CN107531712B - Compound and organic electronic device comprising the same - Google Patents

Compound and organic electronic device comprising the same Download PDF

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CN107531712B
CN107531712B CN201680022783.0A CN201680022783A CN107531712B CN 107531712 B CN107531712 B CN 107531712B CN 201680022783 A CN201680022783 A CN 201680022783A CN 107531712 B CN107531712 B CN 107531712B
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phenanthryl
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CN107531712A (en
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郭芝媛
金振珠
金性昭
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Abstract

The present description relates to compounds and organic electronic devices comprising the same.

Description

Compound and organic electronic device comprising the same
Technical Field
The present invention claims priority and benefit of korean patent application No. 10-2015-0128575, filed on the korean intellectual property office at 2015, 9/10, the entire contents of which are incorporated herein by reference.
The present description relates to compounds and organic electronic devices comprising the same.
Background
By organic electronic device is meant a device that requires the exchange of charge between an electrode and an organic material using holes and/or electrons. Organic electronic devices can be broadly classified into the following two categories according to the operating principle. First, the organic electronic device is in the form of an electronic device: excitons are formed in the organic material layer by photons flowing into the device from an external light source, the excitons are separated into electrons and holes, and the electrons and holes are each transferred to a different electrode and used as a current source (voltage source). Second, the organic electronic device is in the form of an electronic device: holes and/or electrons are injected into an organic material semiconductor by applying a voltage or current to two or more electrodes, the semiconductor forms an interface with the electrodes, and the device operates by the injected electrons and holes.
Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an Organic Photoconductor (OPC), an organic transistor, and the like, and these devices all require a hole injecting or transporting material, an electron injecting or transporting material, or a light emitting material for driving the device. Hereinafter, the organic light emitting device will be mainly described in detail, but in the organic electronic device, a hole injecting or transporting material, an electron injecting or transporting material, or a light emitting material operates on a similar principle.
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, the organic material layer may have a multi-layered structure composed of different materials in many cases to improve efficiency and stability of the organic light emitting device, and for example, may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic material layer, electrons are injected from a negative electrode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons return to a ground state again. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and fast response.
In the organic light emitting device, materials used as the organic material layer may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron injection material, and the like, according to functions. In addition, the light emitting materials may be classified into blue, green and red light emitting materials according to light emitting colors, and yellow and orange light emitting materials required for realizing much better natural colors. Meanwhile, when only one material is used as a light emitting material, the following problems occur: the maximum emission wavelength is shifted to a long wavelength due to interaction between molecules, color purity is deteriorated, or efficiency of the device is reduced due to a light emission reduction effect, and thus, a host/dopant-based material may be used as a light emitting material to improve color purity and improve light emission efficiency through energy transfer.
In order for the organic light emitting device to sufficiently exhibit the above excellent characteristics, materials (for example, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.) forming the organic material layer in the device need to be supported by stable and effective materials first, but stable and effective materials for the organic material layer of the organic light emitting device have not been sufficiently developed so far. Therefore, there is a continuing need to develop new materials, and the need to develop such materials also applies to the other organic electronic devices described above.
Disclosure of Invention
Technical problem
The present specification is directed to providing compounds and organic electronic devices comprising the same.
Technical scheme
The present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure GDA0002366113180000021
In the chemical formula 1, the first and second,
Ar1is an unsubstituted aryl group, and is not particularly limited,
l is a substituted or unsubstituted arylene group,
Ar2and Ar3Are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted alkenyl; substituted or unsubstituted carbazolyl; or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms,
R1、R2and R7To R10Are identical or different from each otherAnd, each independently, hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylthio; substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted amine groups; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; substituted or unsubstituted carbazolyl; or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms, or may combine with an adjacent group to form a substituted or unsubstituted ring, and
R3to R6Are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylthio; substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; substituted or unsubstituted carbazolyl; or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
Further, the present specification provides an organic electronic device comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound of chemical formula 1.
Advantageous effects
The compound of the present specification is useful for an organic material layer material of an organic electronic device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like, and particularly, is useful as a hole injection material and/or a hole transport material.
In addition, when the compound of the present specification is used for an organic electronic device including an organic light emitting device, a driving voltage of the device may be reduced, light efficiency of the device may be improved, and life characteristics of the device may be improved by thermal stability of the compound.
Drawings
Fig. 1 shows an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4.
Fig. 2 shows an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a negative electrode 4.
< reference character >
1: substrate
2: positive electrode
3: luminescent layer
4: negative electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
Detailed Description
Hereinafter, the present specification will be described in more detail.
The present specification provides a compound represented by chemical formula 1.
According to an exemplary embodiment of the present specification, the compound represented by chemical formula 1 has an indolocarbazole ring structure as a core structure, and thus, a thin film having excellent heat resistance may be formed due to a high glass transition point, and high hole mobility and triplet energy level and excellent electron blocking characteristics may be expected.
Examples of the substituent in the present specification will be described below, but not limited thereto.
In the context of the present specification,
Figure GDA0002366113180000041
meaning the connected portions.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more are substituted, two or more substituents may be the same as or different from each other.
In this specification, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or a heterocyclic group containing one or more of N, O, S, Se and an Si atom, or a substituent which is unsubstituted or linked by two or more of the substituents exemplified above. For example, "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, biphenyl can also be an aryl group, and can be interpreted as a substituent with two phenyl groups attached.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
In the present specification, an alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof include methoxy group, ethoxy group, n-propoxy group, isopropoxy group (isopropoxy group), isopropyloxy group (i-propyloxy group), n-butoxy group, isobutoxy group, t-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3-dimethylbutyloxy group, 2-ethylbutoxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group and the like, but are not limited thereto.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but a cycloalkyl group having 3 to 30 carbon atoms is preferable, and specific examples thereof include 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, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl,
Figure GDA0002366113180000061
phenyl, styryl, and the like, but are not limited thereto.
In the present specification, a silyl group contains Si and is a substituent to which an Si atom is directly bonded as a group, represented by-SiR104R105R106Is represented by, and R104To R106The same or different from each other, may each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and heterocyclic groups. In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like.
In the present specification, the boron group may be-BR100R101And R is100And R101Equal to or different from each other, and may each be independently selected from: hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; substituted or unsubstituted, straight or branched chain alkyl groups having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
In the present specification, specific examples of the phosphine oxide group include, but are not limited to, diphenylphosphineoxide, dinaphthylphosphine oxide, and the like.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, quaterphenyl, and the like, but are not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 24. Specific examples of the polycyclic aryl group include naphthyl, anthryl, phenanthryl, pyrenyl, and the like,
Figure GDA0002366113180000062
A base,
Figure GDA0002366113180000063
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.
When the fluorenyl group is substituted, the group can be
Figure GDA0002366113180000071
Figure GDA0002366113180000072
And the like, but are not limited thereto.
In the present specification, the heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Figure GDA0002366113180000073
Azolyl group,
Figure GDA0002366113180000074
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl
Figure GDA0002366113180000075
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Figure GDA0002366113180000076
Azolyl group,
Figure GDA0002366113180000077
Diazolyl, thiadiazolyl, benzothiazolyl, dibenzofuranAnd the like, but are not limited thereto. In addition, examples of the heterocyclic group include a heterocyclic structure containing a sulfonyl group, for example
Figure GDA0002366113180000078
And the like.
In the present specification, "adjacent" groups may mean: a substituent that replaces an atom directly attached to the atom replaced by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that replaces an atom replaced by the corresponding substituent. For example, two substituents substituted at the ortho position of the phenyl ring and two substituents replacing the same carbon in the aliphatic ring may be interpreted as "adjacent groups" to each other.
In the present specification, the case where adjacent groups are bonded to each other to form a ring means that: adjacent groups are combined with each other to form a 5-to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above, and the rings may be monocyclic or polycyclic, may be aliphatic rings, aromatic rings or condensed forms thereof, but are not limited thereto.
In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from examples of cycloalkyl groups or aryl groups, except that the hydrocarbon ring is not monovalent.
In the present specification, amino means an amino group (-NH) therein2) A monovalent amine in which at least one hydrogen atom of (A) is substituted with another substituent, and is represented by-NR107R108Is represented by R107And R108Are the same or different from each other, and may each independently be a substituent composed of at least one of: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and heterocyclic (however, R107And R108Is not hydrogen). For example, the amine groups may be selected from: -NH2(ii) a A monoalkylamino group; a dialkylamino group; an N-alkylarylamino group; a monoarylamino group; a diarylamino group; n-arylheteroarylamino group, N-alkylheteroarylamino group, monoheteroarylamino group and diheteroarylamino group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino group, dimethylamino group,Ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracylamino, 9-methyl-anthracylamino, diphenylamino, ditolylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthrylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrfluorenylamino, N-biphenylfluorenylamino and the like, but not limited thereto.
In the present specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfonyl group, the N-arylalkylamino group, the N-arylheteroarylamino group, and the arylphosphino group is the same as the example of the aryl group described above. Specifically, examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3, 5-dimethyl-phenoxy group, 2,4, 6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenoxy group, 2-anthracenoxy group, 9-anthracenoxy group, 1-phenanthrenoxy group, 3-phenanthrenoxy group, 9-phenanthrenoxy group and the like, examples of the arylthio group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group and the like, examples of the arylsulfonyl group include benzenesulfonyl group, p-toluenesulfonyl group and the like, but examples thereof are not limited thereto.
In the present specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. Arylamine groups comprising two or more aryl groups can include monocyclic aryl groups, polycyclic aryl groups, or both monocyclic aryl groups and polycyclic aryl groups. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above. Specific examples of arylamine groups include aniline, naphthylamine, benzidine, anthracenamine, 3-methyl-aniline, 4-methylnaphthylamine, 2-methylbenzidine, 9-methylanthracene, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, carbazole, triphenylamino, and the like, but are not limited thereto.
In the present specification, examples of the heteroarylamino group include a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. A heteroarylamine group comprising two or more heteroaryls may comprise a monocyclic heteroaryl, a polycyclic heteroaryl, or both a monocyclic heteroaryl and a polycyclic heteroaryl. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of heteroaryl groups described above.
In this specification, an aromatic ring group may be monocyclic or polycyclic, and may be selected from examples of aryl groups, except that the aromatic ring group is not monovalent.
In the present specification, the divalent to tetravalent aromatic ring group may be monocyclic or polycyclic, and means an aromatic ring group having 2 to 4 binding positions in the aryl group, i.e., a divalent to tetravalent group. The above description of aryl groups can be applied with the exception that the aromatic ring groups are each divalent to tetravalent groups.
In the present specification, arylene means that two bonding positions, i.e., divalent groups, are present in an aryl group. The above description of aryl groups can be applied with the difference that the arylene groups are each divalent groups.
In the present specification, the above description of the alkyl group is applicable to the alkyl group in the aralkyl group, the alkylaryl group and the alkylamino group.
In this specification, the above description of heterocyclic groups applies to heteroaryl groups in heteroarylamine groups.
In the present specification, the above description of alkenyl groups can be applied to alkenyl groups among aralkenyl groups.
According to an exemplary embodiment of the present description, Ar1Is an unsubstituted aryl group having 6 to 30 carbon atoms.
According to an exemplary embodiment of the present description, Ar1Unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted naphthyl, unsubstituted anthracenyl, unsubstituted phenanthrenyl, unsubstituted pyrenyl or unsubstituted fluorenyl.
According to an exemplary embodiment of the present description, Ar1Is phenyl, biphenyl or naphthyl.
According to an exemplary embodiment of the present description, Ar1Is phenyl.
According to an exemplary embodiment of the present description, Ar1Is biphenyl.
According to an exemplary embodiment of the present description, Ar1Is naphthyl.
According to one exemplary embodiment of the present description, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to an exemplary embodiment of the invention, L is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene; substituted or unsubstituted terphenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted anthracenylene; substituted or unsubstituted phenanthrylene; substituted or unsubstituted pyrenylene; or a substituted or unsubstituted fluorenylidene group.
According to an exemplary embodiment of the present invention, L is phenylene, biphenylene, terphenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene or fluorenylene.
According to an exemplary embodiment of the present description, L is phenylene, biphenylene, or naphthylene.
According to an exemplary embodiment of the present description, L is phenylene.
According to an exemplary embodiment of the present description, L is biphenylene.
According to an exemplary embodiment of the present description, L is naphthylene.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to an exemplary embodiment of the present description, Ar2And Ar3The same or different from each other, and each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, or a fluorenyl group.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other and are each independently phenyl, biphenyl, terphenyl, or naphthyl.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a phenyl group.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a biphenyl group.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a naphthyl group.
According to an exemplary embodiment of the present description, Ar2And Ar3Are the same or different from each other, and are each independently a terphenyl group.
According to an exemplary embodiment of the present description, R1、R2And R7To R10Are identical to or different from each other and are each independentlyHydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylthio; substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted amine groups; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; substituted or unsubstituted carbazolyl; or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present description, R1Or R2Is an unsubstituted or substituted amine group with the following groups: alkyl, cycloalkyl, aryl, or heteroaryl containing one or more of N, O and S atoms.
According to an exemplary embodiment of the present description, R1Or R2Is amino substituted by phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl or fluorenyl.
According to an exemplary embodiment of the present description, R1、R2And R7To R10Is hydrogen.
According to an exemplary embodiment of the present description, R3To R6Are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylthio; substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or notA substituted boron group; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; substituted or unsubstituted carbazolyl; or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present description, R3To R6Are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; or a substituted or unsubstituted aryl group.
According to an exemplary embodiment of the present description, R3To R6Are the same or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, or a fluorenyl group.
According to an exemplary embodiment of the present description, R3To R6Is hydrogen.
According to one exemplary embodiment of the present specification, the compound represented by chemical formula 1 is represented by any one of the following compounds.
Figure GDA0002366113180000131
Figure GDA0002366113180000141
Figure GDA0002366113180000151
Figure GDA0002366113180000161
Figure GDA0002366113180000171
Figure GDA0002366113180000181
Figure GDA0002366113180000191
Figure GDA0002366113180000201
Figure GDA0002366113180000211
Figure GDA0002366113180000221
Figure GDA0002366113180000231
Compounds according to one exemplary embodiment of the present application may be prepared by the preparation methods described below. Representative examples will be described in the preparation examples to be described below, but substituents may be added or excluded, if necessary, and the positions of the substituents may be changed. In addition, starting materials, reactants, reaction conditions, and the like may be varied based on techniques known in the art.
Further, the present specification provides an organic electronic device comprising the above compound.
An exemplary embodiment of the present application provides an organic electronic device, including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound.
In the present specification, when one member is disposed "on" another member, this includes not only a case where one member is in contact with another member but also a case where another member exists between two members.
In the present specification, when a portion "includes" one constituent element, unless specifically described otherwise, this does not mean that another constituent element is not included, but means that another constituent element may also be included.
The organic electronic device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an Organic Photoconductor (OPC), and an organic transistor.
The organic material layer of the organic electronic device of the present specification may be composed of a single-layer structure, but may also be composed of a multi-layer structure in which two or more organic material layers are stacked. For example, the organic electronic device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic electronic device is not limited thereto, and a smaller number of organic layers may be included.
In one exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer simultaneously injecting and transporting holes, and the hole injection layer, the hole transport layer, or the layer simultaneously injecting and transporting holes includes the compound 1 of the formula.
According to another exemplary embodiment, the organic electronic device may be an organic electronic device having a structure (normal type) in which a positive electrode, one or more organic material layers, and a negative electrode are sequentially stacked on a substrate.
According to still another exemplary embodiment, the organic electronic device may be an organic electronic device having an inverted structure (inverted type) in which a negative electrode, one or more organic material layers, and a positive electrode are sequentially stacked on a substrate.
For example, the structure of the organic light emitting device of the present specification may have the structure as shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 shows an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In the structure as described above, the compound may be contained in the light-emitting layer.
Fig. 2 shows an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a negative electrode 4. In the structure as described above, the compound may be contained in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula 1-a.
[ chemical formula 1-A ]
Figure GDA0002366113180000251
n1Is an integer of 1 or more and is,
Ar11is a substituted or unsubstituted monovalent or higher benzofluorenyl group; a substituted or unsubstituted monovalent or higher fluorescent anthracene group; a substituted or unsubstituted monovalent or higher pyrenyl group; or substituted or unsubstituted monovalent or higher
Figure GDA0002366113180000252
The base group is a group of a compound,
L11is a direct bond; substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene group,
Ar12and Ar13Are the same or different from each other and are each independently substituted or unsubstituted aryl; substituted or unsubstituted silyl; a substituted or unsubstituted germanium group; substituted or unsubstituted alkyl; substituted or unsubstituted arylalkyl; or substituted or unsubstituted heteroaryl groups, or may be combined with each other to form a substituted or unsubstituted ring; and
when n is1When it is 2 or more, in parenthesesAre the same as or different from each other.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by chemical formula 1-a as a dopant of the light emitting layer.
According to an exemplary embodiment of the present description, L11Is a direct bond.
According to an exemplary embodiment of the present description, n1Is 2.
In an exemplary embodiment of the present specification, Ar11Is a divalent pyrenyl group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl or tert-butyl; or divalent unsubstituted or substituted by deuterium, methyl, ethyl or tert-butyl
Figure GDA0002366113180000253
And (4) a base.
According to an exemplary embodiment of the present description, Ar12And Ar13Are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to an exemplary embodiment of the present description, Ar12And Ar13The same or different from each other, and each independently is an aryl group which is unsubstituted or substituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or an alkyl group.
According to an exemplary embodiment of the present description, Ar12And Ar13Are identical or different from one another and are each independently unsubstituted or methyl-substituted aryl.
According to an exemplary embodiment of the present description, Ar12And Ar13Are the same or different from each other and are each independently a substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl; or a substituted or unsubstituted terphenyl group.
According to an exemplary embodiment of the present description, Ar12And Ar13Are the same or different from each otherAnd each independently is phenyl unsubstituted or substituted with silyl groups substituted with methyl, ethyl, isopropyl, tert-butyl, nitrile or alkyl groups.
According to an exemplary embodiment of the present description, Ar12And Ar13The same or different from each other, and each independently is a biphenyl group which is unsubstituted or substituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or an alkyl group.
According to an exemplary embodiment of the present description, Ar12And Ar13Are identical to or different from each other and are each independently a terphenyl group which is unsubstituted or substituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or an alkyl group.
According to an exemplary embodiment of the present description, Ar12And Ar13Are identical to or different from one another and are each independently substituted or unsubstituted heteroaryl having from 6 to 30 carbon atoms.
According to an exemplary embodiment of the present description, Ar12And Ar13The same or different from each other, and each independently is a heteroaryl group which is unsubstituted or substituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, or an alkyl group, or a phenyl group.
According to an exemplary embodiment of the present description, Ar12And Ar13Are the same or different from each other, and are each independently an unsubstituted or silyl-substituted dibenzofuranyl group substituted with a methyl, ethyl, isopropyl, tert-butyl, nitrile, or alkyl group, or a phenyl group.
According to an exemplary embodiment of the present specification, chemical formula 1-a is represented by the following compounds.
Figure GDA0002366113180000271
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula 2-a.
[ chemical formula 2-A ]
Figure GDA0002366113180000272
In the chemical formula 2-a,
G11is 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, or the following chemical formula
Figure GDA0002366113180000273
G12Is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacene-yl, 2-naphthacene-yl, 9-naphthacene-yl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 3-methyl-2-naphthyl, 4-methyl-1-anthryl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl or 3-fluoranthenyl,
G13and G14Are the same or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group,
g12is an integer of 1 to 5, and,
g13and g14Each is an integer of 1 to 4, and
when g is12To g14Each of which is 2 or more, two or more structures in parentheses are the same as or different from each other.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by chemical formula 2-a as a host of the light emitting layer.
According to an exemplary embodiment of the present description, G11Is 1-naphthyl.
According to an exemplary embodiment of the present description, G12Is 2-naphthyl.
According to an exemplary embodiment of the present description, G13And G14Is hydrogen.
According to an exemplary embodiment of the present specification, chemical formula 2-a is represented by the following compounds.
Figure GDA0002366113180000281
The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layer include the heterocyclic compound of the present specification, i.e., the compound represented by chemical formula 1.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by the following process: a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate by using a Physical Vapor Deposition (PVD) method (e.g., sputtering or electron beam evaporation) to form a first electrode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and then a material that can be used as a second electrode is deposited on the organic material layer. In addition to the above-described method, the organic light emitting device may be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a first electrode material on a substrate. In addition, in manufacturing an organic light emitting device, the compound represented by chemical formula 1 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution coating method. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.
In addition to the above-described methods, an organic light emitting device may be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (international publication No. 2003/012890). However, the manufacturing method is not limited thereto.
According to one exemplary embodiment of the present description, the first electrode is a positive electrode and the second electrode is a negative electrode.
According to another exemplary embodiment of the present description, the first electrode is a negative electrode and the second electrode is a positive electrode.
As the positive electrode material, a material having a large work function is generally preferred so that holes are smoothly injected into the organic material layer. Specific examples of positive electrode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.
As the negative electrode material, a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al and Mg/Ag; and the like, but are not limited thereto.
The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound of: which has the ability to transport holes and thus has the effect of injecting holes at the positive electrode and the excellent effect of injecting holes for the light-emitting layer or the light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the electron-injecting layer or the light-emitting materialAn electron injecting material, and also has an excellent ability to form a thin film. Preferably, the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, and quinacridone-based organic material
Figure GDA0002366113180000291
Organic materials, anthraquinones, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is suitably a material that can receive holes from the positive electrode or the hole injection layer to transport the holes to the light emitting layer and has a large mobility to the holes. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugated portion and a non-conjugated portion coexist, and the like, but are not limited thereto.
The electron blocking layer is a layer that can improve the lifetime and efficiency of the device by preventing holes injected from the hole injection layer from passing through the light emitting layer and entering the electron injection layer, and may be formed at an appropriate portion between the light emitting layer and the electron injection layer using a known material, if necessary.
The light emitting material of the light emitting layer is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and the electrons to emit light in the visible light region, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzene
Figure GDA0002366113180000301
Oxazole, benzothiazole-based and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) -basedA compound; a spiro compound; a polyfluorene; rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. Examples of the host material include a fused aromatic ring derivative or a heterocyclic ring-containing compound and the like. Specifically, examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but examples thereof are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene, having an arylamine group,
Figure GDA0002366113180000302
Diindenopyrene, and the like, styrylamine compounds are such compounds: wherein the substituted or unsubstituted arylamine is substituted with at least one arylvinyl group and one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamine groups are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is suitably a material that can well receive electrons from the negative electrode and transport the electrons to the light emitting layer and has a large mobility to the electrons. Specific examples thereof include: al complexes of 8-hydroxyquinoline; comprising Alq3The complex of (1); an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material used according to the prior art. In particular, the cathodeSuitable examples of materials are typical materials with a low work function, followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a negative electrode and has an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injecting layer, and also has an excellent ability to form a thin film. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,
Figure GDA0002366113180000311
Azole,
Figure GDA0002366113180000312
Diazole, triazole, imidazole,
Figure GDA0002366113180000313
Tetracarboxylic acid, fluorenylidene methane, anthrone and the like and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolato) chloride, gallium bis (2-methyl-8-quinolinolato) (o-cresol), aluminum bis (2-methyl-8-quinolinolato) (1-naphthol), gallium bis (2-methyl-8-quinolinolato) (2-naphthol), and the like, but are not limited thereto.
The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specific examples thereof include
Figure GDA0002366113180000314
Oxadiazole derivative or triazole derivative, phenanthroline derivative, BCP, and aluminum complexAnd the like, but are not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-side emission type, depending on the material used.
According to an exemplary embodiment of the present specification, the compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to an organic light emitting device.
Hereinafter, the present specification will be described in detail with reference to examples to specifically explain the present specification. However, the embodiments according to the present specification may be modified in various forms, and should not be construed that the scope of the present specification is limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully explain the present description to those of ordinary skill in the art.
< example >
< reaction formula 1> Synthesis of Compound B
Figure GDA0002366113180000321
(1) Preparation of Compound A
Under a nitrogen atmosphere, 10.0g (0.085mol) of indole was dissolved in 150ml of dehydrated diethyl ether, and hydrogen chloride gas generated by introducing 56.0g (0.55mol) of concentrated hydrochloric acid into 105.9g (1.08mol) of concentrated sulfuric acid over 1 hour was taken into the resultant solution while the resultant solution was stirred at ordinary temperature. After the reaction solution was stirred at room temperature for 15 hours, 60.5g of ethyl acetate and 151.6g of a saturated aqueous sodium hydrogencarbonate solution were added to the reaction solution. The aqueous layer was extracted with ethyl acetate (2X 100ml), and the organic layer was washed with saturated aqueous sodium bicarbonate (100ml) and distilled water (2X 100 ml). After the organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was filtered off, and the solvent was distilled and removed under reduced pressure. Thereafter, 150ml of toluene was added thereto, 2.5g of palladium/activated carbon was added thereto, and then the resultant mixture was stirred for 3 hours while being heated under reflux at 100 ℃. After the reaction solution was cooled to room temperature, palladium/activated carbon was filtered off and classified, and the solvent was distilled and removed under reduced pressure. The residue was purified by recrystallization, and then 7.4g (yield 36%) of compound a was obtained as a white solid.
MS[M+H]+＝233
(2) Preparation of Compound B
7.4g (0.030mol) of Compound A, 5.7g (0.036mol) of N, N-dimethylaminoacetaldehyde diethyl acetal and 55.0g of acetic acid are stirred under nitrogen at 120 ℃ for 8 hours while being heated under reflux. After the reaction solution was cooled to room temperature, precipitated crystals were filtered and washed with acetic acid (30 ml). The resulting solid was purified to obtain 5.2g (yield 67%) of compound B as a white solid.
MS[M+H]+＝257
< reaction formula 2> Synthesis of Compound C
Figure GDA0002366113180000331
Under a nitrogen atmosphere, compound B (7.68g, 30mmol) and bromobenzene (4.68g, 30mmol) were completely dissolved in 75ml of toluene, then sodium tert-butoxide (3.46g, 36mmol) was added thereto, and the resulting mixture was stirred while the temperature was raised until the resulting mixture was refluxed. When the mixture started to reflux, bis (tri-tert-butylphosphine) palladium (0.15g, 0.3mmol) was slowly added dropwise thereto. After 6 hours, the reaction was terminated, the temperature was lowered to normal temperature, and the resulting product was concentrated under reduced pressure, followed by column purification to prepare compound C (7.17 g).
MS[M+H]+＝333
< reaction formula 3> Synthesis of Compound D
Figure GDA0002366113180000332
Under a nitrogen atmosphere, compound B (7.68g, 30mmol) and 4-bromo-1, 1' -biphenyl (6.96g, 30mmol) were completely dissolved in 75ml of toluene, then sodium tert-butoxide (3.46g, 36mmol) was added thereto, and the resulting mixture was stirred while the temperature was increased until the resulting mixture was refluxed. When the mixture started to reflux, bis (tri-tert-butylphosphine) palladium (0.15g, 0.3mmol) was slowly added dropwise thereto. After 8 hours, the reaction was terminated, the temperature was lowered to normal temperature, and the resulting product was concentrated under reduced pressure, followed by column purification to prepare compound D (7.84 g).
MS[M+H]+＝409
< reaction formula 4> Synthesis of Compound E
Figure GDA0002366113180000341
Under a nitrogen atmosphere, compound B (7.68g, 30mmol) and 2-bromonaphthalene (6.18g, 30mmol) were completely dissolved in 75ml of toluene, then sodium tert-butoxide (3.46g, 36mmol) was added thereto, and the resulting mixture was stirred while the temperature was raised until the resulting mixture was refluxed. When the mixture started to reflux, bis (tri-tert-butylphosphine) palladium (0.15g, 0.3mmol) was slowly added dropwise thereto. After 11 hours, the reaction was terminated, the temperature was lowered to normal temperature, and the resulting product was concentrated under reduced pressure, followed by column purification to prepare compound E (8.71 g).
MS[M+H]+＝383
< preparation example 1> Synthesis of Compound 1
Figure GDA0002366113180000342
Compound C (7.17g, 22.2mmol) and 4-bromo-N, N' -diphenylaniline (7.17g, 22.2mmol) were completely dissolved in 60ml of xylene, then sodium tert-butoxide (2.56g, 26.6mmol) was added thereto, and the resulting mixture was stirred while the temperature was raised until the resulting mixture was refluxed. When the mixture started to reflux, bis (tri-tert-butylphosphine) palladium (0.11g, 0.22mmol) was slowly added dropwise thereto. After 12 hours, the reaction was terminated, the temperature was lowered to normal temperature, and the resulting product was concentrated under reduced pressure, followed by column purification to prepare 8.68g of compound 1.
MS[M+H]+＝576
< preparation example 2> Synthesis of Compound 2
Figure GDA0002366113180000351
9.54g of Compound 2 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and (4 '-bromo-N, N' -diphenyl) biphenyl-4-amine (8.86g, 22.2mmol) were used.
MS[M+H]+＝652
< preparation example 3> Synthesis of Compound 3
Figure GDA0002366113180000352
9.78g of Compound 3 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- (4-bromophenyl) -N-phenyl- [1,1' -biphenyl ] -4-amine (8.86g, 22.2mmol) were used.
MS[M+H]+＝652
< preparation example 4> Synthesis of Compound 4
Figure GDA0002366113180000361
12.27g of Compound 4 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (10.55g, 22.2mmol) were used.
MS[M+H]+＝728
< preparation example 5> Synthesis of Compound 5
Figure GDA0002366113180000362
11.86g of Compound 5 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -2-amine (10.55g, 22.2mmol) were used.
MS[M+H]+＝728
< preparation example 6> Synthesis of Compound 6
Figure GDA0002366113180000371
12.10g of Compound 6 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1' -biphenyl ] -4-yl) -4' -bromo-N-phenyl- [1,1' -biphenyl ] -4-amine (10.55g, 22.2mmol) were used.
MS[M+H]+＝728
< preparation example 7> Synthesis of Compound 7
Figure GDA0002366113180000372
12.66g of Compound 7 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N, N '-bis ([1,1' -biphenyl ] -4-yl) -4 '-bromo- [1,1' -biphenyl ] -4-amine (12.23g, 22.2mmol) were used.
MS[M+H]+＝804
< preparation example 8> Synthesis of Compound 8
Figure GDA0002366113180000381
11.12g of Compound 8 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1' -biphenyl ] -4-yl) -3' -bromo-N-phenyl- [1,1' -biphenyl ] -4-amine (10.55g, 22.2mmol) were used.
MS[M+H]+＝728
< preparation example 9> Synthesis of Compound 9
Figure GDA0002366113180000382
10.88g of Compound 9 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4' -bromo- [1,1 '-biphenyl ] -4-yl) - [1,1' -biphenyl ] -3-amine (12.23g, 22.2mmol) were used.
MS[M+H]+＝804
< preparation example 10> Synthesis of Compound 10
Figure GDA0002366113180000391
10.32g of Compound 10 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1' -biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1':3', 1' -terphenyl ] -4' -amine (12.23g, 22.2mmol) were used.
MS[M+H]+＝804
< preparation example 11> Synthesis of Compound 11
Figure GDA0002366113180000392
9.86g of Compound 11 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- (4-bromophenyl) -N-phenylnaphthalene-2-amine (8.28g, 22.2mmol) were used.
MS[M+H]+＝626
< preparation example 12> Synthesis of Compound 12
Figure GDA0002366113180000401
10.34g of Compound 12 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- (4-bromophenyl) -N- (naphthalen-2-yl) -naphthalen-2-amine (9.39g, 22.2mmol) were used.
MS[M+H]+＝676
< preparation example 13> Synthesis of Compound 13
Figure GDA0002366113180000402
10.24g of Compound 13 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- (4-bromophenyl) -N- (naphthalen-1-yl) -naphthalen-1-amine (9.39g, 22.2mmol) were used.
MS[M+H]+＝676
< preparation example 14> Synthesis of Compound 14
Figure GDA0002366113180000403
9.44g of compound 14 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that compound C (7.17g, 22.2mmol) and 6-bromo-N, N-diphenylnaphthalen-2-amine (8.28g, 22.2mmol) were used.
MS[M+H]+＝626
< preparation example 15> Synthesis of Compound 15
Figure GDA0002366113180000411
11.22g of Compound 15 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N, N '-bis ([1,1' -biphenyl ] -4-yl) -6-bromonaphthalene-2-amine (11.66g, 22.2mmol) were used.
MS[M+H]+＝778
< preparation example 16> Synthesis of Compound 16
Figure GDA0002366113180000412
11.41g of Compound 16 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N- ([1,1 '-biphenyl ] -3-yl) -N- ([1,1' -biphenyl ] -4-yl) -6-bromonaphthalene-2-amine (11.66g, 22.2mmol) were used.
MS[M+H]+＝778
< preparation example 17> Synthesis of Compound 17
Figure GDA0002366113180000421
9.72g of Compound 17 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and 7-bromo-N, N-diphenylnaphthalen-2-amine (8.28g, 22.2mmol) were used.
MS[M+H]+＝626
< preparation example 18> Synthesis of Compound 18
Figure GDA0002366113180000422
10.98g of Compound 18 was prepared by conducting reaction and purification in the same manner as in preparation example 1, except that Compound C (7.17g, 22.2mmol) and N, N '-bis ([1,1' -biphenyl ] -4-yl) -7-bromonaphthalene-2-amine (11.66g, 22.2mmol) were used.
MS[M+H]+＝778
< preparation example 19> Synthesis of Compound 19
Figure GDA0002366113180000431
Compound D (7.84g, 19.21mmol) and 4-bromo-N, N' -diphenylaniline (6.21g, 19.21mmol) were completely dissolved in 50ml of xylene, then sodium tert-butoxide (2.10g, 23.05mmol) was added thereto, and the resulting mixture was stirred while the temperature was raised until the resulting mixture was refluxed. When the mixture started to reflux, bis (tri-tert-butylphosphine) palladium (0.10g, 0.19mmol) was slowly added dropwise thereto. After 14 hours, the reaction was terminated, the temperature was lowered to normal temperature, and the resulting product was concentrated under reduced pressure, followed by column purification to prepare compound 19(9.26 g).
MS[M+H]+＝652
< preparation example 20> Synthesis of Compound 20
Figure GDA0002366113180000432
9.78g of Compound 20 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that Compound D (7.84g, 19.21mmol) and 4 '-bromo-N, N-diphenyl- [1,1' -biphenyl ] -4-amine (7.67g, 19.21mmol) were used.
MS[M+H]+＝728
< preparation example 21> Synthesis of Compound 21
Figure GDA0002366113180000441
9.58g of Compound 21 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that Compound D (7.84g, 19.21mmol) and N- (4-bromophenyl) -N-phenyl- [1,1' -biphenyl ] -4-amine (7.67g, 19.21mmol) were used.
MS[M+H]+＝728
< preparation example 22> Synthesis of Compound 22
Figure GDA0002366113180000442
11.11g of Compound 22 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that Compound D (7.84g, 19.21mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (9.13g, 19.21mmol) were used.
MS[M+H]+＝804
< preparation example 23> Synthesis of Compound 23
Figure GDA0002366113180000451
10.75g of compound 23 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -2-amine (9.13g, 19.21mmol) were used.
MS[M+H]+＝804
< preparation example 24> Synthesis of Compound 24
Figure GDA0002366113180000452
10.82g of compound 24 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and N- ([1,1' -biphenyl ] -4-yl) -4' -bromo-N-phenyl- [1,1' -biphenyl ] -4-amine (9.13g, 19.21mmol) were used.
MS[M+H]+＝804
< preparation example 25> Synthesis of Compound 25
Figure GDA0002366113180000461
10.19g of Compound 25 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that Compound D (7.84g, 19.21mmol) and N- ([1,1' -biphenyl ] -4-yl) -3' -bromo-N-phenyl- [1,1' -biphenyl ] -4-amine (9.13g, 19.21mmol) were used.
MS[M+H]+＝804
< preparation example 26> Synthesis of Compound 26
Figure GDA0002366113180000462
10.51g of compound 26 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and N- (4-bromophenyl) -N-phenylnaphthalene-2-amine (7.17g, 19.21mmol) were used.
MS[M+H]+＝702
< preparation example 27> Synthesis of Compound 27
Figure GDA0002366113180000471
10.25g of compound 27 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and N- (4-bromophenyl) -N- (naphthalen-2-yl) -naphthalen-2-amine (8.13g, 19.21mmol) were used.
MS[M+H]+＝752
< preparation example 28> Synthesis of Compound 28
Figure GDA0002366113180000472
10.64g of compound 28 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and N- (4-bromophenyl) -N- (naphthalen-1-yl) -naphthalen-1-amine (8.13g, 19.21mmol) were used.
MS[M+H]+＝752
< preparation example 29> Synthesis of Compound 29
Figure GDA0002366113180000481
10.19g of compound 29 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and 6-bromo-N, N-diphenylnaphthalen-2-amine (7.17g, 19.21mmol) were used.
MS[M+H]+＝702
< preparation example 30> Synthesis of Compound 30
Figure GDA0002366113180000482
10.28g of compound 30 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and 7-bromo-N, N-diphenylnaphthalen-2-amine (7.17g, 19.21mmol) were used.
MS[M+H]+＝702
< preparation example 31> Synthesis of Compound 31
Figure GDA0002366113180000491
10.15g of compound 31 was prepared by conducting reaction and purification in the same manner as in preparation example 19, except that compound D (7.84g, 19.21mmol) and N- ([1,1' -biphenyl ] -4-yl) -7-bromo-N-phenylnaphthalene-2-amine (8.63g, 19.21mmol) were used.
MS[M+H]+＝778
< preparation example 32> Synthesis of Compound 32
Figure GDA0002366113180000492
Compound E (8.71g, 22.79mmol) and 4-bromo-N, N' -diphenylaniline (7.36g, 22.79mmol) were completely dissolved in 60ml of xylene, then sodium tert-butoxide (2.63g, 27.35mmol) was added thereto, and the resulting mixture was stirred while the temperature was raised until the resulting mixture was refluxed. When the mixture started to reflux, bis (tri-tert-butylphosphine) palladium (0.12g, 0.23mmol) was slowly added dropwise thereto. After 11 hours, the reaction was terminated, the temperature was lowered to normal temperature, and the resulting product was concentrated under reduced pressure, followed by column purification to prepare compound 32(9.83 g).
MS[M+H]+＝626
< preparation example 33> Synthesis of Compound 33
Figure GDA0002366113180000501
11.51g of compound 33 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and 4 '-bromo-N, N-diphenyl- [1,1' -biphenyl ] -4-amine (9.09g, 22.79mmol) were used.
MS[M+H]+＝702
< preparation example 34> Synthesis of Compound 34
Figure GDA0002366113180000502
11.16g of compound 34 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and N- (4-bromophenyl) -N-phenyl- [1,1' -biphenyl ] -4-amine (9.09g, 22.79mmol) were used.
MS[M+H]+＝702
< preparation example 35> Synthesis of Compound 35
Figure GDA0002366113180000511
12.22g of Compound 35 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that Compound E (8.71g, 22.79mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (10.83g, 22.79mmol) were used.
MS[M+H]+＝778
< preparation example 36> Synthesis of Compound 36
Figure GDA0002366113180000512
12.31g of compound 36 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and N- ([1,1 '-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -2-amine (10.83g, 22.79mmol) were used.
MS[M+H]+＝778
< preparation example 37> Synthesis of Compound 37
Figure GDA0002366113180000521
12.37g of compound 37 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and N- ([1,1' -biphenyl ] -4-yl) -4' -bromo-N-phenyl- [1,1' -biphenyl ] -4-amine (10.83g, 22.79mmol) were used.
MS[M+H]+＝778
< preparation example 38> Synthesis of Compound 38
Figure GDA0002366113180000522
12.19g of the compound 38 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that the compound E (8.71g, 22.79mmol) and N- ([1,1' -biphenyl ] -4-yl) -3' -bromo-N-phenyl- [1,1' -biphenyl ] -4-amine (10.83g, 22.79mmol) were used.
MS[M+H]+＝778
< preparation example 39> Synthesis of Compound 39
Figure GDA0002366113180000531
10.93g of compound 39 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and N- (4-bromophenyl) -N-phenylnaphthalene-2-amine (8.50g, 22.79mmol) were used.
MS[M+H]+＝676
< preparation example 40> Synthesis of Compound 40
Figure GDA0002366113180000532
10.08g of Compound 40 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that Compound E (8.71g, 22.79mmol) and N- (4-bromophenyl) -N- (naphthalen-2-yl) -naphthalen-2-amine (9.64g, 22.79mmol) were used.
MS[M+H]+＝726
< preparation example 41> Synthesis of Compound 41
Figure GDA0002366113180000541
10.15g of Compound 41 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that Compound E (8.71g, 22.79mmol) and N- (4-bromophenyl) -N- (naphthalen-1-yl) -naphthalen-1-amine (9.64g, 22.79mmol) were used.
MS[M+H]+＝726
< preparation example 42> Synthesis of Compound 42
Figure GDA0002366113180000542
11.39g of compound 42 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and 6-bromo-N, N-diphenylnaphthalen-2-amine (8.50g, 22.79mmol) were used.
MS[M+H]+＝676
< preparation example 43> Synthesis of Compound 43
Figure GDA0002366113180000551
11.19g of Compound 43 was prepared by conducting the reaction and purification in the same manner as in preparation example 32, except that Compound E (8.71g, 22.79mmol) and 7-bromo-N, N-diphenylnaphthalen-2-amine (8.50g, 22.79mmol) were used.
MS[M+H]+＝676
< preparation example 44> Synthesis of Compound 44
Figure GDA0002366113180000552
10.62g of compound 44 was prepared by conducting reaction and purification in the same manner as in preparation example 32, except that compound E (8.71g, 22.79mmol) and N- ([1,1' -biphenyl ] -4-yl) -7-bromo-N-phenylnaphthalene-2-amine (10.23g, 22.79mmol) were used.
MS[M+H]+＝752
< Experimental example >
< Experimental examples 1-1>
Thinly coated with a thickness of
Figure GDA0002366113180000553
The glass substrate of Indium Tin Oxide (ITO) of (a) was put in distilled water in which a detergent was dissolved, and ultrasonic washing was performed. In this case, a product manufactured by Fischer co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes using distilled water. After completion of the washing with distilled water, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents, and drying was performed, and then the substrate was transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
The following formula of hexanitrile Hexaazatriphenylene (HAT) is thermally vacuum-deposited on the thus prepared transparent ITO electrode to
Figure GDA0002366113180000561
Thereby forming a hole injection layer.
[HAT]
Figure GDA0002366113180000562
The following compound 1, which is a material for transporting holes, was vacuum-deposited on the hole injection layer, thereby forming a hole transport layer.
[ Compound 1]
Figure GDA0002366113180000563
Subsequently, the following EB 1(TCTA) was vacuum deposited on the hole transport layer to
Figure GDA0002366113180000564
Thereby forming an electron blocking layer.
[EB 1]
Figure GDA0002366113180000571
Subsequently, the following BH and BD were vacuum deposited on the electron blocking layer at a weight ratio of 25:1 to
Figure GDA0002366113180000572
Thereby forming a light emitting layer.
Figure GDA0002366113180000573
The following compound ET1 and lithium quinolate (LiQ) were vacuum deposited on the light-emitting layer at a weight ratio of 1:1, thereby forming a thickness of
Figure GDA0002366113180000574
Electron injection and transport layers.
Figure GDA0002366113180000575
Lithium fluoride (LiF) and aluminumAre sequentially deposited on the electron injection and transport layers respectively to
Figure GDA0002366113180000586
And
Figure GDA0002366113180000581
thereby forming a cathode.
In the foregoing process, the deposition rate of the organic material is maintained at
Figure GDA0002366113180000582
Per second to
Figure GDA0002366113180000583
Per second, the deposition rates of lithium fluoride and aluminum of the negative electrode are respectively kept at
Figure GDA0002366113180000584
Second and
Figure GDA0002366113180000585
second, and the degree of vacuum during deposition was maintained at 2X 10-7Hold in the palm to 5 x 10-6And thus an organic light emitting device is manufactured.
< Experimental examples 1 and 2>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 2 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 3>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 3 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 4>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 4 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 5>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 5 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 6>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 6 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 7>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 7 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 8>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 8 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 9>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 9 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 10>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 10 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 11>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 11 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 12>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 12 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 13>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 13 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 14>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 14 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 15>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 15 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 16>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 16 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 17>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 17 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 18>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 18 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 19>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 19 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 20>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 20 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 21>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 21 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 22>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 22 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 23>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 23 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 24>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 24 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 25>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 25 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 26>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 26 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 27>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 27 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 28>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 28 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 29>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 29 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 30>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 30 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 31>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 31 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 32>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 32 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 33>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 33 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 34>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 34 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 35>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 35 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 36>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 36 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 37>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 37 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 38>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 38 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 39>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 39 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 40>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 40 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 41>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 41 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 42>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 42 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 43>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that compound 43 was used instead of compound 1 in experimental example 1-1.
< Experimental examples 1 to 44>
An organic light-emitting device was manufactured in the same manner as in experimental example 1-1, except that compound 44 was used instead of compound 1 in experimental example 1-1.
< comparative example 1-1>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that the following HT 1 was used instead of compound 1 in experimental example 1-1.
[HT 1]
Figure GDA0002366113180000621
< comparative examples 1 and 2>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that the following HT 2 was used instead of compound 1 in experimental example 1-1.
[HT 2]
Figure GDA0002366113180000631
< comparative examples 1 to 3>
An organic light-emitting device was fabricated in the same manner as in experimental example 1-1, except that the following HT 3 was used instead of compound 1 in experimental example 1-1.
[HT 3]
Figure GDA0002366113180000632
[ Table 1]
Figure GDA0002366113180000641
Figure GDA0002366113180000651
As shown in table 1, it can be seen that when the compounds of experimental examples 1-1 to 1-44 were used as a hole transport layer in an organic light emitting device, the compounds exhibited lower voltage and higher efficiency characteristics than those of comparative examples 1-1 to 1-3.
< Experimental example 2-1>
Thinly coated with a thickness of
Figure GDA0002366113180000652
The glass substrate of Indium Tin Oxide (ITO) of (a) was put in distilled water in which a detergent was dissolved, and ultrasonic washing was performed. In this case, a product manufactured by Fischer co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes using distilled water. After completion of the washing with distilled water, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents, and drying was performed, and then the substrate was transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
The following formula of hexanitrile Hexaazatriphenylene (HAT) is thermally vacuum-deposited on the thus prepared transparent ITO electrode to
Figure GDA0002366113180000661
Thereby forming a hole injection layer.
[HAT]
Figure GDA0002366113180000662
The following Compound 1 for transporting holes
Figure GDA0002366113180000663
Vacuum depositing on the hole injection layer, and then vacuum depositing the host RH and the dopant RD to
Figure GDA0002366113180000664
The thickness of (2) is used as a light emitting layer.
[ Compound 1]
Figure GDA0002366113180000665
Subsequently, the following compound E1 was reacted
Figure GDA0002366113180000678
And sequentially thermally vacuum-deposited as an electron injection and transport layer.
[E1]
Figure GDA0002366113180000671
By sequentially depositing lithium fluoride (LiF) and aluminum onto the electron transport layer respectively
Figure GDA0002366113180000672
And
Figure GDA0002366113180000673
forming a negative electrode, thereby manufacturing an organic light emitting device.
In the foregoing process, the deposition rates of the organic material, LiF and aluminum are maintained at
Figure GDA0002366113180000674
Per second, a,
Figure GDA0002366113180000675
Second and
Figure GDA0002366113180000676
per second to
Figure GDA0002366113180000677
In seconds.
< Experimental examples 2-2>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 2 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 3>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 3 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 4>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 4 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 5>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 5 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 6>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 6 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 7>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 7 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 8>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 8 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 9>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 9 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 10>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 10 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 11>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 11 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 12>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 12 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 13>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 13 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 14>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 14 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 15>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 15 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 16>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 16 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 17>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 17 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 18>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 18 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 19>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 19 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 20>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 20 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 21>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 21 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 22>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 22 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 23>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 23 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 24>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 24 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 25>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 25 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 26>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 26 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 27>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 27 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 28>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 28 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 29>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 29 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 30>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 30 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 31>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 31 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 32>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 32 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 33>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 33 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 34>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 34 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 35>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 35 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 36>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 36 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 37>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 37 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 38>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 38 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 39>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 39 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 40>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that compound 40 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 41>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 41 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 42>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 42 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 43>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 43 was used instead of compound 1 in experimental example 2-1.
< Experimental examples 2 to 44>
An organic light-emitting device was manufactured in the same manner as in experimental example 2-1, except that compound 44 was used instead of compound 1 in experimental example 2-1.
< comparative example 2-1>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that the following HT 1 was used instead of compound 1 in experimental example 2-1.
[HT 1]
Figure GDA0002366113180000721
< comparative example 2-2>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that the following HT 2 was used instead of compound 1 in experimental example 2-1.
[HT 2]
Figure GDA0002366113180000722
< comparative examples 2 to 3>
An organic light-emitting device was fabricated in the same manner as in experimental example 2-1, except that the following HT 3 was used instead of compound 1 in experimental example 2-1.
[HT 3]
Figure GDA0002366113180000731
[ Table 2]
Figure GDA0002366113180000732
Figure GDA0002366113180000741
As shown in table 2, it can be seen that when the compounds of experimental examples 2-1 to 2-44 were used as a hole transport layer in an organic light emitting device, the compounds exhibited lower voltage and higher efficiency characteristics than those of comparative examples 2-1 to 2-3.
Although the preferred exemplary embodiment of the present invention (hole transport layer) has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the present invention, which are also within the scope of the present invention.

Claims (10)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure FDF0000009814870000011
In the chemical formula 1, the first and second,
Ar1is unsubstituted phenyl; an unsubstituted biphenyl group or an unsubstituted naphthyl group,
l is unsubstituted phenylene; unsubstituted biphenylene; or an unsubstituted naphthylene group, or a substituted naphthylene group,
Ar2and Ar3Are the same or different from each other and are each independently unsubstituted phenyl; unsubstituted biphenyl; unsubstituted terphenyl; or unsubstituted naphthyl;
R1to R10Each independently hydrogen.
2. The compound of claim 1, wherein the compound represented by chemical formula 1 is any one selected from the following structural formulae:
Figure FDF0000009814870000021
Figure FDF0000009814870000031
Figure FDF0000009814870000041
Figure FDF0000009814870000051
Figure FDF0000009814870000061
Figure FDF0000009814870000071
Figure FDF0000009814870000081
Figure FDF0000009814870000091
Figure FDF0000009814870000101
Figure FDF0000009814870000111
Figure FDF0000009814870000121
3. an organic electronic device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
one or more layers of organic material disposed between the first electrode and the second electrode,
wherein one or more layers of the organic material layer comprise a compound according to any one of claims 1 to 2,
wherein the organic material layer includes a hole transport layer, and the hole transport layer includes the compound.
4. The organic electronic device of claim 3, wherein the organic electronic device further comprises one or two or more layers selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
5. The organic electronic device according to claim 3, wherein the organic electronic device is selected from the group consisting of organic light emitting devices, organic phosphorescent devices, organic solar cells, organic photoconductors, and organic transistors.
6. The organic electronic device according to claim 3, wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains a compound represented by the following chemical formula 1-A:
[ chemical formula 1-A ]
Figure FDF0000009814870000131
In the chemical formula 1-a,
n1is an integer of 1 or more and is,
Ar11is an unsubstituted monovalent or higher pyrenyl group,
L11is a direct bond and is characterized in that,
Ar12and Ar13Are the same or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 50 carbon atoms; or an unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing one or more of N, O, S, Si and Se as a heteroatom; and
when n is1At 2 or more, two or more structures in parenthesesThe same or different from each other.
7. The organic electronic device of claim 6, wherein L11Is a direct bond, Ar11Is a divalent pyrenyl group, Ar12And Ar13Are the same or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 50 carbon atoms; or a heterocyclic group having 6 to 30 carbon atoms containing one or more of N, O, S, Si and Se as a hetero atom, and n1Is 2.
8. The organic electronic device according to claim 3, wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains a compound represented by the following chemical formula 2-A:
[ chemical formula 2-A ]
Figure FDF0000009814870000132
In the chemical formula 2-a,
G11is 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl or the following chemical formula
Figure FDF0000009814870000141
G12Is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacene-yl, 2-naphthacene-yl, 9-naphthacene-yl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 3-Methyl-2-naphthyl, 4-methyl-1-anthryl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl or 3-fluoranthenyl,
G13and G14Is a hydrogen atom, and is,
g12is an integer of 1 to 5, and,
g13and g14Each is 4, and
when g is12And 2 or more, two or more structures in parentheses are the same as or different from each other.
9. The organic electronic device of claim 8, wherein G11Is 1-naphthyl, and G12Is 2-naphthyl.
10. The organic electronic device according to claim 6, wherein the light emitting layer comprises a compound represented by the following chemical formula 2-a:
[ chemical formula 2-A ]
Figure FDF0000009814870000142
In the chemical formula 2-a,
G11is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl or the following chemical formula
Figure FDF0000009814870000151
G12Is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, p-terphenyl-4-yl, p-terphenyl-1-naphthyl, p-phenanthryl, p-terphenyl-,M-terphenyl-2-yl, o-tolyl, m-tolyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 3-methyl-2-naphthyl, 4-methyl-1-anthryl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl or 3-fluoranthenyl,
G13and G14Is a hydrogen atom, and is,
g12is an integer of 1 to 5, and,
g13and g14Each is 4, and
when g is12And 2 or more, two or more structures in parentheses are the same as or different from each other.
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