorene together with the fluorene group.
In the heterocyclic compound provided by the present invention, the heterocyclic compound is selected from any one of the following chemical structures:
Figure BDA0003773559980000142
Figure BDA0003773559980000151
Figure BDA0003773559980000161
Figure BDA0003773559980000171
Figure BDA0003773559980000181
Figure BDA0003773559980000191
specifically, the above structure may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following. For example, deuterium, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C1-C12 alkoxy group, a C1-C12 alkylthio group, a C6-C30 aryl group, and a C2-C30 heteroaryl group.
More specifically, the substituent is selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl and the like.
In a second aspect, the present invention provides an organic layer comprising the heterocyclic compound of the first aspect of the present invention.
A third aspect of the invention provides the use of a heterocyclic compound according to the first aspect of the invention, and/or an organic layer according to the second aspect of the invention, in an organic electroluminescent device.
In a fourth aspect, the present invention provides an organic electroluminescent device, including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein the organic layers are in a bottom or top light-emitting device structure, and the organic layers may be in a single-layer structure or a multi-layer tandem structure in which two or more organic layers are laminated, and the organic layers include at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, or an electron transport layer. Can be prepared using common methods and materials for preparing organic electroluminescent devices. The organic layer includes the heterocyclic compound according to the first aspect of the present invention.
In the organic electroluminescent device provided by the invention, the first electrode is used as an anode layer, and the anode material can be a material with a large work function, so that holes can be smoothly injected into the organic layer. More examples are metals, metal oxides, combinations of metals and oxides, conductive polymers, and the like. The metal oxide may be, for example, indium Tin Oxide (ITO), zinc oxide, indium Zinc Oxide (IZO), or the like.
In the organic electroluminescent device provided by the invention, the second electrode is used as a cathode layer, and the cathode material can be a material with a small work function, so that electrons can be smoothly injected into the organic layer. The cathode material may be, for example, a metal or a multilayer structure material. The metal may be, for example, magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead, or alloys thereof. The cathode material is preferably selected from magnesium and silver.
In the organic electroluminescent device provided by the present invention, a material of the hole injection layer, preferably a material having a Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer, is used as a material that advantageously receives holes from the anode at a low voltage.
In the organic electroluminescent device provided by the invention, the material of the hole transport layer is a material having high mobility to holes and is suitable for receiving the holes from the anode or the hole injection layer and transporting the holes to the light emitting layer. Materials for the hole transport layer include, but are not limited to, organic materials of arylamines, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
In the organic electroluminescent device provided by the present invention, the material of the light emitting layer may be generally selected from materials having good quantum efficiency for fluorescence or phosphorescence as materials capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and from the electron transport layer, respectively, and combining the holes and the electrons.
In the organic electroluminescent device provided by the present invention, the material of the electron transport layer is a material having a high mobility to electrons and suitable as a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer.
In the organic electroluminescent device provided by the invention, the material of the covering layer generally has a high refractive index, so that the organic electroluminescent device can be beneficial to improving the light efficiency of the organic electroluminescent device, and is particularly beneficial to improving the external light efficiency.
In the organic electroluminescent device provided by the invention, the organic electroluminescent device is an organic photovoltaic device, an organic luminescent device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor and the like.
In another aspect, the invention provides a display or lighting device comprising an organic electroluminescent device according to the invention.
Specific methods for producing the above-described novel compounds of the present invention will be described in detail below by way of examples of synthesis, but the production method of the present invention is not limited to these examples of synthesis, and those skilled in the art can make modifications, equivalents, improvements, etc. without departing from the principles of the present invention and extend the methods to the scope of the claims of the present invention.
Synthesis examples:
representative synthetic routes for compounds of the invention:
Figure BDA0003773559980000211
wherein, when Z is O, S or NR 0 When Z' in the compound ii is OH, SH, HNR respectively 0 。
The main reactions involved in the synthesis of the compounds of the invention are: firstly, combining an iodo aromatic compound i and an acenaphthene derivative ii under a proper catalytic system to form an intermediate compound iii; in the second step, the intermediate compound iii forms aryl carbanion under the action of n-butyllithium, and further reacts with the 9-fluorenone derivative (compound iv) to generate the target compound.
In particular, for Z is NR 0 In some examples, compound ii can be synthesized by a one-step ullmann coupling reaction, as follows:
Figure BDA0003773559980000212
the specific steps of the synthesis reaction are as follows: in a dry three-neck flask, 5-bromoacenaphthene (1 eq) and an amino compound R were added in sequence under nitrogen atmosphere 0 -NH 2 (Compound vii,1 eq) and dry toluene, and after stirring well, sodium tert-butoxide (1.5 eq), tris (dibenzylideneacetone) dipalladium (0.5% eq), and tri-tert-butylphosphine (1.5% eq) were added in this order. And (3) uniformly mixing the systems, heating to reflux under the nitrogen atmosphere, and reacting overnight. Essentially no starting material remained as analyzed by thin layer chromatography and the heating was stopped. When the temperature of the reaction solution is reduced to below 45 ℃, adding a mixed solution of 5mL of concentrated hydrochloric acid (37% aqueous solution) and 100mL of deionized water into the reaction system, stirring and standing, separating by using a separating funnel, retaining an organic phase, extracting an aqueous phase by using toluene, combining with the retained organic phase, drying by using anhydrous magnesium sulfate, filtering, distilling under reduced pressure to remove the solvent, and purifying a crude product by flash silica gel column chromatography to obtain a compound ii.
In particular, for some embodiments, for example, when R A When the group is aryl, heteroaryl, or a group represented by formula (2), the following synthetic route can also be employed. Using starting compound i substituted with chlorine A Is retained as a chlorine atom, is synthesized by the aforementioned "two-step" process to give an intermediate compound v, which is subsequently subjected to a one-step Suzuki coupling reaction or Ullmann coupling reaction to join R A And (c) removing the solvent to obtain the target product.
Figure BDA0003773559980000213
Similarly, for other embodiments, for example, when R B When the group is aryl, heteroaryl or the group shown in the formula (2), halogenated fluorenone can also be used as a starting material to connect R by one-step suzuki-Miyaura coupling reaction or Ullmann coupling reaction B And (iv) to yield intermediate compound iv.
More specifically, the following shows a method for synthesizing a representative compound of the present invention. Unless otherwise specified, the compounds of the present invention to which no synthetic method is mentioned are commercially available; in the present invention, the mass spectrum was measured by a ZABHS type mass spectrometer (manufactured by Micromass, UK), and the nuclear magnetic resonance was measured by a Bruker 400MHz type nuclear magnetic resonance apparatus (manufactured by Bruker, germany);
synthesis of compound H4:
Figure BDA0003773559980000221
1. synthesis of Compounds iii-H4
1, 2-dihydroacenaphthene-5-ol (compounds i to H4,6.0g,35.3mmol, 1eq) and anhydrous tetrahydrofuran (350 mL) were sequentially added to a dry flask under a nitrogen atmosphere, stirred uniformly, and then sodium hydride (1.7g, 70.8mmol, 2eq) was slowly added to the aforementioned three-necked flask in portions at room temperature, avoiding vigorous generation of bubbles. After the addition of sodium hydride, the reaction system was yellow. 1-bromo-2-iodobenzene (compound ii-H4,10.0g,35.3mmol, 1eq) was slowly added dropwise to the reaction system at room temperature, and the reaction was continued at room temperature for 12 hours. Filtering the obtained reaction system, collecting filtrate, washing filter residue with anhydrous tetrahydrofuran, and combining washing liquor with the filtrate. The organic phases were combined and the solvent was removed by rotary evaporation. The crude product thus obtained was purified by flash column chromatography on silica gel (mobile phase: n-hexane/ethyl acetate mixed solvent) to obtain compound iii-H4 (6.9 g, yield 60.0%). Mass spectrum (m/z) =325.01[ M + ] H] +
2. Synthesis of Compounds iv-H4
Figure BDA0003773559980000222
Bibiphenyl-4-ylamine (compound ix-H4,12.9g,40.0mmol, 1eq), 2-bromo-9-fluorenone (compound viii-H4,10.4g,40.0mmol, 1eq) and anhydrous toluene (200 mL) were sequentially added to a dry three-necked flask under a nitrogen atmosphere, and after stirring uniformly, sodium tert-butoxide (5.8g, 60.0mmol, 1.5eq), palladium bis-dibenzylideneacetone (158.7mg, 0.28mmol,0.7 eq), and tri-tert-butylphosphine (10% n-hexane solution, 1.4mL,0.6mmol,1.5 eq) were further sequentially added. And (3) uniformly mixing the systems, heating to reflux in a nitrogen atmosphere, reacting for 7 hours, and then stopping heating. When the reaction solution was cooled to room temperature, a mixed solution of 5mL of concentrated hydrochloric acid (37% aqueous solution) and 100mL of deionized water was added to the reaction system, the mixture was stirred and allowed to stand, a separating funnel was used for separating liquid, the organic phase was retained, the aqueous phase was extracted with toluene (3 × 60 mL), the organic phase and the organic phase were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure, and the crude product was purified by flash silica gel column chromatography (mobile phase was a mixed solvent of n-hexane/ethyl acetate) to obtain compound iv-H4 (16.1 g, yield 80.6%). Mass spectrum (m/z) =500.19[ M + H ]] +
3. Synthesis of Compound H4
Under a nitrogen atmosphere, the compound iii-H4 (6.5g, 20.0mmol, 1eq) was dissolved in anhydrous tetrahydrofuran (200 mL). The solution was placed in a bath at-78 ℃ and sufficiently cooled, and then, under an atmosphere of nitrogen at this temperature, a n-hexane solution of n-butyllithium (concentration: 2.5M,8.0mL,20.0mmol, 1eq) was slowly dropped, and the mixture was kept at-78 ℃ and stirred for 1 hour. Subsequently, a solution of the compound iv-H4 (10.0 g,20.0mmol, 1eq) in anhydrous tetrahydrofuran (40 mL) was added dropwise to the reaction system under a nitrogen atmosphere at-78 ℃ and, after completion of the addition, the reaction system was slowly returned to room temperature and reacted for 8 hours. Deionized water (150 mL) was added slowly to the reaction system in order to quench the reaction, ethyl acetate (200 mL) was added, the mixture was stirred and allowed to stand for separation, the organic phase was collected with a separatory funnel, the aqueous phase was extracted with ethyl acetate (3X 50 mL), the organic phases were combined, and the solvent was removed by rotary evaporation. The crude product obtained is subsequently dissolved in glacial acetic acid (100 mL), warmed to 80 ℃ and 0.2mL of concentrated sulfuric acid added dropwiseStirring was continued for 4 hours at 80 ℃. The reaction was then cooled to room temperature and distilled water (200 mL) was added to precipitate a white solid. And filtering, collecting a filter cake, washing with deionized water and drying. The crude product was purified by flash column chromatography on silica gel (mobile phase was n-hexane/toluene mixed solvent) to obtain compound H4 (11.0 g, yield 75.5%). Starting from compounds i to H4, compound H4 is obtained via compounds iii to H4 in a total yield of 45.3% in the two-step reaction. Mass spectrum (m/z) =728.29[ M + H ]] + . Nuclear magnetic: 1 H NMR(400MHz,DMSO-d6):δ(ppm)7.94(dd,J＝7.3,1.6Hz,1H),7.84(dd,J＝7.5,1.0Hz,1H),7.64–7.53(m,9H),7.41–7.15(m,17H),7.09–6.99(m,2H),6.85(s,1H),6.84–6.80(m,1H),6.70(m,1H),3.54–3.37(m,2H),3.35–3.13(m,2H).
preparation of reference compound H4 the following compound (x) was synthesized: h30, H50, H99, H119, H164, H170, H188, H191, H192, H195, H205, H220, except that the starting compounds i-x, ii-x, viii-x and ix-x, respectively, are used in equivalent amounts instead of compounds i-H4, ii-H4, viii-H4 and ix-H4. The main raw materials used, the intermediates synthesized, the yields and the mass spectrum characterization data are shown in table 1. The nuclear magnetic characterization data are shown in table 2.
TABLE 1
Figure BDA0003773559980000241
Figure BDA0003773559980000251
TABLE 2
Figure BDA0003773559980000252
Figure BDA0003773559980000261
Figure BDA0003773559980000271
Synthesis of compound H15:
Figure BDA0003773559980000272
the synthesis of compounds iv-H15 is as follows:
Figure BDA0003773559980000273
2-bromo-9-fluorenone (compounds viii-H15,5.2g,20.0mmol, 1eq), compound ix-H15 (8.8g, 20.0mmol, 1eq), and degassed toluene (160 mL) were sequentially added to a three-necked flask under a nitrogen atmosphere, and after uniform mixing, potassium carbonate (6.9g, 50.0mmol, 2.5eq), tetrakis (triphenylphosphine) palladium (115.6mg, 0.1mmol,0.5 eq), ethanol (50 mL), and deionized water (50 mL) were sequentially added. Stirring is started, the system is fully mixed, the temperature is raised to reflux in the nitrogen atmosphere, the reaction is carried out for 10 hours, no raw material is left basically through thin layer chromatography analysis, and the heating is stopped. After the reaction system was cooled to room temperature, it was poured into 100mL of toluene, allowed to stand for separation, extracted with toluene (3X 80 mL), and the resulting organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The crude product thus obtained was subjected to flash silica gel column chromatography (mobile phase: n-hexane/dichloromethane mixed solvent) to obtain compound iv-H15 (9.3 g, yield 80.8%). Mass spectrum (m/z) =576.22[ M + [ H ]] + 。
Referring to the preparation method of the compound H4, the compound H15 was synthesized except that the compounds i-H4, ii-H4 and iv-H4 were replaced with the compounds i-H15, ii-H15 and iv-H15 in equivalent amounts, respectively, to obtain the objective compound H15 through two-step reaction. The total yield of the two-step reaction is 46.3 percent. Mass Spectrometry of Compound H15 (m/z) =834.31[ M + H ]] + Nuclear magnetic: 1H NMR (400MHz, DMSO-d 6) < delta > (ppm) 7.90-7.88 (m, 1H), 7.76 (dd, J =7.4,1.7Hz, 1H), 7.69-7.58 (m, 7H), 7.57-7.50 (m, 5H), 7.43-7.23 (m, 12H), 7.22-7.14 (m, 7H), 7.11-7.04 (m, 1H), 6.94 (s, 1H), 6.88 (dd, J =1.5,0.6Hz, 1H), 3.52-3.40(m,2H),3.38–3.32(m,2H),2.29(d,J＝0.8Hz,3H).
Referring to the preparation method of compound H15, the following compound (x) was synthesized: h48, H218, E1, E8, E11, E28, E39, E52, E58, E65, E71, E79, E86, E170, except that the starting compounds i-x, ii-x, viii-x and ix-x, respectively, are used in equivalent amounts instead of compounds i-H15, ii-H15, viii-H15 and ix-H15. The main raw materials used, the intermediates synthesized, the yields and the mass spectrum characterization data are shown in table 3. The nuclear magnetic characterization data are shown in table 4.
TABLE 3
Figure BDA0003773559980000281
Figure BDA0003773559980000291
TABLE 4
Figure BDA0003773559980000301
Figure BDA0003773559980000311
Figure BDA0003773559980000321
Synthesis of compound H71:
Figure BDA0003773559980000322
first, referring to the preparation method of the compound H4, the compounds v to H71 were synthesized except that the compounds i to H71 and iv to H71 were used in equal equivalents instead of the compounds i to H4 and iv to H4, respectively, to obtain the intermediate compounds v to H71 through two-step reactions. Subsequently, reference is again made to the preparation of the compounds iv to H4The target compound H71 was synthesized by the method except that the compounds viii-H4 and ix-H4 were replaced with the compounds v-H71 and vi-H71, respectively, in an equivalent amount, and the total yield of the three steps was 36.0%. Mass spectrum (m/z) =756.32[ M + [ H ]] + . Nuclear magnetism: 1 H NMR(400MHz,DMSO-d6)δ(ppm)7.92(dd,J＝7.5,1.6Hz,1H),7.84(dd,J＝7.4,1.6Hz,2H),7.57–7.52(m,4H),7.51–7.46(m,4H),7.39–7.32(m,3H),7.29(td,J＝7.4,1.5Hz,2H),7.25–7.15(m,12H),6.94(dd,J＝7.5,1.5Hz,1H),6.87(s,1H),6.71(d,J＝1.6Hz,1H),3.50–3.43(m,1H),3.36–3.21(m,2H),2.37(s,6H)。
referring to the preparation method of the compound H71, the compound H83 is synthesized by the following synthetic route.
Figure BDA0003773559980000323
The total yield of the three-step reaction is 36.5 percent. Mass spectrum (m/z) =895.36[ M + H ]] + . Nuclear magnetic: 1 H NMR(400MHz,DMSO-d6)δ7.91(dd,J＝7.5,1.5Hz,1H),7.77–7.71(m,1H),7.68–7.64(m,4H),7.57–7.51(m,4H),7.50–7.45(m,1H),7.44–7.07(m,27H),7.01(dd,J＝7.3,1.6Hz,1H),6.93(dd,J＝7.5,1.6Hz,1H),6.88(s,1H),6.70(d,J＝1.5Hz,1H),3.51–3.42(m,2H),3.38–3.21(m,2H)。
synthesis of Compound H115
Figure BDA0003773559980000331
First, referring to the preparation method of compound H4, compound v-H115 was synthesized except that compounds i-H115 and iv-H115 were used in equal equivalents instead of compounds i-H115 and iv-H115, respectively, to obtain intermediate compound v-H115 through a two-step reaction. Subsequently, the objective compound H115 was synthesized again with reference to the production process of the compounds iv to H15, and the point of time at which the reaction was stopped was judged by thin layer chromatography using the same solvent and catalyst system, except that the compounds viii to H15 and ix to H15 were replaced by the compounds v to H115 and vi to H115, respectively, in an equivalent amount, and the total yield of the three-step reaction was 35.5%. Mass spectrum (m/z) =884.38[ M + H ]] + . Nuclear magnetism: 1 H NMR(400MHz,DMSO-d6)δ7.91(dd,J＝7.5,1.5Hz,1H),7.84(dd,J＝7.5,1.6Hz,2H),7.75–7.70(m,2H),7.69(d,J＝7.4Hz,2H),7.60–7.54(m,2H),7.51–7.43(m,4H),7.40–7.19(m,14H),7.19–7.15(m,2H),7.02–6.98(m,1H),6.97–6.95(m,2H),6.87(s,1H),3.50–3.42(m,2H),3.37–3.20(m,2H),1.59(s,12H).
referring to the preparation method of compound H115, the following compound (x) was synthesized: h135, E123, E136, E139, E154, E157, with the difference that the starting compounds i-x, ii-x, iv-x and vi-x, respectively, are used in equivalent amounts instead of the compounds i-H115, ii-H115, iv-H115 and vi-H115. The main raw materials used, the intermediates synthesized, the yields and the mass spectrum characterization data are shown in table 5. The nuclear magnetic characterization data are shown in table 6.
TABLE 5
Figure BDA0003773559980000332
Figure BDA0003773559980000341
TABLE 6
Figure BDA0003773559980000342
Figure BDA0003773559980000351
Device embodiment:
the compounds of the invention used by the device are purified by sublimation, and the purity is more than 99.98 percent.
The compound can be used as a hole transport material of blue, green and red OLED devices in some embodiments; the other part of the embodiments can be used as an electron transport material of a blue OLED device; another part of the embodiments can be used as the main luminescent material of the red phosphorescent OLED device.
Blue device example 1:
preparation of blue organic electroluminescent device (as hole transport material)
The blue top-emitting organic electroluminescent device is manufactured according to the structure shown in figure 1, and the preparation process comprises the following steps: a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, a mixed material of compound 1 and compound 1-1 was evaporated as a hole injection layer 103 at a mixing ratio of 3 (mass ratio) to 97 (thickness) of 10nm, and then compound H48 of the present invention was evaporated to a thickness of 100nm to obtain a first hole transport layer 104. Then, compound 1-2 was deposited at a thickness of 20nm to obtain a second hole transport layer 105, and then compound 1-3 and compound 1-4 (thickness of 30 nm) were deposited at a deposition rate of 95. Then, compound 5 was sequentially evaporated to a thickness of 10nm to form a hole blocking layer 107, and compound 6 and LiQ in a mixture ratio of 4. Then, ytterbium (Yb) having a thickness of 3nm, magnesium (Mg) having a thickness of 10nm, and silver (Ag) were sequentially vacuum-deposited on the electron injection layer at a deposition rate of 1: 9 to form a second electrode 109. Then, 70nm of compound 7 was evaporated as a capping layer material to complete the fabrication of the organic light emitting device.
TABLE 7
Figure BDA0003773559980000361
Examples 2-7 of blue light device
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compounds in table 8 below were each substituted for compound H48 in forming the hole injection layer and the hole transport layer.
Comparative example 1
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound 1-1 was used instead of compound H48 in forming the hole injection layer and the hole transport layer.
The chemical structures of the compounds 1,1-2,1-3,1-4,5,6,7 and LiQ are shown in Table 7.
For the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each group of the devices of the blue light device example and the device of the comparative example 1 were produced and tested in the same batch, the operating voltage, the efficiency and the lifetime of the device of the comparative example 1 were respectively recorded as 1, and the ratio of the corresponding indexes of the devices of the blue light device examples 1 to 7 and the device of the comparative example 1 was respectively calculated, as shown in table 8.
TABLE 8
Hole transport layer Relative operating voltage Relative efficiency Relative life time
Comparative example 1 HTA 1 1 1
Blue light device example 1 H48 0.948 1.054 1.400
Blue light device example 2 H164 0.951 1.072 1.630
Blue light device example 3 H170 0.980 1.040 1.346
Blue device example 4 H188 0.977 1.090 1.468
Blue device example 5 H195 0.950 1.066 1.829
Blue device example 6 H218 0.968 1.087 1.765
Blue light device example 7 H220 0.955 1.045 1.910
Preparation of Red organic electroluminescent device (as hole transport material)
Red device example 1:
the red bottom light-emitting organic electroluminescent device is manufactured according to the structure shown in fig. 2, and the preparation process comprises the following steps: a transparent anode ITO film (150 nm in thickness) is formed on a glass substrate 101 to obtain a first electrode 102 as an anode. Subsequently, a mixed material of compound 1 and compound 1-1 was evaporated as a hole injection layer 103 on the surface of the anode by a vacuum evaporation method, with a mixing ratio of 3. Followed by vapor deposition of compound 1-1 to a thickness of 100nm on the hole injection layer to obtain a first hole transport layer 104. Subsequently, the compound H4 of the present invention was vapor-deposited on the first hole transport layer to a thickness of 10nm to obtain a second hole transport layer 105. On the second hole transport layer, the compound 2-3 and the compound 2-4 were co-evaporated at a mass ratio of 95. Then, on the organic light-emitting layer, a compound 5 was sequentially evaporated to form a hole blocking layer 107 (thickness 10 nm), and a compound 6 and LiQ at a mixing ratio of 4. Finally, magnesium (Mg) and silver (Ag) are mixed at the evaporation rate of 1: 9, and vacuum evaporation is carried out on the electron injection layer to be used as a second electrode 109, so that the manufacturing of the organic light-emitting device is completed.
Red light device examples 2-7
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compounds in table 10 below were each substituted for compound H4 in forming the second hole transport layer.
Comparative example 2
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound HTB was used instead of the compound H4 in forming the second hole transport layer.
Chemical structures of the compounds 1,5,6,7 and LiQ and HTA the chemical structures of the compounds 2-3,2-4 and HTB are shown in table 9, as described above.
TABLE 9
Figure BDA0003773559980000381
For the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. The devices of each set of red device examples were produced and tested in the same batch as the device of comparative example 2, the operating voltage, efficiency, and lifetime of the device of comparative example 2 were each recorded as 1, and the ratio of the respective indices of the devices of red device examples 1 to 7 to comparative example 2 was calculated, respectively, as shown in table 10.
Watch 10
Figure BDA0003773559980000382
Preparation of Green organic electroluminescent device (as hole transport material)
Green device example 1:
the green bottom light-emitting organic electroluminescent device is manufactured according to the structure shown in fig. 2, and the manufacturing process comprises the following steps: a transparent anode ITO film (150 nm in thickness) is formed on a glass substrate 101 to obtain a first electrode 102 as an anode. Subsequently, a mixed material of compound 1 and compound 1-1 described in table 5 was evaporated as a hole injection layer 103 on the surface of the anode by a vacuum evaporation method at a mixing ratio of 3. Followed by vapor deposition of compound 1-1 to a thickness of 100nm on the hole injection layer to obtain a first hole transport layer 104. Subsequently, a compound of the present invention H30 was vapor-deposited on the first hole transporting layer to a thickness of 40nm to obtain a second hole transporting layer 105. On the second hole transport layer, the compound 3-3 and the compound 3-4 were co-evaporated at a mass ratio of 90. Then, on the organic light-emitting layer, a compound 5 was sequentially evaporated to form a hole blocking layer 107 (thickness 10 nm), and a compound 6 and LiQ at a mixing ratio of 5. Finally, magnesium (Mg) and silver (Ag) are mixed at the evaporation rate of 1: 9, and the mixture is subjected to vacuum evaporation on the electron injection layer to be used as the second electrode 109, so that the manufacturing of the organic light-emitting device is completed.
Green device examples 2-7
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compounds in table 12 below were each substituted for compound H30 in forming the second hole transport layer.
Comparative example 3
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound HTC was used instead of the compound H30 in forming the second hole transport layer.
The structures of the main materials used in the above examples and comparative examples are shown in the following table 11:
TABLE 11
Figure BDA0003773559980000391
For the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (McScience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each set of green device examples was produced and tested in the same batch as the device of comparative example 3, the operating voltage, efficiency and lifetime of the device of comparative example 3 were each noted as 1, and the ratios of the respective indices of the green device examples 1 to 7 to the device of comparative example 3 were calculated, respectively, as shown in table 12.
TABLE 12
Figure BDA0003773559980000401
Preparation of blue organic electroluminescent device (as electron transport material)
Blue device example 8:
referring to the method for manufacturing a blue organic electroluminescent device in comparative example 1, a device in this example was manufactured except that the compound E11 of the present invention and LiQ (mixing ratio was 4 by mass).
Examples 9 to 15 of blue light emitting device
Organic electroluminescent devices were fabricated in the same manner as in blue device example 8, except that the compounds in table 13 below were each substituted for compound E11 in forming the electron transport layer.
Comparative example 4
An organic electroluminescent device was fabricated in the same manner as in blue device example 8, except that ETA was used instead of compound E11 in forming the electron transport layer. The structure of compound ETA is as follows:
Figure BDA0003773559980000402
for the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (McScience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each group of devices of the example blue light device and the device of comparative example 4 were produced and tested in the same batch, the operating voltage, efficiency, and lifetime of the device of comparative example 4 were each recorded as 1, and the ratio of the corresponding indices of the devices of examples 8 to 15 of the blue light device and the device of comparative example 4 was calculated, respectively, as shown in table 13.
Watch 13
Electron transport layer Relative operating voltage Relative efficiency Relative life time
Comparative example 4 ETA 1 1 1
Blue light device example 8 E11 0.868 1.151 1.424
Blue light device example 9 E28 0.920 1.178 1.315
Blue device example 10 E52 0.895 1.167 1.880
Blue light device example 11 E71 0.910 1.134 1.359
Blue light device example 12 E112 0.929 1.089 1.475
Blue light device example 13 E154 0.890 1.110 1.763
Blue light device example 14 E157 0.886 1.103 1.642
Blue light device example 15 E170 0.933 1.200 1.388
Preparation of Red organic electroluminescent device (as luminescent layer host material)
Red device example 8:
referring to the method for manufacturing a red organic electroluminescent device in comparative example 2, a device in this example was manufactured except that the compound E1 and the compounds 2 to 4 according to the present invention were co-evaporated at a mass ratio of 95.
Red light device examples 9 to 17
An organic electroluminescent device was fabricated in the same manner as in red device example 8, except that compounds in table 14 below were respectively substituted for compound E11 in forming the electron transport layer.
Comparative example 5
An organic electroluminescent device was fabricated in the same manner as in red device example 8, except that HOSTA was used instead of Compound E1 in forming the electron transport layer. The structure of compound HOSTA is as follows:
Figure BDA0003773559980000411
for the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each set of devices of the red device example and the device of comparative example 5 were produced and tested in the same batch, the operating voltage, efficiency and lifetime of the device of comparative example 5 were each noted as 1, and the ratio of the respective indices of the devices of red device examples 8 to 15 and comparative example 5 was calculated, respectively, as shown in table 14.
TABLE 14
Figure BDA0003773559980000421
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (16)

1. A heterocyclic compound having a chemical structure represented by formula (1):
Figure FDA0003773559970000011
in the formula (1), Z is selected from O, S or NR 0 (ii) a Wherein R is 0 Selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;
the ring A is selected from unsubstituted C6-C18 aromatic condensed rings or C2-C18 heteroaromatic condensed rings; said R is A Any hydrogen atom on the aromatic condensed ring or the heteroaromatic condensed ring can be substituted;
R A and R B Each independently selected from deuterium, fluorine, chlorine, bromine, cyano, isonitrile, trifluoromethyl, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C2-C40 silyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, substituted or unsubstituted C1-C40 keto, substituted or unsubstituted C2-C40 alkoxycarbonyl, substituted or unsubstituted C6-C40 aryloxycarbonyl, or a group represented by formula (2); or adjacent R A Bonding to form an aliphatic ring; m is selected from 0 to 8 and is an integer; n is selected from 0 to 6 and is an integer; and m and n are not 0 at the same time; and when m + n is not less than 2, each R A 、R B Are the same or different from each other; and at least one R A 、R B A group conforming to said formula (2);
＊-L 1 -L 2 -(L 3 -Ar) p
(2)；
in the formula (2), L 1 And L 3 Each independently selected from single bond, substituted or unsubstituted C6-C40 arylene, substituted or unsubstituted C2-C40 heteroarylene; l is a radical of an alcohol 2 Selected from nitrogen atom, substituted or unsubstituted C6-C40 arylene, substituted or unsubstituted C2-C40 is a heteroarylene group; ar is selected from substituted or unsubstituted C6-C40 aryl and substituted or unsubstituted C2-C40 heteroaryl; p is selected from 1 to 5 and is an integer; and when p is more than or equal to 2, each L 3 Ar groups are the same or different from each other; * Is a bonding site.
2. The heterocyclic compound according to claim 1, wherein in the substituted or unsubstituted of formula (1) or formula (2), the substituted substituent is selected from one or more of deuterium, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C1-C12 alkoxy group, a C1-C12 alkylthio group, a C6-C30 aryl group, a C2-C30 heteroaryl group; and, R 0 、R A 、R B 、L 1 、L 2 、L 3 The substituents in Ar are the same or different from each other; or, the substituents at two adjacent positions may be linked to each other to form an aliphatic ring having 3 to 12 carbon atoms or an aromatic ring having 12 to 30 carbon atoms.
3. The heterocyclic compound according to claim 1 or 2, which has a chemical structure represented by the formula (3) to the formula (6):
Figure FDA0003773559970000021
in formulae (3) to (6), X 1 ～X 6 The same or different; x 1 ～X 6 Each independently selected from N, CH or CR c (ii) a Wherein R is c The radicals are as defined for R A And each R is c May be the same or different from each other;
R A 、R B z, m and n are as defined in formula (1).
4. The heterocyclic compound according to claim 1, which has a chemical structure represented by the formula (7) to the formula (32):
Figure FDA0003773559970000022
Figure FDA0003773559970000031
R A 、R B z, m and n are as defined in formula (1).
5. The heterocyclic compound according to claim 1, wherein the group represented by formula (2) is selected from one or more of the following structures:
Figure FDA0003773559970000032
wherein L is 1 ，L 2 ，L 3 Ar is as defined in formula (2).
6. The heterocyclic compound according to claim 1 or 5, where L is 1 、L 3 Each independently selected from a single bond or a group; l is 2 Selected from nitrogen atoms or the following groups; and, L 1 ,L 2 ,L 3 Identical to or different from each other:
Figure FDA0003773559970000033
wherein U is independently selected from N, CH, CR 1 Or C a And satisfies that there are and only two U's as C a ；R 1 Independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl and C2-C30 heteroaryl; * a Is a bonding site for Ar, or corresponds to a star in formula (2);
v is selected from O, S, NR 2 、CR 3 R 4 、SiR 5 R 6 ；R 2 ～R 6 Each independently selected from C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl and C2-C30 heteroaryl; or, R 3 、R 4 Bonded to form a C5-C12 aliphatic ring, or bonded to form a C12-C30 aromatic condensed ring.
7. The heterocyclic compound of claim 6, wherein L is 1 、L 3 Each independently selected from a single bond or a group; l is 2 Selected from nitrogen atoms or the following groups. And, L 1 、L 2 、L 3 Identical to or different from each other:
Figure FDA0003773559970000034
Figure FDA0003773559970000041
any two and only two carbons on the aromatic ring of the any group are bonding sites; or any one hydrogen atom may be substituted by one of deuterium, fluoro, chloro, bromo, cyano, nitro, trifluoromethyl, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl.
8. The heterocyclic compound according to claim 1 or 6, wherein in the formula (2), ar is selected from the following groups, and when the number of Ar is more than 1, different Ar's are the same as or different from each other:
Figure FDA0003773559970000051
wherein X is independently selected from N, CH, CR 7 Or C *b ；R 7 Independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl and C2-C30 heteroaryl; * b Is L 3 The bonding site of (a);
y is selected from O, S, NR 8 、CR 9 R 10 、SiR 11 R 12 ；R 8 ～R 12 Each independently selected from C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl and C2-C30 heteroaryl; or, R 9 、R 10 Bonded to form a C5-C12 aliphatic ring, or bonded to form a C12-C30 aromatic condensed ring.
9. The heterocyclic compound according to claim 8, wherein Ar is selected from the group consisting of the following groups, and when the number of Ar is more than 1, different Ar's are the same as or different from each other:
Figure FDA0003773559970000052
Figure FDA0003773559970000061
Figure FDA0003773559970000071
any one and only one of the carbons on the aromatic ring is a bonding site, or any one of the hydrogen atoms may be substituted with one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl.
10. The heterocyclic compound according to claim 1, wherein R is 0 Selected from the group consisting of:
Figure FDA0003773559970000072
any one and only one of the carbons on the aromatic ring is a bonding site, or any one of the hydrogen atoms may be substituted with one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl.
11. The heterocyclic compound according to any one of claims 1 to 10, characterized in that the heterocyclic compound is selected from any one of the following chemical structures:
Figure FDA0003773559970000073
Figure FDA0003773559970000081
Figure FDA0003773559970000091
Figure FDA0003773559970000101
Figure FDA0003773559970000111
Figure FDA0003773559970000121
12. an organic layer comprising the heterocyclic compound according to claims 1 to 11.
13. Use of a heterocyclic compound according to any of the claims 1 to 11 and/or of an organic layer according to claim 12 in an organic electroluminescent device.
14. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the organic layer comprises the heterocyclic compound according to any one of claims 1 to 11.
15. The organic electroluminescent device of claim 14, wherein the organic electroluminescent device comprises an organic photovoltaic device, an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
16. A display or illumination device, characterized in that it comprises an organic electroluminescent device as claimed in any one of claims 14 to 15.
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