CN111683952A - Compound and organic light emitting device including the same - Google Patents

Compound and organic light emitting device including the same Download PDF

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CN111683952A
CN111683952A CN201980011452.0A CN201980011452A CN111683952A CN 111683952 A CN111683952 A CN 111683952A CN 201980011452 A CN201980011452 A CN 201980011452A CN 111683952 A CN111683952 A CN 111683952A
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CN111683952B (en
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洪玩杓
金振珠
尹洪植
金善珉
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LG Chem Ltd
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Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.

Description

Compound and organic light emitting device including the same
Technical Field
The present specification relates to a compound and an organic light emitting device including the same.
The specification claims priority of korean patent application No. 10-2018-0065356 filed on 7.6.2018 to the korean patent office, the entire contents of which are incorporated herein.
Background
The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. If a voltage is applied to the organic light emitting device of such a structure, electrons and holes injected from the 2 electrodes are combined in pairs in the organic thin film and then quenched and emitted. The organic thin film may be formed of a single layer or a plurality of layers as necessary.
The material of the organic thin film may have a light-emitting function as needed. For example, as the material of the organic thin film, a compound which can constitute the light-emitting layer alone, or a compound which can function as a host or a dopant of the host-dopant light-emitting layer may be used. In addition, as a material of the organic thin film, a compound which can function as hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like can be used.
In order to improve the performance, lifetime, or efficiency of organic light emitting devices, development of materials for organic thin films is continuously required.
Disclosure of Invention
Technical subject
The present specification provides compounds and organic light emitting devices comprising the same.
Means for solving the problems
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure BDA0002614846360000021
In the above-described chemical formula 1,
ar1 is a monocyclic or bicyclic N-containing heteroaryl group substituted with at least one substituent selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group,
l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
m is an integer of 0 to 3, and when m is 2 or more, R1 may be the same or different from each other,
r1 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
n is an integer of 0 to 8, and when n is 2 or more, R2 may be the same or different from each other,
r2 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or 2 or more R2 may be combined with each other to form a substituted or unsubstituted ring.
In addition, the present application provides an organic light emitting device, comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound.
Effects of the invention
The compound according to an embodiment of the present application is used in an organic light emitting device, thereby improving the luminance of the organic light emitting device, extending the lifetime, reducing the driving voltage, improving the light efficiency, and improving the lifetime characteristics of the device by using the thermal stability of the compound.
In the compound represented by the above chemical formula 1, in a benzene ring such as a benzothienopyridine ring, an N-containing heterocyclic ring functioning as an electron acceptor is located at the position No. 6 of the benzothienopyridine ring, and a carbazole-based substance functioning as an electron donor is substituted at the position No. 8 of the benzothienopyridine ring. Since the electron donor unit and the electron acceptor unit are simultaneously present in the same molecule, both of them are advantageous for the transport of holes and electrons, and they are located at meta positions, the Highest Occupied Molecular Orbital (HOMO) and the lowest occupied molecular orbital (LUMO) are located at appropriate positions, and thus, the stability of the substance is high, thereby having the effects of high efficiency and long life when used as a material for an organic layer of an organic light emitting device.
Drawings
Fig. 1 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked.
Fig. 2 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4 are stacked in this order.
[ description of symbols ]
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron blocking layer
8: hole blocking layer
9: electron transport layer
10: electron injection layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the above chemical formula 1.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, and a heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms 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-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpen, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
Figure BDA0002614846360000051
And a fluorenyl group, but is not limited thereto.
In the present specification, the heteroaryl group contains 1 or more heteroatoms other than carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, Si, S, and the like. The number of carbon atoms of the heteroaryl group is not particularly limited, but the number of carbon atoms is preferably 2 to 60 or 2 to 30. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Figure BDA0002614846360000052
Azolyl group,
Figure BDA0002614846360000053
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Figure BDA0002614846360000054
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiapyrrolyl, phenanthrolinyl (phenylanthralinyl group), isoquinoyl
Figure BDA0002614846360000055
Azolyl, thiadiazolyl, phenothiazinyl, phenoxazine
Figure BDA0002614846360000056
Oxazine groups and their fused structures, and the like, but are not limited thereto.
In the present specification, arylene means a group having two binding sites on an aryl group, i.e., a 2-valent group. The above description of aryl groups applies, except that they are each a 2-valent group.
In this specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. The above description of heteroaryl groups applies, except that they are each a 2-valent group.
In the present specification, the phrase "adjacent 2 groups are bonded to each other to form a ring" in a substituent means that adjacent groups are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
In the present specification, the ring means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or aromatic and aliphatic fused ring, and may be selected from the cycloalkyl groups and the aryl groups described above, except that the hydrocarbon ring has a valence of 1.
In the present specification, the aromatic ring may be a monocyclic ring or a polycyclic ring, and may be selected from the above-mentioned illustrations of aryl groups, except that it is not 1-valent.
In the present specification, the heterocyclic ring contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The heterocyclic ring may be monocyclic or polycyclic, may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the group consisting of the heteroaryl groups exemplified above, except that the heterocyclic ring has a valence of 1.
In one embodiment of the present specification, L1 is a direct bond or a substituted or unsubstituted arylene group.
In one embodiment of the present specification, L1 is a direct bond or an arylene group.
In one embodiment of the present specification, L1 represents a direct bond,
Figure BDA0002614846360000061
Figure BDA0002614846360000062
In one embodiment of the present specification, L2 is a direct bond.
In one embodiment of the present specification, Ar1 denotes a triazinyl group substituted with at least one substituent selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; a pyrimidinyl group substituted with at least one substituent selected from a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; a quinolyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group; a quinazolinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; or a quinoxalinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, Ar1 denotes a triazinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; a pyrimidinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; a quinolyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; a quinazolinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; or a quinoxalinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
In one embodiment of the present specification, Ar1 is a triazinyl group substituted with at least one substituent selected from the group consisting of a phenyl group substituted or unsubstituted with a nitrile group, a biphenyl group substituted or unsubstituted with a nitrile group, a dibenzofuranyl group, and a dibenzothiophenyl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a phenyl group substituted or unsubstituted with a nitrile group, a biphenyl group substituted or unsubstituted with a nitrile group, a dibenzofuranyl group, and a dibenzothiophenyl group; a pyrimidinyl group substituted with at least one substituent group selected from the group consisting of a phenyl group substituted or unsubstituted with a nitrile group, a biphenyl group substituted or unsubstituted with a nitrile group, a dibenzofuranyl group, and a dibenzothiophenyl group; a quinolyl group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; a quinazolinyl group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group; or a quinoxalinyl group substituted with at least one substituent selected from the group consisting of a phenyl group and a biphenyl group.
In one embodiment of the present specification, Ar1 represents a triazinyl group substituted with at least one substituent selected from a substituted or unsubstituted aryl group and a heteroaryl group; or a quinazolinyl group substituted with an aryl group.
In one embodiment of the present specification, Ar1 is a triazinyl group substituted with at least one substituent selected from an aryl group and a heteroaryl group, the aryl group being substituted with a nitrile group or unsubstituted; or a quinazolinyl group substituted with an aryl group.
In one embodiment of the present specification, Ar1 is a triazinyl group substituted with at least one substituent selected from the group consisting of a phenyl group substituted or unsubstituted with a nitrile group, a biphenyl group substituted or unsubstituted with a nitrile group, a dibenzofuranyl group, and a dibenzothiophenyl group; or a quinazolinyl group substituted with a phenyl group.
In one embodiment of the present specification, Ar1 is represented by the following chemical formula A-1 or A-2.
[ chemical formula A-1]
Figure BDA0002614846360000071
[ chemical formula A-2]
Figure BDA0002614846360000081
In the above chemical formulas A-1 and A-2,
at least one of X1 to X3 is N, and the remainder are CH,
at least one of X4 and X5 is N, and the remainder are CH,
ar2 to Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Figure BDA0002614846360000082
is referred to and aboveThe position at which L1 of chemical formula 1 binds.
In one embodiment of the present disclosure, X1 to X3 are N.
In one embodiment of the present disclosure, at least 2 of the X1 to X3 are N, and the rest are CH.
In one embodiment of the present disclosure, X1 and X2 are N, and X3 is CH.
In one embodiment of the present disclosure, X1 and X3 are N, and X2 is CH.
In one embodiment of the present disclosure, X2 and X3 are N, and X1 is CH.
In one embodiment of the present disclosure, one of X1 to X3 is N, and the others are CH.
In one embodiment of the present disclosure, X1 is N, and X2 and X3 are CH.
In one embodiment of the present disclosure, X2 is N, and X1 and X3 are CH.
In one embodiment of the present disclosure, X3 is N, and X1 and X2 are CH.
In one embodiment of the present specification, X4 and X5 are N.
In one embodiment of the present specification, one of X4 and X5 is N, and the others are CH.
In one embodiment of the present specification, X4 is N, and X5 is CH.
In one embodiment of the present specification, X5 is N, and X4 is CH.
In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently represents an aryl group or a heteroaryl group which is substituted or unsubstituted with a nitro group.
In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, which is substituted or unsubstituted with a nitro group.
In one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group.
In one embodiment of the present specification, Ar4 is an aryl group.
In one embodiment of the present specification, Ar4 is a phenyl group.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.
[ chemical formula 1-1]
Figure BDA0002614846360000091
[ chemical formulas 1-2]
Figure BDA0002614846360000092
[ chemical formulas 1-3]
Figure BDA0002614846360000101
[ chemical formulas 1 to 4]
Figure BDA0002614846360000102
In the above chemical formulas 1-1 to 1-4,
l1, L2, and Ar1 are the same as defined in the above chemical formula 1,
ar10 and Ar11, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
x10 is CRR' or NR ",
r, R', and R "are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, Ar10 and Ar11 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
In one embodiment of the present specification, Ar10 and Ar11, which are the same or different from each other, are each independently a phenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted or unsubstituted with an aryl group.
In one embodiment of the present specification, Ar10 and Ar11, which are the same or different from each other, are each independently a phenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group.
In one embodiment of the present specification, X10 is CRR ', and R' are the same or different and each independently a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, X10 is CRR ', and R' are the same or different and each independently an alkyl group.
In one embodiment of the present specification, X10 is CRR ', and R', which may be the same or different from each other, are each independently a methyl group, an ethyl group, a propyl group, or a butyl group.
In one embodiment of the present specification, X10 is NR "and R" is a substituted or unsubstituted aryl group.
In one embodiment of the present specification, X10 is NR "and R" is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In one embodiment of the present specification, X10 is NR, and R "is phenyl, biphenyl, or naphthyl.
In one embodiment of the present specification, X10 is NR, and R "is phenyl.
In one embodiment of the present specification, the compound of the above chemical formula 1 is selected from compounds represented by the following structural formulae.
Figure BDA0002614846360000111
Figure BDA0002614846360000121
Figure BDA0002614846360000131
Figure BDA0002614846360000141
Figure BDA0002614846360000151
Figure BDA0002614846360000161
Figure BDA0002614846360000171
Figure BDA0002614846360000181
Figure BDA0002614846360000191
Figure BDA0002614846360000201
The compound according to an embodiment of the present application can be produced by a production method described later.
The compound represented by the above chemical formula 1 starts from a benzothienopyridine ring, as an example, by using a known synthesis method, for example, a Pd-utilizing cross-coupling reaction for forming a carbon-carbon bond as described in j.org.chem.,42,1821(1977), j.am.chem.soc.,101,4992(1977), chem.rev.,95,2457(1995), j.org.chem.,53,918(1988), etc.; the cross-coupling reaction of forming a carbon-nitrogen bond using Pd described in angelw.chem.int.ed.1998, 37,2046, etc. was carried out by the following production method shown in reaction formula 1.
For example, the compound of the above chemical formula 1 may be prepared into a core structure as shown in the following reaction formula 1. The substituents may be combined by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.
[ reaction formula 1]
Figure BDA0002614846360000202
In the above reaction formula 1, L1, L2, Ar1, R2 and n are defined as in chemical formula 1, and R1 defined in chemical formula 1 may be substituted in the pyridine ring of the benzothienopyridine ring of the above reaction formula.
In addition, the present specification provides an organic light emitting device comprising the above-mentioned compound.
In an embodiment of the present application, there is provided an organic light emitting device including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound of chemical formula 1.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
The organic layer of the organic light-emitting device of the present application may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device 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 layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
In one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer is a green light emitting layer.
In one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host.
In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound and further includes a dopant.
In one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound and further includes an iridium-based dopant.
In one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound and further includes an iridium-based dopant.
In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the compound and a dopant in a weight ratio of 1:100 to 100: 1.
In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the compound and a dopant at a weight ratio of 100:1 to 2: 1. In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the compound and a dopant at a weight ratio of 100: 15.
In one embodiment of the present application, the light-emitting layer includes 2 types of hosts.
In one embodiment of the present application, the light emitting layer further includes chemical formula 1 and another host.
In one embodiment of the present application, the light emitting layer includes the compound of formula 1 and further includes another host.
In one embodiment of the present application, the light emitting layer includes the compound of chemical formula 1 and other host in a weight ratio of 10:1 to 1: 10.
In one embodiment of the present application, the light emitting layer includes the compound of chemical formula 1 and another host at a weight ratio of 4: 6.
In one embodiment of the present application, the light-emitting layer further includes chemical formula 1 and another host, and the another host is a carbazole-based compound.
In one embodiment of the present application, the light-emitting layer further includes chemical formula 1 and another host, and the another host is a biscarbazole compound.
In one embodiment of the present application, the light emitting layer further includes chemical formula 1 and another host.
In one embodiment of the present application, the light-emitting layer further includes a compound of formula a as a host.
[ chemical formula A ]
Figure BDA0002614846360000231
In the above chemical formula a, Ar20 and Ar21, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group.
In one embodiment of the present application, Ar20 and Ar21 are the same as or different from each other, and each independently represents an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present application, Ar20 and Ar21 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, or a naphthyl group.
In one embodiment of the present application, the light emitting layer includes the compound of chemical formula 1 and the compound of chemical formula a in a weight ratio of 10:1 to 1: 10.
In one embodiment of the present application, the light emitting layer includes the compound of chemical formula 1 and the compound of chemical formula a in a weight ratio of 4: 6.
In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer.
In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, and an electron blocking layer.
In one embodiment of the present application, the organic layer includes a hole blocking layer, an electron transport layer, or an electron injection layer.
In one embodiment of the present application, the organic layer includes a hole blocking layer, an electron transport layer, and an electron injection layer.
In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.
In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
In one embodiment of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
In one embodiment of the present invention, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
In one embodiment of the present application, the organic light emitting device includes: a first electrode; a second electrode provided to face the first electrode; and a light-emitting layer provided between the first electrode and the second electrode; the organic light emitting device includes 2 or more organic layers between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least one of the 2 or more organic layers contains the compound.
In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
For example, fig. 1 shows an example of the structure of an organic light emitting device according to an embodiment of the present application.
Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the above compound may be contained in the above light-emitting layer 3.
Fig. 2 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4 are stacked in this order.
The organic light emitting device of the present application may be manufactured using materials and methods known in the art, except that one or more of the organic layers include the compound of the present application, i.e., the compound of chemical formula 1 described above.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device of the present application may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound of chemical formula 1 may be used not only for forming an organic layer by a vacuum evaporation method but also for forming an organic layer by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.
In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material 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); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
In one embodiment of the invention, the cathode comprises magnesium and silver.
In one embodiment of the invention, the cathode comprises magnesium and silver in a weight ratio of 10:1 to 1: 10.
In one embodiment of the invention, the cathode comprises magnesium and silver in a weight ratio of 1: 4.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
In one embodiment of the present invention, the hole injection layer contains 2 kinds of hole injection substances.
In one embodiment of the present invention, the hole injection layer includes a carbazole-amine-based compound.
In one embodiment of the present invention, the hole injection layer includes a carbazole-amine-based compound and a dopant.
In one embodiment of the present invention, the hole injection layer includes a carbazole-amine-based compound and a dopant in a weight ratio of 100:1 to 1: 1.
In one embodiment of the present invention, the hole injection layer includes a carbazole-amine-based compound and a dopant in a weight ratio of 100: 5.
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 substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
In one embodiment of the present invention, the hole injection layer includes a carbazole-amine-based compound.
In one embodiment of the present invention, the carbazole-amine compound of the hole injection layer and the hole transport layer is the same.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Figure BDA0002614846360000261
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder-type furan compound
Figure BDA0002614846360000271
Figure BDA0002614846360000272
Pyrimidine derivatives, etc., but are not limited thereto.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons well from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer can be as followsAs used in the art, with any desired cathode material. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
In one embodiment of the present invention, the electron transport layer may include lithium quinolate.
In one embodiment of the present invention, the electron transport layer contains 2 electron transport materials.
In one embodiment of the present invention, the electron transport layer contains 2 electron transport materials in a weight ratio of 2: 1.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Figure BDA0002614846360000273
Azole,
Figure BDA0002614846360000274
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-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), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
In one embodiment of the present invention, the electron injection layer includes lithium quinolate.
In one embodiment of the present invention, the electron injection layer contains magnesium.
In one embodiment of the present invention, the electron injection layer includes lithium quinolinate and magnesium.
In one embodiment of the present invention, the electron injection layer includes lithium quinolinate and magnesium in a weight ratio of 10:1 to 1: 10.
In one embodiment of the present invention, the electron injection layer comprises lithium quinolinate and magnesium in a weight ratio of 1: 1.
The hole-blocking layer is a layer that blocks holes from reaching the cathode, and can be formed under the same conditions as the hole-injecting layer. Specifically, there are
Figure BDA0002614846360000281
An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.
In one embodiment of the present invention, the hole blocking layer includes a carbazole-based compound.
In one embodiment of the present invention, the electron blocking layer includes an amine-based compound.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
The manufacture of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are provided to illustrate the present specification, and the scope of the present specification is not limited thereto.
Synthesis example 1]Synthesis of Compound 1
1) Synthesis of Compound 1-1
Figure BDA0002614846360000282
In a three-neck flask, the mixture is put into a vacuum flask,intermediate M (15.9g, 53.3mmol) and intermediate A (14.3g, 58.6mmol) were dissolved in 300ml of toluene, and NaOtBu (sodium tert-butoxide ) (7.7g, 79.9mmol) and Pd (PtBu) were added3)2After stirring (bis (tri-tert-butylphosphine) palladium, bis (tri-tert-butylphosphine) palladium (0)) (0.3g, 0.5mmol) under reflux for 6 hours under argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added, and the reaction mixture was transferred to a separatory funnel for extraction. The extract was washed with MgSO4The reaction mixture was dried and concentrated, and the sample was purified by silica gel column chromatography to obtain 15.5g of compound 1-1 (yield 60%). As a result of mass spectrometry of the obtained solid, a peak at M/Z461 was confirmed.
1) Synthesis of Compound 1
Figure BDA0002614846360000291
In a three-necked flask, compound 1-1(15.6g, 33.8mmol) and intermediate a (14.6g, 40.5mmol) were dissolved in 300ml of Tetrahydrofuran (THF), and K was added2CO3(18.7g, 135.2mmol) was dissolved in 150ml of water and added. To which Pd (PPh) was added3)4(2.0g, 1.7mmol) was stirred under reflux for 8 hours under an argon atmosphere. After cooling to normal temperature at the end of the reaction, the reaction solution was transferred to a separatory funnel and CH was used2Cl2Extraction is carried out. The extract was washed with MgSO4After drying, filtration and concentration, the sample was purified by silica gel column chromatography and then purified by sublimation, whereby 7.5g of compound 1 was obtained (yield: 34%). As a result of mass spectrometry of the obtained solid, a peak at M/Z658 was confirmed.
Synthesis example 2]Synthesis of Compound 2
Figure BDA0002614846360000292
Compound 2 was produced by the same production method as that of compound 1 except that intermediate a was used instead of intermediate b in synthetic example 1. As a result of mass spectrometry of the obtained solid, a peak at M/Z748 was confirmed.
[ Synthesis example 3]Synthesis of Compound 3
Figure BDA0002614846360000293
Compound 3 was produced by the same production method as that of compound 1, except that intermediate a was used instead of intermediate c in synthetic example 1. As a result of mass spectrometry of the obtained solid, a peak at M/Z734 was confirmed.
[ Synthesis example 4]Synthesis of Compound 4
Figure BDA0002614846360000301
Compound 4 was produced by the same production method as that of compound 1, except that intermediate a was used instead of intermediate B in synthetic example 1. The peak at M/Z700 was confirmed.
Synthesis example 5]Synthesis of Compound 5
Figure BDA0002614846360000302
Compound 5 was produced by the same production method as that of compound 1 except that in synthetic example 1, intermediate a was used instead of intermediate C and intermediate a was used instead of intermediate d. The peak at M/Z671 was confirmed.
[ Synthesis example 6]Synthesis of Compound 6
Figure BDA0002614846360000303
Compound 6 was produced by the same production method as that of compound 1, except that intermediate a was used instead of intermediate C in synthetic example 1. The peak at M/Z582 was confirmed.
[ Experimental example ]
Experimental example 1
ITO (indium tin Oxide) is added
Figure BDA0002614846360000304
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, as a hole injection layer, HT-A and 5 parts by weight (based on 100 parts by weight of HT-A) of PD were added
Figure BDA0002614846360000311
Is thermally vacuum evaporated, and then only the HT-A substance is evaporated
Figure BDA0002614846360000312
The hole transport layer is formed by evaporation. On the hole transport layer, as an electron blocking layer, the following HT-B and
Figure BDA0002614846360000313
thermal vacuum evaporation is performed on the thickness.
Next, as a light-emitting layer, compound 1 (host) and 15 parts by weight (based on 100 parts by weight of the host) of GD (dopant) were added
Figure BDA0002614846360000314
Vacuum evaporation is performed to a thickness of (1). N mutext, as a hole-blocking layer, the following ET-A and
Figure BDA0002614846360000315
vacuum evaporation is performed to a thickness of (1). Next, as an electron transporting layer, ET-B and LiQ were added at a ratio of 2:1
Figure BDA0002614846360000316
Is subjected to thermal vacuum deposition, and then LiF and magnesium are formed in a ratio of 1:1 as an electron injection layer
Figure BDA0002614846360000317
Vacuum evaporation is performed to a thickness of (1). On the electron injection layer, magnesium and silver are mixed at a ratio of 1:4
Figure BDA0002614846360000318
The cathode is formed by vapor deposition to produce an organic light-emitting device.
Figure BDA0002614846360000321
< Experimental examples 2 to 8 and comparative examples 1 to 8>
Organic light-emitting devices of experimental examples 2 to 8 and comparative examples 1 to 8 were produced by the same method as in experimental example 1, except that the host material was changed as shown in table 1 below. In this case, when a mixture of 2 compounds is used as a host, the parenthesis indicates the weight ratio between the host compounds.
Figure BDA0002614846360000331
The organic light-emitting devices produced in the above experimental examples 1 to 8 and comparative examples 1 to 8 were applied with current, and the voltage, efficiency, and lifetime (T95) were measured, and the results thereof are shown in the following table 1. In this case, the voltage and efficiency were 10mA/cm2T95 means at a current density of 20mA/cm2Next, the time required for the initial luminance to decrease to 95%.
[ Table 1]
Figure BDA0002614846360000341
In the compound represented by the above chemical formula 1, a nitrogen-containing heterocyclic ring functioning as an electron acceptor in a benzene ring such as benzothienopyridine is located at the 6-position of benzothienopyridine, and a carbazole-based substituent such as carbazole, indenocarbazole functioning as an electron donor is substituted at the meta-position of the nitrogen-containing heterocyclic ring. The electron donor unit and the electron acceptor unit are advantageous for both hole and electron transport by being present in the same molecule at the same time, and therefore have a structure suitable for use as a host substance of the light-emitting layer, as shown in table 1.
In particular, the two units are located at meta positions relative to each other based on benzothienopyridine, and thus, compared with dibenzothiophene (GH-C, GH-D, GH-E, GH-F), they are advantageous in electron transport and therefore have high efficiency. Further, GH-A, GH-B, which is an unsubstituted N-containing heteroaryl group or an N-containing heteroaryl group having 3 or more rings, which is a substituent that functions as an electron acceptor corresponding to Ar1 of the present invention, has a high efficiency and a long life because bipolar (Ambipolar) characteristics are exhibited with the Highest Occupied Molecular Orbital (HOMO) and the lowest occupied molecular orbital (LUMO) distributed appropriately.
In addition, in the above-mentioned experimental examples 7 and 8, the biscarbazole compound was mixed and used in the experimental examples 1 and 6. Experimental examples 7 and 8 showed more excellent effects in terms of voltage, efficiency and life as compared to experimental examples 1 and 6. However, in comparative examples 7 and 8, the biscarbazole compound was used in combination with comparative examples 1 and 4, and it was found that the lifetime was shortened.
Therefore, when the compound of chemical formula 1 of the present invention is mixed with a biscarbazole-based compound and used in a light-emitting layer, it is found that the compound has excellent effects in terms of voltage, efficiency, and lifetime of an organic light-emitting device.

Claims (11)

1. A compound represented by the following chemical formula 1:
chemical formula 1
Figure FDA0002614846350000011
In the chemical formula 1, the first and second organic solvents,
ar1 is a monocyclic or bicyclic N-containing heteroaryl group substituted with at least one substituent selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group,
l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
m is an integer of 0 to 3, and when m is 2 or more, R1 may be the same or different from each other,
r1 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
n is an integer of 0 to 8, and when n is 2 or more, R2 may be the same or different from each other,
r2 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or 2 or more R2 may be combined with each other to form a substituted or unsubstituted ring.
2. The compound of claim 1, wherein said L1 is a direct bond or an arylene group.
3. The compound of claim 1, wherein said L2 is a direct bond.
4. The compound of claim 1, wherein Ar1 is triazinyl substituted with at least one substituent selected from substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; a pyridyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; a pyrimidinyl group substituted with at least one substituent selected from a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; a quinolyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group; a quinazolinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; or a quinoxalinyl group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.
5. The compound of claim 1, wherein Ar1 is represented by the following formula a-1 or a-2:
chemical formula A-1
Figure FDA0002614846350000021
Chemical formula A-2
Figure FDA0002614846350000022
In the chemical formulas A-1 and A-2,
at least one of X1 to X3 is N, and the remainder are CH,
at least one of X4 and X5 is N, and the remainder are CH,
ar2 to Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Figure FDA0002614846350000031
refers to a position bound to L1 of said chemical formula 1.
6. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4:
chemical formula 1-1
Figure FDA0002614846350000032
Chemical formula 1-2
Figure FDA0002614846350000033
Chemical formulas 1 to 3
Figure FDA0002614846350000034
Chemical formulas 1 to 4
Figure FDA0002614846350000041
In the chemical formulas 1-1 to 1-4,
l1, L2, and Ar1 are the same as defined in said chemical formula 1,
ar10 and Ar11, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
x10 is CRR' or NR ",
r, R', and R "are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
7. The compound of claim 1, wherein the compound of formula 1 is selected from compounds represented by the following structural formulae:
Figure FDA0002614846350000042
Figure FDA0002614846350000051
Figure FDA0002614846350000061
Figure FDA0002614846350000071
Figure FDA0002614846350000081
Figure FDA0002614846350000091
Figure FDA0002614846350000101
8. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers contains the compound according to any one of claims 1 to 7.
9. The organic light emitting device of claim 8, wherein the organic layer comprises a light emitting layer comprising the compound.
10. The organic light emitting device according to claim 8, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.
11. The organic light emitting device according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011084531A (en) * 2009-10-19 2011-04-28 Konica Minolta Holdings Inc Material for organic electroluminescent element, organic electroluminescent element, illumination device and display device
US20120256169A1 (en) * 2011-04-08 2012-10-11 Universal Display Corporation Substituted oligoazacarbazoles for light emitting diodes
US20160336517A1 (en) * 2015-05-12 2016-11-17 Semiconductor Energy Laboratory Co., Ltd. Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
CN106432211A (en) * 2015-08-13 2017-02-22 三星电子株式会社 Condensed cyclic compound and organic light-emitting device including the same
CN106518893A (en) * 2015-09-09 2017-03-22 三星电子株式会社 Condensed cyclic comopund and organic light-emitting device including the same
CN107253954A (en) * 2017-06-05 2017-10-17 上海道亦化工科技有限公司 Compound and its organic electroluminescence device containing pyridine groups
WO2018025554A1 (en) * 2016-08-02 2018-02-08 コニカミノルタ株式会社 Nitrogen-containing heterocyclic compound production method

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (en) 2001-07-20 2005-02-24 Novaled Gmbh Light-emitting component with organic layers
DE602006011734D1 (en) * 2005-05-30 2010-03-04 Basf Se ELECTROLUMINESCENT DEVICE
JP5589251B2 (en) * 2006-09-21 2014-09-17 コニカミノルタ株式会社 Organic electroluminescence element material
US9067947B2 (en) * 2009-01-16 2015-06-30 Universal Display Corporation Organic electroluminescent materials and devices
KR102308117B1 (en) * 2014-10-17 2021-10-01 삼성전자주식회사 Carbazole-based compound and organic light emitting device including the same
KR102308116B1 (en) * 2014-10-23 2021-10-05 삼성전자주식회사 Condensed cyclic compound and organic light emitting device including the same
KR102162607B1 (en) * 2018-06-07 2020-10-07 주식회사 엘지화학 Compound and organic light emitting device comprising the same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011084531A (en) * 2009-10-19 2011-04-28 Konica Minolta Holdings Inc Material for organic electroluminescent element, organic electroluminescent element, illumination device and display device
US20120256169A1 (en) * 2011-04-08 2012-10-11 Universal Display Corporation Substituted oligoazacarbazoles for light emitting diodes
US20160336517A1 (en) * 2015-05-12 2016-11-17 Semiconductor Energy Laboratory Co., Ltd. Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
CN106432211A (en) * 2015-08-13 2017-02-22 三星电子株式会社 Condensed cyclic compound and organic light-emitting device including the same
CN106518893A (en) * 2015-09-09 2017-03-22 三星电子株式会社 Condensed cyclic comopund and organic light-emitting device including the same
WO2018025554A1 (en) * 2016-08-02 2018-02-08 コニカミノルタ株式会社 Nitrogen-containing heterocyclic compound production method
CN107253954A (en) * 2017-06-05 2017-10-17 上海道亦化工科技有限公司 Compound and its organic electroluminescence device containing pyridine groups

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
王芳芳等: "高效蓝光有机电致磷光主体材料的研究进展", 《化学学报》 *

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