CN111225895A - Compound and organic light emitting device including the same - Google Patents
Compound and organic light emitting device including the same Download PDFInfo
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- CN111225895A CN111225895A CN201980005103.8A CN201980005103A CN111225895A CN 111225895 A CN111225895 A CN 111225895A CN 201980005103 A CN201980005103 A CN 201980005103A CN 111225895 A CN111225895 A CN 111225895A
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- 230000005525 hole transport Effects 0.000 claims description 18
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
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- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
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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
Technical Field
The present specification relates to a compound and an organic light emitting device including the same.
The present specification claims priority of korean patent application No. 10-2018-0029680, which was filed on 14.3.2018 from the korean patent office, the entire contents of which are incorporated herein.
Background
The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. 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 exert an action such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection may be used.
In order to improve the performance, lifetime, or efficiency of organic light emitting devices, development of materials for organic thin films is continuously required.
Disclosure of Invention
Technical subject
The present specification provides compounds and organic light emitting devices comprising the same.
Means for solving the problems
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
one of Ar1 and Ar2 is represented by the following chemical formula 2,
the other of Ar1 and Ar2 is a substituted or unsubstituted aryl group,
r1 and R2, 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 cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
[ chemical formula 2]
In the above chemical formula 2, Ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted 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 so as 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 include the compound.
Effects of the invention
The compound according to an embodiment of the present application is used for an organic light emitting device, thereby improving luminance of the organic light emitting device, extending lifespan, reducing driving voltage, improving light efficiency, and improving lifespan characteristics of the device based on thermal stability of the compound. Specifically, the compound according to one embodiment of the present invention has a structure having a high electron storage ability and excellent heat resistance because 2 substituents are bonded to one benzene ring of phenanthrene, and thus can maintain an appropriate deposition temperature when manufacturing an organic light emitting device. Further, since the compound of the present invention has a high sublimation temperature, it can be purified at a high purity by a sublimation purification method, and thus contamination of a deposition film forming apparatus or an organic light emitting device during production of the organic light emitting device can be prevented.
Drawings
Fig. 1 illustrates 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 vapor-deposited.
Fig. 2 illustrates 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, an electron injection and transport layer 8, and a cathode 4 are sequentially vapor-deposited.
[ 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: electron injection and 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.
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.
The term "substituted or unsubstituted" as used herein 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, a silyl group, an amino 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 bonded, or having no 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, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
Description of the inventionIn the book, the amine group may be selected from-NH2The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrylfluorenylamino group, and an N-biphenylfluorenylamino group.
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 heterocyclic 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 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,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiapyrrolyl, phenanthrolinyl (phenylanthralinyl group), isoquinoyl
Azolyl, thiadiazolyl, phenothiazinyl, phenoxazine
Oxazine groups, and their fused structures, and the like, but are not limited thereto.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2, R1, R2, Ar1, Ar2 and Ar3 are the same as defined in chemical formula 1.
In one embodiment of the present specification, not the other of Ar1 and Ar2 in the chemical formula 2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, not the other of Ar1 and Ar2 in the chemical formula 2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, the other one of Ar1 and Ar2, which is not represented by chemical formula 2, is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.
In one embodiment of the present specification, the other one of Ar1 and Ar2, which is not represented by the chemical formula 2, is phenyl, biphenyl, terphenyl, or naphthyl.
In one embodiment of the present specification, the other of Ar1 and Ar2, which is not represented by the chemical formula 2, is a phenyl group or a biphenyl group.
In one embodiment of the present specification, one of Ar1 and Ar2 other than the one of chemical formula 2 is a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, the other of Ar1 and Ar2, which is not represented by the above chemical formula 2, is a phenyl group.
In one embodiment of the present specification, Ar3 represents a substituted or unsubstituted aryl group having 6 to 36 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 36 carbon atoms.
In one embodiment of the present specification, Ar3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, Ar3 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms which contains N, O or S.
In one embodiment of the present specification, Ar3 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group containing at least one of O and S, having 2 to 20 carbon atoms.
In one embodiment of the present specification, Ar3 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.
In one embodiment of the present specification, Ar3 represents an aryl group substituted or unsubstituted with deuterium or an aryl group, or a heterocyclic group.
In one embodiment of the present specification, Ar3 represents a phenyl group substituted or unsubstituted with deuterium or an aryl group, a biphenyl group substituted or unsubstituted with deuterium or an aryl group, a naphthyl group substituted or unsubstituted with deuterium or an aryl group, a phenanthryl group substituted or unsubstituted with deuterium or an aryl group, a dibenzofuranyl group, a dibenzothienyl group, a benzonaphthofuranyl group, or a benzonaphthothienyl group.
In one embodiment of the present specification, Ar3 denotes a phenyl group substituted or unsubstituted with deuterium, a phenyl group, or a naphthyl group; biphenyl substituted or unsubstituted with deuterium, phenyl or naphthyl; naphthyl substituted or unsubstituted with deuterium, phenyl or naphthyl; phenanthryl substituted or unsubstituted with deuterium, phenyl or naphthyl; a dibenzofuranyl group; a dibenzothienyl group; a benzonaphthofuranyl group; or benzonaphthothienyl.
In one embodiment of the present specification, Ar3 denotes a phenyl group substituted or unsubstituted with deuterium or naphthyl; a biphenyl group; naphthyl substituted or unsubstituted by phenyl; phenanthryl; a dibenzofuranyl group; a dibenzothienyl group; a benzonaphthofuranyl group; or benzonaphthothienyl.
In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each is independently hydrogen or deuterium.
In one embodiment of the present specification, R1 and R2 are hydrogen.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is selected from the following structural formulae.
In addition, the present specification provides the above-mentioned organic light emitting device comprising the above-mentioned compound.
In one 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 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.
In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.
In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.
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 application, the organic layer includes a light emitting layer having a thickness of
To
Preferably, it is
To
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 disclosure, the organic layer includes a light emitting layer, and the light emitting layer further includes a dopant material.
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 1:1 to 200: 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 20:1 to 200: 1.
In one embodiment of the present application, the light-emitting layer includes a pyrene compound, an anthracene compound, a boron compound, or the like as a dopant substance, but is not limited thereto.
In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula a-1.
[ chemical formula A-1]
In the above-mentioned chemical formula A-1,
n is an integer of 1 or more,
ar11 is substituted or unsubstituted benzofluorenyl with valency of more than 1, substituted or unsubstituted fluoranthenyl with valency of more than 1, substituted or unsubstituted pyrenyl with valency of more than 1, or substituted or unsubstituted pyrenyl with valency of more than 1
The base group is a group of a compound,
l11 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar12 and Ar13, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted heteroaryl group, or may be combined with each other to form a substituted or unsubstituted ring,
when n is 2 or more, the structures in parentheses are the same or different from each other.
In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the chemical formula a-1 as a dopant of the light emitting layer.
According to an embodiment of the present invention, L11 is a direct bond.
According to an embodiment of the present application, n is 2.
In one embodiment of the present application, Ar11 is 2-valent pyrenyl substituted or unsubstituted with deuterium, methyl, ethyl, isopropyl, or tert-butyl; or 2-valent unsubstituted or substituted by deuterium, methyl, ethyl, isopropyl or tert-butyl
And (4) a base.
In one embodiment of the present application, Ar11 is a 2-valent pyrenyl group substituted or unsubstituted with a methyl group.
According to one embodiment of the present application, Ar12 and A1r3 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present application, Ar12 and Ar13 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with an alkyl group, or a heteroaryl group substituted or unsubstituted with an alkyl group.
In one embodiment of the present application, Ar12 and Ar13 are the same as or different from each other, and each independently represents an aryl group or a heteroaryl group which is unsubstituted or substituted with a methyl group, an ethyl group, or an isopropyl group.
According to an embodiment of the present application, Ar12 and Ar13 are the same or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a methyl group, or a dibenzofuranyl group.
In one embodiment of the present application, the chemical formula a-1 may be represented by the following structural formula.
In one embodiment of the present invention, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.
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 includes 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 application, 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 so as to face the first electrode, a light-emitting layer provided between the first electrode and the second electrode, and 2 or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the 2 or more organic layers contains the compound.
In one embodiment of the present application, the organic layer further includes a hole injection layer.
In one embodiment of the present application, the organic layer further includes a hole transport layer.
In one embodiment of the present application, the organic layer further includes an electron blocking layer.
In one embodiment of the present application, the organic layer further includes an electron injection and transport layer.
In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound.
In another embodiment, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate (normal type).
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 and 2 illustrate 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-described compound may be contained in the above-described light-emitting layer 3.
Fig. 2 illustrates a structure 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, an electron injection and transport layer 8, and a cathode 4 are sequentially stacked. In the structure as described above, the above-described compound may be contained in the above-described 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 1 or more of the organic layers contain the compound of the present application, i.e., contain 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 material or different materials.
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 method, forming 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 to form an organic layer not only by a vacuum evaporation method but also 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 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 SnO2: 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 LiO2And a multilayer structure material 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: the organic light-emitting device has an ability to transport holes, has a hole injection effect from an anode, has an excellent hole injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and has excellent thin film formation 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.
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 a good 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 condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder-type furan compound
Pyrimidine derivatives, etc., but are not limited thereto.
The electron transport layer receives electrons from the electron injection layer and transports the electrons to the electron emission layerIn the layer of the optical layer, the electron-transporting substance is a substance that can favorably receive electrons from the cathode and transfer them 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 Alq3Organic radical compounds, hydroxyl brass-metal 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: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The above-mentioned hole resistorThe barrier layer is a layer that prevents holes from reaching the cathode and can be formed generally under the same conditions as the hole injection 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.
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.
< production example >
The compound represented by the above chemical formula 1 is introduced with a bromine group by bromination in 9-chloroanthracene, and an aryl group or a heteroaryl group by Suzuki reaction, as shown below. Then, a borate is introduced by a boronation reaction, and finally, the compound of the specific example is synthesized stepwise by the process of introducing a phenanthryl group.
Production example 1-1
Synthesis of Compound 1-A
50g (235mmol) of 9-chloroanthracene and 500mL of chloroform were mixed and cooled to 0 ℃. 235mL of bromine was slowly added dropwise at 0 ℃ and then stirred at room temperature for 3 hours. After the reaction, the organic layer was extracted with an aqueous solution of sodium thiosulfate, followed by 2-times recrystallization with chloroform and hexane to obtain compound 1-A (58.3g) (yield 85%).
MS[M+H]+＝291
Production example 2-1
Synthesis of Compound 2-A
30g (103mmol) of 1-A, 103mmol of [1,1' -biphenyl ] -4-ylboronic acid, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. Potassium carbonate (309mmol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization from chloroform and hexane to obtain 33.1g of compound 2-a (yield 88%).
MS[M+H]+＝365
Production example 2-2
Synthesis of Compound 2-B
30g (103mmol) of 1-A, 103mmol of [1,1' -biphenyl ] -3-ylboronic acid, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. Potassium carbonate (309 mm. mu. ol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization using chloroform and hexane, thereby obtaining 32.3g of compound 2-B (yield 86%).
MS[M+H]+＝365
Production examples 2 to 3
Synthesis of Compound 2-C
30g (103mmol) of 1-A, 103mmol of naphthalen-1-ylboronic acid, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. Potassium carbonate (309mmol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization using chloroform and hexane, thereby obtaining 28.3g of compound 2-C (yield 81%).
MS[M+H]+＝339
Production examples 2 to 4
Synthesis of Compound 2-D
30g (103mmol) of 1-A, 103mmol of dibenzo [ b, d ] thiophen-4-ylboronic acid, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. Potassium carbonate (309mmol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization from chloroform and hexane to obtain 33.8g of compound 2-D (yield 83%).
MS[M+H]+＝395
Production examples 2 to 5
Synthesis of Compound 2-E
30g (103mmol) of 1-A, 103mmol of (phenyl-d 5) boric acid, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. Potassium carbonate (309mmol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization from chloroform and hexane to obtain 26.3g of compound 2-E (yield 87%).
MS[M+H]+＝294
Production examples 2 to 6
Synthesis of Compound 2-F
30g (103mmol) of 1-A, 103mmol of dibenzo [ b, d ] furan-2-ylboronic acid, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. Potassium carbonate (309mmol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization from chloroform and hexane to obtain 32.8g of compound 2-F (yield 84%).
MS[M+H]+＝379
Production examples 2 to 7
Synthesis of Compound 2-G
30g (103mmol) of 1-A, 103mmol of naphtho [2,3-b ] benzofuran-4-ylboronic acid, 200mL of tetrahydrofuran and 100mL of water are mixed and heated to 60 ℃. Potassium carbonate (309mmol) and tetrakis (triphenylphosphine) palladium (2mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2-times recrystallization from chloroform and hexane to obtain 35.3G of compound 2-G (yield 80%).
MS[M+H]+＝429
Production example 3-1
Synthesis of Compound 3-A
25.5g (70mmol) of 2-A, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 27.8g (yield: 87%) of compound 3-a.
MS[M+H]+＝457
Production example 3-2
Synthesis of Compound 3-B
25.5g (70mmol) of 2-B, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 28.1g (yield 88%) of compound 3-B.
MS[M+H]+＝457
Production examples 3 to 3
Synthesis of Compound 3-C
23.7g (70mmol) of 2-C, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 25.6g (yield: 85%) of compound 3-C.
MS[M+H]+＝431
Production examples 3 to 4
Synthesis of Compound 3-D
27.6g (70mmol) of 2-D, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 27.9g (yield 82%) of compound 3-D.
MS[M+H]+＝487
Production examples 3 to 5
Synthesis of Compound 3-E
20.6g (70mmol) of 2-E, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 23.2g (yield 86%) of compound 3-E.
MS[M+H]+＝386
Production examples 3 to 6
Synthesis of Compound 3-F
26.5g (70mmol) of 2-F, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 27.6g (yield: 84%) of compound 3-F.
MS[M+H]+＝471
Production examples 3 to 7
Synthesis of Compound 3-G
30G (70mmol) of 2-G, 70mmol of bis (pinacolato) diboron, 140mmol of potassium acetate and 250mL of 1, 4-bis
The alkanes were mixed and heated to 100 ℃.1 mmol% of palladium acetate was added thereto, and the mixture was stirred under reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified with chloroform/hexane by column chromatography to obtain 24.6G (yield 82%) of compound 3-G.
MS[M+H]+＝429
Production example 4-1
Synthesis of Compound 1
13.7g (30mmol) of the compound 3-A, 30mmol of 3-chloro-2-phenylphenanthrene and 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction chamber is returned toThe organic layer was extracted from the warm reaction solution, followed by 2-time recrystallization from chloroform and hexane to obtain compound 1(11g) (yield 63%).
MS[M+H]+＝583
Production example 4-2
Synthesis of Compound 2
13.7g (30mmol) of the compound 3-B, 30mmol of 3-chloro-2-phenylphenanthrene and 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 2(11.4g) (yield 65%).
MS[M+H]+＝583
Production examples 4 to 3
Synthesis of Compound 3
12.9g (30mmol) of the compound 3-C, 30mmol of 3-chloro-2-phenylphenanthrene and 100mL of 1, 4-bis
The mixture was heated to 60 ℃ with 50mL of water and an alkane. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 3(10.2g) (yield 61%).
MS[M+H]+＝557
Production examples 4 to 4
Synthesis of Compound 4
14.6g (30mmol) of the compound 3-D, 30mmol of 3-chloro-2-phenylphenanthrene, 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 4(11.6g) (yield 63%).
MS[M+H]+＝613
Production examples 4 to 5
Synthesis of Compound 5
11.6g (30mmol) of the compound 3-E, 30mmol of 3-chloro-2-phenylphenanthrene, 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 5(9.8g) (yield 64%).
MS[M+H]+＝512
Production examples 4 to 6
Synthesis of Compound 6
14.1g (30mmol) of the compound 3-F and 30mmol of 2-chloro-3-benzenePhenanthrene, 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 6(10.9g) (yield 61%).
MS[M+H]+＝597
Production examples 4 to 7
Synthesis of Compound 7
15.6G (30mmol) of the compound 3-G, 30mmol of 2-chloro-3-phenylphenanthrene and 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 7(12.6g) (yield 65%).
MS[M+H]+＝647
Production examples 4 to 8
Synthesis of Compound 8
13.7g (30mmol) of the compound 3-A, 30mmol of 3-chloro-2- (naphthalen-1-yl) phenanthrene, 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added under refluxStirred for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 8(11.9g) (yield 63%).
MS[M+H]+＝633
Production examples 4 to 9
Synthesis of Compound 9
13.7g (30mmol) of Compound 3-A, 30mmol of 3-chloro-2- (naphthalen-2-yl) phenanthrene, 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane to obtain compound 9(11.6g) (yield 61%).
MS[M+H]+＝633
Production examples 4 to 10
Synthesis of Compound 10
13.7g (30mmol) of the compound 3-A and 30mmol of 2- ([1,1' -biphenyl)]-3-yl) -3-chlorophenanthrene, 100mL of 1, 4-bis
The alkane was mixed with 50mL of water and heated to 60 ℃. Potassium phosphate (90mmol) and tetrakis (triphenylphosphine) palladium (0.4mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, followed by 2 recrystallizations from chloroform and hexane, thereby obtaining compound 10(13g) (yield 66%).
MS[M+H]+＝659
The compound represented by chemical formula 1 can be synthesized by introducing various substituents using the same reaction as in the above reaction formula.
< Experimental example >
Comparative example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, 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, Hexaazatriphenylene (HAT) of the following chemical formula was added
The thickness of (3) was subjected to thermal vacuum evaporation to form a hole injection layer.
On the hole injection layer, the following compound 4-4' -bis [ N- (1-naphthyl) -N-phenylamino ] group as a hole-transporting substance]Biphenyl (NPB)
Vacuum evaporation is performed to form a hole transport layer.
On the hole transport layer, in a film thickness
Vacuum evaporation of the following compound N- ([1,1' -diphenyl)]-4-yl) -N- (4- (11- ([1,1' -biphenyl)]-4-yl) -11H-benzo [ a]Carbazol-5-yl) phenyl) - [1,1' -biphenyl]-4-amines (EB1)
Thereby forming an electron blocking layer.
Next, on the above electron blocking layer, BH and BD shown below were added at a weight ratio of 25:1 and in a film thickness
Vacuum evaporation is performed to form a light emitting layer.
On the light-emitting layer, the following compound ET1 and the following compound LiQ (8-hydroxyquinoline lithium) were vacuum-evaporated at a weight ratio of 1:1 to obtain a light-emitting layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Experimental examples 1-1 to 1-10
An organic light-emitting device was produced in the same manner as in comparative example 1, except that in comparative example 1, the compound produced in production examples 1-1 to 4-10 and described in table 1 below was used instead of compound BH.
Comparative examples 1-1 to 1-3
An organic light-emitting device was produced in the same manner as in comparative example 1, except that in comparative example 1, compounds of BH1 to BH3 described below in table 1 were used instead of compound BH.
When a current was applied to the organic light emitting devices fabricated according to comparative example 1, experimental examples 1-1 to 1-10, and comparative examples 1-1 to 1-3, the voltage, efficiency, and color coordinates were measured, and the results are shown in table 1 below.
[ Table 1]
As shown in table 1 above, the devices of experimental examples 1-1 to 1-10 using the compound having the structure of chemical formula 1 as a core all obtained results of voltage reduction and efficiency improvement as compared with the device using the substance of compound BH in comparative example 1.
Further, it is understood that characteristics are improved in terms of voltage and efficiency when the compound of chemical formula 1 of the present application is applied to a device as compared with the devices of comparative examples 1-1 to 1-3.
As shown in the results of table 1 above, it was confirmed that the compounds of phenanthrene according to the present invention, in which substituents are bonded to the 2 nd and 3 rd positions, have high hole and electron conductivities, and thus, low-voltage, high-efficiency organic light emitting devices can be realized.
Claims (12)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
one of Ar1 and Ar2 is represented by the following chemical formula 2,
the other of Ar1 and Ar2 is a substituted or unsubstituted aryl group,
r1 and R2, 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 cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
chemical formula 2
In the chemical formula 2, Ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2:
chemical formula 1-1
Chemical formula 1-2
In the chemical formulae 1-1 and 1-2, R1, R2, Ar1, Ar2 and Ar3 are the same as defined in claim 1.
3. The compound of claim 1, wherein the other of Ar1 and Ar2 that is not of formula 2 is a substituted or unsubstituted phenyl.
4. The compound of claim 1, wherein said Ar3 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.
5. The compound of claim 1, wherein Ar3 is an aryl group substituted or unsubstituted with deuterium or an aryl group, or a heterocyclic group.
6. The compound of claim 1, wherein said R1 and R2 are hydrogen.
7. The compound of claim 1, wherein the compound represented by the chemical formula 1 is selected from the following structural formulae:
8. 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 any one of claims 1 to 7.
9. The organic light emitting device of claim 8, wherein the organic layer comprises a light emitting layer comprising the compound.
10. The organic light emitting device of claim 8, wherein the organic layer comprises a hole blocking layer comprising the compound.
11. The organic light emitting device according to claim 8, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.
12. The organic light-emitting device according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound.
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| WO2019177393A1 (en) | 2019-09-19 |
| KR102230988B1 (en) | 2021-03-23 |
| KR20190108517A (en) | 2019-09-24 |
| CN111225895B (en) | 2022-07-19 |
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