CN112601732A - Novel compound and organic light emitting device comprising same - Google Patents

Novel compound and organic light emitting device comprising same Download PDF

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CN112601732A
CN112601732A CN201980055108.1A CN201980055108A CN112601732A CN 112601732 A CN112601732 A CN 112601732A CN 201980055108 A CN201980055108 A CN 201980055108A CN 112601732 A CN112601732 A CN 112601732A
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李成宰
车龙范
洪性佶
洪玩杓
文贤真
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LG Chem Ltd
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Abstract

The invention provides a novel compound and an organic light emitting device using the same.

Description

Novel compound and organic light emitting device comprising same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0122688, 15, 2018 and korean patent application No. 10-2019-0127309, 14, 10, 2019, including the entire contents disclosed in the documents of the korean patent application as a part of the present specification.
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic electroluminescent device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure BDA0002947446000000021
In the above-described chemical formula 1,
Ar1and Ar2Each independently is C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S5-60(ii) a heteroaryl group, wherein,
Ar3and Ar4Each independently is C6-60Aryl group, however, Ar3And Ar4At least one of which is biphenyl or naphthyl.
In addition, the present invention 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 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
Effects of the invention
The compound according to the present invention can be used as a material for an organic layer of an organic light emitting device in which improvement in efficiency, low driving voltage, and/or improvement in lifetime characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 5, an electron suppression layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4.
Fig. 3 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 5, an electron suppression layer 6, a light-emitting layer 3, a hole suppression layer 9, an electron transport layer 7, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
In the context of the present specification,
Figure BDA0002947446000000032
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio (Alkyl thio); arylthio (Aryl thio); alkylsulfonyl (Alkyl sulfonyl); arylsulfonyl (Aryl sulfonyl); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents being bonded. 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, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
Figure BDA0002947446000000031
In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
Figure BDA0002947446000000041
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
Figure BDA0002947446000000042
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.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but 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 aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a perylenyl group, a perylene group,
Figure BDA0002947446000000052
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be
Figure BDA0002947446000000051
And the like. But is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure BDA0002947446000000053
Azolyl group,
Figure BDA0002947446000000054
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Figure BDA0002947446000000061
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Figure BDA0002947446000000062
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and in addition thereto, the above description about the aryl group can be applied. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and in addition to this, the above description on the heterocyclic group can be applied.
The present invention provides a compound represented by the above chemical formula 1.
In the compound represented by the above chemical formula 1, in one phenyl group bonded to the nitrogen atom of the amine of the triarylamine, an aryl group is introduced only at the ortho (ortho) position with respect to the nitrogen atom, and the HOMO and LUMO levels of the compound are adjusted by introducing such a substituent, whereby an excellent effect that the energy barrier with each organic layer can be adjusted can be obtained.
Specifically, Ar1And Ar2May each independently be C6-30An aryl group; or C6-28An aryl group; or C6-25An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S5-30A heteroaryl group; or C8-20A heteroaryl group; or C12-18A heteroaryl group. Preferably, Ar1And Ar2Each of which may be independently any one of phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-9H-carbazolyl, phenyl substituted with naphthyl, phenyl substituted with phenanthryl, or phenyl substituted with triphenylene.
Specifically, Ar3And Ar4May each independently be C6-30Aryl, or C6-25Aryl, or C6-18And (4) an aryl group. Preferably, Ar3And Ar4Each independently phenyl, biphenyl, terphenyl, or naphthyl.
Specifically, Ar1And Ar2And Ar3And Ar4May each be the same as one another or different from one another.
As an example, Ar1And Ar2And Ar3And Ar4At least one or more pairs of may be identical to each other. For example, Ar1And Ar2May be identical to each other, Ar3And Ar4May be different from each other. Further, Ar1And Ar2May be different from each other, Ar3And Ar4May be identical to each other. Or Ar1And Ar2May be identical to each other, Ar3And Ar4Or may be identical to each other.
Here, Ar is1And Ar2Are identical to each other, Ar2And Ar2May be phenyl, biphenyl, terphenyl, naphthyl or dimethylfluorenyl.
As an example, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 1-1 to 1-12.
[ chemical formula 1-1]
Figure BDA0002947446000000071
[ chemical formulas 1-2]
Figure BDA0002947446000000072
[ chemical formulas 1-3]
Figure BDA0002947446000000073
[ chemical formulas 1 to 4]
Figure BDA0002947446000000074
[ chemical formulas 1 to 5]
Figure BDA0002947446000000081
[ chemical formulas 1 to 6]
Figure BDA0002947446000000082
[ chemical formulas 1 to 7]
Figure BDA0002947446000000083
[ chemical formulas 1 to 8]
Figure BDA0002947446000000084
[ chemical formulas 1 to 9]
Figure BDA0002947446000000091
[ chemical formulas 1-10]
Figure BDA0002947446000000092
[ chemical formulas 1 to 11]
Figure BDA0002947446000000093
[ chemical formulas 1 to 12]
Figure BDA0002947446000000094
In the above chemical formulas 1-1 to 1-12,
Ar1and Ar2As defined in the above chemical formula 1,
R1、R2、R3、R4and R5Each independently is hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; c6-60An aryl group; c6-60Aralkyl group; c6-60An aralkenyl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S5-60A heteroaryl group.
Specifically, R is as defined above1、R2、R3、R4And R5May be hydrogen.
On the other hand, the compound represented by the above chemical formula 1 may be Ar substituted on the nitrogen atom of the amine of triarylamine1、Ar2Stereoisomers (stereo-isomers) in which the left and right positions are changed by rotation are all included.
Representative examples of the compound represented by the above chemical formula 1 are shown below.
Figure BDA0002947446000000101
Figure BDA0002947446000000111
Figure BDA0002947446000000121
Figure BDA0002947446000000131
Figure BDA0002947446000000141
Figure BDA0002947446000000151
Figure BDA0002947446000000161
Figure BDA0002947446000000171
Figure BDA0002947446000000181
Figure BDA0002947446000000191
Figure BDA0002947446000000201
Figure BDA0002947446000000211
Figure BDA0002947446000000221
Figure BDA0002947446000000231
Figure BDA0002947446000000241
Figure BDA0002947446000000251
Figure BDA0002947446000000261
Figure BDA0002947446000000271
Figure BDA0002947446000000281
Figure BDA0002947446000000291
Figure BDA0002947446000000301
Figure BDA0002947446000000311
On the other hand, the compound represented by the above chemical formula 1 can be produced by the method shown in the following reaction formulas 1 to 2.
[ reaction formula 1]
Figure BDA0002947446000000321
[ reaction formula 2]
Figure BDA0002947446000000322
In the above reaction formulae 1 to 2, Ar1、Ar2、Ar3And Ar4As defined in the above chemical formula 1, X1To X4Each independently is a halogen group.
Specifically, in the reaction formula 1, an aryl group (Ar) is introduced on both sides of the ortho (ortho) position of the phenylamine3，Ar4) The reaction of (1).
The above reaction formula 1 can be carried out using a palladium catalyst (Pd catalyst) in the presence of a base (base). As an example, in the above reaction formula 1, as the alkali component, potassium carbonate (K) can be used2CO3) For example, bis (tri-tert-butylphosphine) palladium (BTP, bis (tri-tert-butylphosphine) palladium) or the like can be used as the palladium catalyst.
The reaction (I) in the reaction formula 1 is a reaction in which an aryl group is introduced into one of ortho (ortho) positions of a phenylamine, and the phenylamine substituted with a halogen group at the ortho (ortho) position and an arylboronic acid (Ar) are reacted in the presence of a base (base) using a palladium catalyst (Pd catalyst)3-B(OH)2) Carrying out reaction. After the aryl group is introduced into one of the ortho (ortho) positions of the phenylamine as described above, the resulting mixture is reacted with another arylboronic acid (Ar) as shown in the reaction (II) in the above reaction formula 14-B(OH)2) The reaction proceeds so that the aryl group is also introduced into the adjacent (ortho) position of the phenylamine.
Here, in Ar3And Ar4In the same case, it is possible to omitReaction (II) in reaction formula 1 is carried out by a one-step reaction in which an aryl group is introduced into both sides of the ortho (ortho) position of the phenylamine in reaction (I) at once.
In addition, in the reaction formula 2, an aryl or heteroaryl group (Ar) is further introduced into the phenylamine substituted with a halogen group at the ortho (ortho) position generated by the reaction formula 11，Ar2) The reaction of (1).
The reaction formula 2 may be carried out using a palladium catalyst (Pd catalyst) in the presence of a base (base). In the above reaction formula 2, sodium tert-butoxide (NaOtBu) or the like can be used as the base component, and bis (tri-tert-butylphosphine) palladium (BTP) or 1,1' -bis (diphenylphosphino) ferrocene dichloropalladium (II) (Pd (dppf) Cl) can be used as the Pd catalyst2) And the like.
The reaction (III) in the above reaction formula 2 is a reaction in which a diphenylamine (diarylphenylamine) substituted with a halogen group at the ortho (ortho) position generated by the above reaction formula 1, i.e., diarylphenylamine, and a halide (Ar) containing an aryl or heteroaryl group to be substituted are reacted with a palladium catalyst (Pd catalyst) in the presence of a base (base)1-X3) And carrying out the reaction. After the aryl or heteroaryl group is introduced by the reaction (III) in this manner instead of the hydrogen in the diarylphenylamine, the resultant is reacted with another halide (Ar) containing an aryl or heteroaryl group as shown in the reaction (IV) in the above reaction formula 12-X4) The reaction is carried out so that instead of the remaining hydrogen of the phenylamine, all aryl or heteroaryl groups are introduced. Preferably, X3And X4Each independently is bromine or chlorine.
Here, in Ar1And Ar2In the same manner, the reaction (IV) in the above reaction formula 2 may be omitted, and in the reaction (III), the aryl or heteroaryl group may be introduced to both sides at once to replace 2 hydrogens of diarylphenylamine in one step.
In the production methods according to the above reaction formulae 1 to 2, the reactive group used for the amine substitution reaction can be changed as known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention 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 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression 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 addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include an electron inhibiting layer, and in this case, the electron inhibiting layer may be adjacent to the light emitting layer, and the electron inhibiting layer may include the compound represented by chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1. In particular, the compounds according to the invention can be used as dopants in the light-emitting layer.
In addition, the organic layer may include a hole inhibiting layer, and in this case, the hole inhibiting layer may be adjacent to the light emitting layer, and the hole inhibiting layer may include the compound represented by chemical formula 1.
In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer simultaneously performing electron injection and transport, and the electron transport layer, the electron injection layer, or the layer simultaneously performing electron injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a hole transport layer and a light emitting layer, and the hole transport layer may include the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron inhibiting layer and a light emitting layer, and the electron inhibiting layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device of a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an inverted (inverted type) organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
Fig. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 5, an electron suppression layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole transport layer, electron suppression layer, light emitting layer, and electron transport layer.
Fig. 3 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 5, an electron suppression layer 6, a light-emitting layer 3, a hole suppression layer 9, an electron transport layer 7, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole suppression layer, and electron transport layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods well known in the art, except that 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, in the case where 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, and the like 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 represented by the above chemical formula 1 may be formed into 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 layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or 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 include vanadium, chromium, copper, zinc,Metals such as gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material 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 material 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 electron-suppressing layer is a layer including: the electron inhibiting layer is formed on the hole transporting layer, and specifically, is provided in contact with the light emitting layer, and serves to prevent excessive electron transfer, thereby increasing the hole-electron binding efficiency and improving the efficiency of the organic light emitting device. The electron-suppressing layer is preferably a substance having a low mobility with respect to electrons so as not to allow electrons to migrate from the light-emitting layer.
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 a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As a specific 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 BDA0002947446000000361
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; a polyfluorene; rubrene, etc., but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic fused ring 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 carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Figure BDA0002947446000000374
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The hole inhibiting layer is a layer including: specifically, the hole inhibiting layer is provided in contact with the light-emitting layer, and serves to prevent excessive hole migration, thereby increasing the hole-electron binding ratio and improving the efficiency of the organic light-emitting device. The electron-inhibiting layer is preferably a substance having a low mobility for holes so as not to cause holes to migrate from the light-emitting layer again.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and specifically, the electron transport layer is provided in contact with the hole-inhibiting layer. In particular, the electron transport layer is preferably a substance capable of receiving electrons from the cathode and transferring the electrons to the light-emitting layer, as an electron transport substance, and has 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 usual 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 the ability to transport electrons, has the effect of injecting electrons from the cathode, and has excellent electron injection into the light-emitting layer or the light-emitting materialThe compound prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer and has excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Figure BDA0002947446000000372
Azole,
Figure BDA0002947446000000373
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 organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the organic light emitting device represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The manufacture of the novel compound according to the present invention and the organic light emitting device comprising the same is specifically illustrated in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
Synthesis example 1 Synthesis of Compound 1
Step 1) Synthesis of Compound 1-A
Figure BDA0002947446000000381
The above-mentioned compound 7-A (68.0g, yield 85.84%) was obtained by the same method as in step 1 of the above-mentioned Synthesis example 1 using 2, 6-dibromoaniline (50.0g, 199.27mmol) and [1.1' -biphenyl ] -4-ylboronic acid (82.87g, 418.46 mmol).
2, 6-dibromoaniline (50.0g, 199.27mmol) and [1.1' -biphenyl]-4-Ylboronic acid (82.87g, 418.46mmol) dissolved in 1, 4-bis
Figure BDA0002947446000000383
After an alkyl (700mL), a potassium carbonate solution (130.71g, 996.35mmol, water 350mL) was added, and the mixture was stirred under heating for 10 minutes. Adding the solution into the solution to dissolve in 1, 4-bis
Figure BDA0002947446000000384
An alkane (10mL) was added to bis (tri-tert-butylphosphino) palladium (BTP, 0.20g, 0.40mmol), and the mixture was stirred under heating for 1 hour. After completion of the reaction and filtration, the layer was separated with chloroform and water. After the solvent was removed, it was recrystallized from ethyl acetate, thereby obtaining the above-mentioned compound 1-A (68.0g, yield 85.84%).
Step 2) Synthesis of Compound 1-B
Figure BDA0002947446000000382
To the compound 1-A (40.0g, 100.63mmol) obtained in step 1 of the above synthesis example 1, bromobenzene (15.80g, 100.63mmol) and sodium tert-butoxide (21.94g, 228.27mmol) were added toluene (250mL), followed by heating and stirring for 10 minutes. To the above mixture was added 1,1' -bis (diphenylphosphino) ferrocene dichloropalladium (II) (Pd (dppf) Cl) dissolved in toluene (30mL)20.60g, 0.82mmol), and then stirred under heating for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After the solvent was removed, it was recrystallized from ethyl acetate, thereby obtaining the above-mentioned compound 1-B (37.0g, yield 77.63%).
Step 3) Synthesis of Compound 1
Figure BDA0002947446000000391
Xylene (200mL) was added to the compound 1-B (20.0g, 42.23mmol) obtained in step 2 of the above synthesis example 1, 4', 1' -terphenyl (13.32g, 43.07mmol) and sodium tert-butoxide (NaOtBu, 8.37g, 87.11mmol), followed by heating and stirring for 10 minutes. To the above mixture was added bis (tri-tert-butylphosphine) palladium (BTP, 0.16g, 0.31mmol) dissolved in xylene (10mL), and the mixture was stirred under heating for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After the solvent was removed, recrystallization was performed with ethyl acetate, thereby obtaining the above compound 1(21.0g, yield 79.46%). (MS [ M + H ] + ═ 626)
Synthesis example 2 Synthesis of Compound 2
Figure BDA0002947446000000392
Using compound 1-B (20.0g, 42.23mmol) obtained in step 2 of synthesis example 1 above and 3-bromo-9-phenyl-9H-carbazole (13.88g, 43.07mmol), compound 2 above was obtained (21.5g, yield 79.70%) by the same method as in step 3 of synthesis example 1 above. (MS [ M + H ] + ═ 639)
Synthesis example 3 Synthesis of Compound 3
Step 1) Synthesis of Compound 3-A
Figure BDA0002947446000000401
Using compound 1-A (40.0g, 100.63mmol) obtained in step 1 of the above synthesis example 1 and 4-bromo-1.1' -biphenyl (23.46g, 100.63mmol), the above compound 3-A (47.7g, yield 86.23%) was obtained by the same method as in step 2 of the above synthesis example 1.
Step 2) Synthesis of Compound 3
Figure BDA0002947446000000402
Using compound 3-A (20.0g, 36.38mmol) obtained in step 1 of the above synthesis example 3 and 1-bromodibenzo [ b, d ] furan (9.17g, 37.11mmol), the above compound 3(19.5g, yield 74.87%) was obtained in the same manner as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 716)
Synthesis example 4 Synthesis of Compound 4
Figure BDA0002947446000000403
Using compound 3-A (20.0g, 36.38mmol) obtained in step 1 of the above synthesis example 3 and 2-bromodibenzo [ b, d ] thiophene (9.77g, 37.11mmol), the above compound 4(20.4g, yield 76.61%) was obtained by the same method as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 732)
Synthesis example 5 Synthesis of Compound 5
Figure BDA0002947446000000411
Using compound 3-A (20.0g, 36.38mmol) obtained in step 1 of the above synthesis example 3 and 2-bromo-9, 9-dimethyl-9H-fluorene (10.14g, 37.11mmol), the above compound 5(21.7g, yield 80.40%) was obtained by the same method as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 742)
Synthesis example 6 Synthesis of Compound 6
Figure BDA0002947446000000412
Xylene (200mL) was added to the compound 1-A (15.0g, 37.73mmol) obtained in step 1 of the above synthesis example 1, 2-bromonaphthalene (16.02g, 77.35mmol) and sodium tert-butoxide (16.45g, 171.19mmol), and then the mixture was stirred under heating for 10 minutes. To the mixture was added bis (tri-tert-butylphosphine) palladium (0.25g, 0.49mmol) dissolved in xylene (15mL), and the mixture was stirred under heating for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, recrystallization from ethyl acetate was carried out, whereby the above-mentioned compound 6(20.5g, yield 83.61%) was obtained. (MS [ M + H ] + ═ 650)
Synthesis example 7 Synthesis of Compound 7
Figure BDA0002947446000000413
Using compound 1-A (15.0g, 37.73mmol) obtained in step 1 of the above synthesis example 1 and 4-bromo-1.1' -biphenyl (18.03g, 77.35mmol), the above compound 7(22.5g, yield 84.96%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 702)
Synthesis example 8 Synthesis of Compound 8
Figure BDA0002947446000000421
Using compound 1-A (15.0g, 37.73mmol) obtained in step 1 of the above synthesis example 1 and 2-bromo-9, 9-dimethyl-9H-fluorene (21.13g, 77.35mmol), the above compound 8(23.4g, yield 79.30%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 782)
Synthesis example 9 Synthesis of Compound 9
Step 1) Synthesis of Compound 9-A
Figure BDA0002947446000000422
The above-mentioned compound 9-A (52.0g, yield 75.54%) was obtained by the same method as in step 1 of the above-mentioned Synthesis example 1 using 2, 6-dibromoaniline (50.0g, 199.27mmol) and naphthalen-1-ylboronic acid (71.97g, 418.46 mmol).
Step 2) Synthesis of Compound 9-B
Figure BDA0002947446000000423
Using compound 9-A (40.0g, 115.79mmol) obtained in step 1 of the above synthesis example 9 and 4-bromo-1.1' -biphenyl (26.99g, 115.79mmol), the above compound 9-B (46.1g, yield 80.00%) was obtained by the same method as in step 2 of the above synthesis example 1.
Step 3) Synthesis of Compound 9
Figure BDA0002947446000000431
Using compound 9-B (20.0g, 40.19mmol) obtained in step 2 of the above synthesis example 9 and 2-bromo-9, 9-dimethyl-9H-fluorene (11.20g, 40.99mmol), the above compound 9(21.8g, yield 78.62%) was obtained by the same method as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 690)
Synthesis example 10 Synthesis of Compound 10
Figure BDA0002947446000000432
Using compound 9-A (15.0g, 43.42mmol) obtained in step 1 of the above synthesis example 9 and 4-bromo-1.1' -biphenyl (20.75g, 89.01mmol), the above compound 10(22.7g, yield 80.45%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 650)
Synthesis example 11 Synthesis of Compound 11
Step 1) Synthesis of Compound 11-A
Figure BDA0002947446000000433
The above-mentioned compound 11-A (56.0g, yield 81.35%) was obtained by the same method as in step 1 of the above-mentioned Synthesis example 1 using 2, 6-dibromoaniline (50.0g, 199.27mmol) and naphthalen-2-ylboronic acid (71.97g, 418.46 mmol).
Step 2) Synthesis of Compound 11-B
Figure BDA0002947446000000441
Using compound 11-A (40.0g, 115.79mmol) obtained in step 1 of the above synthesis example 11 and 4-bromo-1.1' -biphenyl (26.99g, 115.79mmol), the above compound 11-B (48.3g, yield 83.82%) was obtained by the same method as in step 2 of the above synthesis example 1.
Step 3) Synthesis of Compound 11
Figure BDA0002947446000000442
Using compound 11-B (20.0g, 40.19mmol) obtained in step 2 of the above synthesis example 11 and 2-bromo-9, 9-dimethyl-9H-fluorene (11.20g, 40.99mmol), the above compound 11(22.8g, yield 82.23%) was obtained by the same method as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 690)
Synthesis example 12 Synthesis of Compound 12
Figure BDA0002947446000000443
Using compound 11-A (15.0g, 43.42mmol) obtained in step 1 of the above synthesis example 11 and 4-bromo-1.1' -biphenyl (20.75g, 89.01mmol), the above compound 12(23.8g, yield 84.35%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 650)
Synthesis example 13 Synthesis of Compound 13
Step 1) Synthesis of Compound 13-A
Figure BDA0002947446000000451
2-bromo-6-chloroaniline (50.0g, 242.17mmol) and phenylboronic acid (31.00g, 254.27mmol) were dissolved in 1, 4-bis
Figure BDA0002947446000000454
After an alkyl (600mL), a potassium carbonate (100.41g, 726.51 mmol: water 300mL) solution was added, and the mixture was stirred under heating for 10 minutes. At the upper partAdding the solution into the solution to be dissolved in 1, 4-bis
Figure BDA0002947446000000455
Figure BDA0002947446000000455
1,1' -bis (diphenylphosphino) ferrocene dichloropalladium (II) (0.89g, 1.21mmol) in an alkane (50mL) was stirred with heating for 1 hour. After completion of the reaction and filtration, the layer was separated with chloroform and water. After the solvent was removed, it was recrystallized from ethyl acetate, thereby obtaining the above-mentioned compound 13-A (40.0g, yield 81.10%).
Step 2) Synthesis of Compound 13-B
Figure BDA0002947446000000452
Compound 13-A (40.0g, 196.40mmol) obtained in step 1 of the above Synthesis example 13 and [1.1' -Biphenyl]-4-Ylboronic acid (40.84g, 206.22mmol) dissolved in 1, 4-bis
Figure BDA0002947446000000456
After an alkyl (500mL), a potassium carbonate (81.43g, 589.20 mmol: water 250mL) solution was added, and the mixture was stirred under heating for 10 minutes. Adding the solution into the solution to dissolve the 1, 4-bis
Figure BDA0002947446000000457
Bis (tri-tert-butylphosphino) palladium (0.50g, 0.98mmol) in an alkane (25mL) was stirred with heating for 1 hour. After completion of the reaction and filtration, the layer was separated with chloroform and water. After the solvent was removed, the residue was recrystallized from ethyl acetate, whereby the above-mentioned compound 13-B (48.0g, yield 76.04%) was obtained.
Step 3) Synthesis of Compound 13
Figure BDA0002947446000000453
Using compound 13-B (15.0g, 46.67mmol) obtained in step 2 of the above synthesis example 13 and 2-bromo-9, 9-dimethyl-9H-fluorene (26.13g, 95.67mmol), the above compound 13(26.4g, yield 78.92%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 706)
Synthesis example 14 Synthesis of Compound 14
Step 1) Synthesis of Compound 14-A
Figure BDA0002947446000000461
Using compound 13-A (40.0g, 196.40mmol) obtained in step 1 of the above synthesis example 13 and naphthalen-1-ylboronic acid (35.47g, 206.22mmol), the above compound 14-A (45.0g, yield 77.57%) was obtained by the same method as in step 2 of the above synthesis example 13.
Step 2) Synthesis of Compound 14
Figure BDA0002947446000000462
Using compound 14-A (15.0g, 50.78mmol) obtained in step 1 of the above synthesis example 14 and 4-bromo-1.1' -biphenyl (24.27g, 104.10mmol), the above compound 14(25.2g, yield 82.74%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 600)
Synthesis example 15 Synthesis of Compound 15
Figure BDA0002947446000000463
Using compound 14-A (15.0g, 50.78mmol) obtained in step 1 of the above synthesis example 14 and 4-bromo-1, 1':4', 1' -terphenyl (32.19g, 104.10mmol), the above compound 15(30.5g, yield 79.87%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 752)
Synthesis example 16 Synthesis of Compound 16
Step 1) Synthesis of Compound 16-A
Figure BDA0002947446000000471
Using compound 13-A (40.0g, 196.40mmol) obtained in step 1 of the above Synthesis example 13 and naphthalen-2-ylboronic acid (35.47g, 206.22mmol), the above compound 16-A (46.0g, yield 79.29%) was obtained by the same method as in step 2 of the above Synthesis example 13.
Step 2) Synthesis of Compound 16
Figure BDA0002947446000000472
Using compound 16-A (15.0g, 50.78mmol) obtained in step 1 of the above synthesis example 16 and 4-bromo-1.1' -biphenyl (24.27g, 104.10mmol), the above compound 16(26.0g, yield 85.37%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 600)
Synthesis example 17 Synthesis of Compound 17
Figure BDA0002947446000000473
Using compound 16-A (15.0g, 50.78mmol) obtained in step 1 of the above synthesis example 16 and 2-bromo-9, 9-dimethyl-9H-fluorene (28.44g, 104.10mmol), the above compound 17(26.2g, yield 75.89%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 680)
Synthesis example 18 Synthesis of Compound 18
Step 1) Synthesis of Compound 18-A
Figure BDA0002947446000000481
The above-mentioned compound 18-A (52.0g, yield 76.75%) was obtained by the same method as in step 1 of the above-mentioned Synthesis example 13 using 2-bromo-6-chloroaniline (50.0g, 242.17mmol) and [1.1' -biphenyl ] -4-ylboronic acid (50.35g, 254.27 mmol).
Step 2) Synthesis of Compound 18-B
Figure BDA0002947446000000482
Using compound 18-A (40.0g, 142.97mmol) obtained in step 1 of the above synthesis example 18 and naphthalen-1-ylboronic acid (25.82g, 150.12mmol), the above compound 18-B (40.0g, yield 75.31%) was obtained in the same manner as in step 2 of the above synthesis example 13.
Step 3) Synthesis of Compound 18
Figure BDA0002947446000000483
Using compound 18-B (15.0g, 40.38mmol) obtained in step 2 of the above synthesis example 18 and 2-bromo-9, 9-dimethyl-9H-fluorene (22.61g, 82.78mmol), the above compound 18(24.8g, yield 81.24%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 756)
Synthesis example 19 Synthesis of Compound 19
Step 1) Synthesis of Compound 19-A
Figure BDA0002947446000000491
The above-mentioned compound 19-A (68.0g, yield 78.90%) was obtained by the same method as in step 1 of the above-mentioned Synthesis example 13 using 2-bromo-6-chloroaniline (50.0g, 242.17mmol) and [1.1':4',1 "-terphenyl ] -4-ylboronic acid (69.70g, 254.27 mmol).
Step 2) Synthesis of Compound 19-B
Figure BDA0002947446000000492
Using compound 19-A (40.0g, 112.40mmol) obtained in step 1 of the above synthesis example 19 and [1,1' -biphenyl ] -4-ylboronic acid (23.37g, 118.02mmol), the above compound 19-B (40.0g, yield 75.13%) was obtained by the same method as in step 2 of the above synthesis example 13.
Step 3) Synthesis of Compound 19
Figure BDA0002947446000000493
Using compound 19-B (15.0g, 31.67mmol) obtained in step 2 of the above synthesis example 19 and 2-bromo-9, 9-dimethyl-9H-fluorene (15.13g, 64.93mmol), the above compound 19(20.1g, yield 81.58%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 778)
Synthesis example 20 Synthesis of Compound 20
Step 1) Synthesis of Compound 20-A
Figure BDA0002947446000000501
Using compound 19-B (40.0g, 84.46mmol) obtained in step 2 of the above synthesis example 19 and 4-bromo-1.1' -biphenyl (19.69g, 84.46mmol), the above compound 20-A (42.0g, yield 79.46%) was obtained by the same method as in step 2 of the above synthesis example 1.
Step 2) Synthesis of Compound 20
Figure BDA0002947446000000502
Using compound 20-A (20.0g, 31.96mmol) obtained in step 1 of the above synthesis example 20 and 2-bromo-9, 9-dimethyl-9H-fluorene (8.90g, 32.60mmol), the above compound 20(19.5g, yield 74.58%) was obtained by the same method as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 818)
Synthesis example 21 Synthesis of Compound 21
Step 1) Synthesis of Compound 21-A
Figure BDA0002947446000000503
Using compound 19-A (40.0g, 112.40mmol) obtained in step 1 of the above synthesis example 19 and naphthalen-1-ylboronic acid (20.30g, 118.02mmol), the above compound 21-A (40.0g, yield 79.51%) was obtained by the same method as in step 2 of the above synthesis example 13.
Step 2) Synthesis of Compound 21
Figure BDA0002947446000000511
Using compound 21-A (15.0g, 33.51mmol) obtained in step 1 of the above synthesis example 21 and 4-bromo-1, 1':3', 1' -terphenyl (21.24g, 68.70mmol), the above compound 21(24.0g, yield 79.21%) was obtained by the same method as in the above synthesis example 6. (MS [ M + H ] + ═ 904)
Synthesis example 22 Synthesis of Compound 22
Step 1) Synthesis of Compound 22-A
Figure BDA0002947446000000512
Using compound 21-A (40.0g, 89.37mmol) obtained in step 1 of the above synthesis example 21 and 4-bromo-1.1' -biphenyl (20.83g, 89.37mmol), the above compound 22-A (43.0g, yield 80.22%) was obtained by the same method as in step 2 of the above synthesis example 1.
Step 2) Synthesis of Compound 22
Figure BDA0002947446000000513
Using compound 22-A (20.0g, 33.35mmol) obtained in step 1 of the above synthesis example 22 and 2-bromodibenzo [ b, d ] furan (8.40g, 34.01mmol), the above compound 22(20.0g, yield 75.72%) was obtained in the same manner as in step 3 of the above synthesis example 1. (MS [ M + H ] + ═ 792)
Synthesis example 23 Synthesis of Compound 23
Step 1) Synthesis of Compound 23-A
Figure BDA0002947446000000521
Using compound 19-A (40.0g, 112.40mmol) obtained in step 1 of the above synthesis example 19 and naphthalen-2-ylboronic acid (20.30g, 118.02mmol), the above compound 23-A (42.0g, yield 83.49%) was obtained by the same method as in step 2 of the above synthesis example 13.
Step 2) Synthesis of Compound 23
Figure BDA0002947446000000522
Using compound 23-A (15.0g, 33.51mmol) obtained in step 1 of the above synthesis example 23 and 3-bromo-1, 1' -biphenyl (16.02g, 68.70mmol), the above compound 23(21.0g, yield 83.34%) was obtained in the same manner as in the above synthesis example 6. (MS [ M + H ] + ═ 752)
Synthesis example 24 Synthesis of Compound 24
Figure BDA0002947446000000523
Using compound 23-A (15.0g, 33.51mmol) obtained in step 1 of the above synthesis example 23 and 2-bromodibenzo [ b, d ] furan (16.98g, 68.70mmol), the above compound 24(21.0g, yield 80.35%) was obtained in the same manner as in the above synthesis example 6. (MS [ M + H ] + ═ 780)
< Experimental examples and comparative Experimental examples >
Experimental example 1-1
The Indium Tin Oxide (ITO) is added at 1400 angstroms (A)
Figure BDA0002947446000000524
angstrom) was put in distilled water in which a detergent was dissolved, and the glass substrate coated with a thin film was cleaned 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. Washing the ITO for 30 minutesAfter the lapse of a minute, 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, a compound represented by the following chemical formula HAT was added
Figure BDA0002947446000000531
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, as a hole transport layer, a compound represented by the following chemical formula HT1 and
Figure BDA0002947446000000532
after vacuum deposition, compound 1 produced in synthesis example 1 was deposited as an electron inhibiting layer
Figure BDA0002947446000000533
Thermal vacuum evaporation is performed to a thickness of (1). Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD are represented by 25: 1 in a weight ratio of
Figure BDA0002947446000000534
Vacuum evaporation is performed to a thickness of (1). Next, as a hole inhibiting layer, a compound represented by the following chemical formula HB1 was added
Figure BDA0002947446000000535
Vacuum evaporation is performed to a thickness of (1). Next, as a layer which simultaneously performs electron transport and electron injection, a compound represented by the following chemical formula ET1 and a compound represented by the following LiQ were doped with 1: 1 in a weight ratio of
Figure BDA0002947446000000536
Thermal vacuum evaporation is performed to a thickness of (1). In the above electron transport and electron injection layerSequentially adding lithium fluoride (LiF) to
Figure BDA0002947446000000537
Thickness of aluminum and
Figure BDA0002947446000000538
the cathode is formed by vapor deposition to produce an organic light-emitting device.
Figure BDA0002947446000000541
Experimental examples 1-2 to 1-15 and comparative Experimental examples 1-1 to 1-8
Organic light-emitting devices of experimental examples 1-2 to 1-15 and comparative experimental examples 1-1 to 1-8 were produced by the same method as in experimental example 1-1 above, except that in experimental example 1-1 above, compounds described in table 1 below were used instead of compound 1. The organic light emitting devices manufactured in the experimental example and the comparative experimental example were applied with 10mA/cm2The voltage, efficiency, color coordinates and lifetime were measured at the current of (1), and the results are shown in table 1 below. On the other hand, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
In table 1 below, compounds EB1 to EB8 used for the electron suppression layer are represented by the following chemical formulae EB1 to EB8, respectively.
Figure BDA0002947446000000551
[ TABLE 1]
Figure BDA0002947446000000561
As shown in table 1, it was confirmed that the compound of the present invention has excellent electron-suppressing ability, and that an organic light-emitting device using the compound as an electron-suppressing layer exhibits significant effects in terms of driving voltage, efficiency, and lifetime.
Experimental examples 2-1 to 2-15 and comparative Experimental examples 1-1, 2-1 to 2-7
Organic light-emitting devices of experimental examples 2-1 to 2-15 and comparative experimental examples 2-1 to 2-7 were produced in the same manner as in experimental example 1-1, except that the compound represented by the above chemical formula EB1 was used instead of compound 1 as the electron-inhibiting layer and the compound represented by the following chemical formula HT1 was used instead of the compound represented by the following chemical formula HT1 as the hole-transporting layer in the above experimental example 1-1. The organic light emitting devices manufactured in the experimental example and the comparative experimental example were applied with 10mA/cm2The voltage, efficiency, color coordinates and lifetime were measured at the current of (1), and the results are shown in table 1 below. On the other hand, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
In the following table 2, compounds HT1 to HT8 used for the hole transport layer are represented by the following chemical formulae HT1 to HT8, respectively.
Figure BDA0002947446000000571
[ TABLE 2]
Figure BDA0002947446000000581
As shown in table 2, it was confirmed that the compound of the present invention has excellent hole transport ability, and the organic light emitting device using the compound as a hole transport layer exhibits significant efficiency in terms of driving voltage, efficiency, and lifetime.
[ notation ] to show
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole transport layer 6: electron inhibiting layer
7: electron transport layer 8: hole injection layer
9: a hole inhibiting layer.

Claims (9)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure FDA0002947445990000011
In the chemical formula 1, the first and second organic solvents,
Ar1and Ar2Each independently is C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S5-60(ii) a heteroaryl group, wherein,
Ar3and Ar4Each independently is C6-60Aryl group, however, Ar3And Ar4At least one of which is biphenyl or naphthyl.
2. The compound of claim 1, wherein Ar1And Ar2Each independently is C6-30An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S5-30A heteroaryl group.
3. The compound of claim 1, wherein Ar1And Ar2Each independently is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-9H-carbazolyl, phenyl substituted with naphthyl, phenyl substituted with phenanthryl, or phenyl substituted with triphenylene.
4. The compound of claim 1, wherein Ar3And Ar4Each independently is C6-30And (4) an aryl group.
5. The compound of claim 1, wherein Ar3And Ar4Each independently phenyl, biphenyl, terphenyl, or naphthyl.
6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-12:
chemical formula 1-1
Figure FDA0002947445990000021
Chemical formula 1-2
Figure FDA0002947445990000022
Chemical formulas 1 to 3
Figure FDA0002947445990000023
Chemical formulas 1 to 4
Figure FDA0002947445990000024
Chemical formulas 1 to 5
Figure FDA0002947445990000025
Chemical formulas 1 to 6
Figure FDA0002947445990000031
Chemical formulas 1 to 7
Figure FDA0002947445990000032
Chemical formulas 1 to 8
Figure FDA0002947445990000033
Chemical formulas 1 to 9
Figure FDA0002947445990000034
Chemical formulas 1 to 10
Figure FDA0002947445990000041
Chemical formulas 1 to 11
Figure FDA0002947445990000042
Chemical formulas 1 to 12
Figure FDA0002947445990000043
In the chemical formulas 1-1 to 1-12,
Ar1and Ar2As defined in claim 1, in the same way,
R1，R2，R3，R4and R5Each independently is hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; c6-60An aryl group; c6-60Aralkyl group; c6-60An aralkenyl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S5-60A heteroaryl group.
7. The compound of claim 4, wherein R1、R2、R3、R4And R5Is hydrogen.
8. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
Figure FDA0002947445990000051
Figure FDA0002947445990000061
Figure FDA0002947445990000071
Figure FDA0002947445990000081
Figure FDA0002947445990000091
Figure FDA0002947445990000101
Figure FDA0002947445990000111
Figure FDA0002947445990000121
Figure FDA0002947445990000131
Figure FDA0002947445990000141
Figure FDA0002947445990000151
Figure FDA0002947445990000161
Figure FDA0002947445990000171
Figure FDA0002947445990000181
Figure FDA0002947445990000191
Figure FDA0002947445990000201
Figure FDA0002947445990000211
Figure FDA0002947445990000221
Figure FDA0002947445990000231
Figure FDA0002947445990000241
Figure FDA0002947445990000251
Figure FDA0002947445990000261
9. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 8.
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