CN111683952B

CN111683952B - Compound and organic light emitting device including the same

Info

Publication number: CN111683952B
Application number: CN201980011452.0A
Authority: CN
Inventors: 洪玩杓; 金振珠; 尹洪植; 金善珉
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-06-07
Filing date: 2019-06-07
Publication date: 2023-04-07
Anticipated expiration: 2039-06-07
Also published as: WO2019235875A1; CN111683952A; KR20190139159A; KR102162609B1

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 present specification claims priority to korean patent application No. 10-2018-0065356 filed on 7.6.2018 to 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, life span, or efficiency of the organic light emitting device, 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]

In the above-mentioned chemical formula 1,

ar1 is a monocyclic or bicyclic N-containing heteroaryl group substituted with at least one substituent of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group,

l1 and L2, which may be the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

m is an integer of 0 to 3, and when m is 2 or more, R1 s are 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 s are 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, 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 one or more of the organic layers contain 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 substituents in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are bonded" 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, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically, it includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

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,

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,

Based on the combination of an azole radical and a sugar radical>

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazino-pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobamboo>

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothienyl, dibenzothienyl, o benzofuranyl, dibenzofuranyl, benzothiollyl, dibenzothiaollyl, phenanthrolinyl, or iso/pyridyl>

Azolyl, thiadiazolyl, thiophenylThiazinyl, thiophen->

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 specificationWherein L1 is a direct bond,

In one embodiment of the present specification, L2 is a direct bond.

In one embodiment of the present specification, ar1 is 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 the group consisting of 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 is 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 is 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 group selected from an aryl group and a heteroaryl group, which is 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]

[ chemical formula A-2]

In the above chemical formulas A-1 and A-2,

at least one of X1 to X3 is N, and the others are CH,

at least one of X4 and X5 is N, and the others 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,

refers to a position bound to L1 of the above chemical formula 1.

In one embodiment of the present disclosure, X1 to X3 are N.

In one embodiment of the present disclosure, at least 2 of X1 to X3 are N, and the remainder are CH.

In one embodiment of the present specification, X1 and X2 are N, and X3 is CH.

In one embodiment of the present specification, X1 and X3 are N, and X2 is CH.

In one embodiment of the present specification, 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 specification, X1 is N, and X2 and X3 are CH.

In one embodiment of the present specification, X2 is N, and X1 and X3 are CH.

In one embodiment of the present specification, 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 phenyl.

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]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

In the above chemical formulas 1-1 to 1-4,

l1, L2, and Ar1 are 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 is 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 are the same as or different from each other, and each independently represents 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 are the same as or different from each other, and each independently represents 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' are the same or different and each independently methyl, ethyl, propyl, or butyl.

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.

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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 to form 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. is carried out by the production method shown in the following reaction formula 1.

For example, the compound of the above chemical formula 1 may have 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]

In the above reaction formula 1, 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 invention, 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 at a weight ratio of 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. 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.

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 another host at a weight ratio of 10.

In one embodiment of the present application, the light emitting layer includes the compound of chemical formula 1 and other host at a weight ratio of 4.

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 a compound of formula a as a host.

[ chemical formula A ]

In the above chemical formula a, ar20 and Ar21 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

In one embodiment of the present application, ar20 and Ar21 are the same or different from each other and each independently 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.

In one embodiment of the present application, the light emitting layer includes the compound of formula 1 and the compound of formula a in a weight ratio of 4.

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 invention, 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.

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 material 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 SnO ₂ A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene) 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 LiO ₂ And multi-layer structured materials 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.

In one embodiment of the invention, the cathode comprises magnesium and silver in a weight ratio of 1.

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 species is between the work function of the anode species 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 contains the carbazole-amine-based compound and the dopant in a weight ratio of 100.

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 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

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 fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include dibenzofuran derivatives and ladder furan compounds

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 Alq ₃ The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. 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 layer or a silver layer.

In one embodiment of the present invention, the electron transport layer may include lithium quinolinate.

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.

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, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole and/or liquor>

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, but are not limited to, 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) gallium, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, and gallium bis (2-methyl-8-quinolinolato) (2-naphthol) gallium.

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 includes magnesium.

In one embodiment of the present invention, the electron injection layer comprises lithium quinoline and magnesium.

In one embodiment of the present invention, the electron injection layer comprises lithium quinolinate and magnesium in a weight ratio of 10 to 1.

In one embodiment of the present invention, the electron injection layer comprises lithium quinolinate and magnesium in a weight ratio of 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

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

In a three-necked 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 added ₃ ) ₂ (bis (tri-tert-butylphosphine) palladium, bis (tri-tert-butylphosphine) palladium (0)) (0.3 g,0.5 mmol) under argon refluxAnd stirred for 6 hours. 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 MgSO ₄ The 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/Z =461 was confirmed.

1) Synthesis of Compound 1

In a three-necked flask, compound 1-1 (15.6 g,33.8 mmol) and intermediate a (14.6 g,40.5 mmol) were dissolved in 300ml of Tetrahydrofuran (THF), and K was added ₂ CO ₃ (18.7 g, 135.2mmol) was dissolved in 150ml of water and added. To which Pd (PPh) was added ₃ ) ₄ (2.0g, 1.7mmol) under reflux in an argon atmosphere, and stirred for 8 hours. After cooling to normal temperature at the end of the reaction, the reaction solution was transferred to a separatory funnel and CH was used ₂ Cl ₂ Extraction is carried out. The extract was washed with MgSO ₄ After 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/Z =658 was confirmed.

Synthesis example 2]Synthesis of Compound 2

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/Z =748 was confirmed.

[ Synthesis example 3]Synthesis of Compound 3

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/Z =734 was confirmed.

[ Synthesis example 4]Synthesis of Compound 4

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/Z =700 was confirmed.

Synthesis example 5]Synthesis of Compound 5

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. A peak at M/Z =671 was confirmed.

[ Synthesis example 6]Synthesis of Compound 6

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/Z =582 was confirmed.

[ Experimental example ]

Experimental example 1

ITO (indium tin Oxide) is added

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 was prepared by Fischer co, and the distilled water was filtered twice by 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

Is subjected to thermal vacuum evaporation, and then only HT-A substances are combined in a manner such that->

The hole transport layer is formed by vapor deposition. On the hole transport layer, as an electron blocking layer, the following HT-B and

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

Vacuum evaporation is performed to a thickness of (1). Next, as a hole blocking layer, the following ET-A is substituted with ^ H>

Vacuum evaporation is performed to a thickness of (1). Next, as an electron transport layer, the following ET-B and LiQ are present in a ratio of 2>

Is subjected to thermal vacuum deposition, and then LiF and magnesium are used as an electron injection layer in a ratio of 1>

Vacuum evaporation is performed to a thickness of (1). On the electron injection layer, magnesium and silver are dissolved in a ratio of 1>

The thickness of (2) was evaporated to form a cathode, thereby manufacturing an organic light-emitting device. />

< 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 in the same manner 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.

The organic light emitting devices fabricated in the above experimental examples 1 to 8 and comparative examples 1 to 8 were applied with current, and voltage, efficiency, and lifetime (T95) were measured, and the results thereof are shown in table 1 below. In this case, the voltage and efficiency were 10mA/cm ² T95 is measured at a current density of 20mA/cm ² Next, the time required for the initial brightness to decrease to 95%.

[ Table 1]

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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, since the two units are located at meta positions with respect to the benzothienopyridine, they are more advantageous in electron transfer than dibenzothiophenes (GH-C, GH-D, GH-E, and GH-F), and therefore have high efficiency. Further, GH-a and GH-B are superior to the unsubstituted N-containing heteroaryl group serving as an electron acceptor corresponding to the substituent of Ar1 of the present invention, or the N-containing heteroaryl group having 3 or more rings, because the Highest Occupied Molecular Orbital (HOMO) and the lowest occupied molecular orbital (LUMO) are appropriately distributed and bipolar (Ambipolar) characteristics are well exhibited, efficiency and lifetime are high.

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

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

ar1 is a triazinyl group or a quinazolinyl group substituted with at least one substituent of a monocyclic aryl group having 6 to 30 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms,

l1 and L2 are directly bonded,

r1 is hydrogen or deuterium,

r2 is hydrogen, deuterium, or a monocyclic aryl group having 6 to 30 carbon atoms, or 2 or more R2 s are bonded to each other to form a hydrocarbon ring which is substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms.

2. The compound of claim 1, wherein Ar1 is represented by the following formula a-1 or a-2:

chemical formula A-1

Chemical formula A-2

In the chemical formulas A-1 and A-2,

x1 to X3 are N,

x4 and X5 are N,

ar2 to Ar4 are the same as or different from each other, and each independently is a monocyclic aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms,

refers to a position bound to L1 of the chemical formula 1.

3. 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

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

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 monocyclic aryl group having 6 to 30 carbon atoms,

x10 is CRR',

r and R' are the same or different from each other and each independently an alkyl group having 1 to 50 carbon atoms.

4. The compound of claim 1, wherein the compound of formula 1 is selected from compounds represented by the following structural formulae:

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5. 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 4, and wherein the organic layer includes a light-emitting layer containing the compound.

6. The organic light emitting device according to claim 5, 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.

7. The organic light-emitting device according to claim 5, 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.