CN111770919B - 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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CN111770919B
CN111770919B CN201980013731.0A CN201980013731A CN111770919B CN 111770919 B CN111770919 B CN 111770919B CN 201980013731 A CN201980013731 A CN 201980013731A CN 111770919 B CN111770919 B CN 111770919B
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CN111770919A (en
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金振珠
洪玩杓
尹洪植
李东勋
车龙范
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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 present application claims priority to korean patent application No. 10-2018-0068172, which was filed on korean patent office on the day of 2018, month 6 and day 14, and 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. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the 2 electrodes are combined in the organic thin film to be paired, 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]
Figure GDA0002635450700000021
In the above-mentioned chemical formula 1,
l1 and L2, equal to or different from each other, are each independently a direct bond or an arylene group,
one of Ar1 and Ar2 is a substituted or unsubstituted indolyl group, a substituted or unsubstituted N-containing tricyclic or higher heterocyclic group, a substituted or unsubstituted silyl group, or an aryl group substituted with a silyl group,
the other of Ar1 and Ar2 is a substituted or unsubstituted N-containing monocyclic heterocyclic group, a substituted or unsubstituted bicyclic heterocyclic group formed of an N-containing six-membered ring, or a substituted or unsubstituted O or S-containing heterocyclic group.
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 to face the first electrode, and one 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.
When the substituents are bonded to the 1 and 4 positions of triphenylene, since the triphenylene having a planar structure has a symmetrical structure on both sides, the solubility is poor, and the sublimation temperature tends to be high, which causes a problem of lowering the thermal stability in depositing a device. Therefore, when the compound according to the present invention has substituents bonded to the 1 and 3 positions of triphenylene, it has an asymmetric structure, and thus provides a steric hindrance (steric) effect, thereby increasing solubility, lowering sublimation temperature, and improving thermal stability in a deposition device.
When Ar1 and Ar2 of the present invention are each introduced into triphenylene as an Electron Donating Group (EDG) and an Electron Withdrawing Group (EWG), there is an advantage that the migration of electrons and holes can be regulated within one molecule, and an increase in efficiency and lifetime of a device can be expected by utilizing the characteristics of such a bipolar compound.
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, a light-emitting layer 3, a hole blocking layer 7, an electron transport layer 8, 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: hole blocking layer
8: electron transport 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.
Since the compound of the present invention has substituents bonded to the 1-and 3-positions of triphenylene, the solubility can be improved and the sublimation temperature can be lowered by steric hindrance (steric) effect as compared with the compound bonded to the 1-and 4-positions. Further, since more substituents are introduced when the substituents are present at the 1-and 3-positions simultaneously, the energy level can be easily adjusted, as compared with the case where the substituents are present only at the 1-or 3-positions.
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, 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, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-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, there may be mentioned methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutoxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group and the like, but 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 GDA0002635450700000051
And a fluorenyl group, but is not limited thereto.
In the present specification, the heterocyclic group contains one or more atoms other than carbon, i.e., heteroatoms, and specifically, the above-mentioned heteroatoms may contain one or more atoms selected from O, N, se, si, S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but it is preferable that the number of carbon atoms is 2 to 60 or 2 to 30. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure GDA0002635450700000052
Based on the combination of an azole radical and a sugar radical>
Figure GDA0002635450700000053
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazino-pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobamboo>
Figure GDA0002635450700000054
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiapyrrolyl, phenanthrolinyl group, isovale>
Figure GDA0002635450700000055
Azolyl, thiadiazolyl, phenothiazinyl, phenoxazine>
Figure GDA0002635450700000056
Oxazine groups, and their fused structures, and the like, but are not limited thereto. />
In the present specification, the N-containing heterocyclic group means a heterocyclic group containing N as a heteroatom, and may further contain a heteroatom other than N, such as O or S.
In the present specification, an O-or S-containing heterocyclic group means a heterocyclic group containing O or S as a heteroatom, and may further contain a heteroatom such as N other than O or S.
In the present specification, arylene refers to 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 one embodiment of the present specification, L1 and L2 are directly bonded to each other.
In one embodiment of the present specification, one of Ar1 and Ar2 is a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted indolinocarbazolyl group, a substituted or unsubstituted indolopyridyl group, a substituted or unsubstituted benzofurocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, a substituted or unsubstituted indolinoindolyl group, a substituted or unsubstituted indanocarbazolyl group, a substituted or unsubstituted hexahydropyridoquinolinyl group, a substituted or unsubstituted triphenylsilyl group, a phenyl group substituted with a trimethylsilyl group, or a substituted or unsubstituted tetraphenylsilyl group.
In one embodiment of the present specification, one of Ar1 and Ar2 is selected from the following structural formulae.
Figure GDA0002635450700000061
In the above structural formula, at least one of X20 to X23 is N, the others are CH, Y is S, O or CRR',
r, R ', R4 and R4' are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, m is an integer of 1 to 8, n is an integer of 1 to 10,
when m and n are 2 or more, R4 in the parentheses may be the same or different from each other.
In one embodiment of the present specification, R4 and R4' are the same as or different from each other, and each independently represents hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R4 and R4' are the same as or different from each other and each independently represents hydrogen, deuterium, a nitrile group, a substituted or unsubstituted methyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and the "substituted or unsubstituted" means that the substituent is substituted or unsubstituted with 1 or more substituents selected from the group consisting of a nitrile group, a butyl group, a phenyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
In one embodiment of the local specification, one of Ar1 and Ar2 is selected from the following structural formulae.
Figure GDA0002635450700000071
In the above-mentioned structural formula, the polymer,
at least one of X1 to X3 is N, and the others are CR1,
x4 to X7 are each independently N or CR2,
at least one of X8 to X14 is N, and the remainder are CR3,
y1 and Y2, R1 to R3, and R5, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group,
z1 to Z5, which may be the same or different from each other, are each independently O or S.
In one embodiment of the present specification, all of X1 to X3 are N.
In one embodiment of the present specification, 2 of the X1 to X3 are N, and the rest are CR1.
In one embodiment of the present specification, X1 and X2 are N, and X3 is CR1.
In one embodiment of the present specification, X1 and X3 are N, and X2 is CR1.
In one embodiment of the present specification, X2 and X3 are N, and X1 is CR1.
In one embodiment of the present specification, one of X1 to X3 is N, and the others are CR1.
In one embodiment of the present specification, X1 is N, and X2 and X3 are CR1.
In one embodiment of the present specification, X2 is N, and X1 and X3 are CR1.
In one embodiment of the present specification, X3 is N, and X1 and X2 are CR1.
In one embodiment of the present specification, R1 is hydrogen.
In one embodiment of the present specification, X4 to X7 are CR2, and R2 is hydrogen or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, X4 to X7 are CR2, and R2 is hydrogen.
In one embodiment of the present disclosure, at least one of X4 to X7 is N, the remainder is CR2, and R2 is hydrogen.
In one embodiment of the present specification, at least one of the above X8 to X14 is N, the others are CR3, and R3 is hydrogen or a substituted or unsubstituted aryl group.
In one embodiment of the present disclosure, at least one of X8 to X14 is N, the others are CR3, and R3 is hydrogen, phenyl, or naphthyl.
In one embodiment of the present specification, one of the above X8 to X14 is N, the others are CR3, and R3 is hydrogen or a substituted or unsubstituted aryl group.
In one embodiment of the present disclosure, one of X8 to X14 is N, the others are CR3, and R3 is hydrogen, phenyl or naphthyl.
In one embodiment of the present specification, two of X8 to X14 are N, the remainder are CR3, and R3 is hydrogen or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, two of the above X8 to X14 are N, the rest are CR3, and R3 is hydrogen, phenyl or naphthyl.
In one embodiment of the present specification, three of the above X8 to X14 are N, the remainder are CR3, and R3 is hydrogen or a substituted or unsubstituted aryl group.
In one embodiment of the present disclosure, three of X8 to X14 are N, the rest are CR3, and R3 is hydrogen, phenyl or naphthyl.
In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently represents a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
In one embodiment of the present specification, Z1 is O.
In one embodiment of the present specification, Z1 is S.
In one embodiment of the present specification, Z2 is O.
In one embodiment of the present specification, Z2 is S.
In one embodiment of the present specification, Z3 is O.
In one embodiment of the present specification, Z3 is S.
In one embodiment of the present specification, Z4 is O.
In one embodiment of the present specification, Z4 is S.
In one embodiment of the present specification, Z5 is O.
In one embodiment of the present specification, Z5 is S.
In one embodiment of the present specification, ar1 is a substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolinocarbazolyl, substituted or unsubstituted indolopyridyl, substituted or unsubstituted benzofurocarbazolyl, substituted or unsubstituted benzothienocarbazolyl, substituted or unsubstituted indolinoindolyl, substituted or unsubstituted indanocarbazolyl, substituted or unsubstituted hexahydropyridoquinolinyl, substituted or unsubstituted triphenylsilyl, phenyl substituted with trimethylsilyl, or substituted or unsubstituted tetraphenylsilyl,
ar2 mentioned above is a substituted or unsubstituted N-containing monocyclic heterocyclic group, a substituted or unsubstituted bicyclic heterocyclic group formed of an N-containing six-membered ring, or a substituted or unsubstituted O-or S-containing heterocyclic group.
In one embodiment of the present specification, ar2 is a substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolinocarbazolyl, substituted or unsubstituted indolinocylindolyl, substituted or unsubstituted indanocarbazolyl, substituted or unsubstituted hexahydropyridoquinolinyl, substituted or unsubstituted triphenylsilyl, phenyl substituted with trimethylsilyl, or substituted or unsubstituted tetraphenylsilyl,
ar1 above is a substituted or unsubstituted N-containing monocyclic heterocyclic group, a substituted or unsubstituted bicyclic heterocyclic group formed of an N-containing six-membered ring, or a substituted or unsubstituted O or S-containing heterocyclic group.
In one embodiment of the present specification, "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, an alkyl group, an aryl group, and a heterocyclic group, or with 2 or more substituents among the above substituents.
In one embodiment of the present specification, "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, or with 2 or more substituents among the above substituents being linked.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is selected from the following structural formulas.
Figure GDA0002635450700000101
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Figure GDA0002635450700000111
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Figure GDA0002635450700000121
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Figure GDA0002635450700000131
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Figure GDA0002635450700000141
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Figure GDA0002635450700000151
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Figure GDA0002635450700000161
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Figure GDA0002635450700000171
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Figure GDA0002635450700000181
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Figure GDA0002635450700000191
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Figure GDA0002635450700000201
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Figure GDA0002635450700000211
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Figure GDA0002635450700000221
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Figure GDA0002635450700000231
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Figure GDA0002635450700000241
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Figure GDA0002635450700000251
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Figure GDA0002635450700000261
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Figure GDA0002635450700000271
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Figure GDA0002635450700000281
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Figure GDA0002635450700000291
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Figure GDA0002635450700000301
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Figure GDA0002635450700000311
The compound according to an embodiment of the present application can be produced by a production method described later.
For example, the compound of chemical formula 1 may have a nucleation structure as shown in the following reaction formula 1. The substituents may be bonded 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 GDA0002635450700000312
The production method of chemical formula 1 is as described above. A and B are halogen, and may be the same or different. In general, the synthesis can be performed by Suzuki (Suzuki) or Buchwald (Buchwald) reactions used in the art.
In the above reaction formula 1, L2, ar1 and Ar2 are the same as defined in chemical formula 1.
In one embodiment of the present application, the maximum light emission wavelength of the compound is 400 to 700nm.
In one embodiment of the present application, the maximum light emission wavelength of the compound is 500 to 540nm.
In one embodiment of the present application, the maximum light emission wavelength of the compound is 510 to 525nm.
In one embodiment of the present application, the maximum light emission wavelength of the compound is 515 to 520nm.
In addition, the present specification provides the above-mentioned 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 so as 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 contain the compound.
In this 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 is referred to as "including" or "including" a certain component, unless specifically stated to the contrary, it means that the part may further include other components, but does not exclude other components.
The organic layer of the organic light-emitting device of the present application may have a single-layer structure, or may have 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 invention, the organic layer includes a light emitting layer, the light emitting layer includes the compound, 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 specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include other organic compounds, metals, or metal compounds as a dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a main component, and may include an iridium-based dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include a phosphorescent dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include a red or green phosphorescent dopant.
In one embodiment of the present specification, the organic layer including the compound of chemical formula 1 includes the compound of chemical formula 1 as a host, and may include an iridium-based phosphorescent dopant.
According to one embodiment of the present specification, the light-emitting layer contains the compound and the dopant at a weight ratio of 1.
According to one embodiment of the present specification, the light-emitting layer includes the compound and a dopant in a weight ratio of 2:1 to 99.
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 the structure as described above, 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, a light-emitting layer 3, a hole blocking layer 7, an electron transport layer 8, 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 above-described compound.
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 Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (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 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 can 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 which can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, and the like, 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-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 LiO 2 And multi-layer structured materials such as Al, but not limited thereto.
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, metalloporphyrins (porphyrins), oligothiophenes, arylamine-based organic substances, hexanenitrile-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyanilines, and polythiophene-based conductive polymers.
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.
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 GDA0002635450700000351
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiro) 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 compound, a dibenzofuran derivative, a ladder-type furan compound
Figure GDA0002635450700000352
Figure GDA0002635450700000353
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 (2), the organic radical compound, the hydroxyflavoneMetal complexes, 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 or silver layer.
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, an effect of injecting electrons from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevention of transfer of excitons generated in the light-emitting layer to a hole-injecting layer, and an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Figure GDA0002635450700000361
Azole and/or liquor>
Figure GDA0002635450700000362
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-quinolinolate, zinc bis (8-quinolinolate), copper bis (8-quinolinolate), manganese bis (8-quinolinolate), aluminum tris (2-methyl-8-quinolinolate), gallium tris (8-quinolinolate), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolate) chloride, gallium bis (2-methyl-8-quinolinolate) (o-cresol), aluminum bis (2-methyl-8-quinolinolate) (1-naphthol), and gallium bis (2-methyl-8-quinolinolate) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as those of the hole injection layer. Specifically, there are
Figure GDA0002635450700000363
DiazolesDerivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes (aluminum complexes), and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bidirectional 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.
Production example
Synthesis of Compound 1
Figure GDA0002635450700000371
The above-mentioned compound 1-bromo-3-chlorotriene (10g, 29.41mmol) and 9H-carbazole (4.9g, 29.41mmol) were completely dissolved in 90ml of toluene, and then sodium tert-butoxide (3.4g, 35.29mmol) was added thereto, and the mixture was stirred at elevated temperature until reflux. At the start of reflux, 2mol% of bis (tri-tert-butylphosphine) palladium was added dropwise slowly. The reaction was terminated after 4 hours, the temperature was lowered to normal temperature, and after concentration under reduced pressure, column purification was performed to obtain 8.4g (yield 67%) of intermediate 1-1.
The above-mentioned intermediate 1-1 (8.4g, 19.67mmol), bis (pinacolato) diboron (6.5g, 25.57mmol), potassium acetate (3.9g, 39.34mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000372
In an alkane, stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column purification was performed to obtain 8.2g (yield 80%) of intermediate 1-2.
The above-mentioned intermediates 1-2 (8.2g, 15.74mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.2g, 29.41mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and mixed by dissolving potassium carbonate (6.5g, 47.22mmol) in 30ml of water. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 6.9g (yield 70%) of compound 1.
MS:[M+H] + ＝625
Synthesis of Compound 2
Figure GDA0002635450700000381
The above-mentioned compounds 1-bromo-3-chlorotriene (10g, 29.41mmol), (9- (phenyl-d 5) -9H-carbazol-3-yl) boronic acid (8.6 g, 29.41mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (12.2g, 88.23mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 10.2g (yield 68%) of intermediate 2-1.
The above intermediate 2-1 (10.2g, 20.07mmol), bis (pinacolato) diboron (6.6 g, 26.09mmol), potassium acetate (3.9g, 40.14mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000382
In an alkane, the mixture was stirred at 100 ℃ for 12 hours. After the reaction, the reaction mixture was cooled to room temperature, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad)The mixture was concentrated under reduced pressure. Column purification was performed to obtain 7.9g (yield 66%) of intermediate 2-2.
The above-mentioned intermediate 2-2 (7.9 g, 13.25mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.5 g, 13.25mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (5.5 g, 39.75mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 7.2g (yield 77%) of compound 2.
MS:[M+H] + ＝706
Synthesis of Compound 3
Figure GDA0002635450700000391
The above-mentioned compounds 1-bromo-3-chlorotriene (10g, 29.41mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (8.4g, 29.41mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphoshine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (12.2g, 88.23mmol) was dissolved in 30ml of water to mix. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 10.9g (yield 74%) of intermediate 3-1.
The above intermediate 3-1 (10.9g, 21.76mmol), bis (pinacolato) diboron (7.2g, 28.29mmol), potassium acetate (4.3g, 43.52mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000392
In an alkane, stirring for 12 hours at 100 DEG CThen (c) is performed. After completion of the reaction, the reaction mixture was cooled to room temperature, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column purification was performed to obtain 9.7g (yield 75%) of intermediate 3-2.
The above-mentioned intermediate 3-2 (9.7g, 16.32mmol), 2-chloro-4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1,3,5-triazine (5.8g, 16.32mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphoshine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (6.8g, 48.96mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 8.3g (yield: 64%) of compound 3.
MS:[M+H] + ＝791
Synthesis of Compound 4
Figure GDA0002635450700000401
The above-mentioned compound 1-bromo-3-chlorotriene (10g, 29.41mmol) and 2-phenyl-9H-carbazole (7.1g, 29.41mmol) were completely dissolved in 90ml of toluene, and then sodium t-butoxide (3.4g, 35.29mmol) was added thereto, followed by stirring at elevated temperatures until refluxing. At the beginning of reflux, 2mol% of bis (tri-tert-butylphosphine) palladium was added dropwise slowly. The reaction was terminated after 4 hours, and after the temperature was lowered to normal temperature and concentrated under reduced pressure, column purification was performed to obtain 10.9g (yield 74%) of intermediate 4-1.
The above intermediate 4-1 (10.9g, 21.76mmol), bis (pinacolato) diboron (7.2g, 28.29mmol), potassium acetate (4.3g, 43.52mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000402
In an alkane, stirring at 100 DEG CStirring for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), followed by concentration under reduced pressure. Column purification was performed to obtain 9.7g (yield 75%) of intermediate 4-2.
The above-mentioned intermediate 4-2 (9.7g, 16.25mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.3g, 16.25mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (6.7g, 48.75mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto, the mixture was stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure, and column purification was performed, whereby 7.8g (yield: 69%) of compound 4 was obtained.
MS:[M+H] + ＝701
Synthesis of Compound 5
Figure GDA0002635450700000411
/>
The above-mentioned compound 1-bromo-3-chlorotriene (10g, 29.41mmol) and 5H-benzo [ b ] carbazole (6.4 g, 29.41mmol) were completely dissolved in 90ml of toluene, and then sodium t-butoxide (3.4 g, 35.29mmol) was added thereto, followed by stirring at elevated temperatures until refluxing. At the start of reflux, 2mol% of bis (tri-tert-butylphosphine) palladium was added dropwise slowly. The reaction was terminated after 4 hours, the temperature was lowered to normal temperature, and after concentration under reduced pressure, column purification was performed to obtain 10.2g (yield 73%) of intermediate 5-1.
The above intermediate 5-1 (10.2g, 21.46mmol), bis (pinacolato) diboron (7.1g, 27.90mmol), potassium acetate (4.2g, 42.92mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000412
In an alkane, stirred at 100 ℃ for 12 hours.After completion of the reaction, the reaction mixture was cooled to room temperature, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column purification was performed to obtain 7.5g (yield 61%) of intermediate 5-2.
The above intermediate 5-2 (7.5g, 13.09mmol), 4-chloro-2,6-diphenylpyrimidine (3.5g, 13.09mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (5.4 g, 39.27mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to carry out column purification, thereby obtaining 6.5g (yield 74%) of compound 5.
MS:[M+H] + ＝674
Synthesis of Compound 6
Figure GDA0002635450700000421
The above-mentioned compounds 1-bromo-3-chlorotriene (10g, 29.41mmol), (9- (3,5-dicyanophenyl) -9H-carbazol-3-yl) boronic acid (9.9g, 29.41mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphospine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (12.2g, 88.23mmol) was dissolved in 30ml of water to be mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to carry out column purification, thereby obtaining 11.7g (yield: 72%) of intermediate 6-1.
The above intermediate 6-1 (11.7g, 21.17mmol), bis (pinacolato) diboron (7.0g, 27.53mmol), potassium acetate (4.1g, 42.34mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of Bis (cyclohexylideneacetone) palladium
Figure GDA0002635450700000422
In an alkane, stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column purification was performed to obtain 8.7g (yield 64%) of intermediate 6-2.
The above-mentioned intermediate 6-2 (8.7 g, 13.66mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.6 g, 13.55mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (5.6 g, 40.65mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 7.6g (yield: 75%) of compound 6.
MS:[M+H] + ＝751
Synthesis of Compound 7
Figure GDA0002635450700000431
The above-mentioned intermediate 3-2 (9.7 g, 16.32mmol) and 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d ] pyrimidine (4.8g, 16.32mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (6.7 g, 48.96mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 8.4g (yield 71%) of compound 7.
MS:[M+H] + ＝730
Synthesis of Compound 8
Figure GDA0002635450700000432
The above-mentioned compounds 3-bromo-1-chlorotriene (10g, 29.41mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (8.4g, 29.41mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphoshine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (12.2g, 88.23mmol) was dissolved in 30ml of water to mix. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 10.5g (yield 71%) of intermediate 8-1.
The above-mentioned intermediate 8-1 (10.5g, 20.88mmol), bis (pinacolato) diboron (6.9g, 27.15mmol), potassium acetate (4.1g, 41.76mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000441
In an alkane, stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column purification was performed to obtain 9.4g (yield 76%) of intermediate 8-2.
The above intermediate 8-2 (9.4 g, 15.87mmol), 2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine (5.9g, 15.87mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphin) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (6.6g, 47.61mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 8.3g (yield 67%) of compound 8.
MS:[M+H] + ＝777
Synthesis of Compound 9
Figure GDA0002635450700000451
The above-mentioned compounds 3-bromo-1-chlorotriene (10g, 29.41mmol) and 7,7-dimethyl-5,7-dihydroindeno [2,1-b ] carbazole (8.3g, 29.41mmol) were completely dissolved in 90ml of toluene, and then sodium t-butoxide (3.4g, 35.29mmol) was added thereto, and the mixture was stirred while warming until refluxing. At the beginning of reflux, 2mol% of bis (tri-tert-butylphosphine) palladium was added dropwise slowly. The reaction was terminated after 4 hours, and after the temperature was lowered to normal temperature and concentrated under reduced pressure, column purification was performed to obtain 9.3g (yield 58%) of intermediate 9-1.
The above intermediate 9-1 (9.3g, 17.05mmol), bis (pinacolato) diboron (5.6 g, 22.17mmol), potassium acetate (3.3g, 34.1 mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000452
In an alkane, stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column purification was performed to obtain 7.0g (yield 65%) of intermediate 9-2.
The above intermediate 9-2 (7.0g, 11.08mmol), 2-chloro-4,6-diphenylpyrimidine (2.9g, 11.08mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (4.6g, 33.24mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto, the mixture was stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure, and column purification was performed to obtain 4.9g (yield 60%) of compound 9.
MS:[M+H] + ＝740
Synthesis of Compound 10
Figure GDA0002635450700000461
The above-mentioned compound 3-bromo-1-chlorotriene (10g, 29.41mmol) and 3- (dibenzo [ b, d ] furan-4-yl) -9H-carbazole (9.8g, 29.41mmol) were completely dissolved in 90ml of toluene, and then sodium tert-butoxide (3.4g, 35.29mmol) was added thereto, and the mixture was stirred while heating until refluxing. At the start of reflux, 2mol% of bis (tri-tert-butylphosphine) palladium was added dropwise slowly. The reaction was terminated after 4 hours, the temperature was lowered to normal temperature, and after concentration under reduced pressure, column purification was performed to obtain 11.2g (yield: 64%) of intermediate 10-1.
The above intermediate 10-1 (11.2g, 18.82mmol), bis (pinacolato) diboron (6.2g, 24.47mmol), potassium acetate (3.7g, 37.64mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000462
In an alkane, stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), followed by concentration under reduced pressure. Column purification was performed to obtain 12.9g (yield 69%) of intermediate 10-2.
The above intermediate 10-2 (12.9g, 12.98mmol), 4-chloro-2,6-diphenylpyrimidine (3.4g, 12.98mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (5.4g, 38.94mmol) was dissolved in 30ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto, the mixture was stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure, and column purification was performed, whereby 6.9g (yield 68%) of compound 10 was obtained.
MS:[M+H] + ＝790
Synthesis of Compound 11
Figure GDA0002635450700000471
The above-mentioned compound 3-bromo-1-chlorotriene (10g, 29.41mmol) and 5-phenyl-5,8-indolino [2,3-c ] carbazole (9.8g, 29.41mmol) were completely dissolved in 90ml of toluene, and then sodium tert-butoxide (3.4g, 35.29mmol) was added thereto, and the mixture was stirred while warming until refluxing. At the start of reflux, 2mol% of bis (tri-tert-butylphosphine) palladium was added dropwise slowly. The reaction was terminated after 4 hours, and after the temperature was lowered to normal temperature and concentrated under reduced pressure, column purification was performed to obtain 9.9g (yield: 57%) of intermediate 11-1.
The above intermediate 11-1 (9.9g, 16.76mmol), bis (pinacolato) diboron (5.5g, 21.79mmol), potassium acetate (3.3g, 33.52mmol), 4mol% Bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) palladium) and 8mol% tricyclohexylphosphine were added to 80ml of dicyclohexylphosphine
Figure GDA0002635450700000472
In an alkane, the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred, and then filtered through a silica gel pad (silica pad), followed by concentration under reduced pressure. Column purification was performed to obtain 8.0g (yield 70%) of intermediate 11-2.
The above intermediate 11-2 (8.0g, 11.73mmol), 4-chloro-2,6-diphenylpyrimidine (3.1g, 11.73mmol) and 4mol% Tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) palladium) were added to 60ml of tetrahydrofuran, and potassium carbonate (4.9g, 35.19mmol) was dissolved in 30ml of water to mix. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto, the mixture was stirred, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure to perform column purification, thereby obtaining 5.6g (yield 61%) of compound 11.
MS:[M+H] + ＝789
< Experimental example 1>
An Indium Tin Oxide (ITO) film
Figure GDA0002635450700000473
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, or 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, ir (ppy) was added in an amount of m-MTDATA (60 nm)/TCTA (80 nm)/Host (Host) +10 wt% 3 (300nm)/BCP(10nm)/Alq 3 The sequence of (30 nm)/LiF (1 nm)/Al (200 nm) constitutes a light-emitting device.
m-MTDATA、TCTA、Ir(ppy) 3 And the structures of BCP are shown below, respectively.
Figure GDA0002635450700000481
< Experimental examples 1-1>
In the above experimental example 1, the above compound 1 was used as a Host (Host), and a light-emitting device was produced.
< Experimental examples 1 and 2>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 2 was used instead of the compound 1.
< Experimental examples 1 to 3>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that the compound 3 was used instead of the compound 1 in the experimental example 1-1.
< Experimental examples 1 to 4>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 4 was used instead of the compound 1.
< Experimental examples 1 to 5>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 5 was used instead of the compound 1.
< Experimental examples 1 to 6>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 6 was used instead of the compound 1.
< Experimental examples 1 to 7>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that the compound 7 was used instead of the compound 1 in the experimental example 1-1.
< Experimental examples 1 to 8>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 8 was used instead of the compound 1.
< Experimental examples 1 to 9>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 9 was used instead of the compound 1.
< Experimental examples 1 to 10>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 10 was used instead of the compound 1.
< Experimental examples 1 to 11>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 11 was used instead of the compound 1.
< comparative example 1-1>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that GH1 was used instead of compound 1 in experimental example 1-1.
Figure GDA0002635450700000501
< comparative examples 1 and 2>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that GH2 was used instead of compound 1 in experimental example 1-1.
Figure GDA0002635450700000502
< comparative examples 1 to 3>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that GH3 was used instead of compound 1 in experimental example 1-1.
Figure GDA0002635450700000503
When a current was applied to the organic light emitting devices fabricated using experimental examples 1-1 to 1-11 and comparative examples 1-1 to 1-3, the results of table 1 were obtained.
[ Table 1]
Figure GDA0002635450700000511
In table 1, the EL peak is the maximum emission wavelength (λ max), and the measurement method is as follows. Photoluminescence spectra in the solution state were measured by LS-55 of Perkin Elmer (Perkin Elmer) company, and the excitation (excitation) wavelength had an emission spectrum at 300nm of 400 to 700nm. As solvent, high performance liquid chromatography grade (HPLC grade) Tetrahydrofuran (THF) was used.
As a result of experiments, the green organic EL devices of experimental examples 1-1 to 1-11, in which the compounds represented by compounds 1 to 11 according to the present invention were used as host materials of the light emitting layer, showed excellent performance in terms of current efficiency and driving voltage, as compared to the green organic EL devices of comparative examples 1-1 to 1-3, in which the existing GH was used.
Comparative example 1-1 used carbazolyl group combined in triphenylene 2, 11 position compounds, comparative example 1-2 used tetraphenylsilyl group only in triphenylene 3 position compounds, comparative example 1-3 used phenyl group combined in the position of 1 and indoline carbazolyl group combined in the position of 4 compounds. From the above-mentioned experimental examples 1-1 to 1-11, it was confirmed that the compounds of the present invention, each of which is an Electron Donating Group (EDG) and an Electron Withdrawing Group (EWG) at the position No. 1 or No. 3, have characteristics of low voltage and high efficiency.

Claims (6)

1. A compound represented by the following chemical formula 1:
chemical formula 1
Figure FDA0003983159740000011
In the chemical formula 1, the reaction mixture is,
l1 and L2 are directly bonded,
one of Ar1 and Ar2 is selected from the following structural formulae:
Figure FDA0003983159740000012
in the structural formula, in the formula,
y is S, O or CRR',
the R and R' are the same or different from each other and each independently hydrogen, deuterium, or an unsubstituted alkyl group having 1 to 50 carbon atoms,
r4 and R4', which are the same or different from each other, are each independently hydrogen, deuterium, an aryl group of 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium or a nitrile group, or an unsubstituted heterocyclic group of 6 to 20 carbon atoms,
m is an integer of 1 to 8, n is an integer of 1 to 10,
when m and n are 2 or more, R4 in the parentheses may be the same or different from each other,
the other of Ar1 and Ar2 is selected from the following structural formulas:
Figure FDA0003983159740000021
in the structural formula, in the formula,
at least one of X1 to X3 is N, and the others are CR1,
y1 and Y2, which may be the same or different from each other, are each independently an unsubstituted aryl group having 6 to 30 carbon atoms or an unsubstituted heterocyclic group having 2 to 30 carbon atoms,
r1 is hydrogen, and R is hydrogen,
r5 is an unsubstituted aryl group having 6 to 30 carbon atoms,
z4 and Z5, which may be the same or different from each other, are each independently O or S.
2. The compound of claim 1, wherein the compound represented by the chemical formula 1 is selected from the following structural formulae:
Figure FDA0003983159740000031
/>
Figure FDA0003983159740000041
/>
Figure FDA0003983159740000051
/>
Figure FDA0003983159740000061
/>
Figure FDA0003983159740000071
/>
Figure FDA0003983159740000081
/>
Figure FDA0003983159740000091
/>
Figure FDA0003983159740000101
/>
Figure FDA0003983159740000111
/>
Figure FDA0003983159740000121
/>
Figure FDA0003983159740000131
/>
Figure FDA0003983159740000141
/>
Figure FDA0003983159740000151
/>
Figure FDA0003983159740000161
/>
Figure FDA0003983159740000171
/>
Figure FDA0003983159740000181
/>
Figure FDA0003983159740000191
/>
Figure FDA0003983159740000201
3. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and one 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 claim 1 or 2.
4. An organic light-emitting device according to claim 3 wherein the organic layer comprises a light-emitting layer comprising the compound.
5. The organic light emitting device according to claim 3, 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 contains the compound.
6. The organic light-emitting device according to claim 3, 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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* Cited by examiner, † Cited by third party
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CN106816450A (en) * 2015-11-27 2017-06-09 乐金显示有限公司 Organic light-emitting display device
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CN107359257A (en) * 2016-05-10 2017-11-17 三星显示有限公司 Organic light emitting apparatus

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* Cited by examiner, † Cited by third party
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107075359A (en) * 2014-10-15 2017-08-18 三星Sdi株式会社 Organic photoelectric device and display device
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