CN111108108A - Organic compound, composition, organic photoelectric device and display device - Google Patents

Organic compound, composition, organic photoelectric device and display device Download PDF

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CN111108108A
CN111108108A CN201880060688.9A CN201880060688A CN111108108A CN 111108108 A CN111108108 A CN 111108108A CN 201880060688 A CN201880060688 A CN 201880060688A CN 111108108 A CN111108108 A CN 111108108A
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unsubstituted
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organic
organic compound
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金炳求
姜基煜
金亨宣
柳东完
申昌主
李韩壹
张起砲
郑成显
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Samsung Electronics Co Ltd
Samsung SDI Co Ltd
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Samsung SDI Co Ltd
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur

Abstract

The present invention relates to an organic compound represented by chemical formula 1, a composition comprising the same, an organic photoelectric device, and a display device.

Description

Organic compound, composition, organic photoelectric device and display device
Technical Field
The invention discloses an organic compound, a composition, an organic photoelectric device and a display device.
Background
An organic opto-electronic device (organic photodiode) is a device that converts electrical energy into optical energy and vice versa.
Organic photoelectric devices can be classified as follows according to driving principles. One is a photodiode in which excitons are generated from light energy, separated into electrons and holes, and transferred to different electrodes to generate electric energy, and the other is a light emitting diode in which a voltage or current is supplied to the electrodes to generate light energy from the electric energy.
Examples of the organic photoelectric device may be an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.
Among them, Organic Light Emitting Diodes (OLEDs) have recently received attention due to an increase in demand for flat panel displays. The organic light emitting diode converts electric energy into light by applying current to the organic light emitting material, and the performance of the organic light emitting diode may be affected by the organic material disposed between the electrodes.
Disclosure of Invention
[ problem ] to provide a method for producing a semiconductor device
One embodiment provides an organic compound capable of realizing an organic photoelectric device having high efficiency and long lifetime.
Another embodiment provides a composition capable of realizing an organic photoelectric device having high efficiency and long lifetime.
Another embodiment provides an organic photoelectric device including the organic compound or composition.
Another embodiment provides a display device including the organic photoelectric device.
[ technical solution ] A
According to one embodiment, there is provided an organic compound represented by chemical formula 1.
[ chemical formula 1]
Figure BDA0002416749160000021
In the chemical formula 1, the first and second,
X1and X2Independently of each other is O or S,
Ar1and Ar2Independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
L1is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, and
R1to R6Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, cyano, or a combination thereof.
According to another embodiment, a composition includes a first organic compound and a second organic compound including a carbazole moiety, the first organic compound being the organic compound, the second organic compound being represented by chemical formula 4.
[ chemical formula 4]
Figure BDA0002416749160000022
In the chemical formula 4, the first and second organic solvents,
Y1is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent substituted or unsubstituted C2 to C30 heterocyclic group,
A1is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R9ground R14Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,
R9and R10Independently exist or are linked to each other to form a ring, and
R11to R14Independently of R or11To R14Adjacent groups in (a) are linked to each other to form a ring.
According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the organic compound or the composition.
According to another embodiment, a display device including the organic photoelectric device is provided.
[ advantageous effects ]
An organic photoelectric device having high efficiency and long life can be realized.
Drawings
Fig. 1 and 2 are sectional views illustrating an organic light emitting diode according to an embodiment.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.
In the present specification, if no definition is otherwise provided, "substituted" refers to a group substituted with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine group, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof, in place of at least one hydrogen.
In an embodiment of the invention, "substituted" refers to a group substituted with deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, or C2 to C30 heteroaryl, in place of at least one hydrogen. Further, in embodiments of the present invention, "substituted" refers to a group substituted with deuterium, C1 to C20 alkyl, C6 to C30 aryl, or C2 to C30 heteroaryl, in place of at least one hydrogen. In addition, in the embodiments of the present invention, "substituted" refers to a group substituted with deuterium, C1 to C5 alkyl, C6 to C18 aryl, pyridyl, quinolyl, isoquinolyl, dibenzofuranyl, dibenzothienyl, or carbazolyl, instead of at least one hydrogen. In addition, in embodiments of the present invention, "substituted" refers to a group substituted with deuterium, C1 to C5 alkyl, C6 to C18 aryl, dibenzofuranyl, or dibenzothiophenyl, in place of at least one hydrogen. Further, in the specific examples of the present invention, "substituted" refers to a group substituted with deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl, or dibenzothiophenyl, in place of at least one hydrogen.
In the present specification, "hetero" means that 1 to 3 hetero atoms selected from N, O, S, P and Si are included in one functional group and the remainder is carbon, if no definition is otherwise provided.
In this specification, "aryl" refers to a group that includes at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form conjugates, such as phenyl, naphthyl, and the like, two or more hydrocarbon aromatic moieties may be joined by sigma bonds and may be, for example, biphenyl, terphenyl, quaterphenyl, and the like, or two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl. The aryl group can include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.
In the present specification, "heterocyclic group" is a general concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as aryl group, cycloalkyl group, fused ring, or a combination thereof. When a heterocyclyl group is a fused ring, the entire ring or each ring of the heterocyclyl group may contain one or more heteroatoms.
For example, "heteroaryl" refers to an aryl group that includes at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryl groups are directly connected by a sigma bond, or when a heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.
Specific examples of the heterocyclic group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl and the like.
More specifically, the substituted or unsubstituted C6 to C30 aryl group and/or the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, Substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted oxadiazinyl, substituted, Substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or combinations thereof, but is not limited thereto.
In the present specification, the hole characteristics refer to an ability to donate electrons to form holes when an electric field is applied, and the holes formed in the anode may be easily injected and transported into the light emitting layer due to a conductive characteristic according to a Highest Occupied Molecular Orbital (HOMO) level.
In addition, the electronic characteristics refer to an ability to accept electrons when an electric field is applied, and the electrons formed in the cathode may be easily injected and transferred into the light emitting layer due to a conductive characteristic according to a Lowest Unoccupied Molecular Orbital (LUMO) level.
Hereinafter, an organic compound according to an embodiment is described.
The organic compound according to one embodiment is represented by chemical formula 1.
[ chemical formula 1]
Figure BDA0002416749160000051
In the chemical formula 1, the first and second,
X1and X2Independently of each other is O or S,
Ar1and Ar2Independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
L1is a single bond, substituted or unsubstituted C1 to C20Alkylene, substituted or unsubstituted C6 to C30 arylene, or combinations thereof,
R1to R6Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, cyano, or a combination thereof.
The organic compound represented by chemical formula 1 may exhibit a fast electron transport property by including a fused ring of a substituted pyrimidine ring and benzofuran or benzothiophene, and may exhibit a faster electron transport property by further binding a dibenzofuranyl group or dibenzothiophenyl group to the benzofuran or benzothiophene of the fused ring. Therefore, when the organic compound is applied to a device, a device having a low driving voltage and high efficiency can be realized.
In addition, the organic compound represented by chemical formula 1 has a relatively high glass transition temperature, and thus, when the organic compound is applied to a device, deterioration of the organic compound during processing or operation may be reduced or prevented, thereby improving thermal stability and lifespan of the device. For example, the organic compound may have a glass transition temperature of about 50 ℃ to 300 ℃.
For example, X of chemical formula 11And X2May be the same or different. For example, X1And X2May be the same and X1And X2May be O or X1And X2May be S. For example, X1And X2May be different from each other and X1Can be S and X2Can be O or X1May be O and X2May be S.
For example, Ar of chemical formula 11And Ar2And may independently be a substituted or unsubstituted C6 to C30 aryl group, such as a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted triphenylene group. "substituted" means substituted with deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyanogen in place of at least one hydrogenRadical of (a).
For example, L1May be a single bond or a substituted or unsubstituted C6 to C30 arylene group. For example, L1May be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted anthracenylene group. For example, L1May be a single bond or a substituted or unsubstituted phenylene group. "substituted" refers to a group substituted with deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano in place of at least one hydrogen.
For example, R1To R6May independently be hydrogen, cyano, C1 to C20 alkyl, C6 to C30 aryl, or C6 to C30 aryl substituted with cyano.
For example, R1To R6May independently be hydrogen, cyano, C1 to C4 alkyl, C6 to C12 aryl, or C6 to C12 aryl substituted with cyano.
For example, the organic compound may be represented by any one of chemical formulas 2 to 5, but is not limited thereto.
Figure BDA0002416749160000061
In chemical formulas 2 to 5, X1、X2、Ar1、Ar2And R1To R6As described above.
For example, the organic compound may be represented by any one of chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, but is not limited thereto.
Figure BDA0002416749160000071
Figure BDA0002416749160000081
Figure BDA0002416749160000091
In chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, X1、X2、Ar1、Ar2And R1To R6As described above.
For example, in chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, L1May be a single bond or a substituted or unsubstituted phenylene group.
For example, in chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, L1May be a single bond.
For example, the organic compound may be one selected from the compounds listed in group 1, but is not limited thereto.
[ group 1]
Figure BDA0002416749160000092
Figure BDA0002416749160000101
Figure BDA0002416749160000111
Figure BDA0002416749160000121
Figure BDA0002416749160000131
Figure BDA0002416749160000141
Figure BDA0002416749160000151
Figure BDA0002416749160000161
Figure BDA0002416749160000171
Figure BDA0002416749160000181
Figure BDA0002416749160000191
Figure BDA0002416749160000201
Figure BDA0002416749160000211
Figure BDA0002416749160000221
Figure BDA0002416749160000231
The above organic compounds may be used alone or in combination with other organic compounds in organic opto-electronic devices. When the above organic compounds are used together with other organic compounds, they may be used in the form of a composition.
Hereinafter, a composition according to an embodiment is described.
The composition according to an embodiment may include the aforementioned organic compound (hereinafter, referred to as "first organic compound") and an organic compound having a hole property (hereinafter, referred to as "second organic compound").
The second organic compound may include, for example, a carbazole moiety and may be, for example, a substituted or unsubstituted carbazole compound, a substituted or unsubstituted biscarbazole compound, or a substituted or unsubstituted indolocarbazole compound, but is not limited thereto.
For example, the second organic compound may include, for example, a carbazole moiety represented by chemical formula 4.
[ chemical formula 4]
Figure BDA0002416749160000241
In the chemical formula 4, the first and second organic solvents,
Y1is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent substituted or unsubstituted C2 to C30 heterocyclic group,
A1is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R9to R14Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,
R9and R10Independently exist or are linked to each other to form a ring, and
R11to R14Independently of R or11To R14Adjacent groups in (a) are linked to each other to form a ring.
For example, in the definition of chemical formula 4, "substituted" refers to a group substituted with deuterium, C1 to C10 alkyl, C6 to C12 aryl, or C2 to C10 heteroaryl in place of at least one hydrogen, for example, deuterium, phenyl, o-biphenyl, m-biphenyl, p-biphenyl, terphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl in place of at least one hydrogen.
For example, the second organic compound may be a compound represented by chemical formula 4A.
[ chemical formula 4A ]
Figure BDA0002416749160000242
In the chemical formula 4A, the first and second,
Y1and Y2May independently be a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
A1and A2May independently be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R9to R11And R15To R17May independently be hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
m may be an integer of 0 to 2.
For example, Y of chemical formula 4A1And Y2May independently be a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, for example a single bond, a m-phenylene group, a p-phenylene group, a m-biphenylene group or a p-biphenylene group.
For example, A of chemical formula 4A1And A2May independently be a substituted or unsubstituted C6 to C30 aryl group, and for example the aryl group may be phenyl, biphenyl, terphenyl or naphthyl. Further, A of chemical formula 4A1And A2Can independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof, e.g., A of formula 4A1And A2May independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.
For example, R of formula 4A9To R11And R15To R17May be hydrogen, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl and may all be hydrogen, for example.
For example, m in chemical formula 4A may be 0 or 1, and for example, m may be 0.
For example, the binding site of two carbazolyl groups in formula 4A may be a 2, 3-bond, a 3, 3-bond or a 2, 2-bond, such as a 3, 3-bond.
For example, the compound represented by chemical formula 4A may be represented by chemical formula 4A-1.
[ chemical formula 4A-1]
Figure BDA0002416749160000251
In chemical formula 4A-1, Y1、Y2、A1、A2、R9To R11And R15To R17As described above.
For example, the compound represented by chemical formula 4A may be a compound in which one of the carbazole nuclei listed in group 2 is substituted with a substituent (— Y) listed in group 31-A1and-Y2-A2) Combined compounds, but are not limited to, menses.
[ group 2]
Figure BDA0002416749160000261
[ group 3]
Figure BDA0002416749160000262
In groups 2 and 3, is a connection point.
For example, the compound represented by formula 4A may be, for example, one of the compounds listed in group 4, but is not limited thereto.
[ group 4]
Figure BDA0002416749160000271
Figure BDA0002416749160000281
Figure BDA0002416749160000291
Figure BDA0002416749160000301
Figure BDA0002416749160000311
For example, the second organic compound may be an indolocarbazole compound represented by a combination of chemical formulas 4B-1 and 4B-2.
Figure BDA0002416749160000321
In chemical formulas 4B-1 and 4B-2,
Y1and Y3May independently be a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
A1and A3May independently be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
two neighbors of formula 4B-1 are bound to two neighbors of formula 4B-2,
the remaining two of formula 4B-1 are independently CR11Wherein R is11Are the same as or different from each other, and
R9to R11、R18And R19May independently be hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.
For example, Y of the formulae 4B-1 and 4B-21And Y3May independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
For example, A of the formulae 4B-1 and 4B-21And A3A C6 to C30 aryl group which may be substituted or unsubstituted, and the aryl group may be, for example, phenyl, biphenyl, naphthyl, terphenyl orAnthracenyl and preferably biphenyl, naphthyl, terphenyl or phenyl. Furthermore, A of chemical formulas 4B-1 and 4B-21And A3And may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
For example, the indolocarbazole compound represented by the combination of chemical formulas 4B-1 and 4B-2 may be represented by one of chemical formulas 4B-a and 4B-e.
Figure BDA0002416749160000322
Figure BDA0002416749160000331
In the chemical formulae 4B-a to 4B-e, Y1、Y3、A1、A3、R9To R11、R18And R19As described above.
For example, the indolocarbazole compound represented by the combination of chemical formulas 4B-1 and 4B-2 may be chemical formula 4B-c or 4B-d.
For example, the indolocarbazole compound represented by the combination of chemical formulas 4B-1 and 4B-2 may be chemical formula 4B-c.
For example, the compound represented by the combination of chemical formulas 4B-1 and 4B-2 may be one of the compounds of group 5, but is not limited thereto.
[ group 5]
Figure BDA0002416749160000332
Figure BDA0002416749160000341
Figure BDA0002416749160000351
Figure BDA0002416749160000361
Figure BDA0002416749160000371
The first organic compound and the second organic compound may include various components in various combinations. The composition may include the first organic compound and the second compound in a weight ratio of about 1:99 to 99:1, such as about 10:90 to 90:10, about 20:80 to 80:20, about 30:70 to 70:30, about 40:60 to 60:40, or about 50: 50.
The composition may further include one or more organic compounds other than the first organic compound and the second organic compound.
The composition may further comprise a dopant. The dopant may be a red, green or blue dopant. The dopant is a material which causes light emission in a small amount, and is generally a material such as a metal complex which emits light by being excited into a triplet state or more many times. The dopant may be, for example, an inorganic, organic or organic/inorganic compound, and may be included in one type or two or more types. The dopant may be included in an amount of about 0.1 to 20 wt% based on the total amount of the composition.
Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by formula Z, but is not limited thereto.
[ chemical formula Z ]
L2MX
In formula Z, M is a metal, L and X are the same or different and are ligands that form a complex compound with M.
M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L and X may be, for example, bidentate ligands.
Hereinafter, an organic opto-electronic device comprising the above organic compound or composition is described.
The organic opto-electronic device may be, for example, an organic light emitting diode, an organic opto-electronic device or an organic solar cell. The organic opto-electronic device may be, for example, an organic light emitting diode.
The organic opto-electronic device comprises an anode and a cathode facing each other and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the aforementioned organic compound or composition.
The organic layer may include an active layer such as a light emitting layer or a light absorbing layer, and the above organic compound or composition may be included in the active layer.
The organic layer may include an auxiliary layer disposed between the anode and the active layer and/or between the cathode and the active layer, and the aforementioned organic compound or composition may be included in the auxiliary layer.
Fig. 1 is a sectional view showing an example of an organic light emitting diode as an example of an organic photoelectric device.
Referring to fig. 1, an organic light emitting diode 100 according to an embodiment includes an anode 110 and a cathode 120 facing each other and an organic layer 105 disposed between the anode 110 and the cathode 120.
The anode 110 may be made of a conductor with a high work function to aid hole injection, and may be, for example, a metal oxide, and/or a conductive polymer. The anode 110 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; combinations of metals and oxides, e.g. ZnO and Al or SnO2And Sb; conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene) (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
The cathode 120 may be made of a conductor having a low work function to aid in electron injection, and may be, for example, a metal oxide, and/or a conductive polymer. The cathode 120 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or the like, or an alloy thereof; materials of multilayer structure, e.g. LiF/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2But not limited thereto,/Ca.
The organic layer 105 may include the above-described organic compounds or compositions.
The organic layer 105 may include a light emitting layer 130.
The light emitting layer 130 may include the above organic compound or composition as a host. The light emitting layer 130 may further include another organic compound as a host. The light emitting layer 130 may further include a dopant, and the dopant may be, for example, a phosphorescent dopant.
The organic layer 105 may further include an auxiliary layer (not shown) disposed between the anode 110 and the light emitting layer 130 and/or between the cathode 120 and the light emitting layer 130. The auxiliary layer may be a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, or a combination thereof. The auxiliary layer may include the above-mentioned organic compound or composition.
Fig. 2 is a cross-sectional view of an organic light emitting diode according to another embodiment.
Referring to fig. 2, the organic light emitting diode 200 according to this embodiment includes an anode 110 and a cathode 120 facing each other and an organic layer 105 disposed between the anode 110 and the cathode 120.
The organic layer 105 includes an electron assist layer 140 disposed between the emissive layer 230 and the cathode 120. The electron assist layer 140 may be, for example, an electron injection layer, an electron transport layer, and/or a hole blocking layer, and may facilitate the injection and transport of electrons between the cathode 120 and the light emitting layer 230.
For example, the above organic compound or composition may be included in the light emitting layer 230. The light emitting layer 230 may further include another organic compound as a host. The light emitting layer 230 may further include a dopant, and the dopant may be, for example, a phosphorescent dopant.
For example, the aforementioned organic compound may be included in the electron assist layer 140. The electron assist layer 140 may include the above-mentioned organic compound alone, may include a mixture of at least two types of the above-mentioned organic compound, or may include a mixture of the above-mentioned organic compound and another organic compound.
In fig. 2, the organic layer 105 may further include at least one hole assist layer (not shown) disposed between the anode 110 and the light emitting layer 230.
The organic light emitting diode can be applied to an organic light emitting display device.
[ embodiments of the invention ]
Hereinafter, the embodiments will be explained in more detail with reference to examples. However, these embodiments are exemplary, and the scope is not limited thereto.
Hereinafter, the raw materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich co., ltd., or TCI inc. (unless specifically noted) or synthesized by known methods.
(preparation of Compound for organic photoelectric device)
A compound as one specific example of the present invention was synthesized by the following procedure.
(first Compound for organic photoelectric device)
Synthesis of intermediates
Synthesis example 1: synthesis of intermediate A
[ reaction scheme 1]
Figure BDA0002416749160000401
Synthesis of intermediate A-1
4-chloro-2-fluorobenzonitrile (100g,0.64mol), methyl thioglycolate (70.0ml,0.77mol), and 1.2L N, N-dimethylformamide were placed in a 3-L round-bottom flask, and the internal temperature thereof was lowered to-5 ℃. Sodium t-butoxide (93.67g,0.96mol) was slowly added thereto, and the internal temperature was controlled not to exceed 0 ℃. The reaction was stirred at room temperature for 2 hours and then slowly added to cold water in a dropwise manner. The resulting solid was stirred at room temperature, filtered and dried to yield intermediate a-1(142.9g, 92%).
Synthesis of intermediate A-2
A mixture of intermediate A-1(140.0g,0.58mol) and urea (173.9g,2.90mol) was stirred in a 2L round bottom flask at 200 deg.C for 2 hours. The reaction mixture at elevated temperature was cooled to room temperature, poured into sodium hydroxide solution and after filtration and removal of impurities therefrom, the reaction was acidified (HCl,2N) to give a precipitate which was dried to give intermediate a-2(114.17g, 78%).
Synthesis of intermediate A
A mixture of intermediate A-2(114g,0.45mol) and oxychloride (1000mL) was stirred at reflux in a 2000mL round bottom flask for 8 hours. The reaction mixture was cooled to room temperature and then poured into ice/water while cooling vigorously, resulting in a precipitate. The reaction thus obtained was filtered to obtain intermediate a (122.8g, 94%, white solid). The results of elemental analysis of intermediate a are as follows.
Calculated C10H3Cl3N2S is C, 41.48; h, 1.04; cl, 36.73; n, 9.67; s, 11.07; c, 41.48; h, 1.04; cl, 36.73; n, 9.67; s,11.07
Synthesis example 2: synthesis of intermediates B, C and D
[ reaction scheme 2]
Figure BDA0002416749160000411
Intermediates B, C and D were synthesized in the same manner as in synthesis example 1, except that the starting materials were changed according to reaction scheme 2.
Synthesis example 3: synthesis of intermediate E
[ reaction scheme 3]
Figure BDA0002416749160000412
Synthesis of intermediate E-1
4-chloro-2-hydroxybenzonitrile (100g,0.65mol), ethyl bromoacetate (130.5g,0.78mol) and 1.3L N, N-dimethylformamide were placed in a 3L round-bottom flask and the internal temperature was lowered to-5 ℃. Then, sodium t-butoxide (93.88g,0.98mol) was added slowly, and the internal temperature was controlled not to exceed 0 ℃. The reaction was stirred at room temperature for 2 hours and then slowly added to cold water in a dropwise manner. The solid produced therein was stirred at room temperature, then filtered and dried to obtain intermediate E-1(132.2g, 90%).
Synthesis of intermediate E-2 and intermediate E
Intermediate E was synthesized in the same manner as intermediate a-2 and intermediate a of synthesis example 1.
Synthesis example 4: synthesis of intermediates F, G and H
[ reaction scheme 4]
Figure BDA0002416749160000421
Intermediates F, G and H were synthesized in the same manner as in synthesis example 3, except that the starting materials were changed according to reaction scheme 4.
Synthesis example 5: synthesis of intermediate I
[ reaction scheme 5]
Figure BDA0002416749160000422
Synthesis of intermediate I-1
200.0g (0.8mol) of 4-bromo-9H-carbazole, 248.7g (1.2mol) of iodobenzene, 168.5g (1.2mol) of potassium carbonate, 31.0g (0.2mol) of copper (I) iodide and 29.3g (0.2mol) of 1, 10-phenanthroline as intermediates were charged into 2.5L N, N-dimethylformamide in a 5L flask, which was then refluxed for 24 hours under a nitrogen stream. The obtained mixture was added to 4L of distilled water, and the solid crystallized therein was filtered and washed with water, methanol and hexane. The obtained solid was extracted with water and dichloromethane, and the organic layer thus obtained was treated with magnesium sulfate to remove water, followed by concentration and purification by column chromatography to give intermediate I-1 as a white solid (216.2g, yield 83%).
Calculated C27H18ClN3C, 67.10; h, 3.75; br, 24.80; n, 4.35; c C, 67.12; h, 3.77; br, 24.78; n,4.33
Synthesis of intermediate I-2
Intermediate I-1(216.0g,0.7mol), 4,4,4',4',5,5,5',5' -octamethyl-2, 2 '-bis (1,3, 2-dioxaborane) (212.8g,0.8mol), potassium acetate (KOAc,197.4g,2.0mol), 1' -bis (diphenylphosphino) ferrocene-palladium (II) dichloride (21.9g,0.03mol), and tricyclohexylphosphine (45.1g,0.2mol) were added to 3L N, N-dimethylformamide in a 5L flask, followed by stirring at 130 ℃ for 12 hours. After completion of the reaction, the reaction solution was extracted with water and EA, and the organic layer thus obtained was treated with magnesium sulfate to remove water, then concentrated and purified by column chromatography to give intermediate I-2 as a white solid (205.5g, yield 83%).
Calculated C26H25BN2O2C, 78.06; h, 6.55; b, 2.93; n, 3.79; o, 8.67; c, 78.08; h, 6.57; b, 2.91; n, 3.77; o,8.67
Synthesis of intermediate I-3
In a 5 liter flask, 150.0g (0.4mol) of intermediate I-2, 164.1g (0.8mol) of intermediate 1-bromo-2-nitrobenzene, 278.1g (2.01mol) of potassium carbonate and 23.5g (0.02mol) of tetrakis (triphenylphosphine) palladium (0) were added to 2L of 1, 4-dioxane and 1L of water, followed by heating at 90 ℃ for 16 hours under a nitrogen stream. After removal of the reaction solvent, the residue was dissolved in dichloromethane, filtered through silica gel/celite to remove an appropriate amount of organic solvent, and then recrystallized from methanol to give intermediate I-3 as a yellow solid (86.3g, yield 58%).
Calculated C18H12N2O2C, 79.11; h, 4.43; n, 7.69; o, 8.78; detection found C, 79.13; h, 4.45; n, 7.67; o,8.76
Synthesis of intermediate I
In a 1000ml flask, intermediate I-3(86.0g,0.23mol) and (309.5g,1.18mol) triphenylphosphine were added to 600ml dichlorobenzene, and after replacement with nitrogen, the mixture was stirred at 160 ℃ for 12 hours. When the reaction was complete, the solvent was removed therefrom and the product was purified by column chromatography using hexane to give intermediate I as a yellow solid (57.3g, yield 73%).
Calculated C18H12N2C, 86.72; h, 4.85; n, 8.43; detection found C, 86.70; h, 4.83; n,8.47
Synthesis of the final Compound
Synthesis example 6
[ reaction scheme 6]
Figure BDA0002416749160000441
Synthesis of intermediate 1-1
In a 250mL flask, intermediate A (10.0g,34.1mmol), 3-biphenylboronic acid (7.83g,34.53mmol), potassium carbonate (11.93g,86.33mmol), and tetrakis (triphenylphosphine) palladium (0) (1.2g,1.04mmol) were added to 80mL of 1, 4-dioxane and 40mL of water, followed by heating at 70 ℃ for 12 hours under a nitrogen stream. The organic layer was separated therefrom, added to 240mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and after removing an appropriate amount of organic solvent, recrystallized from monochlorobenzene to give intermediate 1-1(10.83g, 77% yield)
Synthesis of intermediate 1-2
In a 250mL flask, intermediate 1-1(10.5g,25.78mmol), phenylboronic acid (3.14g,25.78mmol), potassium carbonate (8.91g,64.45mmol), and tetrakis (triphenylphosphine) palladium (0) (0.89g,0.77mmol) were added to 70mL of 1, 4-dioxane and 35mL of water, followed by heating at 70 ℃ for 12 hours under a nitrogen stream. The organic layer was separated therefrom, added to 210mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and after removing an appropriate amount of organic solvent, recrystallized from monochlorobenzene to give intermediate 1-2(8.44g, yield 79%).
Synthesis of Compound 2
In a 100mL flask, intermediate 1-2(4.0g,8.92mmol), 3-dibenzofuranboronic acid (2.27g,10.70mmol), 0.15g (0.27mmol) of tris (dibenzylideneacetone) dipalladium, 0.33g (50% in toluene) of tri-tert-butylphosphine and cesium carbonate (5.81g,17.84mmol) were added to 60mL of 1, 4-dioxane, followed by heating at 110 ℃ for 12 hours under a nitrogen stream. The organic layer was added to 120mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and after removing an appropriate amount of organic solvent, recrystallized from monochlorobenzene to obtain compound 2(4.10g, yield 79%).
Calculated C40H24N2OS C, 82.73; h, 4.17; n, 4.82; o, 2.76; s, 5.52; detection found C, 82.73; h, 4.17; n, 4.82; o, 2.76; s,5.52
Synthesis examples 7 to 33
The following final compounds were synthesized in the same manner as in synthesis example 6, except that the compounds shown in table 1 were used as raw materials.
[ Table 1]
Figure BDA0002416749160000451
Figure BDA0002416749160000461
Figure BDA0002416749160000471
Figure BDA0002416749160000481
Figure BDA0002416749160000491
(second Compound for organic photoelectric device)
Synthesis example 34
[ reaction scheme 8]
Figure BDA0002416749160000501
Synthesis of intermediate B2
In a 1000mL round-bottom flask, 39.99g (156.01mmol) indolocarbazole, 26.94g (171.61mmol) bromobenzene, 22.49g (234.01mmol) sodium tert-butoxide, 4.28g (4.68mmol) tris (dibenzylideneacetone) dipalladium and 2.9mL (50% solution in methanol) tri-tert-butylphosphine were mixed with 500mL xylene, followed by reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000mL of methanol, and the solid crystallized therein was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite to remove a certain amount of organic solvent, and then recrystallized from methanol to obtain intermediate B2(23.01g, yield 44%).
Calculated C24H16N2C, 86.72; h, 4.85; n, 8.43; detection found C, 86.72; h, 4.85; n,8.43
Synthesis of Compound F-21
In a 500mL round-bottom flask, 22.93g (69.03mmol) of intermediate B2, 11.38g (72.49mmol) of bromobenzene, 4.26g (75.94mmol) of potassium hydroxide, 13.14g (69.03mmol) of copper iodide and 6.22g (34.52mmol) of 1, 10-phenanthroline were added to 230mL of DMF, followed by heating under reflux under a nitrogen stream for 15 hours. The obtained mixture was added to 1000mL of methanol, and the solid crystallized therein was filtered, dissolved in dichlorobenzene, filtered with silica gel/celite, to remove an appropriate amount of organic solvent, and then recrystallized with methanol to obtain compound F-21(12.04g, yield 43%).
Calculated C30H20N2C, 88.21; h, 4.93; n, 6.86; detection found C, 88.21; h, 4.93; n,6.86
Synthesis examples 35 to 47
The following final compounds were synthesized in the same manner as in synthesis example 34, except that the compounds shown in table 2 were used as starting materials.
[ Table 2]
Figure BDA0002416749160000502
Figure BDA0002416749160000511
Figure BDA0002416749160000521
Manufacture of organic light-emitting diodes I
Example 1
The glass substrate on which the ITO electrode was formed was cut into a size of 50mm × 50mm × 0.5mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes each, and then subjected to UV ozone cleaning for 30 minutes.
m-MTDATA with
Figure BDA0002416749160000522
Is vacuum deposited on the ITO electrode to form
Figure BDA0002416749160000523
A thick hole injection layer, and then on the hole injection layer
Figure BDA0002416749160000524
Deposition rate vacuum deposition α -NPB formation
Figure BDA0002416749160000525
A thick hole transport layer. Then, respectively in
Figure BDA0002416749160000526
And
Figure BDA0002416749160000527
Figure BDA0002416749160000528
deposition rate of (2) Ir (ppy)3(dopant 1) and Compound 2 (host) were co-deposited on the hole transport layer to form
Figure BDA0002416749160000529
A thick light emitting layer. Adding BALq to
Figure BDA00024167491600005210
Is vacuum deposited on the light-emitting layer to form
Figure BDA00024167491600005211
A thick hole blocking layer, and adding Alq3Vacuum depositing on the hole blocking layer to form
Figure BDA00024167491600005212
A thick electron transport layer. Sequentially vacuum depositing LiF (on the electron transport layer)
Figure BDA00024167491600005213
Thick electron injection layer) and Al (
Figure BDA00024167491600005214
Thick cathode) to fabricate an organic light emitting diode.
Examples 2 to 25
An organic light-emitting diode was manufactured in the same manner as in example 1, except that each compound shown in table 1 was used as a host of the light-emitting layer instead of the compound 2.
Comparative examples 1 to 5
An organic light-emitting diode was manufactured in the same manner as in example 1, except that the comparative compound 18, 40, 48, 155 or 189 was used instead of the compound 2 as a host of the light-emitting layer.
Comparative compounds 18, 40, 48, 155 or 189 were prepared by the methods disclosed in Japanese patent No.564848 or Japanese laid-open publication No. 2015-134745.
Figure BDA0002416749160000531
Evaluation example I
The driving voltage, efficiency and luminance of each organic light emitting diode according to examples 1 to 25 and comparative examples 1 to 5 were measured by supplying power from a current voltmeter (ketley SMU 236) and using a luminance meter, PR650 spectrum scanning source measuring unit (Photo Research Inc.).
The specific measurement method is as follows.
(1) Measuring current density change from voltage change
The current value flowing in the unit device was measured for the obtained organic light emitting diode while increasing the voltage from 0V to 10V using a current-voltage meter (Keithley 2400), and then the measured current value was divided by the area to obtain the result.
(2) Measuring brightness variation from voltage variation
While increasing the voltage of the organic light emitting diode from 0V to 10V, the luminance was measured using a luminance meter (Minolta Cs-1000A).
(3) Measurement of luminous efficiency
By using the luminance, current density and voltage (V) of the items (1) and (2), the same current density (10 mA/cm) was calculated2) Current efficiency (cd/A).
(4) Lifetime measurement
T95The lifetime was used to evaluate the time period (h) required for the organic light emitting diode to reach 95% luminance with respect to 100% of the initial luminance.
The results are shown in Table 3.
[ Table 3]
Figure BDA0002416749160000532
Figure BDA0002416749160000541
Referring to table 3, the organic light emitting diodes according to examples 1 to 25 exhibited equal or lower driving voltages, high efficiencies, and/or long lifetimes as compared to the organic light emitting diodes according to comparative examples 1 to 5. Accordingly, the host used in the light emitting layer of the organic light emitting diodes of examples 1 to 25 has excellent charge transport characteristics as a phosphorescent host material, while improving performance (such as efficiency improvement and equal or more excellent driving voltage reduction) and capability as an OLED material are maximized since its absorption spectrum has an overlapped emission wavelength region with that of the dopant. Most importantly, the lifetime is greatly improved.
In contrast, the comparative compound 18 used as a host in the organic light emitting diode of comparative example 1 exhibits extremely weak electron transport ability and may fail to achieve a balance between hole transport and electron transport, and therefore, the organic light emitting diode of comparative example 1 using it as a host of a light emitting layer has insufficient current efficiency. In addition, since the comparative compounds 18, 40, 48 and 156 used as hosts in the organic light emitting diodes of comparative examples 2 to 5 have a structure in which carbons adjacent to N of pyridine, pyrimidine and quinoxaline in a condensed ring are not substituted, i.e., the structure has CH, thermal stability and electrical stability are weak when applied to the light emitting layer of the organic light emitting diode, and thus, the organic light emitting diodes of comparative examples using them as hosts for the light emitting layer exhibit greatly reduced lifetime characteristics.
Production of organic light-emitting diodes II
Example 26
Using Compound 3 obtained in Synthesis example 7 as a host and (piq)2Ir (acac) (dopant 2) as a dopant, an organic light emitting diode was manufactured.
As the anode, use is made of
Figure BDA0002416749160000551
Thick ITO, and as cathode, use is made of
Figure BDA0002416749160000552
-thick aluminum. Specifically, a method of manufacturing an organic light emitting diode with a sheet resistance of 15 Ω/cm is described2The ITO glass substrate of (1) was cut into a size of 50mm × 50mm × 0.7mm, ultrasonically cleaned in acetone, isopropanol and pure water for 15 minutes, respectively, and subjected to UV ozone cleaning for 30 minutes to manufacture an anode.
On the substrate, at 650 × 10-7Formed by depositing N4, N4' -di (naphthalen-1-yl) -N4, N4' -diphenylbiphenyl-4, 4' -diamine (NPB) (80nm) at a deposition rate of 0.1 to 0.3nm/s under a vacuum of Pa
Figure BDA0002416749160000553
A thick hole transport layer. Subsequently, compound 3 of Synthesis example 7 was used under the same vacuum deposition conditions and a phosphorescent dopant (piq) was simultaneously deposited2Ir (acac), form
Figure BDA0002416749160000554
A thick light emitting layer. Herein, the deposition amount of the phosphorescent dopant was made 3 wt% based on 100 wt% of the total weight of the light emitting layer by adjusting the deposition rate.
On the light emitting layer, by depositing bis (2-methyl-8-quinolinate) -4- (phenylphenol) aluminum (BAlq) under the same vacuum deposition conditions
Figure BDA0002416749160000555
A thick hole blocking layer. Subsequently, it was formed by depositing Alq3 under the same vacuum deposition conditions
Figure BDA0002416749160000556
A thick electron transport layer. On the electron transport layer, a cathode is formed by sequentially depositing LiF and Al to fabricate an organic light emitting diode.
The organic light emitting diode has a structure of ITO/NPB (80nm)/EML (Compound 3(97 wt%) + (piq)2Ir(acac)(3wt％),30nm)/Balq(5nm)/Alq3(20nm)/LiF(1nm)/Al(100nm)。
Examples 27 to 35
An organic light-emitting diode was manufactured in the same manner as in example 26, except that compounds 9, 17, 18, 19, 23, 41, 97, 131 and 256 were used as hosts in the formation of the light-emitting layer instead of compound 3.
Comparative examples 6 to 13
An organic light-emitting diode was fabricated in the same manner as in example 52, except that comparative compounds 18, 40, 48, 155, 156, 189, 327 and 328 were used instead of compound 3, respectively.
Comparative compounds 18, 40, 48, 155 or 189 were prepared by the methods disclosed in Japanese patent No.564848 or Japanese laid-open publication No. 2015-134745.
Figure BDA0002416749160000561
Evaluation example II
The light emitting efficiency and the life span characteristics of each of the organic light emitting diodes according to examples 26 to 35 and comparative examples 6 to 13 were evaluated.
The specific measurement method is as follows, and the results are shown in table 4.
(1) Measuring current density change from voltage change
The current value flowing in the unit device was measured for the obtained organic light emitting diode while increasing the voltage from 0V to 10V using a current-voltage meter (Keithley 2400), and then the measured current value was divided by the area to obtain the result.
(2) Measuring brightness variation from voltage variation
While increasing the voltage of the organic light emitting diode from 0V to 10V, the luminance was measured using a luminance meter (Minolta Cs-1000A).
(3) Measurement of luminous efficiency
By using the luminance, current density and voltage (V) of the items (1) and (2), the same current density (10 mA/cm) was calculated2) Current efficiency (cd/A).
(4) Lifetime measurement
In the average luminance (cd/m)2) Maintained at 5000cd/m2Meanwhile, the time required until the current efficiency (cd/A) was reduced to 90% was measured, and the lifetime was obtained.
(5) Attenuation (Roll-off)
By calculating a maximum value of-5000 cd/m2The numerical efficiency reduction of (3) was calculated as a percentage (%)/maximum value.
[ Table 4]
Figure BDA0002416749160000571
Referring to table 4, the organic light emitting diodes of examples 26 to 35 have more excellent long life span at equal or lower driving voltage and equal or more excellent light emitting efficiency, as compared to the organic light emitting diodes of comparative examples 6 to 13.
Accordingly, the hosts used in the light emitting layers of the organic light emitting diodes of examples 26 to 35 have excellent charge transport characteristics as phosphorescent host materials, while, since their absorption spectra have overlapping emission wavelength regions with the absorption spectra of the dopants, performance improvements (such as efficiency improvement and driving voltage reduction, and in particular, long life) and the ability as OLED materials are maximized.
Manufacture of organic light emitting diodes III
Examples 36 to 60 and comparative examples 14 to 21
An organic light-emitting diode was manufactured in the same manner as in example 1, except that the first host and the second host shown in table 6 were used instead of the compound 2 as the host of the light-emitting layer. Herein, the dopant to first body to second body are co-deposited in a weight ratio of 10:45: 45.
Evaluation example III
The driving voltage, efficiency, luminance and lifetime of each organic light emitting diode of examples 36 to 60 and comparative examples 14 to 21 were measured by supplying power from a current voltmeter (ketley SMU 236) and using a luminance meter, PR650 spectral scanning source measuring unit (Photo Research Inc.). The results are shown in Table 5. T is95The lifetime was used to evaluate the time period (h) required for the organic light emitting diode to reach 95% luminance with respect to 100% of the initial luminance.
[ Table 5]
Figure BDA0002416749160000581
Referring to table 5, the organic light emitting diodes of examples 36 to 60 have improved efficiency/excellent long life at equal or lower driving voltage, compared to the organic light emitting diodes of comparative examples 14 to 21.
Manufacture of organic light emitting diodes IV
Examples 61 to 75 and comparative examples 22 to 25
An organic light-emitting diode was manufactured in the same manner as in example 26, except that the first host and the second host shown in table 7 were used instead of the compound 2 as the host of the light-emitting layer. Herein, the dopant to first body to second body are co-deposited in a weight ratio of 3:48.5: 48.5.
Evaluation example IV
The driving voltage, efficiency, luminance and lifetime of each organic light emitting diode of examples 61 to 75 and comparative examples 22 to 25 were measured by supplying power from a current voltmeter (ketley SMU 236) and using a luminance meter, PR650 spectral scanning source measuring unit (Photo Research Inc.).
The results are shown in Table 6.
[ Table 6]
Figure BDA0002416749160000591
Referring to table 6, the organic light emitting diodes of examples 61 to 75 had long lifetimes as compared to the organic light emitting diodes of comparative examples 22 to 25.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The foregoing embodiments are therefore to be understood as illustrative rather than limiting in any way.
The scope of the present invention is not limited thereto, but various modifications and improvements by those skilled in the art using the basic idea of the present invention defined in the appended claims are also within the scope of the present invention.

Claims (14)

1. An organic compound represented by chemical formula 1:
[ chemical formula 1]
Figure FDA0002416749150000011
Wherein, in chemical formula 1,
X1and X2Independently of each other is O or S,
Ar1and Ar2Independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
L1is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, and
R1to R6Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, cyano, or a combination thereof.
2. The organic compound of claim 1, wherein Ar1And Ar2Independently a substituted or unsubstituted C6 to C30 aryl group.
3. The organic compound of claim 2, wherein Ar1And Ar2Independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, wherein "substituted" means that at least one hydrogen of the group is replaced with deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano.
4. The organic compound according to claim 1, wherein the organic compound is represented by one of chemical formulas 2 to 5:
Figure FDA0002416749150000021
wherein, in chemical formulas 2 to 5,
X1and X2Independently of each other is O or S,
Ar1and Ar2Independently a C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
L1is a single bond, substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted C6 to C30 arylene, or combinations thereof, and
R1to R6Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, cyano, or a combination thereof.
5. The organic compound of claim 1, wherein
Ar1And Ar2Independently a C6 to C30 aryl group,
L1is a single bond or a substituted or unsubstituted phenylene group, and
R1to R6Independently hydrogen, cyano, C1 to C4 alkyl, C6 to C12 aryl, or C6 to C12 aryl substituted with cyano.
6. The organic compound of claim 1, wherein the organic compound is selected from the compounds listed in group 1,
[ group 1]
Figure FDA0002416749150000031
Figure FDA0002416749150000041
Figure FDA0002416749150000051
Figure FDA0002416749150000061
Figure FDA0002416749150000071
Figure FDA0002416749150000081
Figure FDA0002416749150000091
Figure FDA0002416749150000101
Figure FDA0002416749150000111
Figure FDA0002416749150000121
Figure FDA0002416749150000131
Figure FDA0002416749150000141
Figure FDA0002416749150000151
Figure FDA0002416749150000161
Figure FDA0002416749150000171
Figure FDA0002416749150000181
7. A composition, comprising:
a first organic compound, said first organic compound being the organic compound of claim 1, and
a second organic compound comprising a carbazole moiety, the second organic compound being represented by chemical formula 4:
[ chemical formula 4]
Figure FDA0002416749150000191
Wherein, in chemical formula 4,
Y1is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent substituted or unsubstituted C2 to C30 heterocyclic group,
A1is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R9to R14Independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and
R11to R14Independently of R or11To R14Adjacent groups in (a) are linked to each other to form a ring.
8. The composition of claim 7, wherein the second organic compound is represented by chemical formula 4A or a combination of chemical formulae 4B-1 and 4B-2:
[ chemical formula 4A ]
Figure FDA0002416749150000192
Figure FDA0002416749150000193
Figure FDA0002416749150000201
Wherein, in chemical formula 4A, chemical formula 4B-1 or chemical formula 4B-2,
Y1to Y3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
A1to A3Independently a substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or combinations thereof,
two adjacent ones of formula 4B-1 are combined with two ones of formula 4B-2,
the remaining two of formula 4B-1 are independently CR11Wherein R is11Are the same as or different from each other,
R9to R11And R15To R19Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
m is an integer of 0 to 2.
9. The composition according to claim 8, wherein a of chemical formula 4A, chemical formula 4B-1 and chemical formula 4B-21To A3Independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
10. The composition of claim 8, wherein
The second organic compound is represented by chemical formula 4A-1, 4B-c or 4B-d:
[ chemical formula 4A-1]
Figure FDA0002416749150000211
Figure FDA0002416749150000212
Wherein, in chemical formulas 4A-1, 4B-c and 4B-d,
Y1to Y3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
A1to A3Independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof, and
R9to R11And R15To R19Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.
11. An organic opto-electronic device, comprising:
an anode and a cathode facing each other, and
an organic layer disposed between the anode and the cathode,
wherein the organic layer comprises the organic compound of claim 1 or the composition of claim 7.
12. The organic optoelectronic device of claim 11, wherein
The organic layer comprises a light-emitting layer,
the organic compound or the composition is included as a host in the light-emitting layer.
13. The organic optoelectronic device of claim 11, wherein
The organic layer comprises:
a light-emitting layer, and
an electron assist layer disposed between the cathode and the light emitting layer,
the electron assist layer comprises the organic compound of claim 1.
14. A display device comprising the organic optoelectronic device of claim 11.
CN201880060688.9A 2017-09-20 2018-09-12 Organic compound, composition, organic photoelectric device and display device Pending CN111108108A (en)

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